The Best



What’s your gender? Man
How old are you? 54
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? Engineer
What’s your current relationship status? Engaged/Married (monogamous)
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)? About 15
How many hookup stories have you here posted before? none

The Best

How long ago did this hookup happen? 20 years?

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

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? She worked at a factory for a company I worked for. I did projects and talked to the operators as the work progressed. She was from the Philippines, short, tan, older than me by a few years, though I don’t remember her exact age. The had a 20-something year old daughter, so she was probably mid-forties. She was toned from the constant workout that she got from the factory job, always needing to move boxes of product that weighed about 2 to 3 pounds. All day long. She was always initiating the conversations, but I think she appreciated that I would actually talk to her about assorted things. Seems she would always eventually make some flirty remark. My marriage was hell at the time, would end a few years later, so I appreciated the attention, though I had no intention of acting on it. That probably made it a welcome challenge for her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I don’t really recall the details, but she was planning a long vacation back to the Philippines, and needed someone to watch her dog. I wanted to help, I love dogs, so I was going to do it if the dog looked clean and well cared for. I went to he apartment one day, very close to work, with the only intention of finding out about the dog. While there she heated up some food, and we talked. She was drinking wine, I don’t drink, but she just looked at me and said something like, “I’m wondering if I should make your my lover.” That was all it took.

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? We started kissing, our clothes were off. I had never done this before, but I had the idea to turn her onto her back on the seat of the couch, with her legs up the back of the couch, so that her head was hanging over the edge. She was small, so she fit perfectly. I had my knees in front of the couch, and put my cock in her mouth. I slid all of the way in. It was the perfect height, and she really seemed to know what she was doing. I had one hand behind her head, just slowly withdrawing from her mouth and then pushing all of the way back in. She kept her lips tight around my cock as I drove in and out. My first time experience with deep throat, and she was an expert. No gag reflex at all. Each time I would reach the restriction at the back of her throat, the most amazing sensations would spread through my body. I don’t know what she was doing exactly, but it felt like she was actually making a swallowing motion when the tip of my cock would reach the back of her throat, and just pull me in deeply. I don’t know how long I lasted, but a few times I would leave my cock all the way in, just enjoying the incredible feeling, when I had a sudden realization that she couldn’t possibly be able to breath while my cock was in there, so I pulled it out, and realized that she was timing her breathing to match my thrusts. I tested her a few times, held my own breath while I was all the way in, and not once did she push me away to take a breath. It kinda freaked me out, thinking, hell, I could suffocate her. She seemed to not even notice, or she didn’t want to take away from the pleasure I was feeling, I don’t know for sure. I just remember feeling odd about that part of it. I would push deep, feeling her nose on my testicles, holding it there while she tightly massaged my cock with her lips at the base. Damn, this was pure pleasure. I was ready to cum, pushing harder and faster, until finally I was pulling her head towards me with my hand, while slamming my hips forward. I came so hard, I think it actually hurt a little. All the time I could feel her putting some suction on my cock. She had no option other than to swallow everything, and I stayed in deep for a while until my cock started to go soft, again, she didn’t try to push me away. I don’t really remember what happened after that, I think I took a shower and went home, don’t remember if we did anything else. By far the best oral sex I have ever received.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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 guilt, the first time I had sex with someone other than my wife, though my marriage was basically over, I still felt some remorse.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? I was feeling lonely, Just happened, I don’t know why, just went along with it, I didn’t want it but was unable to stop it

How intoxicated were you? Not at all (no alcohol or drugs)

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? Not at all

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 didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? No one

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? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? A little bit

Why do you regret this hookup? I was married.

What was the BEST thing about this hookup? I didn’t know women could do what she did. Never felt anything like it before. I have since had other girlfriends that could deep throat, but none with anywhere close to the talent this woman had.

What was the WORST thing about this hookup? Guilt from being married.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I think it is the source of me wondering since then, about every woman that I ever meet, can she do what this woman did? I find myself daydreaming, for a few seconds every time I meet any woman, thinking about this experience. I probably look like an absent-minded person to all of them until I snap out of it.

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? She and I began an affair that lasted several months after this. Turns out she was insatiable. Wanted sex all of the time. I was in very good shape, and our sessions always began with an incredible deep throat blow job, to completion. Every time, it was deep throat, vaginal, then anal sex. Usually she would be so excited that she would pass out at some point during the anal sex, which I didn’t realize until we had done it several times. She would come to from being passed out eventually, and it got to the point that I would watch her and wait for it. It seemed she was in a deep state of bliss. I would always have three orgasms, one orally, one vaginally, and one anally. I’ve never been able to repeat that with another woman. The most I could do was twice with other women, though I did have some incredible stamina back then. I think that it was just a feeling that she wanted me as much as I wanted to feel that feeling, so each of us was completely satisfied each time. Her body felt incredible. Her skin was soft and smooth, with incredible muscle-tone underneath. She was flexible, very bendy, and was willing to do whatever to make both of us feel as good as possible. Blowjobs on her knees as we showered together, we would eat lunch together sometimes, and once she ate a banana just like she would suck on me, making sure I was watching as it slowly slid all of the way in and back out. Brings a smile to my face now as I type this, remembering the look on her face as she played with my head by doing that, knowing we didn’t have time to do anything about it. She always made up for it later, never baiting me without following through. I moved away and never saw her again, but it was several months of just incredible sex, almost every day. She wanted me to stay overnight most times, but I never did. I don’t think I was ever in love with her, but I was definitely in lust with her.

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 don’t know about all of that, but I think she ruined me. Like I wrote earlier, every woman I meet since then, I look at her lips, and think about it. Always. Every woman. A few seconds of my life disappears. I get a slight twitch in my cock.

What do you think about the Casual Sex Project? It’s great to share the experiences, but I think at least one of the stories that I read is a lie, as it is the same 30 year old man from Malaysia, two different women in different countries, at an art museum, taking selfies. Why bother to write your experience, if you can’t be honest about it. If it’s just your fantasy, not your actual experience, you should say that at the beginning, better yet, don’t even write it, as my thought is that this is supposed to be actual experiences.

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