by Art

Gender: Male
Age: 24
Race/ethnicity: Mixed
Current location: West Coast
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Student
Relationship status: Single
Religious affiliation: Catholic
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 35-40
How many hookup stories have you here posted before? None

Left Field Three Way

How long ago did this hookup happen? Little less than a year ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends w/ benefits/one-night stand

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? My partners were two girls. One was a good friend of mine who I met through school – let’s call her “Anna.” We had been very good friends for about a year and hung out on an almost daily basis, so I knew her well. Although I thought she was very pretty, we had never hooked up because I was always under the impression that our relationship was platonic. Anna is about 5’8, white with long blonde hair and a petite figure. I always thought she had a really nice ass too, but I never let her know it until we hooked up. The other girl – let’s call her “Beth,” – was just some girl I met out at the bar that night. I actually don’t even remember how we started talking, but we flirted for a bit and I brought her home. She was 21, so a couple years younger than me and Anna. She wasn’t overweight, but a little thicker than Anna. She was average height, white with long blonde hair, big beautiful blue eyes and huge, natural tits.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I guess you could say the hookup “began” before I even met Beth. Me and Anna – along with a couple of our friends – all went out with the intention of getting pretty drunk in order to relieve some of the stress from school. After a healthy pre-game, we went to the first bar where me and Anna were casually talking about me hooking up with girls. Although we were all together, it was just me and her talking while my other friends were in the midst of their own conversation. I was joking around about Anna being my wing(wo)man that night. Somehow this turned into a conversation about how she finds women “very beautiful,” but doesn’t consider herself to be a lesbian. Not very controversial. I suggested that if she feels that way she should try hooking up with another woman. After a couple drinks, I was real banged up so we all decided to make a move. We closed down the night at another bar, where I met Beth and brought her home.

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? So, my friends – including Anna – left the bar before I did because I was talking with Beth. Beth and I also decided to take our time walking home, grabbing some food on the way. When we got back to my apartment my friends were there smoking weed. Anna was in control, but you could tell she was drunk and a little high. Shortly after Beth and I sat on the couch, Anna came over and sat on my lap and started coming on to me super hard. She was whispering in my ear, telling me that she always found me attractive, so on and so forth. It was a bit awkward for everyone. First, although I thought she was attractive and very, very fuckable, I had put Anna in the friend category long ago. Before she sat on my lap I never thought her and I would ever, ever hook up. Second, the girl I brought home was like, “Uh…what the fuck? Who is this chick and why is she sitting ‘on my man’ (her words)?” Beth and Anna didn’t meet at the bar. Third, my friends were like, “Wow, this came out of left field.”

My friends eventually went to bed and as a way to diffuse this situation, I got up and said I was going to bed and went to go brush my teeth. While I was gone, Anna started making out with Beth and brought her into my room. I walk out of the bathroom to find Anna in her bra and thong mounting a clothed Beth while the two of them are kissing on my bed. While I’m standing in the doorway, Anna takes off Beth’s shirt, which reveals Beth’s huge tits in a sexy, red laced bra. The juxtaposition of petite, sophisticated Anna against that of curvy, big breasted Beth was too much to handle. So, I closed my door and sat behind Beth on the bed, worshipping her beautiful tits while she kissed Anna. We all got naked and I started fingering Beth doggy-style while she ate Anna out. Then, they both sucked my dick and rubbed my balls. Anna then got on top of me while I put my cock as deep inside of her as her pussy allowed. It was pretty hot. I switched up the positions, fucking both Anna and Beth, but in hindsight realize most of my attention was spent on Anna. I didn’t realize how much sexual tension existed between me and Anna until she was faced down in my pillow, screaming while I fucked and pulled her hair. Really, once our clothes came off I could not keep my hands off of Anna. Although I paid a fair amount of attention to Beth too, I repeatedly interrupted switching positions in order to eat Anna’s pussy while her and Beth played with each other.

Did you have an orgasm? Did your partner(s)? I came when I was fucking Beth, actually. Anna definitely had an orgasm and probably woke up the entire God damned house while doing it. Beth, not so much.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Nothing. I get tested, so I knew I didn’t have anything and I am confident Anna didn’t either, but we never discussed it. Beth was the wild card, but we didn’t discuss it with her either. It was a very fluid situation.

What were your REASONS for having this hookup? Along with the fact that I was drunk and horny, I also remember thinking to myself that what was occurring before me was rare. Most guys go through life without ever having the opportunity for a threesome, let alone having one dropped in their lap. So, I just went for it.

Were alcohol or drugs involved? If so, how much? Definitely. I was hammered (probably why I was able to last so long in such a sexually hot situation) and high. Anna and I had also taken a little Adderall before going out, but not much. Beth was just drinking.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Despite the fact that the sex was terrific, after the hookup was not so great. After we finished, Anna, Beth and I were talking to each other and Anna looked very pleased and content. More so than I had ever seen her, actually. She explained to me that she had always found me to be very attractive and was surprised that I was unaware of her feelings. I wasn’t completely unaware of it, but again, I just assumed her and I were going to be friends and leave it at that. The next morning she walked home and I drove Beth home. Shortly after that night, though, Anna got super weird about it all. She’s ashamed at the way she acted in front of our friends, even though I told her it was fine, we were just having fun and no one holds it against her. Didn’t help. Things are still weird. We’re actually not really even friends anymore because of it. I never talked to Beth again after driving her home that morning. I occasionally see her out. One time she was staring at me from across the bar and I nodded hello to her, but was uninterested in starting up a conversation. Better to leave on a high note.

To whom did you talk about the hookup? How did they react? I’ve told most of my boys and they all think it’s the coolest story ever. I’ve only told people who do not go to our school and are not mutual friends with Anna, however, as I know she’s still embarrassed about it all and doesn’t want a ton of people knowing. But, I’m not from where I go to school, so most of my friends will never have any idea who Anna is, let alone meet her. She also doesn’t use social media, so she’s pretty much off the grid.

Was this a consensual and/or wanted experience for you? For your partner? At first, Beth and I weren’t really into it but we were eventually persuaded otherwise.

Do you regret this hookup? If so, why? Not at all. Maybe I should because Anna was a good friend of mine, and I still love her because she’s a sweet person. It’s a shame we haven’t been friends for quite some time and that things are awkward. I tried a number of times to make things normal again, but gave up after a couple weeks. I’m not a therapist and am not interested in becoming one, so I backed off and our friendship has since withered. That kind of stuff happens naturally anyway as time progresses. Relationships are always beginning and ending. At least this one ended because of an awesome sexual experience (for all parties) that I’ll never forget.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about this hookup was the fact that I got to have sex with two beautiful women at once. The worst thing was Anna’s subsequent reaction. It hasn’t changed the way I think about casual sex, really. I’m still open to one night stands, as was the case with Beth. And I’ve always had a kind of unwritten rule not to hook up with friends, as was the case with Anna. I had a lapse of judgment that night, but I don’t regret it. Going forward, I’ll still try my best to stick to the same rule. No promises though.

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

All things considered, how NEGATIVE was this experience? A little negative

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