Taking virginity of a nerd who was our IT support in college. He was the nicest guy I knew, with a huge dick!
It is nearly the end of my first year at university, and I am 20 years old. I am also two months pregnant, but at this point, nobody knows it except me. It hasn’t started to show.
Being primarily a music school, the college doesn’t have a big IT department. Computer support is provided by a small department of mostly middle-aged men, who have a habit of staring at your tits while you talk. For the most part, I keep well clear.
But they have an assistant, part-time – a computing PhD student from the science university next door. His name is Ben and he’s a first-year PhD, so around 22 – a couple of years older than me.
I’ve seen Ben a couple of times, helping people out in our computer room, and setting things up before lectures. He’s medium height, pale, slightly podgy, with bad geeky clothes. Nothing to make a girl look twice, in other words – a typical geek. But watching him help out over the year, I find I do look twice, and see a bit more than the geeky exterior.
When he helps people with their IT problems he is kind, patient and knowledgeable. He answers questions politely, without the condescending lectures of his colleagues, and when he smiles his face looks – for want of a better description – kind. Over the year he has helped me out a couple of times with minor problems, always solving them quickly, and despite his evident shyness, he is well-liked by everyone in my year.
A couple of weeks before the end of term I buy a gizmo for my laptop computer which will let me connect it to the keyboard I have in my room. That’s a music keyboard, not the computer type! I plug it in and try a few things to get it working but I quickly get stuck. It doesn’t seem to work. Out of ideas, I email IT support for help, and Ben replies. He suggests some changes and we email back and forward for a couple of days, but it still won’t work, and he asks when he can come over and take a look. We set a time for later that afternoon.
He arrives at my room at the agreed time, knocking on the door and shyly asking if he can come in. I show him the laptop and the keyboard, the cable and the gizmo I have bought. He sits down and quickly starts opening all sorts of complex settings screens and black boxes with little words, his fingers flying over the keyboard. I have no idea what he’s doing but skill, in any field is attractive, and he knows what he’s doing.
He asks me questions: how did I set it up, what changes have I tried? When he talks to me his eyes meet mine, shyly but steadily, without ever wandering below my neck. I find myself looking back into his eyes, seeing more in his slightly plump face than I’d noticed before. There is kindness there, and a clear glow of intelligence which combine into something more than the sum of their parts.
I find myself flirting very slightly, touching his hand when I show him something, standing a little closer – but he just gets on with the job.
He can’t fix it, it needs a different cable he says, before it will work. He writes down what I need to buy. ‘Let me know when you’ve bought it,’ he says ‘and I’ll come back and get it working for you.’
Suddenly not wanting him to leave, I remember I have another problem. For a few weeks whenever I click on a photo on my laptop, it doesn’t show the photo but instead a window full of gibberish writing. To see the photo I have to start ‘paint’ first then open it. I tell him and ask if he would mind fixing it while he’s there. ‘Oh that’s easy,’ he says, ‘your file associations are messed up.’ He clicks some things and changes some settings. ‘There, that should fix it. I’ll just check.’ He opens my ‘pictures’ folder and, before I can say anything, clicks on the first photo. It opens instantly, a full frontal nude I took that morning standing in front of my mirror, for sending to a school friend I’d been sexting with.
‘Oh god!’ He instantly closes the photo and blushes so deeply even his ears go red. ‘I’m so sorry, I should have asked first! I always ask! I’m sorry!’
I laugh, touching him on the shoulder. ‘Honestly don’t worry,’ I say, ‘not your fault.’ He is mortified though, and stammers more apologies as he stands up, still blushing deep red. ‘I’ll let you know when I’ve got that cable,’ I say.
‘Ok yeah,’ he says ‘it should just work, just plug it in, you won’t need me again.’
‘Ok well, I’ll let you know,’ I say. ‘Thanks for coming.’
‘No problem.’ He heads for the door. ‘And sorry again about…’ he hesitates.
‘Seeing my tits,’ I say, trying to make a joke of it. It doesn’t work, he blushes again.
‘Yeah,’ he says. ‘Bye then.’ He runs off down the hall.
Watching him leave, I find myself desperately wanting to see him again and to show somehow that I’m not angry or even that bothered about the photo he opened. That new cable, I decide, is not going to work!
