The one where I fucked my brother’s best friend [MF] [cheating]

*Another one of my cheating stories from the past. This one was the last time I cheated, not just on this particular ex, but ever. If you have not read my previous stories, the important thing to know is I was in a bad relationship with someone who was controlling, manipulative, degrading, and abusive (mainly mentally and emotionally, but some physical aspects showed through here and there -pushing, throwing things, slammed me into a wall and raised a fist up but didn’t it).*

**Backstory:**

This took place in July, the summer before I turned 21. It was the summer between my sophomore and junior years of college, and my brother had just graduated high school and was preparing for college in the fall. I was home at my parents’ house for the summer, but they took a long weekend trip at a beach about 3 hours away, My brother thought it would be a good idea to throw a party in the house and invite his friends who were all preparing to go in separate directions to college in the fall. He also thought it was a brilliant idea not to inform me that I would be coming home to a house full of about 30 18-year-olds that night . I had been shopping and out to dinner with my best friend, Alyssa Throughout our shopping trip, my asshole boyfriend kept calling and asking where I was. He heard the noise of the mall in the background and swore I was at a party. Then, when I got home to an actual party and he called, he heard it in the background and screamed at me. I hung up , but he kept calling, and calling… I felt my heart racing with the stress he was putting me under. I couldn’t deal with it anymore, and I had just walked into a fucking shit show in my parents’ house. My brother finally emerged from the crowd to apologize for inviting a few people over without telling me, and to inform me that those people brought more people. I thought, “fuck it” and said , “Fine. we drink for free” (referring to myself and Alyssa), and opened us each a beer. Then, I did this wonderful thing and walked down to my bedroom threw the phone on the bed, locked the door and shut it behind me as I left. It had about 2% battery, and I wouldn’t hear it ring over all the noise. Soon, it would be going straight to voicemail. There would be hell to pay for that move, but it felt damn good. It felt as if a thousand pound weight lifted off my chest when I returned to the party without my phone and started playing some pong. My brother and I made an excellent team, and his best friend, Jack, was unpleasantly surprised at my newfound talent I gained in the previous few months.

Jack and I had some history. He had a crush on me from pretty much the day we met (when he was 9 years old and I was 10). He is a year older than my brother, so 19 in this story, and he was dating this girl Lynn for a year; He went on to date her for at least 5 years after this. Jack even kissed me once when we were 13 and 14 behind the bleachers at a high school football game. I let it happen for abut 5 seconds before feeling weird since he and my brother were best friends, he was in 7th grade when I was a freshman (big deal at that age I guess). He then decided to tell people we made out for half an hour .. because that’s what 13 -year-old boys do apparently. Anyway, Jack was always cute, but he had grown up quite a bit over the past 2 years. He went from being super tall and extremely skinny, to tall, muscular, and a definite masculine presence. He is the typical “tall, dark, and handsome” variety, except very tall. He is of Italian decent, 6’6, and clearly works out but still thin. His skin is tanned to a nice olive tone every summer, and his hair and eyes are almost jet black. Seeing him that night got me thinking about him in a whole new way. He wasn’t just my brother’s best friend anymore. He was very hot. And very taken – and so was I. Despite neither of us being single, we flirted incessantly throughout the night. I was actually starting to think my brother might have noticed, but he was busy hosting the party and helping me make sure the house didn’t get destroyed. Jack’s girlfriend arrived late to pick him up and drive him home, giving me a disapproving look as she walked in to say hi just before leaving with her man. I slept soundly that night for the first time in ages, and woke up hangover-free, surprisingly.

**The night shit goes down:**

No permanent damage was done the night before, but the house smelled like a brewery, and extreme cleaning needed to be done. My brother and I came to an agreement that this night would be best friends only – Jack, Alyssa, the two of us, a case of beer, and a bottle of 99 cherries. Since he is close to incompetent in the cleaning department, he didn’t want to push his luck. Our parents would be home by late afternoon the next day, and I would be doing most of the cleaning . Sometime that afternoon, when it was just my brother and I at the house, I chose to finally charge my phone. I had literally dozens of angry texts, half dozen voicemails, and at least 30 missed calls from my (now ex) boyfriend. Sure enough, he was calling again within a minute of the phone turning back on. I wouldn’t pick up, but he kept calling, with some texts in between. After about a half hour of this my brother was absolutely IRATE that I was being treated this way (he had no idea before). He chose to answer the phone and he essentially told the guy to stop calling me or he was going to kick his ass. Problem solved, for that moment at least. He left me alone for a week after that. I had never been so thankful for my brother than I was in that moment, and that’s saying a lot because my brother and I are close.

