Kate: Breaking in a virgin

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Status: Finished  |  Genre: General Erotica  |  House: Booksiesilk Classic Group

Kate finds she's got herself a virgin. There's more than one way to get herself laid.

I’m not sure what it was made me turn my head. It wasn’t a sound, not even a movement caught out of the corner of my eye. More an instinct.

One minute I’m talking to Greg and his new girlfriend at what I suppose you’d call a beach party organised by some of our mutual friends to celebrate us all being back in town for the summer break. I’m still getting used to the idea of this girl of Greg’s let alone to the fact I know he’s rooting her silly every chance he gets.

She’s nice enough and we were quickly becoming good friends, but selfish and insecure as it makes me seem, I just wished she wasn’t as drop dead gorgeous in that cutesy sort of way. I might not have any claim on him. But seeing Greg fall so heavily for a girl had been shattering; more so when the overt sexuality on display with the perpetual camel toe in her bikini pants and nips pushing out of the small triangles of her top reminded me so vividly of what they’re getting up to in all the beach hiding spots Greg and I have grown up playing in.

But whatever it was that made me turn my head, the next minute my eyes are transfixed by the sight of this guy joining the far side of our party’s circle of friends. If this was your typical bodice ripper romance novel I’d be talking of love at first sight across a crowded room. But it’s not. And it’s not so much that I don’t believe in love as I’m chronically incapable of falling into it. Indeed, I run away from it.

Still, in that moment I decided this guy and I are going to end up in bed together. Even though I’m on the far side of the crowed group from where this guy is entering, his eyes met mine and they all locked together. Whatever effect he was having on me it seemed to be mutual.

He wasn’t a local; rather it looked like he’d been dragged into our party by John, one of our friends.

He was clearly fresh out of the surf, his wet boardies clinging in a way that left nothing to the imagination.

Ah, yes. Squared jawed, nice body. Tall. Good muscle definition without overdoing it; surfer not body builder. His resting face seemed to be a nice smile; as if the world shone upon him. After our initial tussle for Greg’s affections, Karen and I had only bonded a week ago, but already she had been bold enough to label my choice of men Neanderthals. Personally I always imagined Neanderthals with an excess of body hair. But if a Neanderthal was given a full body wax and a good bit of grooming, then OK, maybe that’s what one might look like.

The next half an hour is remembered as a bit of a blur. All I can really recall is that he somehow made a beeline across the group to me, John introduced Chris as someone at his Uni, and that moments later Chris I have somehow cast off John, Greg and Karen and are now engrossed in each other’s conversation. Shortly after that we’ve got our arms wrapped around each other passionately kissing as we sway to the music permeating our senses to the exclusion of the hub bub of the party conversation.

Maybe it was at that point I should have picked up some hint that this guy was different from my usual Neanderthal pick up.  As we’re dancing – if you could call our amorous swaying that – the lower part of his body is separated from mine. Most guys by now would have their thigh between my legs.

Instinctively my hand slid down towards the curve of his lower back, a gradually increasing pressure drawing his stomach and hips towards mine. As the still damp material of his boardies first made contact with the bare flesh of my stomach just above the waist hem of my bikini pants a strange sense of satisfaction accompanied the discovery they contained the hard shaft of an erection.

Again it’s now a bit of a blur how we escaped the party and ended up back at the two bedroom holiday unit he was sharing with a mate; one who was fortunately absent. If you think all this blurring of memory is somehow caused by too many party beverages, you’re wrong. I was on my first glass of wine when he walked in and our lips hadn’t been separated long enough to drink anything more than that since. If I was intoxicated, it wasn’t by drink.

While still unusually entranced by the power this guy’s presence is having over me, it’s about now I really started to realise the script of this encounter isn’t going entirely to the normal pattern. We were doing little more than pashing for nearly an hour at the party. By the end I had my crutch pleasurably rubbing against his thigh and his erection pushing deeply into the flesh of my stomach and mons. I would have said we were both on heat.

