tagTransgender & CrossdressersA Very Hard Working Girl

A Very Hard Working Girl


I jump around a lot when I tell my story. I don't always tell it in the order that it happened. But I do tell my story accurately. It's all me. I write from experience, love to share the dirty little kinky things I do. There is no moral to the story, no ending. I just like to write about the things I've done and continue to do. And I love to think back and remember the beginning of my slutty little life and sexual adventures.

The one thing that I never tire of is servicing a man, a real man. I love men! I love strong, dominant and very masculine men. I like to be handled firmly, sometimes roughly, like to be with a man that is in complete control. And I have one like that. He keeps me in the kinky style I've become accustomed to, pretty much owns me. I wouldn't have it any other way. I serve whomever he sends to me to. I'm such a slutty little 'girl'--the more, the better.

He is the most in-control man I've ever met. I'm his little princess and I make sure all the men he sends my way know that too. When I think back about meeting the wonderfully dominant man I belong to, when I think back about being guided to a life of sexual submission and sexual addiction, that alone gets me very hot. I feel my tiny little sissy penis stir in my panties just saying that. I can hardly keep it tucked up submissively between my legs, can hardly write about it without masturbating.

I remember how I met him and started never saying 'no' to him or the other men he gave me to. At first I was very apprehensive, didn't like strange men showing up, some of which were not that attractive to me. I got used to it quickly. And even came to like the excitement of it all, the initial meeting, feeling their eyes all over me as they'd come in my door. These were the men my boyfriend insisted I entertain, insisted I see. They were my clients. I had very little choice in the matter. I was his and did what he told me to do. And once he made me realize what I truly am I did it all willingly. Of course I could walk away from it all. But why would I? Like I said, I'm a submissive little slut and love it!

I dress the same way for almost all of my in-house clients. White 3" spike heel pumps, white lace top ruffled girly ankle sox, sometimes thigh-high lace top stockings, that is all I wear. I've described it as my 'work clothes' to other working sissy girls like me.

And I give the boys something else special to see--a pink ribbon tied up tight around and under my very small balls. Which pushes my tiny soft penis straight out in front with the pink bow on top of it all. The ribbon truly shows off my sissy little thing, shows my true nature.

I'm always baby-soft and smooth top to bottom, even when not entertaining a client. And I always wear much too much eye-makeup to enhance my sissy look. I usually wear my hair up which shows off my large hoop white plastic little-girl earrings, soft neck and shoulders. I am the perfect sissy bitch, the perfect piece of candy. That is the point of my sexy little outfit.

My rear is always lubricated and slippery too but it never shows when I walk or sit, it's never messy, can sit bare butt on a white couch or a man's lap and not leave a stain. I lubricate just enough to make my rear easily available. No man ever had a hard time instantly using my tight little hole in any way he desired.

I like it this way too, the way I dress for my visitors. I don't have to do a lot of elaborate feminine preparation like I do for my boyfriend when he takes me out. Just have to be cute, accessible and ready to be a slut for an hour or two. I do dress for some men in different outfits, some men have very special needs and I cater to that too. But the majority of the men I see want my mouth or my rear end, my little sissy outfit is all that is required to set that off nicely.

The list grew from one or two regular visitors a month at the beginning of my 'career' to five regular men a week. Sometimes more, sometimes I see several men a day. I am very much in demand. It's because I'm one of the cute ones, as they say. That and I have a very dirty mind. The boys like that. My boyfriend groomed me for that too.

And I have a very young look, a plus for what I do. I work hard at that. Men say I look like a teenage girl. My boyfriend taught me to walk just like a girl, tease with my eyes, taught me to be on exhibit for any man that might be interested. I don't take hormones, don't have to. I have a very small frame. I'm little girl-like, keep my rear end in shape and have legs to die for.

The men my boyfriend sends my way are carefully screened by him. They're business and professional men that want the perfect discreet dirty little secret on the side. They want a sissy gay boy secret that can pass as a girl. Men that are bored with their wives and don't want the entanglement of an affair, want a whore to use, a gay whore that doesn't expose them to gay bars in search of twisted sex fantasy, these are the men I entertain. And I do that to for them, make all their twisted sexual fantasy real and come to life. They also want a safe plaything that they are in control of in a safe environment. And I am all that too.

