by DJ

Gender: Male
Age: 30
Race/ethnicity: Caucasian
Current location: Connecticut USA
Highest education received: Some college (not currently in college)
Relationship status: Engaged
Religious affiliation: None
Any other term(s) that describe your sexual orientation/sexuality better/best? Bisexual recovering sex addict
How many sexual partners have you had in your life (including oral sex)? 45+
How many hookup stories have you here posted before? 6

Failed Threesome Yields a Fountain Pleasure

How long ago did this hookup happen? 2 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends With Benefits Threesome

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? Nikki was a girl I had been seeing on the side while in a committed relationship. We had an intense sexual chemistry and attraction to each other. We weren’t dating but we did have a strong connection both emotionally and physically. Neither of us had ever been with anyone that fulfilled us sexually as well as each other. She was chubby but confident. Had an amazingly tight, smooth pussy, beautiful hair and eyes. She had another fuck buddy that she had been seeing at the same time and I harbored some slight jealousy towards him even though she insisted I had no need to be jealous. My macho pride needed to put this jealousy to bed once and for all so I told her I wanted to do a threesome with him. She thought it would be fun so she invited him to come over one night for drinks and a threesome. You know, as you do.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I covered this in the last part. He showed up and we started talking. Just getting acquainted/ sizing each other up. He’s not an idiot. I think he knew what my motives were. Eventually we decided to get started. However, as soon as he saw that my cock was about five inches longer than his, he seemed very intimidated and timid. He couldn’t get it up. So I left the room and let them get started on their own. This didn’t work either. He couldn’t perform and had to leave. At that point, Nikki and I decided to keep the party going.

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? Nikki was already very wet after having two different guys kissing her and going down on her. I was extremely hard after having my ego boosted in the psychological chest thumping match I’d just won. We kissed and made out for a while, a furiously passionate kiss that few people ever even experience in their lives. Once I knew she needed to cum, I went down on her and licked her pussy until she had a huge, orgasm, which left her shaking. Then, feeling like she was close to exploding, I pulled her to the edge of the bed and started sliding my dick in and out of her pussy, rubbing along her gspot with each thrust. She started to express that something weird was happening. She looked at me with a look that said “holy shit baby I’m gonna cum all over”. After several hard thrusts that crossed her over the threshold, I felt something pushing my dick out of her pussy and then suddenly it happened. She was squirting all over me. This was the first time she had ever squirt and the first time I had ever made a woman squirt. It was amazing and she was left shaking and trembling in a puddle of her own pleasure. I continued to fuck her in that position over and over until I came deep inside her. She ended up squirting several more times after the first. That night we had sex many more times and each time she came about five times.

Did you have an orgasm? Did your partner(s)? I had a few. She had too many to count.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. We trusted each other and she was on the ring.

What were your REASONS for having this hookup? I wanted to prove that I was a better lover. It was a very selfish reason for the night but it was fun.

Were alcohol or drugs involved? If so, how much? Some alcohol.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Nikki and I now live together and have a daughter together. We are engaged to be married, though I still struggle with my sex addiction. I love her very much and nobody else in the world knows me as well as she does. This night is definitely one of the highlights of our sexual history together, from long before we ever thought we’d actually be together.

To whom did you talk about the hookup? How did they react? My girl friend that I share all my escapades with.

Was this a consensual and/or wanted experience for you? For your partner? Yes yes and yes

Do you regret this hookup? If so, why? Not at all

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The squirting was the best part. The worst was the other guy not being able to perform.

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

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

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