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What’s your gender? Woman
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States West Coast
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Accountant
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? Committed Relationships or Friends before having Sex
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 3

A Best Friend’s Husband

How long ago did this hookup happen? 1 year ago

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

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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? He is 24 years older than me, being 52, and I am 28. He is the husband of one of my close friends, my boss. I have never hooked up with him and I met him for the first time just over a year ago when I stayed overnight at their house before leaving on a trip as their home is close to the airport. I always thought that Jeff was good looking, very friendly and had a great sense of humor. I admit I was sexually attracted to him and wondered if a middle age man would be better in bed than younger men due to experience. He was married though so I never thought about it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My boss was busy on business and was going to be working until 10:00 pm and needed some paperwork dropped off to her husband at the house. She gave me paperwork in an envelope and I drove 35 minutes to her house. I also had the rest of the day off so I figured it was no big deal. I arrived at the house and Jeff answered the door. He invited me in and I entered, giving him the envelope. The kitchen smelled amazing and I asked him what he was cooking. Jeff told me and asked if I wanted to join him, and so I figured, why not. We ate and talked during the meal. He listened and asked questions and I found him easy to talk with. We finished the meal and I figured since I had eaten I should help clean up. I offered, and Jeff accepted my help. I wanted to stay and hang out with this man. That tingling was now a warm glow in my vagina, and I felt myself get somewhat moist. I wondered if Jeff was as gentle, kind and warm in bed as he was in person. It was almost as if Jeff read my mind because he walked to me and looking at me said “I may be off base but…” and with that, he kissed me. First a peck and then we both tore into each other. His tongue entered my mouth, exploring it, wrapping around my tongue and I did the same to him. That warmth and glow went burning hot and super wet in an instance. I felt my boobs enlarge and my nipples go erect. I could feel his penis swelling against my leg as we embraced.

For the next ten minutes, we kissed and made out, turning each other on. Jeff took me by the right hand now and led me down the hall to the master bedroom. It hit me, I was about to sleep with my boss’ husband. Jeff sensed this and asked, “Are you sure?” I wasn’t and I almost backed out but man, I was horny now and after not having it for 4 plus years, I wanted it, and I wanted Jeff. “Yes, I want you,” was my simple reply. There was no planning here, just raw desire taking over two consenting adults.

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? Jeff then lifted off my tee shirt and removed my sports bra; my 34D breasts were enlarged and my nipples hard. He then removed the rest of my clothes, leaving me naked. I removed his clothes and there we were, naked. We began to make out and his left hand caressed my right breast and played with my nipple. It felt great to have a man play with my breasts. Soon he was kissing my ear, which REALLY turned me on. Then he was kissing my neck, which heightened my desire, and then his mouth was around my right nipple as he gently sucked my breast. I held his head with both of my hands against my breast and he alternated between my right and left nipples. By now he was on my knees in front of me and he slowly moved off my breasts, kissing my stomach, my navel, moving to my inner thigh. I knew where he was going and the amount of wetness I had increased. Next, I felt his tongue on my pussy lips, gently as he licked up the right side, over and down the left. Oh, I was so turned on! He stiffened his tongue and it entered my vagina. He unstiffened it and then did a licking motion of come here with his tongue. This hit my g-spot and sent waves of pleasure through my body. I moaned “Oh, oh, don’t stop,” as he kept making love to me with his tongue. Soon I was in ecstasy and suddenly I felt a feeling I had never felt before. Orgasmic wave after wave swept over me as I screamed and collapsed.