A few of my visitors visit more than once a day. In general men are done, through with me, as soon as they cum. But they soon want to cum again once their dirty mind starts back to work. And that usually doesn't take very long. I'll see a man in the morning and he'll stop by again sometimes at lunch. He'll fuck me in the morning and then show up for drive-by sex at my door on his lunch break. I have one fucks me for an hour every Tuesday morning and them comes back at noon, just walks in the door, takes it out and masturbates, cum all over me while I kneel at the door. He doesn't even take his pants off for his 'lunch' with me.

They know I'm ready to please, whatever it is they want they know I'll do it. My boyfriend guarantees that. It's part of the service he provides to them. And once they are signed on and scheduled they have my phone number. All they have to do is call. I never said 'no'.

The main thing they like about me is my mouth. I can make a man cum almost instantly with my mouth, one of my many tricks. But only if he wants that, I can tease a man for an hour or more before making him finish. The men that take me to bed have to use a condom, my boyfriend demands that. He is the only man that uses me without a condom.

By the time I started doing this 'service' for my man, seeing his friends and associates, I was so much his total bitch, so sexually addicted to him, that I would have let them use me without a condom if he ordered it. I still would. Nothing makes me hotter than being this man's whore! He knows this and he's the restraining factor in all this. If it were up to me there are several that I see that I'd let cum in me like he does.

I never ask about money. I know it's heavily involved. I am happy to be able to be the sex addicted little bitch he made me realize I am. I love every aspect of my life, it's not about money. I have a great condo he provides me with (sound proof!) for just this type of 'business' activity. I still have my original house too, a Corvette he gave me, closets full of the most high-end feminine clothing a real woman or cross-dressing sissy like me could ever hope for. I am the perfect kept mistress!

And if I ever need money other than the very generous allowance he gives me once a week all I have to do is ask for it.

Aside from the usual sexual favors in my living room or bedroom, I also have a playroom, a very special little playroom. Some of the men that visit have 'special needs'. Some men like not only to fuck a little bitch like me but like to do it while I'm restrained by my wrists to a hook in the ceiling or restrained ankles and wrists over a spanking horse. I do that for them.

Two of my clients like to spank. One, very much older man, likes to watch while his friend spanks me hard. They always visit together. The older man masturbates while watching me get paddled by his young boyfriend with a short leather strap. He gets off on hearing me whimper and cry out, directs the 'action' while seated in a chair, masturbating slowly. The much younger man of the two sometimes puts himself into my mouth until I calm down, then starts again. These sessions never go less than an hour. It hurts and I do hate it while it's actually happening. But I also do masturbate thinking about it all after they leave. Looking at my bright red butt in the mirror gets me very hot, makes me think about wanting to do it again! These two men never use me in any other way. I am their S&M sissy doll.

I see another man that spanks too. I wear a tight panty-girdle for that 'job'. He insists on that, my little thing tucked up between my legs. And I soon found out why he wants me in a panty girdle. It hurts more, much more. Don't wear anything else, just naked in a black panty-girdle and black heels. I always have to kneel for him and ask to be spanked. Makes me beg him, I have to hand him the paddle, my eyes to the floor. He does it across his lap. Hurts much less than the other two men that restrain me across the whipping horse! And I always go down on him after he spanks. He cums very fast, that's the easy part.

Luckily I see these clients every other week, sometimes less, always have a hard time sitting after those sessions. I always schedule them later in the evening after my other clients have gone for the day.

I've never felt in danger, always know that the men my boyfriend sends my way can be trusted. These men have much to lose. They're mostly doctors, judges and lawyers. I even see one politician (he's the one that likes me in a panty girdle across his lap, if the voters only knew!)

