Anal First Night

by Huck Finn

What’s your gender? Man
How old are you? 33
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
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? engineer
What’s your current relationship status? Single
Religious affiliation: spiritual
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50-60 (can’t recall some names)
How many hookup stories have you here posted before? 0

Anal First Night

How long ago did this hookup happen? a month

What was your relationship status at the time? Same as current status

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? Blonde, really pretty, above average height, nice ass, and very easy going “country girl” personality. Met at a bar through a friend of hers that had been interested in me in the past. I knew when I met her that I’d rather be with her than her friend, at least sexually. We had a few beers, and it got late and I had things to do next day so was going to bounce. She came up and very eagerly asked me if I was coming to the next bar with them. I couldn’t say no, and so the night went on and on until we were dancing at the last bar together and starting kissing. Her friend got really drunk and went home so I told her I could give her a ride home. My house wasn’t too far away so we walked home a mile or so and then showed her my place.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was at my place, we were alone, and had maybe a 4-5 beers each earlier in the night. It was completely unplanned. I instigated it by kissing her on the couch but she had kissed me on the dance floor earlier.

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? We sat on the couch and started fooling around again. She said she had to go, and I said sure I can drop you off. Then she made a comment about my bed being comfortable, so I said, “Why don’t you go lay on it and try it out?” It seemed like an invitation and I joined her. Then we started making out again, with some ass grabbing. I went under her shorts and started fingering her. She responded very positively to it. She said she had to go again, and I said alright I’ll drop you off. Before we could get out of bed we started making out again, this time the fingering became more aggressive, and she grabbed my cock and started stroking it under my shorts. I took off my shorts and she took off hers. I could sense the excitement and I penetrated her on top without a condom at first. She was rubbing her clit and her vagina became extremely tight. I was going to come so I went for a condom by the bed and then put it back in. I came a few minutes later, on the shorter side for me, but her vagina was just too amazing and the excitement got to me. She said she had to go again and I said sure lets go, but then again, we started kissing and I became hard again and got on top of her from behind as her face was in the pillow. I went inside her again and she started moving her hips in a circle. It takes me forever to come a second time so I tried something. I put a finger in her butt and she said it felt great. She started rubbing her clit again and I went for the lube. I put some lube in her ass and then started having anal sex with her. She was loving it more than any other girl I had ever met before. She said she was close to coming but before she could I came in her ass.

On the drive home (in retrospect), she kept bringing up restaurants in town and I kept saying how great they all were. I was in such a stupor I didn’t realize she was trying to get me to ask her out to dinner.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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 couldn’t stop thinking about it for several days. I was pleasantly surprised that a girl that seemed so sweet and innocent would have anal sex and enjoy it so much. I’ve had girlfriends in the past that would never want to do it. Later on I confirmed that she was quite the party girl. I was also not really looking for a relationship at the time anyway. She texted me a week later but I didn’t go back for seconds because I didn’t want to get hooked on something that didn’t have a finish line. She was hot, sexy, good in bed, nice personality, but socially didn’t seem like someone I could see myself with in the future. As I’m getting older, I’m trying to at least focus on goals which are a long term wife.

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, Attraction to partner(s), Learning new things, experimenting, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Not at all

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? A few friends, they were not surprised. Maybe a few were envious. One friend knew her best friend, and during a conversation one night, the girl had mentioned she loved anal sex and was disappointed more guys wouldn’t try it with her.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Spontaneous first night anal sex.

What was the WORST thing about this hookup? I knew I couldn’t have a long term relationship with her so it was a tease.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I probably do too many random hookups and need to focus on what I truly want deep down ( a relationship) instead of just impulsively going home with girls after drinking which leads to nothing and just exhaustion most of the time. In general I feel poor about it the next day because I’m hung over and I have no intentions of seeing the girl again. In this situation, the spontaneous anal sex made it an interesting experience.

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? It has a time and place. I broke up with a serious girlfriend 3-4 months ago and casual sex numbers have increased to 10-20 in last few months. Girls have been relatively attractive to very hot, some interesting and some dull. There’s a time and place for everything. In a way, it’s an evolution back to realizing casual sex doesn’t lead to anything substantial or lasting. I’ll grow tired of casual sex, and find a girl again that I can build a relationship with in the future.

What do you think about the Casual Sex Project? it’s great!

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