First Time Anal

by Dj

What’s your gender? Man
How old are you? 27
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
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)? 30+
How many hookup stories have you here posted before? None

First Time Anal

How long ago did this hookup happen? 5 years

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? For less than a week

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? I met him on Scruff. He was 41 and I was 22. I had met him the day before and we continued chatting.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began on Scruff. I had posted a Craigslist ad trying to find someone to take my anal virginity and downloaded Scruff and Grindr. I met him on Scruff, and we talked for a day. The next day, he invited me over after I left work.

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? When I went to his house, he had the door cracked. I went inside and found him on his bed masturbating. I undressed, went in, and started performing oral sex on him. Then we started 69ing. He started to eat my ass and finger me. Finally, he lubed me up, put a condom on, and eased his cock into me. It hurt a little at first but he was just the right size for it not to be too painful. Eventually, it felt amazing. He pulled the condom off and came all over my stomach. Then, I put a condom on and fucked him

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? I felt alright. I wanted it again lol

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, 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? 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? Relatively positive

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? It was just magical. It felt like a penis is meant for an ass.

What was the WORST thing about this hookup? It didnt happen again

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!