Gay Sexual Stories

Gay male, lesbian and bisexual sex stories collection

Tag: Transvestite

Two friends explore their sexuality

I was 20 years old, a sophomore in college, and was living in an apartment with a friend off campus for the first time in my life. No one in my circle of friends had any idea that I had always felt like I was a girl in my mind. Living in the deep south in the 90’s, it wasn’t an option to be honest with people. If you had these feelings, it would be in your best interests to store them as far back in your mind as you possibly could.

No one had a clue that I wore …

A crossdresser takes the next step

It was going to be just another fun night. I was finishing fitting my wig and started outlining my lips with lip liner, and followed up with some Revlon red lipstick. While not great looking, I had a great pair of lips when painted with lipstick. For the past few years, when going on business travel I always took the early flight and packed some of Brenda’s clothes so I could crossdress as soon as I got to the Hotel. I had been a closeted crossdresser for years. Tonight I was going to wear a very pretty red and black …

Wearing my favorite lingerie while camping and I get some unexpected visitors

While In college I enjoyed visiting a small state park camp ground not far from campus. The sites were far apart from one another and the trees were thick, so I was pretty isolated and out of view of other campers. I had been cross-dressing for years and enjoyed being alone in the woods where I would wear what I wanted undisturbed. I still lived in the dorm on campus and didn’t have much privacy, so I treasured my weekend getaways. As I set up camp, I had a bra and pair of panties on under my shorts and t-shirt …

The story of a teen boy giving into his desires

John had always been a little bit different. At a young age he had discovered porn. It started with pictures and magazines. Then the internet brought him movies. He became addicted. First it was straight porn, then interacial. Then he discovered strapon femdom witch quickly led to transexual porn. Soon he began sneaking around wearing his mothers panties and playing with his ass.

At 17 he was still a virgin until he joined an adult dating site and met an older man. He lied about his age and met up with him. The older man had been his first. John …