by Anonymous Mike
What’s your gender? Man
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? San Jose, USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Open, curious.
How many sexual partners have you had in your life (including oral sex)? 40 – 50? Maybe more.
How many hookup stories have you here posted before? 0
The ‘Boy’ Next Door
How long ago did this hookup happen? 2 years ago
What was your relationship status at the time? Engaged/Married (monogamous)
How would you best classify this hookup? One night stand + another moment of weakness.
How long did you know the person before this hookup? For less than a month
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? He was young, latino, tall (about 5’9 or so), extremely thin, but toned, medium length dark hair, naturally smooth/or shaved. He and his family moved into the house next door. I remember seeing them move stuff into the house from the moving truck. It was a hot day and he was shirtless and wearing a small pair of running shorts. I remember waving and saying hello to them and they greeted back. Jay, as I will call him, gave me a warm smile amd looks as he moved in and out of the house.
I’m a married man with kids, about 6 feet, try to stay in shape, (I’m not a body builder or anything, but i go the gym regularly) and am pretty happy with my cock size. (Im about 7 and pretty thick.) Definitely no complaints from the wife. She was out with the kids so I sat on the porch watching them move in over a few drinks. Before we ever hooked up, and in that moment, I found him very intriguing. It’s hard to explain, but I was feeling a strong attraction to him. His body’s slimness, those cute little abs. I’ve felt attracted to men before in my life but this was different. We met a few times as he was always running through the neighborhood, shirtless in running shorts. He was friendly and very intelligent. I would have drinks on the patio and see him there after a run, sweaty, shirtless, reading or lounging. He would always smile and wave, say hello. I spotted him once out on the porch in his underwear drying off. It was stramge but it turned me on.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He was on my mind a lot and he even entered my mind when i was masterbating a few times. I felt kind of weird after but I could tell where things were going. I was working from home and sitting on the patio in the early afternoon and i checked their patio for him. I heard laughing from their backyard and he (and a friend, who he later said was his cousin) emerged from their side fence. Both soaking wet and in swimsuits. Jay’swas a speedo type. It made me hard. Jay had a glass of wine in his hand and I thought that weird ssince he looked young and not 21. I called out to him and waved him over before I knew what i was doing. He came up to the fence and was giggling. He closed their back door and locked himself out and had to get their spare key. His parents were out running errands apprently. I asked if he wanted to earn some extra money over the weekend. He said definitely. I hadn’t done the yard work in the back for a while and said I’d pay him for his labor. He agreed and said he would be by the next day. He mowed the lawn and weeded the yard in his signature running shorts. My wife and sons were out and I watched from the kitchen window amd brought him some water when he was done. (We have a small back yard). He drank his water and i offered him something else. He asked for a glass of wine and i hesitated. He laughed and said it was fine and that he was going to run home to shower. I offered him a towl amd said he could shower here. He hesitated but said okay. I got him a glass of wine and we had some small talk. He was really into books and chatted about his current read. After he finished his wine i showed him to the shower. He washed up amd came out in a towel. I leant him a shirt and shorts from one of my sons. They were big on him but he made due. I had a glass of wine for each of us and he thanked me, brushing my hand as he took it. We sat on the sofa and I had the TV on. He put his cute feet up on the table and i notice he shaved his legs. I instigated by gently poking one. He laughed and said it was a rumner’s thing. I ran my hand up one and tested how far he would let me go. I got up to his thigh when he put his hand on mine. We locked eyes and i leaned in towards him moving my hand further up his leg.
