New Man of the House by Chrissy E

New Man of the House by Chrissy E

 

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Book One

Chapter 1

The giant butt plug made me squirm and moan in discomfort as I knelt by the door. Don had been training me well from a distance; having me wear bigger and bigger plugs each week. The one lodged in my ass as I knelt patiently felt like a giant log.

It had taken me months to convince Steph that we should have Don visit us. But now that the day was finally here, she seemed genuinely excited to have another man in the house. I couldn’t help but have some second thoughts though. The scary reality was finally sinking in. He was going to be in the house any minute.

Steph meanwhile was looking completely gorgeous. Her blonde hair came down over her bare shoulders in a tantalizing way. The light summer dress she had chosen flaunted her beautiful natural breasts, and invited you to explore with your hands. I wanted to fuck her so bad. My tiny boy clit had been locked without relief for two weeks, and it was aching desperately for pussy.

The doorbell rang, and Stephanie jumped to answer it. Her dress flipped back and forth tantalizingly as she swung the door open.

Don confidently introduced himself to my wife and stepped inside the house. Steph took his hand and pulled him inside.
I knelt quietly, my head bowed slightly. This was terrifying.
He looked over at me cowering and chuckled “Hi Crissy. You look even weaker in person than I thought you would”.

I just nodded, not knowing what to say.

Don looked at my wife and told her he was looking forward to taking her out of that dress, but he had to get everything else settled first.
First he asked where the keys for my chastity cage were.
Steph smiled and took the chain from around her neck and handed the key to him.

“Is there a backup?” he asked. Steph ran and got the other key out of hiding and handed it to him as well. My heart sank as I saw the keys to my aching sissy clit handed to this confident man who was invading my house.

He looked at me, a big smile on his face. I was helpless, and he knew it. I thought I might cry.

But he wasn’t done.

“Okay wuss. Now it’s your turn” he ordered. “I want you to go find absolutely every house key, including spares hidden outside. Take as long as you need.”

I jumped up and ran to do as I was told, already eager to keep the man who now owned my clit happy.

I found all four, and I cautiously knelt in front of him, holding them in my palm.
“Good girl” he said confidently as I weakly gave them to him. “I own this house now, and you are both trespassing on my property.”

I looked up, horrified.

He grinned “I’ll let you stay here for now, but I might kick you out at any point. So be a good girl and earn your keep.”

I thought Stephanie would be as horrified as I was, but it was having the opposite effect on her. Watching this strong man come in and take over was obviously getting her wet. She was tilting her chin, giving Don the “fuck me” look.

Chapter 2

Stephanie was a virgin before we were married, so the only sex she had ever experienced was with my 3 inch clit.
I was sure the neighbors would hear as Don gently pushed his big rod inside her dripping pussy. She was finding out what she had been missing all the years of only having sex with me.

I watched from the foot of the bed. Don had brought a present for me: the most massive dildo I had ever seen. It was close to a foot long, with a massive girth.
Before ripping my wife’s dress off, he had bent me over and shoved it deep into my sissy ass. The humiliation of having the giant cock shoved up my ass in front of my wife was worse than I could have imagined.

So while Don spread my wife’s legs and gave her a series of loud orgasm, I knelt on the floor and obediently fucked myself with the dildo.
Steph was amazing. Every few minutes she arched her back, her toes curling as she screamed his name.

She completely forgot I existed. His cock was her world for that moment.
Don fucked her for what seemed like an eternity. I lost track of how many times my wife screamed in orgasm. Meanwhile, my ass was stretched to the point of no return.

Finally I saw his ass cheeks start to clench. He grabbed her ass tight and plunged deep into Steph’s pussy as he shot his load.

Even though I had dreamt of this moment, seeing another man’s cum oozing from my wife was a hard pill to swallow. And it wasn’t all I was going to be swallowing that day. Steph looked at me. She was radiating. I wasn’t sure I had ever seen her look so satisfied. As she smiled, I knew it was time for me to eat my cucky creampie.

I felt like such a faggot as I licked Don’s sticky cum from her stretched pussy. It came out in big warm globs, sliding down my sissy tongue. Don laughed at me as I gagged, my face buried in the pussy he had just fucked.

To add injury to insult, Don grabbed the bottom of the giant dildo and shoved it further up my ass as I licked his cum from my wife.
For her part, Steph was enjoying telling me how incredible a lover Don was. Periodically she would pause from singing his praises to ridicule my shortcomings.

After a few minutes, Don interrupted me. “Time for round two” he said confidently. Sure enough, his thick cock was hard again. He looked at me “You don’t get to watch this time. Go put that big plug back in your ass and make us some dinner.”
And with that he turned back to my wife, caressing her cheek before spreading her legs again. Predictably, I did exactly as I was told; scampering out of the bedroom quietly so the lovebirds could fuck without a sissy around to bother them.
My balls ached as I listened to my wife moan and scream. I had never heard sounds like this coming out of her. I made sandwiches as Master Don made another creampie.

After dinner there was another assessment of the household. Every computer in the house was now his. I whimpered as he typed in the new master password on what used to be my macbook. I was locked out of it for good.

At that moment something snapped in me. It was too much. Taking over my house, breeding my wife, taking my computer…I couldn’t handle it. I reached for the computer, my face red.
Don understood what was happening. Before I could grab the computer he had grabbed my wrist and twisted me around. “About to be disobedient, little cunt?” he asked with a little bit of a sneer.
I just whimpered weakly, knowing better than to struggle.

He pulled me over in front of the big windows facing the road. “Here, let me help you learn never to do that again.” He spun me around so my back was to the windows and looked me square in the eyes. “You are going to stay right here in whatever position I tell you for the next two hours, got it?” I nodded slightly.

What followed was a horrible belt spanking in front of the window with the lights turned on bright so the neighbors could clearly see my punishment. Periodically he would turn me around so my face was right up against the window. He didn’t want to leave any doubt in the neighbors’ minds as to what was going on.

Finally it was over. My ass was on fire. Don just left me, bent over, panties down, for the neighbors’ amusement as he went to lay in bed with my wife and watch tv.
Stephanie smiled and wrapped her arm around his neck, nibbling at his chin. “Make it three hours, wuss” he said as he lifted her in his arms and disappeared into what used to be my bedroom.

Chapter 3

It was the longest three hours of my life. They had left the lights on bright, and as the night turned pitch black I was put on crystal clear display for the neighbors. My pants were at my ankles, and my pink panties stayed at my thighs. I didn’t dare move.

I had never been spanked like that, and it stung so much more than I could have imagined. To make matters worse, I still had the awful butt plug in. I couldn’t help but think that my asshole was never going to go back to normal size again.

The three hours were almost up when the bedroom door opened and Don walked out. He was wearing just a pair of boxers, and there were little spots of lipstick on his neck from Steph’s sweet kisses.

He grabbed a marker from the drawer before walking over to me. I was finally going to be free. I was so relieved.

“How is your ass feeling, sissy?” he asked.

I muttered softly that it was very uncomfortable.

He just chuckled and gave my plug a little shove to make sure it was in deep before taking the lid off the sharpie marker and writing “CUNT” across my ass cheek. I could see what he was doing in the reflection of the windows, and I whimpered but held obediently still.

He gave my ass a few more smacks with his hand before speaking again. “You’re going to learn to never question me. And we’re going to start right now with you staying right here until midnight.”

I couldn’t believe it; that was two hours away yet.
“At midnight you may take your plug out and go sleep in my guest room.”
He said it without hesitation, knowing I would be obedient.

Steph called from the bedroom “come back in here you stud, stop wasting time on that wuss”.

Don chuckled and strode back to the bedroom and my beckoning wife.

——–

I woke up the next morning to the sound of a bell from downstairs in the kitchen. My ass was so sore and stretched. I slowly pulled myself out of bed and started my morning routine of showering and shaving.

My poor clit had ached longingly all night, as I couldn’t help but imagine my wife in Don’s arms, probably naked and dripping with his cum. I shaved very gingerly around it after finishing up my legs. The scrubbing to remove the demeaning sharpie words on my ass were useless. I cringed as I recalled the horror of being put on embarrassing display for the neighborhood.

When I finally made it downstairs, the happy couple had already finished eating their breakfast. They were still sitting at the table chatting.

Steph cheerily said good morning, and Don just waved a motion towards the dishes.
I was supposed to clean up.

I jumped immediately, wanting to be sure to keep him happy at all costs.

Steph was wearing only a t-shirt, and her nipples teased through the soft fabric as she flirted with her newly found lover. I had to avoid looking as I washed the dishes.

