I had crossed the Rubicon. I had tried on my sister's panties for the first time. Now I felt guilty. Incredibly guilty, and dirty.
I went to school as normal the next day, but despite the guilt I couldn't get the amazing thrill of trying on that little pair of blue and white striped cotton panties out of my head.
As 3.30pm and with it the school bell neared, the overwhelming urge to do it again overcame my guilt. I was ready and willing to try on my sister's panties once more, as soon as possible in fact.
The young Geography teacher, Mr. Jenkins, who took our class registration, had threatened me with 30 minutes detention for "forgetting" to turn up to have my name recorded the previous afternoon. Luckily he must have decided he wanted to get away early himself, and so after registration I was told I could go straight home. If you are reading this Mr. Jenkins, thank you for that, and I hope you enjoy the story!
I rushed out, and in a pattern that was to repeat itself over and over again in the next few years, I managed to avoid my friends and ran home as quickly as possible.
Back home I went straight to my sister's bedroom, and got undressed. I was going to wear the blue and white pair again, but just as I was going to pick them up I saw another pair on the floor, matching green and white striped panties, obviously they had come together in a pack.
With shaking hands I picked them up and arranged them so that they weren't bunched up any more, and the leg holes were ready for me to step into. I noticed, like the day before, that there was a small yellow-green stain on the crotch. Through impulse I held it to my nose to smell it. Although a part of me was feeling disgusted with myself, I liked the smell, it wasn't very strong, and mostly smelled of slightly stale pee.
But that wasn't why I was here, my whole body was aching to try on another pair of panties. I was again panting like a bitch in heat. I pulled the little green and white panties up my legs until they sat round my hips, cradling my balls and my buttocks. I had the same amazingly intense feeling as the day before, bolts of pure sexual pleasure were coursing through my body.
Although I tried to hold off and spend some time admiring myself in the full-length mirror, I simply couldn't wait. I yanked my cock out through the left leg-hole of the panties and started to masturbate. Again that incredible feeling, and within just 4 to 5 strokes I had come. And what a come, nearly as good as the day before, an absolutely mind-blowing, blinding orgasm.
Afterwards there was more guilt though, which I tried to stave off by telling myself that this was just a passing phase, and that I could stop any time that I wanted to.
For the next few months though, a very familiar pattern developed. I would rush back home from school so that I got there well before my sister, go into her room, try on a pair of her panties, and masturbate.
In that few months I must have tried on every pair of panties that she had. The thrill was still overpowering, maybe not as intense as the first 2 times I wore the panties, but enough to drive me wild and half-mad with lust and make my rampant erect cock as hard as a rod of iron.
One particular pair of panties I remember was a skimpy lace trimmed satin pair with a checked pattern. The feel of the slinky nylon material round my cock, balls and buttocks sent my head spinning, I felt so jealous that girls could get to wear such sexy pretty underwear whenever they wanted. They became a favourite pair, I would even fish them out of my sister's underwear drawer if they were clean and unworn.
The thrill, although still immense, did wear off a bit though. One day I was thinking that it was somehow not quite as good as at the beginning, when an idea came into my head. What would it be like to wear a pair of tights? (i.e. pantyhose in American English)
This thought struck me just as I was about to try on the panties I had selected. On the floor were a pair of tan coloured nylon tights. Right away I was shaking like a leaf again, gasping for breath, my legs almost giving way, hardly able to pick them up because of my trembling hands.
I pulled on the panties, then with some difficulty, being a novice, I managed to get the tights up my legs and round my waist. The feeling was fantastic, my legs were incased in sheer nylon, and by God it felt sexy. I pulled the tights down under my balls, freed my cock from the panties and frantically wanked myself off in less than 10 hasty strokes.
What an orgasm, I couldn't move afterwards! I lay on the floor exhausted, my cock still pulsing with pleasure. The sound of a key in the house door startled me into action, I somehow managed to tear off the tights and panties and get my own clothes on, before my sister could catch me.
