What’s your gender? Woman
How old are you? 40
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Analyst
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Buddhist
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)? 30 to 40
How many hookup stories have you here posted before? 1

Three Brothers

How long ago did this hookup happen? 15

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Group sex

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? We were all attending the same university. I was in graduate school. There are three brothers. The oldest was a senior, the middle one was junior and the youngest was just a freshman. All three brothers are very good looking in their own ways. Their good look could easily make them movie stars. Almost all females in the social circle all had the hots for the three brothers. I casually dated the middle one. While the middle one is the tallest of the three, he is the most quite and introvert one. I think it may have to do with his much smaller than average cock.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Drinking & chatting to pass time is very common in their culture and the three brothers do that almost every weekend among themselves. One night, the three brothers were drinking among themselves. The middle one asked me to go to their house to join them and I obliged. After some drinking with them, I was a little buzzed and quite horny because I was drinking with three hot looking brothers, who all seemed quite flirty with me. At that time, I thought it was because I was the only female there. In the hindsight, I suspect it was because of their premeditated plan.

Anyway, after I was visibly buzzed, the middle one took me into his room and we had sex. Since he has smaller than average cock and he couldn’t make it up with good technique & stamina, he left me craving for more. After sex, he left the room to drink some more with his brothers.

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? Since I was already buzzed, I decided to just lie in bed & rest. After about 5 minutes, I heard someone entered the dark room but I just assumed it was the middle brother and I didn’t even bother to open my eyes to look.

I felt the guy gently got on the bed, nudged & flipped me over to face down, parted my legs and probed my still wet pussy with his fingers. After fingering my pussy for a minute or two, I felt him straddle me and entered me from behind. As soon as I felt the cock pushing into my pussy, I knew it wasn’t the middle brother because the cock felt much larger. I turned my upper body & looked. It was the oldest brother looking at me smiling, as he started to slowly penetrate me. I didn’t object and I just laid back face down and enjoyed the feeling of his cocking pumping me from behind.

After only a few minutes, the oldest brother pulled out, ripped off the condom, and unloaded his cum on my butt crack and just outside my pussy. He left the room. While it felt good to have a larger cock filling me up, I still didn’t reach an orgasm. So, I continued to lie on my tummy but I reached down between my legs and finger my on clit in hope of getting myself an orgasm.

Less than a minute later, I heard the door opened again. This time, I quickly turned & look. I saw the youngest brother coming into the room. He paused & hesitated when he noticed that I was looking at him. It looked like he was debating whether to turn around & get out of the room. I was really horny & I was ready to fuck all three handsome brothers, and I didn’t want him to leave. So, I quickly smiled and joking said, “So, the youngest get to take the sloppy 3rd???”

He laughed, quickly stripped naked, jumped on the bed, & got between my legs. When he saw the cum on my pussy & ass crack, he took a piece of clothing nearby & tried to wipe as much of it off as possible. Then, he hastily got between my legs and inserted his hard cock inside me. He didn’t even try to pace himself and just pumped hard & fast. I reached down and massaged my own clit while he pumped away.

The thrill of fucking 3 very good looking brothers one after another really got me going and I finally got my first strong orgasm of the night as the youngest brother pounded away on my pussy. Soon the youngest brother followed with his own ejaculation right inside me. When his cum started to drip out, that’s when I realized that he didn’t even wear a condom. I was a bit worried for a moment because I wasn’t on birth control.

The youngest brother left the room. As I laid there savoring my orgasm, the oldest brother came into the room again. I looked at him just smiling and admiring his chiseled face while he took off his shorts. He got on the bed without saying a word and fucked me again in plain missionary. I wrapped my legs around his waist and really enjoyed his cock sliding in & out of me until another orgasm hit me. The oldest brother didn’t even slow down and just kept fucking me in the same mish position until he cum inside me.

When the oldest left the room, he didn’t even bother to close the room door. But I didn’t care because I was quite exhausted from 2 orgasms and the alcohol. I was half drifting into sleep when I felt another guy crawl on top of me and it was the middle brother. I was quite tired and I didn’t really bother to respond or interact. I just lied there and let the middle brother fucked me while I was half asleep.

For the next few hours, those brothers took tuns coming into the room and fuck me while I lied there drifting in & out of sleep. Sometimes, I reflexively responded to their thrusts. Most times, I just lied still & semi enjoyed the pleasure of being pounded hard. I don’t remember exactly how many times. I would say each of the three brothers probably come into the room 3 to 4 times to fuck me, like a blowup doll, over a span of few hours. They didn’t care much whether I get pleasure out of it. They just spread my legs, pounded me until they cum.

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? After the three brothers had several rounds with me, it was wee hours in the morning. The middle one came to sleep next to me until almost noon. I woke up first and took a shower. As I was leaving their house, I found the youngest one passed out on the couch and the oldest sleeping in a bedroom. The middle one and I continue to see each other once in a while but never talked about that night.

A couple of months later, the three brothers again invited me to join them for drinking & chatting. The 2nd time around, I knew what they wanted. I drank with them for a while. This time, the oldest brother asked me to go to the room first & we fucked quickly. I put on only a T shirt and I went out to drink some more with the 3 brothers. Then, the middle one took me to the room and we fucked. I again went back out to the living room to drink a bit more with the three. Then, the youngest brother took me to the room to fuck.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, Condoms, Birth control pill / patch / ring / injection / implant

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

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? I told my BFF at the time about the hookup. She was quite envious that I fucked all three brothers. She kept asking me to tell her all the juicy details.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I slept with all three very handsome brothers on the same night.

What was the WORST thing about this hookup? I was too tired to enjoy every round of fucking.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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? No change

What do you think about the Casual Sex Project? Excellent!!!

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