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? 1

Prospective Sister-in-Law, 2

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…)? Second 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? If you’ve seen my first post you already know E. Slender, quite short, long dark hair, cute glasses, really rather beautiful. I knew her because she was my (then) fiancée’s younger sister and myself, my fiancée, E, and E’s boyfriend (now husband) were living together in a house-share.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After our first hook up things had changed between us. We were far more flirty when we got moments alone together (which wasn’t often). We’d also started texting each other a lot. At first these were of the ‘That was a mistake no-one can ever find out’ sort, but they progressed. Within a week we were telling each other the things we wished we could have done if we’d had more time. About ten days after that first time E texted me saying that her boyfriend was away for the weekend to see his parents, he wanted her to go but she really didn’t want to, and that with him gone we could have more fun. Between us we worked out that my fiancée would be out at work on the Saturday from about 8 until 4, with her boyfriend gone from 9 we’d have most of the day alone in the house. E spent the next few days texting me scenarios she hoped we’d get the chance to live out.

The day came and I was already downstairs having seen my fiancée off to work when E and her boyfriend came down the stairs arguing. He still wanted her to go with him, she was wearing a sort of pyjama vest top and pyjama shorts and was clearly not going anywhere. From the living room I watched them argue until the boyfriend had to leave. He went to kiss E and she refused, he looked hurt, and left. I know it’s not nice but I remember this moment vividly – knowing the things we had planned it seemed comical her boyfriend wasn’t even allowed a peck on the cheek. He left, slamming the door and E walked into the living room. She watched him walking to his car through the window before turning to me and saying something like ‘alone at last’.

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? E walked over to where I was sat in an armchair and straddled me. We started kissing passionately, I took off her top and got a second chance to suck and play with her tits. She seemed to be really enjoying me sucking her nipple and moaned loudly. At first I was shocked by her volume, but quickly understood that we were alone and could really enjoy ourselves. She was grinding against me whilst I played with her breasts, then leant forwards and whispered in my ear ‘I’m going to suck you’. She climbed down my body trying to maintain eye contact and pulled my pyjama trousers down to my ankles. She took my dick in her hand and licked the tip a little before taking me in her mouth. She kept eye contact again and I was overwhelmed by the situation. It was crazy and my head was full of pleasure, regrets, and fears. She kept pushing further down me trying to take more into her mouth and started making gagging noises. I moaned loudly and she obviously like this because she put her hand down her shorts and started touching herself. This was too much and I told her I was going to cum – this spurred her on and I came in her mouth. She swallowed and held me in her mouth before putting me away. Between my panting she told me to go up to her room, get naked and get in her bed. I did and a few minutes later she followed. She stripped off her shorts and joined me. We kissed – it became clear that she had brushed her teeth whilst I was up there waiting for her which I found cute and a little weird. We made out and explored each others bodies under the covers for a long time. She wanked me until I was hard whilst I fingered her. Her breathing was getting erratic so I threw back the duvet and moved down to eat her out. I can clearly remember her smell and taste and thinking that it was similar but slightly different to her sisters. I felt really bad but laughed at the absurdity of my situation and E frowned at me confused. I sucked her clit harder whilst I had two fingers curled up to her g-spot so she soon forgot my laugh and before long was cumming. I kept eating her throughout her orgasm and used my spare hand to feel her chest. She held my head tightly against her and there were points when it felt like I couldn’t breathe. As she came down from her orgasm I crawled up her body and penetrated her. We fucked missionary for a little while before I came in her. I held myself inside her for a long time, until I was soft. Just the two of us kissing, looking in each others eyes and talking nonsense. When soft I sort of flopped out and we spooned. We talked more whilst spooning, about how wrong it all was, about how she’d brushed her teeth (apparently she doesn’t normally swallow and had got sort of carried away but had to freshen up before we played anymore), about how sensitive her nipples were. We then shared a little post-sex nap.

I was woken up by E who had just checked the clock – we’d already used most of our time and she had one thing she’d kept mentioning that she really wanted to do. We both skipped out of bed and went to the bathroom to run a bath. We felt each other up and made out whilst the bath filled and I got in, she got in on top of me (her back to me) and we laid in the water for a while touching each other. Then we stood and soaped each other up with our hands. We spent a long time kissing and mutually masturbating in the bath before we rinsed the soap off. She climbed out of the tub and went to put a towel around herself. I took it off her and we made out again, I laid her on the floor and positioned myself so we could 69 whilst lying on our sides. She was more delicate and gentle with me this time. I tried to mimic her treatment of my dick in how I licked and fingered her. Eventually I heard panting and saw her cumming. I was nowhere near (having already ejaculated twice) and whilst she tried to keep sucking me after orgasm I stopped her and we dried each other off, cuddling whilst wrapped in the towels. Time was a little pushed now so we went our rooms and dressed, I collected my pyjamas from her room, and we had a last kiss before my fiancée got home. We promised each other this would happen again.

Did you have an orgasm? Did your partner(s)? Me once from oral once penetration, her twice from oral.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We knew we were clean and had had unprotected sex the first time we hooked up. From knowing her, her sister and our naughty texting I also knew that she really liked a guy to cum in her so I was hardly going to suggest condoms.

What were your REASONS for having this hookup? It was part two of what had happened a couple of weeks before. That first time was rushed, so we had planned on finishing what we’d started. It turned out this second time didn’t finish anything and we hooked up twice more afterwards.

Were alcohol or drugs involved? If so, how much? None for either – this started shortly after breakfast time so it would have been weird if it had.

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? This time I did feel guilty because whilst the first time had been a betrayal it was all about spur of the moment fucking. This was planned, it was emotional, it was a proper betrayal of our partners and we didn’t care enough to stop it – in fact we actively continued to pursue it. I think during the post-sex cuddling I realised this wasn’t just cheating but had the potential to be a full blown affair. None of this stopped us from carrying on down that path though.

To whom did you talk about the hookup? How did they react? No one knew except the two of us which kind of kept it ‘special’ in a sick way.

Was this a consensual and/or wanted experience for you? For your partner? We both wanted this, it was a second hook up, it was planned, we then planned (and did) hook up again.

Do you regret this hookup? If so, why? This is when our cheating became emotional not merely physical so yes. In the days that followed E and I would text and it wasn’t the same ‘I want to suck this’, ‘I want you to do that to me’ that we’d had before. It was tender things, stuff that couples know but others shouldn’t. There was still sex chat whilst we planned our next time but there also seemed to be a real emotional connection. From this time forward it was more than sex and I definitely regret that.

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 from a selfish point of view was the first blow job – E was truly skilled. Looking back, the real best bit was also the worst which was the emotional connection. The wondering if I’d met the right sister. It felt wonderful in the moment and painful in the moments after.

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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