I'm sure most of us remember it in some shape, form or fashion but I remember almost every single detail of mine. The one thing I can't remember about it was my age. I know I was older than 10 so I was either 11 or 12, but I'm not sure which. I know it was a dry orgasm, it was during the summer, it was between one and two in the morning and I was standing in front of the dresser, looking in the mirror in my parents room. I know that sounds like a strange place to have your first orgasm but there is a good explanation for that. You see, my mother was taking her turn working midnight shift at the hospital on base and, since she was doing midnights, my father traded duty with other people so that he was the base Assistant Duty Officer some of the nights she worked. That way, he got his overnight duty out of the way while she was doing the overnights. Now can you think of anything more perfect for a sissy like me who would dress up in his mother's clothes anytime he had the chance? I would usually give them about 15 minutes after they left to make sure they weren't coming back for anything, then I would be out of my bed like a shot and into her lingerie drawers and her closet. Many times I would wear a grayish black skirt with little flecks of blue in it, a blue sweater, stockings, her heels which fit me at that time and of course underwear. Bra stuffed with panties, a pair of panties and long leg girdle. I would ad a scarf and lipstick before going out on the back porch to feel the breeze across my nylon covered legs. This particular night my outfit varied a little. I had managed to avoid a haircut for a while and my hair was slightly long and combed back over my ears. If I let it hang down it looked faintly feminine (at least in my mind it did). This particular night I was wearing the usual white panties with a long leg panty girdle and, at that age, I knew nothing about tucking. But since I really wasn't getting erections, I could let my penis lay flat against my stomach and allow the firm center panel of the girdle to mash it flat (and it did). While I may not have been getting erections, I still knew that rubbing myself through the girdle always felt really good. Anyway, I had raided the closet for the nurses uniform she wore the night before. This was back when nurses uniforms were very heavily starched, had buttons up the front and on each sleeve that were placed in similar to cufflinks. She would hang her worn uniforms back up until she could take the buttons out before sending them to the laundry. The nurses hats were also starched heavily, then folded and buttoned, then held to the hair with hairpins. So there I was, white nylon stockings (about as thick as tights) attached to the garter tabs of the panty girdle with a soft nylon panty underneath. I seem to remember that I was wearing her longline bra with panties stuffing the cups and of course back then a lady always wore a slip. Most of hers were just very plain nylon to wear under her uniforms. And on top of that, her uniform and with my hair barely long enough, I was able to pin one of her nurses caps on. Shoes were my mother's spare pair of white nursing oxfords. Normally the only makeup my mother wore was face powder and lipstick but for some reason she had started wearing a little mascara and some eye shadow not long before that (I think I know why but that's another story). So I was able to use more than just lipstick and powder that night. I'm sure with no practice using shadow and mascara I probably looked terrible but I thought I looked beautiful. Oh and I topped it off with clip-on button style pearl colored earrings. This particular night all along as I was dressing I kept rubbing myself and it felt different somehow, I guess better than normal. After I was finished dressing, I walked around the house, peeked in their room to make sure my brothers were still asleep, went into the kitchen to get something to drink more to see my lipstick marks on the glass than anything else. This was also during the short time that my mother smoked but she only did it in the house, never in public. And yes, I was sneaking her cigarettes when I could but again that night, it seemed more erotic(?) to light up a cigarette and see red lip marks on the filter. Can you imagine how intense a feeling it would be for an 11-12 year old sissy boy to be standing on his back porch, looking like his mother in all her clothes and smoking one of her cigarettes. I went back inside, put the cigarette out in an ashtray that she used and went back into the bedroom. I was standing there in front of the mirror and, as I said, rubbing seemed more pleasurable that night that previously so I rubbed a little more. That was when it happened and I didn't have any idea what was going on. The MOST intense pleasure started through me but I honestly thought something was wrong. I remember being really scared that I was sick or something but couldn't stop rubbing my dick, my vision blurring and my legs collapsing as I went to the floor and everything just exploded. I really think I passed out for a short while because the next thing I was aware of, I was laying on the floor next to my parents bed on my side with the most incredible feeling throughout my body. I could really feel the stockings on my legs, the pressure of the girdle encasing me from my waist almost to my knees, the bra tight around my chest and the taste of lipstick. It was so amazing that I was really sad that I had to put everything away, shower to clean up my face and go to bed. Of course I have cum many times since then while dressed in women's clothing. Being a sissy faggot, I've sucked dicks and/or taken them up my ass while crossdressed and cum while doing it. Nothing, including my first time with a girl, has ever come close to that night and my first time cumming.
Oh, the other story about my mother and the makeup? I now think the guy next door was fucking her. But more about that later.