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)? 25
How many hookup stories have you here posted before? This is the first

Ice Cream Sex

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 “Elizabeth” at a speed dating event. She was intelligent, which I liked. She was a teacher. I found out on our first date that she was somewhere between 38 and 40, and she had two boys. I want to start a family, so that was a bit older than I would have liked. However, since finding a steady relationship was hard, I was open to continue dating her and developing something, because that always leads to the possibility of sex.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We planned to go kayaking on our second date. It was a Saturday morning, when the kids were with their dad for the weekend. She lives about 90 minutes from me. We agreed to have her drop her car off at my condo, and then I would drive us to the kayak rental. When she dropped off her car, I was pleasantly surprised to see her wearing a short T shirt and high length cut off jean shorts. She looked very fit and sexy. We hugged and kissed and then I drove us to the kayak rental facility. At the lockers, she pealed off her jean shorts and T shirt to reveal that she was wearing a bikini. She was certainly not afraid to show off her super fit body! I helped her put on some sun tan lotion, which heightened the sexual chemistry. We spent the afternoon on a very pleasant kayaking trip. When we landed, we got changed and decided to have dinner together since we were hungry. She suggested a good sushi restaurant nearby. I could tell she studied the location ahead of time. The dinner was great: excellent conversation, nothing sexual, just good connection, and she was actually drinking a bit too much, so she was getting light headed. When I drove her back to my place, I suggested that she take some time to sober up before the drive home, and that we can spend the time in my condo making home made ice cream. She was very open to that idea, and excited that we were doing so many new and fun things on a second date. I had the ingredients to make strawberry ice cream. Cooking is a hobby of mine, and I have made ice cream many times, so the whole thing went quite well as we were touching and flirting in the kitchen. When the strawberry custard was finished, it has to cool in the refrigerator for 8 hours before we put it in the ice cream machine. When I explained this to her, she looked disappointed, saying that 8 hours would be a long time. I then kissed her and said we can spend that time making out. She pulled me tighter and we started kissing much more sensually.

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? I find every new woman a challenge in how to excite her. I led her to the sofa and enjoyed our time making out. After all, we had 8 hours! After she felt hot and excited, I stripped off her jean shorts and T shirt, revealing her bikini. I stripped my own clothes off and then took more time worshiping her fantastically hot body. Since she was covered in sun tan lotion on top, I focused my tongue on her sexy legs. I worked my way up and down her thighs and poked it under the crotch of her bikini thong. Eventually, we both wanted to have sex. We headed to my bedroom, where I put on a condom. By that point, she didn’t want any more foreplay. She laid on the bed, spread her legs open and pulled them up. I thrust my cock into her aggressively, grabbed both of her ankles with each of my hands, and started pounding hard into her. She was moaning enthusiastically. When I saw the wetness around her pussy, I pulled out to lick it all up and thrusting my tongue into her hole and flicking it around her clitoris. She begged me to start fucking her again, so I flipped her onto all fours and we fucked doggy style until I came. When I pulled out, we embraced. She said she needed that. I loved it. I said we are just getting started. We took a shower together, and then went back to bed. The second time was a slow affectionate love making session. This was followed by a third, passionate and intense fuck before we fell asleep together. The next morning, when we woke up, we made the strawberry ice cream. We were licking the ice cream off each other’s fingers. I put the ice cream on her tits and ate it off her. Then I made her pancakes with the strawberry ice cream for brunch. We had one more quick intense fuck doggy style before she had to leave to pick up her boys from their dad, this last time, without a condom since I had run out, so I pulled out and shot on her sexy ass. Rather than clean it up, she wiped my cum all around her ass, then put on her bikini and jean shorts. It was really hot!

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? We continued to date through the summer. It was too bad that she already had kids and too old to start a family with me. She is the type of woman I could really go for. Unfortunately, scheduling and distance meant that we could not keep up our dating, but it was a good summer fling and we had sex quite a few more times before our fling ended.

I fucked a second woman later that day, which I will share in a later story.

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)

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

What substances did you consume? Alcohol

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

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? One of my friends who went to the speed date with me. He was positive.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I have always wanted to pull off that ice cream seduction thing, because of the 8 hours of time you had to wait while cooling the ice cream. I couldn’t believe it happened perfectly, and it really did accentuate the sex, making it feel spontaneous and hot.

What was the WORST thing about this hookup? Nothing at all.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Getting it on in a fling with a sexy older lady is just fine. I used to avoid wasting my time with older ladies and single moms since I want to start my own family, but while I am still seeking that, having flings can lead to great sex for both.

All things considered, how POSITIVE was this experience? Very 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? I have not had a lot of casual sex while I was younger. Now that I am more confident about myself, and I am at that age where women are also less inhibited, casual sex is turning out to be an awesome and fulfilling experience. The more I get it, the more I want it.

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