Fling with the Neighbor



What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Chicago
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? 1

Fling with the neighbor

How long ago did this hookup happen? 3 years

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

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

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? Neve (named changed to protect the guilty) was just my type – dark hair, olive skin, fit, and had brown eyes that drew you in. Her eyes weren’t the “kind” brown eyes you read about. No, they were the “come fuck me” eyes. Anyway, Neve lived across the street with her husband and small child. They’d frequently come over to our house on weekend nights to drink and watch movies. Neve and I usually had a witty banter going on that neither my wife or her husband quite understood. I could tell by the way she started acting around me that she wanted to take it up a level. After a few times getting together, the sexual tension between us started to boil over.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One night we went together to get drinks in the kitchen while our significant others were watching a movie. As I was mixing a drink, she looked me in the eyes and grabbed my package. I had a feeling something like this would happen, but was still shocked. Without saying a word, I rubbed the front of her pussy through her yoga pants. She whispered in my ear that she wanted to fuck me right then and there. Obviously, that was a little difficult with our spouses in the other room. I told here we’d talk later and went into the other room. I think that she wasn’t used to being told no, as she gave me an evil look. Over the next two days, we arranged for a get together at a hotel.

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? Neve arrived at the hotel and, before I could close the door, immediately started to aggressively kiss me. I closed the door and repaid the favor. Immediately, all the sexual tension between us came out. I pinned her against the wall and started to finger her pussy while yanking down the top of her dress to start fondling her breasts. She pushed down my pants and boxers and started yanking away at my cock. In a fit of passion, I pinched one of her nipples hard. To my surprise she moaned and smiled. I knew then that she wanted a rough time. I stopped kissing her and pushed her head down to my cock. She immediately started to suck it…hard. I grabbed the back of her head and proceeded to throat fuck her. After a few minutes of devouring my cock, I threw her up on the bed, ripped off her panties, and proceeded to go down on her. Like I did with her, she grabbed my head and made sure her clit got a good session. After two orgasms from my tongue, she looked at me and said, “I want you to fuck me.” Who was I to argue? I reached over for a condom, but she stopped me. “No, I want to feel you,” she said. I had a vasectomy, so I wasn’t worried about a pregnancy, but was a little unsure. She was also on the pill, so I went for it. There’s only one other time in my life that sliding my cock into a wet pussy felt better (read about my time with my sister-in law). I was so hard. The fact that she was so aggressive, combined with the fact we were cheating and not using protection made this an existential experience. Needless to say, I didn’t last too long. I came deep inside her…something she seemed to really enjoy. We fucked a few more times over the next two hours and went back to our homes.

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 the hookup, we had a few more experiences. Unsurprisingly, she was into S&M and wanted me to dominate her during one of our hookups…including (according to her) her first time trying anal. That one left me a little worried as I left a few marks. But, I think she got off on trying to hide things from her husband. I ended up telling my wife, who didn’t seem to mind (we’re open / swingers). In fact, we went over to her house one day while and my wife decides to spontaneously go down on her. Marking her territory, perhaps? I wish we could have continued our sessions, but I started feeling guilty about hiding it from her husband. I encouraged her to tell him (they were also open), but she never did. We ended up moving to another state and the affair ended there.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Sterilization

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

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

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? 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? My wife. She was a little angry that I didn’t tell her before (she did know we were flirting) but was OK with it.

How would you best summarize people’s reactions about this hookup? Neutral

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? A little bit

Why do you regret this hookup? Her husband didn’t know.

What was the BEST thing about this hookup? Everything…the aggressiveness of Neve, her desire to be dominated, the unprotected sex (unusual for me)

What was the WORST thing about this hookup? Hiding it from her husband, not telling my wife before the hookup

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. Both my wife and I are open and generally don’t have an issue with causal sex. It did slightly change my perception of women and aggressiveness. They can be just as aggressive as men…maybe even more so.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

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 natural thing. As long as both parties consent, and precautions are taken to prevent STDs (don’t follow my example), what’s the problem? There’s too much stigma from society – particularly against women – with regards to causal sex.

What do you think about the Casual Sex Project? It’s great

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