Maybe the immediacy of our passions might have subsided just a little during the five minutes it took to get back to his place.  But we’d been in the unit for another fifteen minutes and by that time he’d offered me a drink and guided us both the a lounge chair where we were sitting in close contact while he had an arm around my shoulders and engaged me in conversation.

I didn’t want to look like a complete slut. I was waiting for him to make the first move; my most provocative action at this point being the hand I had on his thigh high enough to be brushing against one of his balls and the fact one of my nipples was seriously in danger of sliding out of the bikini top I was wearing.

With any other guy I would have been getting the “I really want to stick my dick in you now” signal and be lucky if the beach wrap still around my hips wasn’t on the floor and any of the strings on the string tie bikini I was wearing still had a knot in it. And yet this guy is just talking. Nice. Entertaining. Even seductive. Maybe it’s the way romance is meant to be conducted. Just not what I was used to.

I decide to step it up just a little and bend around and start kissing him again. He received my tongue into his mouth willingly; the arm furthest from me wrapping itself around my back, the hand slipping along the line of the lower tie of my bikini top.

Looking down I could see the top of his erection struggling to escape from his boardies. Nothing is actually visible, but the waist band is starting to be pulled away from his stomach as it fights to retain the shaft now clearly outlined within the thin clingy material. My other hand is on the far side of his waist, the forearm pressed against his stomach passing teasingly close to the tip of his erection.

Ten minutes later and we’re still just kissing. Completely enjoyable. I’m fully on heat again. Half the width of the bell at the top of his shaft now can be seen down the front of his pants as my eyes twist themselves to look down. I can even see some drips of pre-cum oozing out of the now visible hole at the top. But nothing’s happening. Once or twice the hand around my back slides under the tie string of my bikini top and I even think he might undo the knot. But no. I’m still fully dressed; nothing truly erogenous so much as touched. It’s all there ready; engorged, open, throbbing, wet and waiting. But nothing.

I slide my hand down the front of his pants, the back of my fingers firmly in contact with the length of his shaft. The middle finger is slimed as his pre-cum wipes against it as I slide it down. At last he bring his hand around and slips it inside my bikini top; quickly finding the nipple; hardly surprising since it was now big and hard enough you could have found it in the dark with a blindfold and wearing welders gloves. He rubs it gently between two fingers with a nice technique.

By angling his hand out he uncovers most of the breast; pushing the triangle of the bikini aside.

At last he seems to have taken the hint as I feel the strings of my bikini top being pulled by the hand he originally had around my shoulders until the one playing with the nipple flicks it deftly away to let it fall down onto the chair.

Breaking free of our kissing, he buries himself in my bosom and licks and sucks both nipples, leaving me staring at the top of his mop of blonde, surf bleached hair as I enjoy the arousing effect of his oral games with them.

Then we’re back kissing again, his fingers again on my nipples.

This is all quite nice. Indeed his nipple play is so nice I even wonder if you can have a nipple orgasm. But again we’re stalled at that.

My hand had been stroking up and down on his stomach and pubis; playing with his pubic hair and in the process the back of my fingers had been stimulating his shaft. It was rock hard, surging a little and the top was becoming slippery with his pre-cum. I realised I needed to take the lead again, so turned my hand around and grabbed his shaft, slid up to the tip of it, pulled my hand out, undid the draw string of his pants, pulled the waist wide open and exposed him.

Then I wrapped my fingers around it again, stimulating it up and down.

At last he seemed to realise this is meant to be full on. He undid the side knot on my wrap and pulled it away from me to throw on the floor, then his fingers pushed in against the already damp crutch of my bikini bottoms, sliding the length of the valley he created; loitering momentarily to feel my opening before moving up to play up and down against my clit.

Finally he slid his hand over the top of the waist band and down into my pants, quickly finding direct contact with my clit and expertly fingering it. Unlike most guys he concentrated more on my clit instead of wanting to just penetrate me with his fingers; only penetrating me occasionally to slime up his fingers for better lubrication. It felt great.

