Out of the Way is a superb three part tale by Sascha Davidson on a subject matter many on this web site will enjoy. It might be wise to read the earlier instalments before reading Michelle’s continuation.
I have not been able to reach Sascha to ascertain consent so if she is reads this can she get in touch with me please at firstname.lastname@example.org.
The original Out of The Way story by Sascha Davidson can be found following these links to Fictionmania:
Out of the Way Part 1
Continuation of the original Sascha Davidson story
By Miss Michelle Miller.
Sarah returned to the Club to retrieve her spouse, who was now irrevocably “Roberta.” She made her way through that various patrons until she found Jodie sitting on a stool at a high table, sipping a cosmo. What appeared to be a gift box was also on the table. In the dim light, it took a moment to notice Roberta, keeling at the foot of Jodie’s stool. Her ball gag was in place, and Jodie dangled the loop of Roberta’s leash from her little finger. Roberta looked almost exactly as she did when Sarah gave her to Jodie a week ago, except she could not bring herself to look Sarah in the eye. After exchanging air kisses with Jodie, she took a seat at the other stool. Jodie signaled the waiter to bring another cosmo for Sarah.
“Before I return your sissy, you will have to tell me how things went with that hunk you took home.”
Barely glancing down at Roberta, Sarah proceeded to gush. “His name is Jack, and it was fantastic!” Sarah recounted a number of their exploits, and concluded that she would be sharing her bed with him on a regular basis.
“What about your sissy?”
“Jack is very handy, so we’ve fixed up one of the extra rooms for Roberta. I’m sure she’ll love it. We made it very girly. It has huge closets with plenty of room for all of her old clothes as well as the new ones she will probably need. It has a terrific bath, and I got her the enema nozzle you suggested. Now tell me, how was my little sissy?”
“I told you on the phone about some of her training, and I now I am certain you will find her vastly improved, both as a maid and a wonderful source of satisfaction between one’s legs.”
“I thought she was locked up?”
“Ofcourse. She always should be down there. Most sissies are improved by that. Her tongue, on the other hand, has come a long way. What’s nice about that is that it can be put to use almost anywhere. Now,” and she tugs Roberta’s leash. Roberta comes to her feet and curtsies. She folds her hands over her apron and avoids Sarah’s gaze.
“That’s a nice touch, Jodie. Does she do that all the time now.”
“Except when she’s told not to. So here she is. She has everything she left with plus her favorite butt plug.” Jodie winks at Sarah. “I think she really likes that now, don’t you sissy?” Roberta slowly nods her head yes. “Yes, you’ve become a very good girl, haven’t you sissy?” Another nod. “And as a reward, my husband and I have gotten you this little present to remember us by.” She hands Roberta the box. “Open it sweetie and show it to your mistress.”
Roberta slowly undoes the pink ribbon and opens the box. Her eyes go wide, and she lifts the satin hanger to reveal a red gypsy style baby doll nighty with transparent panties.
Sarah claps her hands quickly. “Oh, it’s just like her outfit from the movie! Jack and I both think she was great in that! Here, Roberta, turn around and I will remove your ball gag so you can thank Jodie for her present.”
Again facing Jodie, he curtsies and says “Thank you mistress for the wonderful present.” His voice is now distinctly girlish.
“Wow, I love that voice. How did you get her to talk like that?”
“Firm instruction, Dear. And like her curtsies, she will talk like that until she is given permission to do otherwise.”
“What if she were dressed like a man?”
“She’d still need your permission. Right sissy?”
She bobs, “Yes ma’am.”
Roberta has still been unwilling to actually look at her wife. “So sissy,” says Sarah as Roberta continues to look away. “Roberta! Look at me when I am speaking to you.” Roberta slowly turns and their eyes meet. Roberta’s eyes moisten. Sarah smiles with delight. “Jodie has told me all about your training and progress. I think we should continue that, what with Jack around and all. OK sweetie?”
“Please, no, Sarah,” she says in a less than girly voice.
She bobs quickly. “Please, please, no ma’am.” she says in a very girly voice.
“Sorry Roberta, that’s what I want. If you don’t want to keep on as my sissy, then you won’t come home to your nice new room, you’ll just have to go back with Jodie until you’re properly trained.”
“Oh, noooo,” she bobs, “I want to go home. Pleeeze.”
“You’re really sure?”
“Yes, ma’am,” she bobs.
“Very well. Think of this as a trial stay. You will be perfectly obedient and you will be punished if you ever dare not to be?”
“And Jack, too, of course?”
“Oh….sigh…oh, yes ma’am.”
“Now that that’s all clear, sissy, why don’t you put your present back in the box, and save the ribbon like a good girl. Sarah and I have some things to discuss. Get back on your knees. Sarah, spread your legs a bit and let sissy show you what she can do with that tongue of hers?”
Later, a well satisfied Sarah slouches over the table and pants to Jodie. “Wow. You really did work wonders on my husb….sissy. She never did anything like that before. Whew. I suppose I should let her up at some point. Her makeup must be a mess.”
“Actually, I told her to put on the nonsmearable stuff, so she probably won’t need more than a touch up. By the way, if we had her another week, you would really be amazed.”
“I really should take her home for now.”
“Don’t tell me you’re feeling guilty.”
“Oh, no. I might have last week, but that was before the movie …and Jack. He is submissive but not a sissy like Roberta. Before, it used to annoy me when Roberta made us play dress up games and then go back to being all bossy. She’s going to learn a whole new definition of bossy. She wanted to play at being girly. I think I just might make her a girl. I can’t wait put her through her paces tonight. At very least, she is going to wear that nighty for us when we all watch her movie. Speaking of her movie, I’m thinking about letting you market that. No one would ever guess who she is, and she really is cute. She could use a little extra money for clothes. I am only going to let her dress up like a man for work. I’m even toying with entering her in one of those gay beauty pageants once she develops a suitable talent. Dance lessons perhaps. We’ll see. O.K. Roberta, you may come out. Pull my panties up please. Good girl.”
“Here’s your purse. You really better fix that make up” says Jodie as she hands Roberta a large patent handbag. She smiles at Sarah. “Another little gift. She needed somewhere for her makeup, her ball gag, and her butt plugs.”
Roberta’s makeup restored, Jodie hands Sarah the leash. “I suppose you should take her home. Look, let’s stay in touch, if you ever need any help with Roberta, just let us know. We’d be happy to baby sit her any time. Jack, too.”
“Thanks Jodie. O.K., let’s get going sissy. Don’t forget your present,” and she leads the most dismayed sissy to the door. She somehow thought all this would end when Sarah picked her up.
“Bye, bye, sissy,” the coat check girl giggles as they pass by.
They get to the large black Mercedes and Sarah leads Roberta to the passenger door (Roberta had driven a week ago). “Get in Roberta and keep those knees together. That’s a girl.” Sarah settles into the driver’s seat. “This isn’t a very sissy car, is it Roberta? I really think I should drive this one, and you can have my candy white Beetle. I think that will be much more appropriate, don’t you.”
Roberta is more than surprised, She thought all nightmare would be over. That she would be resuming her old life with Sarah. “You have got to be fucking kidding. This has to be some kind of joke, Sarah.” She says in a very unfeminine voice.
“Listen sissy,” Sarah hisses. “I am not joking. Now, Roberta, I am going to take you back to Jodie right now, or you are going to behave like a good girl and listen obediently while I explain our new life and your sissy rules. Which is it, Roberta?”
“Please, Sarah.” She says in a more feminine voice.
“Sarah? Hrumph!” She starts to open the car door.
“Ma’am. I’m sorry ma’am. Please don’t take me to that woman.” She says in her most girly voice.
“So what are you going to do?”
“Um, I’m going to behave.”
“Um, a good … girl. Ma’am.”
Sarah grabs her handbag, exits the car, comes around to the passenger side, opens the door, takes Roberta’s leash, pulls the sissy out of the car, and instructs her to “bend over and keep your hands on the fender and don’t say a word.” She lifts Roberta’s skirts and secures them up by slipping some of the fabric under the maids apron sash. She slowly lowers Roberta’s panties. The air is cool on Roberta’s behind, which is still a little sore from her last discipline by Jodie. Roberta can just see her remove a hair brush from her handbag. SLAP! Sarah administers what will be the first of ten burning blows. A passing couple pauses to watch as Roberta breaks into sobs after the fourth spank. Finally they stop, and Roberta is left sobbing with her very red bottom in the air. Sarah looks at the grinning couple. “Sorry, she needed a bit of discipline.”
The woman laughed. “Most sissies do, don’t they?” And she and her companion moved on to their car.
“Now, you sissy, stand up, fix your things, and get back in the car. Let’s see if you really can be a good girl.”
Still sobbing, Roberta does as ordered, and Sarah closes the door.
“Now that I have your attention, Roberta. The very first thing you need to get into your little brain is that you really are a sissy girl to me and you will speak and behave as one except when I give you permission to pretend to be a man. That means you are a sissy girl even if I let you dress up like a man but haven’t given you permission to pretend to be a man. Of course, you will never actually be a man. Understand so far?”
Roberta is still breathing heavily from her spanking. “Yes, ma’am. But…”
“Sissy, sissy. You haven’t been given permission to speak. You may always respond to questions or orders, but otherwise you need permission. You shall never interrupt, but otherwise, a single respectful ‘ma’am?’ or delicately raised hand is acceptable. If permission is not granted, assume it is denied and DO NOT ask again. Got it?”
“Your curtsey rule will continue except when you are allowed to pretend to be a man, and I expect we will be dressing you as a girl or a sissy at all other times. As you already know, sissies are very obedient and are punished when they are not. You will obey just about everyone, including Jack or whatever real man I choose to have around. You will keep a hair brush in your hand bag at all times, in case you need to be punished. I may not always have mine handy. Still with me?”
“Yes, ma’am.” He is praying this really is a joke.
“You can’t wear maid’s uniforms all the time, so tomorrow, I will give you a first list of clothes and other things you will need for the new you. I expect you to begin to acquire those things tomorrow. It should be fun for you. All girls love to shop.”
Roberta raises her hand and softly says, “ma’am?”
“You mean by myself. In the stores?”
“Of course. You need to try everything on.”
Hand up again.
“But how will I explain why I’m doing that?”
“Really. It will probably be obvious that you are a sissy, but if anyone doesn’t get it, just tell them what you are. And, now that you’ve finished crying, fix your makeup.”
Since it is fairly late when they get home, after being introduced to Jack, to whom she curtsied, Roberta is shown to her new bedroom and told to change into her red nighty and report to the library so they can all watch her movie before going to bed. She is reminded to knock before opening any closed door. The room is as girly as can be. Pink and white. A frilly white bedspread and skirt beneath the makeup table. Framed drawings of Victorian girls in elaborate dress. A white book case filled with dolls and stuffed animals which Sarah had kept since she was a girl. Her cell phone as been switched for a pink one as has her computer. All of her female things hang in one of the huge closets as is her shoe collection. Her undies are in the chests of drawers, but only two sets of Robert’s are to be found. His clothes are in the other closet.
She works her way out of her maid’s clothes and foundations, puts them away and goes into the bathroom to tinkle. There she notices the dreaded enema nozzle. Drat! She tinkles and, to be safe, she removes her butt plug and endures an enema. Nice and clean, she reinserts the plug and dons the dreaded red baby doll, the garter belt and stockings, and the red neck ribbon all of which were in the box from Jodie. Is it a coincidence Jodie had made her polish her nails the same red? She makes her way to the library, knocks softly, hears giggles from within, and waits for what seems like forever before Sarah bids her to enter. She sees the two of them snuggling on the sofa. Sarah is in pajamas and Jack is nude and sports a gigantic hard on. She gives a quick bob. Embarassed as can be. Her red face matches her bottom.
“Give us a little twirl, Roberta. It will get us in the mood for your movie. Now, you can sit at our feet. Yes. Hmm, since Jack and I are holding hands, why don’t you hold Jack’s penis in your hand. Don’t look like that. Show Jack you’re sorry by giving it a kiss. No, on the head. Good girl. Now hold it gently while we all watch your performance. Wow, Roberta, that guy’s as big as Jack, isn’t he?” Roberta shakes her head yes. “Roberta, don’t you dare let Jack get soft. If you feel him doing that, just suck him till he’s hard again. Show me you understand and then we’ll start your movie. That’s a girl.” This is the first time Roberta has seen the video. It’s certainly no turn on for her, but at least it keeps Jack happy and spares Roberta any more lip contact. Her manicured hand looks so dainty as it holds Jack’s mighty member. Finally Sarah cheers: “Brava! Brava!” She replaced Roberta’s hand with her own. “Wow, that’s gotten us both in the mood. So, sissy, why don’t you scoot off to your pretty room. Tomorrow morning, you should be in uniform and have breakfast ready at eight thirty. Nightey night, sissy.”
“Good night, ma’am,” she bobs.
The next morning, Roberta serves breakfast to Sarah and Jack who both have other commitments for the day. Jack takes his leave, having been given instructions to take and text a photo of his penis at least once each hour to Sarah … and to Roberta. Sarah turns her attention to Roberta. “Here is your shopping list, Roberta. I have to get going soon, so put off cleaning up the breakfast stuff for the moment and run along to your room. Remove your uniform, but leave everything else on. You may remove your makeup and nail polish, and of course your wig,” she giggles. I will be in to help you get ready for your trip to the mall.”
Later, Roberta stands in the middle of her new room in stockings, tight panties with bum enhancing pads, corset, and B cup bra with fillers. Roberta raises her hand to ask a question and is ignored.
