As a teenager I always used to spend about ten days each year with Cousin Clare and her parents. Clare wasn’t actually my cousin, but her mother and my mother were at school together, and it was a convenient way to refer to her. Clare was an only child.
At the time of the following exciting adventure we were sixteen, but I was a few months older than she was.
Clare’s parents had plenty of money. They lived in a large house in rural Berkshire and Clare went to a private school, girls only, a few miles away. She had her own pony, which she kept on a farm nearby. Her mother always told everyone that Clare was far too busy to bother with boys but, looking back, I think that she was frightened of Clare growing up and going away. Clare was a normal girl underneath, but she went along with her parents’ wishes, because it was to her advantage. She was a pretty girl, slightly plump, and she had a very large bosom even at 16, which fascinated me, and I had many erections fantasising about playing with those superb tits!
As usual on these visits I caught the train from Paddington, and Clare and her mother picked me up at Newbury station. I looked forward to these trips as Clare and I were fond of each other, like cousins, and her parents were very kind. In addition there was a small river nearby where I could amuse myself fishing while Clare went riding.
At the house I was shown to my room, a different one from normal. It looked like a large box-room and had several extra items of furniture, including a big old dressing table.
Aunt Frances left me alone to unpack, and being a nosey person I had a look around, starting with the dressing table. I struck gold almost immediately! In one drawer I found a large collection of Clare’s discarded knickers!
Like most teenage boys I spent a large proportion of my time thinking about sex. I seemed to have an erection at least half the time, often in embarrassing situations, and I masturbated at least once a day, often more. I was fascinated by knickers, particularly schoolgirls’ knickers, and Cousin Clare didn’t seem to be too bothered about showing hers ‘accidentally’ sometimes. This always gave me at least half a hard on and I sometimes took myself in hand while thinking of wearing some of Clare’s underwear and filling them with cum! I’d always thought it would be wonderfully exciting just to put a pair of her knickers on, and now I’d found a drawer full of them in my room! Wonderful!
Clare’s knickers were all made by ‘Cherub’. They were all in soft cotton interlock and some were quite well-worn and slightly shiny. About half of them were in bottle green, Clare’s school colour, and the rest were a mixture of white, pink and pale blue. Just feeling her wonderful soft cotton knickers in the drawer gave me a massive erection, and I could not stop thinking about trying on some of them.
I tried not to look too eager to go to bed that night, but when it was suggested that it was nearly bedtime I needed no urging! After a cursory trip to the bathroom I went to my room and closed the door. Clare’s bedroom was at the other end of the house and she was unlikely to disturb me. I already had a hard on as I undressed, and trembling all over I slowly put on a pair of those knickers, and that made it even stiffer! I found them even more exciting than I’d imagined and for a moment I thought I was going to have an orgasm right there and then, but the feeling gradually passed. There was a large mirror on the dressing table and I adjusted it so that I could see myself wearing those beautiful knickers and the large bulge pushing out the front of them. I tried on several pairs of her knickers, putting the discarded ones on the bed, and after a few minutes I could feel that I really was going to come. I wrapped a pair of my own white cotton underpants round my erection and within seconds my cock was exploding into them. The thought occurred that I may have cum into Clare’s knickers instead, and my erection showed no inclination to soften. So after a few minutes I started masturbating in some of her knickers again, and again I caught the cum in my own soft underpants.
Exhausted, I went to bed, and feeling very satisfied fell asleep at once!
This exciting adventure was repeated every bedtime. Aunt Frances had a large washing machine and I don’t think she examined my pants before putting them in the wash, which was just as well! All went well for a few days. Then the sky darkened and the rain poured down! Uncle Mike was at his office, of course. Aunt Frances was visiting some friends for the day, and Clare said she would be at the farm attending to her pony until lunchtime. I couldn’t go fishing in that weather, so I said I would stay at home and read the set book from school, which I’d been told to read in the holidays. (It was The War of the Worlds!)
Of course, as soon as I was alone I was drawn to my room! There, I quickly took off all of my clothes. My cock was already standing rigidly to attention in anticipation. Trembling, I took a pair of Clare’s knickers from the drawer and put them on. They were so very, very soft and felt absolutely fantastic against my bulging knob. The only problem was that they felt too fantastic, and so far I hadn’t been able to prolong my masturbation for long before I had my orgasm. I was also very aware that I mustn’t come into my cousin’s knickers. It was beyond my imagination as to what Aunt Frances, or even Clare, would say if they found out what I’d been doing in Clare’s beautiful sexy knickers!
After a short while of stroking my cock I was filled with the lovely familiar feeling of my orgasm approaching, and soon I felt my cum squirting into my handkerchief. After it was over I was careful to fold the knickers and replace them in the drawer, trying not to make it obvious that I’d been wearing them. It was only mid-morning, so there should be plenty of time to have another session before Clare came home.
I read for a while, but soon gave into temptation, and carefully chose another pair of Clare’s knickers. After examining them I put them on and started to slowly massage my cock through their soft silky cotton. I marvelled at what a wonderful way it was to spend the time on a rainy day, and I was really starting to enjoy myself again when Clare’s voice, very close to my ear, said, “What are you doing wearing my knickers?”
