Transsexuals & Crossdressers Stories

15,868 results
Orientation
Length
Source
Infinite Scroll

Weekend at Alice's Cottage Ch. 07

by pantycladlad on Sep 19, 2017
Transsexuals & Crossdressers

Alice and I both awoke at about the same time. A quick trip to the bathroom for each of us and we headed downstairs together. Kathleen was sitting in one of the overstuffed chairs reading the newspaper and sipping a cup of coffee. "Good morning sleepyheads," she greeted us. "Stay in your nighties, if you want, and join me for a cup of coffee." We soon bot...

Unconditional Love Ch. 05

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

It had been a year since I started dating Alison. We had gotten really' close in the time that we had been together and we were by each other's side practically all the time these days. I loved her so much and I knew she felt the same. Our sex life' that had only gotten even better since I actually started giving her blowjobs. A few times, she had brought u...

Unconditional Love Ch. 03

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

I stood for a moment, after shutting my bedroom door, trying to get everything that had taken place to register in my mind. Alison was indeed a transsexual, her cock was definitely bigger than mine' and I had just come very close to having sexual intercourse with her. She'd' given me a blowjob and she had licked my asshole, which was odd, but it had felt go...

Becoming Cassie Ch. 11

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

On New Year's Day, I slept late, real late. I was still trying to process the month of December. It was clearly a month I would not forget. I did a lot of daydreaming that day and watched TV with the family. I was pretty zoned out. New Year's Day simply came and went. My cell phone rang early the next day and I was asked to price out 2 different painting j...

Sissy Housewife Learns to Eat Cum

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

Only a few days after Miss Jennifer agreed to let me be her housewife, she informed me that now that I was "pretending to be a girl" and was required to always be dressed completely as a girl, she expected me to service her the way one girl would service another, with my mouth and tongue. At least three times every day (always in the morning before she left...

Making Work a Better Place Ch. 06

by FinalStand on Sep 13, 2017
Transsexuals & Crossdressers

It was a week after the vacation and I had noticed that Paulette was reacting to me oddly. I've asked Peggy about it, but she told me that things would work out. Peggy has sent Paulette an e-mail telling her to come to my office at 4:45. Peggy has already gone for the day. Paulette shows up promptly, looking so worried that I immediately shut down my Mystery...

Melissa's Ordinary Day Ch. 05

by Floydman1 on Sep 15, 2017
Transsexuals & Crossdressers

Note: I highly recommend reading this series before beginning this story. Thanks to everyone who has voted so far, the encouragement is very flattering! I hope you enjoy this next chapter in Melissa's journey. ***** It had only been three days. Just 72 hours since that night that Jessica had revealed more of what was going on with her. They had been enligh...

A Lost Bet Ch. 05

by amarasfantasy on Sep 12, 2017
Transsexuals & Crossdressers

I slept soundly that night. For the first half off the night, I don't think I moved from the position in which I'd crawled into bed. I do remember waking up though, about 2 or 3 in the morning, to use the bathroom and get a drink of water. Upon returning to bed, I drifted off into a sleep filled with vivid dreams...much like the night before. This time, inst...

Making of a Porn Queen Ch. 07

by Scribler on Sep 25, 2017
Transsexuals & Crossdressers

Over the months Helen and I became quite close. Normally on Fridays we would go out together and have some fun. At the end of the night she would usually come home with me and we would spend the night together. She would stay the weekend and spend some time with Tracy and Mark before she went home late Sunday night. There were times when the four of us and...

Lady In The House Ch. 13

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

I awoke in my cell the next morning unaware of the terrible fate that had befallen my sister Angie. I knew that Steve had sent his henchman Danny to do something to her in retribution for my recalcitrance but I didn't know exactly what that evil bastard Steve was capable of. I lay there shivering with dread hoping that Danny had just given Angie a warning,...