What’s your gender? Man
How old are you? 48
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? CEO of Own Business
What’s your current relationship status? Engaged/Married (monogamous)
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? Love women
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 1
Love thy Neighbor
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? Judy is 5’4″, blonde hair that is mid back in length, blue eyes that shine, fit, showing her 46 years somewhat and has a tight ass for having had 3 kids. She is reserved, quiet and observant.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Judy is committed to her family as I am to mine. We have been neighbors for over 11 years and we both have caught each other checking each other out as we are both outside. Judy will purposely come out of her house and work in her yard if I am doing the same. Judy’s two older kids are out of the house and she has a younger son just entering his senior year in high school.
Judy’s husband is controlling, very much so and this week he went out of town on a business trip. So happens my wife, an accountant is out of town on a trip for a major client this week. I was off for the last couple of days, well, off one day and working from home. I went outside to welcome the landscaper who was going to fix my broken sprinkler pipe the next day and got that arranged. As he drove away I noticed Judy outside and she waved at me. I waved back and smiled and went about my work in the yard.
A moment later, I noticed that Judy had crossed the street and was admiring our day lilies and other summer flowers. We talked about what I had done to get them to be so large and beautiful this year, lots of free moisture and fertilizer. At this point, I thought our small talk was over so I moved to say goodbye and head into the house when her right hand grabbed my arm startling me. I own about half in a solar company and though Judy’s husband was opposed to getting solar on their roof, Judy now inquired informing me that if the savings are real she would do it and convince her husband that they needed it.
We went inside and I pulled up my power bills from before our solar panels and then after. Judy was amazed at the savings and inquired about the batteries we had installed that allowed us to run the house off the grid if we wanted. She wanted to see them so I took her past our spare master/guest room and to our utility room. I showed her the batteries and explained how they worked. She thanked me and then blocking my way as I thought we would leave, Judy just asked straight up if I found her attractive. “Yes,” I replied. She then proceeded to take my hand, lead me down the hall to the spare master bedroom (we had an addition with a larger master added which was our bedroom) and she led me in there.
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? In the room, she locked her arms around my neck and said, “Kiss me.” I hesitated, “What about De. . . ” and she cut me off. “I don’t care about him right now, kiss me NOW!” With that, I thought what the hell, and I kissed her. The taste of her mouth was sweet and minty, she must have prepared before coming over and I loved how her tongue rolled over, under and mingled with mine. “Uhm” Judy softly whispered. We kept kissing when I felt her arms lower to my waist and remove my tee shirt. I then removed hers and saw she had no bra. Her tits were perfect, round, with hard nipples and large enough that when you suck on them they won’t fit completely in your mouth.
I began to fill her boobs and continued to kiss her when she undid the belt on my jeans, undid my buttons on my zipper and lowered my pants and boxers down to my ankles. I stepped out of them, as she removed her bottoms. I looked at her fit middle age body and by now, I was hard as a rock. I saw a thin strip of pubic hair trimmed and leading to her vagina. Our bodies now embraced, her right hand now gently stroking my dick as I let my hand explore her vaginal area.
She played with me and I with her, toying and teasing for about 10 minutes. I led her to the bed, turned down the covers and got in them with her. We laid side by side, and I sucked her full breasts and her nipples. After a while, I lifted her leg and guided my dick to her vaginal opening. Still holding my hard penis, she guided it into her vagina until I was completely inside her. Judy moaned, “Oh hell yes.” and “Damn, that is so good.” I slowly began to push in and withdraw partially increasing the pace over time. Slowly, Judy worked up to where she was slamming my penis inside her luscious and dripping vagina. Judy suddenly started moaning in pleasure, sounds I can’t write for I don’t know the words and then she screamed in sexual ecstasy as I felt her vagina convulse on my dick over and over as she enjoyed her orgasms.
I hadn’t cum and that was the purpose. I came close but I held back. Judy as she now kissed me in afterglow’s magic, asked why I hadn’t cum. I explained I wasn’t done. Judy lifted her eyes and said “My husband is done in about 10 minutes. What more is there?” I kissed her passionately a few times, then kissed her cheek, her neck, sucked her boobs and tits, then began kissing down her navel. Judy finally understood what I meant and stopped me. “I’ve never had oral before.” “Why?” I replied. “My husband thinks it is wrong.” “Let’s see what you think after I am done!” I replied.
