What’s your gender? Man
How old are you? 53
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? University Administration
What’s your current relationship status? Married, Sexless
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? Nope
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 2
Love Your Neighbor
How long ago did this hookup happen? Today
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 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? Jen is five foot four, blonde shoulder blade length hair, brown eyes, slim, tight butt, has 3 adult children, and is married. Jen and her husband have been our neighbors for over 15 years, and we have a good relationship with them. I’ve always been attracted to Jen, though I never thought of doing anything about it.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? At a neighborhood birthday party for an elderly neighbor, as I went to leave, she stuck her hand out to shake it saying she didn’t know about hugs since people are sometimes weird. I smiled and told her I am always open to hugs from people I know (I am an affectionate man). She then gave me a hug, one that lasted just a tag longer than it probably should have and she whispered in my ear so only I could hear it, “More of those to come.”
I left and walked home across the street, and her comment left me wondering but I didn’t give it much thought. The next morning I arose early and went about my routine and left for work early. I had to catch some people and pick up an item. Then, I came home to work on a course so I wouldn’t be disturbed. As I was working about an hour later, the doorbell rang and I went and answered the door. There stood Jen who asked if she could come in as she needed my help. I let her in and asked her how I could help her. With a sheepish smile, Jen looked at me and said, “I’ve never thought I’d try this, my husband has always been my one and only lover, but I am attracted to you and have been for a while. May I have another hug? I want to see how it makes me feel.”
Well, of course, I opened up my arms and Jen easily fit into my 6’1 frame. We hugged and held each other. For a couple of minutes, we just simply hugged and she said, “That feels so good.” With that, she tilted her head back off my chest and looking up at me said, “Kiss me.” I looked at her and saw that look of wanting me, so I reached down and gave her peck, teasing her and seeing what she had in mind. “No, a real kiss like this,” came Jen’s reply. She reached up and I felt her tongue press against my lips and as I opened my mouth to kiss her, our tongues discovered each other.
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? With that, my course was on hold. We began making out and her arms rubbed all over my back and mine on her back. Slowly, she brought her hands to my chest and began to unbutton my dress shirt. Watching her hands undo my shirt, realizing that it had been 8 years since I had last had sex with my wife who no longer could, my penis responded instantly. I could see her breasts and nipples sticking out; Jen hadn’t worn a bra.
Jen undid the buttons on my shirt and on my wrists and removed my shirt and tee shirt. We kept kissing, and I easily removed her tee shirt and sports bra revealing two perfectly round and mouth size breasts with erect nipples. I felt them, gently touching and caressing them as I enjoyed making out and feeling her breasts. Five minutes later, I moved down from her mouth to kissing her neck, then kissing and sucking her breasts. Jen sighed with pleasure as I enjoyed her breasts. She undid my belt and my pants, removing them and my boxers in one motion, leaving me naked except for my socks.
I kissed down from her breasts, down her navel, and removed her sports pants and panties. I then had her sit in a recliner nearby as I removed her socks. I used my hands and arms to part her legs kissing her right foot, then right calf, then up to her right inner thigh and finally began licking and kissing her vaginal area. Jen’s eyes went wide as I began to work on her clit and her vagina with my tongue and she moaned, “Wow!” I looked at her and asked, “Never had oral?” “Never,” was her reply, and with that, I went to work. I worked her inner and outer labia lips then up and over her clit and did that multiple times, causing Jen to moan in pleasure and to get really horny. “Want to stop?” I asked at one point. “No way, this is incredible, don’t stop!” was Jen’s reply. I kept working her clit and then hardening my tongue like a dick and using it on a ‘come to me’ motion inside her vagina, nailing her g-spot. After fifteen minutes of enjoying oral sex with me, Jen screamed as her body momentarily shook with euphoria as her orgasm spread over her body.
Jen pulled me up to her and began making out with me slowly as she enjoyed the afterglow of her first oral orgasm. I looked at her and felt her vagina and it was soaking wet, her breasts and nipples still hard and so I grabbed her hand and led her down the hall to the master bedroom. We laid down on the California King and began to make out. I was rock hard and Jen now looked at my penis and began to stroke it. “That’s bigger than I am used to,” Jen shared as I fingered her slowly, turning her on again. “Really?” I said. “Yeah, if I knew you could make me feel this way, I wouldn’t have been so shy all these years.”
