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What’s your gender? Man
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? New York
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Management Consultant
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Jewish
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? Around 30
How many hookup stories have you here posted before? 0

Sexy Older Attorney

How long ago did this hookup happen? 3 Years Ago

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? 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? I met Amanda (not her real name) while I was out for happy hour with some friends from work. Amanda was in town on a business trip and was hosting a professional event at the bar we were at. She was in her early 30’s, average height, black hair, with a fit build. She looked fantastic naked.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Her work event at the bar was wrapping up when we first started talking to each other. I was with a friend from work who happened to be really drunk and made a rude comment to her which I apologized to her for which she appreciated. Once the event was wrapped up on her end, we started talking more and eventually started making out. She was staying at a hotel nearby and invited me to come back with her for a drink. We got to her hotel and had a quick drink before she suggested going up to her room.

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? After leaving the hotel bar for her room, we started making out again in the elevator. Once we got into her room we continued making out while trying to take our clothes off. Once we were naked, I started fingering her while she played with my penis. After a while, I started teasing her by sucking on her breasts/nipples which were absolutely beautiful. She had a firm B cup, perfect for a handful with perfect, pink nipples.

After sucking on her nipples for a while, I started slowly kissing her entire body until I got down to her vagina. At this point she was absolutely begging me to fuck her but I held off and started eating her out which made her go absolutely nuts. I ate her out for about 10 minutes until she had an orgasm. By now, I was rock hard and she was eager to please me, so she pulled me towards her face and started blowing me. I didn’t want to cum so after a few minutes I pulled out, and I slowly entered her missionary style.

While on top, I grabber her ass cheeks and started picking up the pace. She was so wet that her asshole was well lubricated as well and I started playing with her hole while we continued to fuck. Eventually she took my hand and indicated that she wanted me to finger her asshole. A few minutes later we switched positions and I started fucking her from behind while continuing to finger her ass. I asked if she had ever had anal sex and she said no but really liked how my fingers felt and was willing to give it a shot.

I got up quickly and grabbed some hand lotion from the bathroom, and lubed up my penis and her asshole even though she was absolutely soaked down there. I slowly, but easily entered her ass from behind and she absolutely loved it. For the next few minutes I fucked her in the ass in a few different positions until I couldn’t take it anymore and shot a huge load deep into her ass.

We both freshened up a bit, and cuddled/talked for a while and smoked a cigarette out the window. When we got back into bed, we were both horny and started fucking again. This continued for hours, we’d fuck, take a break, and went at it again. We woke up at least three times in the middle of the night to keep fucking.

She had a flight the next morning and I had work, so we had sex one more time, then I showered and rushed to work.

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? In the morning I was super hungover so I called out of work. She had a flight in the afternoon so we ordered breakfast, had more sex and chilled until she had to leave for the airport. Her car service came to pick her up, I left with her and the driver dropped me off at my apartment.

Despite being hungover, I felt great about the previous night and great about her. The sex was absolutely mind-blowing and she was really cool/smart. We exchanged numbers and kept in touch. I traveled a lot to her city for work and would always see her and stay with her.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication, 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

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? Everything. We had amazing sexual chemistry, continued to hook up, and became friends.

What was the WORST thing about this hookup? Being hungover the next day. Other than that, nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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!

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