So I'm 32 (Jimmy), partner is 29 (Sam). We've been dating for 4 years. I'm from the city and she's from a small rural town that I hadn't even heard of until I met her.
She's always been pretty vanilla but recently got her telling me stories about her with other guys. Turns out she has slept with quite a few men (lots of one night stands) but not many real exciting times. Just drunk one night stands mainly.
Through more probing though, she opened up about this one guy (Mike) who she used to fuck on a regular basis. Mike is 11 years older than Sam. He was a guy from the same town who moved to the city but anytime he was home and she was single, they would hook up.
Sam goes on to tell me that Mike was the best she had ever had (she says before me but could be just protecting my feelings lol), he was the first to make her cum during sex and the fact that he was older was a big thrill. She says it's been a few years since they saw each other but she does creep his Facebook every so often.
So Mike becomes part of our bedroom talk over the last year. She tells me about the different times they hooked up, how great it was etc.
I've asked her a few times would she fuck him again if I said I was ok with it. She always said probably not because she wouldn't want to mess our relationship up. I asked what if you knew 100% that it wouldn't and she said she could be tempted but it's all hypothetical and she never sees him anymore anyway.
Fast forward to this Christmas. I agreed to spend Christmas with Sam and her family. On New Year's day they have a big party every year at a friend's house so Sam wants to do something on NYE but wants it to be low key so we're not hungover for the party.
Sam invites a couple of friends round to hangout in her parents basement (dad has a bar down there with pool table etc). Only a few people come round, it's pretty chill and then one of Sam's guy friends says "yo, Mikey is in town and looking something to do tonight, do you mind if I invite him round?"
I don't even make the connection. Sam looks at me for approval because of who it is but I just shrug and say, "It's not up to me." So Sam says sure.
Sam comes over and then says how she can't believe how cool I am with Mikey coming over and I asked who Mikey was...
"Mike...Mike I used to sleep with."
My stomach sinks a bit. I never thought I'd meet him. I became really jealous.
So he comes over and I act cool and shake his hand. I start getting drunk to kill my nerves and also to get through the embarrassment that I felt inside. I felt like a beta after spending a year asking Sam to talk to me about this guy in bed and now he was with us BUT I also had the voice in the back of my head that said this was the chance...I felt like I had to give it the opportunity to happen.
So a couple people leave and it's only 4 of us. I say I'm gonna go up to bed and leave the 3 of them to catch up. I walk over and give Sam the biggest kiss and looked her dead in the eye to try and let her know what I was thinking without saying it.
I go up to bed and lay wide awake. I hear the front door shut and look out the window, her friend had just left leaving just Mike and Sam in the basement (a regular spot where he used to fuck her while her parents slept upstairs).
I lay on the bed with my heart pounding. I didn't know what to think. About 20mins passed (felt longer) and she still hadn't come up. I couldn't handle it, I got up and crept downstairs to the kitchen where the door to the basement was. I couldn't hear talking. All I could hear was my heart pounding.
Then I start to hear a creaking noise. It's the old sofa they have in the basement that her dad refuses to throw out. I then hear her moan... Jesus it kicks in. I'm sat listening to my girlfriend get fucked.
I listen for a little while and then go back up to the bedroom as I don't want to get caught.
Some time passes and I hear him leave and then she comes up the stairs. She says nothing, just gets into bed beside me. She takes my hand and puts it down her panties.
His cum is dripping out of her.
"Is this what you wanted?"
I don't answer, I just roll on top, pull her panties to the side and slide right into her. I came right away, literally 3 thrusts... It was the best feeling in the world, I couldn't handle it but I felt so much shame at the same time.
I rolled off onto my back staring at the ceiling. Then Sam said something that I never ever expected...
My vanilla girlfriend told me to clean her pussy out.
"You said if this ever happened you would clean me, now do it. Keep your side of the bargain."
"Are you serious?"
"Yes, clean me." She took of her panties as she said this.
I never actually expected to ever do this, it was all dirty talk. But I did, I crawled down in between her legs and licked up all of mine and mike's cum from her pussy. She rubbed my head while I did it as if to say good boy.
Sam says it'll probably only happen with Mike again if we see him next Christmas again. I have never been so turned on and yet felt so much shame at the same time.