“If you don’t wear all this, you’ll have a very hard time making sure everything fits. Otherwise, I’m going to let you dress up like a man.” She sifts through Roberta’s male closet and comes upon a frilly tuxedo shirt worn once because of a wedding and never again. “Here Roberta, try this, we may as well get some use out of it. A tiny bit tight in the chest, but not bad. Now, let’s try the tuxedo trousers. Yes, tuck in your shirt. Hmm. We need to do something about that waist. Pull the side tabs all the way in. I guess that will work for today. Now shoes. Ah yes.” She goes back to the closet and extracts Robert’s patent leather formal pumps with the grosgrain bows. She always thought they were a bit effeminate, but they were correct and almost all the civilized men wore them. Now, with his figure and frilly shirt, they were positively feminine. Perfect. “No need or socks, Roberta.” She has Roberta sit on her vanity stool. She applies styling gel to Robert’s hair and gives it a very high part, making it look quite feminine. “It’s too warm to wear a jacket, so I’m going to try to find you a pocket book. While I’m doing that, why don’t you put on a little mascara, just a little blush, and some lip gloss in the palest pink you have.”
Roberta does as ordered and Sarah returns with a large patent clutch. “Look, Roberta, it matches your shoes! I’ve got to run. Oh, Roberta before you leave, you should polish your nails to match your lip gloss and also a spritz of your signature scent.”
Roberta raises her hand. Ignoring Roberta, Sarah turns to leave but turns back a moment to say “Oh, I almost forgot,” she laughs, “You have permission to pretend to be a man while you are shopping….except keep your girly voice. I’ll call later to check on you. Be a good girl!” And she is gone.
Roberta cleans up the breakfast things, does her nails in an almost clear pink polish (subtle but noticeable), and applies a quick spray of Opium (her favorite scent). She looks at Sarah’s list. OMG The first item: “Have ears pierced.” She reads down the list: “Today be sure you come home with a very frilly white blouse (pref. back buttoned), some tight black shorts (NO front zip!), shiny Mary Janes with heels, and some white ankle socks with ruffles. Jack’s idea.” She puts the list in her bag which already contains her makeup in case Sarah somehow checked, her credit cards and license, a pink comb, several lacy hankies, and her iPhone. She dreads this excursion only slightly less than a visit with Jodie, but definitely less. She sets out in Sarah’s Beetle (now hers). She has left her sunglasses in the Mercedes and has no choice but to wear the very girly white ones Sarah had left in the car. On her way to the mall, she notices a jewelry shop with a sign offering free piercing and at this hour it seemed empty. She stopped, screwed up her courage, and moved slowly to the shop. Once in, she removed her glasses and placed them into her bag. Roberta was cute and girly, but with that hair and without more makeup, on any close inspection she is clearly not a girl. She approaches the counter which is attended by a woman in her late twenties, who is slightly perplexed by her customer. Well, a customer is a customer, and she gets a commission on every sale.
“May I help you?”
“Yes, please. I need some earrings.” She says softly and blushes.
“Pierced or clip on?”
“Will these be your first pair?”
“Then let me suggest these posts with little stones and maybe these hoops for once your piercings heal. You do want to be pierced, don’t you?”
“I’m afraid so.”
“Come over here and sit down, dear. Cute hair. Did you style it yourself?”
Roberta knew something like this was bound to happen. “Um, no. My wife….”
“Ah. And do you really want your ears pierced today?”
Roberta shakes her head no.
“Then we really don’t have to do this. We can give you clip ons.”
“No, I really have to do this.”
“Your wife? She’s making you do this?”
Roberta nods yes.
“Did she pick out your cute outfit, too? You do look like a perfect sissy. With longer hair, you’d look like a perfect girl. Anyway, let’s get you pierced. It won’t hurt much, so be a brave girl for me.”
Soon, Roberta’s ears sport those sparkely posts. Very brave dear. If you will pardon my asking, is your wife really making you do this?” Roberta nods. “You weren’t a sissy before?” Roberta shakes her head. “You must be in big trouble, sweetie.” Roberta nods.
She pays the salesgirl who notes that they seemed to have left the “a” off of the end of her first name. She puts her other purchase in her bag and takes out her list. The salesgirl can’t help but peek.
“Wow, that’s quite a list. Your wife’s I assume?”
Roberta nods, and just then her phone rings (the melody is “Girls Just Want to Have Fun”). It is Sarah and facetime is on. “Yes ma’am” she says and moves each of her ears to the face of the phone.
The salesgirl is scrutinizing Roberta’s list. “Is this all for you, honey.”
“You know, if money is not a problem, I may be able to help you.”
“I have a friend who’s a private shopper at Bloomies. I can call and see if she’s got anything going on. I’m a little concerned about finding that last outfit, but if anyone can find it, it will be Tiffany. Would you like me to call her for you, hun?”
“Oh yes. Please!” What a stroke of luck.
“O.K. I’ve got her in my speed dial. Hi Tiff. It’s me, Ashley. Are you busy right now? Good. I have someone here who could use your help with what looks like a sizable purchase. Shall I send ….um, I’m not quite sure which pronoun to use. Well, this person seems to be in trouble with his wife, and she’s dressed him like a sissy. Actually, except for his hair, he looks more like a girl than a guy. He’s rather cute actually. His name is Robert or maybe Roberta today. He is very polite and, as you might guess, seems very scared. She has sent him off with a long list of girly purchases, starting with earrings. Yes, I have just pierced his ears. Let me send you a pic. Hold still for a second Roberta. There. I’ll text this to you and call you right back. …Sorry about the “Roberta” sweetie, but you just don’t look like a “Robert.” …What do you think Tiff? Yeah, I just told him the same thing. Good idea. I’ll send him right over. ….Give me your list, hun, I’ll take a couple of shots and text them to Tiff so she can get started. I don’t know what you did to deserve this, but it sure looks like you will be quite the girl when this is over…or sissy, judging from that last outfit.”
Following Ashley’s directions, Roberta makes her way through the department store to Tiffany’s small office. Along the way, she received a number of stares, doubletakes, and a few snickers, but it could have been worse. The door is open, hearing Roberta’s soft knock, Tiffany looks up and slowly looks Roberta up and down, finally, stifling a giggle, she says, “You must be Roberta. Your wife has certainly done a number on you. Wow. I can see that you are actually wearing a man’s shirt, pants, and shoes, but you look like the most feminine sissy I have ever seen, and we do get our share of sissies and trannys here. Let me see your list sweetie, Ash’s photos weren’t perfect.”
Roberta removes the list from her pocketbook and hands it to Tiffany who says, “Have a seat there while I double check this. I think this could be a long day. Oh Roberta, just between us girls, you should keep your legs together or crossed, even in pants. I think the more ladylike you act, the less attention you are likely to attract. I have reserved a room for us (it’s one of the perks of having a personal shopper) so we will be going there in a few minutes. Usually, it will be just you and me, but some of my colleagues will be helping as well. We understand that you might be a little embarrassed, but we will try to keep you comfortable. Given your appearance, I think it would be best if we call you Roberta, or she, or her. Don’t you?”
“Um, I suppose so, ma’am.”
“Oh, Roberta, call me Tiff, silly, I not your wife. Now, I’ll just call for Missy, she’s one of the interns who will be helping us, and we’ll get started.”
They reach the room with only a couple of stares. The room is plushly carpeted, with several comfortable chairs, mirrored walls, a large clothes rack, and a private changing room. “We’ll begin with you removing your outerwear so we can measure you and get your sizes right. Your men’s clothes are no help.” There is a knock on the door and Missy joins them. “Ah, Missy, this is Roberta. We are going to have a busy day with her.”
Missy looks shocked.
“Don’t look that way, Missy. I guess Roberta is your first sissy; she won’t be your last. She is really very sweet, and she’s just doing what her wife wants. So Roberta, remove your silly men’s clothes.”
Roberta blushes as she is measured and inspected in her undies. Missy is oblivious to Roberta’s chastity device, but Tiffany knows exactly what the outline in Roberta’s foundation means. She touches it lightly. “OMG Roberta, you really are in a fix, aren’t you?”
“Um Hum.” The blushing Roberta says softly.
“Well, Missy, Roberta’s first priority is a shorts outfit. She needs some snug fitting black shorts or hot pants..no front zippers and a frilly white blouse..back button if possible. You go for those and I’ll get her footwear. Roberta, you can wear this smock while you wait…and here’s the new Vogue if you start to get bored.”
And, so began Roberta’s acquisition of what would become her wardrobe for everything but work and very special occasions. Tiffany and Missy were good at their jobs, and by mid afternoon they had assembled almost everything on Sarah’s list. Scrolling past Jack’s texts of his mighty member, Roberta sends one to Sarah to report her success, including the shorts outfit Sarah had made top priority. Sarah responded with a direction for her to send an image of her in that outfit, with a copy to Jack since he is the one who thought Roberta should have a proper sissy outfit. Tiffany was in the process of totaling Roberta’s purchases. Roberta turned to Missy, “My wife wants to see me in that shorts outfit, would you mind if I tried it on again?”
“Not at all, Roberta. I’ll help you with the buttons.”
Missy had done a perfect job finding what Sarah ordered, and soon Roberta is posing in the high waisted back zip shorts. They were black, very tight in the tush but a bit roomy in the legs with their five inch inseam. The white blouse was frilly indeed, with lacy ruffles across the front, short very puffy sleeves with a little pearl buttons at the bands, which matched the row running up and down the back. The ruffled collar was adorned with a black satin bow. The lacy ruffles on her turned down socks are much like those on the blouse, and Tiff had found her a pair of black patent Mary Janes with three inch heels, almost pointed toes, and a low strap with a pearl button. Missy takes several photos showing the back and front of the outfit including the patent leather pocketbook that was now a necessity and a close up of her shoes.
Missy giggles. “Your wife could not have asked for a more sissy outfit. You do look cute, but I don’t think I would ever wear something like this.”
“I’m not exactly happy with it either.” Roberta observes as she texts the images to Sarah and that Jack. A few moments later, her phone dings. “Oh, no!”
“Doesn’t she like it? It’s exactly what she asked for.”
“She likes it, all right. She wants me to wear it home.”
“You poor thing, although what you wore in was pretty sissyish, too.”
“At least those were men’s clothes. It was embarrassing enough to come here in those. I don’t know how I’m going to get to my car.”
Tiffany overhears this. “Don’t worry Roberta. You’ve bought so much stuff, I’ll get one of the stockboys to help you carry it to your car. He’ll keep an eye out for you. Too bad you don’t have a wig, then no one would guess you weren’t a girl.”
The stockboy can’t believe this, having never encountered a sissy like Roberta. “Please, Billy,” admonishes Tiff, don’t let anyone give her a hard time. As you can see, she’s a very good customer, and we want her to feel comfortable coming back.”
The trip to the car was not fun. Along the way, she explained to Billy several times that she was not gay and that she did not choose her outfit. Finally Roberta arrives home….just a few minutes after Sarah….and Jack, both of whom break out in laughter when they see Roberta. When Sarah regains her composure she says “You were right, Jack, it makes her look just like the sissy she is. Don’t you just love your outfit, Roberta? You look cute and it saves having to explain to anyone that you’re a sissy. Well, Roberta?”
“Um, yes, I guess.”
“Roberta, where are your girly manners. Oh that’s right, I had given you permission to pretend to be a man, didn’t I? Well enough of that. No one could pretend to be a man dressed like you are anyway, could they Roberta?”
“No ma’am,” she curtsies and then timidly raises her hand.
“I need to tinkle, ma’am.”
Sarah laughs, “I suppose you do. By the way, I assume you’re not wearing one of your plugs since you were pretending to be a man?”
“Um, no ma’am.”
“Well, then, after you tinkle, why don’t you use your little nozzle and insert a nice plug. Then, put on your proper make up and nail enamel. After that, Jack will help you bring all your new stuff in from your car.”
“Yes, ma’am,” she curtsies.
Roberta returns and curtsies. Jack grins. “See, Sarah, don’t you think she really looks appropriate now?”
“Well, certainly better than when she pretends to be a man. But really Jack, don’t worry, even without her sissy outfit, I now know she’s really a girl after all…something you could never be and I would never want you to be. Meanwhile, I still have a couple of errands to do. So why don’t you two move Roberta’s new stuff while I’m gone? Jack, you’re in charge of course. Roberta, be a good girl so Jack won’t have to discipline you. Understand?”
“My god, sissy, you really shop like a girl, don’t you? This is our fourth trip, and there’s still one more to go. It looks like Sarah isn’t kidding about keeping you as a girl, is she?”
“Um, it doesn’t look like it.” Roberta says as she turns to head back to the car.
“Hold it right there sissy. What did Sarah tell you to be?”
“Um, a good girl?”
“A good girl, who?”
“A good girl, sir?”
“Well, I don’t think you’re really trying to be a good girl, Roberta. What are you supposed to do when you answer a question from a superior?”
Roberta bobs quickly. “Curtsy, sir. I’m sooo sorry sir.”
“And you will be a little sorrier in a moment. I promised Sarah to discipline you if you were bad at all. Do you have a hairbrush?”
She bobs. “Yes, sir.”
“Then get it for me.”
She bobs. “Yes, sir.” Fetches her brush from her hand bag and hands it to Jack who turns her around and puts her arms on her vanity so she is bent well over. He places free hand in the small of Roberta’s back, and quickly places five stinging blows on the back of each of Roberta’s thighs, just below her shorts. She begins sobbing after the third blow and continues after the last. Jack pulls her to vertical and propels her into a corner where her sobs continue.
“You really are a sissy. Stay there, stare at that corner and think about how to be a good girl while I grab the rest of your stuff. Don’t touch those legs. Put your hands on your head. Stay that way.”
An hour later, Sarah has returned and, having learned of Roberta’s misbehavior, enters her room without knocking. Roberta is still in position with her hands on her head. She has long since stopped crying and her makeup is a mess. “So Roberta, Jack told me what a bad girl you were and how you gave him no choice but to discipline you. What do you have to say for yourself, young lady?”
Roberta tries to curtsy, but is prevented by the corner walls. “Um, I am so sorry ma’am. It makes me so upset to have this … person in our house and in our bed. And look what that bastard did to my legs.”