I feel very safe doing what I do. Although I perform specialty services, for the most part I suck them. They love my mouth, rave about my talents on my knees. And I love doing that for a man most. It's my favorite thing, to take a man into in my mouth and drive him crazy. Some girls think it's easy to please a man this way. Just put it in your mouth, he does the rest, that's what many think. There's more to it than that. When I go down on a man I do it like he owns me. I make him feel like I am completely his. And I am for that moment.

And I use my tongue on the head of it, and all over the hole both in and out, subtle little tricks to make him moan, cry out, whimper and want me all the more. Nothing drives a man crazier than to lick the hole of his hard cock with the pointy tip of my tongue, over and over again, push it up inside.

And as mentioned, when I want a man to cum, he does. Very quickly. I hold just the head of it pressed tight against the roof of my mouth, lay my tongue flat across the hole and underside of the head, just up to the start of his shaft. I hold it real tight. I pump, actually jack him off with my mouth, while moving my tongue slightly side to side and back and forth across the hole, still holding him in place. Very subtle but very effective, I've never had a problem making a man cum in my mouth in less than three minutes like that. It always works.

And the men I see rarely want more. They are not looking for love or love-making. They're looking for my mouth or tight little rear end, or both.

The biggest turn on for me in all this aside from the sex play (and some of my clients are really very good lovers, and do take me to bed and actually do make love to me, get me very turned on!) is meeting them at the door naked and sissy-like. Fresh and ready to be used, they are always dressed in a suit and tie or some type of casual business attire. I love being naked in front a street-dressed man. Feel so submissive and at their disposal, when I masturbate it's pretty much always thinking about that. I think about the moment they walk in my door and there I am in just heels and stockings, feel my slippery little hole up between my cheeks as I move toward them. Walk to them and press up against them, say 'Hello, Daddy'. That's the turn on moment. I can feel my tiny thing start to get hard as I say that.

And they could care less about my little penis. To them it's just part of my 'look'. My penis really is little and they like that too. Erect I am no more than three inches and soft I look like a very little boy. And only one man out of all the men I see ever wants me erect. His thing is watching me masturbate into his hand and then licking it clean. He then fucks me senseless, teasing about my little thing.

My boyfriend tells me my tiny penis is a plus, brags about that to perspective clients. "You won't even know he's a guy, he's a girl top to bottom, doesn't even have a dick.", I heard him say that over the phone when he was talking to one of my soon-to-be visitors. He laughed as he said it and made me blush. I was going down on him at the time.

This all started almost by accident. I met my boyfriend online. I've been his 'little princess' as he calls me for over three years now. At the time I started chatting with him I was what they call 'straight-and-curious'. I was terrified of actually meeting a man, never confronted my fantasy to so. I was cross-dressing in my home but never in front of anyone or on the street. I'd chat online with men and would 'talk' very dirty with them while masturbating. And then HE came along.

He got me hotter than any man I'd ever chatted with online, would send me long and seductive email too. After so many hot online chats and so many suggestions to meet with this man, I gave in. I did. First he gave me his cell phone number, made me feel like I could trust him completely. He told me to call him anytime. I did that too. He got me so hot I couldn't say no and after many cell phone conversations I let him come to my house.

I was terrified waiting for him the first time, standing in my living room fully feminized and made up as cute as I could do at that time. Seeing his car pull into my driveway I was frozen, felt utter panic. I'd never been with a man before in my life. And now one was at my door and I knew what he expected of me. I looked at myself in the mirror. I felt like throwing up, felt like he'd find me ridiculous. I felt panic as he came in the door.

"I like it. I'm going to stay." He said that as he entered, just stood in the doorway staring at me. And then he closed the door behind him. I felt my heart jump to my throat.

He told me on the phone that if he came to my home and didn't find me attractive he'd just tell me and leave. He was so confident, so dominant right from the start. I felt my face turn bright red as he said that, said that he liked me. I looked to the floor.

"You're really cuter than I thought you'd be, thought you'd be just a guy in a dress. You're much better than that, actually have a girly look about you." He smiled at me.

At that time I didn't have the wardrobe I do now. Was in some things I'd gotten online, Frederick's of Hollywood black bustier with a lace push-up top and I had a long dark wig over one eye. My hair wasn't as long, woman-like, as it is now. I'd done makeup but not even close to the super model look I can do now too. I wore black spike heel ankle boots with thigh-high lace top stockings and lace panties. All black except for my robe, over it all I had a red short silk robe, barely covered my rear end.

