This happened years ago when I lived outside Chicago. I was kinda/sorta dating this girl Kaitlyn. We started out just hooking up, and then after a few weeks (I was seeing other people throughout this) she asked where we were going and I told her I wasn’t looking for a relationship, just a hookup, and I had other hookups and I was ok if she did.
She didn’t take this super well, and ended up immediately hooking up with friend of mine, which tbh didn’t bother me because…reasons stated above. We joked about it together. Anyway, you just have to know for the story that she wanted to annoy me by flagrantly hooking up with other people and putting it in my face to make me jealous, but it wasn’t working because I didn’t want an exclusive relationship with anyone at that time of life.
So one weekend I’m traveling for work, I’m a videographer, and I invited her along to stay at a fancy-ish place I was being put up in Minneapolis for a two day job as a travel fuck-buddy.
So first night we go out for thai food at an upmarket place and Kaitlyn makes a big show of flirting with the waiter, a tall college aged kid, and even goes so far as to touch him when asking about the menu. As we’re on our way out she goes over to him and slips him what I assume was her number. It was a turn on, tbh, and when we went back to the hotel we had some rough, aggressive sex.
Next night I had to work until about 8 on the job and texted her when I was wrapping up to see if she wanted to come out for dinner, come for drinks with the crew, whatever. She texted me back “pick up some takeout, and get extra, I’m really hungry tonight”. I swung by an indian spot and got an assortment of curry etc, extra naan, tandoori. Minneapolis isn’t that big of a city, so half an hour later I’m putting the key card into the lock.
I walk in to see Kaitlyn with her rotund ass sticking up in the air, her shaved pussy glistening with wetness, on hands and knees and bobbing her head up and down vigorously on the waiter from the night before. When he sees me walk in he looks alarmed and tries to get off the bed but she puts her arms on his legs and pins him down and starts gagging loudly while deepthroating him.
I put the food on the counter and take off my jacket, then walk over to the bed and gently start caressing Kaitlyn’s pussy, using her wetness and massaging her clit in the way I know she loves. She starts to lose focus on the waiter as her body convulses in a powerful, throbbing orgasm. When she finally comes down she looks back at me, angrily, and puts her mouth on the head of the waiter’s girthy cock while holding eye contact with me.
I disrobe at this point and get behind her on the bed and start eating her out from behind while she continues her work. I can tell I’m hitting the good spots when she can’t keep sucking the waiters dick, and after a particularly intense orgasm I start flicking my tongue on her asshole, before pulling back and getting into position to thrust into her.
She pulls away and ignores me, putting her body forward and mounting the waiter, holding his cock, wet with saliva, and guiding it into her dripping pussy, lowering herself down in one slow movement and letting out a continuous sigh. She starts riding him, slowly at first and then gets into a regular grind. I’m throbbing so hard it hurts and I can’t wait to fuck her, but she’s ignoring me, although she makes no effort to stop me when I grab a tit and a handful of her hair and start helping her move in rhythm, the waiters cock sliding loudly in and out of her pussy.
After a few minutes she leans towards me and I kiss her roughly on the mouth, biting her lip as I come up, then rising onto the bed I grab her by the back of the head and force her mouth down deep onto my throbbing member. She gags a bit and then immediately comes hard, the waiter rubbing her clit and bucking his hips into her in time with her movements. Her grunting moans with my cock down her throat drive me completely over the edge and I came with intense spurts down her throat, causing her to choke a bit and almost spit up when I finally let her take her head off my still erect cock.
I collapse onto the chair and breathe heavily as the two of them slow down. Kaitlyn is staring straight at me as she climbs off the waiter and gets on all fours facing me while he gets behind her and thrusts roughly into her. Grabbing her by the hips he pounds her relentlessly, putting a leg up over her, grabbing her hair, putting two fingers in her mouth and making her suck on them while he holds her head back and thrusts, hard, again and again into her pussy. After she’s taken almost as much as she can handle, her face buried in the pillow and grunting loudly at each thrust (I think she’s putting on a bit of a show at this point), he immediately pulls out and uses both hands to finger her fiercely, one hand with three fingers in her snatch, the other rubbing two fingers hard on her clit, then just as she climaxes he pulls his fingers out roughly and stops touching her at all, and she collapses shaking onto the bed, liquid bursting in pulses out between her legs as squirts all over the bed we shared the night before.
I am by now fully hard again and pumping my dick a bit in the chair watching this young stud fuck my friend. She calms down a bit, then the waiter flips her on her back at the edge of the bed and holds both legs up while he fucks her steadily and hard until she’s moaning again, then tells her “I’m gonna cum on you” before pulling out and spurting loads of thick cum across her body and up to her face, some getting in her hair but most on her body as she holds her tits together and smiles.
As soon as he pulls away I go immediately over and thrust into her pussy, her eyes closed she makes no effort to stop me, and I pound her as hard as I can for only a few minutes before I pull out and do the same, my cum not quite as thick on the second orgasm in a half hour, but covering her tits and stomach.
The waiter grabs her and pulls her around again, dangling her head at the edge of the bed, and she’s lost in the moment as he thrusts into her throat while rubbing her clit again. After thrusting deeply for a few minutes and rubbing her off to another moaning orgasm he pulls out of her mouth and puts his balls onto her lips and jerks off furiously until he pulls back a bit and drips another load of thick semen onto her face, slack and bewildered from so much cock.
The waiter said thanks and then awkwardly got dressed and left, politely declining to stay for curry.
Kaitlyn sat, cum-drenched, and ate curry at the edge of the bed, making deliberate small talk and not addressing her condition, even as cum dripped from her face to her chest. We showered and fucked again that night before flying back to Chicago in the morning.
Kaitlyn and I kinda drifted apart after that, she definitely wanted more of a relationship and I think she felt ashamed at her hookups when she was trying to make me feel jealous, but in any case it didn’t continue long between us.
Still one of the hottest nights of my life though.
Source: reddit.com/r/sexystories/comments/otv8hs/fwb_invites_a_third