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What’s your gender? Man
How old are you? 51
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
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Educational Product Development/Sales related to Technology
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Lovin, Touchin, Squeezin
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 1

Hot And Steamy In San Antonio

How long ago did this hookup happen? Yesterday

What was your relationship status at the time? Engaged/Married (monogamous)

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

How long did you know the person before this hookup? For more than 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? Nancsi 8 years older than me, just turned 60, and we have worked together for 5 years. She is blonde, shorter, about 5’4″ and has small, compact boobs, and is in decent shape for her age. Blue eyes and a laugh to die for. Married for over 35 years, she is bored of her husband. I met her when I began my new job over 5 years ago and we promote and sell together, traveling a lot together. Our relationship is one of deep friendship from the time we spend together, we go on walks in the evening, work out together, sometimes eat dinner together, and often watch a movie together in the theater or a motel room.

I have had feelings for Nancsi for about 2 years and have wondered what it would be like to screw her. I have always believed Nancsi has the same feelings because of comments that she is struggling on whether she could have two men in her life, that she hopes I don’t ever think or fantasize about her cause that would be a turn on. Of late she has brought me closer to her in a physical sense, breaking her space bubble and showing I am in. I haven’t acted on it though.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We are in San Antonio for a major Educational Technology Summit and on Tuesday morning, we set up at the conference center making sure all of our materials and stuff were there. Nancsi at around 9:30 am, after we confirmed everything had arrived, said she had forgotten her laptop at her hotel room and asked if I would go back with her to get it to cover how we were going to set things up. “Sure” as that was common for us to do.

We got back to the hotel and Nancsi asked for me to come up with her so I did. We entered her room and it was a suite with the bedroom area off to the side. I sat down as she went to get her laptop. .A few moments later Nancsi walked out and I felt her hand on my shoulder. I looked up to her naked upper body in view. Her boobs were indeed smaller but firm and round and her nipples were hard. I went to stand up and she pushed me down as she came in front of me. “I’ve wanted this a LONG time,” Nancsi said. She was naked, with no pubic hair on her body. She sat on my lap and kissed me several times and smiling asked, “Do you want me too?”

By now, every fantasy I had ever had with Nancsi was coming true. My penis had gone hard, and emotions flew over me like I had never thought of. I had never cheated on my wife, and our marriage was solid but sexless after 28 years. “Hell yes” I replied making my mind up quickly. Nancsi unbuttoned my dress shirt, removed it and my tee shirt and rubbed my chest. We made out now, as she fumbled with my belt buckle, then undid my dress pants, slowly undoing my zipper. I stood and she removed my pants and boxers, and I removed my socks. Naked, we embraced and I felt my hard penis rub between her legs.

We now walked to the bedroom where on the side of the bed, Nancie kissed me and asked “Sure?” “Yes, no questions. I want you, and have for a long time.” “I know” came her reply. “Are you sure?” I asked. “Yes.” came her reply. “What about two men in your life?” “Well, I can be married to one and I can be the lover to other is what I’ve decided. You okay with that?” I replied by nodding as we kissed and got into the bed.

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? I have to admit, it had been a long, a VERY long time with no sexual intercourse and I was worried about that. However, much like riding a bike, it came back easily. That and Nancie was not a silent communicator. She is a very vocal woman and in bed, she shared what she liked, and what she had never had done. We continued to make out and using my finger, I began to rub her vagina area, inserting my finger and curving my finger upward and back as I was in her moist and soaked vagina. Nancsi now stroked my penis, playing with my head and she licked her fingers with her tongue, wetting her fingers with her saliva and driving me crazy. Her fingers would go down also from time to time, and using her fingertips, rub my testicles. Damn, that felt good.

I slowly got Nancsi to begin to breathe heavy, with little sighs and gasps of pleasure as I now used two fingers inside of her vagina. At one point she put some lube into her vagina and then into her hand and as I played with her vagina, I increased her wetness until she was not just soaked from her own wetness, but saturated in lube and cum throughout her vagina. Her hand now really stroked me, focusing on the top of my head.

I knew it was time as she moaned aloud loudly and moving to be face to face, side by side, I lifted her leg over my body and gently inserted the head of my penis inside of her vagina. Nancsi moaned as I entered her, leaning and kissing me deeply. I pulled out and went back in several times until on the fourth time, I slowly drove my harden penis completely inside of my Nancsi. “Uhm, yeah” she replied. We then began to move slowly together, in rhythm and in sync, me pushing my penis in her, she pulling it in and then as I withdrew about half way she would squeeze.

