I have cross dressed for almost fifty years. It started in the UK when I was eighteen, I had often read the various catalogs for mail order purchases and used to look at the women's lingerie pages where the ladies were wearing garter belts, girdles, panties, stockings etc., and I used to get hard and play with myself and jack off to the pictures.
I was always fascinated at my older sister who used to wear stockings, garter belt, etc. and it excited me. One day when nobody was home, I went to my sister’s bedroom and looked in her drawers and found a black garter belt, a pair of black stockings and black silky lace panties. I was feeling very horny and decided to put them on. First the garter belt, then the black nylon stockings and then the panties.
My cock was rock hard by the time I had everything on and I stroked my cock through the panties and ran my hands up and down the silky-smooth black nylons on my legs and it felt incredible. I liked it so much that I jacked myself off in her lingerie. It was such a great feeling that I couldn't wait to do it again.
It became a regular thing and I would long for my parents and my sister to be out of the house so I could dress in her stockings, garter belt and panties etc. I very quickly became hooked on this and loved the sexy feeling of her lingerie on my body, it felt so sexy and I would get so turned on that when I jacked off I would shoot really big loads of cum each time.
Later my sister got married and moved of our house and I didn't have access to her lingerie any more. So I started to go to some of the second hand clothing stores and they had some called Oxfam and Salvation Army just like the Goodwill etc. here in America. These stores would have women's clothing as well as lingerie like garter belts, bras, panties and sometimes if I was lucky even stockings too. By this time in my life I was looking to get an apartment of my own and did six months after my sister moved out .
Once in my own place I could do whatever I wanted and would often go on a search mission to the second hand stores to buy myself some lingerie. I was able to find some quite nice lingerie, my favorite color was black and I quickly found a few black four strap and six strap silky and lace garter belts, some matching black panties and bras as well as several pairs of black nylon stockings as well as a few black nylon or satin knee length slips.
I took them all back to my apartment and washed everything and the next day started to dress up in them. I was so excited and the thrill I got from wearing them was incredible. I would come home from work every day and take a shower and get dressed up in my own lingerie and jack off.
As time went by, I was so much into the cross dressing that I wanted to see if I could go out wearing my lingerie under my regular clothes. I did get up the courage one evening and put on my black six strap garter belt, black panties, black stockings, black bra and slip and then put on my jeans and a lightweight jacket and shoes. I went and walked in a park close to where I lived. It was dark and there was also a public restroom in the park which I saw several men hanging around the outside. I did not know at that time they were just horny and, in some cases, older men looking to play with another person.
I needed to pee, so I went inside the men's restroom and there was a long trough as a urinal with several guys standing at it, and three stalls. Two of the stalls were occupied and the one in the middle was empty so I went in the middle stall and locked the door, I opened my jeans and got my cock out and had a pee. As I was doing so, I noticed the walls on both sides of my stall had very large holes in them and even in the dim lighting in there I could see someone on the other side looking through the hole.
One of the guys spoke to me and said can I see you cock; I was shocked at first then the guy on the other side said come on show us your cock. I was feeling a bit horny by now and did not know what to do. The first guy who asked to see my cock put his hand through the hole and reached for my cock, I backed up against the other side wall and then I felt two hands come through the hole and reach around me and touch my cock which was rock hard by now due to me wearing my lingerie.
The guy in the other stall saw this and put both his hands and arms through the hole and was also touching my cock too. Then he said drop your jeans and let us see more of you. I said no I don't want to, but the guy behind me held me by my hands against the wall to his side as the guy on the other side in front of me undid my belt, unzipped my jeans and pulled them down. He let out a gasp and pulled me forward and told the other guy through the hole what I was wearing.
They said you are very sexy dressed in the lingerie and have made us get very hard. They asked if they could put their cocks through the and if I would jack them off? I told them I was afraid and had never done anything like that before. They said I was dressed so sexy and had made them so hard and horny they needed to get off. I thought what harm can it do so I agreed and they told me to first take my jeans off and let them feel my stocking clad legs up to get them even more horny.
I took my jeans off and hung them up on the door and stood in the middle between the two walls and they both put their hands through the holes and was feeling up and down my stockinged legs and that made me feel very excited and horny. Then one guy stood up and put his cock through the hole, I gasped when I saw how big it was, he had least seven inches sticking through the three inch thick wall and it was very thick, I could not get my hand around it.
I said wow, that is the biggest cock I have ever seen. He asked me to stroke it and I reached and touched it and started to stroke it back and forth. The other guy stood up and put his cock through the hole on the other side and it was least an inch longer and even thicker than the first guys cock. He told me to stroke his cock too and I did as I was told. The guys were loving it and moaning as I stroked their cocks.
Both guys pulled their cocks back through the holes and one guy told me to kneel down with my head close to the hole on his side. I knelt down and he said you stroke cock really good, but with you dressed so sexy and slutty, he asked if I had ever sucked a cock before. I said no I have never stroked a cock before until tonight, and never sucked one either. He asked if I would like to try it, I said I was afraid and he said, "It’s okay, just take it slowly and see if you like it and if you don’t, we can just stop."