That time I [f]ucked a virgin [m]edic

Wagwan wankers. Time for another tale of hobaggery that will hopefully warm your hearts and lubricate your respective genitalia. I’ve had this half-written pretty much since I last posted on here, but posting something else in r/sluttyconfessions got me feeling productive and I finally finished it.

This also involves me shagging a work colleague, but I promise I’m a professional 90% of the time. Also I’ll put in my standard warning about going off topic and the tense I use is all over the place.

A little description of me, since a few people didn’t like how vague I was last time. I’m a 5’4 brunette with C-cup boobs and, without meaning to sound full of myself, I’m told I’m abnormally hot. I’m Irish on my dad’s side, and Italian on my mum’s, which gives me a year-round tan despite my indoorsy ways. This story takes place when I was 23.

I’d started working in a lab the year before, and carved out a place for myself teaching our junior doctors some science. They’re generally pretty cool people, who despite being in their late 20’s/early 30’s tend to have a very laid back approach which I attribute to them having been students for most of their lives. This reflects itself in more ways than one, because every one of them I’ve ever met has looked at least 5 years younger than they actually are. Anyway, I’m rambling. The point is that they’re decent people, and my favourite of them was Matt.

Matt was 28, and your stereotypical nerdy Englishman. He wasn’t bad looking at all, and he had a wicked sense of humour, but he was fussy and introverted (sort of a Jon Richardson/David Mitchell/Charlie Brooker vibe). He and I shared a love of Peep Show, Futurama and many other tv shows that always left us with shitloads to talk about- something we did most nights, since we both tended to work until just before 20:00, well after everyone has gone home. Over time I developed a habit of slipping something flirty into conversation with him because I enjoyed how flustered he got.

I knew he was interested in me, courtesy of the other medics, but even though I’d thrown down some pretty unsubtle hints for him to ask me out, he’d never done it, and so I had to take matters into my own hands.

Anyway, one night when we were talking, he said something that struck me as odd. I was telling him about a Tinder date I’d had who had done this sucking thing when he kissed me, and how weird it was. When I asked him who his worst kisser had been, he dodged the question. This was the first time that I considered that he might have been a virgin.

It struck me as odd, because when I say he’s a nerd, I mean in the old-school sense, not the neckbeardy incel one. He’d been single since I knew him, but that was mostly because he was passionate about what he did, and spent hours at work. As a result he had no social life, and hence no girlfriend. I think all the other doctors there would have been single pringles too if they hadn’t met their respective other halves at university. He was decent looking, too. A little on the short side, but kind of cute, and with tousled hair that I felt compelled to run my fingers through every so often. So to consider that he’d never been kissed came as a surprise.

I decided to test the water over the coming days. I’d been planning on straight up asking him out, but truthfully the idea that he was a virgin had already planted the thought of a mercy shag in my head. Plus I’m a scoundrel anyway, and I enjoy teasing repressed guys.

I started talking about my sex life more, or lack thereof. I’d been single for a while at the time, and was getting to the point where I had to stop myself rubbing up against hard surfaces like a horny dog. Watching him try to conceal his interest was pretty adorable. The next day I made a point of showing him my thong when I asked whether the branding on women’s Calvin Klein underwear was the same as on men’s, which elicited a lot of very British mumbling as he stared.

On the next night we worked late, I asked him to check whether I had any heaves or thrills (a heart thingy doctors check for). He had to reach up under my shirt with a sweaty palm. The look on his face when he overshot and realised I wasn’t wearing a bra was priceless. I asked him if he’d ever touched a boob before, to which he replied yes, but only in a medical context. I locked eyes with him and said ‘this isn’t a medical context’. At that point his nerdy pedantry kicked in and he pointed out that it literally was, completely missing my not-at-all-subtle signal for him to fill his boots, and his hands. That pretty much sealed it in my mind. This guy was never going to make a move, so I would have to. Tomorrow.

