Insomniac Neighbor


This post is sponsored by Trust Massage Oil.


What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Customer Service Rep
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Insomniac Neighbor

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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? She was 6′, medium build, Asian. She had long hair dyed reddish-blond, with maybe DD breasts, and the night I met her, she was wearing a pink tank top that showed ample cleavage.
I met her through a mutual friend in the apartment complex where we were staying. The friend brought her over, and my two roommates left, for which I am grateful–the roommates suspected she and I were looking to have a good time, so they gave us our privacy.
Before the hookup, I thought she seemed a bit shy, and I wasn’t sure what would happen, but I was thrilled I could spend some time with a woman in my apartment alone at a time when I generally didn’t have a whole lot of privacy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had told the mutual friend who introduced us that I wanted casual sex only, so when she came over, she already understood my expectations, but I was respectful and patient in broaching the subject of sex.
We sat on the couch and talked, watching tv, and all the while I was sneaking looks at her cleavage and edging up closer to her. Finally I brought the subject around to if she had a boyfriend (she didn’t) and explained to her that I was looking for casual sex, that I didn’t want anything serious, but just wanted to have some fun. She said that was fine, but still seemed a bit withdrawn, until I suggested we just kiss to start with.
I was the instigator, and as for planning, I made sure to point out to her that if she had feelings for me, that she should call things off.

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? During the hookup, we started making out, pulling the curtain in the living room for privacy. She seemed to want to go a lot slower than me, but I wanted to get to my bedroom so we would be sure to not be walked-in on by my roommates, so I compromised–I said, “Let’s go to my room. I promise we won’t have sex, we’ll just play around. I don’t even have a condom. And if you feel uncomfortable with what we’re doing, you can leave at any time.”
At that, she nodded and smiled and seemed to relax a lot, and we walked back to my bedroom where we started making out more.
We undressed, slowly, and started gently sucking on her large nipples, going slow to try to please her. I went back up to kiss her, then started kissing her under her chin and on her neck, then under her ear, which she loved. I moved back down to her nipples, then kissed and licked her stomach, eager to get down to her pussy.
I asked her if she was wet, and she said she was, so I began fingering her a bit, slow at first, then faster. I used three fingers at one point, and she was getting in to it, but asked me to just use one finger (she was tight). After a good 10 plus minutes of this, she was very wet, and I kept going for some time. She moaned a bit, but still seemed to be holding back.
I went back to kissing her and playing with her nipples for awhile, and asked her to rub my cock. I am a bit on the small size, so she got all of me in her grip and gave me a handjob for awhile. She seemed to be enjoying herself, and was more relaxed, as was I, and we switched back and forth, pleasuring each other.
Finally, after at least an hour of this, I asked her if I could come on her. She said I could. She wasn’t able to bring me off with her hand, so I got some lotion and put it on myself, and straddled her chest while she laid back. Looking at her tits and her face from above her turned me on even more. I started calling her my ‘teacher’ and got myself close to orgasm, saying “permission to cum, teacher?” and she said “yes,” and then I told her to grab my hips so I could cum on her chest.
I was rocking back and forth for a few more minutes and said “here it comes, teacher,” and then I gave her my load. The first spurts of semen went on her neck and some got on the pillow, and the rest of the cum went on her breasts.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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 I came, she smiled and looked at me, and said, “You know you got some of your cum on the pillow.” Of course I didn’t care. Then I helped her clean up with a rag and brought her her clothes and after a little more talk and promises to do it again soon, I showed her out the door and she walked back to her apartment.
I felt great about it the next day–I had been looking for casual sex for a long time and was thrilled to finally have one. I hoped to continue it for as long as she was willing.
We met up three more times at my place and had similar experiences, but we never had penetrative sex. One time we did have ‘mammary intercourse,’ which for me was the best. So one other time I came on her chest and two times I came in some tissue after long, similar makeout sessions with her.
I feel thankful for her openness to doing what we did as long as we did. She finally broke it off when she had to go back to school in the fall and got busy studying. I wanted it to continue, but we both knew that our fling wasn’t serious.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, 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? I later talked to my roommate a little about it. He was congratulatory, and also wanted to hookup with her, but he didn’t, at least not to my knowledge.

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

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sexual experience. I was relatively inexperienced, still am, and this allowed me to see what I like at least in terms of non-penetrative sex. It was
I also loved that she let me cum on her chest. To this day, though there is nothing like having an orgasm inside a woman, a very close second for me is cumming on a woman’s chest or stomach.

What was the WORST thing about this hookup? That she didn’t have an orgasm–I always like to first help the woman finish first. That increases my own confidence and then makes my own orgasm that much better.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me more confident that casual sex is right for me.

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

All things considered, how NEGATIVE was this experience? Not at all 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? I am not interested in having a long term relationship–I love my solitude and cannot commit to any woman for the rest of my life. I am always looking for casual sex, though I am not one to hurt women’s feelings. I am always honest with women about wanting only casual sex, and I have found that most women who I broach the subject with are not interested–they want a relationship–but the last two women who I have proposed casual sex to have appreciated my honesty.

What do you think about the Casual Sex Project? I am very glad to have found this project. It has been fun to write about my experience, and I appreciate reading others’ experiences.

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