Its many years since I started crossdressing and why ? Well who knows but I always remember when my parents went out I used to love wandering round the garden naked even when the neighbours were in, probably first signs of being an exhibitionist. I also used to go to the local park, a small affair next to the main road, but it never stopped me wandering in it naked despite the cars being able to see me.
The change from exhibitionist to crossdressing came after marriage when I purchased some lingerie for my wife but she rarely wore it. She was an excellent cock sucker and never let me down in bed but would never dress up for the occasion. That led me to wondering what it would be like in Stockings and heels then on to what is it like to suck cock.
Work always got in the way but after being made redundant time became available and I made my first trip to see a man, I was nervous, excited, scared all in one. I was dressed in basque, stockings and thong and was met at the door by a man eager to explode. I knelt in front of him and that was all he needed, he dropped his house coat, thrust his cock in my mouth and pumped, withdrawing just before he came. As usual with first experiences it did not do a lot for me but I was sure that their was more to it than a rush job so I stayed on SH to see if anything else would happen.
Since then I have increased my wardrobe and now dress very office like but with very short skirts, I still love basques and stockings but now top it off with a lacy top, fishnet stockings, heels and a jacket, in fact reasonably passable to most people.
My best experiences were of course memorable, one with a lovely couple, but the most memorable was with a lady, lets call here Tracey. She invited me to her place saying I could arrive dressed if I wanted. Even I was suprised but did as she asked. I left home and stopped about 2 miles from her hose and changed. The outfit I wore was that of a whore, a very very short black and white skirt with a top, basque and very viewable stockings. She left me at the door for a minute, teasing I think then oh what a site to behold, she was short, jet black hair. with a cardigan exposing her black bra and ample breasts all topped off with a midi tight black skirt and heels. She took me upstairs and asked if I would take photos which I did with trembling hands. She opened her legs and at that point I could not resist and my head dived to her panties and licked and kissed her gorgeous mound. It wasnt long before she came, her sopping wet panties discarded and her top, bra and skirt on the floor. She had a heavenly body, amazing breasts and a taste to die for.
I left dressed as a man as she thought my arrival costume a bit risque but most enjoyable.
It was sometime before meeting another lady who enjoyed me dressing but plenty of men have enjoyed my company in the meantime, some memorable and others not and of course the proverbial time wasters.
My next meeting came this year, a big beautiful lady and one who can kiss for England. I met her on a site and she invited me round. The first meeting was cautious on her part but when we kissed, oh wow. She lifted her top and I immediately removed her bra to reveal the most amazingly huge breasts which I could not keep my hands off. We didnt have long at that meeting so I was only partially dressed under normal outer clothing as she was having a friend round so I left early.
I met her again a few weeks later, her lodger was in, I took her to her room whilst he was in the garden just near her bedroom window, I put heels on after removing my male clothes and I was wearing a basque, stockings, panties, mini skirt and heels. She loved it, I helped her strip naked, my first Big Beautiful Woman and wow what a site to behold. Her breasts were enormous and so much to enjoy and explore. I sucked her nipples and my hands explored her body with my tongue. It wasnt long before I had my fingers in her and my tongue licking the outer edge of her delicious shaven haven. I kissed and licked and she was soon breathing loudly before giving out a deep moan. After that she sat up and asked if I wanted my cock in her mouth and she obliged with me cumming all over her beautiful breasts.
All this with her lodger just sat outside the window.
I hope to return next time to an empty house and who knows what we will get up to.
I have now been a CD for many years and hopefully as long as my legs are still as good as ever for many years to cum.