I wasn’t supposed to be in work that day, but my boss had asked me to come in anyway. As a result, I decided I would wear what I liked, and if he complained he could get someone else to do his odd jobs. I spent the morning masturbating myself into a frenzy and removing every hair below my neck. I went into work wearing a tank top that was cut low at the sides, my best black bra and cut offs. It got a few looks at work, and when Matt saw it his eyes nearly fell out of his head. He kept stealing glances at it all afternoon.

Work began to empty out. First the other doctors, then the shift workers, and finally the cleaners came through. Eventually we got to the stage where I knew we’d be alone in our big office for the rest of the night. I wasted no time in pouncing on the opportunity to fuck with him again.

I started fidgeting with my bra strap and complaining about it being too tight. Then, as if it had just occurred to me, I turned to him and asked ‘Want to know how to take one off one-handed?’

I had to repeat the question a couple of times before he took it in, and when he understood what I was offering he nearly fell off his chair. ‘Isn’t that a bit personal?’

‘Well you basically fondled my boobs the other night,’ I teased ‘I don’t see how touching my back would be more personal.’ He stammered over himself in his rush to insist that it was an accident that night. I laughed at him for being so easy to troll, and reassured him that I didn’t mind. I said he should take this opportunity to learn, because it’ll impress a girl some day (FYI, it won’t. Bras can be tricky, but you aren’t picking a lock there fellas, it’s not rocket science).

I lift my tank top off, and try not to laugh at the way his eyes widen. They’re fighting a battle between being locked on my boobs and darting to the door every few seconds. He knows nobody is coming in, but I guess not everyone gets off on the chance of being caught like me. I found an excuse to show him bikini photos a few days ago, so it’s nothing he hasn’t seen before, but I presume it’s different when it’s underwear or something.

I turn my back to him and show him my unclasping tekkers, then he makes fun of me as I struggle to do it back up again. Next it’s his turn. I turn to face him, and when he complains that I’m making it harder I tell him to control himself (lol) and that when he actually does this, he’ll likely be kissing the girl. True to form, he completely misses the lingering eye contact I was giving him.

To be fair to him, he picked up how to unhook the bra pretty quickly, and averted his eyes like a gentleman when it slipped down a little. I think he was expecting me to put it back on, so he kept half looking back to see if I’d done it. I don’t know why I’m broken in such a way that awkwardness turns me on, but it does, so I drop my bra to the floor. He doesn’t notice at first, so I have to tug on his arm. ‘Matt.’ I say as I do so, inviting him to make eye contact.

His head nearly fell off when he looked back to me and saw me topless. My mum and her ex used to stay in a nudist colony when I was a teenager, so I’ve been comfortable with nudity for a while. It becomes kind of divorced from sexuality in a place like that, so even now it usually doesn’t turn me on, but seeing his eyes locked on my boobs as I stood there with my shoulders back and my head held high sent a thrill through my body.

‘I just saw your nipples get hard.’ He said, sounding a bit giddy.

‘I’m turned on.’ I replied, and at this stage it wasn’t an exaggeration.

I ask him if he wants to touch them. He asks if I’d mind (so polite), to which I reply that I’ve already told HR he’s done it, so he might as well get his money’s worth before he’s struck off. I think me joking around convinced him that I was okay with this, and he wasted no time in grabbing on. At this point I have to stifle a laugh, because that ‘bags of sand’ line from 40 year Old Virgin keeps popping into my head.

As he rubs my nipples I can hear his breathing getting heavier to match my own. Looking down I can see him pitching a serious tent in his jeans, but he seems oblivious till the moment I reach out and stroke my hand along the outline of his cock. His breath catches as I do so. There’s a wet patch on the front of his jeans from all the precum leaking out. I’ve never known a guy before or since get that much precum.

I step in close to him and kiss him. I’m quickly certain that he hasn’t done this before, because he spends the first thirty seconds with his mouth open either as wide as a hippo’s yawn, or as tight as a cat’s arsehole. Eventually he realises there is a middle ground, and by the time I flick my tongue over his to invite it into my mouth he’s doing pretty well. He’s a quick learner.

