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What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Toronto
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Tech
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I think about sex often. I enjoy having sex with partners who are expressive about their wants and desires.
How many sexual partners have you had in your life (including oral sex)? about 75
How many hookup stories have you here posted before? one (Hotwife Milf)

MILF Curious About Swinging

How long ago did this hookup happen? A year and a half ago

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Group sex

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 my swinging partner, “Teri” on a swingers site. She was a 38 year old high school English teacher, and single mom who had been divorced for over a year. She was looking for a partner to try swinging with. She was 165 cm (5 foot 5 inches), and was an avid runner. She was slim, extremely fit, and toned. She told me she picked me because I was experienced at swinging, and she liked my thoughtful and intellectual approach. I’m sure that me, being 7 years younger than her was also a reason! We met over a dinner date and started a sexual relationship on our second date. We got along very well and the sexual chemistry was excellent. The sex was very physically intense and passionate. After our third sexual encounter, we started looking online for another couple.

We were both turned on looking over the profiles together. We connected with married couple “Brian” and “Lana.” Brian was 45 years old, 183 cm (6 foot) and had an outdoorsy athletic body. Lana was 42 years old, 175 cm (5 foot 9 inches) and loves to work out. She just won a local fitness competition. They were also new to swinging. We spoke with them over the phone. They said they liked our profile because of our common interest in health and fitness and in working out. It was particularly exciting that this would be the first time for Teri, Brian, and Lana.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Brian and Lana said they also enjoy dressing up for dinner. We agreed to meet at a hotel with an upscale restaurant. We were all turned on as soon as we saw each other live. Brian and I both wore suits. Teri wore a jacket, miniskirt, and heels. Lana was dynamite in a high cut dress and stiletto heels that showed off her long legs.

We enjoyed the wine and dinner and we talked about fitness and working out. That turned into talk about sex and what we liked to do, and that’s when we expressed that we wanted to have sex with each other. We quickly ended the meal. The waiter asked “no dessert?” Lana smiled at the waiter and said we had other plans.

I booked a room in that hotel with an app on my phone. Brian’s wife, Lana, came with me to check in as a couple. We went up to the room first to brush our teeth and wash up a bit. Brian and Teri came up after we texted them the room number. We left the door unlocked.

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? By the time Brian and Teri came into the room, Lana and I were kissing on the bed. Brian and Teri joined us on the king-sized bed after they cleaned up. I kissed and licked Lana’s legs and arms and neck and got her aroused before taking off her clothes and stilettos. I stroked Lana’s pussy and fingered her then let her suck my wet finger and then I kissed her. Teri was breathing heavily from Brian’s foreplay as well.

Lana laid on her back to let me penetrate her standing at the edge of the bed. At the same time, Teri was on her hands and knees, allowing Brian to penetrate her doggy style standing at the edge of the bed. We were looking at each other as we fucked alongside each other.

From there, we changed positions a few times: doggy, missionary, cowgirl, reverse cowgirl… Brian and I both came after we pounded into our partners vigorously and powerfully.

From there, we swapped back to our own partners. Lana sucked Brian’s cock while Teri sucked my cock. When we were hard again, we spent the second round fucking our own partners.

We took a break to hydrate and recover. We finished the night with me going back to fucking Lana, and Brian fucking Teri.

The sex was passionate, intense, and powerful. We were all very comfortable with each other. Both Lana and Teri said it was the best introduction to swinging that they could have hoped for. Brian and I agreed.

Brian and Lana left to go home. Teri and I spent the night in the hotel room, where we had more sex.

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? Teri was very excited to fulfill her desire to swing. We were interested in getting back again with Brian and Lana, but Teri and I were also excited to experience more new partners.

That leads to an even more exciting experience which I will share next, as “Sex-fueled bareboating”

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), Learning new things, experimenting, Thought it was an important experience to have, Making new friends

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? Teri, Brian, and Lana all spoke about our feelings afterward. They were positive. We also shared this experience with future swinging partners, without naming names. It was also received well.

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? I introduced my sex partner, Teri, to swinging and was able to fulfill her desire to become a swinger.

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? Being respectful and open leads to better sex. Admitting inexperience to each other is actually a great way to get the experience one wants.

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? I used to seek single partners for sex, but that often ended with women to whom I had little attraction, or with whom I was not interested in a long term relationship. Admitting upfront that I want to swing, and finding a like-minded partner has led to immensely better sex. It is a lot easier to get a lot of regular sex this way.

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 grew up in a sexually conservative environment. I wanted to meet the right person to date, have sex, and marry, but that led nowhere. I did not lose my virginity until my mid-twenties. The lack of dating and sex was probably traumatic to me, and that’s why I think about sex so much now. I would like to fulfill my needs in a way where my partners are fulfilled and satisfied as well.

What do you think about the Casual Sex Project? I love it. It’s made me feel better about myself.

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