“Chrissie” Parts I and 2 by c.w. cobblestone -updated 24 04 2022

“Chrissie” Parts I and 2 by c.w. cobblestone -updated 24 04 2022


“Chrissie” Part I

by c.w. cobblestone


My right leg had a mind of its own.


Rebecca frowned. “Why you keep bouncing like that? What’s wrong with you?”


“Um, I … I … nothing.”


“Bullshit, nothing. Something’s up; you’ve been acting weird all night. What the hell’s going on, Chris?”


I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath.


Took the plunge.


“Okay. Okay. It’s just … well, now that we’re talking about moving in together, I just think we need to be honest with each other. And I … well, I haven’t told you everything about myself.”


“Uh oh. Do I want to hear this?”


I sucked in more air but couldn’t exhale.


“What, Chris? What haven’t you told me?”




“Um, yeah … so … I … I have this fantasy. Well, it’s not really a fantasy; it’s more like a … need. It’s a need … for some reason, and I don’t understand why, but I need to have a woman treat me like a slave … for her to … um, dress me up in … in women’s clothes and … and treat me like … like a … a sissy. It’s weird, I know, but it’s something I’ve wanted since I can remember.”


My pulse jackhammered my jugular. The thumping was the only sound until, finally, Rebecca made her chair creak by crossing her legs.


“Chris … honey, I’m sorry, but that’s not … I don’t … I don’t want that, Chris. I mean, I’m not putting you down if that’s your thing, but it’s … it’s not my thing. At all. I do appreciate you telling me all this before I gave up the lease. Now … I guess … well, I guess we can move on … with no strings or anything.”


My eyes welled. “Are you saying … are … are you breaking up with me?”


“Well, I don’t see how we can stay together. Do you?” Tears filled her eyes, too. “I’m sorry, but a man dressed like a woman just doesn’t turn me on, Chris. It’s bad enough—” She halted mid-sentence and looked at her hands.


“What? It’s bad enough what? That I’m shorter than you?”


Rebecca sighed. “Well, I wasn’t gonna say it, but if you want to go there, Chris, yeah. I mean, no offense, but I get a little tired of never wearing heels when I dress up because I don’t want to tower over my date.”


“I-I’m sorry. I told you, I could wear elevator shoes.”


“And what? That would make me only an inch taller than you in heels? Besides, that’s not the point, Chris. It’s not about how tall you are; I like masculine men — not guys who wear girl’s clothes. And I want to be in a relationship with a man, not someone I treat like a slave. I don’t find anything sexy about that whatsoever. No offense, but I just don’t.”


“I’m … I’m so sorry.”


She exhaled. “Well, I guess this does explain why you’re always so helpful. I’ve never met a man who volunteered to clean my apartment like you did. I get it now. That’s your thing. You were probably fantasizing about wearing women’s clothes while you were cleaning. And me treating you like a slave. Weren’t you?”


“I … uh …”


“Tell the truth.”


“Okay. Yes. I was. I … I’m sorry.”


“Well, Chris, I’m sorry, too. I really am. And, again, I do want to say thank you for telling me all this before we moved in together. I really appreciate that. A lot of guys would’ve waited and then sprung it on me afterward, hoping to get me to go along. That says a lot about you, Chris, and the kind of person you are. You’re sweet. Considerate. That’s what attracted me to you in the first place. So, I’m hoping we can still be friends. Okay?”


My head fell to my chest and I started bawling. She placed her hand on my ear.


“Don’t be like that, Chris. I’m sad, too. Look, we had some good times together. You took me to some wonderful places I’d have never been able to afford, and I really appreciate it. But it just wasn’t meant to be. Let’s just walk away from this on a positive note, okay?”


I sniffled. “Okay. I’m sorry. It’s my fault. I’m the one who’s … a pervert.”


“Oh, come on, honey. That’s not true. Everyone has their thing; it’s just not my thing, that’s all. You’re not a pervert. You’re just … different.”


“Well, I’m sorry I’m not the man you need me to be, Rebecca. I really am. I really do love you very much.”


“Oh, Chris, you’re such a doll. There’s love on this end, too, but … honey, I’m sorry — it’s not going to work. It’s just not. Don’t take it too hard, Chris, okay? You’ll find someone else; someone who’ll be more suited to your … interests. We both will. It’ll all work out somehow. You’ll see.”





The Cubs were trailing the Cardinals, 1-0 with two on and two out in the bottom of the ninth when the phone rang. I saw the name on the caller ID and forgot all about the stupid game.




“Hello, Chris? It’s Rebecca.”


“Rebecca?! Hey, how you been?”


“I’m fine. You?”


“Great. Gawd, it’s so good to hear from you after all this time. Uh, what’s … what’s going on?”


