by Jacrou

Gender: Female
Age: 45
Race/ethnicity: Caucasian
Current location: New Zealand
Highest education received: College degree (eg., BA, BS)
Occupation: Company Director
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)? 31
How many hookup stories have you here posted before? 6

My First Time


How long ago did this hookup happen? 26 years ago

How would you best classify this hookup? Friends with benefits

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? I was 19 and just starting my second year of university. I was still a virgin and was kind of annoyed about it.  I’d been wanting to have sex since I was 16 but it just hadn’t happened.  I’d had a boyfriend for a while but he wouldn’t do it, just fingering. I’d thought all that would change at university but it hadn’t. This wasn’t unusual in my peer group.  Nearly all of my friends were virgins and while we had lots of male friends and we all hung out in a group, no-one was really dating. (one of those guy friends has since told me he desperately wanted to date me or one of my friends, but was too shy to ask, so I don’t know maybe everyone was all awkward and shy?  I certainly wasn’t asking either, I was inexperienced and had no way of knowing if someone was interested in me or not).

Anyway, there was this one guy in my wider group of friends who had started something up with me, but we had not had intercourse.  He was a privileged rich guy, with exactly that look, good-looking, always smiling, smart and sporty, perfect manners and confident.  It started one night when we were all sleeping in some holiday house somewhere lined up in our sleeping bags and he was beside me and just turned over in the dark and kissed me.  No-one knew.  I was totally surprised and had not seen it coming. I was not very confident and felt nervous, but he was a superb kisser.

Over several months since that secret kiss, things had developed between us to the point that I would visit him at his house (always his house – he lived in a huge house with lots of room, I lived in a small suburban house), go down to his basement with him, and we would make out.  He said he didn’t want to have intercourse because he had had an incident with his former girlfriend where the condom broke and he was petrified of getting someone pregnant.  But we did pretty much everything else.  So by this stage I had become a 19 year old virgin who was having rather wonderful regular oral sex.  He was very very good at it along with kissing and caressing etc, and we both regularly had orgasms together.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On this particular night, some months down the track, my parents were going away and I decided to have a small party at my place for about 10 of my friends, a mixture of girls and guys.  It ended up being a slumber party and everyone came in their pyjamas and it was quite civilised, we had a few drinks and some food, watched some movies etc.  It is very indicative of the kind of scene we had, that this was a bunch of mainly 19 year old virgins having a sleepover and there was pretty much NO expectation that there would be any kind of hookup thing happening with anyone. 

Around midnight everyone went to sleep, most of them mainly in the lounge, but some girls in my sister’s room and some in my parents’ room.  I went into my own room and in my own single bed that I had had since I was a kid and basically rolled over to go to sleep.  I did not expect to see him as he was pretty cautious about keeping our thing secret and nothing at all usually happened when others were around. 

I must’ve fallen asleep because I woke up when I felt him climbing into my bed.  We started kissing and then he said that he wanted to do it tonight, he wanted to be inside me.  I was thrilled as I really wanted that too.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? So we undressed each other quite slowly, and then he got on top of me and very slowly entered me.  It didn’t hurt at all, I felt no pain and then we had sex, trying to be quiet.  It felt really wonderful, I enjoyed the feeling of having him inside me and he continued to kiss me and touch me.  Because it was a new feeling and very exciting I came easily, and then he did. He stayed with me for quite a while, cuddling me and asking me if I was OK, and what I had thought etc. I was happy. After a while he went back to where he was sleeping.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I had recently been put on the contraceptive pill by my doctor to control heavy periods because I had anemia.  I had told him that. We didn’t use protection.  I was a virgin, and he had had sex with one other person, using condoms.  I was pretty sure that that was correct.

What were your REASONS for having this hookup? Attraction, opportunity, wanted to experience having sexual intercourse, wanted to lose my virginity.

Were alcohol or drugs involved? If so, how much? A small amount of alcohol.  Not much.

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? We continued on the same way we had before, as secret Friends with Benefits, but now we had penetrative sex too.  We were part of a group of friends who did lots of things together, and then alone, he and I had sex together.  I was reasonably happy with this situation.  He was a very very good lover and sex was very satisfying with him.  He could also be a bit annoying with his attitudes, coming from quite a different background to me and I could see that we maybe wouldn’t work as an actual couple.  I was aware though, that the primary reason he wanted things kept as a secret FWB thing, was that I wasn’t good enough for him, in the sense I came from a lower socio-economic background, which was evident I guess in how I dressed, did my hair, spoke, acted etc. Even though I didn’t really want to be his girlfriend, it annoyed me that he didn’t think I was good enough to be publicly with, even if he was happy to sleep with me regularly. 

I felt ecstatic afterwards because it was something I really wanted and I really enjoyed it.

To whom did you talk about the hookup? How did they react? I told my best friend. She was also in this group of friends and was I think the only one who knew about what was going on.  Her reaction was part thrilled for me, part insanely jealous, so jealous that she went on a hell-bent (and successful) mission to lose her own virginity asap.

Was this a consensual and/or wanted experience for you? For your partner? Yes and yes

Do you regret this hookup? If so, why? Not at all.  I look back on this with great fondness and I think I was really really lucky to lose my virginity in these circumstances: in a place where I felt totally secure, with someone I knew intimately and felt comfortable being naked with, and when I was really ready for it, being old enough and with some sexual experience to ensure that it wasn’t painful and I was able to enjoy it and orgasm.

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 having a positive first experience of penetration.

It wasn’t really bad in any way, except perhaps the mixed feelings I had about my partner wanting to keep it secret.

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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