When he reached thirty the urge to crossdress resurged. The little sparecash he had was spent on sexy underwear, shoes, dresses and makeup.In his mid ...thirties he decided to create a profile on a contact site, inthe name of Debbie36. He was amazed at the attention he got. Guys weremessaging him all the time. The massages ranged from polite to obscene.He had fantasies about being a woman and having sex with a man, but neverthought it could actually happen. He met a few of the polite soundingmen.. Like do you remember that time when you were ten years old, we went for a long drive. You wanted a soda as a treat, so I bought one for you - a big one. And after a little while you asked to go to the bathroom.(Bob): Yes, that was wonderful - there was nowhere around to stop, so I told you to hold it in. I loved that you were uncomfortable, but you started to complain too much.(Eleanor): And do you know the funniest thing? I told you this little lie, that we could not stop at the shops we. All their personal luggage was searched.Then came the command "Strip off girls time for your search."The first girl went into a cubicle with a female prison officer and came out looking a little flustered her face all red "the fucking cow" she murmured.The second girl went and Tony knew that soon the game would be up for him because as soon as he was undressed they would soon know that Tony had an eight inch cock where there should be something much more feminine.Then came his turn as Tony. Then came to me and put her hand on my crotch and said “could have ended up in here, if I hadn’t come in”. We both just looked at each other not saying anything but thinking what that would have been like. Mom then said “ I need to know, Have you two done it or been this far with anyone else. Come on, tell me”. We both stammered out the words. NO. Never. Her tone of voice suddenly changed from being pissed to a motherly tone. She said”Well, as I said before I cant change what you were doing,.