He walked to me. Took off his over coat and handed it to me, I took it and hung it in the front closet. I felt his eyes all over me and I felt ridiculous as I walked, had never done anything even close to this. He made that feeling go away almost instantly.

He took my arm and pulled me up close to him when I returned. He's muscular, very firm, 6' 4" and all man. I felt his other hand go to my rear. Felt him cup my cheeks, moved my robe up over my butt. He squeezed my arm so tight it hurt. He held me in place as I was being inspected, felt up.

"I like it very much, like the look you've put together for me too, like the potential I see. And what about you, do you like what you see?"

His mouth was right next to my ear, felt the heat of him up close, whispered that into my ear. He moved my robe down over my shoulders, let it fall to the floor. I felt his hand start to feel my rear end all over, pet me, cup it in his hand. His fingers running up and down the crack of my cheeks on the outside of my panties made my little thing start to stand straight up. I felt the goose bumps rise all over me.

Then I felt his hand go to the front of me, cup my penis and balls through the outside of my panties, felt him exploring, sizing me up more than feeling me up. His fingers ran up and down the outline of my little erection inside my panties, felt his index finger run over the wet spot in front.

"I do, very much." Heard myself stammer, could barely speak, still looking to the floor. I was his and he knew it.

He laughed. "Why don't you get me a drink, vodka I believe you said you have over the phone. On the rocks, Princess."

He squeezed my penis with his thumb and forefinger and then took his hand off me. I heard him call me that for the first time, 'Princess'. I liked it. No, I loved it.

Felt him release my arm and move away from me to my couch, I hurried to the kitchen to get him a drink. I could hear my high heels click on the floor as I moved, still remember that sound, could barely walk, my little thing sticking out erect, a real man sitting on my couch.

I sucked him twice that night, swallowed for him the first time. When I returned with his drink he motioned for me to kneel in front of him, snapped his fingers and pointed to floor, smiling up at me. I didn't have to be told. I handed him his drink and went to my knees. I watched him sip it as I unzipped his pants took his cock out and did what he wanted me to do.

He was gorgeous, huge cock, almost fully erect when I took it out with my hand. His hard on jumped up in front of my face as I looked up at him. Held the base of it as it grew rock hard in my hand, I leaned forward and kissed the end of it. He just stared down at me, watched as I put him in my mouth and did what he wanted.

I remember thinking that it couldn't be any better for my first time. After he came he talked to me like I was a little girl. Told me how cute I was, how much he loved what I did for him. He had my attention, all of it. He kept calling me 'Princess', drove me crazy. Told me that he wanted to see me more than just that one night, he said he wanted to start seeing me regularly.

The second time he was ready to cum he pulled me up close to him, patted my rear end firmly, told me to 'be a good girl again'. I got hard instantly, went back onto my knees in front of him. Sucked him like I wanted him to own me.

He had me take it out of my mouth before he came the second time. He pulled me up onto my feet. He stood and he used his hand to finish into the front of my panties, jacked off into them. Then he took my arm and lead me, had me stand in the middle of the room like that, soaking in front, dripping with his cum as he watched me and talked to me.

I was dizzy, almost hypnotized by this big strong man. He sat and watched as I stood there, obviously his. Then he had me take my panties down to my ankles, told me to let them stay hanging on my boots. He had me turn and show myself to him as he talked. Had me present my rear end, bend slightly and spread myself, he was inspecting me top to bottom, directing me. I remember loving the feeling of his cum all over me in front, dripping off my panties as they hung on my ankles. I still masturbate thinking about that!

Through all of it he never undressed. Just pulled his cock out through his fly when he wanted me to go down on him, he just told me to do it. And when kept calling me 'a good girl'! I was beyond dizzy, wanted him to never leave.

Report Story

bykeptsissy© 5 comments/ 110561 views/ 46 favorites

Share the love

Report a Bug

3 Pages:123

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: