What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Senior Manager
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 26
How many hookup stories have you here posted before? 1

Two Women in One Day

How long ago did this hookup happen? Last summer

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? For less than a month

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 “Jane” at a speed dating event. She’s a high school English teacher. It seems more teachers come out to speed dating events in the summer. I’ve met quite a few of teachers. She was average build, long dark hair, and very friendly and articulate. I liked that. Our first date went really well. I discovered she had a bit of a wild side. She got drunk on our first date. The bartender at the bar actually cut her off. She also has some insecurities, as that episode caused her to light up a cigarette. She said she was trying to quit, but things like that bother her. After we were cut off at the bar, we walked back to her place to chill out. That led to a lot of making out and finger-in-vagina sex. We didn’t go all the way that night. I slept over, and then we actually did fuck when we woke up that morning. Over breakfast, we talked more and it came out that she wasn’t interested in having children. I found out she was 40 years old, though she looked more like late 30s. I wanted to start a family and was dating to find something long term to that end, but Jane was fun to be with, so we made plans for date number 2, which also went great and we also had sex. Date 3 was a week later.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I just had a date with “Elizabeth” on a Saturday (see other story). She slept over and we had a lot of great sex over Saturday night and Sunday morning. I had not expected things to turn out as it did. When she left, I was already feeling satisfied sexually, but that just made me hornier. So I was looking forward to my third date with Jane that afternoon. The plan was to go to an art gallery. I picked her up, we did the gallery thing, and then I took her out for dinner. We were enjoying the day and having a good time, and she was drinking a lot again that evening. We were feeling pretty good, with lots of touching and hand holding and flirting. I walked her home, and at the door to her condo, I kissed her passionately and told her that I wanted her.

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? She led me into her condo and started making out right away. I saw that she was already very wet from all the flirting and sexual innuendo buildup all day. I started licking her pussy and fingering her until she asked me to fuck her. I knew from our earlier sessions that doggy style was her favorite position, so I pulled her up and set her on all fours, and playfully slipped my cock quickly in and out of her. Despite not wanting children, she didn’t mention anything about putting on a condom this time. So I just started fucking her like that doggy style. I also knew from our earlier sessions that she liked it rough. I gripped her waist strongly to pound into her, then I pulled her hair back as I continued to fuck her, giving her the occasional butt slapping. She loved all of it and was being quite vocal. Having already had several orgasms with Elizabeth over the last 24 hours, I was going pretty strong and sustained in fucking Jane now. After doggy style, she rode me cowgirl style. We alternated between these two positions a couple times. I finished in missionary style and pounded a satisfying ejaculation into her vagina. She was very satisfied and so was I. Even though I had to go to work the next morning, I slept over.

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 had to leave early for work the next morning, so we didn’t have time to talk much about our “relationship” the next day. We kissed, and I went home to get changed before going to work. We agreed to meet up again later in the week.

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)

How intoxicated were you? A little tipsy/high

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? I didn’t talk to anyone exactly. I did mention to a friend that I’m fucking someone who I am dating casually but gave no further details beyond that.

How would you best summarize people’s reactions about this hookup? Neutral

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? She was a great fuck. She really gets into it. She provides feedback vocally when she is enjoying what I do. She tells me what to do to make her enjoy the sex more. Also, it was great to fuck two different women in one day. It made me feel very confident about myself and very sexually satisfied.

What was the WORST thing about this hookup? That she is expecting a long-term relationship, while I was not thinking the same thing because we had different life goals. I felt a bit bad about myself to use her for sex, but I was really horny and she turns me on. At the moment when I was fucking her without a condom, I was thinking that if she gets pregnant, I would more than be willing to commit to her. She did say that she got pregnant from an ex-boyfriend, but had an abortion when he was not willing to marry her. If it happened with us, I would have married her.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Fucking two different women in one day was really exciting, and it really turned me on. I had some guilt about doing this, less so with Elizabeth, because she just wanted a good fuck after her divorce. I felt guilty about leading Jane on, but I rationalized it by saying that I would have committed to her, and I would have if she got pregnant. This experience made me more comfortable with having more casual sex with different partners. I enjoy the communication at that level with different people.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? She broke up with me a week after that hookup after we had a fight about our relationship expectations.

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