Teenage CD Awakening Part I

By anotherfeeling

Original link: https://www.lushstories.com/stories/crossdressing/teenage-cd-awakening-part-i.aspx

Tags: Crossdressing, Sister, Panties, First time, Masturbation

Added: 19 May 2011 Views: 33513 Avg Score: 4.56

A tale of a teenage boy’s first overwhelming urge to try on a pair of panties
As a child I lived in a town in the North of England. It was a fairly conservative place, where boys were expected to grow up to be men, and girls to become women. Despite this my mother was a fairly liberal person, and by the time I’d reached the age of 17 the topic of sex had already been raised in our house. Sex between men and women of course, with the aim or perhaps the danger of making babies!

This was in 1979. Although my skinny body was still hairless my interest in sex and my desire to masturbate were growing by the day, much like my height (and despite my lack of pubic hair the size of my cock!).

I had no inkling early that spring of the direction my sexuality was soon to take. I dreamed of the girls at my school in their short navy skirts, sheer black tights and white ankle socks, their bras showing through their tight white blouses, their beautiful long hair held away from their faces with hairclips, or maybe put up in a ponytail. Perhaps my fascination with their clothes should have been a warning of what was to come!

Spring moved on and Easter came, and with it the school holidays. My mother, my 16 year old sister and I took the train to Scarborough, a seaside town on the North Sea. We were staying for 2 weeks in a holiday chalet not too near the beach, but not so far away too.

The first night was uneventful, we were all tired from preparations, packing and travelling, and went to sleep very easily. As I lay in my bunk bed I played with myself a little bit when I was sure my mother and sister had gone to sleep, but not enough to achieve orgasm though. After a good night’s sleep things picked up exponentially, my raging teenage hormones quickly took over, and soon I could think of nothing else except sex and masturbation all day.

Then later that day came an event that may well have been the trigger for everything that came afterwards. In the late afternoon we had come back to the chalet, my mother was preparing the evening meal.

I left the dining kitchen to fetch a book from our bedroom. As I exited the bedroom and walked back down the corridor to the dining kitchen I was jolted by the sight in front of me. Right at the end of the corridor sat my sister on the toilet, her skirt up round her waist, her knickers down round her knees. She had forgotten to close the door, and I felt shocked and intrigued at what I saw as I walked back down the corridor to the dining kitchen, listening to her pee, pretending that I was reading my book but all the time secretly staring at her.

(An aside – yes woman’s “downstairs” underwear was referred to as knickers in our house, although sometimes the word panties was used. Even then I felt that knickers was naughty in a flippant non-sexual kind of way, whereas panties was a naughty in a deeply sexual and somehow dirty way.)

My head was reeling from what I had seen. Somehow the idea of my sister as a sexual creature had never entered my head, maybe because she was a year younger than me. In reality she was far more advanced in puberty than me, with pubic hair, breasts and periods to contend with.

All evening I couldn’t stop thinking about it, and had to cope with the raging hardon that enveloped my hairless cock. I hid the resultant trouser bulge by sliding my body forward under the dining table a bit. What stuck in my mind most were the skimpy feminine little panties, down round her knees. I had never thought of panties as being sexy before, but now that had changed completely. I realised that panties were part of a woman’s sexual armoury, that the sight of a pair of panties hiding those naughty dirty bits that lie between every woman’s legs was highly erotic. That night I secretly masturbated 4 or 5 times, and fell asleep dreaming of panties.

The rest of the holiday was a blur for me. I would pretend to be sleeping in the morning, now and then catching a glimpse from the corner of my eye of my sister walking around unaware in her panties. Masturbation was a constant companion, the bedclothes rose and fell rhythmically as soon as my mother and sister were sleeping. Despite the fact that the toilet door remained firmly shut from now on, I was in a permanent state of mental and often physical arousal. Girls in panties filled my mind, to the extent that I thought that nothing could ever match this sexual stimulus. How wrong I was though, I had no idea of the bombshell that was about to drop.

The holiday was over, and we made our way back home on the train. Listful and bored I sat at a table with my mother and sister. My mother read a newspaper, my sister was reading a girl’s magazine about ballet. I tried now and again to sneak a look at the beautiful ballerinas in their pretty white and pink tutus.