Jen now had a hungry look in her eyes, and we moved from a side by side position, to where she assumed the missionary position. “I want you James,” escaped her lips in a soft and seductive whisper. “I want you too!” I answered hungrily. I moved into a modified missionary position, with my weight on my hands and mainly on my knees as I brought my penis up to her vagina. I rubbed my penis using my body all around her vagina and Jen simply licked her lips a few times. “Please,” Jen said and I asked, “You sure?” “Yes, please go!” Jen said moaning. So as I moved my penis head around her vagina and lips, I slowly drove just the head of my penis inside of her vagina. “Oh, oh,” Jen moaned and then I withdrew and drove my penis in just a little more, and then withdrew slowly. Jen again licked her lips and moving her feet to the side of each hip, drove her hips and vagina down hard on my penis. I completely filled her vagina as Jen sighed loudly in pleasure.
I drove deep in her vagina, completely in her now, the base of my penis rubbing the outside of her vagina and I thrust a few times. Jen whispered “I want to enjoy this!” so we slowly made love, moving back and forth, in and out. I increased the pace at times and slowed or stopped at others. Finally, I withdrew and Jen instantly grabbed my hard penis to insert and I said, “Wait.” I moved her to the side and I laid down beside her, lifting her leg so I could penetrate her again. Slowly we made love and Jen asked what position this was and I told her, “Spooning.” “So good,” was Jens reply as I held her, fondled her breasts and we made love.
After ten minutes of spooning, I withdrew and Jen looked at me as she was getting pretty horny and close by now to another orgasm and I laid on my back. I moved her to where she straddled me and grabbing my penis, Jen drove it up inside of her vagina. “Oh, that’s my favorite!” Jen moaned loudly as we began making love with her on top of me. Jen now was in control for the first time in her life of her own orgasm and love making and she loved riding me. Jen alternated between fast and slow, between leaning forward and kissing me, letting me rub her breasts to riding and driving my penis deep in her. Faster and faster Jen started going saying “Oh yeah, Oh YES!” and then over and over again “Oh, Oh, OH, OH OH OH OH OH OH OH!!!!!!!!” Jen was now thrusting so fast on my dick, it seemed like a blur as I watched her drive it in and out, deep and deeper inside of her. I felt my ejaculate rising and knew I was close. The intensity of our love making was incredible, bonding, and so intense I had never screwed a woman like this before. Suddenly, Jen screamed out as her body shook with euphoria yet again and she collapsed on top of my chest as my penis now ejaculated its full load completely once, then in smaller ejaculates four more times deep inside Jen.
Jen began making out with me, as she used her muscles to squeeze my dick (she loves working out), and she moved her butt from my left side to my right side to get all of my sperm inside of her. We held each other, and as we kissed, we slowly began to talk.
“That was wonderful!” Jen said. “I didn’t know sex could be so incredible!” “Have you only done…” and Jen cut me off, “Yeah, the position with the man on top of me, that is the only thing my husband does. Are there other positions?” Jen asked. “Yes,” I replied. “Well, I guess you’re going to have to arrange to show me them and over time we’ll see which ones we like doing the most!” With that Jen got up and so did I we got dressed. Her daughter and grand-daughter were coming over and she needed to get back home and I needed to get back to work.
“Same time tomorrow morning?” Jen asked kissing me? “Whenever you want!” I eagerly replied. “Our secret?” Jen asked. “Yes,” I said and Jen winked and said, “Good, cause you’re all mine.” We had agreed to take it as it came with no commitments, but Jen told me that she loved discovering that there is a real sex life and she intends that for a few years, we take the time to find out what she likes and what positions we like with each other. I am more than willing. Man, it is a good thing to love Your neighbor.
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? Well, it happened this morning and Jen is coming back at 2:00 pm for round two today for 3 hours before anyone else comes home. I am finally open to this, and I am so glad we crossed the line and opened up. Jen knows about our sexless marriage, it is what drew her to me, well one of the things, and she wants to make up for all the lost years of no fun with sex. I am more than willing to be her partner on this.
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, 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? First, the sex was incredible, like it was for the first 15 years of my marriage. Jen cannot get enough and that is incredible. Exploring and doing new things with each other is wonderful also. Bonding with another human sexually is good also.
What was the WORST thing about this hookup? Nothing
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Just open to trying new things with Jen.
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? If in a committed relationship one partner cannot, I am open to finding another partner to share sexual experiences with since sex and physical intimacy are part of the human condition and I feel needed for overall health.
What do you think about the Casual Sex Project? A lot of experiences here. Some are different but each their own.
You have a hookup story to share? Submit it here!