I [F]inally fucked [M]y bestfriend…

But he’s getting married next weekend. And I’m his best woman.

Warning I will sound like a totally needy and thirsty bitch. But bare with me.

We’ve been best friends ever since our first year of university. He’s not even my type physically. But we just understood each other and bonded so well. I never believed in soulmates but our friendship made me consider the possibility that he was mine.

Flashback to last year. When I found out that he was going to propose to another friend of our’s. I got jealous and desperate. I asked him over and we hung out. And I pulled out all the stops. Oversized shirt and panties a bit of make up and got my hair to look “messy”. We watched lotr and some hentai (we’ve done that before) and had drinks. It was to “celebrate” his soon proposal. I had other plans.

During the first scene in HHH Ecchi, the one where the guy discovers how horny the girl is, I started doing a bit of tempting. I tried to kiss him and he moved his head away so I put my head to his crotch to try and suck his cock. He said I was drunk and he didnt want to take advantage of me. I told him I wasnt drunk and I wanted him so bad. That made the conversation complicated. His relationship and future now even more tangled with mine. One thing lead to another and we ended up shouting. He told me with finality that he would need to distance himself from me for awhile. Then he left.

After a week of no contact we had a long conversation. We agreed that we were meant to be bestfriends. Like brother and sister. I told him I understood. Sort of. And agreed to be his best woman.

Cut to… his elaborate bachelor party last weekend. A whole day just for him. Planned out by myself and his entourage. Starting with football(soccer) in the morning to stall for time so the venue could make sure everything was perfect. I had a whole LARP’d D&D themed escape room setup to the theme of our long standing campaign (inspired by Criticalrole’s Matt and Marisha). I even had costumes setup.

Added note. At this point I’m seeing someone else. Another common friend and we’re doing great. He’s also part of the entourage and he paid for a good chunk of my insanity.

Back to bachelor party. We went through it and it was a blast! Though it was finished A LOT quicker than I thought. The whole thing culminated with a tavern style celebration. We had a long table setup with the works.

I was next to my new guy and we were having fun. Dancing, joking, drinking. By the end of the party, my new guy stayed behind for clean up like the gentleman that he is. And I helped make sure the groom got home alright.

Being very tipsy. I fuck up the destination point for the ride and we end up at my place. Too tired we decide its fine for us to just stay at my place. We thought. It wasnt anything new to us. So why not. We walked into my house joking, bonding, talking about our favorite fandoms and me proving two towers is superior to return of the king. During the banter I started taking off my earrings and my necklace which got caught at the back. He saw me struggling and helped. Once it was off and he handed it to me. Here was where I saw my shot and took it. I pulled him in for a kiss. Obviously I was also thinking I could play it off as “I’m tipsy!”(which I was!) if he got mad. But he didnt. And we started making out.

I MELTED. I scrambled to get my and his bottoms off. I wanted him so bad even when the tiny voice in the back of my head said “No! You talked about this! Remember, Brother/Sister!? He’s getting married!!” that voice vanished once I got his cock out and began trying to suck the life out of him. Hearing him moan for me got me more wet than my fingers ever could. I wanted him in me.

We eventually moved to my room where I pushed him on the bed. I remember ignoring him asking if I had condoms and saying I was on the pill before riding him. Finally having him in me I savored him as much as I could. I took every inch of him, full length, ass to balls. But I saw in his face and knew he was starting to feel guilty about what was happening so I did my best to make him cum.

Tiny as I am, I went into a squat position and moved up and down his cock as much as my small tipsy body would allow. I put his hands on my tits and asked him to call me names. I remember being all sweaty and grinding on him by the time he told me he was cumming… and when he finally did I selfishly kept going till I did too. And then some. Screaming how good of a fuck he was. I wanted to keep going but the little voice said stop. My body was also screaming for a break.

My thighs and calves were SORE after that. But my pussy was full. And we were partially naked on the bed next to each other. I remember turning away because I felt like he would be mad. He didnt say anything and slept on the couch. I didnt sleep at all.

Cut to the morning and we cant even look at each other. His wedding is soon. We knew what we did. We ended up having a horribly awkward conversation about him getting married; How I’m happily seeing one of his groomsmen. We spoke not looking at each other in the eye and standing social distancing style.

We came to the conclusion that changing any plans at this point would make people suspiscious. So our agreement, we take time off for a year. Our bestfriendship will be toned down even more now. And as much as I’m anxious, guilt ridden, and would just fucking love to be raptured or just straight elevatored to hell. I loved every moment of that night. He admitted he enjoyed it too.

I’ve begged the guy I’m dating to join us for the last leg of the planning just so I dont go insane. I cant tell him why, so I just told him I like having him around. Which isnt wrong!

Thanks for reading my long rant and admission of guilt. Now its time for this slut to go back to helping plan a wedding. Oh and this is joining that monthly contest!

Source: reddit.com/r/gonewildstories/comments/11k413c/i_finally_fucked_my_bestfriend

15 comments

  1. It was an itch you never got to scratch, and sometimes it becomes unbearable. As long as it stays just the one time, people make mistakes at bachelor and bachelorette parties. Maybe one day in the future once his newlywed days settle down, you guys may be able to arrange a couple swap to scratch that itch again.

  2. I hate the best friend one is attracted to trope.

    You are not best friends with someone you wish to sleep with. You are using friendship as a tool to assist you in reaching your goal of sex / a relationship.

  3. Your both scumbags but especially you. Doing all you can to confuse and attract him the moment he might be off the market? He is a shitbag for cheating on his fiance, you are a shit bag for manipulating your supposed best friend. As well as completely using your current partner you’ve already cheated on.
    I hope he tells his fiance and she leaves his pathetic ass, and he never speaks to you again you miserable grimy cunt.

  4. Right or wrong, how you choose to deal with it and move forward is the important part. We all fuck up. It’s part of being human. You two have set expectations, and it’s going to be trying at times, but it’s also going to show you exactly where your friendship stands.

  5. He probably was into you at one point and then was pushed into the friendzone. Being a good guy he accepted your decision and moved on. It’s amazing how we don’t realize what we’re looking for is right in front of us until it’s no longer an option.

  6. There is nothing hotter than finally getting that forbidden scratch out of the way. I had a similar fling with a friend of one of my best friends two months before getting married. Our chemistry was through the roof from the instant we met, and while I had a bit of post nut clarity awkwardness, we made love several more times. She cut me off completely after I got married but it’s still her I think about as my go to spank bank material.

    I hope the awkwardness between you two can subside after a while, and it’ll be good to have your bf nearby during the nuptials. The bf can be your sexual outlet and prevent him from consummating the relationship with a different woman on his wedding night

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