The motion of the train was making me luxuriously drowsy, and my mind continually drifted back to my sister in her panties, her pretty little sexy panties. And right then it happened, just after I’d looked over at those wonderful ballerinas, and then turned my head back to think of panties again. The thunderbolt from out of the blue, the lightning strike, the explosion of blinding light. The passing fancy that was to blow my relatively normal emerging sexuality completely out of the water, and change my life forever.

The thought suddenly flashed across my mind without warning – what would it be like to try on a pair of panties? The effect was instantaneous. My heart started to race. My legs started to shake uncontrollably. My hands and even my arms trembled. My breath caught, in fact I couldn’t even pant, let alone breathe normally. An incredible, mind-bending thrill, which started at the base of my penis and around my anus, welled up the length of my cock and then up my rectum and spine, passed through my belly, then rose up through my chest right up to my neck and my throat.

I was paralysed, the thought of trying on a pair of panties had unmanned me. My mother noticed that something was up and asked in a concerned voice if I was OK. My sister looked up at me. I mastered myself enough to briefly smile and nod my head. I was so relieved when she started reading her paper again, I could never have talked, at most only a gasp would have come out. I tried to control myself, and slowly very slowly by trying to put the idea of trying on panties out of my head I could breathe again albeit in short stunted intakes of breath. I had somehow managed to get my breathing under control without anybody noticing, and avoid passing out.

Shock took over, I couldn’t believe what I’d just been thinking. I put it down to some random thought that had just flitted across my mind, and tried to completely forget that it had ever happened. Maybe I could banish that thought completely? But I knew though that somewhere in a corner of my brain that dirty thought was lurking, that it would come out again to thrill me, to torment me.

And come back it did. Though we were close to home, several times again on that train journey the image of me pulling on a pair of my sister’s panties came to me. It struck brutally at my psyche and my body, making me shake, tremble and silently gasp for breath, sending shock waves through my flesh and bones, giving me a savage erection which I desperately tried to keep out of sight under the table.

Each time the fantasy laid me low I would gradually recover my senses, and bring it under control, suppress it. Then followed something that was destined to always gnaw away at me, even 30 years on – guilt and remorse. I would feel embarrassed, dirty, ashamed. I would tell myself that it was just something in my mind, something I would never actually do.

In this frame of mind we arrived in our home town and alighted from the train. But before we’d even reached home in the taxi the thought was there again. With it came the reality of being back in our house. Our house where my mother was absent 5 days per week 9 hours per day because of her job. Our house where my sister would often be absent as she spent time with her friends.

The house where eventually, at some point in the near future, I would be alone, all alone but with a pair of my sister’s panties waiting for me in her bedroom.

We had arrived back on Friday evening. School started again on Monday. All weekend I thought about it, wondering – no fearing – that the opportunity would arise at some point during Saturday or Sunday. But it didn’t, we were always together, I was never alone in the house. As Sunday drew to a close the fear grew in me though, because I knew then that Monday would be the first real opportunity, when my will would be tested, and most probably fail. Should I not simply just plan for the seemingly inevitable? I deliberately went to bed early on Sunday night, to the surprise of my mother.

I lay in bed awake though, masturbating of course. I was in denial, I tried to fantasise about something else, but always the idea of trying on the panties came back. And I was – still in denial – formulating a plan, a plan that I wasn’t sure I would even see through, a plan that would result in me trying on panties for the first time in my life at approximately 3.45pm on the following Monday afternoon. I masturbated myself to sleep, a confused and worried boy.

(Another aside - my masturbation technique was – and still is in the main – to grasp the base of my cock tight with the fingers of my right hand, then curl the right thumb round the point where the top surface of my cock joins my body. I squeeze tight, so that my cock and balls stick out from between the index finger and thumb of my right hand. I then place the tips and/or the top parts of all the fingers on my left hand on the underside of my penis, near the top so that either my left index finger fingertip or the top part of that finger lies exactly on or across the point where the penis head begins on the underside. The base of my left thumb lies exactly on the raised point on the top of the penis where the head begins. The foreskin is not pulled back. The left thumb is then swiped rhythmically back and forth so that the base moves up and down the upper shaft of the penis, with each stroke up and each stroke down moving over the raised part where the head begins. The fingers of the left hand move too, but not nearly so much, and always half a stroke behind the thumb. Nice!)