A couple of days later I head into our common room after a lecture and he’s there drinking tea and reading. I sit down beside him.
‘Hi there,’ I say. Great opening line Jen, classic.
‘Hello,’ he smiles and blushes again slightly, but doesn’t look upset to see me.
‘That cable hasn’t arrived yet,’ I say, really nailing the small talk.
He nods. ‘I think it will do the job.’
Awkward silence. I can’t think of what to say. On the table in front of us is a chessboard. ‘Do you play chess?’ I ask.
‘Oh yes,’ he smiles. ‘I’m in the chess club’
‘Really? I was too, at school!’
‘I love chess. Do you have time to play?’ I smile – of course, I have time to play.
We play three games. He’s good, but so am I, and I beat him once. But the game isn’t as important as the opportunity to chat. With the distraction of the board between us absorbing any awkward silences, we chat about his PhD and his IT job, our schooldays, and our plans for the summer. Once he overcomes his shyness he’s easy to talk to, funny, attentive – and again showing that fierce glow of intelligence which I’d seen in my room.
After an hour or so I had to go to another lecture, so we said goodbye, far less awkward now. I walked from the room with the happy feeling of having put things right, and the glow which comes from having made a friend.
A week goes by, and it’s just days from the end of term. Finally, in my pigeonhole, there is a parcel; it’s the cable for the keyboard. I feel suddenly excited – if the cable doesn’t work (or maybe even if it does), this is another chance to see Ben. Already I am starting to feel that I want to be more than just his friend.
In the end, no subterfuge is needed. I plug in the new cable and it still doesn’t work. Time to get some IT support! I email Ben and tell him, and he offers to come and help later that afternoon.
Before he comes I ask myself what I’m doing. Am I going to try to seduce him? Surely not! I want to know him better, maybe much better, but it’s not his body I want. I tell myself this as I put on a slightly more revealing dress, choosing a bra which gives me some nice cleavage. Nothing, I decide, spraying myself with perfume, is going to happen.
He arrives on time, wearing the same shapeless T-shirt as before. I open the door in my pretty summer dress, padded push-up bra and low neckline making my tits look amazing. He doesn’t even glance at them, keeping his eyes firmly fixed on my face as we say hello. Either he’s far more disciplined than most guys or, I suddenly think, maybe gay.
‘Let’s have a look then,’ he says, sadly referring to the computer rather than the contents of my dress. Now he’s in the room I admit it to myself; I do want to seduce him, suddenly I want it very much indeed. I like him a lot, and I want to touch him and have him touch me back. The trouble is, I’m not sure how to even start.
Though I’ve slept when plenty of men over the year, they have all, to some extent, pursued me. This guy is different. Even if he does fancy me, and I may not, he’s never going to make a move. I’m going to have to do the chasing for once, and it’s not going to be easy. Play this wrong, I tell myself, and he’s going to run a mile.
It doesn’t help that he fixes my computer in less than a minute. With a few clicks, the music program starts working, showing the keys from the keyboard as they are played. Fuck – I think – he’s going to leave. Wondering how to keep him in the room, I sit on the stool at the keyboard and play a few bars of the exam piece I have been preparing, to test the connection to the laptop.
‘I love Rachmaninov,’ he says, to my considerable surprise. My exam piece was Rachmaninov’s Rhapsody on a Theme by Paganini, and I played a tiny part in the middle.
‘I didn’t have you down as a classical music guy,’ I said, ‘I thought you’d be more into metal or something.’
‘Oh I like that too, I love all music. It’s partly why I applied to do IT support here instead of at my college. But that piece is one of my favourites, you can understand why it’s so popular.’
‘Yeah,’ I agree, I love it. ‘It’s a bitch to play though. I’m doing it as a first-year set piece.’
‘Is there a solo piano arrangement of the whole thing then?’ He asks.
‘No, just two of the variations in the middle.’ I play a couple more bars. ‘That one, and this one…’ I play a bit more, showing off a tricky bit, and make a couple of fingering mistakes. ‘And I need more practice!’
‘No, it sounds great.’ He sounds like he means it.
‘It sounds better on a proper piano than a crappy electric keyboard.’