The sensation of his hard cock resting against my stomach is turning me on, and at this stage I realise how wet I am. I take one of his hands off my breast and drag it down my belly to the waist of my cutoffs. Our eyes meet for a second before I slide it under the waistband of my underwear and onto my v.

He explores it with his hands, spreading my wetness around. When he pushes a finger into me, the heel of his hand starts rubbing against my clit and I gasp loud enough to make me grateful nobody else is around. I grab onto his forearm with both hands and lean my head into his shoulder because for a second it feels like my legs are going to give way. Unfortunately, he misunderstands and think it’s his fingering that brought me to the edge. He starts doing it faster, and the moment passes. That’s fine though, tonight is about him not me.

I bring his hand out of my knickers and suck my wetness off his finger while looking at him with my best ‘come fuck me’ expression. I feel his cock twitch against me. Seeing someone so insanely turned on is only making me hornier. I drop to my knees and unbuckle his belt. We share a little laugh when I note that he’s wearing Calvins, and yes the branding is more or less the same. There’s a patch of his boxers that’s soaked in pre-cum right around the tip of his dick.

I pull his trousers and underwear down in one go, and his cock springs free. He’s circumcised, which is a new one for me. I decide I like it. I run my fingers along it, feeling how hard it is. I blow air on it, just to watch him squirm. Eventually, when I’ve had enough of teasing him, I bring the head of his cock to my lips. ‘Ready?’ I ask. All he could do in reply was nod.

I opened my mouth and took him in, feeling his cock run along my tongue. His precum tastes good- I’ve always liked the taste of it. As I’m taking in more of his cock his breathing is getting faster and faster. I’m nearly at the base when one of his pubes starts tickling my nose and I have to back out.

‘These need to be trimmed back.’ I say to him, tugging on the hair. ‘…if I’m going to be hanging out down here.’

‘This is going to be a regular thing?’ he says, looking earnestly hopeful.

‘If you want it to be.’ I reply, going back to sucking his dick.

I’m just getting into the rhythm of it when he starts pulling out. I ask him why, a little disappointed, to which he replied that he was about to cum, but he’d wanted to…

I catch his drift, and ask him how he wants to do it. He suggests it’ll be better if I go on top. I’m only too happy to oblige. He lies back on the carpet, shirt still on and pants around his ankles. It’s a weird sight, but I dread to think of how long it would take me to coax him into getting naked, even though I was about to be, and the smell of sex in the room would be unmistakeable if anyone walked in.

He’s looking at me strangely as I take off my shorts and underwear, and when I ask him why he tells me I’m beautiful. Such things make me go giddy anyway, but when delivered in a posh accent it’s enough to make me blush. Yes, nudity I’m fine with, but compliments make me squirm; I’m a complex woman.

I straddle him, his cock sitting in the crease of my v. Habitually, I rock back and fourth a couple of times to grind my clit on his shaft, but I can tell he’s got a hair trigger, so I don’t push my luck. His breathing gets faster and faster as I lift my hips and put his cock at the entrance to my pussy. I count him down from three ‘two…one… psyche!’ (I had to troll him once more). Just as he’s looking at me frustrated I sink down onto him, feeling his dick fill me up.

‘Oh fuck!’ he gasped- the only time I’ve heard him drop an F bomb.

I start moving up and down on his cock. I know it won’t take much, but I’m bringing my A game anyway. Slowly raising myself up his dick, clenching my pussy around it, then dropping back down onto him. I count the strokes- we made it to eighteen before his eyes glazed over and I felt his cock twitching. We stayed like that till he went soft.

I got dressed and went to pee/clean myself off, and he was still there on the floor, breathing heavily. Bless him, he’s not the fittest of men. I helped him up and gave him another kiss. He kept asking me if I was okay and thanking me, which was equal parts sweet and weird. He sent me about a million texts that night after I left- not because I regretted it, but because I was so horny I needed to go spend some quality time with my Hitachi.

We fucked on and off for the rest of his placement. By the end of it he was pretty good, but he moved to another city not long after and I got into a more serious relationship with my current bf.

Source: reddit.com/r/gonewildstories/comments/7yglpp/that_time_i_fucked_a_virgin_medic