tagTranssexuals & CrossdressersHis Sissy Bitch Ch. 06

His Sissy Bitch Ch. 06


I think about it all the way home, makes me so hot I want to masturbate right there in the back seat of the cab. I can feel the wet spot on the end of my little thing, feel it against my inner thighs, feel my small baby like penis slide around tucked up under my butt, pushed down and held between my legs as we ride toward my house. I try to keep my penis tucked, hold it tight as I can, hold my legs together as close as possible so as to not let it stick out in front, can feel myself start to get hard just thinking about him. I can't wait to get home and masturbate. The driver keeps checking me out in his rear view mirror, sees me squirm on the back seat.

I am so hot for this man, hope that he calls, hope he wants to see me tonight. I'm so hot thinking about what I do to be his number one little girl, the dirtiest little whore he has. And I love being that for him, he knows it. The man that took me away from my former boss, my ex boyfriend, the man that made me the full-time whore I am for him today. He knows I'll do the dirtiest things, he knows he can count on me please his 'special clients'. I do it for him, no questions asked. I'm lost in thoughts of him, him on top of me.

The cab ride seems like it goes on forever. All I can think about are his hands all over me, his hands that reward the things I do for him. I want to get home and prepare myself for him, I am super hot thinking about what he demands. And his personal demands are much simpler than things I do to please his clients. For him it's white 3" heels, open toe with ankle straps, lubricated and very slippery little hole, baby smooth all over with a pink frilly bow on my soft penis. That, and a lot of pink lip gloss and dark eye makeup. That's all. No hose, no corsets, just shoes and naked with a pink bow. Very erotic and so simple, my man wants nothing else, he says it highlights what I truly am, a sissy. And he says he likes instant and complete access to me.

I remember the first time I saw him at my house, first time I saw him after he left welts on my rear end in the office of his restaurant. He came to my house two days after that. After I sucked his cock in his office, remember that too. Called me the night before his first visit to my house and told me not to go to work, said "Be home and naked and in white heels." He just said that and hung up. I called my boss, had to call in to take the day off, wanted to tell him what told was asked of me. After all, it was him that 'gave' me to this man. I felt strange having his secretary take my call, tell me I no longer worked there. I couldn't believe it, I was fired, fired by the man that had been my lover for the past year and a half. I tried to call back but she would not take my call. I was in a daze when the doorbell rung. I had not even started to dress for what I thought was to be my first date with this man, went to the door in just a robe, still thinking about not having a job, about being 'fired' without an excuse.

"I told you naked and in white heels." It was him...him and two other men with him. I was shocked. They couldn't have been older than twenty-one, there was the man that used me in his restaurant two nights ago. Him with two college boys, stepping into my house, pushing passed me at the door, I was truly shocked.

I felt dizzy, embarassed, standing in my hallway, felt myself let the robe fall off of my shoulders and then to the floor as his hand reached to my shoulder and pulled it down over my back. He almost ripped it off of me. My face turned bright red, stared at the two men that looked back at me. My front door still wide open for anyone passing by to see it all, felt him take my arm and lead me into my living room, he pulled me like a dog on a leash, his eyes moving around, looking over my house for the first time. I wobbled as he pulled me to center of the room, pushing my hand away as if he were through with me. The three of them sat. I stood naked in the center of the room, looked down at the floor.

"I like it." The first man that spoke stood. He stood. He walked to my side. I felt his hand run all over my rear end. Was being felt, inspected by a complete stranger, my face was bright red. I knew not to speak. I felt my nakedness, felt that completely vulnerable feeling I love and hate at the same time. And I felt him leer at me, felt him move up to the side of my face, felt his menacing smile, like a spoiled college boy. Felt him reach down with his other hand and flick my little penis. It hurt, stung, I yelped and jumped back. He laughed. He reached for it, grabbed it and pulled me back forward, held it so tight it hurt. He hand looked huge on me.

"I told you it was small, like a baby. And this bitch has a mouth you won't believe." My man sat and watched, turned to the other seated young man as he said that, smiled back at me.

That's how it happened. That was the first time I saw the man I am now addicted to, the man I will do anything for, first time I saw him in my house, first time I truly realized what I was, what he would make me into.