I noticed Don was writing a list out on his macbook, occasionally smiling and asking Steph questions. They talked quietly as I finished cleaning up.

“Crissy” he said, a little louder than I thought necessary.

“Why don’t you come join us?” It wasn’t a question.

I hurried to kneel beside the table, looking at the floor.
Steph wore an amused smile as Don spoke.

“Since I own this house now, I thought I should write up some ground rules.”

I squirmed but kept my mouth shut.

“Did you hear the bell this morning?” I nodded.
“The only way for you to earn your keep is to be our servant. When you hear that bell it means one of us has a job for you.”

I knelt quietly, blushing.

“Now this morning I rang the bell, and it was almost thirty minutes before you showed up. That will mean extra strokes added to your nightly spanking tonight.”

I started to protest. That wasn’t fair at all!

Don silenced me with a cold glare. I shut up and nodded softly.

“One of us will be giving you a whipping every night unless you earn the right to skip it, so be a good girl.”

Stephanie actually laughed at that one, her soft breasts bouncing under her shirt.

Don held up his key chain and isolated the smallest two. I looked longingly at the keys to my clit. What I wouldn’t give for just thirty seconds of relief.

“These are only going to be used on very, very special occasions” he said as he jingled them in front of me. “We’re going to start with one month, starting today. Any disobedience and I will add days or weeks.”

My heart sank.

Book two

Chapter 1

When Don finally left, almost two weeks later, my life looked dramatically different. My clothes had been mostly trashed, replaced with skirts, dresses, blouses, capris, and one ridiculous maid outfit they had me order online. I was thankful that I was still allowed to wear relatively masculine clothes to work, although under them I was wearing frilly panties and stockings.

I had cooked wonderful meals for Don and my wife each night, but my diet had been changed to nothing but salads, eaten after I had served and cleaned up after the happy couple. They wanted me as light and feminine as possible.

I watched Don drive out our driveway, my stupid skirt flopping around annoyingly from the breeze in the doorway. I knew he would be returning soon, but I was looking forward to life returning to normal for a little while. I turned to Steph, brushing the hair back from her face, preparing to kiss her.

She tilted her head, looking at me with confusion. She pulled back a little “Umm… I don’t think Don would like it if you kissed me honey. At least not as if you’re a man.”

Now it was my turn to be confused. “But you’re my wife.” I said, feeling kind of absurd as I stood there in a pleated skirt and flowery blouse.

She looked at me with pity. “Aww, you still think of it that way?”

I blushed, nodding.

She smiled softly “To be my husband you would still have to be a man.”

She consoled me as she spoke, rubbing my arm as I looked at the floor. “Haven’t you always wanted to be a sissy servant to me? I’m just giving you what you asked for.”

I blushed more, not sure what I wanted anymore. “Can I please be let out of my chastity cage at least?” It had been so long since my tiny manhood had felt anything other than the hard plastic that locked it safely away from me.

She smiled and brandished the small key. “Let’s go to the bedroom” She said with a grin.

I was so excited. I literally shook as I laid on the bed and let her chain my hands to the posts. I laid comfortably flat on my back as she slipped the key into the lock and unlatched it.

It felt unspeakably incredible as the case came off my little clit. It immediately stiffened to attention, begging to be touched.

Steph took her time, teasing me with just her fingernails and giggling at my tortured thrusts. It seemed like an eternity of excruciating teasing before she finally grasped my tiny member between her thumb and forefinger.

She looked in my eyes as she slowly stroked “You’re so big!” She said, obviously mocking. I didn’t even care as she continued, mockingly pretending that I was so much bigger and better than Don. I just needed to cum so bad.

Her stroking got a little faster, and I felt myself getting ready to explode. I couldn’t wait for that amazing feeling… that amazing relief.

I arched my back closing my eyes. I was about to float into ecstasy.
Suddenly Steph stopped stroking and just squeezed incredibly hard on my penis. Then, still firmly strangling my about-to-explode member, she started casually slapping my balls.

“Playtime is over” She said in a demeaning tone as I cried and begged and squirmed.

A few minutes later I was locked back up, wearing my skirt and cleaning the bathrooms. I couldn’t believe what I had been reduced to. I needed to do something to win her back; to show her I was still the romantic man who could sweep her off her feet. Our anniversary was in a month. Maybe I could plan a romantic trip, just the two of us, and get to be a man again.

That night i asked Steph if I could be allowed to use the computer. I was no longer allowed to just use the computer whenever I wanted.

Steph looked up from her book “what for?”

I looked down, pausing before speaking. “I was hoping to research places we could go on vacation to for our anniversary.”

She was quiet for a little while, thinking about it.

Finally she spoke up “Okay honey, that sounds nice. I would really like a getaway. Not with you though. I want to go on a nice relaxing, romantic trip with Don. Go find us somewhere nice to stay.”
And with that she returned to her book.

I looked through vacation destinations on the computer, my heart sinking as I looked at all of the beautiful beach photos, imagining my wife and Don enjoying each others company.

An hour later, I was entering my credit card information into a travel site. Don and Steph would be spending a week on the beach together over our anniversary. I cringed as I pushed the purchase button. The price really added up, and I would be left home alone while they enjoyed themselves.

Steph smiled approvingly before telling me to flip up my skirt for my bedtime spanking.

Chapter 2

Don of course loved the idea of taking my wife on vacation on my tab. I could hear the satisfaction in his voice as I politely asked him over the phone.

The next few weeks were annoying for me, with Steph packing and trying on her bikinis. Looking at her butt bounce in the skimpy swimwear was torture for my caged little dicklet. And every night ended with my face between her legs, eating her pussy as she moaned and dreamt of Don.

Don arrived at the house a few days before they were to leave. I wore my maid outfit when he came, and politely courtsied when he came through the door. I took his jacket as he embraced Steph and kissed her, holding her firmly in his big arms. I felt so weak.

He turned and acknowledged me before taking her to the bedroom, giving me a wink as he said “Good to see you, little sissy.”
I nodded nervously and thanked him as they walked into the bedroom.

I had already cleaned the house, so I didn’t really have anything to keep myself occupied. I just sat in the living room and listened to my wife screaming his name over and over.

I caught a little glimpse of myself in a mirror, and I was almost startled. The diet was really working, and the maid uniform was fitting me very well. The short skirt and long stockings were such a sexy combination. I walked closer to the small mirror, practicing my girly walk, my hips swaying and making the skirt bounce.

It all made me very horny. I needed release so bad. I never hated chastity devices more than ever at that moment. Almost at the point of tears, I just knelt on the floor and listened to the sounds of the lovemaking.

My pity party was interrupted by the ring of the bell, and I jumped to answer it.
I was surprised when I entered the bedroom to learn there wasn’t a creampie for me to clean up.

Steph was leaning on her arm on the bed, holding the sheet up over her breasts as if she felt the need to be modest around me.
Don sat on the edge of the bed facing me. He was completely naked, and his huge cock was still partially erect. It was an intimidating sight for me, and I just looked at the floor, feeling very small.

Don’s voice was confident. “I’ve been away from your wife for too long sissy. Her pussy has gotten tight, and she’s sore already.”

He spread his legs a little, reaching down to the floor and pulling the leather belt from the pants he had taken off earlier. “So it looks like the other girl in the house is going to have to be used.”

I shivered, looking at his thick cock. He smiled and motioned for me to come. “Panties around your ankles, slut. And then kneel.”

I did as he ordered, first pulling my panties down and then kneeling on the floor in front of him. I was shaking.

“Okay, you little cunt” he continued. “Time for you to use that little sissy mouth of yours.”

I hesitated for just a moment before leaning forward and hesitantly wrapping my lips around the head of his big cock. I had never done this before. It was so fucking big, and I felt like such a faggot loser sucking his cock in front of my wife.

I was just starting to take it a little deeper when I heard a whooshing sound and felt a sharp sting on my bottom. That’s what the belt was for.

“Take it all, you worthless bitch.” he said as he whipped me again. The leather stung like hell.

I took his cock deeper, tasting Steph’s pussy juices. I was only halfway down his shaft when the head of his cock pushed against the back of my throat.

My gag and subsequent reflex motion didn’t please him, and another cracker to my sissy ass ensued. This time though the skirt partially protected me. It was a relief to be partially shielded from the whipping, but I knew it wasn’t appropriate for me to let my skirt get in Master’s way. My mascara ran down my teary cheeks as I lifted the back of my skirt up to my lower back, holding it there so Don would have a clear target on my sissy bottom.

He continued fucking my throat hard, whipping my ass any time he felt a little tooth or if I went too slow.
I cried and gagged and squirmed as I did my best to take his huge dick. It wasn’t pleasant for me in any way.

