I haven't always been a crossdresser, when I was very young (about 9 is the earliest) I remember being fascinated by women's legs in nylon stockings (they still wore stockings in those days). I remember being at a friends house, and his mom used to put her son over her lap and rub his back with a soft brush as form of reward, it was like a soft back-scratch if u like. One day she asked me if I would like a 'rubbing' and of course I said yes. She always wore skirts just above her knee and I noticed she always wore sheer fully-fashioned nylons (of course I was too young to know what FF nylons were). She put me over her knee and rubbed my back which was nice, but better was the feeling of my bare legs (I was in shorts) against her slinky nylons. That was the first time ever I remember getting an erection. I don't think she noticed my little stiffy, but I knew then that I was fascinated by not only the touch but also the feel of nylons.
By the time I was in my teens I had a full-blown nylon fetish, by now women were wearing pantyhose instead of stockings but I still loved nylon encased legs. I had quite a collection of nylons most of which I got when Mom or my sister discarded theirs; I would wait until no one noticed then take them out of the bin. I was also wearing nylons a lot when no one was around or I was in bed and masturbated while wearing a pair of pantyhose and then placing a nylon on my cock. One of my favourite pastimes was visiting my Aunt Mary, she was a single mom who lived alone with two daughters, and they all wore pantyhose. While my sister was playing with the two girls I would rummage in their bins for discarded hose and rifle their laundry basket. Then one day I got caught.
I was 15 and Abegail, my eldest cousin was 18, and she was the one that caught me. The three girls had supposedly gone shopping with Aunt Mary, leaving me to my carnal pantyhose pleasures while they were gone. What I didn't know was that Abby had left the others to return home, feigning a stomach upset. But I found out later that she suspected I was tampering with her lingerie and she intended to catch me. She told me later that she had noticed stains on her pantyhose when she washed them and as she was 18 and sexually active, she had good idea what those stains were. I was by this time, oblivious to the world, hiding in their bathroom wearing a pair of sheer pantyhose and stroking myself through the sheer nylon gusset. Abegail burst through the door and shouted "I knew it, you pervert, I knew you were wanking in my lingerie, you fucking little pervert". I was so scared and embarrassed; here I was standing in her bathroom wearing nothing but a pair of her pantyhose and a hard-on, which by now was quickly deflating. I lost control of my legs and sat down heavily on the toilet seat.
"You fucking Nancy boy" she said, "wait until I tell your mom, my mom, your sister, every fucking one that you're a Nancy-boy, pantyhose wearing, pervert!" I was so scared and started begging her, "please Abby, don't tell anyone, I'll do anything you say, I'll stop doing this, I promise!" I was a pathetic sight standing in front of her naked, grovelling to her. She was standing over me fully dressed, she was wearing a cute little purple mini-skirt, white blouse and platform heels (this was the 70s remember) and of course, beige pantyhose (beige and white were the mainstay of 70s hosiery). "You bet you'll do anything ‘pantyboy'" she said, "You'll do whatever I fucking well say or everyone will know about your little pantyhose perversion!" By now the initial shock had worn off and couldn't help noticing her legs showing nicely below her mini, she had one foot forward and her hands on her hips in a dominating pose, she was a little chubby but had nice legs and a pretty face. Of course her standing like that with her silken hose covered legs at eye level had an obvious effect on my penis. Abby had never particularly liked me and had teased me a lot when I was younger, her being three years older she was always dominant, now she noticed my gradually stiffening penis. "You fucking freak, you can't help yourself can you" she said pointing at my nylon-covered appendage, "well now that horrible thing is sticking out, you humiliation starts now pantyboy". "Stand up pantyboy" she said, "lets see what that pathetic little dicky looks like". I knew Abby had had a few boyfriends and guessed she was no stranger to male anatomy, and I definitely knew she was certainly not going to miss the chance to humiliate as much as she could, but standing there, her tight sheer pantyhose encasing my lower body, and her being fully dressed somehow excited me.
I stood up and my now erect penis was pushing out the gusset of the hose, there was a small pool of clear pre-come forming at the end of my penis and soaking into the nylon. "Well you are the panty-boy, aren't you, now I know why those stains were appearing my pantyhose every time you visited, you disgusting little pervert. Go on, show me what you do when your wearing my nylons." I stammered, "what do you mean" "You know what I mean pantyboy, wank that disgusting little cock!" She started to laugh as I took my cock in my hand and started to stroke it through the nylon, "you really are pathetic you know" she said, "I'll bet you've never even been with a girl before have you!" "No" I answered looking down at my pathetic nylon covered toes, tears were starting to form in my eyes and I didn't want her to see me cry. She stepped forward and lifted my chin, "stop that you pathetic pantyboy, I don't want you simmering away, now stroke that fucking cock! Show me what you do in my hose or the whole world will know!"
