When Did It All Start?

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When did it all start? I don’t think I know, but my interest in the kinkier side of sex in the relationships between me and the small number of women I have known has always been there. The problem is that mostly these women have not, and are still not, interested in it as much as I am. So I am left largely to amuse myself, secretly and alone, and safe in the knowledge that this really doesn’t harm anyone.

I have vague early memories of a need to try out tights and pants though why I can’t think. I am, and always have been, turned on most by slim ankles, calves and buttocks. Someone then showed me a men’s magazine, and the world of stockings and suspenders was opened up to me. After seeing this for the first time I was hooked. I fantasised as a young boy about any girl in stockings and any girl I fancied I dreamt of her in stockings. I hadn’t had a serious girlfriend for quite some time, and many of those I fancied turned me down as I was a tad serious and quite clever, a bit of a turn off. However there was one girl who seemed to be interested in me, more so than I in her. I went through my first year at ‘A’ level having a few snogs and fondles with some very nice girls but no lasting relationship. Then came rag week and getting together with J for the first time. Not quite sure how it happened, but she sensed my interest in stockings almost without me saying anything.

By the time we hit the second year of ‘A’ levels we had spent a summer getting to know each other. Her breasts were fantastic, silky firm flesh, quite small but very pert and she was very happy to share them with me at regular intervals. I had heard rumours of J having had a regular bloke in K, but she was over him. Didn’t always look that way at student events, but I was still getting more access to sexy flesh than I had ever had, and in fact than many of my friends had. J was a bit possessive, and I took some taunts for this, but the regular fondling sessions were not to be missed and she held out the promise of full sex very soon, something I was nervous about but absolutely on for trying.

One student party in the late summer we finally got over the hurdle and had full sex. I remember the bedroom we snuck into but not who’s house it was. J was in tight jeans which I had a difficult time taking down far enough to slide off her small feet. She was only 5ft 3in and slim with it, so her slender, firm calves and thighs were a sight for my sore eyes. J got to work on removing my jeans and my cock sprang free from my (no doubt very unsexy) underwear. After some frantic snogging and fondling, I reached down and slipped my hands through the fine downy hair and between her sex lips. I almost came then, such was the electric shock of slipping a finger into that tight love hole for the first time. J was getting wet and very aroused and I couldn’t wait – not much of a gent at that time, something which I am glad to say has changed. She didn’t seem to mind and though we were not drunk, we had at least had a sip or two. Caution was thrown to the wind as I entered a woman for the first time.

It was fantastic, though not as tight as I had been led to believe by all the reading of those slightly dodgy magazines. I started to pound away in my clumsy fashion, not quite knowing what I was doing but feeling bloody marvellous. J started to move under me as I entered fully into her but it seemed this one would be over quickly. I could tell I wasn’t going to last too long, and without protection I was far to scared of the consequence to let it go inside her. After what seemed a very brief time I had to withdraw quickly and found myself shooting all over her flat, bare tummy. Still, I had done it for the first time, and J assured me that it was her first time too, giving me a hug after we had cleared up the mess I made. I am still not sure, all these years later, as there was no tightness or no resistance – but who am I to complain, I was no longer a virgin.

We started to really get into it then, but we always worried about the consequences so I withdrew each time. J made it clear that she was not a fan of condoms but as I still wasn’t lasting too long this didn’t make for very satisfying encounters for either of us. I tried to get her as aroused as my inexperienced years would let me, but I know she didn’t have her own orgasm during these early bouts of sex. However, it was all to change for the better. One day I noted J was late for a shared seminar, and at lunch we snatched a few moments. I also noticed her legs were unusually glossy, the normal nylon had been replaced by something much more sheer. As I stole a kiss and a fondle of her fantastic tight bum I felt something new – suspenders. I almost sprang out of my pants as I broke the kiss to check it out. J smiled, white perfect teeth gleaming. She went on to let me know that this wasn’t all that had changed. Without telling me she had chosen to get the pill and make it safe for both of us to have fun. We celebrated with a dam good snog and a fondle of her stocking covered legs, a feeling that even now raises the hairs on my legs (when I have left them on!) and the cock in my pants.

