Tom, his sister, and her school knickers.
I was brought up in a village in Hertfordshire in the 1950s and 60s. I lived with my mother and sister, my dad having taken off to find some excitement when I was quite small. My sister Sally was about a year older than me. Sally tended to look down on me, both because of her age and the fact that I was a mere male! Mum, while she was very kind, was very Victorian in her outlook. She tended to regard any discussing of sexual matters, almost anything below the belt, as rather dirty, and never tried to give me even the slightest hint about puberty or the ‘Facts of Life'!
Sally and I lived in a sort of truce most of the time, with a battle likely to break out at any minute, while our mum tried to keep the peace. However, Sally was a clever girl and eventually went to college to get a degree. She also had inherited Mum's fastidious attitude to hygiene, washed her hands frequently, and she bathed far more frequently than was necessary in my view! She also changed her clothes frequently, especially her underwear. This was to my advantage as she put her discarded underclothing in the laundry basket in the bathroom.
Maybe it was because of living in an otherwise feminine household, but I became fascinated by knickers, especially the sort worn by schoolgirls. I started 'borrowing' Sally's knickers when I was just twelve, and soon developed a strong compulsion to do so. When I tried a pair of her knickers on for the first time I found them even more exciting than I ever thought they would, and after a while I had my very first orgasm. This caused me to develop an eternal passion for girls' underwear and for taking myself in hand as I did so! At the beginning my orgasms were ‘dry', all feelings and no mess, but when I started to cum a few months later I was extremely lucky not to have an 'accident' in her knickers. That would have been suicide, and occasionally it was a very near thing!
I always wore Sally's discarded knickers. They were always pristine and unmarked, and she changed them one or twice a day. Mum worked hard to keep up with her demand for knickers and washed the family clothes at least twice a week. Sally had about thirty pairs of school knickers, including about a dozen in her school colour, which was dark green. The rest were in various colours, and mostly pale blue, pink and white. The freshly washed knickers were always carefully ironed, and then neatly stacked in the airing cupboard. I often went there to feel and kiss them gently, but nothing more. Any attempt to wear them would have been instantly detected, with dire consequences I was sure! But still, her worn knickers were wonderful and silky. They invariably gave me a stiffie even before I actually stepped into them and pulled them up!
Most of the boys in my class were quite normal, and some of them openly discussed their wanking exploits. Mostly they were trying to impress the others with the depth of their depravity, I think! Another group, myself included, kept their masturbatory adventures private, admitting only that they did it. There were two boys, both of whom had been caught in the act by their parents, and had been warned about the appalling consequences (short sight, insanity and hairy palms being mentioned!) if they did it even one more time. These two lads refused to even discuss such smut after that! Personally, I had so much sheer enjoyment from wearing Sally's knickers that I couldn't give it up if I tried, and I had no intention of trying!
Sally's school knickers were all of very soft cotton interlock, and they were all 'Cherub' knickers. They were all of beautiful quality, and some of the green ones even had knicker-gussets continued up the back to the waistband. I discovered that these knickers were for wearing in the school gym. The other knickers were more conventional but equally devastatingly attractive to my trembling head, and I loved each and every pair of knickers that I could find, wherever they were!
When I was sixteen I was at home during the school holidays. My mother said that she and Sally were going to have a day out the next day, and going around the shops in St Albans. Apart from the chance of having a sneaky look at the ladies' underwear in the department stores this held no interest for me, so I said I would stay at home and study. The following morning was rather damp and murky, but the intrepid duo put on their coats, opened their brollies and went up the road to catch the bus. I waited for about half an hour in case of an unforeseen return home, and then went upstairs to the bathroom to see what Sally had unintentionally left for me to try on! I selected three or four pairs of knickers and, as an afterthought, a suspender belt and a pair of stockings. I had already discovered that I liked wearing her stockings occasionally, and I still do!
