That First Time



What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Aus
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0

That First Time

How long ago did this hookup happen? 8

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Sex with an ex

How long did you know the person before this hookup? For more than 3 years

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 dated for about 6 months, never moved beyond kissing and our clothes always stayed on. The relationship had fizzled out. We’d known each other since childhood. Shannon was a petite brunette, with cute little boobs and pale skin

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were doing tech support for a stage production and Shannon had stood in front of me while I was working on a light rig. She was maybe 30cm from my face. I looked up at her and made eye contact. She made a joke about me being on my knees in front of her.
“It should be you on your knees,” I said
“All you have to do is ask” she retorted and walked away. After some texting back and forth, we talked about how we were both in separate relationships and it would need to wait.

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? I was dating a busty girl who was a real tease. A date with her left me very aroused, but completely unsatisfied. She’d also made clear we’d wait to have sex. The next morning, Shannon and I were working alone again on the light rig. We were bantering back and forth, and I used the time old comeback
“suck my dick”
Shannon looked me in the eye
“I’ve already offered”
She stood up and walked into the male toilet and I followed her in. We stood awkwardly for a minute until she asked if I was sure. I said yes and she pulled my shorts down. I was already hard as a rock.
She took me into her mouth, and it was the wettest, warmest sensation I’d ever experienced. After I was getting close, Shannon told me to tell her when I was going to cum. I was pretty much there and told her so. She started swirling her tongue around my head, and I orgasmed, coming in her mouth. She stood up and walked out without saying anything. I was worried I’d done something wrong, but things were back to normal pretty quickly. For the next month or so, Shannon would give me head whenever we were alone.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? Shannon kept giving me head whenever we had the chance to be alone. We were both still in relationships that weren’t progressing the way we wanted. Eventually, we went further but that’s another story.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

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? Somewhat

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? I’ve never told anyone

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 received my first blowjob

What was the WORST thing about this hookup? It was the first time I cheated

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes – my first experience was casual sex, and I think this made me much more open to it

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

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

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