‘I’d love to hear you play it,’ he says, and immediately blushes red. I swivel on the stool to face him. It’s the first time he’s shown the slightest sign he might be interested in seeing more of me, and the blush tells me, perhaps he’s more interested than he seems.
We talk more about music. Again, given a subject where he feels comfortable, he’s engaging and hugely knowledgeable, showing a wide range of musical tastes. The more he talks, the more I want to put my mouth on his! As we chat, his eyes still haven’t wandered from my face, even though I am sitting on a stool, a little higher than the desk chair he’s on, and leaning towards him, my elbows on my knees. Fuck, I’m straight and I’d look down at a girl’s top if she sat facing me like that!!
Is he a strict gentleman, or just not interested? I set him a little test, by pretending to sneeze, then leaning down and to my left to get a tissue from the drawer. This has two purposes. Leaning further over will give him a surely irresistible view right down my top, and looking into the drawer means I won’t be able to see where he’s looking. Except of course, as every girl knows (and no guys ever seem to realise) we don’t have to be looking at you directly to know when you’re looking at our tits!
I bend down and open the drawer, he looks down my top. Bingo.
I straighten up and smile at him as I pretend to blow my nose. Fuck it, I think, I could send this guy signals all day and he’ll still never make a move. I’m going to have to just go for it, shove my neck out and hope I don’t crash and burn. Here goes nothing…
‘Can I ask you something?’ I say. I can feel myself blushing – it’s catching!
‘Sure,’ he nods.
‘Do you have a girlfriend?’
‘Oh,’ he blushes too, I knew he would. ‘No, I haven’t.’ He laughs nervously. ‘Computer geeks aren’t allowed, girlfriends.’
‘That’s good,’ I say. Am I going to do this… come on Jen, no turning back now. We’re facing each other, me on the stool, him on my desk chair, our knees a couple of inches apart. I lean forward and take one of his hands which is resting on his knee. ‘That’s good,’ I say again, stupidly. I had some cheesy lines prepared like ‘cos if you had I’d get into trouble when I kiss you’ but it sounds stupid. So I just lean forward and kiss him once, gently on the lips.
He responds to the kiss, his lips moving against mine. I keep my head close to his, our lips still almost touching. There is a moment of stillness, his breath warm on my lips. I move my head back slightly, my eyes meeting his. He looks surprised, but he’s not blushing for once. His gaze holds mine. ‘I like you,’ I say, quietly. ‘Sorry to jump on you like that. I just…’ I run out of words ‘…wanted to,’ I finish, feeling foolish.
‘Don’t be sorry,’ he says. I’m still leaning over him, awkwardly still half on my chair. I stand and pull my stool closer to his, so when I sit our knees are interlocking. ‘I like you too.’ I stroke his fingers as we lean forward together, meeting in the middle this time, holding his gaze into another kiss.
He kisses gently, responding to the movement of my lips, not using his tongue until I use mine, and then only slightly, the tips of our tongues just brushing together.
We kiss for several minutes, gentle but extremely sensual, gradually moving closer together. I stand and move onto his knee, my legs on either side of his and my arms around his neck as we kiss some more. He holds me on his knee, one hand on my back, but makes no other move to touch me. His hand is warm through the material of my dress.
I know I want this to go further, a lot further, but I don’t want to rush. The kissing is so good, I never want it to stop, and for maybe 10 minutes more it doesn’t. Not since school have I kissed somebody for so long, in a private place, without them being in a rush to remove my clothes. Ben does not attempt to do this at all, his other hand just rests gently on my leg as we kiss and kiss, until my whole body is tingling with sexual desire.
After a while we pause, our faces still close together. ‘Can I ask you something personal?’ I ask.
‘I think so,’ he says, smiling.
‘After you saw that picture of me, the naked one. Did you think about it later? When you were masturbating, I mean – did you picture me?’ He blushes deeper red than he did when he saw the photo! I know the answer is yes. ‘It’s ok,’ I say ‘It would be a bit disappointing if you’d seen me naked and just forgotten about it!
‘You looked amazing in that photo,’ he says, sounding almost sad.
‘Do you want to see the real thing?’ I ask. My heart is beating very fast. He nods, silently. The dress has no zip; I slip it off my shoulders and push it down over my boobs, then reach behind and unhook my bra. I take it off, moving it behind his head as I take my arms out of the straps.
