Date Takes a Strange Turn



What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? UK
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Rentals
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 26
How many hookup stories have you here posted before? 0

Date takes a strange turn

How long ago did this hookup happen? 20 years

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than 6 months

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Before I headed off to university, I had a summer job straight from school. The workforce was made up of mostly young men and women, and as such, there was a very fluid and bountiful grapevine of whispering about this and that. I was really hung up on a girl I worked with, Ruth She wasn’t classically pretty, although I certainly fancied her as would many others, but she was incredibly beautiful in spirit. Sweet, clever, slim, well presented, let’s say quirkily pretty, and I was very attracted to her. She’d been troubled in her personal life with a controlling, much older boyfriend, and whilst working at the next desk we became friends as she shared a lot of her troubles with me. She just needed to leave this guy. Maybe for me? I never said this as I was heading off to university before long, I kept it to myself and just helped as best I could. I went off to Uni in the September (she worked there full time) and I didn’t see her again until the next summer.

I rang the office and arranged to work there again in the holidays. The money was good and it wasn’t entirely unsatisfying work helping people in mild distress. However, this time, I found myself working on a different shift pattern to Ruth, so I’d not get to see her as before. However, the first time, I did see her, as our shifts crossed over, she gave me a really warm hug and seemed delighted to see me. She told me she’d just last week moved in with Karen, a friend of hers who I vaguely knew, after having finally extricated herself from her evil boyfriend. We swapped numbers and talked about going for a drink. I wasn’t sure in what capacity but hell, whatever, let’s just go and find out. But our shift patterns! When one person had a day off, the other one would be working. We eventually arranged a group night out which would happen on my day off, and after her shift had finished. I’d pick her up from work, we’d go for a drink and catch up, before heading out with some other people we worked with. “It’s a date!” she would conclude by text. I thought it was on.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I picked Ruth up from work, meeting her in the reception and walking to the pub over the road. She linked my arm as we walked. She told me she was much happier now, she felt free and was loving her new life living with Karen in the flat they shared. Then she told me she has something else on her mind. She was in love. In love! No… not with me. No. This other guy Rod, who I sort of knew from the previous summer and always regarded somewhat scornfully. A surly guy who’s only redeeming feature seemed to be his small town good looks. The kind of guy that never smiled in photos. Knowing Ruth it seemed like a terrible match, but he’d made a perfectly timed move and had given her the motivation to end things with the dud. She told me she hadn’t been ‘physical’ with Rod yet as she’d wanted the dust to settle a bit, but that he was meeting up with us all later and coming back to her place.

So not only had my plans of a ‘date’ gone awry, Ruth was telling me that she planned to fuck her new boyfriend that very evening. It was not how I’d envisaged things panning out. However, she asked me if I remembered her new flatmate Karen. I told her I knew her to look at, but I don’t think we’d ever spoken. She’d been working on a different shift the last summer. Ruth said that Karen remembers me very well, and that basically she’s ‘available’ if I am. Oh, and she’s coming out with us later. My head was blown.

We went to Ruth and Karen’s flat in the town centre. A handful of people were already there, although Karen was in the shower and was still to get ready. We opened a few drinks and shared some weed. At one point, Karen came out of the shower room and, wrapped in a towel, hurried across the hallway to her bedroom. The towel was clutched up around her chest but from the rear you could see her naked back to just above her ass. I mused that despite my earlier disappointment, I’d been in worse places. But I didn’t know Karen at all, and while she was pretty, with long black hair and nice figure, I didn’t know if there’d be much of a connection.

We went out to a few bars, noisy places where you have to shout to be heard. Not great places to get to know people, but with some drinking and dancing, everybody was getting merry and silly. By the time we reached somewhere a bit quieter, I was already moderately drunk. I approached Karen when she was waiting at the bar. She was wearing a tight fitting top which showed off her figure and a slim skirt with dark green tights and heels. I told her with drunken straightforwardness (that when sober I lack) that she looked great, and she replied with a similar lack of inhibition and asked what my feelings were for Ruth!

