What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
Highest education received: Post-graduate degree (eg., MA, MS, Ph.D., JD, MD)
What’s your occupation? Engineer
What’s your current relationship status?
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? Try-Sexual
How many sexual partners have you had in your life (including oral sex)? 70 ish
How many hookup stories have you here posted before? 1
How long ago did this hookup happen? 1 year
What was your relationship status at the time? Same as current status
How would you best classify this hookup? One-night stand
How long did you know the person before this hookup? Just met that day
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? Boredom got the better of me again. I was away on a business trip and I couldn’t be arsed going to a bar so I loaded up Tinder. Doris (not her real name) and I matched instantly, like within 4 or 5 swipes. Her picture looked OK but it was Tinder. You only believe half of what you see and none of what you hear. She was chunky. She was in the mode of saying that she was trying to give Tinder away because of too many bad experiences. I persisted and got the final message from her: “do you want to come over?” She told me to give her an hour as she looked like shit (in her words) so I waited, I showered and went over.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Luckily she lived only about 10 mins drive through back roads so I risked it and made it to hers. She wasn’t wrong. She was about 4’11 and had huge tits. She was just a big girl with a massive arse but she had a pretty face and smelt good. We sat down on her couch and had a glass of ‘wine’ (tasted like someone had rung a wet moldy tea towel out in the glass) and we got chatting. Quite a cathartic experience. Despite coming from opposite ends of the socio-economic scale we shared some common ground. She put her feet on my lap and I massaged her feet – had to start somewhere. We discussed partners. I told her that I had been living in Singapore for a while and her enduring comment was something like ‘Asian Girls – they have tight pussies don they?’ No alarm bells went off but given that she had had 3 kids I think she was getting her excuses in early.
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? It wasn’t long before she leaned over and we kissed – lovely soft kisses which in hindsight masked what was to come quite well. Her sofa was in full view of the outside world but she lifted her top and bra and freed her enormous boobs and seemed not to care. Plenty of groping at relevant crotch areas and general heavy petting ensued.
Then we went into the bedroom. She dropped to her knees and undid me and went straight into her mouth and I was rock hard. Off came all the rest of the clothing and there we were: strangers 1 hours ago and no discussion of sexual health but now butt naked, in a 69 position with me on top fucking her mouth. I had to stop doing this.
As luck would have it, her pussy was shaved and clean and tasted sweet and salty. I hadn’t cum for a few days so I warned her that if I came in her mouth that the volume would be impressive. She stopped sucking. We switched to her on her knees and she moved so I could feel her pussy and arse. She reached over and got some lube from her bedside table and put some in her arse and mine. She then proceeded to blow me with 2 fingers inside my bum while I played with her arse opening.
I came enormously and she had no chance. She nearly vomited with the volume and was taken by surprise when I went up to her and deep french kissed her with half of a big load of my cum all over her face. Between us, we cleaned up my cum and lay down for a breather. I kind of liked the taste of my cum but only when it was in another girl’s mouth – weird.
There was more talking going on and she asked if I liked her fingers in my arse – a bit late for that I thought. But I did like things in my arse, to which she reached over into the bedside treasure trove and grabbed a sizeable glass butt plug and just rammed it home – nice.
This had the effect of killing my erection; however, she now started to divulge what she liked and what she wanted. With the focus now off my cock, she turned out to be the instructor. She reached over and grabed the lube and gave a few pumps onto my hand. She rubbed it all in and kissed me, pulling away into a doggy position and she asked me to fist her.
I was no expert in this department but my god, her pussy was fucking huge. Once I got past the opening my hand fell into a void. I was able to fully clench my fist inside her and after about 5 minutes of this she just let out this magnificent moan and proceeded to dump about a liter of fluid all over me, the bed and her. I have never seen anything like this before. I have had squirters. I love squirters but this was Ninja level stuff. The bed was a swamp.
I was quite unsure what I was to do next. She rotated and lay on her back still twitching away and my arm still (seemingly) buried inside. Then she gave me the next instruction to her next kink. Verbatim ‘Fucking Choke Me’. So now I was: 0 – 2. Hadn’t fisted a woman before and hadn’t really choked one either. My cock by this stage was surprisingly about 1/4 of an inch. It had retreated and I thought the fact that my whole hand was where it would normally like to be kind of made it superfluous to requirements.