Monday morning came and I got dressed and went to school. My schoolbag was much lighter than usual, again I was in denial as to why but I knew deep down it was so I could get back home after school as quickly as possible. The schoolday was a muddled haze for me, I somehow managed to convince myself that I wasn’t going through with it. This conviction got stronger right up until the 3.30pm bell signalled that school was finished, when in an almighty turnaround, with a ferocity and resolution which actually shocked me to the core, I decided I was going to do it. I was going to do it. Today was the day I would try on panties.

I skipped the end of day registration, I would just say tomorrow that I had forgotten. Virtually first out into the playground, I started running up the stairs up onto the street, pleased at how light my bag was. I kept running, I had time but not too much, our house was about a mile away. I could get home in 15 minutes walking, 10 minutes running and walking fast. My sister was never back before 15.50pm, and usually it was after 4pm. She would stroll slowly back with her friends, chatting away, maybe look in a shop, maybe even go to a friend’s house. I kept running, it was too far to run all the way, but I didn’t want to get caught up with any friends of my own. I half ran and half walked, and eventually I made it to our front door. My hands were shaking so much it took me a good 30 seconds to get the key in the lock, but eventually I was in. I was in!

I threw down my bag in the hallway and ran to the kitchen – brilliant, still only 3.40pm, I had at least 10 minutes, in fact normally at least 20 minutes. This was it, I was shaking all over, trembling like a leaf. I could hardly walk, but I forced myself to do it. I opened the slightly ajar door to my sister’s bedroom, and closed it behind me. The curtains were closed but it was sunny, the room was very bright, perfect!

What now? Slight doubts swept across me, but I crushed them. It was now or never. No it was now, only now, never was no longer an option. I scanned the floor and then I saw them. A pair of panties. She must have been wearing them either yesterday or Saturday, my mother had washed all our dirty clothes from the holiday on Saturday afternoon. Cast aside on the bedroom floor. They were mine.

I picked them up and looked carefully. They were made of cotton, soft cotton with horizontal blue and white stripes, each about half an inch long. The legs and waistband were trimmed with thin strips of white elastic lace. They were small and pretty, my sister was quite a bit smaller than me. I noticed a small yellow-green stain on the crotch, the significance of which and it’s significance to me would only hit me months or even years later.

I placed the panties on the ground in front of the full length mirror on the wall, arranged in a certain way. Arranged in a way in which I had slowly worked out would be an easy way for me to correctly pull them on. Crotch in the middle on the inside, waistband on the outside and at the top, small panel of material at the front, bigger panel with the label inside at the back. I looked briefly in the mirror at myself, then once again quashed any doubts and frantically started removing my clothes. Finally I stood there naked and looked in the mirror. I had a massive erection, my face was bright red, I was panting uncontrollably, every limb on my body was shaking and my heart rate must have been over 200 beats per minute.

I tried to take a deep breath, then stooped down and held the left side of waistband with my left hand, and the right side of the waistband with my right hand. I stepped into the panties, my left foot finding the left hand opening for my leg, the right foot finding the right hand opening. Already the brushing of the material against my feet was electric.

Then I slowly, slowly pulled them up. I don’t know why so slowly but I’m very glad that I did, maybe I was frightened, I was shaking enough, my mind was a whirlwind of pleasure and emotion. The sensation was incredible, out of this world. I thought I was going to faint. The feel of the elastic and the cotton as they caressed first my feet, then my ankles, then my calves, then my knees, and then my thighs, where the elastic of both the waistband and the legs were stretched tight against my skin was just sensational, mind-blowing. I felt like I had died and gone to heaven.

