Free Shemale Stories

Wife makes me dress like a slut

Back in the 80's my wife and I did a lot of drugs ...she was super hot with long legs and loved to dress in stockings..short skirts...high heels and lots of makeup...and WOW could she suck and fuck !! One night when we were really loaded, she got me to let her dress me in her lingerie...panties,bra,... read more

Diana58cd March 24, 2020 75%

Am I gay?

Please help me. I'm confused and unsure if I am gay. I feel so ashamed of myself. I don't want to be gay but I was molested by my neighbors at 6 years old and from then on I would wear my mom's panties or sniff my sisters while masturbating. Cumming would always make me feel guilty for what I have d... read more

Chinaysissyslut February 24, 2020 38%

Longtime friends

*** This a work of fiction but wishful thinking. Beau and Stephen had been long-time friends, they often spent time together playing golf, gym, and fishing. Stephen had a secret crush on Beau for quite a long time or it was Stephanie, Stephens' alter ego that did have a crush on Beau. He found hi... read more

Stephanie_logan February 21, 2020 72%

Crossdressed Lana - Hannover, Germany

Crossdressed Lana - Hannover, Germany Very Sexy & Compliant Sub-Slut Is Searching For Kinky BDSM Live-Dates At Hannover, Germany!!! I Am Bisexual And Want Men, Woman, Couples And Trans For Outdoor, Swingerclub, Porncinema And Public Sex. I Love To Wear Very Hot & Sexy Clothes Like Lingerie, Stoc... read more

Crossdressed Lana February 6, 2020 62%

A day in the life of Amber

This is how it was … I looked nice for you and wore my pink polka dress with suspender seamed stockngs black bra and panties white gloves and my spiral earrings and painted my toes to match my lipstick – then changed into my red/black 2-piece then wore both of my babydolls and you can see a photo... read more

amberdoll January 27, 2020 85%

Making a date with a shemale escort

I am an older..60..closeted crossdresser...love to dress like a slut every time I can hide from my wife...who knows nothing of my secret life as Diana. I have been unsuccessful at finding another cd to play with....dressing slutty..taking pics...and lots of foreplay before I kneel down for her. I ha... read more

Diana58cd October 29, 2019 83%

My Neighbor

When I got divorced and was finally living alone I had many fun times getting fucked all I could by both men and women. I was always dressed when home and loved to stay that way all weekend long and would just put on some pants over my outfit to go shopping sometimes with a coat or shirt over my ope... read more

crossdresser55 October 29, 2019 92%

The trip

I was at work and they decided that some of us had to go to Florida to work on some problems so I was picked. I went home and packed and made sure to pack some of my sissy outfits also because I would be in a hotel for 7 days and have the room to myself it was perfect. The next morning me and the ot... read more

crossdresser55 September 18, 2019 92%

The Sex Club

When I got divorced back in 1987 I was a very horny man that had not had sex in many years. I had always liked to dress up in nylons etc and learned long ago that I was Bi and liked cocks and pussy. When I finally got my own place after the divorce I almost always would lay around the house dressed ... read more

crossdresser55 September 11, 2019 85%

Vacation fun

I was staying at a nice hotel for a week while working and in the evening, there was not a lot to do so I decided to go for a little walk along the nice pathway they had at hotel. It was very private and wondered around a bunch of flowers and trees and brush and along a nice little river. I had walk... read more

crossdresser55 September 11, 2019 80%