I First Time Sex As a Crossdresser

My first time as a crossdresser happened not long after my ex and I had broken up. During our relationship she had told me that she wanted to see me with another man. I wasn't comfortable with that as a 20 year old man so I turned her...

well here ti goes this my first telling my story it all hape it was about 8yr ago i was living just me and had a good job was biying women thing off ebay oh boy i had fun back then on my days off from work i usely dress well one a man...

Hi this is my real life story finally i got the the chance to reveal........being in a family with 2 sister and mother i was less interacted with boys.....i still remember my sister used to dress me like girls i really used to enjoy...

I met Tommy when I moved in to my first appartment when I was eighteen, he had helped carry some cases upstairs for me. My furniture had been delivered the day before so as soon as he left I took my jeans off pulled on a short denim...

Many years ago I had a fling with a lady at my workplace. I was stunned that she showed an interest in me at all. WOW, she was fantastic. This was the usual girl-guy relationship. Then one time, after we had sex, I was watching her...

Hi this is my real life story finally i got the the chance to reveal........being in a family with 2 sister and mother i was less interacted with boys.....i still remember my sister used to dress me like girls i really used to enjoy...

Iposted an ad as a CD and a picture, I am not at all passable, but I have nice latex mask and chest, with a nice set of 42 DDD tits on it and their soft and pliable, anyway, I got allot of responses, I chose a nice guy that is fit and...

I was 17 and a junior in high school.  I was a closet crossdresser, but always wore a bra and panties to school.  I never thought anyone could see the outline of the bra through my shirt.  One day I had a classmate come...

Like so many others my first time in girl clothes was on Halloween when I was 13. My friend Johnny and his sister decided I should dress in her cheerleader's outfit for Trick or Treat. So here I am walking all around town in a tiny...

Having been crossdressing since I was 5, people who came to our house just never paid attention any more. My sister is 3 years oulder then me a senior in highschool. One day mother was off to work, my sister was dressed and told me her...

When I was 15 I joined a hook-up site (lied and said I was 18) and met a lot of guys. An older one around 50 stood out the most and seemed like the most fun so I agreed to meet up with him just to talk and go from there. I bused down to...

Was with my best friend, Alan when we were 15 years old. We had been suck buddies for about 6 months or so and one night in a tent in the yard, we both allowed each other to fuck anally so we knew what it was like.
Then one Saturday my...

Ok so this wasn't quite my first time having sex with a man as a crossdresser but it was definitely the best. I had sex with two other men before "Andy" but was largely unsatisfied with the experience and decided to give it another try...

I had been a crossdresser for years, but only in the past few years have I gotten curious enough and brave enough to try sex with another man. To make a long story short(er), I finally got up the nerve and set up a meeting with another...

I have been a crossdresser all my life. I don't advertise the fact that a large part of my persona is feminine but it is obvious. My wife has encouraged me to accept who I am though she doesn't like me to spread the word as it wear. For...