Nearly caught! What would she have said if she had seen me? A lucky escape. But... somehow the idea of getting caught dressed up like a pervert turned me on, I almost wished it had happened. From then on tights became a regular part of my daily crossdressing experience, especially sheer black nylons, which looked and felt so good on my smooth hairless legs.
The next escalation was that one day I decided to try on my sister's bra. Although exciting that wasn't such a great success though, it was way too small, and although I managed to get it on eventually, it was stretched so tight that it hurt, and I was frightened it would rip.
All this time there was one problem in the background - guilt was gnawing away at me. Despite all the fun I was having and the great excitement that wearing my sister's underwear generated, I wanted to stop doing it. And to my own surprise, from somewhere I found the willpower to do it. I stopped, forever as I thought then, although that was not to be.
I stopped for 3 months, but if truth be told, it was never out of my head. I would masturbate at least 4-5 times a night in bed, thinking of wearing panties again.
3 months later when I finally did succumb to temptation again, it came from an unexpected source. My mother was a very attractive woman. Tall and sexy, she had a tremendous figure and wore very feminine clothes.
With my teenage hormones going crazy, I shocked myself one night in bed by fantasising about having sex with her while I was masturbating. This to me was far worse than the wearing panties, I felt awful, I was a sick filthy pervert.
I couldn't stop myself though, and the fantasies got more and more intimate. I had learned from a sex manual we had on one of the bookshelves in the house, how a man could bring a woman to orgasm by giving her cunnilingus, and also how many women actually preferred this to intercourse, and could orgasm more easily.
I began to fantasise about licking my own mother's cunt. This perversion made me feel sick, but I couldn't ward it off. I began to wonder what she would taste like, and how she would smell between her legs. Of course little girls are often told how dirty and smelly they are down there, which in itself was intriguing for me.
One afternoon at home, when my sister had gone out with some friends, I was thinking about that little yellow-green stain that my sister often had on the crotch of her panties.
Then I was hit by another bolt from the blue - what would my mother's panties smell like? Then the idea came - why not sneak into her room, and sniff the crotch of her used panties?
Every new perverted idea seemed to drive me back up to the peak of sexual excitement, and once again I was panting uncontrollably, my legs were shaking, my stomach was doing somersaults, and a raging erection sprang up instantly in my underpants.
I just couldn't resist the urge, I got up out of my chair and sneaked into my mother's bedroom. It took a while to work out where she kept her used clothes, unlike my sister she didn't simply throw them on the floor. Finally I found them. The panties, bras and tights were placed in a large plastic bag in the bottom of her wardrobe. The other used clothes like dresses, skirts and blouses were also in the bottom of the wardrobe, but left there in a loose pile.
I gingerly pulled a pair of my mother's used panties out of the plastic bag. The contrast with my sister's panties was striking. They were a bigger size, and much sexier and more feminine. Made of white satin they were more lacy, and although a bigger size than my sister's much skimpier, with a high waistband but with the legs cut away at the sides so that the hips and the lower part of the buttocks would be on display when worn.
I untangled the panties and gasped audibly at what I saw. A long thick smear of green discharge ran the length of the crotch. In fact longer than the crotch, it extended right into the front of the panties themselves.
The thought "Oh my God, I really shouldn't be doing this" raced through my head. But I was doing it, I just couldn't help myself. "This is sick" I thought to myself, "violating my mother's inner sanctum and taking liberties with her used panties". But my trembling, shaking hand moved upwards, and I held the crotch up to my nose.
What an incredible smell! Rich, pungent, the aroma filled my senses and waves of sexual pleasure ran through my body. So much stronger than the smell of my sister's panties, so sexy, what a turn on!
