by BestWeekend

Gender: Male
Age: Early 20s
Race/ethnicity: White
Location: North America
Highest education received: College degree (eg., BA, BS)
Occupation: Student
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

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Online Connection Gets Real

How long ago did this hookup happen? In 2014

How would you best classify this hookup: Sex with a new friend

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 met my partner on an online dating site, where we started talking. I was surprised at just how well we got along, as we talked about everything under the sun, found we shared many common values and attitudes and interests, and also that our senses of humour were compatible. I’ve never had such sustained and interesting conversation with someone I just met online before, and she is one of the best conversation partners I’ve ever had, period.

Before we met, I admired her and felt strongly connected to her on many levels. My opinion of her has, after meeting her, only improved.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had been playfully joking about visiting for a while beforehand, but after a few months talking online, we managed to line up a few free days in our schedule, and I went to visit her. She graciously let me stay two nights at her home, and when we met for the first time we explored her city together before eventually heading to her place. We spent a lot of time talking on the couch before she leaned in towards me and we kissed.

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? Over the course of the weekend we had sex several times, including oral and vaginal sex in a couple of different positions. We were quite compatible and generally both very satisfied, and though there were moments when someone got sore or when one partner or the other couldn’t achieve orgasm, overall we both had plenty of fun orgasmic sex, as well as lots of cuddling, watching movies together, and more.

I had previously had some problems achieving erections with new partners, and she knew about this beforehand and was understanding about it. The problems occurred again to some extent, though happily, it was less severe than it had been with any of my past partners.

I also performed cunnilingus for the first time with her, a new and interesting experience for me and apparently quite a satisfying one for her as well.

The weekend simply ended with me going back home, after we wished each other well and left open the possibility that we might meet again some time.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? One of the (many) things we talked about prior to meeting was our sexual history and health, and we were both quite certain we were clean (neither having ever had symptoms, or unprotected sex with partners of unknown history). We were both waiting on test results for recent STI tests we had had done, too, but didn’t wait for confirmation. She was using an IUD to prevent pregnancy.

What were your REASONS for having this hookup? I went to visit her initially just because I wanted to finally meet this person I had been having such excellent conversations with. I had thought there was a possibility that things might become sexual, and when they did, I was glad for it because I had indeed ended up finding her very attractive.

Were alcohol or drugs involved? If so, how much? We did drink at some point during the weekend, but we never had drunken sex.

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 returned to our separate lives, connected only over the Internet. There is the possibility that we will meet again in the future, and I hope that might be the case, but for now we have no concrete plans for a future, and have not discussed the possibility of a relationship, though distance of separation and a few differences in our long-term goals make a relationship unlikely.

I respect and admire her wit, intelligence, and humour, and definitely consider her to be a close personal friend at the very least.

I walked away from the weekend feeling energized, refreshed, happy and self-confident. It felt really good to spend time with someone I could connect so well with.

To whom did you talk about the hookup? How did they react? I haven’t talked to anybody about it.

Was this a consensual and/or wanted experience for you? For your partner? We were both rather coy about the possibility beforehand, but when we actually met face-to-face, yes, it was definitely something that we both wanted to do.

Do you regret this hookup? If so, why? Not at all!

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 worst thing about this experience was that I still had some erectile difficulties related to anxiety, but she was excellent at handling those problems and they weren’t as bad a problem as I might have feared.

Everything else about the weekend was wonderful. We had good food, great conversation, lots of fun sex and cuddling, and generally had a really good time. It was the best weekend I had had in a very long time.

Prior to this, I had only had sex in a relationship-like contexts. This experience has reinforced my belief that a sexual encounter with someone who isn’t necessarily a relationship partner can be just as fun (even more so), and can still be good for one’s emotional and mental health.

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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