Topless now, I look into his eyes. They stay on mine, still shy, or still polite. ‘It’s ok,’ I say ‘you’re allowed to look.’ I sit up slightly straighter on his knee and finally, his eyes drop to my tits, staring at them, his mouth slightly open. I lean forward, bringing one of my nipples towards his mouth, and he hesitates slightly before leaning forward and kissing it, making me gasp with pleasure.
Leaning down, I kiss him some more, more passionate now, our mutual desire more evident. ‘I think we’d better move to the bed,’ I said.
I stand up from his knee, and he stands too, rubbing his legs. ‘Sorry,’ I said, ‘did I make your legs go to sleep?’
‘It was worth it,’ he says, and I kiss him again, standing face to face, realising that standing I’m slightly taller than him. Holding his hand, I sit down on the bed. He hesitates.
‘Jenny,’ he says, sounding suddenly diffident. I look up at him. He stumbles over the words. ‘It’s just, I should say, I mean… I should tell you… I’ve never done this before.’
I stand, my face close to his, our hands still together. ‘Really, never?’ I ask.
‘No,’ he says, ‘I know it’s embarrassing.’
‘It’s ok,’ I stroke his face, ‘I don’t mind, I mean, we don’t have to do anything if you don’t want to.’
‘Oh no, I want to!’ He says with feeling. ‘I just wanted you to know, I don’t know what I’m doing, really.’
I kiss him some more. ‘You’re a very good kisser for a virgin.’ I say. Might as well get the V-word out there rather than let it hang in the air.
‘I’ve kissed girls before. Well, one girl. I had a girlfriend when I was at school but we only kissed.’
‘She taught you well,’ I said. I pull my dress, still hanging around my waist, off over my head.
‘Let me teach you the rest,’ I say cheesily, as I pull him down onto the bed.
We lie facing each other, kissing, my hands exploring his back, under his shirt. He rests his hand on the bed between us. ‘Touch my tits,’ I whisper, rolling onto my back. He moves his hand up my body, from my hip, up my side and finally onto my breasts, sliding his fingertips over them and brushing gently over my nipples. I pull him closer to kiss again, my hand pulling his t-shirt up and over his head. He sits up quickly to pull it off. ‘Lie down,’ I tell him ‘Lie on your back.’
He does what he’s told, and I straddle him, cowgirl position, my pants against his jeans. I lean all the way forward, my nipples against his bare chest as we kiss. Rocking my hips against him, I can feel real hardness through his jeans, pushing against my pants. Grinding against it, I feel the steady pulses of pleasure each time the hard bulge presses against my clit.
I slide back down his legs. The bulge in his jeans is impressive, and I decide it’s time to see what’s underneath. His jeans have a button and a zipper fly; I undo them and pull the jeans down to his knees, emitting as I do a genuine gasp of surprise.
His erection is sticking out through the fly of his boxer shorts, and it is huge! It has to be 9″ long, and thick like a truncheon. I’ve slept with quite a few guys, with penises ranging from tiny to very large, but this was (and remains) by far the biggest I’ve ever seen. Even in porn, I have never seen one like it.
I realise I am just sitting there, open-mouthed staring at it. ‘Are you ok,’ he says, grinning. He might be a virgin but he’s not an idiot, he knows it’s huge!
‘Fuck me Ben, you’re telling me you’ve been walking around with that in your pants for 22 years and you’ve never used it?’
He smiles. ‘At primary school, they used to call me donkey dick.’ For the first time, he sounds almost arrogant, though still very sweet.
I pull off his boxers, which is tricky on account of the scaffolding pole sticking out the middle and bend over his crotch. ‘I’d better take a closer look,’ I say.
I slide my hand up its length; my fingers don’t meet around it. Bringing it to my mouth, I slide my tongue over the tip, opening my mouth wide to take it inside. Despite the size, it is rock hard, and spotlessly clean. He moans softly as I slide my tongue across the underside of the tip, but it’s too big to keep comfortably in my mouth, so I lift my head, and move up to lie beside him, my hand still around his amazing cock.
