The best worst threesome ever (long)

I'd been a bit down on my luck. I'd lost a job and had gone to the M4 Corridor to try to find new work, and while I was looking two college friends – Mike and Karen – had generously offered me their spare room.

While I was job hunting, I got to know Mike and Karen a little better than I had at University. Mike, shorter than me but fitter and darker haired, had got himself a managerial role. Karen, who hadn't found the right job, was in admin. I found out pretty quickly that Karen was a lot less straight laced than she first seemed. Whenever we were alone, she'd flirt (harmlessly) and share jokes that she'd never repeat while Mike was around. Karen was pretty, and worried about her appearance because she'd put on weight at her job. In Uni, Karen had an athletic figure with very few curves but now she had boobs and an ass. She wasn't happy with either, although Mike apparently was.

The other person I got to know was Nell, their neighbour. She was a few years older than me and worked for a pharmaceutical company. She was a pretty brunette woman who fit nearly every science stereotype: wore glasses, had no particular interest in clothes, hairstyle, makeup and seemed less aware of social cues or conventions. Add to this a background heavy in catholicism and you have an attractive, intelligent and highly capable woman disguised as a sheltered teenager. Nell's greatest feature was her U-Boat sense of humour, which would shadow a conversation for ages before torpedoing it with a single comment before disappearing again. I was single at the time, and kind of interested in her.

One evening, Karen and I were home together while Mike went out to play Squash. We opened a bottle of exceptionally cheap white wine (which I loathe, but any port in a storm) and had a couple of glasses. Karen's conversation turned flirty, which I was sort of used to, but what surprised me was the appraising glance she gave me before sighing "some days I wish I was single" into her glass. I asked her what she meant and she told me that Nell had admitted she was interested in me, but wouldn't ask me out because of the age gap between us. That confused me, because I'd assumed we were the same age but it turned out Nell was older, and by almost ten years. "She fancies you A LOT" said Karen "and I had to sit and listen to her talking about all your good points, which I'm already aware of."

All news to me, but nice news.

A couple of weeks later, we all went out to a local beer festival. Mike never used to drink much, always claiming he didn't like to be out of control, but he was sinking more than normal. The beer was decent enough, and both women were also getting into the beer. The pub closed, so we went home and, sitting in the taxi, the consensus was that no one wanted to stop drinking. Back at Mike and Karen's place, we switched to wine and drank a bottle of something Hungarian and red that was completely awful. Then Karen suggested we play a game. She pulled out Trivial Pursuit, which everyone readily agreed to. "With a twist" said Karen "that being, if you're going for a wedge and you get the question wrong, you lose an item of clothing."

Now, I was heading towards drunk. That makes me competitive, and I wanted to win. At first, I didn't notice what was going on. Another bottle of wine went the way of the first, and a third was opened. Mark was rapidly down to his boxers, much to Nell's amusement, and then Karen started losing clothes too. It occurred to me that she was getting stuff wrong that she would normally have got right, but I put this down to booze and kept playing. Nell ended up shedding clothes too, and I took a little more interest as her skin emerged. She lost her sweater quite happily, didn't worry when she lost her shoes and the socks she was wearing under them. She was a little concerned when she failed another question and had to make a choice between the t-shirt she was wearing or her jeans. To my surprise, her jeans came off and I got a look at her arse encased in a pair of very ordinary plain white panties. Karen, on the other hand, was down to a very lacey and flattering bra and knickers set and I was still basically clothed. I'd lost shoes and socks, and was quite pleased with myself but evidently missing the point. Then Karen failed a simple question and had to decide whether to lose her top or bottoms and a moment later was topless.

Shit, as they say, had got real.

I became very aware of two things. Firstly, Karen had really nice tits. They were small, with pale nipples, and she was showing them off with apparent pride. Secondly, she was pointing them at me quite a lot. It took a moment for everyone to come to terms with how far the game might go, which was just as well because Mike then lost his boxers.

He stood up to take them off, which was bold of the man, and to be fair he had every reason to be. As he stepped out of his boxers I could see Nell's eyes fixed on his cock, which was getting harder as she watched. Nell must have been surprised because she gasped and said "It's getting bigger!".

"Well, that's because I'm topless" said Karen, "your turn, Nell"

and a few moments later Nell was sat in bra and knickers wondering how best to hide herself. Her bra was like her panties – utilitarian, but couldn't hide the fact that her nipples were hard. She didn't want to meet my gaze, but was definitely interested when my memory failed me and my shirt came off. Half a bottle of wine later and we had reached a very interesting situation. Mike was naked, hard and clearly looking to play something other than Trivial Pursuit. Karen was looking for an excuse to take her knickers off but clearly wanted Nell as naked as possible too. Everyone broke to refresh their drinks and Karen came to sit by me for a moment.

"What do you think, Nell? Should he catch the rest of us up?"

Nell nodded. So I, being helpful, stood up and was rewarded with the sensation of Karen unzipping my jeans and then unbuttoning them, then dragging them down. Nell's eyes were rivetted to my groin, which Karen noticed.
"Shall we get his boxers off too?"
Nell blushed and nodded, and before I could say anything about the matter Karen had removed those too. I was semi hard, and Karen seemed pleased with what she'd revealed.
"Does that get bigger?" Nell asked her. Karen grinned.
"Shall we see?" she said, and without saying anything else wrapped her hand around my cock and gave it a stroke or two. I wasn't sure anything would happen, given all the alcohol, but happen it did.
"Want to try?" asked Karen. Nell nodded, hesitantly, and reached out her hand. After a moment or two of quiet instruction from Karen, Nell was happily stroking my cock with the sort of intense concentration that said she was really invested in getting it right.

