My Cranky Neighbor



What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Western United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Lawyer
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? Hungry, Willing, Pleasure my Partner First
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? 5

My Cranky Neighbor

How long ago did this hookup happen? 1 week

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

How would you best classify this hookup? Fuck-buddies / Booty call

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? Cate is ten years younger than me at 42, a mother of one and a teacher. She keeps to herself, has shoulder length brown hair with blondish highlights in them, is about 5’4″ in height. She has large boobs, a nice butt, and is cute.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Came home from work to escape the office and do some work on a case without getting interrupted. I pulled in, walked into the house, got a bottle of water and went to my office. It was around 12:30 pm and I thought for sure I would get 4 hours or more of quiet time to work. At around 1:15 the doorbell buzzed, and I went to answer the door. At the door to my shock was Cate. I had always looked at Cate when we were both outside working around our yards and stuff, and I had admired her boobs, I love breasts and she has two large ones. She is cute enough, not drop down gorgeous but cute. I had always carried the thought in my head that I bet she would be a great fuck.
Well, Cate was off that Friday as a comp day for Parent/Teacher conference and she was going to cook some cookies but realized she needed some more sugar. To save her the hassle of running to the store could I give her 4 cups. “Sure” I told her, inviting her in and walking to the kitchen. I pulled out a Tupperware holder and measure 4 cups of sugar, putting the lid on. The whole time she smiled at me and as I walked over to give her the sugar, she took it, put it on the kitchen island and said “You know, I have always thought you were cute.” With that she held my gaze, put her arms around my neck and laid a full-on kiss on my lips, her tongue darting into my mouth. Yeah, Cate had planned this with the sugar to find out my reaction to her move.

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 a couple minutes of french kissing, her right arm dropped to my side and she looked at me and asked “LIke that?” and at the same time her arm moved her right hand to where it began to rub my balls through my dress pants. I was interested, my wife is out of town and I thought, what the hell, why not. My sex life was average at best, only once or twice a month if I was lucky and I had fucked my wife in four months. “Yeah, I liked it” came my reply and I leaned down and kissed her again.
Her hand kept rubbing my balls and then started to rub my dick, as it grew hard. I began to rub her boobs and after about five minutes of this, I got a slight “Uhm, yeah” from Cate. “On the counter then?” Cate asked, smiling. “No” as I now took her hand and led her down the hall to our king size bed. I shut and locked the door, not knowing why no one lived her but my wife and I and she is gone for a couple of days. I kissed Cate now, surrendering my logic and my passion to her and she replied. I removed her shirt, then her bra to reveal two beautiful and large areolas with hard and large nipples. Her breasts were large and my hands went to work playing with her nipples, putting some saliva on my fingers as I rubbed them. I beat her to her undressing more as I undid her pants, and she stepped out of them. I could see through her panties her hairy pussy area, so I stopped fondly her tits and nipples and laid her on the bed. I then slowly removed her panties and then kissed her toes, on both beet, then both feet, and then working my way up her left leg, up to her pussy, skipping it, as I kissed and licked down her inner right thigh and then repeating that up her left leg and left inner thigh.
By now Cate was hungry, and I could smell the wetness of her pussy. My tongue now came up and worked over her pussy lips. and just was with the legs, I went down one side, and up the other. I did this for the next five minutes, turning Cate on. I finally brought my tongue up to her pussy and making my tongue hard and round, I inserted it like a dick inside of her vagina. I then used my tongue in a come here motion, stimulating her g-spot and Cate raised her ass into the air several times as I did this. I slowly kept this up for several minutes, then using my tongue, I worked up to her clit, and gently and carefully, I didn’t want to spoil her fun or end it with me, I check out her clit and found where she was most sensitive, on the right upper side about 1:00pm to 3:00pm if her clit was a clock. I worked that slowly, gently back and forth using the top, flat part of my tongue and then using the tip of my tongue. Cate began to moan now, and her moans of “Oh yeah” and “Oh, Oh, OH!” go faster. Suddenly she raised her ass up in the air as she convulsed and Cate threw me off of her and squirted a long streak on the bed.
Cate collapsed, her body having multiple orgasms from the stimulus of her clit and vagina, and I laid next to her. She rolled on her side eventually, and rubbed my chest as she smiled and said “Damn, I never have had it like that before.” “More to come I think” I replied. “Hell, you better be ready to go a long time.” Cate now undid my pants, pulling them off, removing my boxers to reveal my hard, thick 7 to 8 inch dick. Cate played with my dick, grasping the base and squeezing hard, making it grow even thicker and harder. “Damn, I can’t wait to fuck that!” Cate replied. “That is helluva bigger that my husband’s as her eyes widen with excitement. “I can’t wait . . . ” I was going to say to ram it in you but Cate went down quickly and began to kiss my dick.
Cate slowly used the tip of her tongue on my penis hole and on the area just above that on the top of my dick. That drove me wild. She felt and I felt my dick immediately respond as she kept this up. I felt my cum load into my dick, making it swell and grow even thicker. Cate’s eyes got wide and she turned her body now, so her pussy was in my face. We assumed the traditional 69 position and I used my tongue to stimulate her again, first her pussy lips, then her vagina and when I went to go for her clit, she stopped licking my dick and said “Like my cunt” so I did. I harden my tongue like a dick and began to tongue fuck her vagina. All this time Cate kept licking my penis hold, working up to the top of my penis on the very top and edge and back down. Slowly she started licking the entire top of my dick’s head and I started to really fuck her with my tongue. Suddenly I felt Cate take my dick and shove it all the way inside her mouth to the point she was using her mouth as a pussy, and driving my dick in and out of her mouth. Rapidly we built up our excitement and suddenly I felt her pussy vibrate begin to convulse and I let my cum explode inside of Cate’s mouth.
Cate now sucked my dick, milky it with her mouth to get every drop of my cum out as she came from my tongue fucking. We collapsed after a few minutes and then changing position, we simply held each other. Her mouth sought out mine and Cate asked/ordered “Kiss me” I did, she did, our tongues entering our mouths. I could taste the saltiness of my cum and now understood and she could taste the richness of her pussy juices.
We made out for ten minutes and then she began to play with my balls and I her breasts. “Your a helluva a lot better than I thought you’d be.” Cate whispered. “What do you mean?” I asked. “You don’t drink or party, and I get why (parents were alcoholics and I wouldn’t risk that ever) but man, now I know why. You fuck like no man I’ve been with!” With that she kissed me, my fingers sought out her cunt and I played with it, fingering it as she stroke my dick, making me hard.
Twenty minutes later, my dick was hard as a rock and Cate was as wet as the Pacific Ocean. I was kissing her, banging her with my finger, she still stroking my dick to keep me hard, but not enough to make me want to cum. “What position?” I asked. “Just fuck me” was Cate’s reply. So I did. She was on her back, I assumed a position on my knees in front of her, my hands supporting my body so my weight didn’t press on her, and I used my right leg to begin to move her left leg and Cate just simply spread her legs wrapping them around my back and using her right hand, guided my hard dick to her pussy where I easily drove it all the way in slowly, allowing Cate to treasure each inch, each millimeter as it entered her.

