Beginning Of A 3 Month Fling



What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

Beginning Of A 3 Month Fling

How long ago did this hookup happen? 10 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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? We’ll call her Jane for the purpose of this story. I was in Philly for work and went to a bar for a nightcap after dinner before planning to head back to my hotel. It was a Thursday evening and I was going to drive back to NYC the next day after several days on the road.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was sitting at the bar and she was there with a girlfriend and this random guy. I think it was the boyfriend of her friend. We all got to talking and I began flirting with her. She looked around 40ish, average face but with an incredible figure. 5’4”, amazing legs and ass and petite, with a medium size rack. I was in my early 30s and newly single after an ugly divorce a year before. The flirting gave way to us brushing our legs against each other and holding hands as we got closer and closer due to the noise in the bar. We went out to smoke a cigarette and it was snowing. We began to make out and we could see her friends pointing at us and giggling. She said to me “I’m not going to sleep with you tonight because we are both really drunk but why don’t you put my number in your phone and call me tomorrow when you get up. We’ll do brunch and then go back to my place and fuck…” I thought to myself, ok, let’s see if this really happens. I was somewhat doubtful but called her the next morning and she was good to her word for brunch. I had checked out of my hotel, packed up my car and drove to meet her at the brunch spot she picked. We had a great conversation about all sorts of stuff and connected in a way that really made me want to fuck her even more than the night before.

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 drove my car to her place and walked around for a bit. We went inside and hung out listening to music and walked her dog. She had some weed which we smoked and then started making out on her sofa. We eventually made it into her bedroom, stripped completely naked and I went to town eating her pussy. I used my index and middle finger to stimulate her g-spot as I focused on her clit. She was soaking wet by this time and we were both very aroused; I could tell she was close so I slipped my pinky into her ass and this pushed her over the edge. She exploded and I looked up at her. She gave me this look of bewilderment and lust and then we switched. She began sucking on my engorged cock and it didn’t take me long before I came. She didn’t swallow but jerked me off as I blew my load everywhere. We both fell asleep together naked and woke up in the late afternoon. We agreed to get dinner with no talk of me leaving her place. We ended up back at her place after a nice meal and had a talk about STIs and condoms. She said that she hated condoms and I did as well and I had been tested recently and was clean. We ended up screwing each other’s brains out for the rest of the evening and then into the weekend. The memorable part for me was her riding me bareback that evening screaming that she couldn’t stop cumming. We were having amazing, athletic sex and our bodies were totally compatible. I only regret not being able to cum inside her as she wasn’t on any type of contraceptive. I ended up leaving her place on Sunday afternoon and this was the start of a three-month fling.

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? I felt great about it. I’ve had multiple partners in my life and am married now but she is towards the top of the list as far as being compatible with me in bed.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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? My friends. They thought it was hilarious that I was hooking up with someone over 10 years older. Don’t think they had any idea how mind-blowing sex was with a woman who knew her way around the bedroom and was totally uninhibited.

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? Amazing sex.

What was the WORST thing about this hookup? After three months, I ended it because she wanted something more serious and I couldn’t commit to a relationship. I would hook up with other people and then see her on the side and I felt guilty doing that. After I broke it off we didn’t see each other again but I often wonder if we saw each other, what would happen.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was a very liberating experience and time in my life. Really got to know what truly great sex is with someone you connect with physically and mentally.

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? We started adding sex toys to our bedroom routine and I bought lingerie for her; stockings, bra/panty sets and a couple of garter belts for her to wear, which she loved. She would keep her heels and stockings/garter belt on when we fucked and we both were really turned on by this. We ended up doing a lot of coke together as well which didn’t really help sex, at least for me, but it added to the wildness of our relationship.

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 think it’s great. Now that I’m married and don’t sleep with other women. I have amazing memories and experiences that add to my sex life with my wife. I think that everyone should be with a number of people before settling down.

What do you think about the Casual Sex Project? It’s great! A wonderful platform for people to share their stories.

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