Dirty Carolyn

Ah, Dirty Carolyn. Big tits, red hair, and a penchant for dressing in stylish vintage clothing. She looked like a porn star – in the best possible way – and she fucked like one too.

Ironically, given how things eventuated with us, she gave me the absolute brush-off the first time we met. She was a friend of my sisters' who I was meeting for after work drinks one Friday. A few of my friends came along and so did a few of hers, Carolyn among them. Carolyn is the kind of girl that stands out in the bar, the girl that every guy sneaks a look at when he thinks his girlfriend isn't looking. I took one look and placed her firmly in the 'out of my league' category. Although gorgeous, she had a prudish/ stand-offish vibe about her and shut down any guy who tried to engage her in conversation. That night went as expected – beers, drinking, and going home alone to jerk it.

I saw Carolyn a handful of times over the course of the next year or two but having placed her in that unattainable category, never made any sort of move, and other than a perfunctory 'hello' at the rare nights where we were out together, we both more or less ignored each other. Eventually I ended up with a girlfriend and moved to a new city.

Fast forward a year or so, and the evil scorpion woman who I'd moved cities for dumped me. I was devastated and moved back home, tail between my legs, and spent a month or two being glum, mopey and depressed. I then got a decent pep talk from one of my friends who basically forced me to start socialising again. He was into pickup, and started giving me pointers on what to say to girls, what not to say, how to behave, dress, all that sorta stuff. I started flirting with girls again, started getting my confidence back and essentially reinvented myself as a man about town.

Then one Friday while at work, I got a text from my sister. 'Drinks after work? Carolyn's gonna be there.' She had me at 'drinks', but mentioning that Carolyn was going to be there? That was the cherry on the muffin, although I mused for a while over why she'd deliberately mentioned her. Had I unwittingly flirted with her on one of the other nights out? Had I spoken about her to my sister at all? I couldn't recall any specific conversation other than the typical 'aye I'd do her' laddish talk. I gave up thinking about it, but made sure that I spruced up before going to meet my sister and her friends.

As it turned out, it was my sister, two of her male coworkers and Carolyn. It's weird, I'm normally quiet enough when introducing myself to new people, but for some reason that night I was cocky and boisterous. From the outset I flirted outrageously with Carolyn, who was completely taken aback by this supposed new me. I got on well with the lads and we had a great time, swapping stories, taking the piss out of each other – and out of Carolyn. Like I said, I was over the top in my flirting. Gesturing wildly, touching her arms, shoulders, grabbing her hips as I squeezed by her to get more drinks, making fun of her, making fun of me, just having a laugh in general.

As the night went on I started talking less to the two guys and more to Carolyn. My sister was getting more and more hammered and she eventually got herself a taxi home. I went to the bar for more drinks and came back to find that the two guys had also left, Carolyn was sitting there alone. 'Where'd the boys go?'

'Oh they just left. They've work tomorrow.'

'Ah right. Just us two then.' I shrugged and continued the flirting. I can't remember exactly what I said nor how I said it, but man, I was on fire. She was giggling, spilling her drinks and touching me back. Game on. I leaned in for a kiss and she pulled back. 'What are you doing?' she asked coyly, smiling.

I pulled back, confused. 'What? I thought you… I mean… don't you want a kiss?' is all I could think to say. Bear in mind reader, that at this point in my life, I'd only ever had serious long term girlfriends who had chased me rather than the other way around. I'd never really had to learn the ins and outs of flirting, and girls playing hard to get.

Still smiling, she looked down at her lap, then up at me coquettishly. 'Well yes. But a gentleman would ask first'. Seriously. 50's vintage clothes and 30's attitude to boot. I grinned as realisation dawned on me. She was playing a game.

'Of course.' I nodded, 'May I kiss you?' (Hey, if she was gonna play the roaring 20's Scarlett O'Hara/ Rhett Butler game, I would follow suit). She smiled in delight and made a show of looking around. 'Ok, but make sure you don't tell your sister.'

I smirked, 'uh-huh', and leaned in and kissed her. Bingo.

We finished our drinks and left and she made as though to hail a taxi. I stopped her. 'What are you doing?'

