Crossdressing(5)

14

My first time in a bar

The first time I met a guy in a public bar for a drink

For a while now I had been chatting with a sweet guy named Allen, who was bisexual and was eager to meet a crossdresser. He was very muscular and handsome, a hard body but with friendly eyes. He seemed to really like my pictures and said he had cum, stroking himself, while looking at them several times, and was eager to meet me in person. He wanted to meet in a bar which is something I had...Read On

29

My first time outdoors

My first time dressed outdoors for sex

It had been about a year since my first time with a man and I had been with a couple more since. They were enjoyable experiences but I had failed to capture the thrill of the first time. I had continued to talk to guys online and a lot of them were trying to convince me to go for a drive with them to a secluded spot for some risky sex. I was reluctant for several reasons but the fear of...Read On

30

My first time with a man

Crossdresser in slutty latex clothing fucked buy a man for the first time

I had been into dressing in kinky little latex skirts and dresses for years. I loved the way they felt against my skin. Playing on my own had been enough until now, I had toys and vidoes to amuse me but the thrill of being fondled and fucked by a real guy was now too much to resist. I decided to try the online sex sites to find someone and find someone I did. He had looked at the pictures I...Read On

26

My First Time With Two Guys

I got more than I bargained for when I met a guy for sex

I had made a date with a guy I had been exchanging emails with on and off for three months. He seemed nice enough and was pleading with me to meet with him. He convinced me to meet him at a nearby hotel and left the key at reception. Then, he was going to wait at the bar whilst I got ready and I would text him. Then, he would come up to the room and let himself in. I arrived at the room,...Read On

10

Soldier Standing to Attention

A soldier and the slutty nurse

I had been flirting with a soldier that I had met online for a while. He was a lot younger than the guys I normally go for, but surprisingly open minded for his age. He was also really hot and had a nice body, so I agreed to meet. We toyed with the idea of some roleplay during our online chats. My favorite was the wounded soldier and the slutty nurse; it made me very hot. I got myself a...Read On