Jack and Alyssa showed up in the late afternoon/early evening, and we hung out on the back deck for a long time, but it was one of those hot and sticky summer nights full of mosquitos, so we ended up going in some time after dark. Alyssa was the first to call it a night, and we usually just sleep in the same bed when she stays over, so she went down the hall to my room to go to bed sometime around 11. I had changed into short pajama shorts (the female boxer type), the coordinating tank top, and one of my old cheer camp sweatshirts (it was cold with the AC on in there). Also a side note – I was wearing cotton boy shorts underwear and no bra. The three of us sat at the kitchen table for another hour or so talking before my brother decided it was his turn for bed. He had turned his head for a half a second to look at the time on the kitchen microwave clock since none of us even had our phones with us at the table. In the split second, I felt a hand on my leg under the table – just a slight brush, and I almost thought I imagined it. But I turned my head, and made eye contact with Jack. He nodded his head every so slightly, answering a question I didn’t even have to ask. He said he was going to walk home, but I knew otherwise. My brother went to his room, and he sleeps like a rock. I knew he would be out within minutes. I knew Alyssa was in my bed sleeping, so nothing would be happening there, but I did go in my room to pretend to go to bed and also to grab my phone from my dresser.

At this point, I was wondering if I had imagined the head nodding and leg brushing stuff. What the heck was going on? I hadn’t had good sex since the previous September, and stupidly tunned down an opportunity the previous month. I was really starting to crave being with Jack, even though my brother would kill us both. After what he did for me that day, I really shouldn’t have been thinking like this, but I was. It seemed like an eternity before the screen on my phone lit up. It was Jack. Two words- “back deck”. I hadn’t imagined it at all..the night was on

**The sex part:**

I went outside making as little noise as humanly possible. I was afraid to even fully shut the sliding glass door, so I’m sure a dozen mosquitos used the quarter-inch gap I left as their invitation to the house. Whatever. I was on.a mission..

I went outside, and there he was on the made-for-outside couch my parents still have to this day on the back deck. The first thing I did was tease him about the whole thing that happened when we were kids.

Me: “Oh, I see how it is, you just want to make out for real now so it wound’t be a lie. That’s what this is , right?”.

Jack. “But we really did..”

Me: (cutting him off): “THAT was not making out, and you know it.. but ..’ (straddling him) “this is” (lowering my mouth to meet his). ‘

We continued to make out slowly, at first, but passionately. Hands began wander, and I could feel his erection through his shorts. Fuck. He was huge. Definitely huge. As a matter of fact, I would learn that night he would be my biggest until that point, and one of the top 3 biggest of my life to this date (definitely the thickest)

His hands were up the back of my shorts and panties, resting on my bare ass cheeks at this point. I could feel myself going tingly down below, rubbing my soaking pussy over his cock through our clothing. This was something I never thought I would have been doing two days prior. This was hot and risky as fuck for both of us. His girlfriend was not known for her leniency when it comes to him even speaking to other women. I was good as dead if she found out. We were good as dead if my brother found out. My boyfriend would never find out, and as a matter of fact , I decided that day that I was finally done with that manipulative fucking piece of shit excuse for a human. This was me being liberated – I was free from being a prisoner in my relationship. These thoughts ran through my head, as I nearly went over the edge from all the rubbing, but I had other plans ..

