Older Man Hookup



What’s your gender? Woman
How old are you? 23
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Auckland New Zealand
Highest education received: Some college (not currently in college)
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? 0

Older Man Hookup

How long ago did this hookup happen? 7 months

What was your relationship status at the time? Single

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? He was a much older man (I’m 23, he was 53). It was a tinder matchup. I wasn’t really attracted to him but was horny and ready for a hookup. We met up at the local mall (I had just been shopping and brought new bras/panties) and had dinner. My mind was not really on him, but we kept chatting. We went for a walk down the beach then back to his place.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Went back to his house and did the normal small talk. We started watching TV. He then turned the conversation to my shopping bags, wanting me to try on my new underwear and model for him. I had had a couple of drinks by this point so was ready for anything. I showed him a few different sets. He pulled me close to him, and we started making out.

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? We went and laid on his bed. I spread my legs. I have had sex a few times lately but nobody had eaten me out in ages, so I thoroughly enjoyed when he did. He managed to make me cum. Then he laid on me and penetrated me in missionary. He just went straight in – not slowly at all. I had asked him to wear a condom but he said he hated them, he would pull out and it would be fine. We did it in multiple positions all over the house – missionary, doggy, standing, cowgirl etc. I should also mention that he has housemates who were out at the time. I was riding cowgirl on the couch when a housemate came in me. He wasn’t concerned at all.

We went to his bed. I ended up having sex with him again the next morning where he managed to ‘accidentally’ stick it in my ass while fucking doggy. I let him cum in there since he was already inside. I went to leave by myself as he had no interest in seeing me out, to find his housemates had found my underwear and neatly placed it on the couch. I met him again a few days later, semi regretting it as he was a bit of a dick but was keen for sex. We ended up fucking (including anal) in the dunes by the beach. I got another unwanted creampie, so I left and went to get plan b.

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? After the second hookup, he texted me a couple of times then proceeded to completely ignore me. I wasn’t phased as he ended up being a dick, and I had found someone else on tinder. I had completely forgotten about him until I ended up finding out I was pregnant and the dates matched up to him. He still does not want to know me.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

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? A friend in our weekly catchup about current flings.

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? A little bit

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? Somewhat

Why do you regret this hookup? Currently 7 months pregnant to a guy who wants nothing to do with his child or me.

What was the BEST thing about this hookup? Experienced outdoor sex for the first time, and first anal creampie.

What was the WORST thing about this hookup? Unplanned pregnancy

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Always on birth control.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Plan on raising my child without him

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? Casual sex has its place but has played a huge role in my life.

What do you think about the Casual Sex Project? Love hearing other peoples stories!

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