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Lost a Bet
23/12/2023
Growing up my best friend and I shared information about everything. From masturbation to girlfriend sex. My buddy had a bigger dick than me and loved to brag about it.

He would always say he could steal my girlfriend if she saw how big his cock was. One afternoon when we were drunk while fishing.

He bet me he could fuck my girlfriend. Of course I bet him I could fuck his. So the challenge was on. We were on a camping trip with my buddy and his girlfriend when the bet was made.

The rules were that neither one of us could interfere or stop the other if we were fucking the others girl. My girlfriend was a bit of a prude so I felt my chances of winning were good.

The camp ground we were staying at had a public bathhouse. That afternoon my girlfriend and I said we were going to go take a shower.

My buddy Mark said he would join us, giving me a smile. The shower area had several shower rooms with small changing areas connected to each one. Men and women could use them.

Me and my girl shared a shower while my buddy used the one next to us. I tried to fuck my girlfriend in the shower but she was afraid my buddy would hear us so she ended up jerking me off instead.

When we were done we exited the shower room and my buddy exited right behind us. He had a towel wrapped around himself. He made a comment about not bringing a pair of shorts and pretended to be adjusting his towel.

The towel then fell open exposing his semi hard dick. Obviously he had been stroking it in the shower. It was impressive I must say. The look on my girlfriends face was of amazement.

As we walked back to our campsite, she whispered to me, oh my god, did you see how big his dick is. I played it off like it wasn’t really that big. Later as we were going to bed , i tried to get pussy again.

She shut me down again, but brought up my buddies dick size again. I shut the conversation down saying I was sleepy and went to sleep. The next day my buddy jokingly asked if my girl asked about his big dick. I told him no.

The day was beautiful and we swam and fished all day. The girls cooked up a great dinner and we sat around the camp fire later drinking. I announced I needed a shower and asked my girlfriend to come.

She said she was good and go ahead. So I headed out by myself. When I returned there was only his girlfriend at the campsite. I asked were the other two were and she responded that they walked down to the docks to check on the boat.

I thought o.k., this is my chance to hit on his girlfriend. I sat next to her and we talked about trivial stuff. Then I got the courage to make my move. I told her I find her very attractive and thought about her often.

She blushed and smiled, saying she was flattered. She then said that she was very happy with her boyfriend and would never cheat on him. I felt completely shut down.

Meanwhile time passed with our two partners still not returning. I told her I was worried and would go look for them. She said she would stay in case they return. I hurried down the trail towards the docks.

As I got closer I could see the docks and boats because of the lightning. I didn’t see anyone so I stopped in the shadows and began looking around. Towards the far end of the park was a covered picnic table.

It looked as if someone was under it. I slowly approached to see who it was. I began hearing loud moans and they sounded familiar. I snuck closer staying in the shadows. I got within fifty feet and I could see my girlfriend sitting on the table with my buddy standing between her legs as the were kissing and fucking.

I could hear there orgasms and then my girlfriend says we need to get back before they get suspicious. I quickly returned to the campsite saying I couldn’t find them.

They arrived shortly behind me and my girlfriend looked awful guilty. They both gave an excuse about getting lost on the trail. Then my buddy gave me a side eye wink. When we were away from the girls, he began bragging about smashing my girls pussy. I admitted defeat.

Though it didn’t stop there. They were sneaking off to fuck every chance they could after that night. I never got any pussy all weekend and was pissed at my buddy. Though I couldn’t do anything about it.

His girlfriend started getting suspicious of them and mentioned it to me but again, I couldn’t say anything and blew it off. A few weeks later they broke up and a few days after that my girlfriend dumped me for my buddy.

Not only did he win the bet but, he stole my girl as well. They didn’t date long before they broke up. We were still best friends. Years later, we were both married and my buddy was gloating about stealing my girls pussy when we were out drinking.

I stupidly told him it could never happen again. He said, oh yeah, want to bet. I was hesitant but in my drunken stupor made the bet. The next day I realized my stupid mistake and decided to sabotage the bet. I told my wife about our drunken bet hopping she would be disgusted and mad about it.

She asked why we would make such a bet. She asked if I thought she would cheat on me and why. Not thinking, I told her he has a big cock and is always bragging about how he can get any girl.

So I bet him knowing you would never cheat on me. She looked at me and then asked, how big is he. That’s when I realized I fucked up. I down played it but could tell she was inquisitive now.

The subject was dropped and several months later my buddy calls and asked if I could meet up for a beer. We met at our regular drinking hole. He then asked how everything was going at home.

I told him great, why. He smiled and said just asking. He then said, oh by the way. Let me show you something. He pulled out his phone and began showing me a video. Right away I recognized my bedroom and then my wife’s tits.

She was riding my buddies cock in our bed. He said, looks like I won again. I asked him how many times has he fucked her. He replied enough that your small dick will notice.

Here I am again knowing my wife is fucking my buddy and I can’t do anything to stop it. I guess they’ll eventually get tired and move on, I hope.


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