The inevitable happened, I just had to masturbate, my aching cock and my shaking, excited body demanded it. With the smelly panties still pressed to my nose I whipped out my cock with my other hand. Just as when I had previously tried out one of my perverted ideas for a first time, the orgasm was quick and unbelievably intense. About just 5 or 6 strokes of my rampant cock and a stupendous orgasm hit me, and more spunk than I had ever produced before squirted out of my twitching cock and onto the carpet.
I put the panties back, closed the wardrobe door, and feeling very ashamed of myself sneaked back out of the bedroom. "Never again!" I told myself, thinking I had crossed some sort of line in the sand that was so taboo that I had no choice but to stop. But just 30 minutes later, I was standing there again in front of my mother's wardrobe, my erect penis in one hand, a pair of her dirty used panties in another.
This time the panties were black, lacy and frilly, cut low at the waist and with a relatively narrow crotch compared to the white pair. Again the crotch was decorated with a long smear of dried up cunt discharge. I breathed in the strong penetrating scent and wanked myself off frantically to another amazing orgasm.
I lay awake that night in bed feeling very guilty, but not so guilty that I didn't have my cock in my hand masturbating. Then the inevitable happened. "What would it be like to try on my mother's panties" I thought? Despite an immediate feeling of revulsion at my disgusting thoughts, my cock was instantly rock hard and I was wanking myself stupid under the covers.
The next day at school followed a familiar pattern. All day long I told myself how terrible the idea was, and convinced myself that I would never do it. But as soon as school was finished, I was running home as fast as my legs could carry me, my body aflame with the idea of following through my filthy fantasy.
As soon as I got in I ran to my mother's bedroom and found a pair of her used white cotton panties, lacy ones. I was shaking uncontrollably again because of what I was about to do. I held the crotch to my nose and breathed in that sexy, dirty smell. Heavenly! And then I tried them on.
The feeling was wonderful, so soft, so sexy. I looked at myself in her full length mirror and admired her sexy panties. Not for long though, the urge to masturbate was so strong that I was soon playing with my rock-hard cock, so excited that I came again in no more than 10 strokes, and my teenage body was consumed by a glorious shuddering orgasm.
Again I felt guilty afterwards, but within 10 minutes I was back in her bedroom again, wearing the same panties and frantically wanking myself off. Then again after 5 minutes of guilt I was back, this time with a different pair of lacy white panties! It just felt so good, so sexy, so dirty. I don't think I ever tried on anything of my sister's for years after that, the feeling of wearing my mother's clothes was overwhelmingly more sexy and fulfilling.
The weeks and months that followed saw me get more and more addicted to wearing my mothers clothes. I tried on all kinds of her dirty panties. Then I tried wearing her tights (pantyhose). Amazing! They fitted me far better than my sister's, and felt so good on my legs. Then I started trying on her bras. Again the feeling was fantastic, and they fitted too!
Now almost every schoolday I would rush home, try on a bra, panties and tights, and wank myself off in front of my mother's mirror.
One day I wondered what her panties would taste like. I licked the long thick smear of yellow green cunt discharge on the crotch, marvelling at the fantastic taste as the dried up juices moistened and came to life again. I tried the same panties on, and thrilled at the feeling of the moist smear where her cunt had been, now clinging to the base of my cock and balls. This is how it must feel for a woman I thought, and before even putting on the bra and tights I'd got ready, I had an uncontrollable urge to wank myself off to yet another amazing orgasm.
The next escalation came quickly. As I rushed home one day, I saw a very sexy woman at a bus stop, in a red skirt and matching jacket, with a white blouse, tan stockings, and black hi-heels. The sexy secretary look. Wow I thought, she's so pretty, and so lucky to be able to wear clothes like that.
Then as I neared home I remembered my mother was also a secretary. She also had sexy clothes like that in her wardrobe! I rushed into her room, and selected a matching white lacy bra and panty set, tan tights, a white blouse, and a black knee-length skirt. I was so excited I could hardly breath. I so wanted to try on that skirt, but I knew I had to get everything else on first.
