First Online Hookup

by Nick

What’s your gender? Man
How old are you? 40s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? East Coast
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? 0

First Online Hookup

How long ago did this hookup happen? 20 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

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

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? We met online in a Usenet forum and we ended up chatting via AOL Instant Messenger and exchanging pictures. She was an extremely busty (36H) Greek woman (I’ll call her Aphrodite) with olive skin. One thing led to another and we talked on the phone. She said she hadn’t visited my city for a long time, so I suggested she visit. She said, “How about tomorrow?”, which was Saturday. The next morning, she showed up around 11 AM.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She knocked on the door and I let her in. We hugged, then kissed, and the next then you know, we were undressing each other as we talked. We both instigated it.

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? As I undressed Aphrodite, I was floored by how massive her breasts were. They were each almost as big as my head. Aphrodite was what I’d call “thick”, but not fat.

We started off kissing and I gave her breasts considerable attention. I made my way down to her pussy and laid her back and went to town. Eventually, she started to shudder and she caught her breath and said, “let’s fuck!”

I’d never experienced breasts that massive before or since. They were very heavy and pretty firm. I wanted to be one the bottom so I could play with them. I would never forget the sight of those massive tits swinging in my face as we went at it.

We started off with protection, but eventually, we just went without because she was on the pill. We pretty much fucked and slept until Sunday afternoon.

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? We talked on the phone a few times aftward, but she was in her 30s and I was in my 20s, so we didn’t have much in common.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Condoms, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Just happened, I don’t know why just went along with it

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? I spent a weekend fucking a MILF with huge tits.

What was the WORST thing about this hookup? I had to get a new mattress because we broke it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. Sometimes there are people you just want to fuck but don’t really have much in common with them, but that’s OK if everyone has fun.

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

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

What do you think about the Casual Sex Project? It’s a fantastic site!

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