A Very Hard Working Girl

When I started doing this full-time I saw my first gentleman caller at my house. I didn't have the professional play house I have now. He was as nervous as I was but I made him feel comfortable enough to want to come back. He would have come back even if he didn't want to. He's a professional photographer. The man I sucked in the backseat of his car and my boyfriend sent him to me for just that, professional photographs. I still see him. He's one of my regulars. He's one of the very good lovers that likes to take me to bed too. He treats me like a lady. And he's a very good tipper!

The first time he came to my house he had me pose for a lot of pictures. He had me dress in different outfits, some very suggestive, others straight and narrow. Some of the pictures he took made me look like a business woman at a board meeting, straight fitted below the knee skirt and crisp white blouse, with heels. Others had me on the couch on my knees looking back over my shoulder in just panties and heels, panties down below the curve of my rear end to the tops of my thighs. My little penis and balls exposed over the waist band, others with them tucked into my panties. I knew what he was doing. He was putting together my marketing package, my portfolio. At that point I didn't care who knew what I was. I was proud of being a sexy little playgirl. Wanted more, I was a very motivated little bitch. And I wanted everyone to know.

It was shortly after I started seeing that man that I was given a condo, my 'playhouse' as I think of it. And he took many pictures there too. One of the sexiest series of photos he took of me is with me on my hands and knees in front of him while he sat on the edge of the couch. He was naked, his beautiful cock dangling over the edge of the seat cushion. He was semi-erect, and pointing toward the floor. He shot pictures looking down at me as I leaned upward, face almost to the floor, back arched with my butt pushed way out licking the hole of his cock, balancing it on the tip of my tongue. I had my hair up high, string of pearls on, false eyelashes to make my eyes very hot, wore pink lace panties and heels. That was it. The entire series shows me looking me up at the camera with a dirty sexy little look on my face, my soft shoulders, my smooth back and curve of my rear end. The picture series shows my butt in a way that any man that saw it would be crazy not to want me. Also shows my pointy little tongue doing what it does best for a man. This is one of the most erotic displays I've ever done, very proud of that. I didn't always get to see the pictures he took of me, my boyfriend keeps them.

But that series he not only let me see, he had them all framed. They're on the wall of my playhouse living room.

The photographer started sleeping with me after all of our sexy photo sessions, became one of my favorite lovers and still is. When he takes me to bed he treats me, nice like a perfect lady. Not pushy, not demanding other than in good way. He feels me in all the right places, he pets me. He makes love to me, doesn't just fuck me like others do.

I take my time and suck his nipples or French kiss him deeply while he finger fucks me or plays with my little penis. I tease this man and try to please him to no end. And he fucks me better than any man other than my boyfriend. I've never told my boyfriend that but he does, the man makes me never want to stop. He does something that really drives me crazy, uses just the head of his cock. He lets my tight little hole grip it just below the head, close myself around his erection. Then he pumps slow and deliberate short little strokes. The man drives me insane when he does that, has made me almost cum by doing that. Ican feel just the head rub up inside of me, so hot! And he makes beg him to push it in. He always does but not before I'm truly begging. And if I try to push up on him he holds back, just teases and works me like that. I have spent hours with my legs up around his back, his tongue down my throat pleasing him like that.

Most of the men I see care nothing about me being sexually excited. They just want to cum and leave. This man likes to see how far he can take me. And he does just that. And actually touches me. He holds my tiny erection sometimes while he fucks me, sometimes lets me cum into his hand. No other man I see does that, not even my boyfriend. And after he cums he doesn't run off, he stays. Stays and talks with me, watches me fix myself up and make myself pretty for him. He's one of the good ones.

After I started seeing the men I see for my boyfriend, I started doing something else, something just for me. Not for him but for my own pleasure and amusement, for me only. I started going out once or twice a week dressed to kill, dressed to catch maximum stares and attention. I started going out and shamelessly putting myself on display and even flirting from time to time. I always did it safely, went to public places, never went any place I felt compromised. I'd dress hot, dress to see how men and women reacted to me. Maybe wear a short pleated skirt, blouse tied up just over my tight and flat little waist, dirty school girl look. I'd expose my flat stomach, skirt down low at the top. I wear very cute shoes too, always high heels, maybe cotton ankle sox, sometimes ruffled, and black pumps. I would walk through the mall like that, go to cafes. I'd go shopping like that too, loved lingerie shopping dressed like that or in something equally sexy and over the top. I love the looks on the sales women's faces, priceless.

The looks I got ranged from angry to delicious. Angry looks always from women, to stares from men and boys that I knew wanted me. I loved working it for the men, especially if they were with a woman. I was intentionally being shockingly sexy, slutty, and loving it!

One of my favorite outfits that always got attention was a very tight form fitted leather dress with a very high collar and long sleeves to the wrist. I'd wear my hair up in a tight and severe bun. I'd wear way too much noir black makeup and knee-high soft leather spike heel boots, very S&M Mistress-like. I used that outfit off the street too, used it for some of my 'bad little boys'.

I'd go to a coffee house or an outside street café and just sit sipping a drink at a table. And I'd watch everyone around me. Usually I'd wear very sexy sunglasses so I could see them looking at me but they couldn't see me looking back at them. This was so much fun that I would have done it every day if I didn't have the clients I see keeping me very busy.

On one of these occasions a young man actually came up and asked if he could sit at my table, so nervous I thought I could see him shaking. I almost started laughing. He was so cute! He was a very well built sexy hansom young man, couldn't have been over twenty years old. A college student I found out later and he was exactly twenty years old and had the tight body to prove it.

I smiled up at him, "Why not, baby."