The man standing next to me said, "We'll see about that mouth later. I want to fuck this bitch first." That's when I felt him release my penis and take my wrist. He twisted it and pulled down hard.

It happened so fast. It was like a dream. Felt the man next to me put his other hand on my back, run it down to my rear, felt him pat my butt gently as he pulled me to the floor, heard him say, "Get on the floor, face down on your knees, butt up and out, let's go. Show me that ass."

He slapped my right cheek so hard he almost knocked me over as I was half way down to the floor. He told me to reach back and spread my cheeks. Not asked, ordered, "Push that ass up, bitch! Spread it, show me that hole, now!" I did it, just did it, could not do anything else.

Face down to the floor, knees up under me, back arched with my butt up high, I reached back with both hands and spread my cheeks so wide it hurt. The two seated men watched as the man behind me quickly took down his pants and knelt behind me. Naked on my living room floor, three men in my house, two watching as I was being fucked. I was in shock. They watched as he fucked me fast and deliberate, watched as I whimpered and struggled to hold my cheeks apart for him.

He was the first.

They two younger men took turns. One after the other, they used me. And as soon as one man finished the next took his place behind me. My boyfriend sat and watched, just watched passively. I remember looking up at my new boyfriend, seeing him look down at me, just staring back coldly as he watched his two young studs 'break me' as he put it later. Still had the five sharp red welts on my rear from his riding crop and my visit to his restaurant two nights ago. I could feel the still stinging red stripes on my baby soft cheeks as the young men slapped up against me from behind. The look on his face, he was enjoying this, and he was clearly in control. I saw that this was pure business to him, saw that for the first time, saw his 'business look'. I was being taught. He was teaching me, showing me what I was going to become for him.

When the first man fucking came in me, the second stood and took his pants down, stepped out of them taking them off over his shoes, just took his pants off and went to the side of me. He knelt and took my head, pushed his semi erect cock into my mouth so hard I choked. He was large enough to push it into my throat, even semi erect. I felt him grow hard instantly. I couldn't help myself, started choking, I had tears in my eyes, he held my head in place kept using me to get rock hard.

When the man behind me came he pulled out of my rear fast. Pulled out so fast it hurt, I heard myself yelp as I felt the other man's cock yanked out of my mouth. And then he moved to my rear, changing positions with the man behind me. And so it went. The two of them switching position, taking turns using my mouth and rear end, they said nothing. There was complete silence in the room except for the sound of them moving in and out of my rear, that and my whimpering chocked sounds as they used my mouth to made themselves hard again. My man sat and watched, said nothing, just sat smiling down at me.

10am, Monday morning, fucked five times on my living room floor, mouth used until it was numb. Cum and the taste of my rear all over my face, tears down my cheeks, I was a mess. And I was to find out later that I would do this very 'act' with these same two men for a couple of my new boyfriend's 'very special' clients. How far I'd come in just over a year of being secret sissy slut for my now ex-boss.

When they finished with me, the last young man moved to the side of me, wiped his cock clean on the side of my cheek and hair. Then he did something I hated. He took my jaw with his thumb and index finger, squeezed my face so tight it hurt, made my lips stick straight out. He took his cock in his other hand and just rubbed the end of it all around my extended lips. Looked down at me and laughed, rubbed it back and forth across my lips. "Good boy."

He did that before pushing my face away roughly. Then he stood. They both stood over me, looking down at me as they put their pants back on. My boyfriend finally spoke, heard him say, "Good job." I saw him take out a roll of money, gave them each something as he stood and walked them to my door.

As the door closed and he came back into my living room I heard myself say "Do they work for you too?" My eyes were closed, my face to the floor still, afraid to look up. I was shaking, crying softly. My rear was numb, have never felt so used, so sore. I was covered in cum, rear open wide, dripping cum running out of my little hole and down my leg into a puddle on the floor. I looked back between my legs, opened my eyes, saw it all over my carpet between my knees. I was frozen in that position.

One man came in me twice, the other three times.

"Yes. They do." I looked up at him, he was next to me. "Think of them as summer help." He laughed, felt him reach down and pat my head, ran his fingers down the curve of my back. Gave me chills when he did that, "I want you to go upstairs, want you to clean up, get that little ass sweet and clean and cute. Clean up real good for me. I want you in pretty white heels, that's all. I told you that on the phone, I'm disappointed you weren't dressed for me when I arrived." He slapped my ass. "Let's see how fast you can make yourself presentable. Go ahead, baby." He watched as I stood. I said nothing.

"You did real good today, made Daddy real happy." He sat on the couch. "Your former employer was right, so was the one that just ran his dick around your mouth, you are a good boy."

I hurried upstairs as he said that, felt his eyes on me, felt him watch my very wet and sore rear end walk up the stairs. I felt my cheeks slip and slide against each other as I moved. Felt the abuse done to my tight little hole, felt it burn, felt it stretched wider than it had ever been stretched before.

When I came down stairs he was waiting for me, smiling. He was pleased. Shiny white high heel shoes, I was a submissive little sissy in girly shoes and in way too much pink lip gloss. And something special I thought he'd like, I put a pink ribbon tied in a bow on my penis, made it stand out showing off how small it is. Did it the way I did it for my ex boyfriend, knew he'd like that. Showed him that for the first time, it's now one of his favorite looks for my little thing. I also had on deep black eye makeup. I was out of shock, back into total whore mode. I liked what I was becoming, liked it a lot. I was dressed the right way.

He liked what he saw, saw him sit forward on the couch as I walked toward him. "The ribbon, yes! I love it, from now you keep that, want that on that thing always when I come to see you. I like it."

I went to him, sat on his lap, felt him pull me down onto his lap by my arm. I could feel his huge erection through his pants. "I like the way you look, and I like you open and ready. You can do that girl feminine dress thing for the boys. For me, you're a sissy. Naked and slippery, do you understand?"

"Oh yes, Daddy." I rubbed my rear against his hard on., wiggled on his lap. I put my arm around his neck.

That's when I felt him push me off of his lap and onto my back on the couch. "And with the ribbon, perfect!" I felt his hand cup my balls and penis.

He just took me. He took me on the couch, just fucked me. Never like that before, ever, it was never like that with my ex boyfriend. This man felt special. That's when I felt him fuck me for the first time, felt like the first time any man had fucked me, ever.

He kissed me too, petted me, made me crazy for him, made me feel like I wanted to be no place but underneath him as he lay on top of me on the couch. All I wanted was to wrap myself around this real man, be his. I wanted to be owned by him.

Pressed up against him as he started to get completely naked, felt him slip out of his clothes and push them to the floor, felt him hurry to take down his underwear, kick them off, felt his huge erect thick and real-man cock in my hand as I guided him to my hole. Raised my rear up for him, I offered myself to him as he kissed me hard. Felt him on top of me, his tongue down my throat, felt his huge erection move up and into my rear end, felt my legs wrapped around his back, his strong, large hands all over my rear, up over my nipples, felt myself being held down tight underneath him as he started to fuck, really fuck me. Even though I'd just been used he felt huge in my rear. I loved that.

After he came in me he stayed on top of me, told all the things I wanted to hear, petted my face, semi erect cock still in me, squeezed it tight with my rear end. Told me I was his 'special girl' now, had big plans for me, kissed my ear, played with my hair, drove me crazy, crazy, crazy. He French kissed me until he made himself hard again. The he did it again. Fucked me so long and so slow, long full strokes that seemed to go on forever. I was his to do with as he pleased.

When he came the second time he pulled out and did it in my hand. Whispered in my ear, "Take me in your hand, baby. I want to cum in your hand." He drove me crazy when he said that. Felt so good to stroke his beautiful cock as he slid in and out of my hand and came all over my stomach.

When I glanced over at the clock, dizzy, hazy, hypnotized, I noticed it was 2pm, he'd been on top of me close to two hours. He laughed again, saw me looking at the clock, looked down at me, his cum all over my stomach and running down my between my legs and over the side of my stomach onto the couch, heard him say, "My special little girl."

I just laid there as he got up and got dressed, watched him put his clothes on. Used my robe to wipe himself clean, didn't use my mouth like my ex used to. I liked that too.