“Listen, Chris, can we meet for drinks?


“Of course. Hey, is everything okay?”


“I’m fine. Let’s talk about it when we meet, okay?”


“Um, sure. When you want to meet?”

“Tonight’s fine if you’re free.”


“Sure, I’m not doing anything.”


“Great. Meet you at O’Hara’s at 8.”


She hung up.


I couldn’t breathe.





The light filtering through the tavern window gave her hair a sparkle, making it easy to spot her as soon as I walked in the door.


As I approached her booth she stood and had to lean down a bit to hug me. It sent a familiar shiver of shame through my spine.


“You look well.” She sat back down.


“Thanks, you’re … beautiful as always.”


“Have a seat, Chris.”


I scooted into the booth across from her. She smiled.


“So, Chris, are you dating anyone?”


“Uh … no. Not right now. Um … er, how about you?”


She wiggled the fingers on her right hand, showing off the small diamond on her wedding ring. “I’m married, Chris.”


I slumped. “Oh.”


She giggled. “Aw, you look so sad. You always were such a little puppy-dog.”


I gazed across the table at her, blinking back tears. “I … I don’t understand.”


“Well, Chris, it boils down to this: I could use a slave right now. And I thought of you.”


Blood rushed to my head and other places. “Uh, I, uh, um …”


Our conversation was interrupted by the waitress. After we ordered, Rebecca leaned back in the booth.


“As I was saying. I could really use a slave in my life. Especially for cleaning.”


“Eeeyah, buh, uh, you, uh, I … er, you …” A series of sounds spilled out of my mouth.


Rebecca’s foot found my boner beneath the table. She smirked. “So, I take it you want the job?”


“Um, I … I don’t understand, Rebecca.”


“What’s there to understand? Didn’t you tell me you wanted me to treat you like a slave?”


“Well, yeah, but … but that was when we were in a relationship together.”


“So what? If we’d had the kind of relationship you wanted, how would you have wanted me to treat you? Like a boyfriend? Or like a slave? I’m just going by what you told me, Chris. You said you wanted me to treat you like a slave … and dress you up in women’s clothes. You said it wasn’t just a fantasy; it was a need. Didn’t you say that, Chris? Or am I going crazy? I seem to remember you saying that.”


“Yeah, I did say that. But … but, you’re married now, Rebecca.”


“Who cares? I guarantee if I’d have taken you up on your offer three years ago, there’s no way I’d have not seen other men. I told you back then — guys who dress up in women’s clothes don’t turn me on. Masculine men turn me on. But I’ve changed my mind about the slave sissy thing. Having one, I mean.”


“But … but how would that work? If you’ve got a husband—”


“What, I can’t have a slave and a husband at the same time?”


“I … well, yeah, I suppose. But what would he say?”


“Karl’s open-minded; he wouldn’t care if I had a slave, as long as I wasn’t having sex with him. And before you get any ideas, that’s never going to happen, Chris. Ever. I’m in love with Karl.”


I licked my lips. “I … I don’t even know what to say, Rebecca. I just … what changed your mind about this? You said it didn’t turn you on.”


“It doesn’t turn me on. Karl turns me on. Having a slave isn’t about turning me on, Chris. It’s about making my life easier. I’m at a point where I’m tired of settling. I want what I want. And right now, I want a slave. I got to thinking about what you’d told me the night we broke up, so I called you. If this isn’t something you want to do, that’s fine. I’m sure I could go on one of those kinky websites and find someone who wants the job.”


“Oh, I’m sure you could.” I wrung my hands. “Um, is it okay if I think about this for a few days?”


“Sure, thing — Chrissie.”


I gasped. She smirked, knowing how using the feminine version of my name had just destroyed me.


“I’ll need an answer by Wednesday,” she said.


I melted in the booth. “Um, okay.”


The waitress arrived with our drinks and burgers. There wasn’t much conversation while we ate. Rebecca took off shortly after.


I picked up the check. Then I went home and didn’t sleep for two days.






“Chrissie,” part II

by c.w. cobblestone


My eyes were pried open. The Deluxe Diet Deep-Frier infomercial wasn’t making me drowsy. Crosswords and sudokus didn’t do the trick. No matter which side of the pillow I hugged or how many sheep I counted, I couldn’t tune out the two syllables whispering in my inner ear:


Chrissie …


I slipped on my frillies and fumbled with my dick. It wouldn’t get hard. This situation was beyond masturbation. There was too much thinking to do with the big head.


Chrissie …


Nothing made sense. Rebecca was married; why would she reappear in my life all of a sudden? Dollar signs in her eyes? That seemed the obvious guess. But she never was like that. While we were dating I offered to take care of her financially. I told her she wouldn’t have to work; told her she could relax, go to the gym or do whatever she wanted. She refused, even though she didn’t make a lot of money as a Best Buy cashier. She said she didn’t want me “taking care” of her. That showed me Rebecca was both beautiful and independent — exactly the kind of woman I’d always fantasized about.