“Oh Roberta. You’re still not getting it. This ‘person,’ unlike you, is a man and he is my guest in my house and my bed. And like any man, he is your superior, and I specifically told you he was in charge of you. And don’t you dare call him that name. You know sissies never ever swear. As to your legs, you deserved that. The only thing wrong with them is that they’re probably redder than your bottom. Turn around. Now lower your shorts and shaper below your knees. Panties too. I was right. Your legs are much redder, but we’ll soon fix that.” And she does. “Now Roberta, let’s go tell Jack how really sorry you are that you were a bad girl and made him discipline you. Leave your shorts and undies as they are. We don’t want to spoil Jack’s view, do we? Well. Answer me sissy.”
Still sobbing, Roberta performs a painful little curtsy and manages to reply “Sniff….no..sob….ma’am…sob.”
They make their way to the library where Jack is sitting in Roberta’s former chair reading Roberta’s copy of the Economist. He looks up at the still crying sissy shuffling in with her chastity device on display. He can’t but laugh. “Tell him Roberta.”
She curtsies. “Mr. Jack, sir, sniff, I am sooo sorry I was a bad girl and made you, sniff, punish me. Sniff. I promise I will try my hardest to please you in the future. I really have, learned my lesson. Sir.”
“Turn around Roberta and show him how.”
She turns and he really laughs this time. “OK Roberta, I know you know this was for your own good, and to show you how kind Jack and I are, we will let you keep your shorts and things down to go to your room. Then you can change into something with a skirt before you come back to start dinner. Panties are up to you.”
In order to keep the pain in her buttocks and thighs to a minimum, Roberta steps out of her shorts and undies and carefully replaces them with a lacy white half slip and plaid pleated short skirt. She knows it makes her look a little like a school girl, what with the shoes and lacy socks, but it was quick and relatively painless. She fixes her makeup and does the best she can with her hair. She passes Sarah on her way to the kitchen and curtsies.
“Hold it Roberta. You did a nice job with your hair. Pretty soon you can skip your wigs. But, um, for now you should shave off those silly sideburns. Do it now.”
After dinner Sarah and Jack are snuggling in the library while Roberta cleans up. Jack is still wearing his business shirt, but, of course, nothing below the waist except his giant hard on. Roberta reports for further instructions, having waited for five minutes before being bidden to enter. She curtsies and stands in attendance.
“We hope you are feeling a little better after your discipline. Turn around and let us have a look. Bend over and lift those skirts. Oh, dear. You’re still awfully red. I can see why you skipped the panties. You can turn back now sweetie. Actually, while you’re here you can help us clear up a question. We have been wondering how your little thingy compares with Jack’s penis. Come over here and lift your skirt so Jack can remove your little device. Oh, I’ve given him the key for now. He thought it might make you more respectful.”
Jack removes Roberta’s chastity and chuckles at her little erection. He rises. It seems his penis is about ten inches above Roberta’s little thing. Roberta looks away, still holding her skirt.
“Well, we certainly can’t compare them that way. Roberta, step up on this foot stool. Here, hold my arm. I’ll help you stay balanced. Good. Now skirt back up. OK Jack, come here and let’s see how things measure up.” Sarah and Jack break into instant laughter. “This really is funny, Jack. I’ve got to get some pictures of this. Help Roberta keep her balance while I get my phone.” …. “Those close ups are a hoot! Now, you two, look at the camera and smile. I think I can get everything in. Roberta, move your skirt a bit to the right. Hold those smiles, just one more before Roberta’s little thing goes completely limp. Good! Roberta, hold on to Jack’s penis with your right hand, but keep your skirt up with your other hand. Now look at it and lick your lips. That’s cute. Now Jack, I can hold Roberta while you lock her back up, unless you think she deserves a treat.”
Jack laughs as he resecures Roberta. “Let’s see if she can be a good girl for at least a week first. OK?”
“Whatever you say. It’s your key. OK, Roberta. Step down.”
Roberta fixes supper, prepares the table, and finds Sarah and Jack in the library (knocking first, of course) , curtsies, and shyly raises her hand.
“Dinner is ready, Ma’am.”
“Thank you, sweetie. We will be right in.”
Roberta serves the couple, pours wine as bidden, and stands at the edge of the dining room awaiting orders.
She wriggles closer to Sarah and bobs, “Yes, Ma’am?”
“Well, tomorrow I suppose I’m going to have to let you dress up and pretend to be a man for work. But…Jack tells me he doesn’t much like the idea of seeing you dressed up like that, much less pretending to be a man. So I want you to be completely girly whenever he’s around. So tomorrow, wear a uniform to serve us in bed and help us get dressed. When Jack leaves, I will give you permission to get dressed up. Understand?’
“Good girl. You can clear these plates now, but see if Jack needs more wine first.”
The next day, having served Sarah and Jack, and Jack having left, Roberta is given permission to dress up in Robert’s outerwear to go to his job. She looks pretty much like the old Robert, notwithstanding her undies, butt plug, small studs in her pierced ears, and missing sideburns. Fortunately, there are several other guys at her level with long hair. She grabs her briefcase, finds Sarah, and curtsies. “Well Roberta, don’t you look butch.? OK, you can pretend to be a man as soon as you get to work, but not before. Understand, sissy?”
“Yes ma’am,” she curtsies.
It is a tiring day for Roberta. Acting like a man has not been as easy as she expected. She has to be careful about her walk and posture, not to mention her voice. And, she barely stopped herself from curtsying to her boss. Still, all this was better than her new home life, with Sarah so bossy, that creep Jack, and the constant fear of another spanking. Finally, Roberta is driving home in her much resented girly VW. Her new pink phone (she has to do something about that for work) rings. She can see it’s Sarah, so to be safe she uses her girly voice. Sarah gives her a short list of couple of things from the market. Finally, she comes in via the garage entrance. Carrying the shopping bag, she enters the kitchen and encounters Sarah who is pouring herself a glass of white wine. “God, Sarah, I could sure use one of those too. This has been…”
“Roberta,” she says condescendingly, “you really are a bimbo. You know better than to pretend to be a man without special permission, and your permission expired when you got into your car to come home, as it will every day. Like your permission to dress up will expire the moment you come through the door. Automatically. Then you forgot to curtsy. And I’m sure Jodie explained to you that sissies never drink alcohol.”
Roberta quickly puts the bag on the counter and bobs. “I am sooo sorry, ma’am. I won’t forget. I promise.”
“We’ll see. Run along and get properly dressed. You don’t want Jack to see you like this, do you?”
“No ma’am. May I be excused, please.”
“We will see you in twenty-five minutes.”
Roberta curtsies and minces off to her room. Sarah is amused by how girlish she is, even dressed like a man. Divested of her men’s things, Roberta races to meet her deadline. She makes sure her face is smooth and makeup perfect. Her girly earrings are reinserted. She has gotten better with her hair, so she can skip the wig. Already in shapewear, her uniform goes on easily followed by a fresh frilly apron. A spritz of her signature scent, and but for shoes and nail enamel, she is all girl again. She slides into her shiny heels. Donning her delicate gold watch, she discovers her time is almost up. Maybe her nails won’t be an issue. She finds Sarah sipping her wine in the library. Thank goodness that Jack is not back yet. She bobs and raises her hand, which Sarah ignores. From her seat, Sarah directs Roberta to turn around to be inspected. Roberta would have enjoyed this in the old days, but now it’s just more of Sarah’s excruciating control. “You wanted to say something, Sissy?”
“Yes, ma’am. I didn’t have time to do my nails. Shall I go back and do them before J…um…Mister Jack returns?”
“I’m not sure he’d really notice, but I think you have time, and I’m pleased that you’re being a good sissy by you being your girliest whenever you can. Run along and do those nails.”
As the week goes by, Roberta misses being Robert more and more. She would give anything to be unlocked and have sex with Sarah…on top. She hates never being anything but a submissive girl around his wife and that creepy Jack. She has been a perfect girl all week and has only been spanked once. Sarah must be getting a bit bored by now. She resolves to take it up with Sarah as soon as she gets home from work while she is still dressed as Robert. She finds Sarah and, sans curtsy, says in her Robert voice, “Please, Sarah, can we talk this over?”
“Really, Roberta, this is absolutely not how you are going to get to talk to me. And you’re still dressed up. Go change and report back when you are properly dressed. Oh, and from now on, I don’t ever want to see you when you’re dressed like this. From now on, if I am home before you, you will remove Robert’s clothes in the garage and then go straight to your girly room to change. Understand, sissy?”
Roberta, uniformed, made up, and manicured, curtsies to Sarah and delicately raises her hand.
“Oh all right Roberta, we might as well get this over with. What is it?”
“Please can we go back to the way we were. To me being Robert at home instead of Roberta. I am so tired of this.” She stamps her high heeled foot and her skirts rustle. “And I want to be here just with you, not that Jack. Please, please Sarah?”
Sarah sits in a stuffed chair, crosses her legs, takes a sip of her wine, and with a slight chuckle says, “Of course not, sissy.”
“Sarah? Roberta,” she says condescendingly, “fetch your handbag and report back here.”
This isn’t going well. Roberta scurries to her room and retrieves her shiny bag, the gift from Jodie and her husband. She approaches Sarah. To be safe, holding her bag in both hands, she does a little bob and looks down at Sarah.
“Take out your ball gag and put it on. … Good girl. Now, come closer and get on your knees. Now we will ‘talk this over’ for the last time. Things are not going back the way they were. Me being bossed around by a sissy is never going to happen again. And, you Roberta are a sissy. Your little movie proves it. I like things the way they are now. I’m rid of bossy Robert, and I have cute, little, obedient Roberta who is actually useful around this house, and I have an actual man around to do what men do. Get it through your sissy head that you are going to stay a girl for a very long time. Right?” Roberta nods. “Don’t you dare let me see you as anything else. I still love you, of course. Just in a different way. So just follow my rules and we’ll get along just fine. I will help you keep your little secret and even let you pretend to be a man at work, or family gatherings, or when we are with most of our friends.” Roberta looks obviously surprised when Sarah says “most.” She starts to raise her hand but remembers she is gagged. “Don’t worry Roberta, I only mean those friends who can keep a secret and might enjoy Roberta more than Robert. Then there’s my sister, Miranda. We never keep secrets from each other. In fact, she’s dying to meet you. She never got along with Robert and figures anything will be an improvement. And she loves the idea of being able to discipline you, so I know you will be on perfect behavior when she gets here tomorrow afternoon. So, that should complete this discussion until, and if, I decide there should be any changes. You may stand up, and if you are certain you can be a good girl, you may remove your gag and start supper. Oh, and Jack has a dinner meeting, so it will just be me.”
Miranda does indeed arrive. She is two years younger than Sarah, just as gorgeous, but red headed. She is wearing skinny jeans, a purple sweater, and purple ankle boots. Jack, fully dressed at the moment, has carried her bags to the guest room. He rejoins the sisters in the library. Sarah gestures for him to kneel before them, which he does. Sarah has never felt so empowered and is getting a rush showing off to her younger sister. Miranda had always been the more dominant one in the past. “So Mandy, what do you think of my boy here?” she says, patting him on the head. Miranda smiles and whistles. Jack is indeed a hunk of a man, however Sarah chooses to address him. “Well wait ‘til you see this. Stand up, boy. Now drop ‘em so Mandy can see your package. Ta Da!”
“Wow! You weren’t kidding. No wonder you keep him around. May I touch?”
“Of course. Sisters always share, don’t they?”
She fondles his penis, which quickly becomes erect. “Oh my gosh!” She keeps her hand around the massive thing. “I never saw Robert’s, but I can’t imagine it would be anything like this.”
Jack snickers and Sarah laughs out loud. “I’ll have to show you some pictures later. They’re sooo funny.”
“Speaking of Robert, where is he? I’m dying to see the improved version.”
“First of all, we don’t have Robert around here anymore. We just have my sissy, Roberta, who is now fully in touch with her feminine self. She’s probably doing the ironing. I’ll ring for her.” She rings one of the little bells that are kept in most rooms to summon Roberta. “I let her wear her pants for your first visit. Jack thought it would be nice, since they’re her only pair. I’m sorry. I don’t know what’s keeping that girl. Roberta! That’s it! Boy, pull your pants up and go find Roberta, please.”
Roberta, of course, has had a bit of a panic attack, and is hiding behind the door in the laundry room. Jack finds her in no time. He grabs her arm and grins. “Tsk, tsk. I’ll bet you’re in for it now, sissy.”
Even Jack must knock before opening a closed door. After doing so, he pulls Roberta into the library before the seated sisters. Roberta tries to turn away, but Jack, standing behind her, holds her arms so Miranda can see her in full sissy regalia: shiny shoes, lacy socks, smooth legs, shorts so flat in front, frilly blouse, and beribboned hair band…full make up, coordinating pink nails, and sparkling earrings. She is blushing like never before. She is almost in tears. Miranda is doing her best to keep from laughing. Sarah is furious, but keeps her cool for now. “Roberta, where are your manners?”
Roberta quickly curtsies. She is starting to tear a little. “I am sooo sorry ma’am.”
“We’ll see about that when you are back in a dress. For now, why don’t you turn around slowly, so Miranda can get a look at the new you?”
As Roberta turns, Miranda can restrain herself no longer and breaks into laughter. When Roberta stops, Miranda gets up for a closer inspection. “Oh my god. You make a perfect sissy! You’d make a perfect girl too. How often does Roberta dress this way?”
“We if you mean in this outfit, hardly ever. It’s her most masculine, so she hardly ever gets to wear it. She is usually in skirts or dresses or, of course, her uniforms.”
“Someone has to be the maid around here.”
“I thought you were kidding about that.”
“Hardly. Roberta, tell Mandy what you are.”
Roberta looks at her shiny shoes and lacy socks. “Um, I am the maid here.”
“Wow Sarah! A male maid.”
“Not quite. Roberta’s not a man….ever. Tell Mandy what you are, Roberta.”
Still staring at her feet, “Um, I’m a sissy….a girl, ma’am.”
“I can’t believe this. My brother in law wants to be a girl. You want to dress like this and be a servant to Sarah?”
“It doesn’t matter what she wants. She’s a sissy now, and if I want her to be a girl she has no choice but to be a girl. And, as you can see, she is. Of course she’s a servant to me…and to Jack and you for that matter. It’s what I want. She never pretends to be anything else here. Like I think I told you, I let her pretend to be a man for work, but I never have to see that.”
