Shemale Stories

As you walk into the room, I sneak up behind you, and put my hands gently over your mouth. As you start to panic, I whisper into your ear. “Don’t be afraid. Just do exactly as I say, exactly how I say. Do you understand?” I can feel the smile begin under my hand as you nod your agreement. You know that the evening should be quite enjoyable. I pull my hand away from your mouth, and run it gently over the back of your neck, as I move towards the chair.

Read more: Shemale Sex Story Hidden Desires

Loraine and I hadn’t had any sort of relations for over two months. And even though I had fantasized about sucking on that cum soaked pussy of hers and rubbing her pregnant belly - it was totally out of reach. Richard, my wife’s boyfriend, had all of her time. I think she was falling in love with him.    The strange thing was, I wasn’t hurt or sad but very happy for her.    I was busy with my own life. I had the store to run and in bed Andy kept me completely satisfied. Sometimes I thought that I loved him more than I could stand.  Also, keeping up with being a woman was  getting more involved and fun.  Lorraine and I decided that we would have a great sex life….If I were made a woman.  And so it is…

Read more:  Shemale Story - Making Kristy

I’ve been working the streets for a long time and I know all the ends and outs of the flesh market. I have six she-males that work for me and I get 50% of everything they make plus all the sex I want, any time I want it. I make them work seven days a week rain or shine.   I buy their clothes and tell them what to wear and when to wear it. I have a little black book with a lot of clients in it. Some of my special clients are women they love to see the she-males jack their cocks off and eat there cum.

Read more: Shemale Story - She-Male Pimp Daddy

Michael sat at the table playing with his drink. He’d gotten his first real paycheck today and decided he deserved a dinner in the best restaurant he could afford. Of course which what they were paying entry level trainees at Donaldson & Rhobes, his choices quickly narrowed to a few. So he found himself on 11th Avenue instead of Broadway, but still he felt like he was on top of the world. Not bad for a kid from the sticks now living on his own in New York City.   The 21 year old was looking as to where his waiter had vanished to when he first noticed her, sitting at a table over in the corner.

Read more:  Shemale Surprise Story - Silk Scarf

Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locker, but it was no major deal. After all, Marilyn Walker was used to being looked at. After all, how many 6′3″ girls wear 4 inch platform heels? How many 6′3″ girls are there? Oh well.

Read more:  Tranny Story Special Shemale Fun

The third Friday of every month is my day. This is the one day, or rather night of the month that I truly look forward to. Only twelve times a year, do I allow myself to totally, absolutely indulge myself. To be a slut! A total tramp! To luxuriate, and fulfill my desires that have been pent up inside me since the last month!   To enjoy fully the sexual cravings I have, the cravings I stifle until that one night on the town when I unleash the sex crazed lust starved animal passion inside me. The night I go on the prowl!

Read more:  Shemale Story - A Night On The Town

On Friday afternoon I had the car go around to collect Krissy at her office, then my wife, Mei, from home, and then me at my office. The girls were both wearing light, summer dresses and looked beautiful! Unfortunately as I was coming from the office I was wearing a Suit (But as usual with Black Lace top Stockings, Garter Belt and panties underneath!).   The Jacket and Tie were soon removed, then a drive out to the airport. Traffic was not too bad for Bangkok, many people took the previous week off as it is school holidays. The flight to Koh Samui is very short, less than two hours, as we were landing we looked down at the ocean, the water was so clear that you dould see the bottom! The hotel car was waiting for us and we quickly arrived and checked in.

Read more:  Shemale Sex Story Thai Holiday

I would want a good group of six people. I’d like to be divided evenly men and women. Of course it would help if all were bi-sexual. That way, I wouldn’t have to look up when a large cock would be near me. I could suck it dry just as easily as I would eat a piece of twat. If some of the folks would be into water sports as well, that would be icing on the cake.

Read more: Crossdresser Sex Story My Fantasy