First Casual Hook-Up

by Colin

What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA – Kansas
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Lawyer
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 0

First Casual Hook-Up

How long ago did this hookup happen? 15 years ago

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? “L” and I met online. In those days, internet dating and hooking up was just getting going. I was single, heartbroken, and sexually frustrated over a recent break-up, and I was really, really needing to get laid. I had sent messages to a lot of profiles and never heard anything back. Suddenly, L responded. We didn’t talk all that much online. We did a little flirting, but mostly just set logistics. I went to her apartment on the night we had decided upon, nervous, but excited. No photos had been exchanged, so I had no clue what awaited me. I knocked and she opened the door. She was huge. Very, very plus size. I’m no Greek god, but I’m not this big. I didn’t want to hurt her feelings though, so I played it off. I took her out for dinner. We chatted about everything. She was very sweet but very talkative. I was surprised actually, at how open she was about things. I was trying to be discreet and just made up crap about myself to satisfy her questions. Finally, we went back to her place. We had both been clear beforehand that we both expected to have sex.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We entered her apartment and laid down in front of the tv. We watched a few minutes before finally, I made a move. We made out before, at long last, clothes began to get peeled off. I began sucking her nipples, which were on her huge breasts, and fingering wet pussy. I was rock hard and my cock was pulsing.

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? Finally, she orgasmed from the fingering and clit play and was red and flush. Then she smiled and said it was my turn. She went down on me and began sucking with some considerable skill. I was very inexperienced and really hadn’t gotten a good or enthusiastic blow job before. What L lacked in good looks, she made up for in enthusiasm. She sucked like my cock was made of candy. Finally, I was close to orgasm and told her, assuming she’d hop off and finish by hand. Nope. She kept going at it even harder. I blew a huge, pent up with frustration, load in her mouth. It felt like I was expelling 10000lbs of pressure. Once I had stopped, she sat up smiling, showed me my cum on her tongue, and gulped it back like a shot of liquor. All I could say was “woo”.

We rested and she chatted endlessly over shared stories before I started sucking her nipples and rubbing her clit again. My cock sprang to life hearing her moan. She had informed me she was on the pill, so I went for it. I entered her pussy and get started going at it. First in missionary, then she went on top, then doggie. Finally, back to missionary, and I unloaded this one in her pussy. We slept naked. I woke up to her stroking me, and we went at it again sometime in the middle of the night. I again came inside her after she quietly whispered in my ear to fill her pussy with my cum. I think that sent me over the edge before she had even finished the sentence.

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 morning, I had to rush off to an appointment. I showered and left with a peck on her lips. It was a tad odd, honestly. I wish I had more time to sort of disentangle each other, as the fast exit made it awkward, but I wasn’t lying. I really had an appointment. She emailed me a bit, but I soon went back to where I was going to school as summer had ended. We quickly lost contact.

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

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? This right here is the first time I have ever spoken of 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

Why do you regret this hookup? Just general guilt about using her to get off and get out frustration with the recent ex-gf. That said, L knew what the expectations were.

What was the BEST thing about this hookup? One of the few times I’ve been given a blow job to completion. It was very intense. It’s not just porn that makes guys like this. It seriously physically feels more intense to cum in a mouth or vagina.

What was the WORST thing about this hookup? I was conflicted in how I felt about it all. I honestly wish I had gone back for more. She was asking me to, but I just didn’t know how I felt. I wish I had. She was good at it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really.

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

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

Anything else you want to add about this hookup? I’m glad I didn’t act like an ass when I saw she was big. She was a sweetheart and gave me a great memory.

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