Well, I had never even considered women's underwear before, well except maybe it all started with me in the bathroom reading JC Penny underwear ads.
I'll back up, when I was like 11 or so I was climbing the flagpole and got a funny feeling in my crotch every time I pulled my legs up. And it felt better everytime I pulled them up but I wasnt very strong. After a week or so one day I kept doing it and suddenly this great feeling washed all over me. Later I learned I was having orgasms but I dint know at the time. I found i could make it happen by pulling myself up on doors or on bathroom stalls or almost anywhere I could do pullups. I was 12 or 13 and was doing it at camp one day and I felt something come out, I looked down and there was a stain on my bathing suit. Later on I talked to the guys in our cabin about it and they said sure you can make that happen just by rubbing it.
I went home that summer and tried it and then basically never came out of the bathroom. I masturbated 3, sometimes 4 times a day. Most of the time I looked at JC Penny and Sears underweear ads. (Well except when I was masturbating at school, or in peoples bathroom when my parents visited friends, or basically anywhere I could bew alone for 5 minutes.) And maybe thats wear I got this from. The first year or so of masturbating was almost always all to womens underwear ads…. Until i found my moms underwer drawer.
I knew a little about crossdressing, I mean from MASH and I was constantly looking for anything to do with sex... teachers, underwear ads, articles in women's mags. I knew more about sex I think than some at my age because I'd read anything I could find about sex. Words jumped out at me from books or magazines like they were flashing in red and buzzing. I'd flip through my moms books, I'd go to book stores and buy the horror books with the most sex in them, id go to the library and read stuff about sex there. Then I found my parents’ “Everything You Ever Wanted To Know About Sex,” so I knew people got turned on by it, but it never occured to me until I saw all the silky lacy feminine, sexy underwear. And my mom would put her empty perfume bottles in her underwear drawer so as soon as I opened the drawer they smelled of her when she was all dressed up and done up to go out.
As I went through her drawers my penis began to swell slightly. All kinds of colors, pastels, pinks and blues and purples, and sexy black things and passionate scarlet reds and girlie flower patterns and thin, soft, light silks and shiny satins, feminine lace, slips and lingerie, girdles, and bras, but most of all, panties,. (though the girdles and corsettes held a deep fascination for me too). She grew up in the fifties so there weren't any G-strings or many bikini underwear but it was still panties and womens underwear.
i took a pair out and it poured like water as it slid through my fingers so slippery and silky. It was shiny with flower paterns and lace along the waist and legs. I could smell her perfume slightly on it. I held it to my nose and took a deep breath and literally swooned a little. I almsot passed out, it was almost as if a mini-orgasm washed over me. I rubbed it against my face, knowing it had been so very close to a real pussy. (at the time I tried to put out of my head it was my moms, that truly grossed me out at the time). The feeling of two pieces of the panties sliding against each other as I rubbed it on my cheek, was just incredible, my penis suddenly surged, it almost startled me, my own reaction.
FInally I inspected the cotton crotch. A real life vagina had been pushed up against that for hours at a time for weeks or even months. I could nt take it anymore and pulled my pants down, sat on my moms bed and started plaing with the head of my penis as I continued worshipping my first pair of panties. When I thought about it I tried not to think of my mom's but about the girls in my class and the hot teachers and the girlfriends I had had until then. (If you could call them that, I mean all we did was kiss and I think I had only French kissed just recently.) but like the pervasive smell of my moms perfume the idea of this being my moms underwear and next to her body was always in the back of my mind. By now my head was wet wtih pre-cum and I started stoking the head as i stroked the crotch of the pantis as if I were stroking a real vagina, imagining the ones I had seen in my dads magazines. And then I noticed somehitng, I didnt notice it before becasue this pair of panties were blue and the crotch was a dark blue but there was… A STAIN! I could see where it had been wet once! I had heard about that in the forum section of penthouse! AND THERE IT WAS! Touching the real evidence of a vagina pushed me over the top and I came in the tissue I had put to the side for just that.
And when one of the best orgasms I had ever had in my young life began to subside and I regained some of my senses, a wave of shame and guilt washed over me. These are my MOMS! EWWWWWWW! I immediately put them away and cleaned up and washed, but the smell of her perfume was with me the rest of the day….
to be continued....