Her eyes grew wide, Cate smiled and said “That’s so damn good. Fuck me” I began to now slowly pull my dick about 1/2 to 3/4 of the way out of her vagina and then drove it all the way. When I drove it in Cate sighed “Yeah, oh, more!” For the next three minutes, I kept up my rhythm and slowly worked Cate up. I got harder of course, and at about five minutes, I felt my cum flood into my dick so I stopped the motion. Cate’ said “No, fuck no, I want more!” I then withdrew and got on my back and moved Cate into position to be on top of me. “What the hell now?” she asked. I leaned her forward with my hands on the sides of her boobs, and said “Use your pussy to drive down on my dick.” Cate did so and her eyes got wide again, and she drove my dick slowly and completely inside of her. Cate had never been on top as a woman and now realized she was in control. She let my dick settle down so I would shoot my cum all inside of her and then she went to work, alternating between slowly and quickly driving my dick inside of her pussy.
Finally she sat up, my dick went deep inside of her, and I simply slowly pushed it up all the way inside of her vagina, completely, then slightly down and then back all the way in. For five minutes we gave each other a break, my cum settling back down so I wasn’t ready to shoot, and Cate settling down. During this time I rubbed her tits, loving them, enjoying them but really enjoying and into Cate. Cate now leaned forward and began to drive down on my dick again, and her tempo increased this time. Faster and faster she thrust my ever hardening dick inside of her wet cunt, a red flush color appearing first on her chest. As she continued to thrust rapidly that red flush color spread up into her neck and face, mainly her cheeks and suddenly Cate screamed very loudly “Oh fuck yeah, Oh fuck yeah! Oh YES!” and I felt her vagina quiver and then her whole body quiver as I at this time, no longer holding back, shot my cum into her nine times.
Cate collapsed on me and said “Keep fucking me” so I did. My dick was spent but still hard so I kept it up and brought her to a second vaginal orgasm. I looked at Cate as her pleasure was still erupting all over her body and I kissed her. I sought her tongue and suddenly I not only wanted to fuck her again, I wanted her. She responded and round two of our intercourse happen. This time we got worked up again in ten minutes and Cate got back on top of me saying “This is how we will fuck from now on!” I let her ride me, to have 100% control and I have to say, it was the best damn sex I have ever had with a woman. I brought her again to orgasm, Cate saying as she exploded and enjoyed the multiple waves of pleasure “Best fuck ever!” I exploded into her, though this time Cate rode me for a good forty-five minutes after foreplay and I shot my cum into her only about 5 times.
After this we laid in bed, holding each other. “Why?” I asked. “Wanted a test drive on a older model I guess” Cate replied smiling. “What do you think of older models?” I asked. “Well, not sure on any others and I won’t be taking any more test drives cause I have the one I want to drive.” came her reply. “What does that mean?” I asked. “Well, you like to fuck, I like to fuck, a lot. Your wife doesn’t, my husband doesn’t. I guess that means whenever we can arrange it, we are going to be fucking the hell out of each other, right?” Cate inquired/ordered as was her way. I thought about it quickly, though as long as we don’t get caught, and looking at Cate, I kissed her, and said “What the hell. I sure enjoyed the test drive and I think I want many more rides on the younger model!” I figured what the hell. She’s cute enough, driven enough, has a good mind, is educated and more importantly she knows how, is willing to learn what works for us, and is ready to fuck on a regular basis. Cate smiled to my reply and said let’s shoot for at least once a week, I would prefer twice. “Sounds great to me” I said. I then told Cate we didn’t use protection. “The only man I have fucked is my husband and you, soon that will probably be only you. You?” came her reply. “Just my wife like 4 months ago like I told you.” I said. “So no STD to worry about. Pregnancy?’ “Not from me, I had a vasectomy so we are good.” “Good, one kid is enough and neither of us want more kids, right, just more fucking?” Cate smiled again saying this. “Damn right” I said. “Just lots of fucking with you!”
Cate now said after about an hour after our second fuck, “I need to shower.” She got up and went to the master bedroom bathroom. I followed. She turned on the shower, waited for about 10 seconds for the water to get warm, and went in. I could tell by now she wanted it another time as I entered he shower, she grabbed me, hugging me and making out with me again, I sucked her tits and did so for a good five minutes and I felt her out during this time. As we kissed again, Cate turned around, leaned onto one of the bars in the shower, and grabbing my hard dick from behind said “We’ll end our fuck sessions like this every time!” and she then guided my dick into her cunt again. This time I was in control and I worked her vagina really good, ensuring that the slight curve of my dick stimulated her g-spot as I made love to her. Slowly I went, I like to enjoy fucking and taking my time to build my female partner up. Slowly Cate started to go faster and that is always my signal to match the woman I am with. Faster I went, faster Cate thrust back and forth on my dick, until suddenly I could not hold back and I shot my cum, then shot it again, and then shot it again and again into her wonderful pussy. Cate moaned as I did and I felt her erupt into her orgasms. After letting the water running down on us, and making out some more. we washed and dried off, kissing again and almost making love again but her son was due home from not just school, but his after school sports program in about 15 minutes.