Finally he pulled out. “You haven’t earned the right to take my cum in your mouth yet, cunt. So lean your head back and keep those little slut eyes wide open.

I did as he said, still crying and gagging.

I knelt there obediently as he stroked his cock, holding the head just above my left eyeball. I knew what was coming, but I was obedient.

I had a closeup view as his enormous rod shot a big load directly into my eye. After a few seconds he switched to the other eye, making sure it got a good dose too.

I cried and sobbed, the cum stinging as it dripped across my eyes and down my cheek, taking mascara with it.

Chapter 3

I knelt helplessly, my hands obediently behind my back, as I watched Don empty the contents of my leather wallet onto the kitchen table.

“I don’t think you’ll be needing much of this while we’re gone, crissy” he said with a little chuckle.

I nodded, cowering under his glare.

“Go get the little girly purse Steph bought you” he ordered.

I jumped up and ran to get it, clutching the pink leather as I came back and knelt again. I had to admit it was kind of a cute purse, with little flowers on it and a dainty shoulder strap.

He instructed me to hold it open as he started picking through the contents of my wallet, spread across the table.

I was relieved as he threw my drivers license and insurance card into the purse.
He hesitated though as he picked up the blue and grey credit and debit cards, grinning at me before sliding them into his own wallet. My face turned bright red. I was trembling, hoping he was joking.

But he wasn’t.

All that was left on the table was the eighty or so dollars in cash. He picked it up and counted through it, flipping it in his fingers.

“There’s plenty of food in the house Crissy, so I’m not sure you need any of this while we’re gone. But hey, I’m feeling generous.”

He tossed a five into my pink purse.

“Maybe go buy yourself some new eyeliner or something” he said, as I blushed even redder.

My week had gone from bad to worse. After the humiliation of having to suck a cock, Don had decided that my male clothes would all be locked away until they got back from vacation. I didn’t have to go to work during that time, but it meant I was going to be stuck at the house unless I wanted to go into town dressed in one of my girly outfits. Now I couldn’t even buy anything online without the credit cards.

“Don’t be so sad, Crissy” Don said as he slid the wallet into his pocket. “You’ll finally be able to get out of your chastity device after we leave.”

“Really?” I said. I wanted to cum more than anything else in the world. I needed it so so bad.

“Sure Crissy.” he continued. “We gave the key to one of the neighbors. All you have to do is go ask them for it.”

I gulped. “Which neighbor?” I asked.

Don smiled. “That I can’t tell you. You’ll have to go ask them all.”

I froze in terror at the thought of walking around the neighborhood, wearing one of my stupid outfits; knocking on each door and asking if they had the key for my clitty tube.

—-

Words cannot begin to describe the crushing humiliation I felt as I walked up the street, led by the screaming desire of my little penis to be free of its cage.

Don and Steph had driven to the airport a few hours before, and already I had fallen into their plan of showing me off to the entire neighborhood.

Why did all the skirts they bought me have to be so short? I was wearing the longest one, and it only went halfway down my thighs. I felt so exposed with my bare shaved legs on display as I walked up to the first house. At least the blouse wasn’t too ridiculous, with only a few little ruffles accenting the baby blue satin.

I had no idea what to say as the first neighbor opened the door. I completely froze and thought I would die as she suppressed a laugh. I mumbled something about a key, and she obviously had no idea what I was talking about.
Completely flustered and humiliated, I ran off just as quickly as I could in my stupid skirt and heels.

I spent the next hour methodically humiliating myself in front of all my neighbors. I was starting to wonder if any of them actually had the key as I walked up to Tom’s house. I was tempted to skip his house altogether, remembering our little argument at the annual POA meeting a few months earlier. He was such a jerk. He deserved the harsh comments I had made.

When he finally answered the door, a big smile spread across his face.

He invited me inside, and I knew I was in deep shit.

I held my knees together like a lady as I sat on his couch. Tom lived alone, and the house was dark and a little musty.

“I’ve been looking forward to this ever since Stephanie brought me your key and explained your situation.” he said with a terrifying leer. I hated him more than ever.

He leaned back in his chair, his gut protruding slightly. “I’ll give you the key, but first you’re going to have to earn it.”

I didn’t like the sound of that at all.

Chapter 4

I spent the next several days trying to earn my release from Tom. He put me to good use: scrubbing the floors, dusting, scouring the toilets, and anything else he could think of. All while he sat and watched tv, occasionally shouting crude slurs at me. Every time I considered quitting, my poor little penis would squirm and beg me to keep working. It had been months now.

And since I didn’t have the password any more for the computer at the house, Don would email photos every day to Tom of his adventures with my wife. Tom would ridicule me as he showed me the photos, revelling in my misery. Steph looked so gorgeous in those skimpy bikinis, my dicklet ached and leaked longingly.

Finally, after four days of miserable work, Tom told me I had almost earned my release. My heart skipped a beat.

But almost was the key word.

“You embarrassed me in front of the entire neighborhood, so you’re going to be punished for that in front of the entire neighborhood.”

I could tell he had thought about this for a while. As he described my punishment I started to beg him for an alternative, but he wouldn’t be moved.

And so, with bright red cheeks, I stood in front of him, my hands clasped tightly in front of my skirt, and spoke as he filmed me with his cell phone. I imagined the reactions the neighbors were going to have when they saw the video as I spoke.

“Dear neighbors. I was rude and disrespectful to Tom at our last meeting, and I would like to apologize for my behavior. And also, I have asked Tom to please discipline me as retribution for my rude and childish actions.”

Tom set the phone on a coffee table, facing the kitchen, as I bent over the table and pulled down my panties. My face was turned towards the camera. Tom wanted me to look directly at it while I took my discipline.

He used a big paddle with holes in it. He didn’t tell me where he got it. Regardless, it did the trick. I looked into the camera as he paddled my ass, thanking him after each stroke and asking for another. The force of each swat made me gasp and bounce, and I had tears running down my cheeks almost immediately.
My bare legs trembled, and the sting on both my bright red ass cheeks and my pride was horrible. It was all I could do not to try and run away. But I held my place, squirming at each awful stroke.

When he finally decided I had had enough, I stood and courtsied, thanking both him and the neighbors.

“Okay crissy” he said after hitting send on the email to everyone in the neighborhood. “You get to cum now.”

—-

I walked with trepidation towards Tom’s little shed/woodshop. Happy stories never start with a helpless girl being dragged into a shed.

My heels kept getting stuck in the dirt as I walked, forcing me to bend down. Tom gave me a look I found very disconcerting as I would bend down to put my shoe back on. I pouted and pulled my skirt down, not enjoying his leer.

He flipped the light on, revealing a floor covered in sawdust and a lot of partially completed woodworking projects. Tom didn’t say anything; he just pointed to the far end of the room.

Standing by itself was a homemade simple set of wooden stocks, with a hole for the head and two smaller holes for the wrists.

I shook my head, stepping back. He grinned, pulling his keys out of his pocket and jingling them in front of my face. “You want to cum, Crissy?”

Again, my caged penis betrayed me, and a few minutes later I was trapped firmly by the homemade stocks. I winced as the hinged board closed shut, and the hefty padlock snapped closed with a sickening click.

The stocks were mounted at waist height. My back was horizontal with the floor, and my legs were spread slightly to make it less uncomfortable. I kicked off my heels, only to be swatted hard across my thigh as Tom told me they were to stay on.

Facing the wall, all I could see was a small mirror he had positioned so I would be able to see myself somewhat. I wiggled against the heavy wood helplessly.

My mood was instantly lifted though as I felt Tom fidgeting with the lock imprisoning my little clit.
Suddenly I was free. It was incredible. I was instantly rock hard, and Tom chuckled. “They weren’t kidding, that thing is tiny. No wonder you’re such a little douchebag.”

I didn’t even care. I just needed to cum.

Tom stood up, speaking as I heard him unzip something. “Okay crissy, this is how it’s going to work. I’m going to fuck your little ass, and you can cum from that if you want to. If not, I’m locking your little thing back up.”

I whimpered, stomping my heels on the floor and trying to hump the air with my desperate little penis.

“Beg me for it crissy.” he said confidently. “Beg me to fuck your little ass and make you cum.”

I clenched my fists in helpless frustration as I quietly muttered “Fuck me”. I was so horny.

“Louder!” he commanded. “Beg me like a little slut or the cage is going back onto your little pecker.”

“Please” I said louder. “please fuck my ass. Don’t lock me back up. I need to cum so bad.”

He was quiet, waiting, so I continued. “please please… pump my ass with your cock….make me your slut.”

