Amazing Hook Up With An Old Money Knockout



What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? Boston, MA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Recruiting
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
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)? 100ish
How many hookup stories have you here posted before? None

Amazing Hook Up With An Old Money Knockout

How long ago did this hookup happen? 5

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Friends-with-benefits

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? Lucy was 5’10 with dark brown-ish red hair (the red was artificial) and was porcelain skinned and often wore red lipstick. It was a great contrast.Extremely fit body with a great butt and breasts. She had a classic New England prep style and didn’t flaunt her amazing figure. She was a bombshell but was raised in a very old money family so was conservative in dress.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had met her at a Whole Foods after work and asked her about picking avocados. It was a cool day but she looked amazing in her navy cable knit Ralph Lauren sweater and white pants that showed off her phenomenal body. I made her laugh and used strong eye contact to let her know my sexual interest in her. I kissed her at the Whole Foods in the parking lot and I followed her back to her place under the intention of trying the new wine she had purchased.

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 made out on her sofa for several minutes after drinking the wine with a dinner. She was a great kisser and I was looking forward to seeing her long, toned legs without those white pants. She smelled great is what was driving me insane. She knelt between my legs and gave me a slow, sensual blowjob on the couch. I’m a bit over 8 inches but extremely thick and she kept commenting on how she wished she could take me further but was just sucking on the top quarter of my dick.

We went to her bedroom where I undressed her and ate her out for about 10 minutes while sucking on her soft, porcelain thighs. I gave her several hickeys to have her remember me by. She proceeded to give me more oral but this time I told her to use more spit and had her deep throat me (although the farthest she went was a little over half). This lasted along time and I enjoyed playing with her large breasts and gently fucking her mouth. I kept telling her to look up at me and make eye contact which she said after was very hot. I finally went inside her with her on her back and I held her by her ankles. She was just wearing her pearl necklace, matching earrings and nothing else which was a great sight. She was extremely tight (I later learned I was only the 5th guy she had been with sexually. We fucked like that for awhile and then later did it doggy style, reverse cowgirl, and I later put her up against the wall. This total process lasted about an hour. She felt phenomenal and at the end agreed to let me fuck her tight ass which I had been lusting over the whole time. She made me go extremely slow as well, after about 10 minutes it proved too much for her so I had her finish me with that amazing blow job which had her drooling all over me, it was even dripping down her chest. At the end of the blow job I pulled out and shot a huge load in her face. I was the first guy to ever do that to her I learned after.

How sexually satisfying was this hookup? Very

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? She cleaned up and we had sex again in the bathroom on the counter and I finished deep inside her that time and then left as I had to be up early the next day. I texted her once I got back and the texts were very raunchy. We later dated casually for a bit under a year but she is an old money white girl and as a black man myself we didn’t have as much in common to either of our liking. I later found someone more suited to me but Lucy has always been my favorite: styled like a cross between an old Hollywood siren with the style of a member of the Kennedy family as she was an Ivy League grad.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

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

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 told a lot of my close buddies, they all found her to be a knockout. I told my family after as we started going to dinner, they were a bit uneasy as she was an “Elite White Girl” and racial prejudices are sadly still an issue in America.

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Lucy was phenomenally tight, smelled amazing, had a knockout body…she was a true 10. I was shocked that a classy, Ivy League grad who looked like she did would engage in anal sex on our first hookup not knowing me.

What was the WORST thing about this hookup? I really have zero complaints. Penthouse Forum worthy material.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It taught me not to judge a book by its cover. Lucy presents herself as very much an Ice Queen. She dresses and carries herself like a Senator’s daughter and seemed like she would be a tease or a prude to most men. I learned not to judge people.

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

Anything else you want to add about this hookup? I didn’t think there would be much after this encounter. I thought she just wanted a hookup with an athletic African American guy. We ended up dating casually for awhile and I’m still friends with her on FB even after she is married now. I didn’t attend her wedding but she still likes any photo of me on FB and we chat a few times a year. I feel if she wasn’t married and I wasn’t with a partner now, we would still be hooking up all the time. The attraction is very strong between us despite the racial differences here in New England.

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 it’s a good thing, available to those who would like to indulge in it. I do wish that her family wasn’t in such a way that would have prevented us from being a full fledged couple. Her old money family would not have allowed that even though I come from a middle class background myself. If her family was different, we would have been together.

What do you think about the Casual Sex Project? I think it’s a great thing that you guys do. Some of the stories are crazy (in the best of ways)

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