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A couple of years ago I had a girlfriend named Sara, we met at work and were starting to have a great relationship. In the bed things started to get interesting and we got more and more kinkier ever time. We would tie each other up and and play with each other. Then we started using chains and gags and having a great time. Now, she has always had bisexual tendencies but at the time I didn’t know about them. One Halloween she asked me if I would dress up as a girl for her. I asked her why but she said that it would be fun.

So, I thought, “why not?”

Over the next couple of weeks we shopped for outfits and dresses and heels and hosiery and other things. She then started shopping for panties, I asked her why, and I told her that I would just wear my regular underwear underneath. She said no that I had to have the full experience. To make her happy I just agreed and moved on. She chose a strapless pink prom dress with a black sash for me and black 6 inch stiletto heels and pink ruffled panties with nude stockings. To top it off she had gotten me a long black curly wig to finish the ensemble.

Halloween came and I got my cute little outfit on and I felt, well, different. I felt, good. I couldn’t believe how good I felt wearing this. My girlfriend came and and reached under my dress and felt my hard cock standing to complete attention. Her eyes got wide and she said that she didn’t expect that reaction. She had a really sexy schoolgirl outfit with a red plaid mini and white thigh high stockings and 5 inch chunky heeled mary janes and a white blouse. She had small but perky a cup breasts and long red curly hair with porcelain white skin. She was an image indeed. We went to a friends party and had a great time. But what happened in the later weeks was nothing short of interesting.

She worked late nights as I worked days. Halloween was over for about a month and I was home watching tv but I got the urge to look through Sara’s clothing. I went through it and found a cute French maid uniform. I pulled it out and put on a pair of her black boyshort panties and the white stockings she used with her schoolgirl outfit and I put on my stiletto heels and my wig again and I pranced around my apartment looking in the mirrors. Well, Sara came home early. She came in and saw me in the outfit and her mouth just dropped to the floor.

“Why are you wearing my maid uniform?!”

I couldn’t speak.

She came over to me and put her hand up the skirt of it and found my clit hard again. She told me that she didn’t expect this to go this far. She told me if I wanted to dress like this, I was to be her own personal sissy. She ordered me to make her dinner. I went and started dinner but I was only to make enough for her and her alone. I made her dinner and served it to her. She sat down at the table and I stood by the table watching her. I could only look at the floor because I was so embarrassed by what had just happened wondering how this would play out. She then looked at me and told me to get under the table and lift her skirt up. I got down on my knees and did as I was told crawling under the table to find her dripping wet cunt seeping through the panties.

She then reached her hand under the table and pushed my head into her pussy and said, “Eat me bitch.”

I started licking away at her love knob and stuck my tongue deep inside her hole. She had an amazing orgasm and came all over my face. She then saw that I was still really horny and got up and went into the bedroom. I got up as well with her cum still all over my face and went into the living room. She came back with her giant 10 inch black dildo and ordered me to get on my knees. I did as I was told and felt a cold liquid on my rectum, then her fingers. She continued to stick more fingers in and then jammed the dildo straight in. I screamed with pain but she slapped my ass and told me to take it like the girl I so desperately want to be. She continued to push it in and out until I couldn’t take it anymore and shot my cum all over the floor. Sara scooped it up and put it to my mouth and told me to swallow it. I ate all of it and licked her fingers when it was all over searching for more.

She said, “there will be plenty more to cum my sissy boy. From now on you are my slave and I will be able to have lesbian sex with women like I always wanted to. The only sex you will have from now on will be eating me out and having me fuck you with this dildo.”

There was no way to know what the future held for me……

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My name is Jim Carson. I was 5-10 at the time. Kind of skinny at 155 lbs. And not much experience with the girls at my school. A couple of them had said I was cute, but it seemed they liked the stronger, hot guys better. Oh well, I was young, there was time. Maybe a new hair style would help. I took the bus up the avenue and got off a block from Cricket's Hair Salon. I wasn't too sure just yet. After years of going into the local barber shop for a trim, this was a different looking place. I...

Peters Promise

Peter sat in shock as he listened to his fiancée finish her statement. His anger surged through his body. Pete was driving to the show for their regular date when he asked Polly if she wanted to take a week and go camping with him after her college classes ended next month. Polly said, "Pete you know I am leaving the day after classes are over. Shelly, Emma and I already have almost all our things packed ready to leave. You know we are taking the whole summer for a trip out west." "Polly if...

Massage That Turned Her On

Hello, sex story readers, Like everyone else, I’m also a big fan of Indian sex stories and of all the stories shared on this site. Some stories are so amazingly written that you could literally visualize every minor detail while reading. So I too have tried to keep the story descriptive and full of details, in order to take you to a sensual and steamy journey. And guys forgive me for my grammatical or spelling mistakes. Plus, I would love to know about your experience or feedback. So, you can...

How Wonderful to Know

My ex-wife was sitting in front of me and crying her eyes out. "You must have something left from the divorce settlement. After all you did get 1.3 mil from the sale of my business and our house." I asked her as I offered her a glass of water. "We invested it all in stocks hoping for a good return and lost most of it in the economic downturn. Jed was out of work for last six months and we were spending from our savings." Sandy spoke between her sobs. "What do you want me to do?" I...

The Babe Bike BluesChapter 11

"I want to see your father," Susan said, her voice stronger now. "And I'm so thirsty I feel like I might turn to dust and blow away." Jennifer blinked. Her face still felt hot from blushing when she realized her mother had actually heard about the masturbation and trying to get Uncle Bob into bed. But her mother's reaction threw her for a loop. She jumped up. "I'll g-g-go g-g-get a nurse!" she yipped. Wanting to see her husband seemed like an eminently reasonable and simple...

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