by Jakob

Gender: Male
Age: 44
Race/ethnicity: Caucasian
Current location: Brisbane
Highest education received: College degree (eg., BA, BS)
Occupation: Engineer
Relationship status: Married
Religious affiliation: Athiest
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20 ish
How many hookup stories have you here posted before? 0

17 Black

How long ago did this hookup happen? 7 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…)? One Night Stand

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? Valentines day – out with friends at a casino for a few beers and a flutter. Lost all my money on roulette but had a tab running so went with a mate and sat at the bar. That I cant remember this ladies name is by no way a reflection on how attractive she was – but I dont think we swapped names – maybe a nickname – its a blur. Very attractive 40 YO brunette, our eyes were drawn to a very nice set of fake breasts that cost 18000 (I remember that bit) – both me and my friend had a feel (at her request) and after a few cocktails she wanted to get back into gambling. She won about 4K in a short time and the cocktails were taking their toll.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went to the toilet, came out and she was there – she dragged me into the smokers lounge and threw herself at me – whispering how she wanted sex. Told me she didnt care if I was married (she wasnt) she just needed a man. At this point I told her that my friend was staying in my room (as he had drunk way too much) she seemed pensive but said nothing. Back to the tables she gave back about 1K in 5 minutes and I said I was hitting the sack (0430 by this time) expecting her to say farewell. For some ridiculous reason she wanted me to be her lucky charm and gave me 5 $10 chips – to cut a long story – I had 2 chips on 17 – and it came up. She pocketed the 700 – went to the bar – brought champagne – 3 glasses – off to the room we went. I clearly remember my mate asking if I wanted him to taxi home – I didnt care.

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? Back in the room (a suite) we necked some champagne – my friend excused himself and went to lie on the sofa bed thing – the lights went off but still plenty of light to see – and she was naked in a flash. Very tidy for a 40+ YO who said she had 4 kids. As she was naked first I payed homage to this magnificent pair buy sucking her nipples at the same time fingering her (beautifully manicured) pussy. I think she came loudly (probably on purpose) with my fingers inside her and I took the liberty of going down on her for another thumping orgasm – which when I pulled away was accompanied with a small squirt all over my face – which she apologized for and then proceeded to lick off me with plenty of deep kissing so I tasted her ejaculate – marvelous. I fully remember how sweet her pussy was – glorious. I was pretty hard by this time but wasnt my normal alabaster as I had drunken probably 30 Standard drinks over 5 hours.

I needed to pee and went to the bathroom – where I got my gear off – and of course she followed – as soon as I had finished she was on her knees delivering a sound blow job. I remember vividly, looking in the mirror at this goddess deep throating my cock. I didnt think I would come so quickly but gave her a throatload of my jism which she kept in her mouth and snowballed me with – dragging me back to the bedroom.

Back in bed – with my mate pretending to be asleep (neither of us cared) she sucked me hard once again then started talking about how despite having 4 normal child births – she prided herself on how tight her vagina was and proceeded to lower herself on my (now even softer) cock and work it back to full hardness. I had to have her pussy again so we switched to 69 and could see that her anus was freshly bleached and clean – proceeded to tongue her ass and inserted a moistened finger. Didnt get much of a response but she finished the 69 by grabbing my finger and sucking it and I vividly remember her saying – ‘an Ass man hey’

I have had plenty of anal sex – but I dont travel with condoms – she had none and it felt a bit risky. She begged for me to take her ass – said she was clean. What else was there to do. Magnificent – despite me not being as hard as I wanted to be. I asked if she was OK with my cum in her ass – between orgasms she said thats where she wanted me to cum.

I think around this time – with all the alcohol my head started spinning and after I came in her bum we fell into each other and crashed. I had a meeting the next day and my phone alarm went about 3 hours later. My friend was wide awake and looking at the carnage – obvious signs of some fairly brutal sex and a lot of come in and around her ass.

I had to wake her as I was checking out and we showered and dressed and she left.

Some high fives were exchanged as well as a few winces when I explained what happened with the anal.

Did you have an orgasm? Did your partner(s)? I lost count of how many she had (at least 5), I had 2 one in her mouth and one in her ass.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. I know I was clean – she smelled and tasted devine and was immaculate and groomed. She was a professional lady – I took her word. We both (I think) mentioned the word trust a few times.

What were your REASONS for having this hookup? One thing led to another – she was obviously in town for gambling and sex (valentines day) – I guess I was the lucky guy

Were alcohol or drugs involved? If so, how much? No drugs but a shitload of alcohol was consumed

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? After she got dressed (and my friend could look at her) she told me – in front of him – that she was clean – and infertile (despite me not cumming in her vagina) and not to worry. She gave me her phone number – told me to call her.

To whom did you talk about the hookup? How did they react? Only one other person knows about this – he watched the whole thing.

Was this a consensual and/or wanted experience for you? For your partner? Totally consensual – maybe felt a bit worried about unprotected anal – but fully consensual, raw, dirty casual sex.

Do you regret this hookup? If so, why? I got tested a month later and was clean – up until this time there was some consternation – I had no symptoms but was a little paranoid.

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 would love to have sober sex with this lady – she was heaven in bed – dirty, took the lead, begged to be fucked in the ass. The alcohol definitely was the worst aspect.

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

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

Anything else you want to add about this hookup or anything else? I called her later that day after my meetings – she was on a train back home. I went over a few things with her about possible hookups down the track – she was interested but it probably wasnt going to happen – thanked me for a good night. I told her my mate was awake for a lot of the night and watched us – she was cool with that. I even asked if she would be keen on a 3-way – to which she said she would have been last night but it wasnt really her thing.

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