Again my head was blown – how did she know I liked Ruth? She told me her and Ruth had spoken about me, and Karen had worked out, despite Ruth’s protestations, that I thought of her as more than a friend. Ruth thought I’d been entirely platonic with my helpfulness, but Karen knew otherwise. She knew how men’s minds really worked. So did she need to feel threatened by my feelings for her new housemate, or not? My drunkenness again made me honest, and I told her I found Ruth attractive, but I played down any feelings involved, saying that I wasn’t looking for anything serious from anybody as I’d be heading hundreds of miles away back to university in a couple of months. Karen became a bit jovially hostile with me thereafter, joking that I was only interested in easy sex and that I wouldn’t get any from her. She questioned me further, asking about university girls, and she accused me of being a stereotypical man who pretends he’s not. I couldn’t tell if she was joking, but she was clearly enjoying giving me a hard time.

We met up with the aforementioned surly Rod, and he and Ruth spent the rest of the evening close together whispering in each others ears and playing with each other’s fingers. Sickening stuff. A dozen or so people, myself included, went back to Ruth and Karen’s flat to smoke weed and round out the evening, drifting off in taxis over the next hour. At some point, without anybody noticing, Rod and Ruth disappeared off to her room. Karen loved a smoke it turns out, and we watched late night TV giggling away until everybody else had gone home. I suggested I’d call a taxi and let her go to bed, but she said I could sleep on the sofa if I’d like. After all her accusations of me wanting an easy fuck, I held off from making the obvious move on her right there and then. She went off to bed and I made a bed on the floor using sofa cushions.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? About five minutes had passed before I heard the door open. Karen stood at the door to the living room still dressed and chuckled at me undressed down to my boxers in my makeshift bed. She asked if I was comfy down there? I told her it wasn’t too bad actually, it’s comfier than it looks! Then she asks the question. Do I want to sleep in her bed? A straight up proposition. I sat up on my elbows silent for a while, staring at her, stunned. I tried to make a joke, I gestured to my nakedness and said I thought she had me at a disadvantage. Like Bond, but infinitely more shit. Unsmiling, she turned and went back to her room. Before her door was closed, I was on my way after her.

Her room was quite small, with a single bed along one wall, a wardrobe opposite and dressing table under the window. She had a little bedside lamp which lit the room in a soft orange glow. I stood there, naked except for my boxers, and started to bluster a bit about this being unexpected and that I thought she wasn’t into this sort of thing before she just put her finger on my lips and told me to shut up. I took her hand away and then pulled her body towards mine. It was then that I noticed the noise. Karen’s room was next to Ruth’s, separated by a plasterboard wall. We could hear Ruth and Rod moaning and grunting through the wall. Karen and I smiled at each other as we both acknowledged what we could hear, then we started to kiss whilst stood against her dresser.

I was quite a bit taller than her, and she pushed me to lean on the dresser as the angle was better. I was mostly naked, but she was still wearing her clothes from the night out so I slid my hand up her skirt and firmly grabbed her ass through her bottle green tights. Karen’s hands explored my torso, which back then was fit and lean from university rugby. Her arm kept brushing my now-erect dick which was straining at my boxers. She looked down, slid off my shorts and took me in her hand, slowly stroking up and down and staring at my dick. The noise from Ruth’s bedroom, the alcohol and the weed, and Karen stroking my dick – an animal instinct came over me, I was going to devour this woman. I slid my hand down Karen’s tights and into her underwear. She was soaking wet and convulsed as I began to play with her. Within a minute, her eyes rolled back as she shuddered and swore, and standing in front of me, my dick in her hand, my fingers inside her, she came hard, her knees turning to jelly so that I had to stop her falling over. She rested her head against me and I gave her a moment to recover. She looked up, dishevelled, looking a bit embarrassed at how quickly she came. I kissed her again, then moved to her neck and groped her ample chest through her tight top, before pulling it off over her head. She had a skimpy white bra on which barely contained her breasts. Then I pushed up her skirt and slid down her tights and underwear just enough to expose her ass, span her around and pushed her down so she was leaning onto the dresser. As I moved behind her she suddenly blurted out “Wait!”. She opened the drawer at the front of the dresser beneath her, rummaged around a bit and found a condom. Without looking back at me she held the condom in its packet up for me to take, and when I did, she leaned back down onto the dresser, waiting for me. I unwrapped the condom and put it on.