We kept this love making up for over 20 minutes, speeding up, slowing down so I wouldn’t cum. Slowly I could tell Nancsi was really turned on and she moved to get on top of me, my hard penis coming out. Instantly her hand guided my penis back inside of her vagina and Nancsi started to take full control and pound it in and out quicker and quicker. “Oh yes, Oh YES” she moaned and then “I want you, I want you, NOW, CUM NOW!” Suddenly she screamed and I felt her vagina tremble as orgasm after orgasm was unleashed. I felt my penis now fully and completely hard and full of my cum ejaculate my wad and cum inside of Nancsi. “MORE! OH OH OH!” she screamed as I shot my cum again and again inside of her.

Nancsi collapsed unto my chest, using her vagina to squeeze every drop of my cum into her vagina. We kissed and I said, “I am so in love with you.” Nancsi smiled and said, “Yeah, I love you too.”

We laid side by side for the next thirty minutes kissing, talking and just totally enjoying the afterglow of our love making. Nancsi now began to play with my penis again and then to kiss me. She worked down from my lips to my neck to my chest, to my stomach, then to my penis which was hardening. She looked at me with those beautiful blue eyes and smiled as she slid my penis into her mouth. I enjoyed a ten-minute blow job that got me hard and again made out with her as she came back up. I then went down on Nancsi and using my tongue ate her out, bringing her to orgasm.

Now she simply stayed on her back, pulling me up and wrapped her short legs around me. Again, she guided expertly my penis inside of her vagina as I drove my hard penis deep inside of her. “Oh!” and then “Yeah, go!” is what she replied. I then made love to Nancsi missionary style for the next forty minutes, taking our time, enjoying having sex together, and releasing all the sexual tension we had had for each other for a long time.

Finally, I felt my penis harden as my cum again flowed back into it, knowing this time I couldn’t stop it. I kept up a steady and constant rhythm as she moaned and enjoyed me. Nancsi suddenly dropped her legs, her arms fell to my side as she screamed in pleasure. I let my penis ejaculate again inside of her over and over, six or seven times. She squeezed and spasm as I ejaculated in her and together we enjoyed our orgasms.

After this love making, it was almost 1:00 pm. We had nothing better to do so we ordered room service, ate lunch, brushed our teeth (she had a spare) and then spent the afternoon making love two more times and holding, kissing, making out, totally releasing our emotions and sexual tension for each other.

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? This is Nancsi and I want to share my view what has happen. I have wanted Jeff for a long time but felt I couldn’t betray my husband. I realized though that life is too short not to go for what you want, and for the first time in my married life, I have meant a man who has my same interests, I know is interested in me and takes the time to be with me, to do the things I want to do and genuinely loves me. I had thought that he could be my platonic lover, but I realized that wasn’t fair to me or to him. I knew he had a sexless marriage and I decided to go after him, capture him, make him mine. I did that. Our sex is the best I have ever had and I am sure our emotional connection enhances it. I have no intention of stopping my sexual and my loving relationship with him and if in time, I can get him to leave his wife and be with me, I will.

In terms of sex, yeah, all day yesterday, a break last night so we could sleep and we just finished screwing each other when he started writing this. I love how his penis feels inside of my vagina, its like a glove with a hand for a perfect fit. Feels so good to have him inside of me. I love how his head rubs my g-spot when it goes in and turns me on, eventually bringing me to orgasm. I love knowing that his cum is in me, I can feel some of it seep out into my panties later and it reminds me of our love making. I am in love with him.

I love her and intend to keep this going for a LONG time. We are perfect and it just took us time to figure that out in our heads. Now that we have released our emotions and our sexual desires into reality, it is incredible.

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), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, To obtain a new partner

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? Nancsi

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? Getting past a stupid barrier that there was only one for us to this life. Life changes, people change and this allowed us to share our emotions and sexual desires and bring them to fruition. We are finding that friends with benefits or as we say Lovers with Benefits is an incredible thing and we deserve having this happiness.

What was the WORST thing about this hookup? Finally confirming that our marriages were over and now have to sort that out.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No and yes. We are both committed people who don’t fool around. Having said that, we have found that being happy together is what matters. Our sexual hookup is what brought us to the point, or sex did. For that it is okay.

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 look forward to being with Nancsi and she with me as much as possible.

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? Sex allows us to discover who and what we are and where we are. If I am just having sex for sex, that is kinda of stupid. Sex to heighten a relationship is a good thing be it with a friend, someone you know or have known for a long time. It allows you to examine where you are at. And yes, sometimes just getting laid is a good thing.

What do you think about the Casual Sex Project? Interesting

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

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