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? It felt like forever, but we eventually kissed. Lightly. He said he hadn’t really done this that much before. I pulled him close to me and slowly kissed him more and he seemed to follow suit letting me french kiss him. He seemed a bit nervous but caught on quick and was good when he kissed back. I stopped and asked if it was okay and he shrugged. We went to our guest bedroom and he took off his shirt. He was about to take off the shorts when i stopped him. He looked confused amd asked if that was what I wanted. I told him I did amd took them off myself. For such a skinny kid he had a pretty big cock. He was semi hard. I dropped to my knees and i laid him on the bed and sucked him for a bit. He was tense at first but relaxed amd started breathing heavily amd let out a moan. I asked him to suck me and i undressed amd laid back. He stuttered at first but got the hang of it. I showed him a good motion for his hamd and it was amazing. He sucked until i got close amd we took a break and I told him I wamted to fuck him. He said he had only done it once and asked me to be careful. I agreed and slowly prepped him with my lubed fingers. It took a while but once he thought he was okay he said he was ready. I was so horny amd just wanted in him so bad. I put him on his back and put his legs on my shoulders aamd went slow unttil I was all the way in. I could tell it hurt at first but he didm’r stop me. I aasked if he was okay amd he just said to be careful. Once i was all the way im I could feel my cock pulsing inside him. I sstarted to fuck slowly harder. His moans told ke he liked it. He grabbed my ass at a few times pulling me in. He was tight as hell and I had to stop a few times to keep from cumming to soon. After a break i was fucking him missionary and he was moaning pretty loud. He gripped my hips quickly and shot an impressive load on his stomach and chest. Seeing it almost made me cum so I had to stop. I got a rag to clean up and we kissed some more and he was ready to go in no time. This time i guided him to sit on my cock and guided his hips to ride me. It felt so good i had to stop him multiple times to keep from cumming. I knew if I did, I’d be done for a while. He laid next to me and fiddled my cock. I sucked him off a bit and the way his body responded to it turmed me on. I turned him over amd pounded him. He moaned and said he was gonna cum! He did again. I took a breather trying to keep from coming and we cleaned the cover. Told him not to worry about it. I rubbed my hands on his body and he said he was having a good time and asked that I not tell anyone. I agreed, obviously and he asked if I can suck him again. I did for a few minutes and could’nt take it anymore. I asked him what he wanted and he said on his back with his legs on my shoulders. He said he liked that the best. His legs were super smooth and he had shaved pubes. It was super awesome. I had a hard time believing how much i was enjoying this. I asked if he could cum and he said yes just a bit more. I fucked him deep and slowly and he moaned amd arched his back amd shot another good load on his stomach as his hands grasped at mt hips. I pumped him so hard and shot my massive load inside him seconds. I pulled out and he cleaned up and said his paremts could be home soon. He said he would return my son’s clothes later when no one was around and asked me not to tell anyone please. He dressed and i watched him slip through the back door.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, 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? I felt great having had a positive sex experience and the orgasm was absoloutrly amazing. He was super tight and it was hard to control myself. I felt horrible a while later when I found out he was a student in my son’s math class. He was 16 at the time (age of consent) but i still felt a bit like a perv. My son came home and told me the neighbor boy was nice and was his partner for a math assignment. I almost had a heart attack. I was so conflicted, but looking back on it now it is one of the best sexualy experiences I’ve ever had. I still think about cumming inside him from time to time when I jerk off. He brought back my son’s clothes in just his shorts and I fucked him missionary on our kitchen counter until we both came. It was a moment of weakness and I could not resist. We did not hookup after that. I wanted to though and he certsinly flirted. We ended up moving. Not related to me having fucked him.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Talked about condoms. But we felt there was noting to worry about.
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Intoxication, To feel more confident, Power / Dominance, Intrigue and excitement from past experiences. It felt so nice to slowly teach and guide and eventually dominate and take control and feel him respond unfdsr me.
How intoxicated were you? A little tipsy/high
What substances did you consume? Alcohol
How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it
What substances did your partner(s) consume? Alcohol
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? Somewhat
Did your partner(s) consent to this hookup? They gave enthusiastic consent
To whom did you talk about the hookup? How did they react? A close friend of mine who I can trust to keep a secret. He was definitely shocked and warned me to be careful. He was curious what it was like and shared a similar hetsrosexuall situation.
How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)
Did you get emotionally hurt as a result of this hookup? A little bit
Did your partner get emotionally hurt as a result of this hookup? Not at all
Do you regret this hookup? Somewhat
Why do you regret this hookup? Had I known his age I would have not acted as I did. Yes, he was of legal consent age, but I would have had greater feeling of guilt for my actions amd attraction.
What was the BEST thing about this hookup? The SEX. How tight he was and the way he resonded to my touch and the way he moaned when i was able to really POUND him. I was able to get deep inside him and he let me know beforehand to guide him. Getting him to cum so many times (and two were without him touching himself). Plus, MY orgasm was out of this world.
What was the WORST thing about this hookup? Finding out his age from my son. Feeling guilty after giving in and enjoying fucking him again.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It has made me open up and realize how much men can please and attract me. Still not sure how to tell my wife though.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? A little negative
Anything else you want to add about this hookup? I’ve never had an orgasm like that before in my life.
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’d like to see not so much stigma and what people call ”slit shaming.’ If people want and enjoy sex then who are we to judge about how, with who, or how ofter they get/have it.
What do you think about the Casual Sex Project? I enjoy it and love reading through the stories. Nice to know you arent alone.
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