Kate: Breaking in a virgin. Part III

Unusually I found myself really looking forward to the evening with Chris. There was something about him that was affecting me.

Whatever that initial animal magnetism that brought us together was, it was still there; raging through my system, more primeval than being left to survive on the Serengeti naked and unarmed in the middle of the rutting season. But there was a human element too. He was a nice guy. I felt suddenly motherly and protective of him while wanting to screw him mercilessly all at the same time. My desire for him wasn’t diminished by his lack of sexual experience; it just meant I needed to take the lead and allow him more room for learning.

I’d texted him to dress for going to a night club after dinner.

I usually dress to impress for this sort of night, but for this one I went top shelf. My chosen dress was a strappy iridescent blue sheath mini, so deeply plunging at the front that you could see side boob from the centre as well as from the sides. Needing to be worn braless I was thankful for my still perky breasts.

In my excitement I arrived five minutes early to find Chris still in the shower after a late arrival back from surfing and Ben shirtless answering the door. Ben let me in but after knocking on the bathroom door to tell Chris I was here, ushered me over to the lounge on the far corner of the room on the pretext of giving me somewhere to wait.

Sitting close to me he lent in and, while staring straight down my cleavage in a barely audible voice asked if I’d like to go out with him the following night. I’d like to say I was shocked, but unfortunately I’ve seen this ruthlessness before.

And in a way I had initially read Ben as being a likely suspect for this; cocky and arrogant enough to think he was a better prospect than Chris and so I’d jump at the opportunity to switch boats. But he was wrong on at least three counts; first I had the raging hots for Chris, secondly even before this moment I’d found him a less than desirable person and thirdly that even if he had been attractive I wasn’t the sort of girl who’d let myself be played between friends like that.

But I also knew the situation had to be played carefully. If I was anything less than charming in my push back I’d be written off as a bitchy slut, not just in his own mind, but to Chris and all his friends too – thus reducing the value of what Ben perceived as Chris’s conquest.

I have to give the comment that follows this a context; but that’s hard to do without sounding stuck up. As regular readers know, nature has in some respects been very kind to me. I’m what most guys would call a “looker”, as in ‘good looker’ (and no, I didn’t mean to start that with a ‘h’). Pretty faced, blonde haired, I’ve got perky D Cup breasts mounted on a tall, slim athletic figure. There’s enough curves to look good without suggesting I’m going to get fat as I get older. I’ve even been given nice clear skin; and I suppose I should add, enough brains to let me transfer from law school to med school next year.

So I know I attract the attention of guys. Dressed like I was that night I also know I looked drop dead, cock burstingly gorgeous. And nature even gave me the confidence to deal with that instead of wanting to hide it.

Of course nature gives and she takes as well. My parent’s marriage breakdown when I was young has also left me with very serious commitment problems. I’m certainly not going to look down on another less well-endowed girl when I know she’s likely to be blissfully married with three beautiful kids while I’m still having to sleep around for my satisfaction.

The point of all that is that, in a motherly way I really wanted Ben and his mates to perceive Chris as having scored the high value conquest I knew I was and I didn’t want to offer Ben any excuse to undermine that.

And so, with a pat on his thigh I told him I was hoping Chris might find some more time for me tomorrow night so I wouldn’t be free. Then, to exit the situation quickly and as best I could, I stood up and walked across to the bathroom door, made sure the shower was still running, knocked on it and let myself in.

Chris was just turning off the shower as I put my head in the door, so I gave him a sloppy greeting kiss and asked him if he’d like me to dry him off, then stood chatting to him as he leaned naked and by now visibly aroused over the vanity unit shaving. Then I went into his room with him and kept chatting as he got dressed.

The dinner was great and then we headed off to what passes for the area’s night club. Called “The Only” – for good reason - it was located in a town about half an hour’s drive away, so I needed to stay sober. Frankly it’s a bit of a dive, and all the kids know it. But having a monopoly, it still gets well patronised by my friends. For a couple of hours I alternatively showed off Chris around my circle of friends and acquaintances and seduced him to the point of full arousal with our dancing; all the while encouraging Chris to get lots of selfies of the two of us to show off to his mates back home and collecting a few for myself as well.

When we lobbed back at Chris’s unit Ben was still up playing around with his computer. Frankly Chris and I were now fairly focused on other things so we played scant attention to Ben as we attended to the preliminaries and retired behind the door of Chris’s room.

After closing the door behind us, Chris came up behind me, pressed his body against mine and started nuzzling my neck as he slid his hands under the side of my dress and cupped my breasts; thus confirming this dress’s 100% achievement rate in producing that reaction in any date I wear it in front of. There’s just something about that under-boob display that compels guys to do it; even those I’m not about to let undress me.