I put everything else out of my mind and just stared at the little purple mini and her thighs below the hem. I started to stroke my hosed member again. It started to feel nice and I could feel really myself engorge at the thrill of what I was doing, wanking off in front of Abby. I have to admit it was a fantasy I had had previously when I masturbated while wearing her pantyhose. I stroked it faster, rubbing the sleek nylon gusset against my turgid member and staring at her legs, imagining my cock rubbing against them. "You fucking pervert!" she hissed, "your really enjoying that aren't you! Well I'll put a stop to that!" She reached out and slapped my hand away from my cock. "Leave it alone pantyboy" she said, I looked down again at my toes, humiliated again. "Don't look down, look at me! And leave that alone!" she said pointing to my hard cock poking out the front of her pantyhose. Its disgusting she said and all of a sudden reached out and grabbed it to make her point. It was too much, I was close to coming before, but the feel of a girl's hand holding my cock while it was encased in sheer nylon was a sensory overload. I shuddered and groaned as I spent my seed. The ejaculation pulsed out of my throbbing penis and poured through the nylon gusset into Abby's hand.
Abbey of course was disgusted and wiped her hand on my body, covering me with my own semen. "Now fuck off out of here pantyboy," she said, "and never touch my underwear ever again". I heard her mocking laughter as I ran down the hall the bedroom in which I was staying. To say I was terrified was an understatement; I was so scared she would tell everyone about my perversion. Days, then weeks passed and nothing happened. Whenever I met Abbey she would snigger at me but never bought up the day she caught me. I wondered why she had the ultimate degradation to inflict on me but didn't. Then it dawned on me, she was older that me, she had humiliated me, she should have known better and more importantly, what she did to me was wrong.
It was then I hatched my plan. Next time we visited Aunt Mary, I confronted Abbey in her bedroom "what do you want pantyboy" she sneered. I told her what I had been thinking about what happened "well what the fuck you going to do about it pantyboy, you can't tell anyone otherwise they will know you are a pervert". I was really angry now and answered "I am going to tell mom, she wont care about what I was doing, just what you did to me, your older and should know better, she will tell your mom for sure!" I could see she was starting to sweat, her bluff had been called. "Please don't tell" she said, "I'm sorry, I take back what I did." Not good enough I said as my plan formulated further in my mind. "You have to be punished for humiliating me," I said. "Whhhhhhhhhat do u mean" Abbey looked flabbergasted. "You have to make it up to me" I said, "or I just leave right now and tell mom and Aunt Mary what happened!" "Ok, ok, ok" she said cutting me off as I headed for the door, she closed the door and locked it. "What do you want from me" she asked. "Well' I said, "I know that you have had boy friends so I figure you must know all about sex." She looked shocked "so!" she said. "Well now your going to let me do some things to you that you have probably done before anyway, so you shouldn't mind" I grinned evilly at her. "No fucking way!" she exclaimed. "Ok then" I said and started to unlock the door. "Alright!" she sighed disgustedly. "Sit on the bed and don't say another word" I said, "now its time for to pay". She sat demurely on the edge of the bed. She was wearing another A-line mini, white this time, a pink blouse, platform shoes, and of course, my favourite beige pantyhose. I sat down beside her and placed my hand on her knee, the nylon felt silky against my fingers and immediately began to stiffen. I stroked her leg up and down from the top of her thigh to her ankle. She just sat there and stared up at the ceiling, enduring my molestation. She stiffened as I my hand went under her skirt and rested on her silky nylon panties. They were full cut sheer white nylon. Her hand went on mine and tried to push me away, "Mom" I yelled, but not loud enough for anyone outside the room to hear. She understood the threat and took her hand away. Now I stroked her through her panties, feeling the nylon of the panties rubbing on the nylon of her pantyhose gusset was making me extremely aroused. I noticed her breathing was deeper and quicker and her eyes were closed. I eased my hand down to my shorts and freed my erect member. I leaned over and began to rub it on her pantyhosed leg as I continued to stroke her panties. We were now both breathing deeply and heavily and I could feel her panties becoming moist to my touch. I was so excited, the first time I touched a girl there and she was enjoying it, even if she was being forced to do so. I gently pushed her back on the bed and climbed over her, she whimpered "nhhoo", but her heart wasn't in it. I pushed her skirt up to her waist and lay on top of her. My throbbing penis was pushing against the nylon of her panties and as I began to grind it back and forth, I felt it rubbing against her panty and pantyhose covered pussy. Amazingly she began to push back against me, matching my thrusts with her own. I put my hand down and moved her panty crotch to one side and tried to push my member through the hose; "NO, NO, NO, NO!" she whispered in my ear, "you cant do that, you can't fuck me". She reached down and placed my penis in the folds of her pussy, but still protected by the sheer nylon of her pantyhose, then she eased the silky gusset of her panties over the top of my penis. It was exquisite, my penis in a nylon trap, the sheer hose covering her pussy was pushing against the base of my penis and the silky gusset of her panties was pushing against the top of it as we thrust against each other. We ground against each other, panting and sighing, but I felt myself ready to come. She felt it as well and wrapped her nylon-encased legs around me and held me to her as she pushed her silky gusseted pussy against my penis. Then she kissed me thrusting her tongue deeply inside my mouth as I exploded against my cousin. I could feel my semen saturating her pantyhosed pussy and legs and soaking her panties. She was pushing against me so hard and she groaned "Goooooooooooodddd" into my mouth as she was kissing me and shuddering with her own orgasm.