It was time for the question. “Do you have a condom?”

He answered rather nervously and hesitatingly - “Eh, no I don’t. Do you?”

Of course I did.

My bag was on the table just out of reach, so I had to get off him to get to it. I turned back to where he was sprawled out on the couch. He’s sitting there waiting for me; arms along the back of the couch, pants pulled down at the front to expose what I could now see was an impressive erection.

I’m all for being comfortable for sex and the couch wasn’t it. I took his hand as I stood above him and pulled him upright. “Which is your room?”

He pointed to the nearest door, so I led him towards it, stopping momentarily to let him shake his pants off his ankles after they had slid down his legs. Then I threw him face up on the bed. As I joined him on it, I took a moment to study his shaft. It looked like a big one, visually maybe helped by the fact he was circumcised. More importantly from my point of view – even if we were using a condom – it looked clean.

We’d had enough fooling around. I straddled him, lifted his shaft up and rolled the condom over it. I was about to bring myself down on it when I remembered I still had my pants on, so quickly pulled the side ties and discarded them. At last the moment had come as I again brought my hips above it and sunk myself down on it.

But something didn’t feel right. I was going down, but he wasn’t going in and when it did penetrate me a little, it was anything but hard. The hand holding it vertical was quickly just left wrapped around a floppy shadow of the erection that had been there a moment ago.

I’d had my suspicions before this moment. Now I thought they were confirmed. The next few moments were going to be delicate. I bent down and kissed him as I breathed the sensitive question into his mouth. “Are you a virgin?”

The truth is I’d seen this before. I’m not going to say I’ve broken in dozens of virgins. I’m not that much of a slut. But I’ve been with at least two that I know of, both of whom have in one way or another done this. And those previous experiences left me with a determination to deal with the issue directly.

Guys don’t like to admit they’re virgins; especially not while there’s a naked girl sitting on top of them. A girl might volunteer “be gentle, I’m a virgin”; a guy will volunteer nothing and try to bluff through. But that puts enormous pressure on them – the very thing that causes this problem. But if you ask them outright, that’s a different matter and merely admitting the truth and asking for understanding from the right girl relieves the pressure.

I could see him blushing. Sheepishly he answered. “Yes”

In my mind, the mental picture I’d had of the afternoon and night that lay ahead of me had just changed. There wasn’t likely to be any head banging, body breaking, wild, multiple-orgasmic sex with the Neanderthal body under me. But that was OK. The past had shown that to be a hopelessly optimistic scenario anyway. In this case I just needed to flip to plan B.

I’m sure there’s a medical name for this but it’s probably latin and neither of us would understand it anyway. I just call it anxiety collapse. Whatever the cause, that and prematurity are the hallmarks of the inexperienced. We all have to start somewhere. I liked this guy and he clearly had a strong effect on me. If he was willing, I had already decided to make the best of the situation.

As to why a guy this good looking and apparently nice was still a virgin, that’s another matter. Maybe he was really shy, maybe he had religious reservations, maybe he was a mother’s boy. But look at Greg. Until a few weeks ago he was a virgin and that said nothing bad about him. As the start of this story probably showed, in some ways at that time I still wished he was.

“That’s OK, we’ll just take it slowly. I promise that by the time I finish with you, you won’t be one any more. Is that OK?”

He smiled. “Yes”

From talking afterwards to the previous guys I suspect this sort of anxiety collapse is caused by a couple of things; most of which, other that some sort of religious or upbringing guilt, come down to performance anxiety.

And surprisingly with these guys – especially the nice ones – it’s a concern about making it through to satisfying a girl that can top that list. After all fear of being premature is in part a subset of that. And then there’s their fear of just ‘doing it wrong’. So my view is I sort of  nicely take control so they don’t worry about ‘getting it right’ and give myself or get them to give me a climax before trying for penetration for them.