‘Ben,’ I say, kissing him, ‘that is a fucking amazing penis.’ We kiss my hand on his cock, stroking him, my leg hooked over him. ‘Touch me,’ I said, taking his hand and guiding it down between my legs. He strokes along the line of my pants, even through the material it makes me gasp.
‘You’ll have to show me, I’ve never done this before,’ he says simply. I nod.
‘Ok.’ I roll onto my back and lift my hips to take off my pants. I kick them off, then pull him towards me, feeling the warmth of his body.
I take his hand and guide it. ‘I’m sure you’ve seen porn…’
‘Yeah but it’s not realistic is it,’ he says, reasonably.
‘Depends,’ I say. ‘Ok, start with two fingers, here,’ I guide two of his fingers between my lips, into the entrance of my vagina. I am ridiculously wet, after 20-odd minutes of kissing, and his fingers slide in easily. ‘Now slide up like this,’ I say breathlessly, guiding his fingers, wet from my vagina, up and onto my clit. ‘You feel the lump of my clit,’ I slide his fingers over it, breathing in sharply with pleasure as I show him where to touch it.
‘Use those two fingers together, a little more pressure, that’s it. Rub them over my clit, both fingers, so I feel the bump between them.’ He’s picking it up fast and I’m breathless, giving gasping moans between instructions. I take my hand away and wrap it back around his cock. ‘Slide them down to get some more wetness, then back to where you were… a little higher, feel for the lump, oh god yes…’
He kisses me, and I stroke his cock, his fingers doing exactly as I told him – and I’m breathing very hard now. ‘Just keep going like that, once I get close keeping the rhythm is important, a little faster, a little more pressure – yes oh god don’t stop, keep doing that. You’re going to make me come.’ I writhe as I get close to the edge, feeling his cock in my hand, my head arched back, I lift my hips but he keeps his fingers in the right place, sliding over my clit and I cry out loudly as I come, grasping at his back as the orgasm floods out through my body.
I grab his hand, moving it away from my post-orgasm-sensitive clit. ‘Sorry!’ He says.
‘God, no,’ I say, still breathing hard. ‘That was so good! It’s just sensitive right after.’ I kiss him.
‘Talented fingers’ I say.
‘Doesn’t seem so difficult,’ he grins.
‘Trust me, there are many, many men who have never made a girl orgasm like that. It’s harder than it looks.’ We kiss as my sensitivity passes, my hand gently stroking his cock. ‘I think it’s time we did something about this virginity thing,’ I said.
He smiles, then frowns. ‘I don’t have any condoms. I mean, I never thought…’
‘It’s ok, I’ve got some.’ I roll over and reach into my bedside drawer, pleased that from where he’s lying he can’t see the collection of condoms, sex toys and lube which live there.
I unwrap a condom and try to roll it down his cock, but it is immediately clear it’s far too small, it won’t go on, not even close. ‘I always thought ‘large’ condoms were just for self-deluding men,’ I said ‘but this isn’t going to go on.’ He tries himself, but it’s not happening.
‘Sorry,’ he says. ‘I’ve never tried to put one on before.’
I make a quick decision. ‘Look,’ I say, sliding my hand over his chest. ‘I’m already,’ I bite off the word ‘pregnant’, suddenly thinking that this is not the moment to reveal that. ‘I’m already protected,’ I improvised at the last moment. ‘If you trust me, we can do it without.’
‘I trust you,’ he says simply.
I lie on my back, kissing him as he moves on top of me. His hard cock presses against me, and I reach down to guide it with my hand.
He tries to push forward, the tip of his cock between the lips of my pussy, but his angle is all wrong. I use my hand, trying to guide him, but his size and inexperience together make it impossible, I just can’t get him to the right position. He grunts in frustration.
‘Ok, let’s try something else,’ I say. ‘Lie on your back.’ He lies back, the huge shaft of his erection sticking up and away from his stomach. I climb onto the top, cowgirl position, and take it in my hands.
Though I’ve never had a penis this big, I have over the years, experimented with large objects. Wanting to know what it would feel like, I purchased the fattest cucumbers the market would sell, and quietly used them to while away an afternoon. I’ve purchased implausibly large dildos from Ann Summers and tried them out; I know that, if I get the angle right, he’ll fit.
