by I should regret this

Gender: Male
Age: 30
Race/ethnicity: White – British
Current location: England
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Lecturer
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Prospective Sister-In-Law

How long ago did this hookup happen? 8 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? E was a gorgeous girl, slender, almost too slender, with long dark hair and cute glasses. She’s a cock-sure kind of girl who is used to getting her own way – but with a playful side. I met E through her older sister (who I was engaged to at the time), and when this happened I was living with my fiancée, E, and E’s then boyfriend. I’d always fancied E – most men did.The fact she was my girlfriend’s sister only made it more enticing.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The day before we hooked up E and her boyfriend had been arguing. The boyfriend’s mother didn’t like E (stealing away her baby) and this often led to rows. The mother was coming to see the boyfriend to discuss some “issue” or other and E didn’t like it. On the day the boyfriend and his mother took up residence in our living room. It was a small house so myself, my girlfriend and E all had a pretty big imposition upon us with our main living space blocked off for this conversation. My girlfriend left for work, and with E seeming quite agitated I spent time to talk with her. Normally, I avoided talking to her too much – I didn’t want to appear in any way flirty with a girl I fancied who was so far off limits. A girl who, I kidded myself, I only fancied because she was so far off limits. E kept trying to listen in on the conversation at the door, and I took her hand and pulled her away. It was a big moment, I had only had physical contact with this girl a handful of times despite knowing her for several years. I convinced her that listening to this conversation would only drive her nuts and we went up stairs. She went to sit on her bed and we talked. This is what led directly to us hooking up.

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? Whilst talking, I noticed that E’s nipple was visible down her vest top. Normally, she took a lot of care in her choice of clothes but today she was in a mood and wanted to stay at home so was only wearing some old tracksuit bottoms and a little vest top that she seemed to have slept in. She had no bra and I could see her pert nipple on her small but firm pale breast. I tried not to look, and then to look but not be seen. She was getting increasingly angry at her boyfriend downstairs. Then she caught me looking. She sort of jokingly yelled “oi!” and put a hand to her chest to push the top against herself but this only made her nipples visible through the material of the vest top. I apologised and looked down at the floor – expecting the world to start falling around my ears. But it didn’t. She giggled and asked if I had tried peeking on her before. I was embarrassed but said yes. She, presumably out of some weird anger at the boyfriend combined with being caught in the moment said “well here’s more than a peek” and took her vest top fully off. Her breasts were small, but beautiful. I slowly reached out (slowly to test the water since this situation was so strange) and caressed one, then both. then leant in to suck her nipples. She moaned, and I looked up into her eyes and we kissed passionately. She had been sat cross-legged on the bed with me sat in front of her but now I pushed her onto her back and we made out. Grabbing at each others bodies, kissing her face, neck, breasts, shoulders. She reached the front of my jeans and felt my dick. It was already hard. We instinctively knew we had to be quiet and quick. E’s bedroom was directly above the living room and that conversation could end at any time. I knelt up long enough to pull her tracksuit bottoms down and reveal a small black thong. Nothing fancy, just a cotton everyday thing. I remember looking so deeply in her eyes as I took the waistband in my fingers. We both knew this was the last moment to stop something so wrong from happening but neither of us wanted to stop it. I pulled her thong down, my eyes moving to her completely shaven genitals as I did so. With her knickers in my hand I paused a moment to enjoy the sight of this woman I had lusted after for so long, then I moved forward to make out with her again. We went back to kissing and feeling, I touched her pussy for the first time and it was so wet. I rapidly rubbed her clit and fingered her. I moved to go down on her but she stopped me “no time, just fuck me”. I didn’t need telling twice my shirt and jeans hit the floor so fast and I lined myself up with her. The first moment when I penetrated her was glorious, so warm, wet, tight, her eyes widening, a fantasy realised. We begin to fuck hard, then – worried about noises being heard below – took a slower, more purposeful rhythm. She kept whispering “fuck, fuck, oh fuck” into my ear. Before long I felt her body tense against me, and her neck threw back. I fucked harder whilst she came, sucking her nipples again before cumming inside her. It might have been brief – no more than five minutes from her taking her top off to finishing. But that was easily the most memorable sex of my life to that point.

Did you have an orgasm? Did your partner(s)? Yes, we both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used no precautions. I knew – owing to talks with my fiancée that E was on the pill. It also seemed pretty sure that – given she was having unprotected sex with a long term boyfriend who adored her she was probably going to be clean. I knew I was.

What were your REASONS for having this hookup? I suppose her annoyance with her boyfriend, coupled with opportunity, coupled with (on my part at least) a huge underlying, long term lusting for it.

Were alcohol or drugs involved? If so, how much? No drugs or alcohol – unless female scorn is a drug.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I stayed inside her for a few moments and rolled away to get dressed, we didn’t have time for cuddles and niceties. She took some tissues and wiped herself before quickly redressing. We both felt satisfied, but also a little guilty at having betrayed our partners. We knew that this really should only be a one off. It turned out it wasn’t. We hooked up 3 more times over the next few months. Now, I live in a completely different part of the country. We stay vaguely in touch through Facebook. An occasional message, which is sometimes flirty, but she is now married to the boyfriend from this story.

To whom did you talk about the hookup? How did they react? No one. I slept with my fiancée’s sister – it isn’t the sort of thing you broadcast.

Was this a consensual and/or wanted experience for you? For your partner? Totally consensual for both. And wanted enough that we hooked up three further times.

Do you regret this hookup? If so, why? No. It was excellent and probably the only fantasy I have ever lived out. I regret not having regrets – but think that the brevity of the passing moment of guilt immediately afterwards speaks volumes about my own relationship. We called off the engagement a couple of months after this with no one other than E and myself knowing about our hook ups and for reasons completely separate from them. It was a bad relationship and this is why it’s hard to regret this.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was that it was so animal and primal, fucking despite it being so wrong. And we got to do it again several times. It was easily one of the greatest sexual encounters of my life. The smile on her lips and the look she gave me as I raced to put my jeans on and she tugged her knickers back up will stay with me forever.

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

All things considered, how NEGATIVE was this experience? A little negative

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!