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Lost a Bet
12/03/2024
When I was in High School, me and my girlfriend would double date with my best friend and his girl. Both of our girls were pretty hot.

Mine was tall and thin with perfect tits. Marks girl was shorter but a hard body with nice tits. My girl Jan had long brunette hair and was girly and Marks girl Jodi had short blonde hair and was athletic.

Both our girls loved fucking and we did a lot of it. One night we were all hanging out drinking and smoking a little when Mark started bragging about how good his girl sucks dick.

Of course I also said the same about mine and we began talking about fucking them as well. The girls were out of ear shot when all the bragging was taking place. Mark told me he thought my girl was hot and would love to fuck her.

I said his was also. He then said, we should swap. I laughed and said no, I don’t think Jan would go for it. I really didn’t want him fucking Jan. His dick was bigger than mine and I was insecure about my own.

He then said I bet she would fuck him. I said she’s not like that. He then proposed a bet. His bet was that he could fuck my girlfriend and I wouldn’t be able to fuck his. We couldn’t tell them about the bet or do anything to sabotage the other.

I turned it down but he started calling scared so I bucked up. I jokingly said, what if she (Jodi) wants me more than you. He said if the girls want to continue fucking then the loser has to be the bitch. I laughed and said you’re on. I thought my odds were good because I was taller, better looking, and in great shape. The bet was to start the following day.

A couple days later I saw Jodi at school and I began talking to her. She seemed a little flirty during our conversation so I asked if she minded if I called her. She said sure and gave me her number.

That night I called and we made small talk. I told her I found her attractive and she said she thought the same of me. I then said if her and Mark ever broke up would she go out with me.

She said she would. The next day when I was walking towards Jan’s locker, I saw her and Mark talking. I stopped and watched. They seemed to be flirting and I noticed Jan touching him often.

She noticed me and broke it off and he walked past me and winked. I asked what that was about and she said nothing. That night I called Jodi again. This time I asked her if she would like to meet somewhere.

She asked why. I said we could hook up if you would like. She then said NO. I’m not going to fuck you behind your best friends back, you’re sick. And stop calling or I’ll tell him what you did.

At this point I knew it wasn’t happening. About a week later I was suppose to work Saturday but decided to call in sick because my girls parents were out of town. I drove out to my girls house and when I arrived saw my buddies Jeep in the driveway. I drove past and parked.

I snuck back to her house and tried to peek inside. I could hear loud music and that worried me. Especially when it was Steely Dan playing. That was her favorite fuck music when we had sex. I couldn’t see anything so I crept to the back of the house where her room was.

Her lights were out and I stood near her window trying to see inside. Then I heard the familiar sounds of my girl having an orgasm. I was crushed and furious at my buddy. Then I realized I was getting a major boner listening to her cry’s.

As I stood listening to them having sex, my hornyness made me do something I wasn’t proud of. I removed my hard dick and masturbated while I listened. I couldn’t believe he was able to fuck her so easily. I eventually returned to my car after I cam and waited.

Two more hours pass before I hear his Jeep start as he pulled out her driveway. I began following him as he drove home. When he pulled into his house, I pulled in behind him. He said, hey look, it’s the bitch. I said what the fuck dude.

He said that’s right, I fucked your girl, and she was tight. I was angry and said, prove it. He then pulled out a pair of her panties and I recognized them. He asked if I wanted to sniff them. I said, hell no.

He jokingly said it might be the last time you can smell her laughing. I left and went home. The following week at school Jan was stand offish. Our conversations were getting shorter and she started dropping hints that she needed space. I couldn’t believe she was going to break it off because of one fuck.

I called my buddy and asked him to tell me everything. He said they were still fucking. She keeps asking for it. I asked how did it happen. He then said that his girlfriend had bragged to Jan about my big dick and how good I could fuck. Jan shared information and told Jodi my dick was average at best and I had premature ejaculation issues.

I never stood a chance. We broke up and just a few days later, Jodi found out Mark and Jan were fucking so she broke up with Mark. I called Jodi later asking her out. She said don’t call me again and hung up. Mark and Jan dated until we graduated and eventually split for college. Me and Mark are still best friends till this day. We are both married with kids.

The one thing I learned was you can’t underestimate the power of a big dick and I have a severe Cuckold fetish. O.K. That’s two things. I’m hoping to get him to fuck my Wife and let me watch.


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