That seemed to be what he was looking for. He stepped around the front of the stocks and pushed his cock in my face. It wasn’t as big as Don’s, but I still gagged as he pushed it between my lips.

The blow job warmup didn’t last long. He ripped off my panties and skirt, leaving me naked except for my blouse and heels. He smacked my ass a few times before pressing the head of his cock up to my cherry.

He had me beg again as he slowly pushed into me. I watched my own face in the mirror, mortified, as I felt his dick slide inside me.

He grabbed my ass cheeks with both hands, squeezing and pinching as he started to grind. I moaned loudly, embarrassed that it actually felt kind of good. I closed my eyes, feeling his rod thrust in and out.

It didn’t take long for me to cum. I felt it oozing out from the tip of my clitty in little spurts. I rocked my hips, desperate for a little bit of sensation on my penis, but it was no use. My cum oozed out without any of the usual amazing orgasm feeling.

I needed more. It wasn’t satisfying. I begged him to fuck me harder, and he did. I caught the occasional glimpse of myself in the mirror, my face bouncing as he slammed into me again and again.

I spurted a little more, but it was even less satisfying. I cried as I felt him slow and push as deep as he could, moaning as he shot his load into my sissy ass.

“Good girl” he said as he pulled out.

There was no cuddling. The penis cage was locked back on without ceremony, and he smacked my thigh one more time as he walked out.

I was left alone, locked in the stocks, with cum dripping out of my ass and down my thighs.

I watched myself cry, mascara running down my cheeks, unable to accept how much I enjoyed being fucked and how much I wanted it to happen again.

Chapter 5

I knelt on the wood floor, focusing every bit of effort I had into pleasing Tom’s hard cock. I looked up at his face as I sucked, hoping against hope that he would reward me by taking my ass again.

After spending what had felt like an eternity locked in chastity, it had been at least somewhat of a relief having my ass fucked. Getting that feeling of release again was all I could think about.

But in the two days since he had taken my cherry, Tom hadn’t given it to me again. Instead, he was making me earn it. I spent hours at his place, cooking for him, doing his laundry, and spending a lot of time with my lips wrapped around his dick.

I wondered what it must be like to have someone giving you blowjobs on demand. It sounded really wonderful. I imagined myself from his perspective; a desperate slut, eagerly sucking cock and begging to have her ass fucked.

I had taken extra time on my makeup and outfit before going over to his house. My frilly little skirt and white stockings were sooo embarrassing as I had walked through the neighborhood to his house, but I wanted to look as slutty as possible.

So as I knelt between his legs, I raised my ass and swayed it side to side. I could feel my little skirt bouncing, barely covering my sissy bottom.
I was learning what it meant to be a desperate bimbo.

For his part, Tom was happy to relax in his chair with a little slut worshipping his cock. He grabbed the remote beside the chair and flipped on the TV. I moaned as I realized I would be sucking his cock for a long time as he used me without any consideration to my needs.

I walked home that night dejected and tired. I was thankful for the twilight dusk, hiding me slightly from the neighbors’ eyes. Don and Stephanie would be home in just two days. I shuddered in dread at the thought of Steph finding out what a slut I had been.

When I got home I immediately got my dildo and dreamed that it was a real cock as I eased it up my ass. But having felt a real dick, it was a let down. I still managed to squirt a little in my clit cage as I stroked the dildo in and out of my hungry ass.

I went to sleep, dreaming of new ways to earn a real fucking.

—-

I was disappointed Tom didn’t reach for his key chain when he told me to take off my panties and get on all fours on the rug in the center of the living room. I wasn’t going to be allowed out of my chastity tube this time.

It had taken far more hours on my knees between his legs than I cared to think about to earn my second fucking. I trembled in anticipation as I waited on all fours, spreading my stocking-clad knees on the floor. I pulled my tiny denim skirt over my ass for him. I had gotten in the habit of thoroughly shaving myself every night, and I hoped he liked what he saw as I swayed my smooth backside.

I wasn’t looking back, so the forceful blow from his palm across my thigh caught me off guard. I yelped as he reprimanded me. “Hold still bitch. You’re not as sexy as you think you are.”

I obediently stopped, embarrassed by his put down. I just moaned softly as he grabbed me with both hands and pulled my ass onto the tip of his cock. I was grateful for the twenty minutes I had just spent moistening and warming up his rod.

My own little manhood was as stiff as it could get in its little trap. I tried not to think about it and just focus on the sensation of the warm cock easing into my ass.

I slipped into sissy delirium as Tom started thrusting in and out, holding me firmly in position. As he started speeding up, he occasionally smacked my ass, reminding who was in charge. I let out a girlish little yelp each time.

As he slammed into me, I felt the familiar pulsing as the pressure on my prostate started the cum oozing out of my little clit. And the same familiar feeling of frustration accompanied it, as I was milked without any feeling of satisfaction.

Tom verbally abused me as he fucked my asshole, telling me I was just an ugly bitch to be used and thrown away. I cried and nodded my head meekly, wishing I was prettier. I would work harder. I would become a perfect slut.

I arched my back and moaned softly, hoping he was enjoying using me.
He didn’t say anything to confirm his enjoyment, but soon a load of sticky goo filled my asshole.

I thanked him as he pulled out of me, wishing it had lasted longer.

Any afterglow was immediately squelched for me when he noticed my little cum puddle on the rug.

“Did I tell you to cum?” he demanded.

I cried and shook my head as I lowered my head and tried to lick my cum as it soaked into the rug fibers.

“You’re a useless, stupid little cunt” he went on, reaching from behind and grabbing my balls as I licked the floor.

I squealed as he held my precious little balls in place with one hand and slapped them again and again with the other.

I tried to continue licking my cum as I sobbed, the pain shooting through me at each swat. I started begging him to stop through choking tears and sobs.

When he stopped I was a mess. I fell to the floor, crying uncontrollably. He just watched me, shaking his head.

Ten minutes later, when I was able to gather myself, I knelt in front of him again and thanked him for fucking me. I felt his cum oozing out of my ass onto my thigh as I lowered myself to kiss his feet.

I heard him unzipping his pants, and I knew what to do.

While he turned on the game, I got comfortable kneeling between his legs and spent the next two hours gently worshipping his balls.

Chapter 6

Telling Stephanie about my week with Tom was like two girls talking about their love life. I felt like I should be in a giggly tone as I told her in a hushed tone that Tom had made love to my ass twice.
She was so curious. “Do you like it?” She asked. “Do you like it when he has sex with you?”

I blushed and nodded. It was so humiliating, but she also seemed so genuinely happy for me.

When it was her turn to talk about making love with Don, she expected me to act like a silly girlfriend. She leaned in, her tanned cleavage tantalizingly close to my face. Her sun-bleached hair curled around her shoulder. It was driving me crazy.

She bit her lip playfully, going on to tell me about not getting a wink of sleep the first night at the beach. It was torture listening to her recount the amazing sex they had on their trip. I wished so much I could fuck her pussy right then and there. A little squirm of my penis against its tube reminded me that wasn’t going to happen.

She was in the middle of telling me about how Don wouldn’t let her wear panties the entire trip when when we were interrupted.

“Sorry girls” Don said as he walked up, towering over me. “But little Crissy needs an inspection.”

I submissively nodded my head and stood up, lowering my eyes and blushing as I pulled down my skirt and panties, followed by the frilly blouse and bra.

I stood obediently in the inspection position, completely naked except for my heels, my legs spread as I stood, and my hands on top of my head. He took his time, roughly feeling my legs and crotch for even a single hair or bit of stubble I might have missed while shaving.

I shivered. It was so humiliating.

The smack to my ass wasn’t unexpected, but it still elicited a little whimper from me. The whimper turned into a moan as he spread my ass cheeks. I was becoming such a slut.

“Good girl” he said as he gave my cheek another slap. “Now go to the bedroom; I bought something for you.”

I didn’t think it would be wise to correct him by telling him that since he had probably used my credit card that I had actually bought it, so I just scampered into the bedroom and returned a moment later with my new “gift”.

No words were exchanged. He just spun me around and bent me over. I didn’t resist.

He inserted the black tip into my gurl pussy and gave it a solid shove. I knew better than to move as I heard the pumping sound.

“It’s an inflatable plug, faggot” he said as he squeezed the pump. “But I guess you already figured that out”

I was quickly figuring out that inflatable pumps were straight from hell. I started whimpering and begging, squirming like a helpless animal.

When he finally decided it was stretching my unfortunate asshole enough, he stopped pumping and told me to go get duct tape from the shed.