I got into the bra, panties and nylons, then buttoned up the blouse. It felt good, so much softer and more feminine against my skin than the coarse shirts I wore to school. I liked the way the buttons were on the other side too, it just felt right. Now I was ready for the skirt.
After a bit of fumbling with my shaking hands, I managed to get the skirt ready to step into. I was trying on a skirt for the first time, how exciting! I stepped into it and pulled it up round my waist. It felt fabulous! Then I zipped it up the back. I looked in the mirror. I was a woman!
The skirt felt great swishing against my nylon clad legs as I paraded in front of the mirror. Then I saw a pair of my mother's black patent high heels. It was a tight fit as I was 2 shoe sizes bigger than her, but after a struggle I managed to squeeze them on. I looked in the mirror again, what I saw made me feel soooo sexy and soooo dirty. The feeling was so good that before long I'd hiked the skirt up round my waist, pulled the tights and panties down under my cock and balls, and masturbated my self to an incredibly fulfilling, almost spiritual orgasm.
I the weeks that followed I tried on all sorts of underwear, dresses and skirts, and squeezed myself into various sexy women's shoes, and naturally almost wanked myself into a coma.
The risk of getting caught by my sister was now much higher, as it took longer to get the clothes on and off again. One day my sister came home early, just as I had hiked my skirt up to start to masturbate. As soon as I heard the key in the door I ripped the clothes off as quickly as I could. There was no time to waste, my sister was coming along the hallway! I shoved the clothes out of initial sight under the bed and frantically pulled on my underpants.
She opened the bedroom door to find me standing in the middle off the room in only my underpants, trying to hide my still bulging unfulfilled cock, flushed and breathing heavily, my mother's wardrobe door still wide open. "What are you doing?" she said. I mumbled something incoherent, and started putting on the rest of my clothes. Nothing was said afterwards, but I always wondered if she had guessed what I was up to.
Although I was having a fantastic time and treating myself to loads and loads of amazing orgasms, one thing that never went away was the guilt. In fact it began to get stronger and stronger. I thought I could never stop raiding my mother's wardrobe, so it was to my amazement the guilt eventually got so strong that from somewhere I found the willpower give up.
In fact I gave up for nearly a year. I thought I'd put it all behind me. But little did I know, that one hot summer's day in the future I would start crossdressing again with a vengeance, with the realisation that I would never be able to give it up.
It was a Saturday in August during the school holidays and the weather was very hot. I was at home alone, my sister had gone out with some friends. My mother had been out too, but had just arrived back. She was wearing a beautiful just-above-the-knee pale blue summer dress, with a yellow flower pattern round bottom of the skirt of the dress and also around the top of the dress where her breasts lay. The material was thin cotton, and it was shoulderless, held up only by shoestring straps. She was also wearing a pair of pale blue strappy hi-heel sandals. She looked great, fantastically sexy.
My mother kept on saying how tired she was, and how it was so hot that she was feeling very sticky and sweaty. Then she announced she would have a bath. She started the bath running, then went into her bedroom to get undressed. She emerged in a dressing gown, and came and chatted to me for a while until the bath was ready.
After she'd gone into the bathroom and pulled the door shut behind her, I started thinking about how pretty and sexy she looked in her dress. "What a beautiful dress" I thought, "she looked fantastic". I hadn't dressed up now in women's clothing for 9 or 10 months, but suddenly the old urge came back stronger than ever, and with a twist - why not wear the clothes she had just been wearing?
My heart started hammering at the thought of doing something so daring and dirty, and a delicious thrill shot through my cock. "But she's just lying there in the bath" I thought to myself, "what if I get caught, what if she gets out of the bath unexpectedly?" This was unlikely though, my mother took long hot baths, and from out of the bathroom I could hear the water sloshing around as she luxuriated in the warm water. I knew I was breaking a vow I'd made to myself never to cross-dress again, but I just couldn't stop myself.
