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What’s your gender? Man
How old are you? 49
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? CEO/Business Owner
What’s your current relationship status? Engaged/Married (open)
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? Always Looking, Rarely Tasting
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 1

Love Thy Neighbor

How long ago did this hookup happen? Two Days Ago

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

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 5’5″, has long blonde hair that reaches the middle of her back, brown eyes, smaller boobs, just enough to fill your mouth with no extra, thin, and fit.
Jen is my neighbor and I’ve known her for over 10 years. I consider her a casual friend, that sometimes we hang out with. She’s friendly, but cautious, and is usually not one to be alone one-on-one with a member of the opposite sex. I have always thought that Jen is very cute, attractive and like with any man, I’ve had my thoughts at times when she is wearing shorts and a tee, working in the yard or washing her car in the summer that I bet she’d be fun to screw around with. We’ve caught each other checking each other out or watching the other person while we are doing yard work. Jen has the habit of coming outside when she notices I am outside and being seen by me. I picked up on that several years ago.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Two days ago I knew that Jen’s husband was out of town for a two week business trip and I was taking a day off from work since my own wife was traveling for the company she works for. I was playing around in the flower bed when I looked up and noticed Jen watching me. She waved and I waved back and went back to watering my flowers and plants. Jen must have walked over as she startled me when she said “Hi Wade.” I jumped a little and said “Hi Jen.” She giggled knowing she had scared me and asked my how I got some of my flowers to grow so big. “Right location, fertilizer, and some luck I guess.” She asked if I minded if she picked some of my crocus, in white, purple and yellow, to which I said I didn’t mind.

Jen cut them and then asked if I had something to put them in until she got them back home. “Sure, come with me.” I took her into the house and didn’t notice that she shut the door behind her as I got a vase down. I turned and saw for the first time that Jen’s breasts were easily seen under her t-shirt, she had no bra on. In addition to seeing her breasts it was evident that he nipples had gotten hard and erect. Jen walked over to me, placed the flowers in the vase, put some water in them at the sink and then turned and placing the vase on the counter, lifted off her t-shirt.

Wow! Her round breasts were full and her nipples were hard and Jen smiled at me. She took two steps and while french kissing me, moved my right hand to her left breast. I instantly started squeezing and massaging it gently until Jen lifted off my own tee shirt. Naked from the waist up she rubbed my chest and I kept kissing and playing with her boobs. By now I was hard and I could feel Jen rubbing her lower body against my penis. Damn it felt good. “I never knew . . . ” I started to say and she cut me off by saying “Yeah you did. You just were too much of a gentleman to make a move. I’ve wanted you for several years, today I decided to see if you would. Well?”

At that point I took her by the hand, moving down the hall, stopping to kiss and exchange tongues in our mouths until I got her to the master bedroom. There we removed our shorts and me my underwear, Jen had none on, and I knew she had planned this all along today as she had said.

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? After we both were naked, I moved her to the bed and we laid down on it, side to side. I felt her right hand move down my torso to my penis and she began to stroke and play with it. I kept sucking her boob and nipple on her left breast as I moved my own right hand down her body, feeling her patch of pubic hair and then exploring her vaginal area. She moaned slightly as I played with her lips and inserted my finger into her vagina giving her a ‘come here’ motion with my finger. That really turned her on.

We slowly explored each other, kissing, touching and Jen finally smiled and went down on me. She looked at me while stopping and asked sincerely, “Teach me how to really enjoy this.” I asked her what she meant and she explained in 25 years of marriage- she is 45 and got married at 20 when she was still a virgin- she didn’t think she had had an orgasm and was more an object for her husband to satisfy himself on. I looked at her, her large brown eyes melting my heart, and I brought her to me, and passionately kissed her over and over again.

I began to touch her again, inserting my finger and working her g-spot. She played with my testicles for a few minutes and then got wrapped up in the pleasure she was starting to feel. I applied an even, gentle but firm pressure and motion with my finger as I noticed Jen began to moan slightly. This picked up for her as I continued to work her and used my other hand to now find her sensitive part of her clit. She was now totally into it and enjoying herself when she hugged me tight, lifted her butt off the bed and I felt a cold squirt on my leg.

At this point I moved her onto her stomach, had her support herself with her hands as she got on all fours and I used my hands to spread her legs slightly apart. I entered her from the rear, my penis now hard and slightly curved, ready for its duty. As I entered her, Jen moaned “Oh yeah, uhm!” several times as my penis went completely in and I withdrew it slowly. I did this several times, reaching around her and feeling her breasts when I was all the way in. I then moved into my position, where I could enter her easily and basically was on my knees at a 90 degree angle to her vagina and began to make love to her using a very steady and even pace.