I ran, still butt naked, across the yard to the shed and got the duct tape. When I got back, he had me hold my arms together high behind my back close to my shoulder blades and then taped them firmly in place, wrapping around my wrists again and again. I sobbed, knowing there would be no chance for me to reach down and find the release valve to the plug.

“I missed you” he said with a wicked smile as he used another piece of duct tape to seal my mouth shut.

Book Three
Chapter 1

I looked at Steph, my face red with a combination of fear, anger and embarrassment. I was absolutely not going to stay in my sissy maid role when her mother came to visit.

I stomped my black heels on the floor and crossed my arms defiantly. I had to draw a line somewhere. The neighbors all obviously knew what I had become, and even that was far more publicity than I was comfortable with.

Steph just quietly started counting “one… two…”.
My resolve melted, knowing that reaching ten meant an extra month in chastity without relief. It was her trump card, and she knew it.

Don had given my little clit freedom for a glorious ninety seconds before leaving to go home. I had knelt on the floor and wanked, not even caring that they were sitting on the couch and laughing at me.

Every day since then I had done everything in my power to earn another release before the prescribed three months. Having two extra months added was horrifying.

So before Steph even got to six, I was kneeling on the floor in front of her, kissing her toes and begging her to not add any time to my chastity sentence. She said “Good girl” and told me to go get my ballgag.
I did the rest of my chores that day with my lips wrapped around the plastic of my gag, relieved that my punishment wasn’t worse.

Three days later I found myself shivering nervously as I walked to answer the door. Even though I knew Steph had told her mother all about our new arrangement, I couldn’t help but feel an enormous amount of shame as I pulled open the front door.

After months of wearing my maid outfits at the house, I had gotten very accustomed to the feeling of stockings and skirts. But standing in front of my mother in law in my silly little outfit brought fresh waves of humiliation that struck me surprisingly deep. It wasn’t a good feeling. As I timidly courtsied, I felt a girlish angst sink in.

For her part, Steph’s mother was very kind. There was no laughing or undue disparaging. It was almost as if it seemed really natural to her that I would be a submissive feminine maid. I served her and Steph drinks and did my housework as usual, letting the girlish feelings soak in. I could almost feel my testosterone evaporating as I scurried about the house, my heels daintily clacking on the wood floor.

Somewhere in the process I found my sissy space, and started almost enjoying my role. When I slipped up and accidentally dripped a tiny bit of hot tea on Steph’s mom as I poured, I felt genuinely disappointed in myself.

And even though I had been trained to request discipline after making mistakes it felt so natural this time.
After rushing to clean her up and offer effuse apologies, I stood back with arms held politely in front of my skirt.

“Please Miss, would you be so gracious as to offer discipline for this clumsy maid?”

I didn’t even blush much as I asked. It just seemed like the right thing to do. She looked up from the chair and smiled as she nodded softly.

I rushed to the bedroom closet to fetch the cane. I didn’t want her to be inconvenienced, so when I came back I carefully positioned myself off to her side so she wouldn’t have to move.

I almost felt a little sense of pride in my training as I pulled down my white lace panties and bent over.

“How many do you want, sweety?” She asked, and I politely asked for a dozen.

I let out little girlish yelps with each stroke, letting her know she was doing a good job. I focused on the mental image of the tea pot, wanting my discipline to teach me to serve better. By the last stroke I was genuinely distressed, jumping and quivering each time the horrible cane swished through the air and left a hot stinging line on my naked cheeks.

Pulling my panties back up, I thanked her genuinely. And as I went back to work, I embraced the shame, the humiliation, and the sting on my sissy ass. I felt so weak, so exposed, and I wondered if I would ever feel any other way.

Chapter 2

The weeks following Don’s return to his home were hard for Steph. She was getting accustomed to having his big cock inside her every day, and suddenly it was taken away from her.

I heard her talking to her mom as I was cleaning up the kitchen. I pretended not to hear.

“It’s driving me crazy” She said to her sympathetic mother. “All those years wasted with Crissy’s little thing. And then when I finally get a big cock, he’s gone again after just a few weeks.”
I felt genuinely bad for her, knowing she had spent the first years of our marriage pretending to enjoy sex. I wished there was something I could do.

That night after getting the house all cleaned up and set for the next day, I went to the living room where Steph and her mom were drinking wine and talking about some tv show. I didn’t want to interrupt, so I just courtsied and stood awkwardly beside the couch, hoping they would notice me waiting.

They didn’t. I had become like a pet, or maybe worse. They completely ignored me. Finally I cleared my throat. They both looked at me, surprised.

“What is it?” Steph asked. “Need another spanking?” her mom piped in. I blushed, still feeling the stripes from earlier that day.

I answered quietly “May I have a word, Miss Steph… in private?”

She shook her head, obviously not wanting to get up from the couch. “Anything you need to say you can say to both of us, sissy.”

I squirmed, blushing more now. “Well, err.. I know you’re missing Don, and…” I couldn’t stop stammering. I wasn’t prepared to say this in front of her mom.
“I… I thought maybe I could please you… while you talk with him on the phone.”

Steph looked concerned. “Honey, are you asking me to let you out of chastity? That is so rude. You know Don said you’re only allowed out for cleaning until he gets back. I’m going to have to tell him about this.”

“No, no Miss… that’s not what I meant!” I interjected. “Just with… you know, my tongue.”

Steph relaxed, smiling now. “Ah, I see Crissy. That’s actually a really sweet idea.”

I blushed, seeing her mom’s amused smile.

That night I spent an incredibly frustrating hour between Steph’s thighs, my face buried in her pussy as she talked dirty with Don on the phone. I couldn’t hear what he was saying, but I could tell when he said something she found especially hot as she would grab my hair and pull my face harder onto herself and grind against my mouth.

When she finally hung up the phone, I could tell she felt better. The tension was gone as she rolled over and closed her eyes; ready to sleep.

I was glad she was happy. It gave me a feeling of sissy satisfaction. But I was also unbelievably horny. I went to the basement to my maid’s quarters and tried to sleep, but my little clit refused to calm down. I whimpered as I humped the bed, exasperated and desperately needing to cum. But I couldn’t feel anything through my clit cage, and the pinching in the little tube was making my eyes water.

I looked at the clock. It wasn’t too late yet. Tom was probably still awake.
I threw on a satin nightie and quietly snuck out the back door.

When Tom opened his front door, I instinctively sank to my knees, ready to beg. I needed my ass fucked so bad. It was the closest I could get to a true release from my chastity frustration. I looked up with puppy eyes at him, hoping he was in the mood.

He was in boxers and a wife beater, obviously about to go to bed.
Rather than say anything, he just walked back to his bedroom, leaving the front door open. I took it as an invitation and crawled after him.

He smiled and said something about his horny little stupid slut as he laid back on the bed.

I crawled between his legs, knowing that I would have to warm him up with a little blowjob before he would take my ass.
He crossed his arms under his head and relaxed as I pulled down his boxers and took the head of his cock into my lips. Even after a few weeks of being his bitch, I still recoiled each time I felt his penis on my tongue. But I needed to turn him on so he would milk me with that same rod, so I pushed past the feelings of shame and took the whole shaft; sliding my tongue along the bottom of his stiffening cock.

After getting him totally hard, I leaned back, wiggling my ass. I was so excited to feel that cock inside me and feel the blessed relief of my cum slowly oozing out of my clit as he pumped me.

But Tom opened his eyes just long enough to look at me and tell me to get back to sucking.
I whimpered but obediently went back to worshipping his dick.

My concern increased as he started thrusting, pushing his cock into my throat. Every time I tried to slow down he just slapped my face, called me a stupid slut, and told me to shut up and suck.

I was devastated when I realized that all my work wasn’t going to earn me my release. His thrusts got longer and deeper, and I knew what was coming.
Tears of frustration and disappointment trickled down my face as I felt his cum shoot into my mouth.

I continued crying as he drifted off to sleep, obediently licking his balls until I heard him start to snore.

Chapter 3

I sat nervously on the edge of the dark leather chair, clutching the ballpoint pen as the lawyer spoke. Steph was nodding confidently, but I felt much less certainty.
She had allowed me to wear a pair of slacks and a light blue blouse, along with some neutral flats and a nondescript handbag. It was still humiliating to be seen in public like this, but it was at least much less feminine than it could have been.

The lawyer wore a crisp power suit, and the contrast between him and me didn’t help my feelings of discomfort in the situation.
He was a former boyfriend of Steph’s, and I didn’t like the way he looked at either one of us. He knew all about our situation, and it was obvious from the smug look on his face that he enjoyed seeing me in the predicament I was in.

When Don had finally convinced her that I shouldn’t be able to control our finances any more, John was the one she went to for advice. Once he had gotten over the unusualness of the situation, he had started putting together a plan for us.

