Gay Cross Dress Stories

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Cross-Dressing, Gay & Lesbian Sex 05

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. * Daniel's one time bi-sexual fantasy consumes him "Maybe if you allowed me to have sex with Martin," said Emma to Daniel pausing without finishing her thought. She looked at him with teasing eyes and flirty sexiness in the way she used to look at him when t...

Cross-Dressing, Gay & Lesbian Sex 04

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. Daniel and Martin swinging in a foursome, k-i-s-s-i-n-g. * "One more thing?" He looked at her as if she was about to ask him for a divorce. He looked at her as if she was about to ask him if Greta, Maureen, Ebony, Janya, and Veronica, along with Martin, coul...

Cross-Dressing, Gay & Lesbian Sex 07

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. * Emma and Daniel invite Veronica and Martin over for some sexy fun. Daniel and Martin have bi-sexual sex while watching their wives having lesbian sex "Won't you join me?" Directing his conversation to his cock, Martin gave Daniel's big bulge a raised eyebr...

Cross Dresser Escort Swallows Cum

by Alluring_Crimson_Shifter on Apr 3, 2019
Gay Male

The sun felt good on Don's suit and tie. The breeze tussled his well trimmed hair which fell back into place thanks to his hair spray. Smelling the fresh cut grass and the blossomed flowers he pleasantly gazed about the well kept city square. Charismatically he smiled at other walkers whether dressed casual, or in business attire. City traffic noises were ca...

Sissy con carne

by WinterBreeze on Jul 1, 2017
Gay

Sissy con carne Chilli night turns much more fun! Synopsis A young guy discovers his girly side and dives right into all the fun! Chapter 1: Introduction You've always known inside that you we're far less heterosexual than everyone might think. It's been a long time since you imagined you were the man getting sucked an......

Rick Needed a Beer, Gets Much More Pt. 11

by Iwanttwo on Aug 12, 2019
Gay Male

This chapter may better fit in the cross dressing category, but I'm keeping it in Gay, as past and future chapters are gay stories. And this chapter does involve some hot gay sex. I recommend you read previous chapters first, if you haven't already, to understand the characters. —————————————————— Tuesday at the office was awkward, to say the least. I avo...

Sissies love big black cock

by Yelawolf on Nov 16, 2017
Gay

Sissies love big black cock Sissy vs bbc Synopsis Story from edithis Chapter 1: Introduction Welcome to the story you crazy sissies and you strong aphla black males. This is from edithis and I want to bring here so you guys can write or read or for the real reason you're here to masturbate. Get your hand, dildos, lube,......

Amish Fun

by Michele G on Aug 18, 2017
Gay Male

I'm Michele, a 19 year old cross dresser. I enjoy going for long drives out in the country side. Sometimes I would pass farms where there were young Amish men would be working. On hot days the men would take off their shirts as the toiled in the fields. I almost wrecked on a number of occasions staring at them and wondering what it would be like to have one...

Putting Myself Through College Ch. 09

by RobXXX on Aug 31, 2017
Gay Male

My Spring Break assignments were not finished, just my time pretending to be someone I was not, well at least the sex I was not. I received a call from Kevin the day after the cross dressing assignment, he apologized a little bit for the previous day, then jumped right back into work. That night he had another client for me, this one he said was a known cl...

A Fantasy Cums True

by lovestosuck2007 on Sep 15, 2017
Gay Male

I have to admit that I have been at least bisexual my entire life. I am a 48 year old married man who besides loving to suck cock loves to cross dress. I have kept this hidden from wife which explains why I don't get to do either very often; at least not until I hooked up with our neighbors son. Our neighbors had moved in when their son had just turned 18...