Alas, when we started talking about possibly moving in together, I laid my sissy slave cards on the table. And she dumped me like a sack of soggy French fries. Although it tore me up, I figured she just wasn’t the dominant mistress of my dreams and tried to move on. I’d never really gotten over the rejection of that night and hadn’t dated anyone since.


What now?


Chrissie …


I closed my eyes and the little head took over. On the black screen of my shuttered eyelids, an endless loop detailed every nuance of the half-second it took her to utter that frightening, glorious, terrible, empowering, enslaving word:


Chrissie …


The way her lips had contorted like a smirking snake to form the sibilant “s” sound.


Chrisssssssssssssssssssssssssssssssssssie …


That glint in her eye after she realized she’d literally just taken my breath away.


Chrisssssssssssssssssssssssssssssssssssie …


I pulled my hand from my crotch and rubbed my chin. Maybe her husband was behind this. That Karl asshole. Was he pulling the strings? Maybe Rebecca had told him about an ex-boyfriend who wanted to be treated like a sissy slave, and Karl figured he could exploit me through her. They clearly weren’t rolling in the dough, judging from Rebecca’s wedding ring.


Was this a setup?


Chrisssssssssssssssssssssssssssssssssssie …


The little head jumped in. What if it wasn’t a scam? What if Rebecca was telling the truth? What if she really did want a slave in her life?


The idea of being Rebecca’s sissy slave overwhelmed me. I focused on that the rest of the night. I wasn’t able to get to sleep but I finally shut off the big head and jacked off five times.


With saggy eyes, a sticky stomach and a sore pee-pee, I dragged my ass out of bed at sunrise and prepared for what I knew was going to be a motherfucker of a Monday.





Tuesday started out even shittier. I called in sick and lay in bed all day with a pounding headache and a throbbing boner.


By then it wasn’t a matter of whether I was going to agree to Rebecca’s out-of-left-field request — the only question was whether I would wait until the next day’s deadline to call her or inform her immediately.


The choice was made for me when Rebecca phoned just after 7 that evening.


“Listen, I know I said you could wait until tomorrow but I need to know now, Chrissie. This house is an absolute mess; if you’re going to be my slave you need to get your ass over here now and get cleaning, because I can’t stand living in this pigsty another minute. And I don’t feel like doing it myself. So, are you going to do this or not?”


I swallowed the lump in my throat. “Um, yeah.”


“Yeah? Is that how my slave should address me, Chrissie?”


“Um … Mistress?”


“No, I don’t like that. You call me ma’am. Understand?”


“Yes, Ma’am.”


“See? That’s a good little sissy. Chrissie the sissy. Now, listen, Chrissie the sissy, you need to get over here pronto and get this damn house clean.”


“Yes, Ma’am. Um, can I have your address?”


“It’s 16242 South Sycamore. Hurry up, now, Chrissie. This is going to be so much fun. My own little sissy slave.”


“Y-yes, Ma’am.”


“Oh, and Chrissie?”


“Yes, Ma’am?”


“Go ahead and bring whatever little girly outfit you like to wear. Whatever will make you clean better. Okay? Will you be my little maid? Isn’t that your big fantasy?”


“Yes, Ma’am.”


“Well, it’s my fantasy to have a nice, clean house. So get your little sissy butt on over here.”


“Yes, Ma’am. Um … excuse me, Ma’am?”


“Yes, Chrissie?”


“Is … is … he … will your husband be there?”


“Why wouldn’t he? He lives here.” She sighed. “Listen, Chrissie, if this is going to be a problem—”


“Oh, no, please, Ma’am, please, I’m sorry. I want to serve you. I do. I don’t mind if … if your husband is around, as long as I can serve you, Ma’am. I was just asking. I’m sorry.”


“There’s my little doll. It’s time to hang up now, Chrissie. I need you here.”





North Sycamore was where the nice houses were; the south end of the street was literally on the other side of the railroad tracks, where folks installed bars on the windows of their dilapidated shacks.


I pulled up in front of 16242 South Sycamore. My beautiful Rebecca lived in a shit-hole.


It took every ounce of courage to peel myself out of my car and amble up the walkway. With a trembling sigh, I tapped on the door. It swung open and Rebecca’s smile melted my apprehension while adding to it at the same time.


“Why, hello, Chrissie,” she said in the same mocking tone I’d played in my head a million times over the past few days.


I stepped inside and was surprised when she leaned down and gave me a light hug and a peck on the cheek.


“Come in and meet Karl.”