“Roberta, is this all true?”
“Cool. Sarah, I think this is going to be an interesting stay. When does she go back to being a maid?”
“Why, right now. Run along and get changed, sissy.”
Roberta returns wearing a starched pink day uniform. The skirt flares a bit by virtue of a parchment slip which rustles audibly. Her white starched apron is ruffled along the hem and on either side of the bib which sports Sarah’s monogram. Sarah and Miranda are laughing as Sarah scrolls through the camera roll on her phone. “Roberta, before drinks, I think there is time for you to help Miranda get settled. Jack has put her cases in her room. Help her unpack and see if she has anything to be laundered or ironed.”
“Thanks Roberta, I think it’s just those two blouses that need ironing. You know, I still can’t get over what a total girl you’ve turned into. No one would ever guess you were anything else. I can’t imagine any kind of a man making himself all pretty and then being a servant to his wife and her lover. Although,” she giggles “Sarah showed me those cute photos of you and Jack, so I understand now why she likes this arrangement. But you? I guess you must really love this and secretly wanted to do it all along.”
Roberta delicately raises her hand. Miranda acknowledges her with a nod. Roberta gives a little bob and says, “No ma’am. Absolutely not. We were just having a little fun at a club. It was our first time there. That Jack put some moves on Sarah …mistress, and somehow I was like kidnapped by this horrible woman and her husband. They did horrible things to me. They called it sissy training and said it was all for my own good. They made me talk like this and gave me all kinds of rules. When they got through, I was pretty much like this,” Roberta holds her skirt out and does a little bob. “I was shocked when Sa.. mistress picked me up. She had completely changed. She made me stay this way and kept that awful Jack. The only time I can dress like a man is for my job. They keep me locked up under my panties. They both discipline me all the time. I think they think it’s fun. Mistress threatens to leave me and embarrass me to everybody, or, worse, to send me back to those people for a refresher course. I just don’t know what to do, ma’am.” She sniffles and does a quick bob.
“I don’t know what to tell you Roberta, this is all pretty new to me. I never really hated you, even though you were often such a twit. Maybe Sarah will get bored with this and let you go back to being more of a man. For now, it just looks like you’re going to have to go with it and be a good girl. I’ll try to help you when I can. Here, let me fix this smudge on your eyeliner. I did get you out of making dinner. I’m taking Sarah and Jack out after drinks. Oh, I would appreciate having that white blouse for tomorrow, sweetie.”
After drinks they are about to leave and Sarah has given Roberta her final instructions. “One more thing, Roberta. Jack told me about your trying to hide in your room, before. You know that was bad. Get your hair brush and we’ll take care of this before we leave.”
Jack is given the honors, Miranda having declined, and Roberta is soon crying, hands on the entranceway table, panties down, and skirts tucked up. “Lights out for you at 8:30, sissy.”
“Yes, ma’am.” Sniff.
On Monday, Jack and Sarah have left, and Roberta has removed her cosmetics and fingernail enamel. She has switched to her smallest earrings and given her hair its most masculine style. Outside of her lingerie and corset she is wearing Robert’s clothes. She looks like a man. She is swishing down the hallway toward the garage in her most girly gait when Miranda rounds the far corner. She wiggles closer to Miranda, then stops, bobs a respectful curtsey, and in her girly voice says “Good morning, Miss Miranda.”
Miranda giggles. “My god, Roberta. You tell me how much you want to be a man, but you’re acting like a total girl even though you’re dressed like a man.”
“I’m sorry, ma’am,” she bobs again, “Mistress says I’m not allowed to act like a man….pretend to be a man she says, until I get out of my car at work, and I have to be a girl again as soon as I start to drive home. I can never pretend to be a man around her. I’m not even allowed to be seen by her when I’m dressed up like a man.”
“I still can’t believe you take all this shit. I’m still not sure you don’t sort of like this…that you really are a sissy. I mean, Sarah and Jack are gone. Maybe I’ll give you permission to act like a man. Would you like that Roberta?”
She bobs, “I would adore that, Ma’am.”
“Actually, just to be safe, why don’t I call Sarah and ask her.” She dials her sister and waits. “Sarah? I’m here with Roberta, and we were wondering if I could give her permission to act like a man for a few minutes before she leaves for work. No she didn’t put me up to this. It was my idea. What do you say?…..OK. See you later sis. Sorry, Roberta. She said no dice and that you were lucky she let you do that at work. She said she was thinking about having a chat with your boss…I seem to recall that the two of them are kind of chummy. I’m sorry sweetie, I hope I haven’t made things worse for you. Although…maybe it would be easier for you not to have to switch back and forth all the time. Would you just as soon be a girl all the time?”
“Oh, pleathe, no ma’am,” she bobs.
Later that evening, Roberta having been dismissed to go to her room and Jack out, the sisters catch up. “So, Sarah, it seems Robert isn’t exactly living his dream.”
“Miranda, it’s Roberta and it’s ‘her.’ I honestly don’t care whether it’s her dream or not. She’s going to stay Roberta for the foreseeable future.”
“Don’t you think this is just a little bit cruel? I never much liked Robert, but you treat Roberta like a slave, and I think Jack gets off tanning her bottom. It’s constantly red.”
“I know Jack gets a little carried away. I think he is a little jealous of who Roberta used to be, but a little discipline isn’t going to kill her, and I don’t think she has nearly reached her potential as a servant. In fact, I’m looking into sending her to back to school to learn how to do hair and nails. She’s getting pretty good with nails as it is. You should have her do yours instead of going to that salon.”
Miranda looks at her nails. “You know, I really could use a fresh manicure. It’s too bad Roberta’s gone to bed.”
“Not a problem, sis.” She rings Roberta’s bell, and a few minutes later, a sleepy looking Roberta appears in her frilly pink baby doll and curtseys to the ladies. “Sorry to keep you from your beauty sleep, Roberta, but Miranda could use a mani-pedi. So be a good girl and go get your kit. Oh and fix your make up, but you can stay in your nighty.”
A week later, Sarah and Miranda enjoying an after dinner glass of wine in the library. Roberta is standing facing the corner, skirt up, panties down, sniffling after ten swats of Sarah’s hairbrush.
“Miranda, I know you didn’t think her dinner service was all that bad, but it wasn’t perfect either. Besides, to be perfectly honest, I’ve come to enjoy disciplining her. You’ll notice I can get her crying in less than five swats now. Jack can do it in two, though. You’re really going to have to learn how to do it, too, for when you’re in charge of her while Jack and I take that short break. I don’t want any backsliding. So tomorrow, after she serves breakfast I want you to practice on her. I’m sure you’ll pick it up in no time. Roberta! Stop that sniveling. You know this is for your own good.”
Time flies when you are having fun, so the next few weeks went slowly for Roberta, and Miranda is back for another visit and is chatting with her sister as Roberta, properly dressed after her day as Robert, steps just inside the library and poses silently waiting to be noticed, and curtsies when she is. She resumes her pose and awaits instructions.
“So, Sarah, was Roberta a good girl while I’ve been away?”
“Pretty good. She’s only had two really serious spankings.”
“Oh. What were those for?”
“Tell her Roberta.”
Roberta steps a little closer and curtsies. “I, um, complained that it was tedious for me to undo my make up and nails to dress up like a man and then to redo them afterwards. Ma’am. Sorry.”
“You know Roberta. I’ve been thinking about your little problem. Tell me sissy, in Robert’s job, is there any contact with clients or the outside world?”
“And do we socialize with anyone at all from there?”
“Just Bill Jones from time to time, mostly because he’s the boss. I also have lunch with some of the guys, but none of us is really close. Ma’am.”
“So Robert’s job has virtually nothing to do with the rest of our lives except the paycheck and keeping the boss happy.”
“Well, sissy, a girl like you may not have noticed, but Bill has had rather a thing for me for quite some time. While he’s no Jack “down there” he can be entertaining. We’ve gotten pretty open with one another, and he’s so smart, so I mentioned how you’ve become a sissy girl and how I really prefer you this way. He was very understanding. He said being a sissy was clearly not affecting your performance, and your being a sissy was fine with him. You would never guess it at work. So I showed him a few of your cute pictures. He was actually impressed. I’m afraid I also showed him some of your little movie, since I knew he had a bit of a kinky side, too. I just showed him the very first part, where you and your lover were making out. He really couldn’t get over what a girl you are.
So, getting back to your little complaints about changing in and out of dressing like a man, I came up with a brilliant way to help you. Guess what I did?”
“What, Ma’am?” she bobs, fearing anything that would make Sarah grin like she was.
“Welll, sissy, I asked Bill if it might be ok for you to go to work as you really are. As Roberta. And guess what he said?”
Roberta’s mouth is wide open. “Oh..oh…..no….please.” Though still dazed, she remembers to say “Ma’am” and curtsy.
“Don’t tell me he said ‘yes?’” Mandy interjects.
“Well, he thought about it a while, and then said he supposed so, as long as Roberta was really girly in real life. Well, we already know the answer to that, don’t we? He said he’d better see for himself, first. So, I’ve invited him to dinner here tomorrow to see Roberta in action. You will be a perfect girl, won’t you Roberta?”
Roberta starts to tear. She grips her skirt to regain composure. “Please………Ma’am.” She sniffs.
“That’s a yes or no question, sissy.”
Roberta looks down at the toes of her shiny pumps, and swallows. She breathes deeply. “Um….yes……ma’am.”
“Really, Roberta. I go to all this trouble and I don’t even get a thank you? Really. Turn around right now so Mandy can give you a couple of swats then go to your corner to contemplate what a perfect girl you’re going to be for Mr. Jones, as you should always address him from now on.”
As Roberta waits in her corner, bottom stinging from Mandy’s now well developed skills, she overhears the sisters’ continued conversation.
“Wow, Sarah, are you sure this is a good idea? Having her out in public like that?”
“Why not? It’s not like those work people have anything to do with the friends and relatives who think Roberta might be a man. And, I’m really sick and tired of her complaining and sour looks. We just have to make sure she makes a good impression on Bill. To that end, I made an appointment for her at the salon tomorrow. I think it’s time for her to have a proper hairstyle, maybe some work on her brows, and nail extensions. Oh, and maybe some waxing down below; I told them to leave just a little landing strip. I made an appointment for you too for hair and nails, so you can babysit her. Remind me to give you her key so they can do the waxing.”
“Why the waxing? I’m sure Bill won’t be looking down there.”
“I know, but Jack came up with the idea when I told him my plan. Might as well, since she’s going to be there anyway.”
“You know, Sarah, if you do all that other stuff, it’s going to be awfully hard to dress up like a man in a hurry. What if Bill doesn’t approve? How could she go to work on Monday?”
“All the more reason for Roberta to try her hardest. Get it Roberta?….Roberta!”
“Yes Ma’am,” she says into the corner.
“You know Sarah, I have a feeling today will have been the last time Roberta will have dressed up like a man for a very long time.” Sarah just laughs.
The next morning, after serving breakfast, Roberta is allowed to change into her above the knee gray flannel skirt and pink nylon back buttoned blouse and a slightly darker pink one-button jacket. Her one inch belt, large pocketbook, and two-inch pumps are coordinating black patent. Hoop earrings, a charm bracelet, and a little gold watch; perfect makeup and nails, a spray of her signature scent, and except for her hair, she’s a girl ready to go. Mandy helps her with her blondish wig…a little lighter than her natural hair which still maintained a somewhat masculine cut. “You won’t really be needing this much after today, sissy. So let’s go keep our appointments. Then Sarah wants us to do a little shopping. Also, some good news, you won’t have to curtsey or need permission to speak. And, you can call me Mandy. Sarah wants you to be a perfect girl today…and of course tonight.”
On the way to the salon Roberta asks “Um, Mandy, do you think there is any chance of my getting a style that could be turned into something a guy could wear? I can’t bear the thought of being stuck as a girl.”
“Oh, Roberta, that wouldn’t be so bad. I mean, I’m stuck as a girl, and I rather like it. I’m just kidding you, sissy. I have no idea what Sarah has arranged for you. I wasn’t with her when she called the salon, and when I asked her what you were getting, she said you deserved a nice surprise.”
“Mandy, I can’t imagine Sarah giving me a ‘nice surprise’ these days, and I can’t think of anything much crueler than trying to make me go to work as a girl. I didn’t sleep a wink last night. I am simply terrified.”
“I understand, and I do feel sorry for you sweetie. I never knew Sarah could be this way. For your sake I actually hope she is just playing with you, and Bill really isn’t coming to dinner, but I really don’t know. I do know she was serious about the waxing, though. She gave me your key and strict instructions that your hands not get anywhere near there. Anyway, aren’t you a little excited about your first salon visit? I still adore being pampered even though I go all the time.”
“I suppose I might like a little pampering after all the abuse I’ve been taking, but I’m really worried about what they’re going to do with my hair and I have a feeling the waxing will be painful..not to mention embarrassing.”
“Good morning girls and welcome to Golden Shears. It’s great to see you again Mandy, and you must be Roberta. Sarah sure wasn’t kidding when she said you’d become quite the sissy. I can promise you that when you leave here today you will be quite the girl. Sarah has told us exactly what you want, so why don’t you girls change into smocks and we’ll get going on your hair. I’ll take you Mandy, and we’ll give you, Roberta, to Mr. James, he’s really the star here.”
Smocked, seated and wig removed, Roberta looks up at her hairdresser. He looks quite like Mr. Big from Sex in the City, but he is flamboyantly gay. “Um, Mister James, sir, what do you plan on doing with my hair?”
“Don’t you worry your pretty little head, Miss Roberta, Sarah has told me exactly what you want. You won’t need that silly wig again. You will look like a princess, just like you’ve always dreamed.”
Roberta whispers, so Mandy can’t hear, “Please Mr. James, I don’t really want to be a princess. Could you please make my hair so I can comb it like a man, sometimes? Please?”
He laughs. “Sarah said you might say something silly like that. Why would a girly like you want to look butch?”
“Because I really am a man, sir.” She whispers.
