It was probably in the late 80’s that I had my first experience with a crossdresser. I was working as a rep in the Birmingham area and would often stop around midday to have my lunch. This particular day I pulled into a lay-by alongside some woods.
I wasn’t paying particular attention to people passing by as I ate and read my paper except this one guy walked past my car a couple of times , I then noticed him walking into the woods and looking over at me. I had no idea what was going on but curiosity got the better of me and I followed him in.
He seemed to disappear but as I walked around the corner there he stood with his suit trousers round his ankles wanking away what seemed a nice size cock. He was wearing french knickers suspenders and stockings. I just stood watching but could feel my own cock starting to get hard. I began to rub myself through my trousers. I had never been with a guy before but was now sporting a huge erection.
I had never been with a guy before but felt so aroused that I walked closer to him.
He started rubbing me through my trousers then undid me and released my erection. I reached over and touched the first cock of another man.
He crouched down and took me in his mouth. I could have cum immediately but held back. After a couple of minutes he stood up and it felt the most natural thing to do to return the favour. Within 5 minutes I had touched someone else’s cock and now here I am giving head.
After a short while I stood up and the guy reached in to kiss me. What was I doing?
I know exactly what I was doing I was loving it.
Once we both had ejaculated we walked back to our cars not a single word spoken.
That night when home I felt utter disgust in myself. This would never happen again. How wrong
One week later I made a point of stopping at that same lay-by. Plenty of guys going back and forth but now I knew why. After a few minutes I went in and met this middle age guy who didn’t have his cock out but was rubbing the front of his trousers.
I did the same then followed him to a more secluded area. Mutual masturbation and once again nothing said.
This continued for many years stopping at lay-bys , toilets and anywhere that I knew I could get some cock.
This all led onto my own cross dressing and now some 30 years later I regularly go out dolled up to local hangouts looking for fun. I have been caught by the police after having been with a guy in local woods coming out with hair all over the place and smudged lipstick but wasn’t ever charged as they hadn’t actually caught me doing anything
This is a completely true story I was probably 23 at the time. I have kept my dressing secret from my wife of 20 years but any opportunity I get to dress I take