I positioned myself up behind her and pushed myself in. She felt amazing – wet, warm and tight, and her ass was amazingly firm and pert. Karen grunted as I began to work  her. I was so turned on I was worried I’d cum immediately. The noise through the wall had become more frantic, we could hear the bed banging rhythmically into the wall and Ruth’s moans clear as day. Then came the long drawn out sounds of Rod groaning and cursing as he came. The sight of fucking Karen over her dresser coupled with the sounds next door was almost too much for me, I had to pull out of Karen and wait a moment to stop myself from coming too soon. Karen looked behind at me and whispered she was glad it wasn’t just her that couldn’t control herself.

As I regained my composure, Karen then stood up, turned and pushed me down on her bed. She unclipped her skirt which fell to the ground, slid off her tights all the way and climbed on top of me. She was still wearing her bra as she gripped my dick and slid down onto it. I reached up behind her and released the clasp, exposing her heavy breasts which lurched and wobbled as she rode me. Karen bit her lip and stifled her moans as she found a good rhythm, and within a couple of minutes she came for a second time, shuddering and convulsing violently. She jumped off me and sat twitching against the wall on the bed as she recovered. Again she looked a bit embarrassed. After a moment, I laid her down onto her back, moved in between her thighs and drove back into her. I fucked her harder now, gripping her ass beneath me and pinning her to the bed. Karen covered her mouth but even her muffled yelps were not exactly quiet. Knowing that we’d heard Ruth and Rod, it really turned me on to know that they could probably hear us. Karen moved her hand down to rub her clit as I fucked her, and when she blurted out that she was going to come again, it pushed me over the edge and I came hard with her. She slapped one hand over my mouth and the other over her own to stifle us both, and then afterwards pushed me off.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We laid in bed recovering for a couple of minutes. I found my boxers and went to get us some water from the kitchen. When I returned we chatted about what had happened. She told me that in spite of her protestations, she’d been hoping I’d make a move on her all evening, and when she got to her room and heard Ruth and Rod fucking next door, she got so turned on that she had to just come and ask me to come to bed. I asked her why she’d given me such a hard time about only wanting casual relationships (which in fact wasn’t true, but university life had opened my eyes to it for sure). She said she didn’t really have a problem with casual relationships, but that it was a minefield of twattish men. Her roasting me was a test of whether or not I was a twat, essentially. We talked about being turned on by the sound of others fucking. She said she’d never heard anything like it before. She’d only just moved in with Ruth, she’d lived at her family home previously. She was a bit embarrassed to have got so turned on, blaming the weed and alcohol and a sense of ‘fuck it!’. For my part – listening to someone you’d quite fancied getting screwed for the first time by a new man, whilst fucking her sexy orgasmic flatmate who’d just invited you to bed – very much a sexual highlight for me, and worthy of recording here.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? It became common knowledge at work but I didn’t gossip about it.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all


All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? —

What do you think about the Casual Sex Project? I get turned on reading about real sexual encounters. A lot I take with a pinch of salt though, sorry. It’s nice to document a sexual memory this way, although I’m not sure why people write about bad or disappointing sex they’ve had. Writing it down helps solidify the memory as it grows more distant. I’ve had plenty of sex over the years, but it’s the rare moments – sex when or where you didn’t expect it, or with someone you didn’t expect it with – which are the jewels that linger in the memory. I’ll write a handful more when I get time.

You have a hookup story to share? Submit it here!