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What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Professor
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? Enjoy Sex
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 2

Once Upon the Only Time

How long ago did this hookup happen? a week ago

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

How would you best classify this hookup? One-night stand

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? Beckie is a good friend of my wife, and has been for a long time. Never married, though she would love to be. She is 5 foot 6 inches tall, rather large breasts, nice butt and skinny. Brownish hair learning to light brown with hazel eyes. I meet her just over 3 years ago at my wife’s company Christmas party after Beckie began working with my wife. Beckie is intelligent, quick witted and dates a lot looking for her husband. She is 30.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My wife was out of town on a business trip to review a client’s accounts and Beckie was going to fly back to California where she is from. From time to time if a brother or sister cannot take her to the airport, she spends the night at our house and my wife or I drive her and drop her off at the airport. We pick her up and then Beckie spends the night at our house and the next morning drives home, having left her car at our home for her trip.
This was such a time and Beckie’s siblings could not take her to the airport. So she came and stayed with me, since all of our kids are grown and out of the house. Beckie showed up around 5pm and I got her settled into one of our guest rooms, and then made her dinner of a spinach salad, strips of flank steak with sauteed mushrooms and vegetables. It was a good meal if I brag. We talked and I caught up on her social life, and how the couple of guys she really liked viewed her more as a friend then as something more. I listened more than I talked and around 9pm Beckie said, “I wish more men were like you, and simply listened!” She then came over and gave me a quick peck on the lips, followed by a good long hug. That started it for me. I felt my penis stiffen and I know Beckie felt it too as she looked at me and smiled. She broke the hug and smiling, gave me a wink with her right eye and said “Good night!” She then bounded down the stairs to her room, and I heard the door shut. I cleaned up the dishes, loaded the dishwasher and ran it I then locked up and went to my bedroom, and shut the door, almost all the way, but not entirely so the door didn’t latch.

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 know got ready for bed, undressed and crawled into the king size bed we have. I turned on the TV and flipped the channels, finding nothing appealing. So I pulled out the book I was reading and began to read. I read for a good forty-five minutes and then must have fallen asleep. I awoke and instantly felt that someone was in the room.

Sure enough, sitting on the bed next to me was Beckie, watching me. She lifted the book off the bed, putting it on the night stand and smiling again at me, asked if I had ever cheated on my wife. “No,” was the honest reply. “When was the last time you did it?” was Beckie’s reply. Now I had to admit, it had been a good 18 months since I had last screwed with my wife. Menopause was not being her friend or friendly to our sex life and I was damn horny. I looked at Beckie and said “Over 18 months.” Beckie now leaned over me, and her piercing hazel eyes held my deep brown ones and said, “Yeah, she (my wife) had said that.” Beckie now leaned all the way down and her lips pushed onto mine, kissing me and after a moment, I felt her tongue enter my mouth.

I had noticed that Beckie was wearing a one-piece nightie and as my body responded to her kiss, I felt her hand on my left thigh as she worked it up to my crotch and her index and middle finger brushed against my balls. I reached my arms and hands up to her nightie and undid the strings holding it together. It fell away revealing her naked body and her two large breasts with erect nipples. I instantly began to gently rub and massage her breasts as she sighed throughout kissing.

We kept kissing and Beckie removed my tee shirt, then my boxers, placing us on equal, naked grounds. I dropped my right hand off her breasts and felt her smooth and cool skin with my hand as I worked down to her belly button, her naval and then to her furry trail of pleasure. I found her vagina and Beckie was wet, soaking wet. I touched her and she moaned. We kept kissing, our tongues now enjoying being interwoven and explore each other’s mouth. Her right hand now was massaging my balls, her fingertips gently scratching my ball sack. Beckie now moved her hand after a good 15 minutes of foreplay up to my now not stiff penis, but extremely hard penis. Beckie smiled as she said to me “I think I am going to like that!” I asked “How long for you?” “Only one guy, four years ago for about 3 months.”

I was leaning on three pillows behind my back and now rubbing her clit and inserting my finger into Beckie’s vagina, turning her on and making her moan slightly. She moved forward now, wiggling her butt so that her vagina was over my hardening penis. I quit playing with her and returned to playing with her breasts. She leaned forward and we made out more when I felt her hand grab my penis, Beckie said, “Make love to me all night?” I simply nodded, making the commitment to violate my marriage vows for the sake of screwing one of my wife’s best friends and getting laid.

Beckie now used her right hand and guided my hard penis to her vaginal opening. We stopped making out and simply held each other with our eyes as I then pushed slightly up and the head of my penis entered her moist, warm, wonderful vagina. Damn! I had forgotten how great this felt. I now pushed my hard penis completely inside of Beckie until I felt the base of my penis completely touching her pussy area and the head of my penis was touching her cervix. I knew what that meant so I was careful, and careful to keep the pressure and stimulus going.

Beckie now moved back and forth on top of me, my penis deep inside of her and only coming out about 1/2 way when we pulled back to then shove it in. She leaned forward and kissed me and as we made love, at one point I said “Condom? “Beckie shook her head no and began to screw even faster. For the next twenty five minutes we made love, going fast, slowing down, at one point almost stopping, while Beckie stopped and I pushed my penis back and forth in her. Beckie then leaned foward again and went for it. She went crazy with the base of my hard penis stimulating her clit and my penis stimulating her g-spot. Faster she went, moaning then screaming loudly “Oh, go, GO, I WANT IT, I WANT IT, I WANT YOU!” This turned me on as she kept saying it and moaning “Oh Yeah, Oh Yeah, Oh Yeah, Oh, OH OH OH OH OH OH!!!!!!” Faster Beckie went, her chest, her breasts, her neck and then her cheeks and face turning red and suddenly she screamed “YESSSSSSSSSSSSSSSSSSSSSSS!!!!!” and it all came together for her.

