Karens First Time

I'm fifty five and if I had to nominate the most memorable sex I had ever had then I wouldn't have to think very hard, the choice would be easy. Note that I said the most memorable sex ever -- not the best.

It was back when I was twenty three and I went out with a girl called Karen. She was very slim, with an almost boyish figure. In a short skirt her legs looked fantastic, but given her slim build it was pretty inevitable that she was distinctly flat chested. I have always had a preference for something that's a nice handful, though I'm not saying there isn't a case for small, perfectly formed breasts. If you're a man you've just got to love tits, no matter what size they are.

The real problem wasn't the size of her tits, it was the fact that I wasn't getting much else. We'd been going out for nearly two months and I'd got nowhere. Yes she'd let me feel her tits and eventually I'd managed to slip my hand inside her knickers, but that was very strictly rationed.

The worst part of it was that she didn't really seem interested. On the rare occasions that I got to touch her pussy she didn't give much sign of being aroused. She didn't get very wet and there was no heavy breathing, none of the sighs and moans that I'd been used to hearing from other girls.

I was thinking she was a bit under-sexed or perhaps she was just saving it for Mr. Right, because I was pretty certain that she was still a virgin even though she was eighteen. She was a nice girl, but shy and rather inhibited, and everything about her spoke of virginity.

I have to be honest and say that inevitably I saw that as a challenge and hoped that I would be the one who got to remove her knickers and claim the prize. I could certainly imagine that the sex would be very good -- that slim build and boyish hips meant that she had a lovely tight pussy.

Several times returning home after another night of frustrated fumbles I had jerked off thinking how pleasant it would be to spread her legs and explore virgin territory.

However it became clear that our relationship was going nowhere and that my dreams of taking her virginity were going to stay just that -- dreams.

We'd been out one night and I was returning her home, wondering idly if I was going to have any luck tonight and whether it might be best to call it a day -- I couldn't imagine that Karen would be upset, perhaps she might even beat me to the punch.

We got to her street and a broken down car and a breakdown truck were blocking the road, but that wasn't really a problem because a driveable track led round to the back of her parent's house and I could easily park there and we could go in through the garden gate.

I parked up and it was the sort of June night that we don't see enough of in England -- no breeze and a lovely warm evening. We went quietly in through the garden gate and approached the house from the rear. There was a dim light visible through a gap in the lounge curtains. Karen remarked that was odd because her parents were out and not expected back until quite a bit later. She said that Debbie and Dave must be in. Debbie was her twenty one year old sister and she was engaged to Dave, with the wedding being arranged for next year.

"Let's see what my sister's getting up to," said Karen and approached the gap in the curtain. I think it shows how naïve and inexperienced she was in that she was presumably thinking they might be indulging in a bit of kissing and cuddling on the settee.

She stopped close enough to the window to be able to see in, but not so close that she would be visible to the occupants of the room. I moved behind her and peered over her head.

What I saw was startling. Debbie was naked except for a pair of white satin panties and was just in the process of kneeling on the floor. Even in my shocked state I registered that she really did have a lot more curves than her younger sister. Dave was stood above her, naked though his trousers were round his ankles. His cock stood out rigidly in front of him.

It was an incredibly striking scene. They were an attractive couple and would have graced any porn movie. Debbie had curves in all the right places and a lovely pair of tits with prominent nipples (she must have been very aroused!). Dave looked much more athletic than I expected -- a broad chest and flat stomach and a cock that he could be justifiably proud of. Even in the dim light the bulbous head and prominent veins were clearly visible. The voyeuristic element only added to the eroticism of what we were seeing; it was as though we were watching our own personal porn movie and I could feel my cock straining at the front of my trousers.

Kneeling in front of him Debbie gently cupped his balls. I had put my hands on Karen's hips, but now I slid them smoothly upwards and cupped her breasts. She was wearing a T-shirt, but no bra and her nipples were encouragingly prominent -- it felt like they were trying to poke a hole in the material.

With one hand still cupping his balls Debbie wrapped her other hand round the base of his cock and began a gentle pumping action. After a few strokes she looked up and gave a wicked grin, lowered her head and her tongue flickered out and with a few rapid, reptilian flicks teased the end of Dave's cock. He groaned, so she did it again; I began to squeeze Karen's tits, she stayed completely motionless, but the tension was incredible.

Again Debbie lowered her head this time taking the tip of Dave's penis into her mouth and seemed to swirl her tongue around in a way that obviously gave Dave exquisite pleasure.

After a brief spell of that she paused and licked her lips. Then she looked up and gave Dave another wicked grin, it was very clear just how much she was enjoying pleasuring him. Later I did wonder if it was this which influenced Karen so much -- the fact that her sister wasn't just having sex, she was revelling in it, taking the lead role and making it clear with her every movement just how much pleasure she was getting from giving pleasure to her man.

My left hand continued to feel Karen's breast, but my right hand slid down and began to stroke her pussy through her skirt.

Now Debbie's mouth slid back down and took all of Dave's penis into her mouth. She was really deep throating him, her lips reaching the base of his cock. Dave's head was thrown back, his eyes shut tight in what almost seemed to be an anguished grimace, but clearly was an experience so exquisitely wonderful that it was almost painful.