I glanced over the paperwork as he explained the details. The heart of the agreement was a document saying that I was requesting Don to become a trustee of my estate, and changing my status to beneficiary. This meant that at a whim, Don could revoke my privileges to the bank accounts, cars, or even the house.

I looked at Steph, a little shocked at how drastic the agreement was. “Miss, if I may speak please” I said softly.

John chuckled loudly and then promptly apologized, although I could tell he didn’t mean it.
Steph just smiled and nodded, so I continued. “Please Miss, this gives Master Don the ability to leave me penniless and kick me out on the street!”

She grinned. “Well then, I guess you’d better behave and be a good little sissy.”

I shriveled, my face reddening as she continued. “And besides, I’m also going to be a trustee, so I have some say too.”

This was obviously a power trip for her too, and I wasn’t going to go through with it.
She saw the look of defiance on my face and started pulling her phone out. I jumped in my seat. “Please don’t call Don!” I said, not wanting him to know I was resisting. But it was too late. I whimpered as she started talking to him. I had long since ceased to have the balls to stand up to him in any way.

She put him on speakerphone.

“Crissy, this isn’t what I want to hear. Does there need to be consequences, or are you going to be a good little sissy and sign the paperwork?”

John was obviously trying to hold back laughter as I profusely started apologizing. Even from hundreds of miles away, I was terrified and completely obedient.

Don waited a moment before interrupting me. “Good girl Crissy. I can tell you want to do the right thing deep down. You do know the right thing is for you to be a powerless sissy, don’t you?”

“Yes master.” I said softer.

Steph switched the phone over to video Skype so Don could watch me sign the papers.
I had never felt such complete defeat. As I signed, I started to cry softly. There was no being brave. I was finally utterly owned.

—-

It’s hard to put into words how emasculating it was to walk into the house, knowing I was now living there by permission. Don could kick me out at any point. I didn’t think he would actually do it, but knowing that I was helpless and at his mercy was such a terrifying reality.

The whole affair had made Steph far hornier than I had expected. Almost as soon as we were inside she told me to strip naked as she propped herself on the couch and pulled up her skirt.
A year earlier that would have been the signal for me to come fuck her, but in my new reality it meant it was time for me to kneel between her legs and get to work pleasing her with my tongue.
Usually I at least somewhat enjoyed pleasing her, but this time was different. It was going to take a long time for me to emotionally recover from my devastating defeat at the lawyer’s office. I wasn’t actually sure I would ever recover. So I closed my eyes and licked like a good sissy, imagining how good it must have felt for Don at that moment.

Steph came again and again, writhing herself against my extended tongue. I couldn’t help but gradually get turned on, only to have the familiar feeling of abject frustration when she was finally finished with me.

She had me fetch her a drink as she composed herself. As I came back she told me to kneel and listen to some of the fun new rules she and Don had thought of.
I obediently knelt beside her, wishing she would have let me put some clothes on first.

She started laying out the fresh set of rules now that I was officially living in the house by Don and Steph’s permission. It was the kind of stuff that I would have fantasized about years before, but as I knelt on the wooden floor, the reality was unsettling.

I could tell she was enjoying herself as she read from a list on her phone.
“First, you will still be allowed to access the bank accounts, but only for paying bills and buying groceries and gas. For all other purchases, you will have to ask permission from one of us.”

I started to interrupt, but she silenced me with a motion of her finger and continued.

“We’ve decided to be generous and give you an allowance of ten dollars a week, even though you should really be paying us for the privilege of living here.”

She paused for a moment, leaning back further on the couch and pointing to her ass. I crawled between her legs again and started worshipping her asshole as she continued.

“That ten dollars is only if you’re good though, Crissy. I’m guessing most weeks it will be less, since you’re really not a very competent maid.”

She pushed me away and told me to go get a cane. I didn’t protest, even though I had no idea what I had done wrong to deserve the cane.

When I came back, she pointed to her ass again. I handed her the light brown slender cane before kneeling again and resuming my slow worship of her little asshole.

“Now Crissy, I know you used to fantasize about having your little ass whipped, didn’t you?”

I whimpered and nodded as I licked.

“But you don’t enjoy them very much in reality, do you?”

“No miss” I mumbled. In fact, I had grown to hate the discipline. A sore bottom was a fun fantasy, but the reality of bright red burning cheeks was anything but fun.

“Good girl, Crissy.” She said, grabbing my hair and pulling me in deeper between her ass cheeks. “That’s what I thought. And that’s why the promise of a good twenty strokes every night before bed should be a good incentive to try and earn the right to go to bed without a sore bottom. It will be up to you to find a way to go above and beyond your maid duties to lessen the number of strokes you get at bedtime.”

I was on all fours, my face buried in her ass as she talked. Occasionally she would flick the cane across the top of my naked ass. It was enough to make me yelp each time.

“Okay good girl” She finally said, pushing me back. “Now stand up with your sissy legs spread and your hands on your head.”

I leapt up to assume the instructed position.

“From now on you will wear one of your maid outfits at all times. Even when we leave the house.”

I winced. She noticed and gave me a little flick with the cane across my inner thigh.

“The only exception is your work, where you will be allowed to wear slacks and a blouse. But as soon as you get home, it’s into the maid uniform right away.”

I nodded submissively.

“Also, Don and I expect your ass to be plugged at all times while you are on duty. If I find you here without a big plug up your ass, I will whip your little sissy balls immediately. Understood?”

“Yes Miss” I said submissively.

“Good girl Crissy. The rules start immediately.”

I didn’t hesitate. Five minutes later I had a big rubber plug up my ass under my pink maid dress. I had a lot to think about as I squirmed my ass and worked on the laundry.

Book Four

Chapter 1

I crossed my arms behind my back, the weight of my torso now resting on the kitchen table.

“Legs wider” Steph said in a businesslike tone.

I obeyed, my heels clicking on the wood floor as I adjusted my weight.

I had worked so hard. But apparently not hard enough to avoid the pain and embarrassment of bending over the kitchen table with the blinds open for the neighbors to watch.

Steph flipped up my skirt, the frills bouncing as they exposed my little white bottom.

I squinted, waiting for the first stroke.

I squealed loudly as she snapped a solid stroke across my upper thigh, taking my breath away.
A second mean slice followed almost immediately, making me jump and bite my lip so I wouldn’t cry.

Steph leaned down, rubbing her finger along the red stripe she had just created.

“You want me to be happy, don’t you sweety?”

I was taken back by the question. She spoke in a soft neutral voice as her nail brushed my sensitive stripe.

“Yes Miss, of course I do” I said, not sure where this was going.

“Ass up” She said before giving me three more. I managed to keep my back arched and ass raised for all three. She liked having her target lifted like that.
I did cry this time, but I tried to stifle it.

She went back to stroking my tender ass. “I’ve been craving something. Do you think you might know what it is?”

I didn’t.

She reached further down, creeping her fingers closer to my little balls. “I’ve been craving a baby, honey.”

She gave a pause for the words to sink in. My face turned white. We hadn’t talked about having kids in over a year; certainly not since Don had been in our lives.

“I think you’ll be so good with kids, sweety. Don’t you think so too?”

I didn’t know what to say, but I nodded.

Her fingers crept to my shaved little testicles, and she started rubbing her nails along them. “But I don’t think it would make sense for my little Crissy to try and impregnate me, do you?”

That actually sounded kind of wonderful. I hadn’t felt pussy in close to a year now.

She gave my balls a little squeeze. “Do you think these little things should be used to make a baby?”

I looked at the reflection of myself in my skirt and blouse in the window. It wouldn’t be fair to any kid to have a father who was as weak as me. “No Miss. I don’t think that would be a good idea.”

“Good girl” She said, giving my balls a playful slap.

I gave a girlish little moan.

“So who do you think I should have a baby with then, crissy?”

I didn’t like where this was going. I was quiet for a few moments. I started to cry defeated tears as I heard the words coming out of my mouth.
“You should have a baby with Master Don, Miss.”

—-

Any neighbors who walked by would have seen a sight that they had become accustomed to by now: a maid bent over a table, squirming and crying as the lady of the house reddened her little ass with a cane.
What they wouldn’t have been able to observe was just how special a moment this was between the maid and her mistress.

I couldn’t have predicted the flood of emotions that came over both of us as Steph raised stripe after stripe on my quivering ass and thighs. This wasn’t punishment any more. I had surrendered at a deeper level than ever before, and the whipping was just a demonstration of the connection we felt.

My thirty minutes in the corner were unusually long this time. My mind started racing. There was so much involved in having a baby. Was I ready for this. Would I ever be ready for this?