I could have shot my cum at that time, but I didn’t. I kept my penis hard, and as it filled with my cum I and Beckie who had now fallen on my chest, felt it engorge with my sperm and cum and enlarge bigger than it had been. Beckie rolled on her back, and I moved to where I was kneeling in front of her vagina, and Beckie spread her legs again. I moved into position, her right hand taking my penis and guiding it into her vagina I drove deep. Beckie gasped with pleasure again and I know began a very steady, consistent, movement in and out of her vagina, keeping only my head in her when I withdrew and then driving deep in her.

After fifteen minutes of making love like this, I drove deep inside of Beckie and without withdrawing more than a couple of millimeters, drove my penis deep in her vagina, touch her cervix. Beckie’s eyes went wide as I rubbed her cervix with the head of my hard, very hard penis and did this for the next few minutes. I could see Beckie’s breasts swell again, her nipples going hard and super eject. She turned red again in her chest and then it spread up her chest to her neck, from there to her face and finally her cheeks. For the firs time tonight she closed her eyes and her vaginal muscles instinctively began to squeeze my hard penis. I felt my cum flow fully back into my penis, swelling it, making it increase by a good inch or two in girth as Beckie screamed in pleasure “FUCK ME! FUCK ME FUCK MY PUSSY!!!” and then “Oh yeah, Oh yeah, so good, oh more, MORE!” as I kept up my rhythm. Suddenly I felt her whole vagina quiver, and then convulse as she then squeezed hard down on my penis as it’s head was rubbing deep insider of her on her cervix and stimulating her g-spot at the same time.

I shot my first full load into Beckie as her arms fell to her side and she began to moan loudly “Oh yeah, oh YES, YES, MORE!” I kept cumming in her, shooting load after load of my sperm and cum in her. Beckie using her vagina now milked by penis, squeezing out every possible ounce of my cum into her vagina. For ten minutes we held, kissed, smiled, and enjoyed the pleasure of the moment. I stayed in her vagina, as she continued to squeeze my penis and get every drop of my cum inside of her.

Afterwards we stayed naked under the covers and talked. We never mentioned my wife or anything and I honestly didn’t feel guilty. It felt damn, and I mean damn good to make love to a woman who wanted to make love together. Slowly her hand worked its way down to my penis and she began to play with it as I touched and sucked her breasts and nipples. about forty five minutes later Beckie was wet, I was hard, and this time we did it spooning, doggie style and then ended up back in the modified missionary style. I made Beckie have two orgasmic cycles (multiple orgasms) with my penis and I eventually shot my sperm and cum in her again multiple times. That night we only slept for 3 hours and made love 2 more times for a total of 4 times that night. My wife was gone again the next day and Beckie moved her flight so we ended up making love all the next day and night, for a total of 14 times in those two days. I was worn out when I dropped her off at the airport two days later. She even admitted to being a little sore but said it was worth it. She had never had an orgasm until then. For me, it was like 18 months was worth waiting for sex like that.

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? Beckie went home to California to visit family for the holidays but is returning in early January. My wife is out of town and Beckie informed me when I dropped her off that I need to take 3 days off as I am going to make love with her even more when she gets back. I planned for it as my wife is out of town again. I later found out that my wife and Beckie had arranged for this to happen. Since my wife had lost all desire and knows I have a very strong desire, and Beckie is willing to make love with me, it works for all 3 of us. My only concern is I used no protection with Beckie and she could easily get pregnant. Then again, I have a very low sperm count so perhaps not. My wife says not to worry about it and to just enjoy my time I have making love with Beckie.

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

What were your motives for this hookup? Attraction to partner(s), Just getting laid with a pretty woman I was attracted to

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? My wife knew it was going to happen, she basically arranged it as Beckie was feeling lonely and she knew Beckie was attracted to me so she told Beckie to go and make love to me.

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? Finding out that though my partner has lost all interest in sex, she recognized my strong desire and found a friend in a similar situation and got us together. The sex was some of the best I have had because at middle age, I KNOW if I please the woman I am with, I WILL find the pleasure I am seeking and needing and there is not greater pleasure then helping a partner get what they want as you share together in the moment.

What was the WORST thing about this hookup? The time I spent worried about her getting pregnant. No sexual disease as she doesn’t sleep around but I did fear getting her pregnant as I came in her a LOT. Waste of time to worry. If Beckie gets pregnant it is taken care of I found out.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I am not one to just go get laid by anyone I can get to go to bed with me. Those days were in my late teens and early twenties when I was only concerned with myself. However, this affair taught me that I can maintain my beautiful, wonderful platonic marital relationship and have a lover where we both meet our needs. If Beckie ends it, I would look for another probably for the same thing.

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 LOVED having an empty house. Besides the bed, we did it on our chaise, our couch, our hot tub, our lap pool, in the shower. Just have to make sure the windows are down.

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 was common in my youth. I lost my virginity in my late teens and was sexually active through my mid-twenties until I got married. 30 years of faithful marriage, honestly 3 of those years with no sex. Still, I love my wife but I still want to make love so a casual sexual relationship is a good thing on the side if you find someone who is like you are I think.

What do you think about the Casual Sex Project? Interesting. Some people go wild here, some just like I did, an affair. But sex is sex and it goes on far more than we think or know about and I think more people cheat then we know.

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