First Time with a Couple

by Clister

What’s your gender? Man
How old are you? 26
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Upstate NY
Highest education received: Some college (not currently in college)
What’s your occupation? Construction
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? None

First Time with a Couple

How long ago did this hookup happen? 4 years

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? They were married. Both mid to late 30’s. They both were in good shape and she was very sexy as I like the thought of an older woman wanting a younger guy. I responded to an ad on Craigslist wanting a MMF 3 some with a straight guy. My pictures in my response stood out to her so I got a reply rather quick.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began with some emailing back and forth. It was the female half I was talking to. Her husband let her pick someone out. She sent me some pics of herself wearing some lingerie and told me what she would like me to do to her and I returned pics which seemed to make her very excited. She told me she loves dp and has done it once before. She also told me she wanted me and her husband to cum on her face. I LOVED hearing that she wanted us to do that. She couldn’t wait to meet. She didn’t think I was real and thought I must have photoshopped my pics. Some boundaries were discussed prior to setting up a meeting. No kissing and no cumming in her mouth. They were comfortable enough with me that they told me to just come to their house. I was really nervous it was my first time doing anything like this.

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? When I arrived, I found myself in a very nice home with a very attractive and friendly couple. I sat down in the living room and offered to smoke some herb with them and they asked me a few questions about the courses I was taking in college. Her husband was very laid back and just wanted his wife to get off. They had a powerful chemistry. We discussed protection while she snuck away for a minute and came back in lingerie with her tits hanging out. She pulled us into the bedroom. She lay on her stomach on the bed and watched us get naked. Being so nervous I wasn’t able to get hard so she said “let me help you”, grabbed my soft cock and swallowed it. She had no gag reflex and it felt amazing. She had her finger pressed on my asshole. It was extremely sexy and the first time I’ve felt that. Her husband was jerking off getting hard watching her and asked her “do you like your boy toy?”. She nodded yes with a mouth full of my cock. I put a condom on and took charge. Got on her and started pumping the best I knew how. She was on her back and he was on the bed now on his knees and she was playing with his balls watching my dick plunge into her swollen pussy. She looked up at him and said, “oh he’s good!” He then asked us if we wanted to DP now so we did I was on the bottom with her huge mature tits in my face and he was behind. She then came really hard with both of us wedged in 1 hole. I then got behind her doggy style and gave it my all while she sucked off her husband. After a few minutes, he told me don’t cum yet. We all got off the bed and she kneeled in front of us and said “cum on my face both of you”. We did and she loved it. I didn’t cum for 5 or 6 days before this in hopes of having a giant load for her and it worked. Her face was covered. She asked both of us if we thought we could cum again so we tried and I was able to. He went soft after I came. She hopped in the shower and told us both to eat more fruit lol.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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 went our separate ways. shortly after that I got into a relationship and blocked their number so I wouldn’t be caught off Gaurd. If I were single I would love to see them again

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, Learning new things, experimenting

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

What substances did you consume? 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? 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? Haven’t told anyone ever

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? That she wanted both of our cum all over her face and tits

What was the WORST thing about this hookup? There was another guy that was supposed to come over and he bailed

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve realized that swinging/group sex is more common than I thought

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

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? I think it’s great and I enjoy reading them

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