“Not any more, according to Sarah. I’ll tell you what, Miss Roberta, let’s save this discussion ‘til later. Maybe I’ll pop in during your waxing. Now, just relax, sissy.”
It seemed forever, but finally Mr. James pronounced Roberta to be ready except for removal of her curlers and her blow out. She has no idea at all what Mr. James has done. “You know Roberta, for your first visit you’ve been a very patient girl. Now let’s get you over to Suzy for your waxing.”
“Is this your first waxing, honey?” Roberta nods, very apprehensive to say the least. “Well, today we’re just doing your hands and arms and a Brazilian with a little landing strip. Let’s get you set up here. Mandy gave me your key. Don’t be embarrassed honey, I’ve seen everything. Spread those legs and we’ll lift that smock. OMG Sarah was right. You really are tiny. Now keep your hands and arms up. Sarah said no touching for you. First we will do some trimming and now remove your device. Oh, look, you’re swelling. How cute. It actually makes the job easier. Doesn’t that warm wax feel good? ….there, nice and cool and ready to go…”
Mr. James rushes in. “You girls OK?” Roberta is in tears and reaches down to rub her stinging nethers.
Suzie slaps her hands away. “You know what Sarah said! No touching. James, do you think you hold her hands away until I finish? She’s being a bit of a sissy about this.”
“Of course, that’s what she is. I’ve seen a lot cock in my time, but hardly any as tiny as Roberta. No wonder Sarah thinks she’s better off as a girl. You’re doing an amazing job Suzie. I’ve never seen such a dainty strip. Why don’t you take a photo for Sarah before you lock her back up? Hold a mirror up so she can see too.” Roberta just sniffles. “Don’t forget her eye brows.”
Later, Roberta looks down at her hairless arms and hands as the nail tech completes the extensions. They’re not quite half an inch, but even with pink pearl polish, she could never get by with them dressed like a man. Then, at last, Mr. James removes her curlers and blows out her hair. It is worse than she feared. She now sports a light brown wedge bob with long bangs cut straight across her forehead. Lots of blond highlights complete the look. Her eyebrows are thin and arched. Her nails are now the least of her worries; she will need a wig to dress like a man.
Mandy texts a couple of pics to Sarah, who promptly rings back with facetime and asks for Mr. James who is modest in the face of what seems Sarah’s effusive praise. He then hands the phone to Roberta who listens wide eyed, blushes, says “Um, yes, ma’am,” and returns the phone to Mandy. Roberta slowly moves to Mr. James and looks up to his smiling face. “Mr. James, sir, thank you helping make my girly dreams come true. My I please give you a kiss?”
“Of course, honey,” he grins. “Put your arms around my neck.”
Roberta reaches up and the much larger man grabs her around her waist, lifts her almost off her toes, and begins a French kiss that lasts the better part of a minute, and finally returns the now breathless sissy to her feet. She is tearing a bit from embarrassment. Except for Mandy, the others applaud. Roberta looks for her lipstick to make the obvious repairs.
Mandy and Roberta pay the bill, and Mandy gives Roberta the money for tips. Finally, they set off for some shopping. “Well, Roberta, at least you have never looked so good.”
“Thanks a lot, Mandy. That was so, soooo humiliating. That awful waxing, and look at my hair. I don’t know how I’ll ever be a man again. Then that kiss! Yuck!”
“I know, Roberta, but I’m afraid you’re just going to have to suck it up. From the looks of what Sarah just had them do to you, she is serious about you working as Roberta. I suppose that’s why we’re going shopping now for some skirts and dresses appropriate for your job…and shoes, of course.”
“Oh Mandy. You’ve just got to help me. Please. Can’t you call Sarah before this goes any farther and tell her to stop. That it’s just not fair. Things have been bad enough ‘til now, but to be seen by my boss like this…much less go to work! How can she be so cruel? I’m her husband, after all.” Sniff.
“To be honest, Roberta. I agree with you, and I had a long talk with Sarah last night, and I thought I had gotten somewhere, although I think she’s on a bit of a power trip, having Jack around and keeping you like a sissy. I had no idea what sort of hair style you’d be getting. I sort of figured the waxing might be enough for her, and no one would see your landing strip. But that hair style was no accident. She obviously didn’t listen to me, and making you kiss Mr. James really was cruel. I’m sorry sweetie, I’ll keep trying, but for now I don’t know what to do except for what Sarah wants. Please don’t cry Roberta. Let’s just go and get the shopping over with.”
The girls return home with everything on their list, and then some. Jack and Sarah were waiting. They both break out laughing at the sight of truly feminized Roberta. Jack chortles, “I’d like to see her try to dress up like a man now, Honey. Say Roberta, did they give you that landing strip like I asked?” Roberta closes her eyes and slowly nods yes. “Then show us, sissy.” Roberta stays motionless. “Move it sissy!” Jack threatens.
“Jack,” Sarah scolds, “Roberta has had a very long day. You have no idea what the girl had to go through to get that marvelous hair style, and I’m certain you’ve never been waxed. Still, Roberta honey, I do want to see if the photos do you justice. Please lower your panties and lift your skirt so we can see.” Slowly, Roberta does so, to Jack’s laughter. “Jack!” Sarah says sharply, “be careful or you’ll end up with one of those too. You may lower your skirt now. I’m impressed Roberta. They colored it to match your hair.”
After helping the girls bring in Robert’s purchases, Jack is sent away for the evening. Sarah doesn’t want anything to interfere with Roberta making a good impression on Bill Jones. Sarah has decided that after preparing dinner Roberta will change out of her maid’s uniform and into one of her new work outfits for Bill’s arrival. Bill has also asked to bring his wife along for a second opinion on Roberta’s suitability.
Roberta waits nervously in the library. Her work outfit consists of a dark gray below the knee skirt with a very full cut that lets it swing when she walks, a long sleeve white cotton blouse with pearl back buttons and a peter pan collar with lacy embroidery. Her four inch black patent belt is matched by her medium height pumps and of course by her large pocket book. At hand is her little black pocketless jacket that barely covered her belt. Jewelry was minimal: gold hoop earrings, a gold ladies Rolex lent by Sarah, and several gold bangles on each arm to remind her to keep her arms up. She didn’t look like a secretary, but she certainly wasn’t an executive either. Finally, the dreaded bell rings. Sarah stands, and she looks down on the fidgeting Roberta. “I’ll spare you answering the door. Why don’t you go to the kitchen and check on dinner. Stay there until I call you. Stop fidgeting!”
Opening the door, Sarah greets the Joneses, Bill and Holly. “Great to see you two! Let’s go into the library and get you something to drink. I really can’t thank you for considering this. I think it might mean more to me than Roberta. I am so much fonder of her than I ever was of Robert. Oh, and my sister Mandy, she will be joining us in a little while, likes her this way, too.”
“When will we get to meet this new Robert?”
“She’s just in the kitchen, Bill. Roberta! Mr. and Mrs. Jones are here. Come and introduce yourself. I had her wear one of her new work outfits. Let us know if you think it sets the right tone.”
The Joneses watch in amazement as they see Roberta mincing in the hallway from the kitchen. Her heels click on the hardwood floor. Roberta pauses just inside the door, takes a deep breath, puts her right hand on her hip. Her left hand is higher than her elbow, keeping her bracelets in place. “Good evening,” she says in her best feminine voice. “I can’t thank you enough for giving me a chance to live my dream.”
“My god Sarah, I really didn’t believe you when you told me about Roberta. I thought this was just a practical joke, but jeeze, he looks nothing like a man….”
“Roberta, why don’t you do a very slow twirl, so they can get a better look. Don’t you think her hair is an improvement, too? She spent most of the day at the salon to impress you tonight.”
“I thought that was a wig.”
“Of course not, Bill. Come a little closer Roberta, so they can get a better look. Now, walk down to the kitchen and come back. Show us how daintily you can do that.” Roberta does just that, her skirts swishing back and forth. “Good girl, Roberta. Why don’t you sit and join us until Mandy gets back.” Roberta gracefully seats herself and crosses her legs. “Well, what do you think?”
“So far I’d never guess he was ever a man. I can’t believe this is Robert who was in the office just yesterday.”
“Well, this does show what a day at a good salon can do. But we’re both determined that Roberta is going to be all the girl she can be. No more pants for her. Right, sweetie?”
“Um, yes, ma’am.”
“Well, Holly, when I learned Roberta was really such a sissy, it just seemed right to change our relationship. The only one in this family who wears pants is me, and, as head of the house, I get the respect from Roberta that I should. And, Roberta has actually become helpful around the house. In fact, she made dinner for us tonight. Tell us the menu, sweetie.”
Roberta recites the bill of fare, and as she is finishing, Mandy arrives.
“Mandy, you remember Bill and Holly..”
“Of course. It’s great to see you two again. I peeked into the kitchen, I think we’re in for a great supper. Roberta’s become queen of the kitchen.”
Roberta blushes and gracefully rises. “Excuse me please, dinner should be ready in about ten minutes.”
“You should wear one of your aprons, sissy. Protect those work clothes!”
Roberta wriggles toward the kitchen, and Holly says “I can’t believe that walk. And aprons? It sounds like she’s a maid!”
“Well, sometimes she helps out a bit like a maid, doesn’t she, Mandy?”
“That she does, Sarah. She may be planning to do that tonight. I noticed the table was only set for four.”
“That’s probably because of her diet….easier just not to sit down. Maybe I’ll go see how she’s doing. I’ll be right back.”
Shortly after Sarah rejoins the group, Roberta reenters and waits to be noticed, her folded hands resting on the skirt of her bib apron. There are ruffles at the bottom of the skirt and along the bodice. It is obviously a maid’s apron, and Roberta’s name is embroidered on it in fancy script. There is a lull in the conversation. Roberta softly announces, “Dinner is ready, Ma’am.” Roberta turns and wriggles toward the dining room, the large bow of her apron sash swinging as she goes.
“Gosh,” says Holly, “she certainly walks like a girl doesn’t she?”
“It’s like I told Bill, we are all serious about her being a girl. We have been helping her practice almost every day since we got back from vacation. That was when I first learned how much of a sissy she really was. She still hasn’t reached her full potential, but I really do think she is ready to go to work as she really is. I hope you two agree.”
“Let’s discuss a little more over dinner. I never knew Robert….Roberta could even cook.”
The table really is set for four. Roberta has already poured the wine and water and set the first course. She stands in attendance by the sideboard.
“Roberta! This is delicious.” Holly praises. “ But why aren’t you sitting with us? And you look almost like a maid in that apron.”
“Oh no, m.., Holly. It’s just that I’m on a diet, and I just know if I sit, I’ll eat. This way I can make sure dinner is perfect. And the apron is just to protect my new clothes.”
At this point, Sarah points to her wine glass, and Roberta almost jumps to refill it. She freshens those of the others as well. “Maybe you can join us for a glass of wine, then, Roberta?”
“Um, no, I can’t. But thanks.”
“Why can’t you? Oh. Your diet?’
“Tell her why, Roberta.” Instructs Sarah.
“Um…..sissies never drink alcohol.”
“Let me explain, Holly. Robert could get pretty silly when he had too much to drink. And having a sissy for a spouse could be embarrassing. But we do love each other, so when I learned what a sissy Roberta was, I decided she had better have some rules to protect me from being embarrassed. One of them is “no alcohol.”
“Are there more?”
“More than you’d think, but Roberta has them pretty well memorized. Probably most important is that when she is Roberta she must be a perfect girl at all times, and, with very few exceptions, she must be Roberta whenever she is around me.”
“Is that what Robert wanted, too.”
“Perhaps not, but it doesn’t matter. She’s the sissy. I make the rules. She follows them. So except at work, Roberta has been Roberta 24/7. I’m sure she’ll say she likes dressing up like a man for work and pretending she’s not a sissy. But I’m sure at some point someone would have noticed her nails or her shapewear or some other girly detail. Then you would have had one of those situations with everyone talking behind her back. Also, this pretending to be a man is hardly helping her progress as a girl. Hardly a day goes by without some little slip up. So I’ve decided it’s best for Roberta to be a girl all the time. If she looked or acted like a man in a dress, I can understand how you might have a problem letting her come to work. But, as I’m sure you’ll agree, my sissy seems to be all girl. I can’t imagine anyone being uncomfortable with her after the initial surprise. I’m sure they’ll treat her like any other girl. Besides, how can she dress up like a man with her new hairstyle and pretty nails. I’m not about to let her get rid of either. So really Bill, this is the only way to keep what you tell me is a valuable employee.”
“I’ve been giving this serious thought, and I’m afraid I have to agree with you. I think it would be best if worked from home for a few days this week, so I can get with HR and break the news to the staff about our new girl. Are you sure you are up to this Roberta? You’re certainly not going to be having lunch with the guys for a while.”
Grasping the hem of her apron so tightly her knuckles whitened, and almost in tears, Roberta is speechless. Somehow, she never really believed Sarah would do this to her. Stifling a sob, Roberta turns and swishes out of the room.
“Will you all excuse me a moment. I can’t imagine Roberta is anything but excited.”
In no time Roberta’s bottom is burning and her regret at having left the room is most sincere. Sarah gently pats the almost glowing orbs. “So sissy, once you’ve calmed down, you will fix your makeup and come back and tell Bill just how really grateful you are. Right?”
“Yes, ma’am,” Roberta barely manages through her sobs.
Back in the dining room, Sara confirms, “I was right, she really is happy to do what I want and to do whatever it takes to be Roberta at work. She’ll be back in a few minutes to take your coffee and tea orders. And Bill, thanks very much for helping us out!”
“I’m sure it will all work out. But tell me Sarah, won’t having Roberta as a girl full time be a little difficult for you from time to time when you need a man for something?”
“Not really, Bill. I mean, when I found out Roberta was a sissy, we agreed that I could have a more ‘open’ marriage, for any such occasions. As Mandy can tell you, I have at least one guy who’s at least as macho as you.”
“I see. What about Roberta? Does she see anybody else?”