'I have to get a taxi home?' She said, as though I were dumb. Ever the coquette.

'Or you could just come back to mine? I live a five minute walk away.'

She made a show of acting reluctant and kissed me to stall. I said 'No pressure, I’ve a spare bed you can use.' And she replied, 'Ok. But don't tell your sister that I spent the night in your place. Even though there'll be nothing to tell because nothing's going to happen.'

I nodded again as I took her hand, 'Sure thing.' I don't think either of us believed it.

We walked back to my shitty, tiny apartment and got into the living room. My flatmate (incidentally, the guy who gave me the pep talk) was away for the weekend, so I had the place to myself.

We kissed some more but after a few minutes she broke off and said, grinning again, 'Ok. I have to go to bed.' I gave her a sceptical look.

'Really?'

She smirked in return. 'Yes. Where's your spare bed?' I looked at her again.

Off my look she giggled, 'What? You didn't think anything was going to happen, did you? I'm not like that Mark, I'm a good girl.' More games.

I played along. 'Of course not. Come on, I'll show you the spare room.' I took her by the wrist and brought into my bedroom. She looked around.

'This is a boy's room. This isn't the spare room. Why did you bring me in here?' She made no attempt to leave though.

I closed the door. 'I don't have a spare room. This is my room.'

'And what do you think I'm going to do in here?'

I walked over to her and started to unclasp the corset she was wearing. 'You know what.'

'Erm. What do you think you're doing?' She asked playfully as I leant in and started nibbling at her neck. She didn't resist though and giggled, tossing her head back in pleasure in a way that – over the course of what soon became regular hookups – I came to recognize as one of her ‘I want you to fuck me’ signals. She reached back and willingly undid a few clasps herself. Then she reached down and stroked my cock through my jeans. 'Feels pretty small. I don't know what you think you're going to do with that.' Her belittling of me, I would discover, was also one of her signals.

I unzipped her trousers, slid them down a bit and started playing with her clit. 'Lets find out.' Holding on to her loosened corset, I pushed her back gently so that she fell onto the bed, legs dangling off the edge and bare chested save for her bra. I knew she had big tits, but seeing them almost free sent an extra jolt to my dick. They were magnificent. Perfectly round and only just contained by the Victoria’s Secret bra. A classy girl was our Carolyn. I shook my head in disbelief that she was lying in front of me, on my head. How had I transitioned from the sadsack I was only a few months ago, to where I was now? I made a mental note to buy Johnny several beers the next time we went out.

Her legs dangling, I knelt down between them and pulled her g-string to one side, exposing her freshly shaved and smooth skin. I slid my fingers along her thighs and up to her swollen wet lips, gently pushing inside a little – enough to lubricate my fingers and thumb. I brushed them on up, my fingers playing with her engorged lips as my thumb reached her clit, and began to rub and play with it gently. She shuddered and gasped, widening her legs. I looked at her pussy for a few seconds, I needed to taste it. I leaned in and tongued lightly, licking along the whole length, still playing with her clit with my thumb.

My tongue flicked back and forth along her wet, bare slit, darting inside her momentarily, then sliding up to where my thumb was. Carolyn squirmed and sighed, lost in bliss, ‘yes, just there, do it like that’. My left hand reached up, groping for her chest, and Carolyn willingly took off her bra, letting me play with her fantastic tits. Fuck, they were so large and pillowy, it was like squishing down on giant marshmallows. I kneaded them softly with my left hand, then moved up with both hands and eventually moved my entire body up, kissing her all over as I did so, finally arriving at her wonderful breasts. I, softly at first then decidedly less gently, started sucking and licking at them as my crotch ground in circles against her soaking wet panties.

She responded in kind, gyrating against me and I looked up to see her eyes half closed, looking down at the top of my head. ‘I can’t believe I’m letting you do this to me’, she said, with a coy smile.

‘I can always stop’, I said, lifting my head and ceasing my ministrations. She pushed my head back down, ‘No. Don’t stop. I like it. I just didn’t think you’d be this good.’ Music to my ears. It’s weird, up til this second, I’d thought her frigid.