Trembling I very quietly tiptoed into her bedroom, which actually had an adjoining wall to the bathroom. I would have to be quiet! I saw that she'd taken off her clothes and hung them over a chair in front of her dressing table. Without hesitation and in a state of hyper excitement I ripped my clothes off as quickly as I could, my raging erection pointing to the ceiling as I released it from my underpants.
I was so incredibly excited, I had never done anything as naughty as this before, dressing up in the clothes my mother had just been wearing, while she lay naked in the bathtub just behind the bedroom wall.
First of all I put on her panties. They were white lacy cotton ones, all rolled up from the way she had peeled them off of her sweaty body. I unrolled them, stepped into them, then pulled them up over my ankles, my calves, up my thighs, and finally up over my balls and round my bum and waist. I could barely suppress a gasp as the still fresh and moist slick of cunt discharge on the crotch made contact with the underside of my cock. It was the first time I had experienced the real moisture of a panty crotch without licking it to make it wet first. The feeling of that wet crotch clinging to my cock and balls was indescribable.
Then it was time for the bra, a white strapless one. I put my arms in then clasped it together behind my back, then stopped quickly to admire myself in the mirror. It felt so sexy to see myself there, naked except for a strapless bra and panties, with my erect penis sticking proudly out of the top of the panties.
Then it was the dress. Because the material of the dress was so thin, almost see-through, she had been wearing a white satin underskirt with lace trim. I pulled it on, marvelling at the silky feel of the material against my legs.
And then the dress proper. The zip at the back was right down as far as it would go, so I held it in my hands by the thin shoulder straps and stepped into it. A bit of adjusting of the underskirt and I was able to pull it up over my legs and hips and right up to my chest, and with shaking hands pull the straps up over my arms, and onto my shoulders. I put my hands behind my back and managed to pull the zip right up to the top of the dress. It looked so good in the mirror, and it felt so good on my body.
Next the hi-heeled sandals. I had to sit down on the chair for this. They were as ever 2 sizes too small for me, but being strappy sandals with an elasticated ankle strap I was able to get them on fairly easily.
I stood up, dressed completely in the clothes my mother had been wearing, and looked in the mirror. An enormous feeling of sexual pleasure swept over me. The feel of the still-moist crotch of the panties clinging to me, the beautiful dress against my body, the sexy strappy hi-heels I was balancing on, all combined to send me over the edge.
I pulled up the skirt and underskirt, pulled the left hand leg of the panties over my cock so that my cock sprung free, pressed the moist crotch of the panties hard against the base of my cock with my right hand, and started to masturbate with my left.
I was so excited, but this time it wasn't just a mad frantic wank until I came, I enjoyed and savoured every second of it. The moist panties, the feel of the dress, the way the high heels made my calf muscles tighter and pushed my buttocks up making them perkier. It was a glorious feeling, wave after wave of pleasure mounted over me as my orgasm neared. It was pure guilt-free pleasure, everything about this was so right, something that felt so gloriously good couldn't possibly be wrong.
Then I came, a wonderful, sustained, fulfilling orgasm, and more sperm than my young body had ever produced before shot out of my cock, in 6 or 7 jets of warm, creamy white spunk. It wasn't the strongest, most exciting orgasm I'd ever had, that was when I first started trying on my sister's panties. But this was beautiful, spiritual, and when it finished my knees were so weak that I had to sit down straight away.
Now worried about being caught I quickly undressed and put the clothes back as close to the way I had found them as I could remember. But as I undressed and put on my own clothes again there were no feelings of guilt like before. I felt happy, I was glowing, the whole experience had been so wonderful.
And that's when I realised, that I would never be able to stop dressing up in women's clothes! I enjoyed it so much, it made me feel so good, it was an addiction stronger than heroin for me. No matter if later I felt guilty again and gave up for a short time, or even for a long time - I would always come back to it, it would always define me sexually, and I would always love doing it.
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/teenage-cd-awakening-part-ii.aspx">Teenage CD Awakening Part II</a>