Jen matched my rhythm and pulled and pushed my penis as I worked it inside of her vagina. “Uhm, so good, keep going” I got from her. Jen felt good for a mother of 3 adult children, and her vagina was now drenched in her wetness. We kept this up for a good ten minutes when I felt my penis begin to fill with cum and I pulled out. I didn’t want to ejaculate yet.

Jen looked confused at first until I said, “We have to try different positions to find out which ones work for you the best.” I was honestly wanting her to find which positions she liked and made her turned on as I know if the woman I am making love too is happy, I’ll have all the orgasms I could want.

I laid on my back now, my penis still hard and I moved her on top of me. She leaned forward kissing me deeply and enthusiastically as my penis now rubbed her vaginal area. I hit her clit and her eyes went wide. Jen now began to rub her vaginal area and her clit on the shaft of my penis over and over again. Suddenly she lifted up her body, and with me watching, squirted twice onto the sheets on the bed as she screamed out in pure pleasure.

Jen collapsed onto my chest and while moaning tried to get my hard penis back inside her vagina now. “Give it to me NOW!” she said in a raised voice. I guided my penis to her vaginal opening and inserted my penis inside of her vagina. “Aw, Aw YEAH!” Jen moaned as we began to really, really make love. This was now a woman in control and on a mission, and that mission was multiple orgasms. I kept my penis moving back and forth in her, about 2/3 of the way inside of her, as she worked her vagina on my penis. We were one, as one as I have ever been with any woman. More than just sex or fucking, I felt connected, really connected to her and her to me. She kissed me, deeply, her tongue filling and exploring my whole mouth. I felt her breasts swell and her nipples harden. My penis, filling with my cum, enlarged and brought Jen even more pleasure.

“Oh yes, Oh yes, Oh, Oh OH, OH AW!” Jen said with heavy breathing. Suddenly as she screamed out, I felt her vagina clamp down on my penis and I drove my penis farther inside of her. She screamed again and I could feel her vagina spasm as wave after wave of orgasm spread over her. I thrust twice and on the second time, I ejaculated my cum into her, feeling my wad shooting out several times into her vagina. She squeezed my dick, and naturally milked it as I continued to ejaculate multiple times in her.

My penis now slightly softened, but Jen kept it inside of her moving her butt and vagina ever so slightly enjoying that I was in her. She looked at me, kissed me, and said “I never knew it could be this good.” I smiled and said “Encore?” “Hell yes” was her reply. We then talked and kissed and fooled around, playing with each other, laughing. We got caught up in each other and made love again much like before.

I want to say I screwed Jen three times that day, before we had to go about the rest of that day, but Jen probably said it best. “That was the first time a man made love to me,” she said as we laid naked in my bed together after making love the first time. Jen wasn’t a virgin, that was for sure, and she had some experience but it was evident that she had never had an orgasm by her facial and bodily reactions. I can’t describe it but it was satisfying at many levels to be the first man, the second man she had ever made love to, that brought her to enjoy multiple orgasms. It ended with us taking a shower together, I did her doggy style in the shower and then I had to go about my day and she hers. As we dressed, Jen asked “Tomorrow?” “Absolutely” I said, winking at her. “Same time?” she asked. “Whenever your ready.” was my reply. “Now that I know what I am missing, I’ll be even more hungry.” Jen blew me a kiss.

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? We met the next day and made love the entire day. Five times perhaps, and I cooked her dinner. It’s nice being empty-nesters. We made love after dinner and ended up spending the night together. We found we have a lot in common but are content for now to leave this as friends with benefits. Jen wants to keep the sex going she said for a LONG time, as it is satisfying to her and she isn’t the type to want to go mess around with a lot of people. She asked me if I would keep my sexual activity limited to her and my wife, and I easily agreed to that. She said she would only do it with her husband when he demanded it, about once a month. So we are meeting up again this afternoon for round and day 3. Glad our spouses are traveling!

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), 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? Somewhat

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? None

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? Connecting, not just having sex, but making love. It was satisfying to bring Jen to her first orgasms and to continue to do that. More importantly we found we actually have a lot in common, enjoy each other and the making love/sex and yeah.

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? No. Not one to always fool around but in this case, Jen presented, I was attracted to her and liked her somewhat, so I did. No regrets. My wife doesn’t enjoy sex since entering menopause so this works.

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? Always more to the story in terms of trying different positions etc.

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 is a good way to meet your own needs, but sex is more meaningful when it fulfills a need for another person. I believe sex always fulfills a need for yourself and your partner. The level of that need determines if it is a one night stand, fuck buddies, friends with benefits etc.

What do you think about the Casual Sex Project? Interesting. I’d like to see it listed by age, like 18 to 30, 31-40, 41-50, etc. or being able to sort it that way.

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

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