‘Good?’ I chuckled. ‘I haven’t even really done anything yet.’

She whimpered in anticipation and reached down to my belt, attempting to undo it as I lay on top of her. I lifted myself off of her slowly, and stood up. ‘I’ll take care of this’. I unbuckled deftly as she watched closely through semi-lidded eyes. She licked her lips absently and shimmied her hips, removing the last of her clothing. Fuck, she was absolutely exquisite. And that’s the actual word that went through my mind. ‘Exquisite’. Followed directly by, ‘How the fuck did I manage this?’ I figured I owed Johnny an entire brewery by this stage.

Somewhat awkwardly, I pulled down my jeans and stepped out of them, leaving my boxers on, my cock trying it's best to poke its way out of uncomfortable confinement. I clambered over Carolyn until I was once again lying on top of her, looking into her eyes. She felt around with her hand. ‘You haven’t taken off your underpants.’

I nodded, nibbling again at her neck and ears, making her shiver. ‘I know. That’s for you to do.’

‘Why?’

‘That way I know for sure you want me.’

They say that girls have their tests in the bedroom, but I guess us guys have our own, and this was one of mine. Deep down, I knew that she was just playing around with all the ‘Oh it’ll never happen’, ‘You’re too much of a dork,’ talk, but something in me wanted; no, needed her to give in and admit that she wanted me.

She didn’t say anything, just held my gaze and slowly pulled my boxers off. My rock-hard dick sprang out once she had pulled the band far enough down and I shuffled slightly, letting the head rest directly on her soft, wet lips for a few moments, savouring the sensation.
I teased at her entrance for a few more moments, pushing in imperceptibly, then pulling out. She moaned breathlessly in frustration, ‘I can’t take this anymore, just put it in me’.

At that, I slid in all the way and she gave a long, satisfied groan of ecstasy, shuddering and wrapping her legs behind my back.. Fuck, she was tight. I could feel her stretching around me as I pushed in deeply, then pulled out slightly, getting a rhythm going. She reached up and pulled me by the neck into her, kissing and biting my neck as she pumped her hips up to meet mine. Grabbing my neck with one hand, she raked her hands over my back with the other, her nails digging in deep. The pain only served to urge me on and I ploughed into her over and over. She tightened around me and loosened. Doing it again and again so that I understood that she wasn’t cumming, she just knew how to use her pussy. So much for her being frigid.

Already I could feel myself getting ready to explode, so I pulled out for a momentary respite. She grabbed down at my slick cock, coating her hands in her own juices and rubbed her tits. ‘No, don’t stop’, she almost whimpered. She tugged at my cock, guiding me into her again. I stopped at her entrance, ‘I can’t!’ I grunted, ‘I’ll come in about 2 seconds!’

She pulled me into her, ‘So will I. I want to feel it inside me when I cum’. I pushed inside her again, harder and faster. If she wanted this over with, I’d happily oblige. I pounded at her box roughly, not caring if this was what she wanted, but she responded by making her squeals and yelps and moans louder and coarser as I felt her own orgasm get close. She started trembling and shaking all over and her groans of ecstasy got louder and louder.

I could feel her twitch all around me as I plunged into her again and again, and with one final thrust, I grunted loudly, feeling my dick shoot out ribbons of cum deep into her. She squealed one final time and I felt her ankles lock behind my back, pulling me even deeper if it were possible. She gasped and let go in one go, flopping backwards, totally spent, and still shaking.

Sweat dripped from me as I rolled over beside her. Trembling, panting, she snuggled into my chest and giggled over gulps of breath, ‘I had no idea you’d be like that.’

‘Like what?’

I can’t believe you made me come like that!’

I looked at her, trying to play it cool, ‘Well you were the one who made fun of my small dick. It felt like it had something to prove.’

She giggled. ‘So much for ‘nothing going to happen’. I chuckled easily in response.

After a few minutes of comfortable silence in which we got our breath back, she suddenly looked at me pointedly, ‘You better not tell your sister.’

Source: reddit.com/r/gonewildstories/comments/3cf86n/dirty_carolyn