I followed her into the house, my eyes on her ass but my peripheral vision taking in their messy quarters. Rebecca hadn’t been kidding — this dump definitely qualified as a pigsty.


As soon as I spotted Karl a chill shot through my spine. The guy instantly intimidated the shit out of me. He shifted on the sofa and sneered when his wife led me into the living room.


“Baby, meet my new slave, Chrissie. Chrissie the sissy. Chrissie, this is my husband, Karl.”


I couldn’t look him in the eye. He rose from the couch and towered over me. He must’ve been at least 6’3, and the contrast between us was palpable, which is why I think he stood up — he wanted to shame me. It worked.


“Hello, Chrissie,” he said. “You come to clean our house for us?”


“Y-yes, sir.”


He chuckled. “Sir, huh? I like it. Becca, this guy just might have possibilities.”


“Told you,” my ex-girlfriend said. “He’s a little doll.”


She then smirked at me and pointed at the carpet. “Kneel down right there.”


I obeyed as she and her husband settled in next to each other on the couch.


“So, Chrissie, you’ve probably got a million questions.”


“Yes, Ma’am, I … I do.”


“Well, now’s the time to ask.”


I licked my lips. “Well … um, I was kind of surprised that you called.”


“That’s not a question, Chrissie.”


“Oh. Sorry. Um, why … I was just wondering what made you call me after you said this wasn’t something you were interested in.”


Rebecca snuggled closer to her husband. “I think you misunderstood me, Chrissie. I told you I wasn’t interested in treating my boyfriend like a slave. I wasn’t interested in my boyfriend dressing up in women’s clothes. I told you, I like masculine men.” She squeezed Karl’s bicep and smiled at me. “Obviously.”


“But … I … I don’t understand.”


“What’s there to understand? I didn’t want you as my boyfriend after you told me you were a closet sissy. That blew it for me. We never really did have that passionate of a relationship in the first place. Nothing like what I have with Karl. But lately I’ve been thinking more and more about things, and I remembered what you told me. About wanting to be my slave. And I think I’d like that. Having a slave, that is.”


Karl kissed his wife’s head. “She hates housework. Me too. That’s where you come in.”


Rebecca flicked a speck of lint off her sleeve. “So, Chrissie, that’s the long and short of it. There’s nothing else really to discuss. You need to start cleaning. The mop, and Pine-Sol and stuff are in the basement. Did you bring something girly to wear while you clean?”


I gulped. “Um … I … yes, I’m wearing it under my clothes.”


She shrugged. “Well, get undressed or whatever you need to do and get started.”


“Yes, Ma’am.”


After I knelt there for a few seconds, she threw up her hands. “Well?”


I stood and undressed. They chuckled at my lacy red teddy and thigh-high stockings.


Rebecca cocked her head. “Are you going to be a good little worker for me all dressed up in your girly clothes, Chrissie the sissy?”


“Y-yes, Ma’am.”


“Okay, then. Get to work.”


I turned to leave but she stopped me. “Wait. Get me a glass of iced tea, first.” She glanced at her husband. “You want one, hon?”


“Sure,” he said.


Rebecca snapped her fingers. “Two iced teas, Chrissie the sissy. And then get this place cleaned.”


Karl guffawed and picked up the TV remote. “I think I’m gonna like having a slave around.”


Rebecca kissed him. “You know it, babe.”


And so, while Rebecca and Karl relaxed on the couch watching television, I busted my ass all evening cleaning their house. I was interrupted three times for drink refills, once to bring potato chips, and once when Rebecca had me run outside to fetch a receipt from the glovebox in her car.


While I polished the dining table I could see them on the sofa. Pangs of jealousy shot through me seeing her nestled in the arms of her virile, tall lover. She’d never sat that way with me. When we’d watched TV together, more often than not I’d sit on the floor — perhaps a subconscious playing-out of my then-secret desires.


At about 11:00, as I was scrubbing out the oven, Rebecca called me into the living room.


“We’re going to bed, Chrissie, so you can call it a night and go home,” she said. “This is a decent start, but there’s a whooooooooolllle lot more cleaning to do. You’re working tomorrow, right?”


“Yes, Ma’am.”


“You still get off around 5 or 6?”


“Most nights, yes, Ma’am.”


“Okay, then report back here as soon as you get off work. I guess you can wear your sissy cleaning clothes underneath your suit. That’ll make for an interesting day, huh?”


“I … I guess, so, Ma’am.”


“Well, then we’ll see you tomorrow, Chrissie. The house looks good. You’re such a little doll. My little house-cleaning sissy doll.”


“Yes, Ma’am. Thank you, Ma’am.”


“You should probably thank Karl, too, Chrissie.”


“Thank you, sir.”


“No problem, pansy,” he said.


Rebecca giggled. “Good night, Chrissie. See you tomorrow.”