The next 10 or 11 months were a blur of trying to find as many opportunities to shag in as many places as we could. I have amazing memories of some of our daring ones. There was a trend of big, wide circle skirts in those days, and one evening at her house, J returned from the bathroom and dropped her tiny knickers on my lap. I sprang to attention as normal and hid them quickly, we were after all in the dining area between her parents lounge and their kitchen. Listening out J quickly unzipped me and sat on top of me, sliding my cock straight into her waiting cunt! She was just getting comfortable, and had settled me as fully as she could inside her, when her mum came through. I can still recall being inside my girlfriend, covered in her circle skirt and smiling politely as the tea was made and her mum returned to the TV. I remember too the force of the orgasm I had once J started bouncing up and down on me. I was so aroused by the thought of what had just happened I shot my load of cum very quickly into her willing folds. J stayed on top and allowed the mix of our juices to run slowly out and down around my balls before quickly slipping me out and covering me up, wet and sticky inside my teenage briefs.

Another time we were both in the college play, and J chose to wear her sheer black, seamed stockings underneath the 1920’s nurses uniform the part called for. When we had 20 minutes between appearances we snuck off into the main college block and found one of the class rooms we normally had studies in. Down in one corner we shagged hard, J’s legs up around my waist, panties tugged quickly to one side, as we pounded away. Still not quite mastering the art of holding on I was cumming too quickly, but this time she did at least achieve her own climax, something which normally took a lot of foreplay before my short thrusting. The excitement of the location and the speed at which it all happened had turned her on more quickly than usual.

We explored straight sex quite regularly after that, though mostly quick snatches in our respective houses. Occasional seminars were missed when no-one was at home and I started to hint at high heels, tight fitting boots, sex with clothes on and other things that I thought might just turn me on a little more. They duly did, and J was a willing accomplice in this very vanilla set of variations.

One day in the hot summer J turned up at our house when we knew the family were away. On her slim calves were the current fad – espadrilles, with thin laces wrapped around and tied up, giving a wide mesh effect. Her skirt was a wrap round one in thin red cotton, the sunlight silhouetting her legs all the way to the gap at the top of her thighs. The thin straps of the halter top were tied behind her neck and as we kissed I discovered these items were all she had on. She was very aroused, as she had travelled on the bus and walked to our house, taking around 30 minutes, and the daring nature of this had got her very wet indeed. I remember dragging her inside and straight upstairs (traditionalist at the time!) where I stripped off my shorts and pants. Not needing to do any more undressing we fucked immediately on my bed, both cumming very quickly with the excitement of it all. To two 18 year olds new to sex this was very hot indeed, but seems somewhat lame nowadays.

We eventually started to look for opportunities to have sex in unusual places, and J was frequently without underwear in common situations such as in college or around home. Her breasts were very firm and pert, so going without a bra was easy to do and fantastic to see. Her nipples were easy to arouse and she got a lot of looks on our Fridays out with friends as the top often hid little. She experimented with half and quarter cup bras, but we had to be careful as the late seventies were not that liberated in our part of the world so parents did not need to see this clothing in the washing basket!

One occasion stays with me when we went home between lectures. Passionate kissing and slow fondling led to me sliding my hand under her tight skirt. Although we had been at college J had worn sheer stockings and suspenders, and the tiniest of g-strings hiding her neatly trimmed pubic region. Her labia were already wet when I slipped my finger past the flimsy material and between her cunt lips. Undoing her blouse I became harder at the sight of the quarter cup lacy bra, pink nipples standing proud above the material. I wanted to make love with most of her clothes on this time, and for the first time tried a rear entry position. J lay face down on the bed. I slid a pillow under her hips and lifted her skirt. Sliding the tiny fabric to one side I was able to thrust straight into her waiting hole. J grunted and squealed at this, a new sensation from the different direction my cock was entering. I got quickly into a rhythm and though I came quickly I was staying hard and continuing to pound away, excited by the sight of J lying face down, fantastic tight ass presented to me and the slurping of my still erect cock as it slid in and out of her well lubricated cunt. I remember she came, one of the few times this happened without a lot of foreplay, and I was hugely pleased as I always felt slightly sad when I got my own orgasm but J didn’t.