Fun Or Run

by Jakob

What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Darwin
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Engineer
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Tri Sexual
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? 2

Fun Or Run

How long ago did this hookup happen? 12 years

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

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? It started at a bar. I was out with a work colleague, and I saw D all dressed up with nowhere to go. She was with a girlfriend who was hitting on my drinking buddy. I thought nothing of it; I just thought it was good banter and nothing overtly sexual. She was fit, in her early 40’s, was wearing very conservative clothes, was short, a bit tubby, but a really nice and a laid back demeanour. I would have to say that there was no real tension there until her friend made a big play on my friend (grabbed his cock) who politely made his excuses, and then we left for a nightclub.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Well, they followed us – surreptitiously of course – and we met again in the club. This time though, her jacket was off and through her white top, her nipples were visible and erect. I made quite sure I brushed them rather obviously when I asked her what she wanted to drink; she rubbed back and gave me that look. There was a group of 10 or so of us now drinking and chatting on the mezzanine floor watching the 18 or something year olds do their grind on the dance floor. I grabbed her hand and asked if she wanted a foot massage. She definitely did not know how to handle this request, so I left it there. She grabbed my phone, put her number in it, and said, in the time old tradition, ‘Call me later.” After a few more beers and a few more shots, I went home with my buddy and contemplated my next move. Once back in the room, I just sent the short SMS reading, “Still fancy that massage?” Now, I understand the time and mobile phone networks of the early 2000s, and within milliseconds I got the reply reading, “Thought you would never ask.” So I got back into my clothes, and we met on a pier that was about a 10-minute walk from my hotel. She sat down – still had full stockings on – and I gave her a foot massage for an hour and invited her back to my hotel. It was all going well.

Out of nowhere, she said, “You are married aren’t you?” I owned up, but to this point, nothing really to report. I had brushed her tit, massaged her foot, and clearly, the banter was leaning toward fucking each other senseless later on. I don’t know why, but I just said to her, “That’s my issue, and you can do what you like.” She spread her legs apart a bit, and I put my hand on her soaking mound, with her stockings still on, and rubbed her gently for a few minutes. She got up, grabbed her stuff, and called a cab.

I remember her parting glimpse over her shoulder; it was one of overt flirtiness, as well as a ‘come fuck me’ look, but I didn’t follow her. Instead, I had lost a very large load all over my hand about 10 minutes later.

The next morning I bided my time and waited until about lunchtime to send her a single line text message saying, “Hey Babe – what’s it to be ‘Run or Fun?'” Again, the millisecond meter wasn’t at 1000, and the reply was there – FUN – followed by an address.

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? I drove to her place and very strangely, she had a girlfriend with her. They were having a bite of lunch. D had a short skirt and Camisole top on with no bra and a loose linen shirt on top. It was incredibly provocative. I went (for the first time) to her and kissed her on the cheek and squeezed her arse. Her friend looked on – not at all awkwardly – meaning D had clearly planned this all out. I sat on her couch while she finished lunch, and then D came over to me and leaned over. All was hanging out to see, and she had a spectacular set of tits, might I add.

I looked over to her girlfriend and asked if she was going to stay and watch. She was keen – no question – but I think D had already said a few words to her. So, she picked up her stuff and left. Bummer.

D came over to me again, but this time she unbuttoned my jeans and just swallowed me whole in one go. I told her that this tension wouldn’t see me last long, and she looked at me with her big blue eyes and sucked for all she was worth. I jettisoned a very large load down her throat, which she swallowed mostly, then came up and kissed me. She then grabbed me by the collar (as if it was a dog collar) and led me up her stairs – but stopped on the landing and took off her panties. She laid back and pushed my head between her legs. My god was she wet. I drank from her for about 10 or so minutes, and she came/squirted all over my face as I got hard again. We then went to her bathroom, and she turned the shower on. She then proceeded to wash me and her – her arsehole, my arsehole – and there were lots of fingers and lube. I was pretty into it.

We then made our way to her bed, which was interesting. She was clearly a cat and pillow lady, and her four poster bed was a mess – no other way of putting it. But, we found room, and she straight away pushed me onto my stomach and stuck her tongue in my arse – very horny. I, of course, repaid the compliment and tongued her pussy (which by this time was a dripping mess again) as well as fingered and tongued her arse.

To say that the thought of “this is going well” didn’t cross my mind would be a lie. This was one very dirty but very posh chick who knew what she wanted. We fucked and sucked and stuffed various toys into each others’ orifices for about 3 hours with no break. I came inside her arse, her pussy, and her mouth. She hauled me back to the shower and proceeded to piss all over my neck and face whilst I fingered her arse again.

After the shower, we laid on her bed, and I recall that she got up and opened her curtains for all the street to see her. She then came back over to me and proceeded to fuck my face – with her naked body upright for anyone walking past to see.

It was and is to this day the best first-time casual sex I have ever had. D knew what she wanted and knew how to play me. She was assertive, vulnerable, filthy, sensual, and a voyeur whenever she needed to be; she played the part well.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? In the afterglow, we were buzzing and were both exhausted and fell asleep in a pile on her bed. I had a dinner to attend, so after a couple of hours of entwined rest, I made my way to the bathroom for a shower. D laid there and watched me – clearly satisfied – freshly fucked – looking awesome.

Our clothes were strewn from one end of her house to the other. The carnage (pools of mine and her cum) were everywhere also.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, Submission / Relinquishing power

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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

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

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

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

To whom did you talk about the hookup? How did they react? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Just dirty, consensual sex. We just went with it, her motives were clear, and we both got into it. She wasn’t phased with anything that happened – just went with it.

What was the WORST thing about this hookup? That her friend didn’t stay and watch/join in.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all – this is the sort of casual sex I dream about. Happened once.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? We continued to see each other from time to time for a year or so – usually at night when we were horny. We never reached the dizzying height of this encounter, but we did take the sex outdoors. We made love for 2 hours on a beach outside where she lived at midnight, fully aware there were eyes on us. She loved to finish a session by pissing on me. It was glorious.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Get into it – I think we are programmed to be polygamous – as long as no one gets hurt.

What do you think about the Casual Sex Project? A great forum.

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