This choking thing. I was of the opinion from reading too many books that you could easily block off a windpipe with one hard clamp on one hand. I was therefore quite loathed to apply much force to which Doris barked at me. “Fucking choke me like a man,” then she was quite blue in the face and I guess I had fulfilled her requirement. She let out this enormous guttural moan, pushing my hand off her throat and proceeded to dump another liter of fluid. This time at a quite high velocity, onto the bed, the floor and the walls.
I extracted my hand from her and kind of did what I thought I could to bring some sensuality back onto the scene so I kissed her and we both covered in sweat. She was exhausted and just wanted to spoon. I pulled the butt plug out of my arse in an endeavor to spark some life into my todger. Spooning seemed to do the trick and although there was no way I was going to venture into the dimensionless cave that was her vagina. A pre-lubed arsehole was in close proximity.
I’m usually quite lucid when I fuck strangers. I like to observe what is going on and stay on my toes. We had never actually discussed her arse up until now despite her lubing it for some finger play as I was trying to weasel my (now almost erect) cock into it. Again Verbatim, “I have never had anal sex” in an abrupt and very clear instruction. So I stopped and remained in the spooning position. I dropped my toothpick into her grand canyon and said that I didn’t think I would be able to cum.
I stayed hard. She clearly was interested in some anal action and I asked if she wanted a butt plug first. She rose up on her knees and basically begged me to just fuck her arse. This was the start of kink number 3. I stood behind her and got the tip into her arse, asking if she was OK to which she let out another muffled groan and pushed back onto my now quite hard cock and said, “Now pull my fucking hair.”
So there I was: fisting, choking and now pulling her hair. The harder I pulled the more she swore. I was quite close to losing my load inside her and was genuinely balls deep on the downstroke. I asked if she was OK with my cum inside her arse and I gathered from the volley of abuse I was getting from her filthy mouth that anything was OK. I gave it my best shot and when I reached the vinegar stroke, pushing so hard and she collapsed face down and my cock came out. I lost the load all over her arse. Good result I would say.
That was me for the night, despite cleaning up and being given a very pleasant cleanup blow job. I could not top that besides that her bed resembled a workshop floor and there was sump oil everywhere. I wasn’t game to cuddle up in that. So I made my excuses and we talked for a while. She fell asleep and I gathered my bits and beat a hasty retreat.
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? I am very good at unmatching Tinder dates. However, on this occasion, I contacted her the next day and asked if all was well. I refused to accept her apology for making me do stuff outside my comfort zone. I was complicit as long as there were no scars I was OK. She was OK too, apart from some marks around her throat and a sore arse. A part of me would go there again. It was quite primal and we fucked for more than 3 hours all up which was long for me. But I think I would just pass. Tinder in Australia is a total fuck fest. You just have to strike up a conversation and despite the usual protestations of “I’m looking for something long-term,” my strike rate is greater than 50%. It never takes long and most dates I have had have been within 4 hours of meeting.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, Sterilization, I don’t know if my partner was on any (other) method, No penetrative sex happened
What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Intoxication, I was feeling lonely, Just happened, I don’t know why just went along with it, It was easy/convenient
How intoxicated were you? A small amount of alcohol or drugs, not enough to feel it
How intoxicated was your partner? A small amount of alcohol or drugs, not enough to feel it
How wanted was this hookup for you at the time? A little bit
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. Nothing to brag about. everyone is doing it.
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? I don’t know / I’m not sure
Do you regret this hookup? A little bit
What was the BEST thing about this hookup? Doris losing liters of fluid and the guttural moaning as she was doing it.
What was the WORST thing about this hookup? The mess afterward
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes – one day I will catch something. I have to change.
All things considered, how POSITIVE was this experience? Fairly positive
All things considered, how NEGATIVE was this experience? Not at all negative
Anything else you want to add about this hookup? God Bless Tinder
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? It is so prevalent. I don’t get the negative press.
What do you think about the Casual Sex Project? LOVE IT!
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