When I was younger my best man returned for a visit from Australia so his sister decided to throw a welcome party. As we hadn't seen him for some years we decided to surprise him by me dressing up as a woman to see if he recognised me. I was roughly the same height and build as Vanessa so she looked in her wardrobe for a sexy dress and lingerie and a lovely blonde wig. She and her other sister spent an hour giving me a face over and when finished I looked quite stunning even if I say so my self. I have very soft skin and could easily pass as a woman. When Tom arrived I was introduced to him but he didn't recognise me under the make so we decided to see how long it would take for the penny to drop. Needless to say the party went on and I danced with many guys before one became amorous and asked if I would like to go in the bedroom with him. I explained to him that I wasn't really a female but he said it didn't make any difference, he thought I looked such a stunner he would fuck me anyway. Many years later, after I was married, I got the urge again to dress as a woman so I bought some lingerie, skirts, blouses, shoes, wigs and make-up. I practised making up when my wife was working and began to look quite reasonable. My wife takes a weeks holiday every year with her best friend so I decided while she was away I would dress when ever I could. Eventually I plucked up enough courage to go out in the car fully dressed. I would drive around and park at known dogging sites feeling very excited. I was sitting in my car with the driver door open exposing my stockings and skirt when I a car drew up beside me. Now I started to feel very excited. A young guy got out and walked towards me. When he got to the car he unzipped his trousers and flopped his 8" cock out. "Suck that" he ordered and without hesitation I took it in my mouth. He then grabbed my head with both hands and forced me to take his cock deeper and deeper. As he thrust into my mouth I grabbed his buttocks with hands pulling him towards me desperately. Suddenly his cheeks clenched hard together and he shot his sweet tasting load into my mouth. So much cum was spurting from his cock I had to swallow twice before I could accommodate the load and relax with it in my mouth. When he had finished he withdrew his cock, put it inside his trousers, zipped up and left without another word. I was sitting there contemplating what had just happened, his cum still in my mouth when two lads approached from behind, they had been watching what had gone on and wanted the same so I quickly swallowed the cum in my mouth and started again. Needless to say I was totally satisfied once the two lads had finished and realised I had opened up a total new experience which I felt extremely comfortable with. I knew then I I would pursue the crossdressing further.