Best Lay of My Life



What’s your gender? Man
How old are you? 29
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? Indianapolis
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? In a serious relationship (open)
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)? 40+
How many hookup stories have you here posted before? 0

Best Lay of My Life

How long ago did this hookup happen? 5 weeks

What was your relationship status at the time? In a relationship (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? She was about 5′ 2″, 120 lbs, and medium-brown skinned complection. I met her through an online dating site. I thought she was cute and had a perfect body. I got the sense before we met that she was outgoing, open, adventurous, and possibly into hooking up and casual sex. After a few dates, however, I got a sense of bi-polar narcissism. She had a terrible attitude at times, then pleasant at other times. I thought, as from previous experiences, she must be dynamite in bed–as the crazy ones usually are.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I am in an open relationship with an amazing woman, so I was looking for a new friend with benefits. After a few dates, I determined where I wanted to go with this woman. That is, a few hookups and that’s it, hopefully. I couldn’t deal with her emotional roller coaster of a personality more than that. I felt like it was way past time to seduce her and break her off in my usual way, but I couldn’t bring her back to my place because that would violate the agreement of the aforementioned open relationship. Her place didn’t make me feel comfortable, either. So the day before New Year’s Eve, I texted her about getting a room, and she said yes without hesitation. I planned a romantic evening that was sure to get her pussy wet and in the mood, just to be sure. I like having my lovers completely turned on in every way. I love the feeling of just blowing their minds sexually, and tonight was no exception. However, her attitude almost ruined the night from the start. By the time we got done with all the planned activities and to the hotel room, I was fearful the night was a waste. That is, until she said she’d like to take a bath. I knew what that meant.

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? If her intention was to get me mad and have passionate, intense, and angry sex, then she definitely succeeded. The whole time she was giving me attitude throughout the date, I thought to myself about how satisfying it would be to just ravage her pussy that night. So when we got to the hotel room and she invited me to the bathtub, her fate was sealed. Not to toot my own horn (if I haven’t enough already), but her face was priceless when she saw the size of my erection. I climbed in the bathtub behind her and started giving her a back rub. I intentionally slowly moved to her nipples and then to her clit. She came twice very easily. “This is going to be fun”, I thought to myself, because never had it been that easy to get a woman to orgasm. I wanted her pussy to be as wet as it could possibly be, so when she rose up to sit on my dick, I grabbed her by the waist and pulled her pussy up to my lips. Her pussy tasted amazing, and I couldn’t get enough. So she wasn’t ready for the tongue lashing she received. With her legs quivering, she positioned herself to ride me (surfboard) and I slid into her. I was surprised that she wanted to go raw, and her pussy felt great, so it was a struggle not to come too soon. She came a few more times, then turned around and rode me till she came again. We got up out the bathtub and went to the bed. It was finally time for me to let out some frustration, so I changed the pace from slow and sensual to hard and passionate. I’m an athletic and strong guy, and she’s small with an athletic build too, so to say we fucked each other like pornstars is an understatement. I fucked her doggystyle on the bed until she sank into the covers, then flipped her over to do a standing missionary. I pulled it out with her legs still shaking to suck on her clit again. We went at it from there to the ottoman, then back to the bed. Licking, sucking, and fucking until she screamed “yes daddy!”, “aye pappi!”, “I love you!”. She jumped up and walked towards the front of the suite, exclaiming “Oh my god, what are you doing to me!” I chased her down, put her on the couch and started eating her out again. We fucked on the couch, and then back to the bed. We did 69 and she sucked me just right until I almost came. Then she got on top and rode me reverse cowgirl until I finally shouted, “I’m about to come!” She came once more and jumped up just in time to avoid the nut. The sex was perfect.

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 hoped we would continue hooking up–at least a few times. However, things don’t always go the way you want them to. Not to mention, her attitude got in the way. But, since we will be working near each other soon, I would imagine a scenario where something can happen again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more, Making new friends, Boredom

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

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? A couple of my closest friends.

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? It was the best sex I had ever had with anyone, and the perfect ending to the night.

What was the WORST thing about this hookup? It only happened once.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Somewhat.

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? I knew I was good, and I figured that she would be decent, but I don’t think either of us anticipated it would be THAT good.

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 think that it is an amazing part of the human experience. I love that I have been able to bond with so many women on a sexual level. To share this kind of intimacy is the best part of life.

What do you think about the Casual Sex Project? It’s great! I can’t wait to share more stories, since this is my first one. I feel like I finally have an outlet!

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