I put my hands behind my back, undid his belt and pants and pulled down the front of his undies to expose him, before pushing myself back against him. Chris used the hands under my dress to lift if off over my head, leaving me just in my shoes and a pair of sheer, silky, string sided, Brazilian cut undies in a blue that had matched the dress. I turned around and started undressing him, completing the task of slipping his pants and undies off his legs, taking off his shoes and undoing the buttons on his shirt to slide it off his body before throwing him stark naked and rampantly aroused onto the bed. Then I kicked off my shoes and jumped on top of him and started kissing him.

This time it was Chris who took the lead, rolling me over on my back and leaning half over me like he had when he’d fingered me. With a hand ever so lightly playing against the crutch of my knickers, he started working down my body; nuzzling my neck, tonguing and lipping my nipples and breasts and kissing down the length of my stomach before munching lightly on my undies over the turn of my mons.

With his finger by now pushing them further up into the valley between my labia, he briefly brought his mouth up next to my ear and whispered “they are the sexiest undies I’ve ever seen” before going back to kissing the area just above and under the waist band. All this time he’d been increasing the pressure and intensity of his fingering; stimulating me just as effectively – maybe more so - with my undies on as he had against a bare clit earlier. I could quickly feel the undies go wet under my body’s outpouring of juices.

This was a bit of a novelty for me. It had been a long time since guys weren’t in a hurry to get my undies off me and back in those days they showed nothing like Chris’s skills with his fingers; indeed they showed no skill at all.

Periodically he’d use his fingers to spread my lips and open up access to my clit and bring his mouth over and kiss it or push his tongue against it to wiggle it about; all still through the material of the undies which had now become so wet – and I assumed see through – they might as well not been there at all.

Then suddenly they weren’t as Chris indicated for me to lift my hips as he slid them down my legs and off my feet, on the return journey burying his chin into my crutch and tonguing my clit.

I’d already decided this time I wanted him to experience my orgasmic contractions on his cock. I pulled his head up and encouraged him to stimulate my nipples while he continued to finger me. There might be a fairly small window between when I was progressed enough to be certain I’d have time to come with him inside and so close to coming I’d lose the will power to make the transition. I needed him half in position already.

As the moment approached I slid the condom over his cock without disturbing his fingering. When it arrived moments later I rolled him on his back and mounted him cowgirl style and started pounding up and down on top of him. And finally as a beautiful orgasm washed through my body I let out a blissful cry loud enough to make sure Ben could hear it while doing everything I could in the moment to reinforce the impact of my contractions on the still rock hard cock I could feel penetrating deep into me.

After letting my orgasm unhurriedly have its way with my body, I squeezed myself around his cock a little tighter and started lifting myself up and down on top of him. Slowly at first, I’d bring him half out of me before burying him deeply again, pushing down hard enough to start stimulating myself against his pubis again.

I started out telling myself this second phase was entirely for him; but it wasn’t long before I found myself wanting more – a second orgasm. I persuaded myself it would be good for his ego and sex education to see that a woman could do that and he could deliver it. And so by degrees I stopped trying to increase his stimulation and started to once again focus on my own; even lifting his head back up to my breast to remind him to keep working my nipples.

I found it too. Again moaning my pleasure out loud and long enough for Ben to unambiguously know what Chris had achieved, this time I clamped around him tightly trying to increase the force of my contractions; pulsing my pussy on him. As I emerged from the cocoon of my own orgasm and focused on Chris again, with almost the very first movements of my body against his, I looked down to see his face once again wearing that cute little pre-orgasmic look of intense concentration, before he closed his eyes, let his head drop back, let out a long deep muscular groan and thrust massively up from underneath me as he unloaded into me.

With that effort Chris soon drifted off to a deep sleep, leaving me quiet moments to think; always dangerous for me.

I was enjoying being Chris’s sex teacher; not just the sex – although he was proving to be a fast learner – but the privilege of it. The knowledge that I’d probably have a permanent place in his mind as the girl who’d claimed his virginity and left a happy memory in the process. That was a good thought, a positive one.

Less good was the deep regret I then felt about not having claimed Greg’s virginity and having been his sex teacher too. It was always there right in front of me; mine for the taking. But I didn’t. I just held it there, sometimes savouring it, often teasing it. A fear of losing his friendship held me back even as I satisfied my own need for intimacy by flaunting my sexuality in front of him.

Now it was gone. It was a disgusting thought. One I was ashamed of even at that moment. As I write this several months later at a time Karen has become such a close friend and I so much admire their relationship, I am even more ashamed, but it just goes to show the unsettling effect having Karen come along had on me.