But the idea of having Don’s baby didn’t cause any lack of certainty in Steph. The moment my thirty minutes of corner time was up, I was ordered to the bedroom by a very horny and already naked wife. We made the most passionate love of our marriage so far. I lost track of her orgasms as I licked round after round. There was something primal in her that was excited beyond words. I loved seeing her so aroused, even if it was frustrating for me to be completely without release.

Finally she calmed down. My neck and jaw were sore. I curled at her feet, softly kissing them as she fell asleep.

The next morning, she was on the computer, looking at baby pictures on pinterest. I couldn’t help but feel deep cucky angst as I imagined her holding Don’s baby in her arms.
We had a full two months until Don was coming to visit us again. Maybe she would have a change of heart by then.

The two months passed frighteningly quickly though, and it got worse instead of better. By the time Don arrived, Steph was in a total baby craze. I was surprised though to learn that she hadn’t mentioned a word to Don.

She wanted me to be the one to ask.

She interrupted their usual little make out session with him grabbing her ass as he walked through the door. She looked at me as she held his muscular arm. “Crissy has something she would like to ask you.”

Don looked at me, a bit glaringly at having been interrupted from groping my wife in her tight shorts and tank top. I immediately blushed red. Why did I feel so incredibly weak around him? I was like a fearful puppy who shook and wet the floor whenever the bigger dog so much as looked at him.

I looked down, adjusting my skirt and fidgeting.
I knew what Steph was looking for.

I squirmed as I knelt, looking up only briefly before cowering under Don’s glare again. “Master, Steph… err… both of us have been thinking that, um, it would be…”

I felt so flustered, so weak, my lips were dry.

I looked at Steph, her arm intertwined with his; her shoulder nestled into his side. She wanted this so much.

My eyes watered as I tried to compose myself. “Master Don, we would be honored if you would be willing to impregnate Steph.”

Don looked at my wife, who beamed up at him.

I continued, my voice faltering a little less. “She has been off birth control for two months Sir. Would you consider being the one to breed her?”

By the time I finished my sentence, their lips were locked in a deep, passionate kiss. I looked at the floor, feeling like a very unnecessary third wheel.

Chapter 2

Watching Steph spread her legs on the bed brought a rush of overwhelming and contradictory emotions to my sissy brain. She looked so perfect; her blonde hair cascading on the pillow, her tanned thighs toned and held willingly up in the air, begging to have a big man hold her down and give her a baby.

Part of me knew this was how it was meant to be. But another part of me wanted so badly to be the one to be on top of her, thrusting deep into that soft fertile pussy.
I looked down between my legs. My tiny one was making a noble but useless effort to rise to the occasion as it pushed against the confines of it’s little tube.

I tried to remember what it felt like to be inside a woman.

Don was taking off his pants. Seeing his rod stiffen made me bristle with envy. Maybe in another life I could have a dick like that.
He hovered over my wife on the bed, their eyes locking for a moment before their lips met. Steph was savoring this. She nibbled and moaned, lifting her hips from the bed, begging to be penetrated.

Don’s cock was rock hard, it’s big head hovering inches from her hungry pussy. The tattered remnants of my masculine pride were putting up a fight. It was so hard to watch another man take the ultimate prize. The moments of waiting were excruciating. It was almost a relief when he finally pushed his solid shaft into her.

I had seen passion in Steph when she made love with Don before, but this was at a new level. She gripped his back, urging him deeper and deeper; begging him to give her a baby. It was painfully beautiful. I was witnessing something I would never get to actually experience.

They didn’t do their usual variety of positions. Don just kept her pinned down under him, her spread legs bouncing rhythmically as he thrust deep. His big balls slapped against her ass again and again.
I couldn’t distinguish Steph’s moans and screams. She seemed in a constant state of orgasm.

I had been brave and quiet the entire time, but when Don’s thrusts started slowing, my psyche cracked. I cried and cried as he emptied his balls into my wife.
It was over. There was no going back.

—-

It must have felt amazing for Don as he relaxed beside my wife, her head nestled into his barrel chest. He had utterly conquered our marriage. I had been soundly and irreversibly defeated.

I knelt between Steph’s legs, looking with teary eyes at the sticky cum dripping from my wife’s unprotected pussy. Don’s cock was still draped over her upper thigh, and his hand rested firmly above her hip. It was a clear picture of ownership as I crawled to lick the drops of cum oozing onto the sheets.

He made sure his cock was just inches from my face as I took my first lick.

“Don’t suck up too much of it, slut” he said, obviously savoring my moment of complete defeat at his hands.

I licked up what I could from the sheets first. I had gotten used to the taste of cum by now, but I still found it unpleasant. Steph stroked my hair a little as I moved up to her stretched sex, trying to lick up what I could without burying my face too deeply into her.

Don’s load was enormous, and it kept slowly oozing out as they tenderly made out. I tried to be a good maid, suppressing my raging jealousy and focusing on licking the man goo that kept coming out of my fertile wife.

I imagined all of Don’s sperm swimming inside my wife. I felt my own little balls flop between my thighs uselessly as I continued gently worshipping my wife’s used body.

I knew round two was coming. It always did with Don. I saw his rod start to stiffen again, and I knew it was time for me to get out of the way.

As Don grabbed Steph and flipped her onto all fours, I scurried off the bed and into my submissive kneeling position on the floor.

He smacked her ass as he got ready to mount her from behind like an animal.

Don was going to be sure and breed my wife properly.

Book Five

Sissy Sisters (part 1)

The last thing I was expecting was for the doorbell to ring. It had been a long night, trying not to focus on the mental image of Don’s sperm swimming inside my fertile wife. I was feeling foggy and disoriented as I worked at cleaning up the table from breakfast.

Steph gave my thigh a slap. “Go answer the door, Crissy. What do we keep you around for? Jump to it, maid.”

I hated answering the door. The awkward silence the first time someone saw me in my makeup, stockings, and maid dress was always the worst.

This time was one of the worst ever.

Steph’s best friend Carrie looked me up and down, obviously trying not to laugh as I fidgeted awkwardly and asked her to come in. Her husband John was right behind her. I couldn’t even look at him. If only there was some way I could become invisible.

Carrie and Steph had always looked to me like they could have been sisters. One of my hottest fantasies was having a threesome with the two of them. I imagined their matching blonde hair bouncing as they shared my cock. Before Don came into our lives and locked up my clit, I had masturbated to that image countless times, wishing desperately that it could someday come true.

It was almost painfully hot watching the two of them greet and hug, their breasts touching briefly. I looked over at John. Surprisingly, he wasn’t chuckling at my situation at all. In fact, he seemed kind of nervous and scared. He stood timidly by the door, his slender frame looking almost as if he was trembling slightly. I didn’t make eye contact.

I was shocked as Don addressed him. “Hi John, it’s nice to finally meet you. Steph has told me so much about you and Carrie.”

With that, Don took Carrie’s hand and pulled her onto his lap. Carrie giggled, winking at my wife as her ass landed on his lap. I looked at John, who’s face was now turning bright red. I felt so sorry for him. I should have seen this coming. Of course Steph would try to convince Carrie to let Don take over their marriage as well.

Don wrapped his big arm firmly around Carrie. “Okay, first off, you are never to go by John again. From now on you are Prissy, got it?”

Prissy nodded her head.

“Good girl” Don smiled. “Now take off those boy clothes. You don’t get to wear those any more. And let’s see if you’ve been a good obedient little sissy.”

She had. I was impressed with how smoothly shaven Prissy was, and her clit was already neatly caged; a small silver padlock glimmering in the light from the window. Don repeated the same process with Carrie’s husband that I had gotten; a few minutes later there were some additional keys on Don’s keychain and a whipped pussyboy kneeling on the floor. I wondered if my fellow sissy knew how long it would be before she would get to feel anything on her clit again.

—–

Steph and Carrie had obviously been talking about having babies for a long time. As Prissy and I knelt beside each other, our wives talked in excited tones about what pregnancy was going to be like. Don smiled smugly as they talked, enjoying the company of his bitches as their defeated husbands knelt nearby like the little pussies we were.

And then my ultimate fantasy became Don’s reality.
Steph and Carrie escorted him to the bedroom, starting to strip down as they walked. Prissy and I crawled behind, not daring to get too close to the action.

I wondered if Prissy was filled with the same horrible jealousy and envy I was feeling as they knelt together over Don on the bed. They were down to just their panties as they worked together to pull off his jeans. I thought I would scream in heart-wrenching jealousy as they took turns wrapping their lips around his big cock and nibbling on his balls.