However the most striking thing was the look on Debbie's face. Even now over thirty years later it's still etched in my memory as the most erotic thing I've ever seen. Her eyes were half closed, normally that might have made her look sleepy, but her eyelids were weighed down with lust; that was all it was, pure lust was on her face.

My right hand slid up Karen's skirt and between her legs. I didn't think my cock could get any harder, but I'll swear it stiffened further when I felt how wet her panties were. They'd never even really got damp before, now they were well beyond that, they were incredibly wet. Meeting no resistance I slid my hand inside and slipped a finger into her love tunnel. I've said what a lovely tight pussy she had, but tonight was different, it was all warmth and wetness.

I was slightly distracted when Dave disengaged himself from Debbie's oral attention, hurriedly kicked his trousers off and threw himself between Debbie's legs. It was clear they were going to fuck and it took them out of our view and broke the voyeuristic spell.

I've never been as aroused since then as I was at that moment. My need to fuck Karen was urgent and all consuming. It was the only thing I could think about, nothing else mattered, I had to push my cock into her cunt and empty my balls inside her.

I pulled her down onto the lawn and we kissed greedily. My hand went straight back between her legs, but this time I tugged feverishly at her knickers. There was no complaint, no attempt to stop me, and in seconds a pair of white knickers were tossed to one side.

Hurriedly I unzipped my trousers and took my cock out. I moved between her legs and our eyes locked on each other as I positioned my cock against the entrance to her virgin pussy. Mindful of her inexperience I managed to control myself and instead of thrusting wildly I penetrated her as smoothly and carefully as I could.

Even in the midst of such incredible passion she still managed to suppress her emotions. As my cock slid between her cunt lips she closed her eyes and gave a barely audible gasp.

At that stage in my life there had only been three women I'd had sex with and since then there has only been one, but none of them were anything like Karen. That slim build and those narrow, boyish hips gave her the tightest cunt imaginable. Even though her love juices were finally in full flow, there was still an overwhelming feeling of tightness. A wonderful velvet grip that squeezed my cock and drove every other sensation from my mind.

All I could feel was my prick in her cunt - there was nothing else. I'm surprised I didn't come straight away, but somehow I did manage to exercise some control. Nevertheless after a few strokes it was clear that I couldn't hold out and even if I pulled out I was still going to cum. I gave one last thrust and then groaned as my prick jerked and jerked and fired several bursts of cum into Karen's virgin pussy.

We clung to each other for a while, then Karen said rather curtly that she had to go. I was surprised, and disappointed, at that. I wanted to hold her, caress her, share what we had had together and at last experience some intimacy with this shy and reserved young woman. But it wasn't to be. She insisted she had to go, quickly pulled her knickers back on and hurried into the house. Stood in the garden feeling somewhat rejected I wandered back towards my car.

On the drive home I had time to reflect on the fact that I hadn't even vaguely worried about birth control, perhaps Karen was on the Pill, I really had no idea whether she was or she wasn't. Well it was too late to worry now, the deed was done. The way Karen had bolted indoors had taken some of the gloss off it, but still I had done it, I had removed her knickers and fucked her virgin pussy.

Mind you I knew that wasn't down to my charms, it was clear that if we hadn't witnessed the full-blooded way in which Debbie embraced the sexual act then Karen wouldn't have acted in the way she did.

I did hope that we had crossed a line and our relationship would move on to a new, more physical level. I rang Karen the following day and she said she wasn't free to see me during the week, so I had to wait until the following weekend.

It was immediately clear that the barriers were back in place, and if anything they had been reinforced. She seemed embarrassed by what had happened and without going into details made it clear that there wasn't going to be any repeat. She did also leave a clear hint that it was the wrong time of month, so at least I knew I didn't have any worries on that front.

Instead of bringing us together, it just seemed to force us apart. Karen's attitude seemed to be that she had been caught in a moment of weakness. Perhaps she felt I had taken advantage of her, but caught in such an intensely erotic situation any red-blooded male would have done what I did.

We split up soon afterwards. Ironically a couple of months later I started going out with Kim, one of Karen's closest friends. We hit it off really well and although she was also a virgin there was none of the coldness and reserve which I had experienced with Karen. Sex came naturally and was wonderful, passionate and exciting and eventually we got married.

We've been married for nearly thirty years now and whilst we've had our ups and downs it has been pretty good. We still see Karen two or three times a year. She stayed single for quite a while, but then married a man fifteen years older than her. They seem happy, though there are signs that the physical side of their marriage came to a halt years ago.

There's no residual attraction left between Karen and I. Though I have to be honest and say that if she made it clear that she wanted to have an affair with me I would be very tempted. But I haven't seen the slightest indication that it's at all likely to happen.

Nevertheless there was a recent occasion which triggered a memory of that June night. We were at a dinner party when one of the wives told us in a part-amused, part-shocked tone how she had accidentally turned on the porn channel at a hotel they were staying at and been confronted with film of a woman enthusiastically sucking a man's dick. We all laughed at her description, but my eyes caught Karen's and it was obvious what we were both thinking.

I know it gave me an instant hard-on and I wondered if it made her wet. Perhaps not, but there must be times when she thinks back to that warm summers' night and how she was swept along by a wave of passion and allowed me to take her virginity. I know I do.