I enjoyed Abbey's pleasure many times over the next few months; she always kept her pantyhose on to prevent me from entering her. She explained that, as I wasn't actually fucking her, in her mind, we were not really breaking a family taboo. We were exploring new ways to pleasure ourselves, she knew I loved the feel of nylon against my cock because she had caught me wearing her pantyhose. So it did not take long before I was wearing her pantyhose during our ‘sessions'. One day she had me wear a pair of her nylon panties over sheer to the waist pantyhose whilst she was dressed the same. The feeling of our highly aroused sexual organs rubbing together encased in folds of nylon from the panties, straining against the sheer nylon gussets of the pantyhose was wondrous.
But then as suddenly as our sexual encounters started they came to a screaming halt. It did not take too long for 18 year old Abegail to acquire a new boyfriend, a new jealous boyfriend. Besides the fact that she now hardly had any spare time at all when I visited, she explained to me that if we continued what we were doing she would be cheating on him. Also she said she believed what we doing was very close to incest; she could not continue our sessions any longer but had enjoyed what we had done in the past. She asked me not to be jealous of her boyfriend but to remember fondly our lovely encounters. Abbey gave me two pairs of her pantyhose and a pair of her sheerest panties as a ‘farewell present'.
My passion for nylons and nylon panties continued on through my teens and into my twenties. I still wore pantyhose and whenever possible nylon panties to bed and to masturbate. I liked to wrap a sheer stocking around my cock whenever I wanked. I managed to get myself girlfriends, (always girls that wore pantyhose often), lose my virginity, and on the odd occasion find a girl that would share my nylon fetish. A couple of my girlfriends let me fuck them while they still wore their stockings or pantyhose and one girlfriend I had when I was 25 would let me wear pantyhose as well.
One afternoon my girlfriend Eileen and I were in the bedroom of my flat lying on the bed. I had my hand under her skirt, stroking her pantyhosed thighs. My hand would wonder across her crotch, pushing against her nylon encased mound; she was moaning and pushing against my hand. "That feels so good" she whispered. "I know" I said, "I just love the feel of nylon against me too". She giggled, "go on then – get dressed, I know you want too". I quickly discarded my clothes and slipped on a pair of sheer pantyhose. Eileen was hip to my fetish by now and we had often fucked whilst both wearing hose. Her hand slipped up my nylon legs and lightly caressed my balls. I was in heaven as I maintained my pressure on her silken clad mound. I pushed her back on the bed; she looked magnificent, fully clothed with her red miniskirt hiked up around her waist, sheer taupe pantyhose, white nylon panties, and red high heels. I climbed on her and ground my hard member against her mound. My cock and balls encased in the fabric of my pantyhose was rubbing against her pussy covered in the sheer nylon of her pantyhose and panties. I reached down and with my fingernail I made a small hole in the front of my pantyhose and let my dick poke through. I now had my cock rubbing and pushing into her pussy. I could feel her outer pussy lips against my cock head through the nylon of her hose and panties. I again reached down and this time made a small hole in the gusset of her pantyhose. "Oh Dear! I ruin more nylons this way" she giggled and wrapped her sheer nyloned legs around by back as my penis pushed aside the fabric of her panties and slid into her. I was so excited and was already close to coming. "You really do love nylons don't you darling" she whispered in my ear as she thrust up against me slowly. "Oh my God yes" I whimpered, on the verge of orgasm. "I have an idea," she said, and to my despair she eased me out of her glistening pussy. "What are you doing" I begged. "I'm so close." Again she giggled and to my surprise she reached over to the bedside table and dipped her hand into the drawer where I kept my pantyhose, stockings, and panties. She drew out a sheer nylon stocking and to my utter amazement and delight, slipped it over my hard penis. She slowly stroked my throbbing member through the nylon of the sheer stocking. "Christ I'm going to come!" I shouted. "Not yet" she whispered into my ear as she slid back under me and positioned my stocking encased member against the entry to her soaking pussy. She then pushed slowly but firmly against me, sliding the nylon covered cock into her cunt. I was in heaven. Her hot wet pussy was gripping my stocking covered cock like a silken glove. At the same time my pantyhosed balls and legs were rubbing against her pantyhosed legs and sheer pantied arse. I couldn't hold it any longer; I exploded deep inside her. Needless to say I married Eileen.