Now the panties neared their final destination. The waistband and then the cotton brushed over my balls, continuing up the shaft of the biggest erection I had ever had. I felt the leg elastic gripping my thigh muscles tighter, the back of the waistband skimming my buttocks on the way up. It felt good, oh so good. Now they were nearly there, I could feel my balls starting to nestle in the cotton front panel, the crotch starting to make contact with the base of my penis and my anus, my pert buttocks were being cupped in soft cotton. Then, with a final little stretch as the leg elastic passed the thickest part of my thighs and slid all by themselves into place where the top of my thighs joined my body, the panties were on!

I stood looking in the mirror, and I saw a skinny teenage boy with smooth skin and long hair, wearing a pair of panties out of which stuck his at least 6 inches long solid erection. My cock was so hard it even hurt a bit, it had never been so hard. It stuck out at an angle, so rigid that the lacy elastic waistband did nothing at all to hold it in, it was stretched hard across the middle of my cock.

What I felt then was indescribable, wave after wave of pleasure was sweeping through my body. I was still shaking, every part of me, and I was panting like a bitch in heat. Suddenly I knew that I had to masturbate, and quickly at that. But what to do? My cock was straining like mad against the skimpy panties, it was actually so tight and hard that it felt a little bit uncomfortable to grasp it the way I liked to.

Then an idea struck me. After a struggle with my rock hard erection involving much stretching of elastic and cotton, I finally managed to push it out through the front of the left leghole of the panties. I tweaked the panties to the right so that the whole of my cock, and my balls too, were completely exposed. I was ready.

I grasped the base of my cock with my right hand, and gripped firmly like I always did. The material of the crotch was still clinging to me between my legs, it felt so good. Then I laid my left hand on the top of my cock, again like I always did. I started to stroke rhythmically, one stroke up and down, two strokes up and down, three strokes up and down… It was unbelievable, better than anything I’d ever felt before, one thousand – no one million times better. Then I came, after just three strokes up and down. And how I came.

I came like I could never imagine, a blinding, coruscating orgasm that must have lasted for a minute at least, up until then it was unimaginable that something so good as this could happen, in its length and its intensity. I couldn’t even see. Truly unbelievable until it happened. As the orgasm closed out I could see again. One or two pearls of white liquid had come out of the top of my cock. I was shocked, my first ever spunk! But in retrospect no wonder given the strength of the orgasm.

After about 3 minutes of shaking too much to do anything I finally peeled the panties off and got dressed again, my mind in a whirl. It was far too good to stop now, I had to do it again tomorrow! I tidied up hoping nobody would notice the tiny stain which had formed on the carpet after I had inadvertently let the spunk slide off my cock onto the floor. I placed the panties as close as possible to where I could remember finding them on the floor.

I checked the time – 15.50pm! It had seemed to last so long, but in reality it was less than 10 minutes. My sister finally came home at 16.10pm – I needn’t have worried about getting caught.

The doubts, the guilt, the shameful feelings started soon after. All evening long I was in a daze, trying to convince myself that I would never do it again. And then, when I got to bed, my cock rock hard again, I realised that I would do it again, I simply couldn’t resist. Deluding myself I was thinking maybe just once or twice again, to see if it felt the same, to see if it felt so good again even though it was such a bad thing to do. I drifted off, thinking to pack a light schoolbag again in the morning.

Coda :

This is a true story. I’ve looked up the date. The momentous act itself all took place on Monday the 23rd of April 1979, for a few minutes on either side of 15.45pm. I don’t think I’ve ever experienced an orgasm like that since, or have had such a total feeling of pure pleasure take over my whole body. I've occasionally come close, especially in the early months and years of crossdressing that followed, but it was never nearly so good, and in later years nothing even ever came close again. Could I ever regain that feeling nowadays? The only way would be to embrace my feminine side again. I would have to leave my wife and loved ones behind, hurt and mystified. I would have to shave my body hair off, buy a wig, makeup, and a new wardrobe full of pretty clothes. Feminine clothes, sexy clothes, slutty clothes, dirty sexy underwear, strappy hi-heeled sandals and sheer stockings of all varieties. Then I’d need to find a man who wanted me, and he would need to be HIV negative, and he would need to fuck me without a condom, so that I felt like a real woman. A real woman who would revel in being used as a sex object by a real masculine man. That might bring me close to that feeling again. Despite the hurt it would cause to my loved ones am I tempted? Damn right I am. Damn right.