So I got to my knees in front of him and pulled his huge cock out of his shorts, nearly gasping in the process. It was seriously so fucking big and I was about to take it in my mouth. After a quarter of a second’s hesitation, I engulfed it in my wet and ready mouth. I sucked and licked the head , taking as much as I can at once.. slowly working more into my willing mouth. I moved down the shaft, making it wet and sloppy so that it could slide into my soaking pussy more easily – I knew I was about to be stretched. Nothing CLOSE to that size had been in me before . As a matter of fact, my ex was about half the size and less than half the thickness. I continued to give him the best blowjob I was capable of considering his size, with an enthusiasm fueled by his noises of approval. Knowing how he felt about me in the past, the fact that we were both taken, and the fact that we could be caught , the adrenaline rush I was experiencing was off the charts. Soon, he was about to cum and chose to pull me up instead, take his time. Next thing I know I’m naked from the waist down on the outdoor couch , and his head is between my legs. He knew and I knew the more wetness he got all over me, the easier phase two was gonna go.. and I think he wanted to. impress me a bit. Well, that he did. He licked, sucked, and tongue-fucked me with enthusiasm that was unmatched and surprising amounts of talent. I came quickly, but he continued to lick slowly.. slipping a finger in me, then two.. then three .. I think he eventually got 4 in , “Fuck,you’re tight” he said.

I could tell he was in his glory, and that did wonders for the continuously fading confidence I had after years of emotional torture. His confidence at this point was unwavering, and he told me straight out what he wanted, “Bend over”, he commanded. I did what I was asked and got on all fours, face down ass up for him. He tried to enter me from behind, and it literally wouldn’t fucking go in. So without another word I was back on my back, he used his tongue on me again, and in missionary we tried again. No good. Now his high has been crashed, but this was not ruining our night. I was going to make his childhood fantasy come true. I was not going to ruin this for him, and I wanted to get fucked.

I knew immediately what would work. I was going to MAKE it work. “Jack, sit over there like before.” I said. He complied and I straddled him once again, slowly stretching myself around his huge dick and sliding down his length. It was pain, it was pleasure, it was everything all at once. I started riding slowly, kissing passionately, the whole 9 yards.. but he had other ideas. Once I had fully accepted his length and became accustomed to it, he grabbed me roughly and started thrusting back at me matching my movements, pounding me into oblivion. I came again soaking all over him, which sent him over the edge inside of me slowly after. I could still feel him throbbing inside of me as I tried to catch my breath. Funny thing is, earlier in the day he had asked me how many guys I had been with and I wouldn’t answer. As he was leaving the back deck to begin his late night walk home, I decided to give his answer,’ He was already down in the yard, so. looked over the railing and called to him quietly, “Hey Jack” and he looked up. “You’re lucky number 13”. He laughed and went home. We never spoke of this again and no one knows to this day. As I went inside, I realized one of my two cats had been on the porch the whole time on the chair opposite of us. He followed me in giving me what seemed to be a silent look of judgment. This for some reason made me laugh quietly to myself on the way to bed, where I slept like a rock until my alarm went off. The next morning, my brother and I would have won gold had cleaning been an Olympic sport. We put on the performance of a lifetime, breaking all records of quickness and thoroughness. Alyssa and I went to the store to get candles to burn to take the extreme smell of beer out of the house, the AC was turned off and windows open to air it out, and we replaced my parents’ missing alcohol.

The killer of this whole thing is the second they saw how clean it was and noticed that not even an. ounce of alcohol seemed to be missing, they immediately knew there was a party. Why the fuck else would we have cleaned? Plus, they expected us to drink a beer or two. They laughed it off and we never got in trouble, but were told in no uncertain terms to never do it again…

Source: reddit.com/r/gonewildstories/comments/9gw0c4/the_one_where_i_fucked_my_brothers_best_friend_mf

7 comments on “The one where I fucked my brother’s best friend [MF] [cheating]

  1. 4 in you? Oh, girl, that got me. I would have massaged you more, your g-spot, all of it. But then, young guys…

  2. should add .. I forgot my favorite quote from this whole thing. I knew MY relationship was shit but I asked him (while clothed and straddling him ) if he was okay with cheating on his girlfriend.

    His response? β€œWe’re too young not to cheat”

  3. Super fucking sexy. I love the build up.
    My personal favorite quote. ” I was not going to ruin this for him”

    Yes you were obviously into it also but the fact that you knew how much it would mean to him, to lust after you and finally have you, and you were set on making that happen.

    Props girl.

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