I walked Cate downstairs, offered her the sugar and she said “I got the sugar I wanted.” Then we kissed, and Cate said I am off on Monday. I can work from home on Monday I told her. It meant prepping on Saturday but to have sex with Cate again, that was worth it. She grabbed my balls and dick with her hands, said “Now remember, these are mine.” Kissed me, winked and walked out of the house. It was good to know for the next several hours my cum would seep out of her cunt reminding her of our fucking. I really did think of the Fleetwood Mac song, Monday Morning you sure look fine as I went back to working.

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? Cate was off on Monday, she works in a different school district than her son, he was in school. So by 9:00am when he started, she was through my door, we were naked and touching, fingering, licking, kissing and fucking each other. Monday we basically made love from around 9:30am until 4:30pm, doing it four times, and once at the end in the shower as Cate expected. We experimented more with what makes each of us turn on and figured that out and the fucking was better that Monday than the other day. No condoms, Cate hates them as do I. On Thursday night, her son and husband went hunting for the weekend and my wife was out of town visiting her mother and father who are ailing, so Thursday night, Cate and I spent the night together, as we did on Friday and Saturday. We both agree it is like college again except we both like having only one partner. It’s improved our marriages since it takes the pressure off of our spouses to have sex, so no arguments. Now it’s Monday, she is working so am I and we plan to hook up Thursday night at her house as he son and husband will be gone hunting again. Friday will be during the day (wife is gone that Thursday on a business trip, coming home late Friday night so we have until 9:00pm to fuck, she gets back to the airport at 10:00pm) This Saturday will probably be no fucking.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Each have only had 1 partner in 20 years, I have a vasectomy so no pregnancy is possible so no condoms. Hate them anyway

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Find relief from a somewhat sexless marriage

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. If you talk, it gets out.

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? Finding a woman that loves having sex and loves it with me. Made me feel wanted, desired, and that having an affair can be an answer regardless of what others say IF after counseling your partner still doesn’t want to compromise.

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? Hasn’t changed my thoughts. I don’t want to fuck every woman I come across, nor every woman that is attracted to me. We have to both be attracted. Still like the notion of one sex partner, just this time it is someone other than my spouse and I am fine with that.

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? Best sex I have ever had. Love sex in middle age.

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? Old fashion. I like the notion of one partner but if one partner who I love in every other way can’t or won’t, I don’t see a problem with another sex partner. My wife doesn’t either as I told her I fucked another woman and she said “No disease, no whore, you’ll fuck me when I want it, IF I want it, first, and that can take the pressure off our marriage.”

What do you think about the Casual Sex Project? Interesting.

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