It’s clear this guy knew how to finger a girl, so that was one possibility for my orgasm. I suppose him giving me oral was too; although that also puts performance pressure on him and in any case I’m no more keen on getting oral than giving it; something for rare occasions but not high on my hit parade. After all when they’re down there that mop of hair which is all you can see could just as easily belong to a weakling, pimply faced computer nerd, a girl, a pet Labrador or a Japanese companion robot with enhanced software as the hunk you’ve invited into bed with you. It sort of lacks that body heat experience that good sex is supposed to be all about.

No, with Chris I applied my preferred approach of straddling him and rubbing my clit up and down on whatever amount of cock was there for the purpose. Sure, at first it was soft and just sort of swayed back and forwards with my movement; but still it was more than doing the job for me even in that phase.

Once I got myself going I asked Chris to play with my nipples; something he was happy to apply himself too – using his fingers on one and his tongue on the other.  

And predictably, now the pressure was off him and he had his head buried against my breast, it wasn’t long before it grew itself hard again; making it much better than any dildo or vibrator I can think of.

The trick was, when it went hard, not to get ambitious and stick it in. Just finish my climax.

The only issue was the difficulty of using a condom while doing it. Essentially you couldn’t. No condom will stay on a flaccid cock flopping around while I rub my clit on it. When it got hard I might have been able to stop and put the condom on, but there was a good chance the condom would have been ripped apart by my frantic clit rubbing action anyway.

While there was a small risk, I figured he was a virgin and I was pretty sure I was clean, so it was worth it.

And in terms of the climax, it was definitely worth it. For me it was a beauty; something I was more than happy to communicate to Chris by ramping up both the sounds I made and my body’s physical reaction. It was all real; just exaggerated a smidgen.

Then I lay down on top of him, pressed my clit hard against his shaft and passionately kissed him until I squeezed every last contraction of pleasure out of it and him.

Finally, keeping as much body contact with him as I could, I slipped a hand down between us, put the condom back on him and guided him to my entrance. And so, for the second time that afternoon, I bore down on him to try to push him inside me.

With some relief I felt the hardness of his shaft separate the folds of my crutch and slowly enter my body; slipping easily into my well lubricated vagina. Deeper I pushed him until the collision of my mons against his pubis meant it could go no further. Judging from where I could feel him I figured we still had the full monty.

This guy seemed to like kissing, so I kept kissing him as I started to move up and down against him, withdrawing him from my body and pushing him back in again. If he was going to go early, I wanted him to get some experience of thrusting before he went; for him to be able to feel he wasn’t a virgin any more.

For maybe a minute we kept that up.  He wasn’t the only one enjoying it, so I started to figure – let’s go for a second one.

Breaking away from his mouth I angled my body up over him to bring my clit into contact with him; lifting his face against a breast with my hand as I did that. Then I started really working against him.

It was more than he could take. Within a few thrusts he let out this most incredible groan as I felt his body almost convulsively thrust against me. With his hands on my butt, once, twice he thrust himself as deeply into me as was humanly possible until with the second one he screwed his hips around to the accompaniment of a long moaning sigh. Then he went limp under me.

I lay back down on him, waited until he’d completely finished recovering from his orgasm, kissed him and whispered into his ear “congratulations; you’re not a virgin any more.”


Submitted: February 17, 2015

© Copyright 2023 joanmcarthy. All rights reserved.

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Add Your Comments:



Congratulations. This is a most original and best short story because of it's originality. Usually the virgin is the other gender but you have put together all the emotional thought and actions that is of the male sex. Finishing with the so very real realisation "Oh how Glad I am to no longer be a virgin".
You write so explicitly true to life.

Tue, February 17th, 2015 6:49am


Thanks again Skypilot. Nice to see you're still reading

Mon, February 16th, 2015 11:31pm


Well written Joan. It reminds me of one of my first experiences with a young woman by the name of Karen.

Wed, February 18th, 2015 6:09pm


We've probably all been on one side or the other of that

Wed, February 18th, 2015 11:52am

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