I lift myself onto my knees and lean forward, lining up his cock with the entrance of my vagina. Feeling him in the right place I slide gently down, gasping in pleasure as he fills me. Despite the big toys, this probably is the biggest thing I’ve ever had inside me, and god it feels good.
Once he’s fully in, I start to rock slowly up and down, feeling him inside me and watching his face, his eyes still on mine. I slide my hands over my breasts. ‘Look at my body,’ I say ‘It turns me on when you look.’ I rock faster, lifting myself slightly with each forward movement, sliding my cunt up and down his cock. He moans softly with each movement. I reach for his hands and bring them up to my breasts. ‘Stroke my nipples,’ I say, as he starts to moan louder.
I move a little quicker as he slides his hands over my breasts, feeling my pleasure start to build. He moves his hands to my hips and starts thrusting upwards meeting my movements, gently at first then more firmly, pulling me down onto him then lifting me, taking long strokes inside me.
I lean forward, moving with him as his hands move to my bum, gripping it with his fingers he moans loudly, thrusting up into me I feel his cock pulsing, his eyes half closed as he cums inside me.
I hold still as his orgasm passes, then lean down to kiss him. We kiss passionately, tongues sliding over each other. I roll off him sideways, feeling his cum run down my leg as I lift off his cock. Lying beside him, we kiss some more.
‘So,’ I say after a while. ‘Was that what you were imagining after you saw my photo?’
‘Kind of, yeah.’ He smiles.
‘Only kind of?’
‘Yeah well, I imagined doing something to you with, hmm, with my tongue.’ He looks sheepish.
‘Ahh, I see. Well now you know your way around down there, perhaps you should live out your fantasy…’
‘Ok.’ He starts to move down the bed.
‘Wait,’ I say, ‘do you want me to clean up, there’s lots of your cum down there.’
‘I don’t mind,’ he says simply, and I wonder where we’ll get married, and how many children we’ll have.
When I opened my legs, he moves between them and slides his hands up my thighs, looking at my pussy. I love being looked at.
Moving my lips apart with my fingers, I expose my clit. ‘Lick me here,’ I say ‘in a steady rhythm, just like before.’ He slides his tongue along my labia and onto my clit, and I moan from the simple, delicious pleasure of oral sex.
My head back and my eyes closed, I rest my hand on his head as he licks me. My intakes of breath make shallow moans, which get louder and deeper as the pleasure builds. I play with my nipples with my other hand, wanting him to do it but not wanting to distract him as he pushes me closer to orgasm.
Suddenly, he stops and lifts his head; I’m close to orgasm and I’m about to tell him to keep going, but stop myself as he sits up between my legs, his cock rock hard again.
He moves towards me, his hands on my knees. ‘I’m going to get this right’, he says, moving up between my legs.
‘Here,’ I grab a pillow and put it under my bum. ‘That will help. Stay sitting up like that, so you can see what you’re doing.’
Holding his cock in his hand, he pushes it down, the head sliding over my clit and down to the entrance of my vagina. He pushes forward, almost at the right angle this time. I lift my hips, rocking them back slightly, he pushes again and sides in quickly, making me cry out in pleasure and delight.
He leans forward over me. ‘Fuck me,’ I say. ‘I’m close. Fuck me.’ He thrusts inside me, slowly at first then quicker, his hands on the bed on either side of my head. I rock my hips up to meet his thrusts, crying out with each one, waves of pleasure building up inside me.
I grab his bum and pull him hard into me, again and then again, crying out as I come, my hands gripping fingertip bruises into his bum as I have a huge vaginal orgasm.
Gasping for breath, I wrap my arms around him and pull him to me, kissing urgently. He is still rock hard inside me but I’m too sensitive now to move. He sits back and pulls out, moving gently as the sensitivity makes me gasp.
I sit up and move around him, pushing him down onto his back, and put his huge cock straight into my mouth. It’s difficult but I keep the tip in my mouth, sliding my tongue over the underside and holding the shaft in my hand. He moans softly and cums, spurting into my mouth, his hardness surging with each spurt. I swallow, holding his cock in my mouth as it finally starts to go soft.
We lie together, our breath returning to normal. ‘Well,’ he says ‘I wasn’t expecting that.’
‘You know what Ben,’ I said, looking at his cock, flaccid now but still impressive. ‘Neither was I!’