He was all compliments, was quick to tell me how he loved my look. I thought I would shock him when I leaned in and whispered into his ear. I put my hand on his leg, told him, "I'm not a real woman".

I laughed out loud, quickly leaned back and watched his face, smiled at him with that dirty little look in my eye. I dropped my dark glasses to the end of my nose and winked at him. I laughed even louder when he said he didn't care, said he thought maybe I was a tv-girl anyway and was hoping that was the case, said that's why he came to my table.

That's when I got serious. I asked him if he was a naughty boy, if he needed to be scolded and disciplined. I wasn't afraid of being outrageous, far from it. I was having fun, could have cared less if I scared him off. I leaned in close again so that nobody could hear me, ran my hand up his inner thigh under the table right up to the crotch of his pants.

"Go get me a mocha latte and a piece of cheese cake. And be quick about it!" I pinched his crotch and watched him stand and hurry to the counter. I also watched other people with their eyes glued on me. I was truly enjoying this.

He was sheepish, a natural submissive, made me push him even more at the table. When he returned with my order I told him that he should refer to me as 'Mam'. I told him that he got very lucky that day.

And so did I. When I finished flirting, teasing, milking him for the information I needed about his submissive fantasy, I set a date. I told him he was to be at my condo and not be one minute late. He was to stand on my porch and ring my bell not one second before or after his scheduled appointment. He was to ring exactly on time.

And he was twenty minutes early as I remember for our first 'date'. Seeing him stand at the door, not ringing my door bell one second early, just starting at the door staring at his watch, I knew he'd be one of my favorites. And he still is, to this day.

This I also remember thinking. This was going to be for me, all mine. My own selfish little dalliance that had nothing to do with my boyfriend or club-owner pimp, I was going to have some fun on my own.

And I did. He takes me to lunch regularly. I always dress way over the top, him having to be looked at by all that pass us by, knowing what I am for him. It's a given that everyone that sees us knows what we're into. I even have him wear a collar, love that! Sometimes I have him take me to the mall to go lingerie shopping, him carrying my bags. I walk him around like a little dog.

His thing is kissing my rear through my clothing. He is not allowed to touch my bare rear end, even see it. He never sees me naked, ever. Dresses, skirts, girdles, panties, he kisses and worships me through my clothing. Him, completely naked and on a leash, it's his place and he knows it. Sometimes I have him lick my little thing through my panties until I almost cum, have him make me hard. I never cum in front of him. That would be inappropriate and ruin the dominant mystique I have going with this little slave boy. Besides, that's not his main reason for seeing me.

His main thing is being whipped with a riding crop, whipped hard after he kisses and licks his Mistress until she's satisfied. As hard as he tries he never does it respectfully enough.

My masochistic little boy-toy, I've taken him to the point of no limits. I don't hold back on him. Have him trained to take my riding crop up between his legs and deep into the crack of his rear end. The whipping horse in my playroom gets a lot of use since I met this man. He likes the welts I leave on his rear end. And he can take full strokes to his balls, love doing that to him!

And I make him 'confess'. He must confess to me about his masturbation sessions while looking at his welts in a mirror when away from me. He must confess his love for me. That's a big part of our session always, his confession. He even cries sometimes, so very touching. He truly does bring out the sadistic 'mommy' in me. Get hot thinking about petting the side of his hansom face after his confession.

I did tell my boyfriend about him early on. He said, 'have fun, just don't let it get in the way of your real work'. That and 'don't EVER fuck him'.

I don't, would never do that. Another of my favorite things to do with my boy-toy is to masturbate him almost to the point of cumming. Stroke him with K-Y and a rubber glove, drive him crazy. I take him to edge but never let him cum. I've told him he's never to do that in front of me. I tell him that would show disrespect for his Mistress, tell him that if he cums I'll send him away. I'd never tell him this but I love the feel of his cock in my hand, one of my favorites. It's hard not to go down on him sometimes. He's always very good at letting me know when to pull my hand away, he's actually afraid of cumming. And I like that too. He's a very well trained little puppy.

And here's the fun part. I make him pay just one dollar to visit me. He has to give me one single dollar at the door when he leaves. It's so kinky to see him kneel and look to the floor and say 'Thank you, Mistress' and hand that dollar to me and then leave!

He also pays for any lunch date and place I choose. Him being a college boy I don't make him pay to dearly. This is purely my little game, my fun. My client tips and the extremely generous allowance from my boyfriend more than takes care of anything he could ever give me. And maybe one day he'll be a rich doctor, go onto my real client list, who knows. All this from a chance meeting at a coffee shop, did I tell you that I love my life!

So, this is me. A kept little sissy princess whore. Sounds like that would be an insult to say to someone. It's not, turns me on every time I say it. You can refer to me as a sissy whore anytime you want to.

And I probably have at least fifteen to twenty more good working years before I start to look like, as they say, a 'MILF'. But even that won't be bad. I know the boys will still want me, especially my bad little boys in need of discipline.

Makes me laugh to think about that, told my boyfriend about that, we've talked about how men want the young ones. He has set me up very well for the future, puts money in my bank account and keeps me secure and safe. And he tells me that even if the others should not want me, he will. He's the only one I truly enjoy fucking other than my photographer lover. I like my work but he is IT, still the one that moves me and makes me think about him when he's away. Like I said, he's a good man, a very good man.

Stay tuned. Maybe next time I'll tell you about some of the men I see in detail, tell you all the dirty little things I do for some of my 'special needs' gentlemen. Maybe tell you about the one on his way to my condo now. Have to run, my phone is ringing and from the caller ID I know I have to go make myself presentable.

Ciao