“Of course not!” Sarah laughs. “She’s a sissy, but she’s not into men, although I’m sure there are guys out there who would enjoy Roberta ‘just the way she is,’ if you know what I mean.” And they all laugh.
As Roberta serves coffee, Holly asks “Are you really sure about this Roberta? I mean, after the first day looking like you do, I don’t see how you could ever turn back.”
“Of course she’s sure! Roberta, tell Holly and Bill how much you want to be a girl and for everyone to know, so you don’t have to hide what a sissy you are…now.”
“Um…I’m sure…..I really do want to be a girl…..”
“Uh…for everyone to know…”
“To, like, know that I, I, I am a …sissy.”
“Good girl! Now, don’t you feel better?”
“Good. Now that that’s settled, you can start clearing the table, Roberta.”
“Bill, is Roberta’s PA still Jenny Johnson? The one who thought Robert was too bossy?”
“Yeah, why do you ask?”
“I’m thinking she may be a help with Roberta’s development. Please let me know when you’ve told her about my sissy. I’d like to take her to lunch for a little girl talk.”
Roberta in the kitchen, Holly asks “Sarah, are you really sure Robert really wants this? Come out in front of the entire office? I still think I detected a little hesitancy. I’m not sure if this isn’t a little cruel. You’re basically taking away all masculinity.”
“Look Holly. First of all, it’s Roberta, not Robert. And I honestly don’t care if she ‘really’ wants this. I want this. I makes me happy to have my sissy be the girl she is now. No more silly masculinity….no masculinity whatsoever. I’m serious about this. She’s either going to continue her job as Roberta or I’ll send her in to submit her resignation as Roberta. I’m sure it may be a little embarrassing either way, but I think that just comes with the territory of being a sissy. Just let me know when you want her to start.”
“I give up Sarah. I’ll call you as soon as we’re ready.”
“By the way, Bill, I trust outfits like what she’s wearing tonight are appropriate?”
“Yeah, but without the apron please.” He laughs.
The next morning, a perfectly miserable Roberta boxes all of Robert’s remaining clothes and on the verge of tears watches as Jack removes the boxes to god knows where. She asked where, and Jack told her it was really none of her business. “Don’t look so sad, sissy,” Jack sneered, “you still have one last pair of pants…those cute little shorts. As I recall, they zip up the back and don’t have any pockets, but they technically are pants, right?” He laughs and Roberta tears up, fully realizing her situation. Jack pauses and reaches into his pocket. “Oh, cheer up sissy. If you’re a really good girl all week, we may just release your little thingy.” And he slowly passes the key past Roberta’s tear filled eyes. “So let me see a big girly smile, or we may have to add another week.” He lifts Roberta’s face up by her chin and is slowly given her prettiest smile….under the circumstances. “Much better, sissy. Now what do you say to me for helping you get rid of all this useless stuff?”
Holding her smile, she curtsies and says, “Thank you sir for helping me get rid of … that stuff.”
Jack looks down and grins. “My pleasure, little lady.”
Later that day, after amusing himself by having Roberta wear her sissy shorts outfit, Jack has gone home, and Sarah and Mandy are enjoying after dinner coffee in the library. Roberta quietly enters and waits to be noticed. Looking up, Sarah inquires whether the kitchen is clean. With a quick bob, Roberta responds, “Yes, ma’am.”
“Then you are dismissed.”
Roberta stays put and delicately raises her hand.
Almost in tears again, Roberta whines, “Pleeeese, Sarah. Please don’t make me go to the office like this. I have tried so hard to be a good sissy for you all the rest of the time. It’s not too late. I’m sure Bill hasn’t told everyone yet. Pleeese make Jack bring back my clothes. I’m sure I can get a wig or something to cover my hair. Pleeeeese let me be a man again….at least at work.” With tears in her eyes, she kneels before her wife.
Sarah is silent. Finally, she says “All right Roberta, why don’t you get up, go change back into your uniform, then come back and we will discuss this.”
“Oh! Thank you sooo much, Sarah!” and she rises.
“Sorry, ma’am, sorry, sorry.”
“Just run along, Roberta.”
Roberta having wriggled out of the room, Mandy asks “Are you really thinking of letting Roberta be a man at work?”
“Not really. We all know she’s not really a man anyway. I just think it’s better for her to be in a dress when she’s told. Just in case she needs discipline.”
A bit later, Roberta returns in one of her most feminine uniforms in hopes of getting on Sarah’s better side. She curtsies and waits to be recognized. Nervous as can be, she fidgets with her hands in front of her apron, as Sarah makes her wait what seems like forever. “Roberta, stop doing that with your hands.”
“Yes, Ma’am,” she curtsies.
“Keep your hands on your skirts like they are, but you may stand for our conversation.”
Roberta feels vulnerable indeed. Standing in the middle of the room. One knee daintily across the other. Her hands and arms well out to her sides. The grasping of her skirts is a constant reminder that she’s wearing one and emphasizes her protruding breasts. Still, she has got to convince Sarah to change her mind or she will explode with anxiety. Sarah makes Roberta wait a bit longer as she slowly makes herself more comfortable in her chair.
She finally says, “Now Roberta, what is it you want to talk about?”
“Um. Sar….Ma’am. Ma’am. Sorry.” A quick bob, hands still in place. “Um…Pleeeese could I keep working as a man?”
“Of course not, silly girl. That would be impossible. You’re not a man, are you Roberta? Tell us what you are.”
Squeezing her hands tightly she utters, “A sissy. Ma’am.”
“Really more of a sissy girl, wouldn’t you say?”
In frustration, she moves her arms and causes her dreaded skirts to rustle and remind her again she’s in a very feminine dress. She sighs. “I suppose so, Ma’am.”
“You suppose? Don’t you know?”
“Sorry, Ma’am.” She looks down, only to see the apron and shiny shoes that once gave her such pleasure when she wore them only when she wanted. “I do know.” She runs her tongue across her lips, only to taste her recently refreshed lipstick. “I am a sissy girl.”
“And you can never change that, can you Roberta?”
Sarah laughs softly and grins. “Then tell me, are men’s clothes at all appropriate for a sissy girl…..like you?”
Roberta starts to stamp her foot, in frustration, but catches herself. “Well, not most of the time. I know that, now. But for work I would like to dress like a man. Pretend to be a man. Please.”
“Why do you need to pretend? Maybe you could wear your shorts outfit. That’s sort manish…pants and a white blouse.”
“Oh please! Ma’am. That would be even worse than dresses.”
“Then answer my question. Why do you need to pretend?”
“If I dress like you want, They will all laugh at me. They will lose all respect for me.”
“Really Roberta. Do the laugh at you when you’re shopping?”
“Do they seem to respect you.”
“Well, yes Ma’am.”
“And I’ll bet some of them think you’re pretty, don’t they?”
“I think so. You know how hard I try.”
“And you’re not pretending when you make yourself a pretty sissy girl, are you?”
“And you weren’t pretending at the salon, were you?”
“If fact, they all knew you were a sissy?”
“And the girls at the salon were all nice to yes, weren’t they?”
“They treated you with respect?”
“And last night, you weren’t pretending to Bill and Holly, were you?”
“Weren’t they nice and respectful to you ?”
Roberta knows where this is going. “Yes, ma’am.”
“Then I really don’t see any reason for you to pretend at work..to be anyone other than the sissy girl you know you are.”
“Pleeeese, Ma’am?” Roberta pouts with her as wide as they can go and twists a little from side to side, rustling her skirts. Sometimes Sarah found this endearing.
“Nice try, Missy. My answer is still the same. Even Jack thinks it’s a good idea. End of discussion. Dismissed.”
Roberta curtsies and holding back a sob turns and wriggles to the hall , sobs loudly and runs to her room, heels clattering and skirts swinging.
“Don’t you feel just a little sorry for her Sarah?”
“Absolutely not. I might if she didn’t make such a cute girl. She made me feel so much less of a woman. Dressing up and making me play along with her games. Well, she’s stuck in her game now, and I’m having fun. I’m sort of getting off controlling her. We’ll see just how long she can go without wearing pants. And, you know, it might be kind of fun to make her date a guy. Jack says he has a gay friend who might go for Roberta. A macho guy who really likes the femmy types….like Roberta. And, I’m just getting started with her. When I’m through, there won’t even be many real girls more femmy than Roberta. In fact. I’m thinking of entering her in the amature drag night at that club she made me go to.”
The next day, Bill consults the HR guys who suggest that a memo advising everyone of Roberta’s new status and reminding everyone that Roberta is still married and has the support of her wife. This at least will keep people from assuming she is gay. They are instructed to use only feminine pronouns and that Roberta will be using the unisex handicap single lavatory. Sarah checks in at lunchtime with some more feminine accessories for Roberta’s office, including a new picture of her with Jack to go on Roberta’s desk. She invites Jenny Johnson to lunch. “You will be amazed at what a girl she has become; sometimes I forget she’s really a sissy. We’ve been working really hard with her over the last few weeks to help her get rid of any masculine traits, and we would both be grateful by helping here at the office. If she does anything remotely masculine you should correct her immediately. Sometimes she may need the incentive of a little discipline. Feel free to impose corner time or make her write lines…that sort of thing.”
“But Robert is my boss….”
“It’s Roberta, dear, and she, she will hardly be your boss any more. She will still need your services to do her job, but otherwise I’m putting you in charge of her while she’s here. I’m sure that might take a little getting used to for you, but if you have any problems at all, just call me. Oh, Bill told me to tell you to get some new name plates for Roberta’s desk and door. It’s ‘Miss’ by the way.” Sarah takes out her phone and shares some images of Roberta in her new work outfits. “See? An improvement, don’t you think?”
“Wow! He really does look like a girl.”
“Sorry,” she giggles, “how could she be anything else? So, when should we expect to actually meet Roberta?”
“When do you think you will have her nameplates?”
“Day after tomorrow…at latest.”
“Then day after tomorrow will be her debut. Just remember, you are in charge now. I’ll even bet you can improve her job performance.”
Jenny laughs. “I bet I can, too!”
Over the next two days, the fretting tries every possible wile to persuade Sarah to relent only to end up standing in her corner, wearing her ball gag, before being sent to bed early to get her beauty sleep before her return to the office.
Her beauty sleep is fitful, and she is up early to make herself perfect for Sarah’s inspection. “You look perfect, Roberta. I’m proud of you. So, if you are a very good girl today we may just release your little thingy for a while after dinner. I’ll expect a very good report from Bill…Mr. Jones to you from now on, and of course from Jenny, too.”
Sarah laughs. “Why of course silly! You’re a sissy. Someone has to be in charge of you. I had a long lunch with Jenny on Monday. I told her about our new life and most of your sissy rules. Just do what she tells you, and I’m sure you’ll be fine.”
“But, ma’am. She always complained about me being too bossy when I was just trying to get her to do her job.”
“Well, Roberta, I guess she won’t have those complaints any more, will she?”
“Mmm. No, ma’am.”
A little concerned that Roberta might not really report to work, Sarah has Jack drive her. Roberta sits in the passenger seat, knees tightly together and patent leather purse on her lap. She avoids looking at the smiling Jack. They arrive at the visitors lot. Roberta removes her pink phone from her bag and rings Sarah, as ordered. “Hello, ma’am. We are here. Yes, ma’am…yes ma’am. Yes, I will ask Jenny to call. Yes. Good bye, ma’am.” Roberta replaces her phone and takes out her lipstick and pocket mirror. Having refreshed her lipstick, she turns to Jack. “Um, Sir. I’m supposed to ask you to escort me to the office…to Mr. Jones.”
“Sure, sissy. Why not?”
“Thank you, sir.”
They make their way to Bill’s office, which has a private waiting room and the work station of Bill’s PA, Marcy. They enter and Marcy asks if she can help them. “I believe Bill is expecting this young lady, Miss Roberta Miller.”
Marcy is visably shocked as she recognizes the new Robert. “OMG! I would never have guessed it was you. You look like a perfect girl. Mr. Jones is expecting you, but he’s on the phone at the moment. Please have a seat…..Miss Miller.”
Roberta gracefully seats herself, crossing her legs and placing her purse in her lap. Jack excuses himself, saying to Roberta, “Have a nice day, sissy. Sarah said she would pick you up around six.”
“Thank you Mr. Jack.”
Marcy continues to inspect Roberta. “Gosh, Miss Miller, I still can’t get over this. So, it’s true what the memo said? You really are a sissy?”
“Wow. You even sound like a girl. Here, Mr. Jones is finally of the line.” She dials the intercom. “Sir, Miss Miller is here. Shall I send her in? He’ll see you now, Miss Miller.”
Roberta rises and wriggles to the door, knocks softly and is bidden to enter. Roberta looks as she did the other night, so Bill is not surprised at all. He remains seated as Roberta remains standing, holding her pocketbook. “Good morning Roberta. You look as cute in the day as you did Saturday night. I guess there’s no turning back now. You’re probably going to get a lot of looks today, but if anybody harasses you, let me know personally. But do expect some teasing. We’ve told everybody, you’re still married. Not gay…just a sissy. I’m sure people will get used to you soon. Just keep doing the good job you always do and everything will be OK. Sarah told be about her talk with Jenny and how Jenny will be in charge of your sissy side and making sure your work doesn’t suffer. I’m OK with that, so I’ll expect you to cooperate fully with her. Understood?”
“Yes, Mr. Jones.”
“Good. Now you should go over to HR. They have some paperwork for you, and I guess you’ll need a new security badge with a new photo and name. So run along and report to Jenny when you finish at HR.” Even now, he can no longer think of Roberta as masculine, just a girl…more girl than sissy. This could end up as a win-win-win. Having Roberta in the office was making him closer to Sarah; Jenny and Roberta’s new relationship would certainly be far more productive than their old one; and there was something amusing about having the former Robert around as a sissy girl, although he couldn’t quite put his finger on it yet.
“Yes, Mr. Jones,” she says, barely restraining a curtsy.
“You should be able to make your way there by yourself. No one will recognize you yet.”
“Yes, sir.” She turns and exits the office, Bill marveling at the feminine sway of her hips.
In the waiting room, Marcy giggles as Roberta minces through.
HR consisted of two men in their forties who also had other responsibilities. Roberta delicately enters and is noticed by the one in charge. “May we help you Miss?”
“Uh. Yes, sir. Mr. Jones told me to check in with you.”
“I am Roberta Miller.”
“Holy cow! Dave! Come here. You won’t believe this. ….this is Roberta Miller, Dave. MISS Roberta Miller. I think you have her paperwork. Why don’t you get that, and I’ll get going with hi..her ID. I can certainly see why you need a new ID. Do you have your old tag? You have to turn it in.” Roberta sets her handbag on the desk, opens it, fishes out the old name tag, and sadly surrenders this vestige of manhood. “OK, Roberta, step this way. There is a mirror there the other girls use to check their hair and makeup. Using the mirror, Roberta freshens her lipstick, returns the tube to her bag, and turns for her photo. “Put your feet on those markings on the floor, focus on the x above the camera, now give me a little smile, very good sweetie. Look at the screen. I think that’s pretty good picture. Don’t you? I can take another, if you don’t like it.”
“Thanks. I think it’s fine.”
“Certainly an improvement over the old one, huh.”
“No, seriously, Roberta. You look tons better than Robert did. Really, you make a perfect sissy. You’re prettier than almost all the real girls here. I think you’re a natural. It’s amazing that you’re not gay or a transsexual. Although we would have to support you even if you were. Here I’ve finished your tag.” He hands her the laminate tag. The photo is indeed flattering. The company information is above the photo, and below it is written:
“Miss Roberta Miller”
“Why does it say ‘sissy,’ sir?”
“Well, you are a sissy, right?”
“We just don’t want you having problems with security for impersonating a woman.”
Roberta then signs the various forms, including one directly depositing her salary into Sarah’s personal account. The HR guys have no doubt who is wearing the pants in that marriage. Later they joke about that and Roberta’s feminine wedding ring.
“OK, Roberta. You’re all set. You should report to Jenny Johnson now. You do know where her office is?”
Roberta swishes and click clacks to her old office, which is a smaller version of Bill Jones’ suite with an enclosed reception area and workstation outside of a private office. Then she notices aplate by the exterior door which says “The Johnson Team.” This does not bode well. Roberta enters and notices that Jenny’s station is empty. To be safe, Roberta knocks softly on what was the door to her private office. She waits and is finally bidden to enter. Jenny is sitting at what was her desk. The nameplate says “Ms. Jenny Johnson.” Jenny looks up and with a grin says, “Weclome back, Roberta! And don’t you look cute? I can’t believe I never realized what a girl you could be or even that you were a sissy. You sure had all of us fooled. It must be such a relief to finally be out of the closet. Speaking of closet, let me get a closer look at your pretty outfit.” Jenny steps out from her desk and approaches Roberta, who notices (not without envy) that Jenny is wearing a pantsuit. She inspects Roberta, who, even in her heels, is measurably shorter than her former PA. “I love your blouse and skirt, dear. The really suit your figure. I can’t get over how flat the front of your skirt is and those cute little breasts. You look to be between an A and a B?”
Roberta sighs and flushes, knowing she must admit to her bra size. “Closer to a B.”
“Roberta,” Jenny says with a tone of disappointment, “when we are alone, it’s Ms. Johnson or Ma’am. Understand?”
Roberta looks down, mindful of her shiny purse, smooth skirt, and shiny heels. “Yes, Ma’am.”
“Good girl. As I am sure you are already figuring out, working here as a sissy will be a bit different than before. First off, since you are a sissy, someone has to be in charge of you, and you know who that is?”
“Naturally. And as a sissy, you have rules. Some of which apply at all times, and some of which apply only when we are alone like now, like your curtsey rule that Sarah told me about, not speaking without permission. Permission will also be required to leave this office for any reason, including visiting the little girls room. There will be other rules as we go along. With me so far?”
“Yes Ma’am,” she bobs.
“Now, you tell me from your own sissy experience, what rules do you think will apply all the time?”
“Um. I must be a perfect girl all the time. I must be polite and respectful to everyone. I may never swear. I will call most men sir, and most women ma’am. I will be perfectly groomed and dressed at all times. No pants. No flats without permission. No sports or guy talk….” She bobs.
“That’s a good start, Roberta. As to work, we will do most things here together. You can do most things at that table where I can watch you posture. If you need an actual work station, you can sit out in front, as you will whenever I need privacy. Since that will be your station now, you should arrange it appropriately. In fact, why don’t you get started on that now. Sarah left a box of things for you on your desk. Oh, and here’s your new nameplate and a nametag, Bill thought it might be good idea for you to wear a name tag until everyone gets used to you. I know, only the girls in the steno pool wear them, but he is the boss.” They both say “Miss Roberta Miller.” She takes the tag and nameplate, curtsies, and goes out to her new area.
She pins on the nametag. It’s pink script on a silver pin. The nameplate is impossible to miss on the workstation desk. In Sarah’s box is a framed photo of Sarah and Jack inscribed by Sarah “To Sissy xxo Sarah” and then “& JACK” by Jack himself. Next is a pink mouse pad and other pink desk accessories. There is a small vase of artificial flowers. A collection of nail polish bottles in most colors she regularly wore. A makeup mirror, an extra comb and hair brush. A box of Midol. Summer’s Eve spray vaginal deodorant. jjj Several sets of spare pantyhose and stockings. Having put everything away, she sits, crosses her legs and waits for Ms. Johnson. She refreshes her lipstick. She is tempted to check ESPN like usual, but doesn’t want to chance being caught by Ms. Johnson. Just as well, as the office door opens just then. Roberta reflexively stands with a little bob. “Good girl, Roberta. I see you’re settling in.” She looks at the photo. “Cute couple, heh, heh. Oh. I’m glad you put on your nametag. We have a little time to kill, so we might as well start to introduce you to the others. It might be fun to see how long it take people to figure out who Miss Roberta Miller is. Come with me.”
The two girls go out into the hall. “Let’s go that way, sissy, and we’ll see who is around. My god, Roberta, how did you learn to walk like that? You really walk like a girl; not some guy in a skirt. Anyway, let’s start here at the steno pool. There should be at least six girls here now.”
They enter the steno area which has four work stations on each side, with the girls facing away from one another. No one pays the two girls much notice. Finally, Jenny clears her throat. “Girls. Here is someone I want you to meet. Who can guess who she is?”
Several of the girls swivel their chairs around. The one nearest Roberta rises slightly and peers at Roberta’s name tag. “OMG!” she almost shrieks, “Mr. Miller! The memo said you would be dressing up like a girl…like a sissy. But sir, you really look like a girl.”
Now, all the girls are standing to inspect the blushing Roberta.
“Girls. Mr. Miller is officially gone. May I present Miss Roberta Miller. She’s part of the Johnson Team. Do a little twirl for the girls, Roberta. Now, you all saw the memo. Even though she’s a sissy and still has a wife…or spouse…whatever…she’s now a girl here. She’s a she. Mr. Jones knows this is a little unusual, so feel free to get a better look at Roberta and to ask her any questions you may have. Don’t look so worried Roberta, you’re one of the girls now…sort of.” She giggles.
The girls do indeed inspect Roberta with comments and questions like: “I love your hair this way. The highlights really work for you.” “Nice nails, sweetie, are your toes the same color?” “She’s even wearing perfume.” “Are you wearing panties?” “Can you walk to the hall and back? I want to see how you manage your heels.” “Did you pick out your outfit all by yourself?” “How cute.” “Are you really a sissy?” “How long have been dressing like this?” “Aren’t you a little embarrassed?” “Do you sleep in nighties now?” “I can’t believe your wife is really OK with this.”
“Maybe I can help answer that one,” Jenny interjected. “I had lunch with Sarah…that’s her spouse… on Monday. Somehow she discovered Roberta was a sissy about two months ago and decided that she should be wearing the pants in the family since Roberta also made a cute looking girl. I think the power sort of went to her head. She made Roberta start doing all the wifely chores and dress the part more and more. But it wasn’t easy for Roberta to be a perfect girl after a day here dressed as a man. Masculine traits would slip in from time to time. Then she decided it would be better for Roberta to be a girl all the time. She’s chummy with Mr. Jones, who said OK as long as Roberta didn’t disrupt things here. I promised him that I would do my best to help Roberta fit in.”
“I still don’t get this. Robert seemed like such a normal guy. I still can’t believe he really wants to do this.”
“First off, it’s ‘Roberta’ and ‘she.’ You read the memo. I asked Sarah the same thing, though. You know what she said? She said it didn’t matter what Roberta wanted. She’s a sissy, and sissies do as they are told. Isn’t that right, Roberta?”
Roberta’s knuckles are white from clutching the pocket book at which she is staring. Jenny waits for a reply. Finally, “um…ah…maybe…….yes.”
“And what has Sarah told you to be?”
“So, what do you want to be?”
“a..um… a sissy girl.”
“If you girls don’t have any more questions, Roberta and I better run along. She has a lot more people to meet.”
Later, after Roberta has been introduced to just about the whole office and endured not a small amount of teasing, especially from the guys, Roberta is called into Jenny’s office. “It’s almost lunch time, Sissy. I would go with you, but I have to attend the team leaders’ lunch today, and I suspect you might be a bit uncomfortable with the guys you used to hang out with; you noticed none of them even mentioned lunch when they met the new you. So, I arranged with the steno girls to let you join them. They actually thought that would be fun. They’re still fascinated by what a cute girl you make. You should observe how they do everything and try to copy it. They really are the girliest bunch in the office. Why don’t you run along and join them at their station now?”
Roberta checks her makeup in the mirror at her station and freshens her lipstick. She heads for the steno pool and pauses on the way at the restroom to tinkle. It always takes so long to rearrange her shapewear. Continuing to the steno pool, she can’t but notice the occasional chuckle or shaken head. Almost at the pool, she approaches a hallway door where one of her old lunch buddies has paused. He opens the door for her saying, “Allow me, MISS Miller,” with only the slightest smirk.
Finally at the steno area, the girls smile and giggle as Roberta enters. One rises and says “Welcome to the girls club Roberta. Jenny told us how sincere you are about being a sissy girl. We think we understand that even though you are a sissy, you are not into men. You just want to be as much of a girl as you can. I suppose we should be flattered. So,we will do all we can to help you fit right in. We all love your outfit and hair, but before we go out into the real world for lunch, why don’t you show us your walk again and how you sit….we don’t want any of us to be embarrassed by any left over masculinity. Walk over to that end of the room and then come back and sit in that chair.”
Roberta does as she is told, her pocket book on her arm. It does bother her that she is stuck like this, because these girls are hot to say the least. She sits gracefully into the chair, crosses her legs, and places her bag in her lap.
“Good girl! No one would ever take you for a man, would they? But, still, you’ve got a way to go to be a real girly girl, but we’ll help you as we go along. So, fix your lipstick and we’ll go to lunch.”
As the girls make their way to the coffee, Roberta is given pointers on how to improve her walk and how to hold her hands and arms. At lunch, a salad in Roberta’s case, there is more of the same: how to use her hands when talking, how to use her eyes while talking. Finally Gloria adds, “you know Roberta, your voice is pretty good, but I wonder if just the slightest of lisps might help. Try it Roberta. Go on. Like Annie here.”
“Pleathe,” she says, rolling her eyes and flipping her wrist.
The girls laugh and Gloria says, “Really Roberta. Not like a faggy guy. Just a tiny lisp, like a girl. Keep listening to Annie. You can practice in your office after lunch. Then we can see how you’re doing at coffee break. OK?”
“Better already, hun.”
Later, back at her office, Roberta is obliged to tell Jenny all about her lunch with the girls, her lisp becoming almost reflexive. “That’s cute Roberta, and it’s a good thing those girls like you, because I’ve been asked to be a regular with the other supervisors. This way I won’t have to worry about babysitting you. Those girls will keep you from any backsliding.”
At coffee, the girls complement Roberta on her efforts at lisping and hand movements. They also teach her how to pout. “Mmm,” says Gloria as she looks closely at Roberta’s face. Are you doing your own make up, sweetie?” Roberta nods yes. “And did you choose your colors yourself?”
“Um, no. It wasth one of the girlsth at Golden Shears.”
“Just a little lighter on your lisp, honey. The girls and I were talking after lunch. Your makeup is just a little too formal for the office. Your lipstick should be a lighter pink and your eyes just need a little smokey shadow. Do you have those things with you now?”
“No, but I think I do at my work station.”
“Good. Next time you go to the little girls room, why don’t you redo things. You can show us at the end of the day, OK?”
Back at her office, Roberta does need “the little girls room,” and gets permission from Jenny. Once again there is the production of the shapewear and drying her chastity device. She gives herself a spritz of Summers Eve. Finally, she redoes her make up as the girls have suggested. On return to the office, she reports to Jenny, who actually notices and wonders about the makeup changes.
“The girlst thought this would be a better look for here than what I had before.”
“I think they’re right, sissy. By the way, Bill Jones…Mr. Jones to you…asked for you to stop by his office before you leave. He probably wants to see how your little day went. And, sissy, I expect you to tell him how much you appreciate our new working relationship. You know I’ll check.”
At the end of the day, Roberta showed the girls her new look, which met with their full approval. “Of course you’ll have to redo your nails to match when you get home…toesies too!”
Roberta goes to report to Mr. Jones, checking her makeup in the little girls room on the way. Mr. Jones’ secretary has left for the day, and his inner office door is closed. Afraid to intrude, Roberta uses the secretary’s phone to call her boss. “Mr. Jones? Hi, this is Roberta. Jenny tsaid you wanted to see me. … No, I’m actually in your outer office. I didn’t want to just barge in. Thank you, sir.” Having been bidden to to take a seat, Roberta carefully lowers herself into the sofa, crosses her legs at the knee. Having nothing else to do, she freshens her lipstick again. Fifteen minutes later Mr. Jones comes out, followed by one of the marketing guys. Roberta stands as gracefully as she can and holds her purse with both hands.
“Ah Roberta. Uh, Larry, did you have a chance to meet Roberta here, today?”
“Not till now, Bill. But, I did read the memo.”
“Well, Roberta, meet Larry Sorenson.”
“Nice to meet you, Mr. Sorenson.”
“Nice to meet you, too, Roberta,” he says, extending his hand to a former luncheon buddy.
Roberta limply offers her hand in the most feminine possible way, blushing bright red.
Releasing Roberta’s hand, he moves to the door. “Sorry to run, guys, but I’m super late. Good to have you on board, Roberta. You’re every bit as cute as everyone said.”
“Thank you sir,” she says softly.
In Bill’s office, having been bidden to sit, Roberta crosses her legs and points the toe of her shiny shoe to the floor, as she had been taught by the steno girls. “Only men point their toes up.”
“So, Roberta, how was your first day? I’m sure Sarah will want a report.”
Roberta grasps her pocket book with both hands and sighs. She keeps her eyes wide open as she was also taught by the girls. “It was OK, sir. No one was mean to me. I actually got a lot of work done.”
“That’s good. I’m assuming things are going well with Jenny. She seemed very supportive of your situation when I talked to her.”
“Oh, yes, sir. She’s been wonderful, just wonderful.”
“I hope you didn’t mind that I made her team leader. I was a little concerned that it might not be good to have a sissy at the supervisors’ meetings. I must say, I’m impressed at how she’s fitting in. And, at the supervisors lunch, she told me that she has hooked you up with some other girls who have taken you under their wing. How’s that going?”
“Um, well, they’re some of the steno girls.”
“Don’t tell me you want to be a secretary.”
“Oh no sir! I adore my job. It’s just that I didn’t have anyone to go to lunch with, so Jenny asked them.”
“Well, if they’re not helping you become a secretary, what are they doing?”
“Um, uh, they’re, like…..helping me become more girly.”
“Jeesh. I thought you were already awfully girly already. Especially after that performance at dinner.”
“I did too. But it seems these girls are the girliest girls in the entire company, and they think I still have a long way to go. Just today, they made me change my makeup, how I move my hands, and even how I talk.”
“Is that why you’ve started using that little lisp.”
“Yes, sir. Please don’t tell Sarah about them. Lord knows what I’ll become if they all team up!”
“But I thought you wanted to be girly. For everyone to know you are a sissy. You said you wanted to live your dream.”
“Um, well, it’s, um, really a little more Sarah’s dream. I used to like dressing up from time to time, but only when I wanted, and certainly not all the time. I liked being a man. Lunch with the guys. Following sports. The whole deal. Dressing up was just an occasional lark. It was a mistake to involve Sarah.”
“Looking at you now, Roberta, you couldn’t be more right. There is certainly no way you could ever be a man at this place. From what I hear, people think you must have been this way all along, and most people think you’re actually cute. What I care about is that you continue to do your good work without disrupting my operation here. After today, I think you should be able to do that.”
Roberta tears up, and it’s all she can do to keep from crying.
“Come on, Roberta, you’ll be fine. Just take it like a big ….girl.” He snickers. “I talked to Sarah a little while ago. I told her she could be very proud of her sissy.”
Sniff. Sigh. “Uh, thanks, Sir.”
“By the way, Roberta. People are noticing that you call all the guys ‘sir.’ Why are you doing that, sweetie?”
“It’s one of Sarah’s rules. She says it helps remind me that I’m a sissy.”
“I think it helps remind the rest of us, too. Anyway, Roberta, I am relieved this is working out as well as it is. I’ll let you go home to Sarah. Speaking of which, is something wrong with your Mercedes? I noticed your space was empty today.”
“Oh, Sarah had one of her friends give me a ride since it was my first day.”
“Was that friend my secretary said was such a hunk?”
“Um, yes, sir.” She blushes.
Mr. Jones grins as it dawns on him who Jack is. “Don’t tell me that guy was one of Sarah’s boyfriends?”
She nods yes.
“You poor sissy. Tell me you still have your balls.”
She nods yes, again. Blushing even more. She’s not about to tell him they’re locked up.
“Oh. I see it’s almost six-thirty. Sarah told me she would be picking you up about then. You probably better scoot. Somehow, I don’t think you would want to keep her waiting. Would you missy?”
Roberta waits for Sarah in the office port coachers. It has been twenty minutes, and her feet are beginning to hurt in their heels. But, she is afraid to call Sarah. Finally, she gets a text. “In front, Sissy.” Roberta wriggles to that side of the building as fast as she can. Just in time to see Sarah arrive, behind the wheel of what was once her Mercedes. Roberta daintily slides in to the passenger seat. “Thank you, mistress.”
“Well Roberta, what did I tell you? I talked to Bill and Jenny and they both said your sissy day went just swell. They said you were a very good girl, and there were no problems at all. I am proud of my little girl. We should have done this sooner. Aren’t you happy?”
“It did actually go smoothly, ma’am. I tried really hard, but honestly, I did miss dressing like a man and hanging with the guys. I don’t know if I’ll ever do that again.”
Sarah laughs. “Of course you won’t! There is no reason why you should, ever. We’ve had that discussion. Now, for the last time, Roberta, tell me what you are.”
“I’m sorry, ma’am. I am a sissy girl.”
“And, do sissy girls ever dress up like men?”
“And, do you sissy girls ever ‘hang with the guys’?”
“Um, no, ma’am.”
“Tell me, sissy, if you didn’t hang with the guys, with whom did you hang?”
“Just some of the girls, ma’am.”
“Some OTHER girls, you meant. Which other girls?”
“Uh, some of the steno girls.”
“Were they nice to you?”
“Yes, ma’am. They want me to join them for lunch all the time since Jenny eats with the supervisors and I can’t eat with the other guys any more.”
“You didn’t really mean OTHER guys did you?”
“Um, no, sorry.”
Sarah laughs. “Of course not. So what do you and your girlfriends talk about?”
“Oh. Mostly office gossip. So far, they’ve been good about not prying into my ‘situation’ too much. And, they talk about clothes and shopping and that sort of thing.”
“Maybe they can help you sweetie. You still need to fill out your wardrobe. By the way, I see you have changed your makeup a bit since this morning’s inspection. What’s with that?”
“Well, the girls just thought this would be a more appropriate look for there. I hope it’s OK.”
“Sure, but you need to fix your nails.”
“I know, ma’am.”
“Roberta…am I hearing a little lisp that wasn’t there before?”
“Uh. Maybe. Yes?”
“Don’t tell me this was your girlfriends’ idea?”
“Well. Actually it was.”
“They thought it would make me sound more girly. Fit in better, I guess.”
“You know, I think they may be right. It is sort of cute and not faggy at all. I think I like it. Talk like that from now on. OK?”
“All in all, I think you have been a very good girl today. I know you know you are not allowed to discuss your little clitty, but I’ll bet you’re just a little horny. Right sweetie? How long have you been locked up?”
Roberta is desperate for release and knows the penalty for asking for it. “Four weeks, ma’am.”
Sarah giggles. “Oh, my! When we get home, I’ll ask Jack if he will let you out for a little while since you have been so good. I’ll warn you though, it’s my time of the month, so Jack may ask you for something in return. I’m afraid he watched your little movie again today. I sometimes get a kick out of it myself. It’s funny, until I saw that, I had no idea how much of a sissy you really were.” She laughs. “We should both be grateful to Jodie. If it weren’t for her, you would probably still be pretending to be a man, you silly little sissy. Anyway, you seemed to have so much fun in that movie with that stud, sucking Jack off should be a piece of cake for a girl like you.”
“Please, ma’am, they made me do that stuff for the movie. I can’t begin to tell you how yucky it was. As for Mr. Jack, just kissing that thing of his that one time was awful.”
“Well, I don’t think it’s awful. I’d probably suck it myself, if it weren’t for my gag reflex. Why, I couldn’t even suck your teeny tiny little thingy. Besides, Jodie told me all sissies love to suck cock, and we all agree that you are a… what Roberta?”
“A sissy, ma’am. But, please, ma’am, could I not do that with Jack? I mean Mr. Jack.”
“Roberta. I’m not sure you’re being a very good sissy. You don’t need to spend some time with Jodie do you?” Roberta shakes her head no vigorously. “So why don’t we just leave it up to the man himself?”
“Then I don’t have to do it if he doesn’t ask me to, ma’am?”
“You don’t. But of course, as the polite girl that you are, you will ask him nicely if that’s something he would like you to do for him. Then, it’s up to him….. as is any release you may enjoy.”
“Really, Roberta, you know how it works for you sissies.”
Roberta sighs, “Yes, ma’am.”
A bit later, Sarah is relaxing in one of the stuffed chairs in the library. Her lovely legs are crossed. She sips her wine and idly thumbs through the new Vogue. “You know Jack, I think Roberta wanted to ask you something else.”
Jack is lolling in the other chair, his legs spread wide. He is breathing heavily. He looks over at Sarah and raises his eyebrows questioningly.
“Yes, sweetie. She thinks she has been a good sissy girl for quite a while and she told me she was hoping you might unlock her for a little while. The reports on her from work are actually pretty good. It’s up to you though, and I suppose she should ask you herself.”
“Is that true, Roberta. Have you been…” he pants…” a really good sissy?”
Roberta, of course, still in her work outfit, is on her knees, her lips wrapped tightly around Jack’s giant member, her eyes fixed on Jack’s face…as she has been taught by Jodie and her husband. She does her best to nod yes.
Roberta is desperate. “Um Hum,” she hums loudly.
“Umm. That feels good…..do that..some …..more!”
Roberta continues to hum and suck foe all she is worth. She is one horney sissy. Finally, Jack ejaculates. “Wow……..good girl, Roberta.”
Roberta swallows it all. Licks her lips and then licks Jack clean as she has been taught. When Jack is finally flaccid, she gives his member a final kiss, gently returns it into his pants and zips them up. She remains on her knees. She looks up at Jack and delicately raises her hand. Jack nods, and in her sweetest voice she says, “Um, please Mr. Jack. I promise I really have been a really, really good sissy girl. May I please be released for a little while? Please, sir?”
“Tell me, girl, just why is it you want to be released?”
“Please, sir, so I can cum. It’s been soooo long.”
“I suppose even you sissies deserve to cum now and then.”
“Yes, sir. Please sir.”
“Tell me, have you douched since you got home?”
“Why don’t you run along and do that and clean yourself in front, too. Then come back, and we’ll see what we can do for your LITTLE problem.”
Roberta rises, curtsies, and turns to go to her room. “Oh, and bring some latex gloves.”
As Roberta wriggles away, Sarah starts to giggle. “Wow, Jack. I didn’t believe you when you first told me about making Roberta cum by rubbing her prostrate, so I checked online. You are right. Sissies end up just cuming in their little cages. But, the articles also say the orgasm isn’t nearly as good as a normal one. Poor Roberta.”
A few minutes later, a well douched and very excited Roberta hurries back into the room. She hands Jack the gloves, a bit unsure why he needs them. “One more thing, sissy. Go to Sarah’s bedside table and bring back the lube in the drawer and a hand towel.”
Having hoped for relief from a simple wank, Roberta finds herself bent over one arm of the library sofa, her hands and face on the cushion. Sarah is reclining at the other end, looking down at Roberta’s upturned face and across at Roberta’s bottom as Jack flips up her skirts and lowers the rear of her frilly panties. The latex gloves snap as Jack pulls them on and observes with a chuckle, “You know, Sarah, this might be a little disgusting if Roberta were a man, but it’s really rather amusing with a sissy girl. What do you think?”
“I don’t know Jack. I’ve never seen this done to anybody. What’s next?”
“Well, first we lube Roberta like this. Sort of like in her movie. Feel good sissy?”
Roberta just stares at the cushion.
“Roberta, look at me. Jack is doing you a big favor, and he just asked you a question. Well?”
“Um, sorry ma’am. Um, yes sir. It feels……” Roberta squeals with surprise as Jack slides his index finger well into her. Sarah giggles at the expression on Roberta’s face.
“To be honest, girls, I’ve never actually done this before, so I’m going to need you to tell me how I’m doing. Roberta, tell me when I get to your sweet spot.”
Jack continues to experiment. “Oooh. There!”
“There, SIR,” Sarah admonishes.
“SIR,” Roberta is barely able to say as her breathing accelerates.
Jack laughs. “You know Sarah, it may be hard for Roberta to talk during this. I know. Roberta, why don’t you hum whenever I’ve got it right.”
So begins Roberta’s song to herself, coaching Jack along with rising octaves and heavy breaths. Sarah grins down at her sissy as she nears climax. Then Jack stops and Roberta squeals in frustration.
“Jack! I think you almost had her there!” Sarah laughs.
Laughing, Jack starts manipulating the panting Roberta again. “I can’t hear you sissy.”
To Sarah’s amusement, Roberta resumes her humming. Jack plays her like an instrument for another five minutes taking delight in further debasing Roberta before Sarah and further removing any possibility of Sarah ever considering her a man. Finally, squealing like a little girl, Roberta is allowed to cum. Jack slowly removes his finger which, except for the KY, is quite clean. Lucky for the panting Roberta who next discovers it in her mouth.
“Now aren’t you grateful to Jody for your feminine hygiene?” Sarah asks, laughing.
Roberta can only shake her head yes, moving Jack’s hand up and down. He slides it out, and in a quick move gives Roberta an almighty slap on her bottom, his other hand holding her in position.
Sarah laughs again. “Let her up, Jack. Let’s get a look at the front of her panties. As instructed, Roberta holds her skirts up before his seated wife, who with thumb and forefinger delicately lowers Roberta’s panties below her chastity cage. Sarah and Jack both laugh as Sarah observes “Aren’t you the talented one, Jack? You got her to spurt tons more than that guy in her movie. I’m glad you thought to put that towel on the sofa. But Roberta, you are one messy girl. Go clean yourself up. Keep holding your skirts up, or they will get all yucky.”
Doing as instructed, Roberta wiggles away, still recovering from her first orgasm as a girl and still not quite sure what to make of it…and still longing for an erection.