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? 2

Prospective Sister-in-Law, 3

How long ago did this hookup happen? 8 years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Third time cheating

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? Again this was with E. She was my fiancee’s younger sister. I was living with her, her partner (now husband), and my fiancée. We had hooked up twice before this, and we were starting to form an emotional attachment.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This took place a few weeks after the second hook up. My relationship with my fiancée had taken a really bad turn. It wasn’t anything to do with my cheating (she didn’t know), but more deep rooted flaws in our relationship. I was still living in the house but was now sleeping in a fold out bed down-stairs, and spending all of my free-time looking for a new place to live. We hadn’t officially broken up, but it was a matter of time. E had sent me some really supportive texts, and tried to be a shoulder to cry on, but had to keep her distance when others were around. She couldn’t be seen to be siding with me whilst my engagement to her sister was falling apart. The night this happened I was lying awake on the fold-out, unable to sleep when E came down stairs.

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? The fold out was in the living room and E poked her head around the corner to see if I was still awake. She whispered my name and I smiled at her. She was in pyjama shorts and a long t-shirt, and she smiled sympathetically before walking over to my bed and sitting next to me. We kissed briefly and silently and she asked me how I was coping. I told her not well. She made comforting noises and held my face and stroked my hair. I told her how things were ending with her sister, and I was scared about the future. I started to gently cry. She kept cradling my face and we kissed again. Then she pulled off her shirt and guided my mouth to her breast. She held my head there, and I suckled one and felt the other whilst she put a hand under the covers and into my pyjama trousers. She started to masturbate me whilst sorting of cooing and telling me things would be alright. Unlike our previous sex this seemed all about her comforting me, there was nothing lust filled and animalistic. It was almost like a strange healing ritual. I kept suckling whilst she moved the covers and my trousers away, then stroked me until I got close. She saw, and quickly moved her head down to let me cum in her mouth. When I was finished she swallowed, and smiled at me and whispered something about that being the cleanest way. I wanted to kiss her but she wouldn’t let me. She kissed my forehead and said things would get better before putting her shirt back on and scampering back up stairs.

Did you have an orgasm? Did your partner(s)? I did. She didn’t.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None.

What were your REASONS for having this hookup? I think it was her way of comforting me. She had, accidentally, become one of my closest confidantes and with our obvious sexual attraction and her not being able to give me a shoulder to cry on during the day this seemed to be her way of compensating.

Were alcohol or drugs involved? If so, how much? None.

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? The next day I got a couple of texts where E confirmed that we should try to keep this going. We both felt that something was growing between us, but we both agreed it would be really difficult whilst I was still living there. We did manage to hook up again, but only after I had moved out.

To whom did you talk about the hookup? How did they react? No-one.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual for both.

Do you regret this hookup? If so, why? No. My engagement was all but ended. E took total control of this and in a weird way it didn’t feel like a normal sexual encounter anyhow. It was more like we had grown close and this was the best way E could show her support for me given the circumstances.

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 I felt safe, comforted, and loved in a way that I hadn’t whilst my relationship disintegrated. The worst was knowing that it couldn’t really keep happening like this. I needed to move out and then, between us, we would have to see whether any future was possible.

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

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

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