I nearly died of fright there and then! Clare had come home early, let herself in, and had come quietly up the stairs without making a sound that I’d heard! I hadn’t shut the bedroom door properly, and she’d caught me at it in a big way! I was acutely aware that I was wearing a pair of her knickers and that I had a really throbbing hard on! I threw myself face down on the bed, not knowing what to do or say!
Clare, like her mother, was a rather forceful character, and she took charge immediately.
“Don’t be shy, Tom. If you’re going to wear my knickers the least you can do is let me see you in them! Stand up and turn round!”
Despite my acute embarrassment my cock remained fully erect, and I just had to stay right where I was, desperately wondering if there was a way out of this awful situation!
Clare said again, “Come on Tom! Don’t worry, I won’t tell mummy, but I might if you don’t let me have a look!”
I stood up very slowly. Her knickers were just about my size, nice and snug without being tight, and they appeared to be perfect for showing off my rampant erection for Clare couldn’t take her eyes off it.
“Oh Tom, your thing’s really stiff. It’s really pushing my knickers out of shape! It’s lucky that you chose a pair of my old ones!”
I could feel my face burning red, but I started to relax a little. Clare began to appear more excited than annoyed, and I was hopeful that she wouldn’t tell her mother what she’d seen. But it was still extremely embarrassing. Here I was, caught by Clare while masturbating and wearing her knickers, and with a extremely stiff hard-on to make matters worse! It was the first time a girl had seen me in such a state, and my cheeks were burning with shame!
Clare told me to turn round slowly while she continued to stare at the bulge of my cock, still as stiff as ever.
“I want to feel it, Tom! I’ve never felt a boy’s thing before!” She stepped closer.
What could I say? But my mouth was dry and nothing would come out!
Clare put her hand out and grasped my erection through her knickers. It was like an electric shock, and I gasped and gave a moan!
She looked closely at my stiff cock in her hand, and murmured, “It’s really hard, isn’t it! Is it always as hard as that when you’re worked up?”
“Yes, always,” I gasped. “But if you’re going to hold it will you do it more gently?”
“Oh, sorry,” she said. She relaxed her grip. “Is that better?” She gave it a little rub, and I just gulped, and nodded ‘yes!’
In fact it was the most amazingly exciting thing I’d ever experienced since my first orgasm a few years before! Wearing girls’ knickers, having a hard on in them, and being masturbated by a girl, was definitely my kind of excitement!
I could see that Clare was getting turned on by what was happening. Her face was slightly red and she was breathing hard. Her other hand strayed between her legs for a moment before she realised that I could see her. After a while I took her hand away from my cock.
“What’s wrong?” she asked, looking a little hurt. “Don’t you like it?”
“I like it too much,” I whispered. “If you don’t stop there’s going to be an accident soon!”
“What sort of accident?” She whispered in return.
“There’ll be a terrible mess in these knickers in a moment if you keep going, and then your mother will find out what we’ve been doing!”
“Oh, mummy won’t find out. I’m sure she has forgotten all about my old knickers up here. They’re very old, and I don’t wear them very often now.”
I was thrilled to hear her mentioning her knickers so affectionately, and my cock throbbed even more. She gently squeezed it and continued gently massaging it. I was very relieved that she now seemed almost as guilty as I was, and I wasn’t going to stop her from giving me such a wonderful feeling. I decided to lie back and enjoy the touch of her hand!
Needless to say, it didn’t take long! I groaned with pleasure as my orgasm started. I could feel the hot cum rising and squirting into her wonderful knickers, and I almost passed out with its intensity. It was a very long orgasm, and one of the best I’d ever had, made all the more so because it was Cousin Clare who had caused it! She seemed fascinated by the growing wet patch in the front of her knickers as my spunk soaked into and them and spread over their soft cotton. Sadly it was soon over. Clare went to wash her hands, and I took off her wet knickers and dried myself before dressing. Clare suggested that I should carefully hide her wet knickers.
“Don’t worry about Mummy missing my knickers from the drawer,” she told me. “I’m certain that she doesn’t know how many knickers I have in here”.
That sexual adventure turned out to be the first of several that we shared and enjoyed while I was staying at their house. Clare wouldn’t let me feel up her skirt at first, but it was obvious that she was getting very aroused each time she ‘masturbated’ me, and eventually she allowed me to stroke her pussy through her knickers. Putting my hand inside them was forbidden, but it was wonderful to be able to see and touch her through her knickers like that, and she didn’t take long to have an orgasm. When she had shown me exactly how to do it as she liked it, she sometimes had more than one orgasm, and seemed to love having them more each time.
All too soon the holiday was over and it was time to catch the train back to London. Clare had kindly given me five pairs of her old knickers, ‘to remind me of her when I wore them’, as she put it! The following year seemed to be a long way away, but I looked forward to it with great desire and anticipation. Cousin Clare was obviously not the completely innocent girl that her parents seemed to think, and the next year would prove it.