I’m not exactly sure how it all started but I sort of remember watching tv and seeing dancers dressed in nylons and tight fitting outfits and something stirred in me. No idea how old I was at the time. 

Sometime later I remember reading my brother’s Mad Magazine and this one cartoon is vividly etched in my memory banks. It showed a pair of tights or pantyhose that were “one size fits all.” It then showed what that term meant by first showing them on a baby and they looked like solid tights - and it said so-so fit. The next image was the tights on a young girl and the tights looked slightly sheer and looked good - and it said a slightly better fit. Next image was a teenage girl and the tights were more sheer - and it said an even better fit. The last image was of a shapely woman and the tights were revealed to be fishnet and looked marvelous on her - and it said perfect fit. 

I think every boy would have been excited by the cartoon. It inflamed me, not with the notion of seeing them on some women, but of wearing them. Wearing them and being seen by a man who would think I looked sexy in them.

After that it was rummaging around in my mother’s panty drawer and rubbing my stiffening cock. I don’t remember if I came at the time but I clearly had some sort of mental orgasm.

The final straw was in sixth grade when I was in the Christmas play. I was one of Santa’s elves. I was the only elf with a speaking part - they gave me all of the lines that were supposed to be said by different elves because I was perhaps the smartest kid in class and I easily memorized it all. But the best thing about being an elf was that I got to wear black tights. I loved those tights. I kept them afterwards and wore them when I was home alone and masturbated with them. If I was home alone at night, I’d slip out into the yard while wearing the tights. It was thrilling with the risk of being caught wearing them sweetening the whole experience. They sort of sealed my fate.

When I was older and looked at the pictures in Playboy and Penthouse, it wasn’t the women that turned me on, it was the nylons, lingerie, panties, and high heels that they wore that got me excited. Fantasies of wearing those things and making love to some man (although I didn’t really know what that meant) filled my head. 

So, for most of my life I was a secret crossdresser. When I was alone I’d wear panties, pantyhose, etc. and masturbate. In college I stole someone’s panties from the laundry room. I was a resident assistant in the dorms and had to stay until the bitter end, the day of graduation. I remember pulling out clothing and pantyhose that women threw away as they left the dorm. Over the years I bought pantyhose and other things and secreted them away to use to satisfy myself. The fantasies about crossdressing and having sex with men got more detailed and explicit but were never acted upon. The times I was home alone or traveling on business were my times to play.

I always felt conflicted about this. I love wearing these things but felt like I was a total degenerate pervert. When I felt especially ashamed or guilty, I would throw away all of the lingerie, etc. that I owned. And then weeks or months later I regretted having disposed of everything and started obtaining new things to wear. It was always hard or impossible to admit and act upon being a crossdresser. I believe that this is why so many men have this fantasy of being discovered, of being threatened with having their secret revealed so agreeing to suck cock, of pictures being taken of them dressed in lingerie so that to protect the secret they agree to be fucked and to be used by friends of the blackmailer, and on and on. The fantasy is about not being in control. It’s about being able to tell yourself that you’re still just a normal guy and that you have no choice but to dress and be a sissy cum slut.

It never dawned on me how common the panty-wearing or crossdressing fetish is. It never dawned on me that there were men who didn’t want to crossdress but wanted to have sex with men who did. So late in life I feel regret that I didn’t understand what I was. Regretted that I didn’t recognize that there were men who wanted me. Regretted that I wasn’t brave to admit to myself and to others that I was a sissy. And regretted that when I was not caught crossdressing and gently blackmailed into being an openly crossdressing sissy cocksucker and fuck toy.