I was gone, lost. Felt drunk as he walked to the couch. Felt him reach down and take my penis in his hand. I was hard, as hard as I could be. He smiled. "Cute little thing, small even when you're excited. So cute, baby, shame I don't have time to make you cum. I'll reward my little sissy next time. I have to go. But I'll give my special girl a little tease."

I started to breathe deep as he ran my penis in and out of his hand, tiny little ring made with his thumb and first finger, he knew how to drive me completely crazy, wanted to cum for him so bad. He watched as he teased the head of it, wet spot all over his fingers. I saw that business look come back over his face.

That's when he told me I was to never wear male clothing again. I was to start moving toward complete fem dress and behavior, was to never be seen as anything other than the sissy girl I am now. Just said it straight out as he manipulated my little thing like it had never been done before. Told me to get rid of every piece of male clothing I had. I told him I would, told him I would do anything for him. He watched as he addicted me completely to his hand, watched me breathe deep and writhe on the couch before him. I was naked in front of him, his cum dripping out of me onto the couch, felt it warm and slippery under my rear as I ground my hips, tried to push back against his hand.

His phone rang. He stared at me and then saw him take out his cell phone with his other hand as it rang, he checked the number of whomever was on the other end of the call. That's when I saw him slip away, saw his business look come fully back. He took his hand off of me, wiped his fingers on my leg.

I know that business look now. Know it well. He ignored me as I whimpered as he let my penis go. He moved to the door.

"I'll call you later. I have to go. Don't worry about not having a job. You have a job, a full time job. You work for me know. It's going to be better than before." He said that as he was on his way out the door, closed the door behind him.

When he said that I felt my jaw drop, I was shocked back to reality, could not speak, just watched as he walked out of my house. It was like a dream, all of it. Felt his cum on me, saw the puddle of cum on my living room floor where I had been put into position, put on display and used by his 'employees'. Felt my tiny hole start to throb, felt painful and sore as reality started to set in.

I rose. Went upstairs and started gathering my male clothing, started putting them in a pile to discarded, thought about how much he'd be pleased that I did that so fast. I struggled to not touch myself while I did, had a constant little sissy erection as I cleaned out all my closets and drawers hints of my male past.

That was the first time with him, first time actually being fucked by him. That was when I became truly obsessively addicted to him. Fell in love, so to speak. That was the first time.


I'm wearing one of several of my 'professional woman' business suits. Dark blue dress, crisp white blouse under it, very expensive black hose, I look like any female executive on her way to a business meeting. I wear a wide brim sexy yet professional looking hat and wide fishnet vale over my perfectly made up face, just covers the eyes, looks like a mourning vale but kinky, very hot! The only thing that takes away from my professional business-woman-meets-mourner persona would be the shoes. The Ferragamo 4" spike heel shoes not only scream 'fuck me' they make me quite tall. But it doesn't matter, it's what they want me to wear on my visits to see the old man. They insist that when I visit their penthouse the doorman and all in the building must see me as a professional woman, not a slut. Any deviance from the 'look' and I get reported. I can still hear his nurse. She scolded me on my first visit to see the old man, told me she knew what my boyfriend "does to disobedient whores". I can still hear her say that, made me cringe, and that she'd have "no problem turning me in" if I broke even one of her rules. I don't break any rules. I've been the perfect gift for the old man. And that's just what I am to him, 'a gift'.

As we ride along I think about today's visit. I see the old man twice a month. His nurse says she's concerned about his heart and that I get him very excited. That makes me smile when I think about it. She's the one that arranged my visits. I like doing my part to give him pleasure. His heart is just fine. And I know my little ass makes him happy. I like that too.

Don't know his age but he's got to be in his mid to late '80s. He's confined to bed but that doesn't stop him from enjoying me. He even gets to touch me when she allows him to do that. I actually like that, makes him feel good.

When I arrive at their door his doorman walks me to the elevator, takes me right up to the penthouse. She's always there as soon as I arrive. She scares me and she knows that too. She plainly likes that part. She's never friendly and I avoid conversation with her, just arrive, do as the old man likes, leave and avoid her icey stare as fast as possible.

Report Story

bykeptsissy© 6 comments/ 104473 views/ 37 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: