Prospective Sister-in-Law, IV

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? 3

Prospective Sister-in-Law, IV

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…)? 1st time not 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? This was my last time with E (same girl as in previous stories). It was our fourth and (to date) final hook up. She was my (by this time) former fiancée’s little sister.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had recently moved out of the shared house after the end of my engagement to E’s sister. I had a crappy little flat, and E was regularly texting me to try to organise meeting up. We eventually found a weekend where her boyfriend was away visiting his parents. She told me she had ‘extensive’ plans for me, because we hadn’t seen each other for a while, and began texting me nudes and more things she planned on us doing regularly in the build up to our weekend.

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? As with most big sexploits, it didn’t really play out as fantasised, but was still pretty fantastic. She arrived early on Saturday morning and didn’t leave until late Sunday evening. We had so many things we wanted to do and managed most. In brief, we had sex in pretty much every position we could think of on the sofa, my bed, the floor, and in the shower. We did a lot of mutual masturbation and oral. We did kinkier things that we couldn’t do in stolen moments at hers (spanking, hair pulling, choking, and at one point anal whilst she had a vibrator in her vagina). We also did more coupley things (like getting to sleep next to each other without fear of over sleeping, and making breakfast together nude). Basically, it was like those first weekends with a new partner – goofy romantic stuff and then sex until one or other of you can’t keep going.

Did you have an orgasm? Did your partner(s)? Both. So many times.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No condoms – she was on the pill

What were your REASONS for having this hookup? It was the last chance we had really. We’d done this before, wanted to keep going, but both kind of knew that chances were we’d not get all that many occasions to play again.

Were alcohol or drugs involved? If so, how much? we had a little wine on Saturday evening, but we’d already had lots of sex by then so it had little impact on our choices by that point.

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? When she was getting ready to go home, things got on a bit of a downer. I asked her to stay, she couldn’t. I knew she couldn’t. We sort of accepted this would be our last hurrah and were glad that 1) we’d got to have it and 2) it had been a pretty great hurrah.

Incidentally, after my second story I took a punt and got in touch with her on facebook and sent her a link to this. We’ve been talking a bit, and between telling about this affair and talking to her I have opened up some old feelings. We are, speculatively, planning on meeting up again if I am in her town. I doubt it’ll happen – but I hope so.

To whom did you talk about the hookup? How did they react? No one, until now.

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

Do you regret this hookup? If so, why? I regret that it had to end. I’m certainly hoping that when E gets to read this entry we can find a way to meet up again.

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? I suppose the most memorable were her getting us to pee on each other in the shower (something I hadn’t done before), and the fact that she had brought a camera which we used through out the weekend. The worst was that we couldn’t have a relationship afterwards. This affair did change me a lot. I hadn’t had casual sex before, I haven’t had it since. I think I have become aware that I am not capable of keeping casual sex casual.

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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