Hotwife MILF

This post is sponsored by Trust Massage Oil.

by Swinging Single

What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Midsized city
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? IT
What’s your current relationship status? Single
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? Becoming addicted to sex
How many sexual partners have you had in your life (including oral sex)? about 50
How many hookup stories have you here posted before? 0

Hotwife MILF

How long ago did this hookup happen? Two years ago

What was your relationship status at the time? Single

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 connected with “Lisa” on a swinger’s site. There were no photos, but a great write up about how she is a business professional, a competitive athlete, an exhibitionist, and loves to wear sexy lingerie, while her husband is a voyeur. I connected with her with my a response that she said excited her the most. She called me one night and we spoke on the phone for over an hour. We agreed to meet up that weekend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was a 90 minute drive to the town where she and her husband lived. I waited for her outside a small diner. She showed up in a car and asked if it was me. I said yes. She told me to follow her. She also had to made a detour to buy some alchohol on the way back home. As I went into the store with her, I checked her out. 5’8″ shoulder length blond hair, athletic build, not as toned as I expected, wearing jeans, running shoes, and a simple T shirt and windbreaker. Average looking, but I thought fuckable.

We went back to their home where I met her husband. They said they were new to the swinger’s website and was having a hard time finding men. Her husband’s fantasy was to watch her being fucked by a several men, one after another, amd video taping it. They said most guys either weren’t what they were seeking, or they chickened out. Lisa “beefed up her profile” to attract more men. She didn’t compete athletically since she was in high school and she worked as as apartment manager. They are both divorved and this weekend was one where both their exes had the kids. I was supportive of them and told them I thought Lisa was very hot.

We talked a bit then she went into the bedroom. While she was in the bedroom, her husband told me I am good and that she is interested in me. She came out from the bedroom and I saw she had changed into a blouse that revealed a lot of cleavage and a mini skirt tha showed off her long athletic legs. I was getting into the mood. She sat next to me while we watched television and had drinks together, chilling out. Her leg was rubbing against mine. We came to the conclusion that this was something we should do and we can plan a session the next time we are all available. We were all nervous and not sure how to proceed. That’s when I said why don’t we give it a try now? They looked at each other and then said sure. Her husband added that everyone is just horny.

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? Lisa and I finished our drinks and started kissing. He husband sat back and watched us. It took a while to get undressed, as I was self-conscious about everything. But we were talking among all three of us, which helped encourage all of us. The talk started getting sexual too. There was fingering, caressing, and plenty of foreplay. At some point I suggested her husband can videotape us if he wants. He asked if I am sure. I said definitely. While he was getting the camcorder, Lisa and I were getting into heat. I started licking her pussy and fingering her at the same time. By the time her husband got back, Lisa was moaning and clearly in ecstasy. He said he was really turned on and was sorry he missed the earlier hot and heavy action. Just as he got the camcorder going, I penetrated his wife doggy style and started fucking her. To my surprise, it was incredibly exciting being filmed by her husband while she was moaning away. I banged her for a while, then we moved to the sofa. Lisa laid on her back and spread her legs open and wide up into the air as I penetrated her again and started fucking her again. She said she was loving it. It didn’t take long for me to orgasm. By then, her husband had set the camcorder on a tripod and was jerking himself off. I said hey, your wife is still in heat and needs more fucking. With my encouragement, he started fucking her while I picked up the camcorder and continued the filming. He pounded into her with her legs spread wide and then he came. I was so turned on that my erection came back. He didn’t wear a condom and his semen and her juices were running out of her pussy. I put on another condom and proceeded to fuck her a second time in the same position that her husband had just finished. At that point, he said it would be really hot if I could take off my condom and thrust into her a few times. At this point, I was so high on the sex that I did just that. I pulled off the condom and thrust into her, giving ample room for her husband to take some close-up shots. After a bit of that, we switched position so Lisa could ride me cowgirl style. She really rode me hard. I screamed out that I am coming. To my surprise, she didn’t pull out. She just rode me harder as I ejaculated into her. She pulled out and raised her ass into the air to allow her husband to videotape a closeup of my cum oozing out of her pussy.

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 cleaned up, spent some time talking about how exciting it was and how it turned out. We watched the video on the camcorder. It turned us on so much that we wanted to fuck again, but we were all spent. I agreed to help Lisa and her husband to filfil their fantasy. I said I didn’t mind being one of several guys gang banging her.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? We did talk with other men who we lined up to fuck Lisa. I told them about my experience to put them at ease. Some were ambivalent. A few were enthusiastic.

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? First time with a swinging couple.

What was the WORST thing about this hookup? I penetrated her again after her husband had ejaculated into her. That freaked me out. I was hesitant, but the heat of the moment made me do it. I was surprised that I was turned on by the sleaziness of the whole thing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I was really nervous getting into this scenario. But they were such nice people and easy going and they said the same of me, which put all of us at ease. As the night progressed, it just felt better and easier.

I thought I would be unable to perform with another man watching, but to my surprise, it was a turn on. I realized that I was comfortable being able to perform in front of others. That really improved my sexual confidence. I was also surpised that I was able to have sex with another man’s wife while he watched.

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 did progress to more hookups which I will share in a few more posts.

What do you think about the Casual Sex Project? Love this chance to share a story that has been very private to this point.

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