First Time Sharing



What’s your gender? Man
How old are you? 36
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Network security
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Wittol
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 0

First time sharing

How long ago did this hookup happen? 5 years

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 3 years

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? This involves my fiancee at the time, now my wife and my best friend who was best man at our wedding. I’d been with my fiancee for three years and had known my friend for 10+ years. They got on well and flirted a lot but nothing really sexual had happened between them previously. Ben (my friend) was very open about fancying Sarah (names changed to protect the not so innocent) and Sarah liked the attention he gave her, I did too.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was at our flat, we were sorting out details regarding our upcoming wedding and having a few drinks. Nothing was planned at all, it was spontaneous.

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? We had gone over various things, duties of the best man, who were going to be ushers etc and had had a fair amount to drink and just joking around. Sarah said that she knew it was traditional for the best man to get off with the Maid of Honour but as it was her little sister Ben should keep his hands to himself. Ben said that if her sister was as sexy as her he’d find that really difficult and if he was expected to be good he wanted a reward. Sarah asked what he wanted and he said he wanted a kiss so she went over and kissed him on the cheek. He said ‘No, I mean a proper kiss’ and Sarah looked over to me with a smile and said ‘Should I?’. I told her it was up to her but if she wanted Ben to leave her sister alone she’d better.

Sarah sat on Ben’s knee and they kissed for quite a while, I saw his hand move round to her bum and squeeze it while they were snogging and felt myself getting aroused. After about 5 minutes Sarah got up looking flushed and Ben also got up and headed for the bathroom but not before I’d seen the bulge in his jeans. Sarah came and sat by me and asked what I thought of her kissing Ben like that and I just took her hand and put it on my erection. She squeezed it and whispered ‘So you wouldn’t mind if I went back for seconds?’. I said ‘No and take it just as far as you are comfortable with’ and she replied ‘Are you sure about that?’. ‘Yes’ I said and pulled her down for a snog until Ben came back in from the bathroom.

Ben gave me a slightly worried look but we both grinned at him and I told him that Sarah wanted seconds if he was up for it. He looked surprised but just said ‘Fuck yes!’ as Sarah went over and pulled him down on the sofa. They kissed again even more passionately and Ben’s hand slid under Sarah’s tee shirt and onto her breasts and after a minute or too she sat up and pulled it off as well as her bra. Ben kissed and sucked on her boobs and nipples and it was obvious to me that she was really getting into it. Sarah put her hand on the bulge in Ben’s jeans and rubbed it slowly then pulled his zipper down and got her hand on his cock. Ben looked over at me and I just smiled as Sarah undid his jeans, pulled out a very erect cock and bent over to suck it. Ben leaned back enjoying the unexpected blow job and after a few minutes pulled Sarah up and kissed her again while undoing her jeans, which she pushed down along with her knickers. They got tangled round her ankles so I got up and took off her sneakers and pulled her jeans off, seeing Ben’s hand pushing her legs apart so he could feel her pussy. I saw she was already wet and her pussy lips were parting so I knew just how horny she was feeling so sat back down and watched Ben fingering my fiancee and rubbing her clit with his thumb. Sarah suddenly clamped her thighs round his hand as she had her first orgasm, jerking against the fingers deep in her pussy.

Ben went to kneel on the floor, clearly intending to return the oral favour but Sarah grabbed his erection and said ‘I want it in me now’. He needed no second invitation, spreading Sarah’s legs and entering her in one push until he was balls deep then slowly building up until I could hear the wet slapping as he fucked her fast and hard. Sarah came again and wrapped her legs around Ben’s ass, pulling him into her as he thrust. My cock was throbbing and I unzipped to get more comfortable but didn’t dare touch it as I knew I’d cum. Sarah pushed Ben and told him to sit on the sofa and straddled him, reaching behind her to position his cock in her pussy and slid down on it. I had a perfect view of his cock pushing into her ass she bounced on his lap, Ben’s hand on her bum helping her clit to grind against him on the down stroke when he was fully inside her. I think Sarah had at least another orgasm before Ben held her hard against him and groaned as he came deep in Sarah’s tight pussy. They slumped together getting their breath back then Sarah looked over her shoulder and said ‘Do you think that was a good enough reward for leaving my little sis alone then?’ I replied ‘I’m not sure who got the best of that deal so maybe count it as a down payment!’ and Sarah said ‘OK, that sounds fair to me, what do you think Ben?’. Ben said ‘I’ll agree to anything after that, it was fantastic. Thank you both!’.

Sarah went to get cleaned up and Ben told me that he’d been worried after the first kiss that I’d be angry and that he’d never expected what had happened. I said that I hadn’t either but that I was pretty sure that everyone had enjoyed it and I had a feeling there would be a repeat at some time before long. ‘Just say whenever you guys want and I’ll be there!’ he said and after getting dressed left. I went upstairs and found Sarah on our bed, she said ‘I haven’t showered yet, I just needed to get my breath back. Give me 5 minutes.’. I said ‘No, don’t bother’ as I stripped and pulled her to the edge of the bed, pushing her legs back so her pussy was exposed. It was wet, red and puffy, obviously freshly fucked and looked beautiful and I slid in more easily than I ever had previously. I didn’t last long and the feel of Sarah’s pussy, wetter and a little looser than usual was the only thing that kept me from cumming as soon as I’d entered her.

‘So did you enjoy me being a slut?’ Sarah asked me a little later. ‘As much as you enjoyed being one I think!’ I replied. ‘I’ll be good if you want me to be’ she said, ‘Or as bad as you want me to be.’. ‘And which would you prefer?’ I asked her. ‘Well, I have to admit I really enjoyed that so if you did too then why shouldn’t we do it again?’. ‘I’m more than happy with that idea if you are’ I said, and that was the start of a ‘hobby’ we still share and enjoy immensely.

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? Sarah asked me the next morning if I was still OK with what happened and I said I was, but if she regretted it then we’d just put it down to experience. She said she didn’t regret it as I’d made it clear I was OK with it, as well as wanting to do it herself. She said as long as we were honest with each other and said if either of us were ever uncomfortable, she thought it was exciting and was happy to be a slut occasionally. I asked if she’d be happy fucking Ben again and she said sure, as long as I was happy too. We still play with Ben when he’s in the UK although he works in the USA so it’s only two or three times a year.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Emotional intimacy, closeness, connection

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? I don’t know / I’m not sure

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

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? Just to each other and Ben, obviously we all reacted positively 🙂

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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

What was the BEST thing about this hookup? It established early on that we were in agreement that sex and love were not the same thing and that sex without emotional attachment with others didn’t damage our relationship.

What was the WORST thing about this hookup? That we hadn’t found that understanding earlier.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, in a positive way.

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

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

Anything else you want to add about this hookup? I know it would not suit everyone, but for those it does it can be very positive indeed.

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? I’d like there to be less sexualisation but more openness and freedom to act as it suits the individual/couple without censure or criticism.

What do you think about the Casual Sex Project? Interesting!

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