I then worked my mouth and tongue down past her belly button, putting my face in her trimmed bush. I made it down to her vaginal area and began licking her and inserting my tongue into her vagina, making a curled motion and finding her g-spot. This turned her on and Judy’s hands came to my head and rubbed my hair. I eventually made her whole vaginal region completely coated with her wetness. I now came up from her vaginal region and brought my harden dick up to her. Several times I rubbed the shaft of my penis against her clit causing her to moan. I moved her to where Judy was on top of me, and she began to rub her clit against the shaft of my hard penis. Five times she did this, all the time moaning with her face in absolute pleasure. The sixth time she rubbed, then rubbed again quickly and quickly again and her hips went up in the air as she squirted onto the bed sheets as I watched.
Judy screamed in pleasure, falling on my chest and kissing me. She tried to use her right hand to guide my hard penis into her vagina but didn’t have the strength after the clitoral orgasms she had experienced. I grabbed my shaft and put my penis into her welcoming voluptuous vagina. Judy screamed out as my penis entered her, and I drove it deep, as far as I could in her. She wiggled her butt and her vagina around with my penis in her, squeezing as she did so. We made love, not just fucking, but we made love at that point.
Judy on top of me, laying on me, thrusting my penis in and out as her pace gradually quickened. I drove my penis into her and helped withdraw it, sometimes completely as I then rammed it back inside of Judy. Judy’s pace now quickened to wear it was a blur as we fucked and made love. “Oh, Oh, OH!” Judy moaned. I felt my cum now fill my penis, and my penis increased in size. “Awhhhhh!!!!” Judy moaned again and again as she rapidly drove my penis in and out. I felt my penis come out, and slide up her vaginal area and then Judy drove down and I entered her. Her legs now spread out as she squeezed me with all the strength of her lower body and vaginal muscles for being fit could muster. It sent me off and I exploded inside of her. Each time I came, Judy squeezed and moaned, and then milked my penis to get every ounce of cum out of me.
We kissed, smiling at each other, kissing more and slowly talking. Judy explained she had wanted to fuck me, no make love to me for years. She wanted someone who was more tender, kind and caring than her husband. More importantly, he had been her only lover and in talking with her sisters, she realized there was more. So she had decided to give me a ride to see if I could deliver.
“Did I deliver?” I asked. Smiling, Judy said, “I want more so you more than delivered.” We kissed and did foreplay, made love again, had multiple orgasms and afterward, I taught her how to give a man a proper blow job. She mastered that, and by the time we were done with 3 times having sex and 1 blow job, I don’t think for the next two hours I could have done it! Well, I took her in the shower, and there with her sitting on the bench we have in that shower, I ate her out again, giving her an orgasm and then I did her from behind. After that, we were done for the day
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? After we dressed and tore ourselves away, we agreed to meet once a week at one of our houses, and engage in our rendezvous. Judy agrees and the next day, I found I wanted her again. I went over to her house, knocked on the door, (after he teenage son had left for work) and when she opened the door, entered, shut the door and kissed her. We made love twice more that day.
I think I am in this for the sex. I am attracted to Judy, like her a lot, and if we were single, I date her to see if it led anywhere. I think Judy is split on what she wants. First and foremost is she wants really great sex to make up for the lost years as she calls them. Next comes some emotional connection and then we’ll see.
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, Just happened, I don’t know why, just went along with it, It was easy / convenient
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? No one.
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? Feeling great about having sex again! Freedom to bring pleasure to my partner and lover and watch them truly enjoy having sex together.
What was the WORST thing about this hookup? Danger of being caught by her husband. Most hookups are at my house as I have an open marriage.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Just that you never know what someone is thinking or wanting. I don’t believe in a lot of casual sex, but man, when the old is old and tired out and she just assumed doesn’t want to do it, and then to have someone want to do it with you, that is exhilarating.
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? Just enjoy Judy and look forward to more hook ups!
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? I started masturbating at age 12 and by 15 had had intercourse. Teenage years were rather wild. I would have a girlfriend and then have 2 or 3 friends with benefits. Same in college. Settled down when I got married and Judy is only my second lover since I was married. My wife has had 1 but for 6 years. People need to get over the taboo of sex.
What do you think about the Casual Sex Project? Keep it up!
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