By the time I went to my bedroom with my sister’s exciting underwear, my prick had already started to stiffen at the thought of the pleasure shortly to be enjoyed. By the time I'd undressed it was standing to attention in fine style. I put on the suspender belt and carefully stretched the stockings up my legs and fastened them to the suspenders. I had become quite expert at this, even at sixteen, and it's a skill I've never forgotten! I selected a pair of bottle green knickers as a tribute to all the lovely girls at the High School. By the time I had pulled them up I had a really throbbing erection, relishing the sensation as the head of my cock rubbed gently against the soft cotton of the knickers as I moved. I knew from experience that it wouldn't take long for me to have my first orgasm of the day. For a while I gently massaged my knob through the knickers, trembling with erotic excitement. All too soon I could feel that my orgasm was near. I pulled down the girls’ knickers and carefully wrapped a handkerchief round the head of my penis before pulling up the beautiful knickers again. Twice I teased myself by stopping at the edge of the orgasm. I let myself recover a little before beginning to massage again.
The third time I couldn't stop. I groaned with the sheer intensity of the orgasm and felt the intense cum pumping up my rigid prick and squirting into the handkerchief. Feeling faint with the effort I rested on the bed till the orgasm faded a little. Then I pulled down the knickers before the copious cum leaked through my handkerchief into them for there was rather a lot of it. Then I went to the bathroom, took off the knickers and replaced them in the laundry basket. I had a good wash and dried myself. I had no worry that Mum would notice the bulge in the front of the knickers as she always seemed to put all of our family underwear in the old washing machine without examining it.
And why indeed should she want to examine her daughter’s knickers!
Back in the bedroom I waited for a while to make sure that I wouldn't have a small accidental leakage, before putting on a pair of my sister’s wonderful pink knickers and admiring myself in the mirror.
I still had my initial erection and still felt incredibly randy, so before long I was massaging my prick again, with the same feelings of sheer pleasure as I felt the head of my cock through the soft, silky cotton knickers. What a lovely feeling it was! I was really enjoying myself and this time I planned to make it last as long as possible before having the next climax. I’d found that this was easier the second time around! After a while I stopped for a few minutes to cool off a little, before starting again. I was really enjoying myself. The fact that I was wearing pink knickers made it all the more exciting as it has always been my favourite colour for knickers. My eyes were closed and I was in a wonderful knickers world of my own, and concentrating entirely on my massively stiff prick, my sister’s pink, silky knickers, and the wonderful sensations I was enjoying.
Suddenly I almost jumped out of my skin and my heart stopped as the bedroom door opened, and there in the doorway staring at me, was my mother, with my sister Sally peering right behind her!
My instinctive reaction at that moment of terror in almost unstoppable orgasm was to turn my back on them and wish that they would go away.
"Turn round!" My mother barked, and I reluctantly did so. I had been right on the critical edge of having the orgasm, and I was intensely embarrassed to be caught with such a rampantly erect prick, as well as actually wearing Sally's knickers.
But there was worse to come! It must have been the shock of the door opening and the rubbing of those knickers against the sensitive head of my prick as I turned around, but I suddenly started to cum, right there in my sister's knickers, while she and my mother looked on! It was a massively intense orgasm, and I couldn't help groaning with the intensity of it as I felt my cum surging and soaking into Sally's knickers! My legs went weak and I staggered forward a bit. Words failed each one of us, and for several long moments they just stared at my incredible situation. When I eventually looked up they were still staring at the front of Sally’s very wet, pink knickers. Eventually our eyes met, and I felt weak and devastated. Then, with a final look at those bulging wet knickers, Mum turned and ushered Sally from the room.
‘Oh dear', I thought to myself!
Half an hour later I was downstairs, dressed normally, and being confronted by my mother. My sister had already said that she would never speak to me again, and that she wanted new knickers to replace the ones I had treated so shamefully. My mother was almost speechless, probably because she didn’t know that such things took place in her house!
My sister made good her promise to totally ignore me in the future, while my mother reminded me of my sins on a daily basis for many months. In the end, completely fed up with the nagging and bad atmosphere, I went into an Army recruiting office and signed on with the Boys' Service. My mother readily signed the approval forms, saying that it would make a man out of me!
As for wearing knickers in the future, I've never been caught again. I'm much too careful these days!