Jeff now worked on my clit for a while, giving me another orgasm that way and then he laid me on the bed and spread my legs. He entered me in missionary position and at first, he kept his weight on his hands, but I drew this man down. I wanted to feel his warmth and body against mine. As his dick entered me, I felt his girth and length and he slowly began to thrust back and forth. His penis rubbed my g-spot perfectly and he was leading me back down the path to another orgasm and he knew it. I felt that wonderful flush of pleasure again and squeezed him harder. I felt his penis swell inside of me, and I suspected that he was close to ejaculating. He suddenly moaned, and I felt a warm stream shoot out of his penis, then another and another. Jeff was cumming deep inside of me and I squeezed him with my legs and my vagina, wanting every precious drop. He kissed me now as I kept his penis in me, squeezing it, thrusting it deep inside of me. He lost some of his hardness but kept it firm. I looked at him and honestly said: “I have never had it that good.” Jeff smiled and said “We’re not done either,” and his smile and mine got bigger.

He laid next to me, fingering my vagina and turning me on as I played with his balls and dick making it grow hard again. I wanted to know so asked Jeff “Why?” “Why not” was his reply. “I have always been attracted to you and my wife can’t anymore due to a health reason.” “So was this a setup?” I asked feeling a little mad. “NO. I didn’t even know you were coming by until right before you showed up.” Jeff said. “I just took advantage of the situation.” “Oh,” I said, feeling bad. “And if you get me pregnant?” I asked. “Look, I am worth millions of dollars and we work because we enjoy doing that. If I get you pregnant I am not worried about taking care financially of a child or you. You didn’t have to worry about it.” I reached over and kissed him with all the passion I could muster.

He laid on his back and he had me mount him. He guided me on how to naturally use my body to guide his penis into my vagina. It took six or seven tries, and we laughed and enjoyed the humor of the moment, and then I successfully did it. He was hard for sure, back to his full size and it felt damn good to have his dick inside of me. Being on top was different as I was in control. I got to thrust at my pace and I loved that control. I went fast, then slow, then took his entire penis shaft into my vagina down to its base, and then pulled it out slowly and then fast the next time. It was a major turn on. Finally, I felt my orgasms starting to come, so I increased the pace and tempo of our lovemaking. He matched me now, thrusting up as I thrust his dick into my waiting vagina. Faster we went and suddenly I fell onto his chest as I began to orgasm. I felt his penis harden, thicken and swell as his ejaculate filled his shaft. That sent me off even more and I screamed in uncontrollable pleasure. I felt his hot stream streak inside of my vagina again and again, and I screamed at him to “shoot it all in me.”

He asked me if after one afternoon if I was ready to commit to being lovers. I told him hell yes, as long as he can keep making love like today. He smiled and I told him that I was falling in love with him, and wanted to just keep making love. With that, it had been a good forty-five minutes so I began to play with his penis again. It’s easy to make this sex-starved man hard and horny and he simply turned me on by kissing me and touching me. I loved as he started to suck my boobs and nipples and finger my vagina. That turned me on and this time we made love in the missionary position again. I love how we work together in the missionary to have our orgasms at the same time and it gives him control. There are times I like Jeff having control, but then we did it with me on top again and I like the control and the orgasms it brings. So not that I prefer one over the other, it depends on which one I want and what part of my vagina stimulated.

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? Jeff and I have been lovers now for over a year. We make love two to three times a week and I have gone off the pill. If I get pregnant, no biggie. His wife knows we are lovers and accepts it and actually approves. She watched us once now, and then one time joined us and gave Jeff oral sex and me oral sex, making us have orgasms. Very open relationship but Jeff is the man I want to be with right now.

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

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

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? Eventually to his wife, my boss. To my mother. She knew when she sent me there that there was a good chance we would have sex and she picked me for that. Kinda of cool, she knew we were a match. My mother doesn’t care about the sex but doesn’t want me to get pregnant or have a long-term relationship with him. She wants me to marry someone my age and be content. I am content with life how it is.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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 found a man who is attracted to me, thinks I am wonderful, that allows us to have incredible sex together and spend time together.

What was the WORST thing about this hookup? None.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope

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? Nope.

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? My sexual and relationship is not traditional and I am fine with that.

What do you think about the Casual Sex Project? Good open up views.

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