I looked around and found Mike and Karen in a pretty heavy makeout session, which didn't really hold my attention all that long becasue Nell, for all her concentration, wasn't very good at giving handjobs. I asked her to stop, and she asked me why.
"Because if you keep that up I'm going to cum" I lied, but she grinned and stopped. She asked me a bunch of questions about my cock and I answered them, while gently suggesting to her that since everyone else was naked she should be too. She agreed, but hid beneath a blanket and then asked me to massage her shoulders and back, which I agreed to. I dragged a couple of cushions off the sofa for her to lay on and she sprawled on them while I straddled her thighs and ran my hands over her back. She wiggled a little.
"I feel a bit trapped like this" she said "can we..uhh…" I hopped to one side, which she also didn't like, and then she parted her thighs and asked me to kneel between them. I obliged. I could see Karen enjoying herself with Mike, but she was grinning at Nell's request and rolling her eyes. Nell's discomfort had me pressing my cock into her ass, and when she realised what the pressure was she shifted again and the head of my cock ended up pressed against her pussy. As I massaged her back, the pressure continued and she seemed to be getting into it. All it would have taken was a little more pressure from her or me, and a little adjustment, and I'd have been in her. It might have gone that way, too, but for two things. Firstly, she realised she was getting wet and second she worked out what was touching her and where. She froze, scooted away from me and excused herself to go to the bathroom. She grabbed a handful of clothes on the way out. A few minutes later she came back, fully clothed, grabbed her shoes, made some quick and flustered excuses, and left.

Which brought my evening to a crashing halt, or so I thought. Karen and Mike had a short whispered conversation while I started to pull my clothes together. Karen moved to sit next to me, gave me a hug – which was an odd moment, since we were both still naked – and then kissed me.
"We thought you might like to join us" she said and lay back on the cushions.
Mike claimed territory pretty quickly by diving between Karen's thighs and going down on her with the sort of enthusiasm that told me this was all for her benefit. Still…once Karen had settled down she reached for my cock and started stroking it, demanding that I kissed her while Mike ate her out. The angle got awkward, so she had me kneel beside her and play with her firm, rounded tits and hard brown nipples while she stroked me. She arched, stretched, moaned and craftily kissed the head of my cock, which earned her a nervous look from Mike so we went back to kissing and stroking.

The only problem with this was that in her distracted state her hand was doing nothing for me at all. Even though she was clearly enjoying having a hard cock to play with, Mike was far too adept at pleasuring her for her to concentrate on me worth a damn. I was hoping that Mike might decide to fuck her so I could either go to bed or get myself off instead. As it happened, all of a sudden she froze, then started gasping and moaning leading up to the biggest shuddering climax I'd ever seen a woman have. I sat back and let Mike and Karen have a moment or two. I'm not sure what I was expecting but after a moment or two of cuddling, she got up and lead him off to their bedroom. I shrugged and started to fix the room up a little, gathering my clothes as I did so. I was wondering whether to take a shower and jerk off when Karen returned. She smiled, walked up to me, gave me a hug and kissed me on the lips.
"Can we talk?" she said.
So we sat in the front room and she explained that Mike had always wanted to have a threesome, as had she, and the intention had been for Nell or I to join them.
"I'm sorry for making you a player in our game" she said and I shrugged and told her I was perfectly fine with it. Because you do when a pretty girl is naked and apologising for a near threesome.
"How's Mike?" I asked.
"Asleep" she said "poor guy was so excited he came as soon as I touched his cock."
And then she looked up at me.
"Which leaves me with a problem" she said "because I really need a cock inside me. Do you mind? It'll only be this once. I've wanted you for a while and I was hoping he'd at least let me blow you…but…"
I thought the best way to answer her was to kiss her hard and deep, which she responded to by taking one of my hands and pushing it between her legs. I pressed my fingers against her, feeling how wet she was, and with the slightest pressure my middle finger slipped inside her. She rocked against my hand as we kissed and groped each other and then suddenly pulled away. I was worried about an attack of conscience but she knelt and said
"Since it's just once, might as well get all the fantasies in!" She pushed my thighs apart, took my cock in her hand and then kissed the head, enveloping it swiftly with her lips and slowly taking more and more. I'm just a little larger than average but she didn't take my whole cock into her mouth, she bobbed and sucked, licked and kissed for a good few minutes, brining me uncomfortably close to orgasm. I asked her to stop and she grinned.
"Gonna fuck me, then?"
We both ended up on the floor, kissing hard and pawing at one another before she spread her legs and I got between them with my cock pressed against her pussy.
"I need it" she said "just once, so make it a good one?"
I teased for a moment, but couldn't wait. I slipped inside her, pushing until our hips met and my balls were against her arse.
"I need it hard" she said, but I didn't oblige. I was balls deep in a gloriously warm, wet and above all tight pussy and I wanted to savour the moment. She looked so desperate, though, that I did what she asked and started to pound into her. I held her legs over my shoulders and gave her everything she asked for, and for as long as I could. She bucked back against me, grinding, gripping, and it wasn't long before I could feel the cum rising.
"Where do you want me to cum?"
She looked into my eyes and smiled.
"I did say ALL the fantasies…so…in me. I want it deep in me."
I thrust once, twice, then buried myself in her. As I did, she gasped and her pussy started to pulse around me which took me right over the edge. I emptied my balls into her as deep as I could and kissed her as she gasped.

We lay together for a few minutes and then helped each other clean up. Next morning, everything was back to normal.

Well…not quite. Karen took me aside and thanked me for the previous night, swore me to secrecy and then confessed that she was hoping it wouldn't be a one time thing after all. Which made the next six months interesting.

Source: reddit.com/r/gonewildstories/comments/40jy04/the_best_worst_threesome_ever_long