First Time

by armorer

What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Some college (not currently in college)
What’s your occupation? sales
What’s your current relationship status? Engaged/Married (open)
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)? more than I can remember
How many hookup stories have you here posted before? 0

First Time

How long ago did this hookup happen? 7 years

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

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? She was a trans woman I had met online.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We messaged each other online and it led to texting. I was living several states away from my GF at the time. I was over worked and feeling really horny.

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 sucked her off. It was my first blow job where I knew who I was sucking. She had a long, and fairly narrow cock. I was able to get her whole cock in my mouth and lick her balls. She came in my mouth, and I swallowed every drop. Eventually I wanted her to take my anal virginity. She did… it was amazing! We fell asleep, and the next morning, I woke her up with a blow job, and she fucked me again, filling me with her cum.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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 saw each other a few times after that. She had started hormones, and was unable to fuck me like that ever again, but she was still my first.

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, Attraction to partner(s), Learning new things, experimenting, To feel better about myself, I was feeling lonely, Submission / Relinquishing power, Making new friends

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? I’ve talked with a few people about this. My female friends enthusiastically approve. My male friends react with disgust.

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? 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? having my virginity taken with enthusiasm
learning that I REALLY liked getting fucked in the ass
I can give good head.

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I am comfortable with more sexual options.

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!