Double Trouble (Pleasure)–Two in the Chamber



What’s your gender? Man
How old are you? 44
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Kansas City
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Engineer
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Hetero that can handle M to M contact
How many sexual partners have you had in your life (including oral sex)? 8+
How many hookup stories have you here posted before? 0

Double Trouble (Pleasure)–Two in the Chamber

How long ago did this hookup happen? about a month

What was your relationship status at the time? Same as current status

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 are married friends. He six feet slim, blonde. Her, 5’9″, slim, natural blonde and sexy. I have known them for over a decade. We have an ongoing friendship/threesome relationship. For this particular fun session, we were at their house. I have known these two so long–he a great friend and fun “orgasms for her helper”, and she is a down to earth great gal, very sexy, and loves having both of us.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began in their living room. We were relaxing watching TV. We had sex earlier in the morning, and were having a fun, “no kids”, no clothes, casual sex day. Planning was to have our kids, their kids and my kid, at grandparents, so we could have adult time. She instigated this “round”.

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? The session started with her asking for us, the men, to masturbate. She performed oral on us, singly, and with both of our penis tips in contact and in her mouth. She held our shafts together and stroked us. We in-turn performed oral on her, and she got us on the floor in a position called the king of clubs where she could hold our cocks together and perform oral on us at the same time. She alternated her position so her pussy was in our faces alternately, so we could perform oral on her.

After oral fun, she rode us vaginally individually to open her pussy up. Then she lay on her husband facing him, riding him, and then asked me to put my cock into her pussy at the same time her husband’s was already inside her. Double pussy penetration is something we have done from time to time, and we all enjoy it tremendously. It is very tight, wet, and the sensations are phenomenal. I felt euphoric. It felt really good to feel her very stretched pussy around me, and her husband’s penis moving against mine.

We all were energetic and on cloud nine. We were all moaning, and she was letting us know how good her pussy felt with both of us inside her. She is an excellent lover, and she craves, desires, and enthusiastically uses our cocks for her pleasure. My friend is open to expanding her pleasure boundaries, and I, too, love to see her pleasured. We love to “become one” and feel each other inside her.

Initially, the double pussy ended with my friend pulling out of his wife to avoid orgasm. When he did, she moved forward to decouple me and her. She had me switch positions. I was on the floor now, and she rode me while her husband cooled down. Then she told him to put his cock back inside her pussy. I became the “anchor cock” and held still, to let him stroke or slide in and out of her.

She began asking him to cum/orgasm inside her. He continued to pump in and out of her till he could hold his orgasm no more. He orgasmed in her and she came as well. Once he pulled out, he lay beside us, and she sat upright and rode me. She bade him to stand up, and she performed oral on him to capture every drop of his ejaculate from his urethra.

We continually told each other how hot the others were, and how exciting it was to see and feel all the sexual action. She rode me till I had my orgasm inside her as well. She had received two loads of cum in her pussy.

After she slipped off of me she stood up, her husband embraced her, and they kissed deeply to taste each other. She had actually orgasmed multiple times with us in her. It always is very exciting for her to have both her men in her–she always says it when we are both in her.

She dropped back to the floor and laid on top of me, and we kissed deeply as well. Then we all laid next to each other and exhaled and basked in the moment. She got up a few minutes later, and it was exciting to see our cum leaking out of her vagina.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? After the hookup, we relaxed more and decided where we would go to dinner later. The next day was Sunday, and we were all sad to see the weekend end. We tentatively planned our next get together after some morning sex. My hope is to continue having a great friendship with my friends. We communicate often, and we are always excited to speak and get together.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Didn’t want to disappoint my partner

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? I talked with them about it. We are all very secretive about our threesome fun. They loved talking about it. On the phone or via text. It gets us all excited for the next time.

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? Experiencing the kinky fun that only a two on one scenario can provide. It was absolutely sexy and a turn on to see a woman so pleasured.

What was the WORST thing about this hookup? It ended. lol.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I used to have definite homosexual boundaries, but my threesome experiences with my married friends have caused me to drop the “no male contact” rule to amp up her/our pleasure.

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 think the longer you get to know people, the better the experiences get.

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? Casual sex is energizing–especially when your partners are safe and well known. Of course, new partners are very exciting, too.

What do you think about the Casual Sex Project? It is a neat way to communicate sexual experiences.

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