First Time in Two Years

by Hermes

What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? New York
Highest education received: Some college (not currently in college)
What’s your occupation? Media
What’s your current relationship status? Single
Religious affiliation: Non specifically spiritual
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Voyeur, Adventurous
How many sexual partners have you had in your life (including oral sex)? 50 approximately
How many hookup stories have you here posted before? 0

First Time in Two Years

How long ago did this hookup happen? Last Night

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? She is in a committed open relationship. She has an average face with a thin/athletic build and a vivacious personality. Shortish wavy brown hair cut above her shoulders. A (maybe B) cup breasts. Self shaved labia. Medium sized clit. Small lips. Her personality was her best asset. We were both at a bar and I had actually closed my tab when I saw her making eyes at me across the bar. I had a recent break-up and was in a pretty lonely place emotionally with my ex and my anniversary coming up this weekend, so at first I averted my eyes. Then I had a second thought and figured even if I was shot down I had nothing to lose. I went over to her and we started small talk very quickly about religion and philosophy. We had a gregarious chat rolling over several topics and I can tell that we are getting along. Eventually we got to discussing relationship status and it turns out she was in a long term open relationship. I took this as an invitation and began to get a little closer and begin touch her thighs.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We continued talking and laughing and got another drink. In the process of drinking our wine and chatting she puts her legs in my lap. She whispered in my ear how nice her pussy is. I shifted closer to her and reached two fingers into her shorts through one of her pantlegs. I rubbed my fingers against the outside of her panties against her labia and then eventually moved her panties aside, felt her wetness and slid my index finger inside of her. We continued to talk and chat for another 10 to 15 minutes while I finger her off and on. At a certain point she texts her partner that she was “going to get fuckt”

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? At an early (for NYC) last call we left the bar. She left slightly before me by like a minute. When I met her outside I kissed her strongly, which aside from a peck was our first real kiss. While I kissed her I reached down and slid her left breast out of her bralet under her half unbuttoned shirt and bit her nipple and teased with my fingers. I asked her to keep her breast out under her shirt and she walked the two blocks back to my place like this while we discussed what we wanted to do with each other. She focused on wanted to get fucked while I told her I wanted to go down on her for a while.

Once we arrived at my place, we walked into the bedroom and I undressed her, folded her clothes and placed them in the corner. After she was fully undressed. She asked if I had condoms. I placed a few in the bed because it makes it a little difficult for me. I then undressed, got on the bed and proceeded to go down on her. I started with a lot of long licks to her inner lips and alternated to clit play. When I licked her clit I would stiffen my tongue and sort of snap her clit against my tongue. This got her really worked up and she asked for me to put on a condom. I demurred and continued going down on her like this and fingering her vagina and eventually rimmed her ass double penetrated her with my fingers.

It always takes me a while to get aroused but by now I had a semi. I smacked my cock against her pussy until I got hard and tried putting on a condom and lost my erection. I went back to oral and digital and got her really worked up. Eventually I was hard again and was rubbing against her again. This time she grabbed my bare cock and asked me to fuck her. I told her about not having a condom on and she just pulled me inside of her. We fucked missionary, she rode me to an orgasm and we spooned for a half hour before she asked me to come. I wasn’t sure I could so I pulled out and finger her some more. We took a break so she could piss and she sucked on me while I watched her piss. I stood back and masturbated while she sat on the toilet cleaning up. We went back to bed and fucked missionary after applying some astroglide and I finally pulled out and came. We lay around and chatted about the sex and her rules for no further contact. She complimented my cock and my skills as a lover and I complemented her body and technique. We both discussed how sex is better in our 30s and how we had made a good physical match and had a good fuck. All of this talk got me worked up again so we fucked doggy and missionary for another few minutes until I came again. After that we cuddled & chatted. I told her that the whole episode reminded me of the Rhianna song “Needed Me”, which I then played for her. I thanked her for the release and ego boost while we dressed and then I walked her to an Uber and out of my life. From meeting at the bar to her leaving was probably four really amazing hours.

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? It’s odd, I was actually reading this site earlier in the evening and thinking contextually about having more hook ups. I’ve been mainly a serial monogamist but have had some periods of being single. I am happier in relationships but always feel that I end being single too soon. Now I am single again and worried about being too old to be single. I’ve had a couple of make out sessions and got to third base in the past few weeks but was worrying that my time had past. I got turned down for a date earlier so I was feeling lonely and even went to a show alone, just to think. This episode was a great rebuttal to all that. My partner was very specific about not exchanging contact and mentioned that she doesn’t hang at that bar so I am cool with that being that. That said, it was an amazing life affirming experience and we both made each other feel good and exchanged opinions that will make us better lovers in the future.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, Intoxication, To feel more confident, I was feeling lonely, Power / Dominance, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

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? Just you guys so far 😉

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? A little bit

Why do you regret this hookup? I wish I was better at and more satisfied with using condoms.

What was the BEST thing about this hookup? The spontaneity and eroticism. The public/outdoor play, foreplay and variety of positions.

What was the WORST thing about this hookup? n/a

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? In the short term I feel more confident

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

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

Anything else you want to add about this hookup? It was super interesting to have someone who was on the same wavelength about all of the public play and randomness. This will definitely be one of the benchmark encounters of my life.

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? I wish there were less hang ups and more communication but I think this is getting better and less of an issue in NYC thank most other places.

What do you think about the Casual Sex Project? I think this is a great forum and safe space for sharing. It’s nice to read opinions of the all genders and orientation, especially women.

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