Sissy Sisters (part 2)

There was quite the puddle developing on the floor under Prissy’s locked clitty. I could see that her poor little shaft was squeezing hard against it’s tight little cage as she watched the show our wives were putting on.

I would have given my left testicle to have been Don at that moment. As Carrie was gently easing herself onto Don’s big cock, my wife was caressing her hair and nibbling her ear as her friend had her first experience with a real man.

I had grown accustomed to the angst that accompanied seeing my wife making passionate love with another man, but Prissy wasn’t taking it so well. I saw little tears forming in the corners of his eyes as Carrie took the full length of Don’s big shaft, moaning and obviously in ecstasy. I shuffled closer to my fellow sissy, trying to show my support for what she was going through.

When Carrie started rocking her hips and begging Don to give her a baby, Prissy lost it. With a red, teary face, she jumped up, trying to interrupt the passionate lovemaking.

It was the cardinal sissy sin.

As she got up to the bed, blabbering incoherently, Don grabbed her arm and gave it a vicious twist. In an instant, the unfortunate sissy was turned around, her arm held mercilessly by the stronger man’s grip.
Carrie looked angrily at her husband as she pulled off her new-found lover temporarily.

Don held Prissy in place with one hand and started whacking her bare ass with the other. The sound was horrific. Prissy cried and sobbed, trying unsuccessfully to turn herself around.

Don paused. “Ready to behave?” he asked gruffly.

Prissy just cried, having given up trying to escape his grip.

Don gave another sharp smack to her now reddened ass. “Speak up, cunt!”

Prissy sobbed in a defeated tone I was all too familiar with. “Yes Sir, I will behave.”

And with that Don shoved the poor wuss back onto the floor. She sniffled and knelt again beside me, sore and utterly broken. I knew there would be further consequences later.
Both of our wives were rubbing themselves. There was something primal and deeply erotic about watching a strong man crush a weak beta like that.

—–

A few hours later, Prissy and I found ourselves out in the living room, kneeling at Master Don’s feet as he enjoyed the afterglow of breeding our wives. Steph and Carrie sat on either side of him on the couch, caressing him and looking at each other occasionally like silly schoolgirls with a new toy to share.

Don spoke to us in a firm tone. “Prissy, the way you behaved in there was completely unacceptable.”

I glanced at my sister. She seemed genuinely contrite.

Don went on. “Crissy, you were a good girl, but you should have stopped your silly sister from trying to interrupt my lovemaking.”

“Yes Sir” I said softly.

“Until further notice, neither of you is allowed to speak a single word. Your sissy lips are to stay shut, so we won’t be interrupted by the stupid things you have to say. Nobody wants to hear the nonsense you little cunts are thinking anyway.”

I knew better than to protest. I wanted to ask how long it would be before I would be allowed to talk, but that also seemed foolish. I just nodded dumbly, my knees getting sore.

“Good girls.” Don leaned back on the couch, putting his hands behind his head. “Now worship my feet, faggots.”

Prissy and I glanced at each other before obediently bending down and each starting to kiss the strong man’s feet.
Our wives giggled.

Sissy Sisters (part 3)

I could tell Don was thinking about how he should properly punish me and my sissy sister for her rude behaviour and my failure to stop her. I glanced up occasionally from my dutiful work with my face obediently at his left foot. He was looking at us…that evil smile on his face.

Steph and Carrie would have been enough to intoxicate any straight man. They rested on either side of him, their legs partially over him as they nibbled playfully at him and fought for his attention. I had a view of Carrie’s thighs that was driving me insane. I tried not to think about the fact that I would never in my life get to experience a night like Don was having. The best I could hope for was 90 seconds of masturbation a few times a year.

Don shoved us away with his feet. “Okay little losers. I’m ready for a show.”

I looked over at Prissy. I could tell she was still struggling with the fact she had just spent time worshipping another man’s feet. I felt bad for her.

“I think my little pansies need to get to know each other a little better, don’t you ladies?” Our wives giggled at Don.

“What do you have in mind?” Carrie asked.

Don put his hand firmly on her naked ass as he spoke. “Well, it’s just their first date. What do you say they start with a little kissing?”

Carrie and Steph cheered, enjoying themselves far too much. I didn’t look at Prissy. I couldn’t.

Don leaned forward a little. “Okay little faggots. Here’s how it’s going to work. Whichever one of you puts on a better show gets to cum later tonight. The other one stays locked up for three months.”

I trembled. I couldn’t take another three months. Don was such a clever bastard.

He chuckled, seeing the internal struggle written across my face. “Okay, get to it. I want you to make out like it’s prom night until I tell you to stop.”

We knelt awkwardly, frozen briefly by our horrible predicament. We had been friends for years…watching football, drinking beer, talking about the cheerleaders. The thought of having to kiss him was repugnant.

Our wives started clapping in rhythm, egging us on. I thought about the possibility of being allowed to cum and edged a little closer. Prissy did the same, a horrified look on her face.

Steph and Carrie cheered as our lips touched. I tasted Prissy’s lipstick. It wasn’t cherry.

“Who wants to cum?” Don asked, leaning back, his arms around our wives.
I closed my eyes and parted my lips, giving my buddy a full kiss. I felt his tongue reach out and touch the edge of my mouth. The competition had begun.

We thoroughly humiliated ourselves, our clits dripping through their cages, desperate for the chance of release. Our tongues explored each other’s mouths, our lips locked as we made out. In a move she hoped to score points with, Prissy reached and stroked the back of my head with her fingers as we kissed. I knew I had to one-up her. I let my hand lower to her side and slowly reached around to her ass, pulling her in like a good slut.

Our bodies touched, and we writhed together as we made out like high school whores. I gripped Prissy’s ass as I pushed my tongue deep into her mouth, feeling her soft lips pushing against mine aggressively. I started rubbing my locked clit against her, wishing I could feel something other than the frustrating pinch of the cage.

The sound of Don telling us to take a break was accompanied by happy cheering and applause from our wives. They had enjoyed the show. I looked at the floor, unable to believe what I had just done. What Don had made us do was so much worse than a whipping could have ever been.

Sissy Sisters (part 4)

The night didn’t end well for Prissy; somewhat fittingly for what was assuredly the worst day of her life.
All three members of our sissy makeout show audience agreed that I was the more convincing slut. In her defence, I had many hours of practice being a stupid slut; creating a sizeable advantage.

I felt so bad for her as she knelt below me, looking up at me in disbelief. My sissy clit was having an amazing few minutes of complete freedom. It almost made up for the awfulness of preceding events.
Almost.

The girls watched in fascination as I grabbed both sides of Prissy’s head, pulling her mouth onto my rock-hard baby dicklet. At least her first blowjob wasn’t with Don’s monster like mine had been, I thought to myself as I felt the soft warmth of her tongue on the bottom of my shaft.
It felt completely amazing, even if it was my former football buddy. I did feel a deep sense of shame as I started fucking her face, but not nearly enough to stop me from humping her like a madman.

She didn’t have to wait long to experience her first load of fresh warm cum.
My little balls had been waiting months for this. It felt completely amazing as I gripped her head tight and exploded in her mouth. Spurt after spurt of my sissy cum shot into her throat. The sounds of gurgling and choking didn’t stop me from humping, wishing the feeling could last longer.

When I finally looked down, Prissy was literally sobbing. The shame of sucking a cock, of doing it in front of her wife, and with her best friend…it was more than she could take. I felt terrible.
I knelt immediately, looking at her as if I could somehow apologize with my eyes. Part of me was glad we still weren’t allowed to speak.

She had been a good slut; swallowing all of my cum. I remembered the taste of the first load I had taken from Tom, and the sickening feeling of the hot goo sliding down my throat. It wasn’t easy for me, and I was sure it hadn’t been easy for Prissy.

It wasn’t fun locking myself back up, but I did so without saying a word. Don just smiled, thoroughly enjoying his ownership. Prissy looked so dejected. The reality of three full months in chastity was fully settling in.

Don told us to kneel beside each other at his feet, and we awkwardly slid together before him.
He looked at Prissy, who withered like any weak beta would under the stronger man’s glare. “You’ll be spending the next three months in chastity, Prissy.” He said it matter of factly. The poor sissy was still crying a little. “And that’s if you’re good. Remember, any of the three of us can add days, weeks or months if we feel like it. Keep that on your sissy brain when you’re doing our housework.”

He looked over at me. “And this goes for both of you…you will not speak a single word for the next week except at your offices, and even then as little as possible. The moment you get home, your lips stay sealed.”

And with that we were brushed off to go to bed as the man of the house enjoyed the company of our wives.

End

Chrissy E

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