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What’s your gender? Woman
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What country and/or city do you live in? NZ
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Co Director
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 50
How many hookup stories have you here posted before? A lot

New Year’s Day in a Fancy Suite

How long ago did this hookup happen? one month ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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? He is of average height, with very short brown hair and blue eyes. He trains hard in a fighting discipline so he has an incredible body – lithe, chiselled, muscular, amazing abs etc. He is good looking in a non-classical, slightly unusual way.

I met him online about 18 months ago, back in the early days of meeting men online. Even though my advertisement clearly stated I was looking for hookups, he kept inviting me out to eat. We ended up going out for coffees, lunches and dinners lots of times without having sex. I was bemused, but he is a nice guy who I enjoyed chatting too so kept going. Eventually we had sex one time, then he was gone overseas. Like the guy in the New Year’s Eve story, he also has a job which involves him going away for months at a time. We had sex a second time last summer, then over the last 12 months I just had the occasional online chat with him, then he reappeared back home and we had a coffee and arranged to hang out around New Year time because I had a free week.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We agreed to get together on 1st January, which was funny because the last time we’d had sex was on 1st January a year before. He told me to get organised to stay out overnight, he picked me up, and we went and checked into a hotel in the city. ( He usually pays for most of this stuff – normally I’m strictly 50/50, but he earns a heap and I’m a solo parent, so I let him pick up the big bills. Occasionally if I’m quick I can get in and pay for coffees or a drink somewhere).

When we checked in we got a totally random upgrade to basically the best suite in the hotel. It was massive, with heaps of different rooms, amazing décor and stunning views over the city and harbour. We were both really excited about that! We drank some champagne in the room, then went out for dinner. After dinner we had a swim/spa at the hotel pool, then finally ended up in our hotel bathrobes reclining on the couch with a glass of wine, looking out at the nighttime city lights. We decided to leave the curtains open as we were so high up there was no building where people might be able to look in on us.

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? He does this really nice thing at the start of sex, where he basically massages and strokes me for ages and ages, and it’s totally heavenly. He was stroking my whole body and he kind of positions himself where I can’t really reach him and tells me to just relax and enjoy it. After a long time of this, with me super blissed out, he starts just brushing past my pussy lips, not really touching me, just teasing, over and over until finally he touches my clit and by then I’m so wet and aroused that I’m shaking and when he puts a finger inside me I pretty much cum instantaneously. But what was funny was that when he did start to touch my clit, half the time he wasn’t, i.e. he wasn’t in the right spot. I had to kind of maneuver myself a little to get him in the right spot, but when he was there I came so fast it didn’t matter.

After that I turned around and kissed him and felt his amazing arms and chest and kissed down his body to his average sized, very curved – banana-shaped – cock. I kissed it, licked it, sucked it, swirled my tongue around, swallowed it etc. He was gasping and responding which made me think he liked it but then he seemed a bit uncomfortable. I remembered that our previous 2 times he hadn’t done any oral on me and I got the impression he didn’t like to do it, so I wondered if it makes him uncomfortable to receive it because he doesn’t want to reciprocate? Or else I was just doing a really bad job of it haha. Either way, I kept going for a while because I was enjoying it and tried lots of different techniques to see what he enjoyed, but I couldn’t really tell.

Then we fucked in missionary for a bit and his banana cock really hits the spot so it felt great. I thought that riding him would feel awesome so flipped him over to do that and it did feel great, but again he seemed a bit uncomfortable with the whole thing and didn’t seem to like me taking any initiative. I started to remember that last time I had also had this feeling of tension while having sex with him, like something wasn’t quite right. I thought it might just have been me feeling inferior as I have a normal body and he has the body of a Greek God. But then I realised that what it was is that he is completely silent and serious during sex. I always find it a bit weird when someone acts totally different during sex – when we’re chatting he is funny and smiley. And I have to say I prefer sex that includes laughs and smiles and lots of talking. It was all just feeling a bit unnatural or something. We went back to missionary and he was obviously going to cum and when he sped up his banana cock was doing all the right things and I came again, and then he did. He looks a bit embarrassed when he cums and he certainly doesn’t let go and express satisfaction. I’m starting to think he has a sex hangup of some sort. Like he wants to have sex but he’s a little squeamish about it or something. The fact he doesn’t know exactly where the clit is and doesn’t want to get face to ‘face’ with it seems to me to indicate some kind of issue with it.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We went to bed in our ginormous suite bed, had a bit of a cuddle then off to sleep. We slept in quite late and didn’t have much time in the morning so had a short kiss and cuddle then had to get up and out.

We’re still in touch as much as normal. After this time I’m not really sure where this is going. I did enjoy the sex but at the same time find it a little weird. I’m not sure if I want to have sex with him again at this point. I do like him though and consider him a friend.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Well quite a few friends knew I’d had a week to myself and asked me if I’d managed to organise some fun. I told them I’d had sex 3 times in the week with 3 different people because it was true. I think a couple of my friends were a bit shocked by that. I also told them all about the amazing suite and showed them some photos. No-one asked for any detail or more information about the sex I’d had.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The massage/stroking thing he does is SO SO good. Enjoying that in our fancy suite while looking at the view felt pretty fantastic.

What was the WORST thing about this hookup? that I feel a disconnect with him during sex, like he is holding something back and is not relaxed.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

You have a hookup story to share? Submit it here!