[MF] The One (And Only) Time I Cheated: Sleeping Between My Ex-Girlfriend And Her Friend

When I was 18-years-old, I landed my first legit girlfriend. I say “legit” because I had dated before, but never started a relationship. Tara was one year older than me at 19 and played tennis at a small college three hours outside our hometown. We had been friends for a year or two and then one day we were like, “Hm. Maybe we should fuck,” and that was the start of a beautifully dramatic relationship. Tara’s best features were her legs and ass. I suppose it was all the tennis. She had smaller than average tits and a pretty standard face. I DON’T KNOW IF THAT SOUNDS MEAN! It’s not meant to be. Obviously I was attracted to her.

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Our one year relationship was a tumultuous one. It was long distance for the most part as she was in college and I was still at home. Admittedly, since I was just an 18-year-old little douche, I was a bit jealous. I thought about all the guys at her college. All the older dudes who were probably more experienced than me. My silly paranoia created a few fights, but I wasn’t the only one adding unnecessary stress to the relationship. Tara had some personality disorder. I’m not going to claim to know the specifics behind it, but her father was a high-functioning alcoholic and her mother was out of the picture. She, understandably, had some issues.

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She wasn’t the jealous type, but she was controlling. She had two sides to her. One minute she was so happy and intoxicating, and then the next she was a fucking demon. That’s the only way I can describe it. It was painful to watch because I could see how much she struggled with it, and while I tried to be there for her, I was just 18. I barely knew how to do my own laundry.

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Most weekends I would go down to her apartment to visit. Tara didn’t have many friends, but she did connect with a few people from tennis. One of those people being Rachel. She was shorter than Tara, had bigger boobs and just more curves overall. She didn’t really scream “tennis player” to me, but obviously she was good enough to play in college. Sometimes we’d catch a movie with Rachel at the theater or maybe grab a bite to eat, and then she’d leave us to go off with her boyfriend.

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But during one weekend, I arrived at Tara’s apartment and found her comforting Rachel on the couch. Rachel and her boyfriend had apparently broke up just two days before. They were watching ‘Mean Girls’ when I walked in, ’cause that’s what everyone should do when they’re depressed. Mean Girls is the shit. Tara jumped up to “fill me in” on everything in the kitchen. I asked her if I should leave and she was like, “No, no! We’ll have fun!”

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After the movie was over, we decided to order pizza and watch more chick flicks. I was sitting on one side of the couch, Rachel on the other and Tara in the middle. It was a little awkward as I felt like I was invading their time of bonding, but Tara assured me again it was cool. I’m not going to lie. It was actually kinda nice to be “one of the girls” for the night…as strange as that sounds. We all shared a big blanket, snacked on a bunch of unhealthy shit and sipped on wine. I would have never attempted anything like this with my guy friends.

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A little after midnight, Rachel started to get emotional again. I think she was triggered by some scene that reminded her of her boyfriend. She started to cry a little and that’s when Tara suggested we should all just go to sleep.

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“I really don’t want to be alone,” Rachel said. I got the hint that she wanted to sleep with Tara, so I offered to sleep on the couch.

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“No, no. It’s a queen. We can all fit.”

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“Are you sure?” I asked.

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“Yes. Don’t be weird.” Tara replied.

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Well, okay then. “I guess it’s not a big deal,” I thought. It IS a big bed and I’m sure Tara would be right in the middle. I decided to take a shower before getting in bed because it was hot as fuck outside and the A/C in my car was wonky, so it was a sweaty drive to the college.

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When I got out of the shower, I entered the bedroom to find both Tara and Rachel asleep. I suppose the wine and junk food knocked them out. Tara was on one side of the bed and Rachel on the other. I tried to wake Tara up so she could move over to the middle, but she got annoyed and angrily whispered, “Just get the fuck in bed,” so I did just that because Tara wasn’t the person you wanted to wake up more than once.

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I gingerly moved over Tara and claimed my place in the middle of the bed. I tried to make sure I was closer to Tara than Rachel when I fell asleep.

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When I woke up (two? three?) hours later, I realized I had turned on my side and was facing Rachel. She was also on her side (her back facing me) with her body just inches away from me. I was too tired to care or move and ended up falling back asleep a few minutes later.

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Fast forward another few hours (I’m guessing, who really knows) and I wake up to Rachel grinding her ass against my morning wood through my boxers. I stayed there completely frozen. I didn’t know what to do. There were so many thoughts going through my head…

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1. God this feels good
2. God this feels wrong
3. Should I move?
4. Is she asleep?
5. Am I dreaming?
6. GOD THIS FEELS GOOD
7. GOD THIS FEELS WRONG

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I decided to just stay frozen because I mean, I was a horny 18-year-old and Rachel’s ass felt incredible grinding against me. It was harmless anyway, right? Wrong. Rachel was awake. She knew exactly what she was doing because she looked back at me briefly with her sleepy eyes. I think she was a little surprised to see that I was awake as well, but she didn’t stop wiggling her ass against me. I looked under the blanket to see that she was wearing a thong. Her bare asscheeks were pressing against my cock, which was still (barely) covered by my boxers.

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I pulled myself closer to her and whispered, “What are you doing?”

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“Ask again and you’ll ruin it,” she whispered back. And from there, no more questions were asked. She reached back, grabbed my hand, and placed it on her breast. She wore a tank-top that was too small for her. I squeezed her tits roughly and pinched her hard nipples through her shirt. She pressed her ass harder against me and I leaned forward and started kissing her neck. I slid my hand up her tank-top and teased her nipples with my fingers.

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She moaned softly and then reached under the blanket to pull my boxers down to my thighs. My cock bounced against her ass. I still believe this was the hardest I’ve ever felt my dick. It honestly felt like it was about to explode. It was almost painful. The head was incredibly sensitive as it rubbed against her warm ass. I slid my hand past her stomach and inside her thong. She was already wet, which made me wonder how long she had been rubbing herself against me.

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The moment my finger brushed her clit, she moaned and it was too damn loud for my liking. I slid my hand back up her body and covered her mouth with it. “You have to be quiet” I whispered. She nodded and I lifted my hand from her mouth, she stuck out her tongue and licked my fingers before I placed them back on her clit. I rubbed her clit with my middle finger as she worked her ass against my cock. I could feel her moving her body higher up the bed. She was trying to get in position.

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She slid her hand down to my cock, wrapped her hand around it and guided it inside her pussy. This time it was me letting a moan slip out. “Shhh,” she smiled. She moved herself SLOWLY against me. I mean, we were barely fucking. It was mainly just my cock pulsing inside of her as I rubbed her clit. We couldn’t move much for obvious reasons. Rachel buried her face in the pillow as I continued to gently brush against her clit with my finger. I tried my best to keep a rhythm going, but for fuck’s sake, I was only 18 and this was by far the hottest thing that had ever happened to me.

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Our bodies felt so warm against each other. I could feel her ass just pressing against my body, begging me to push my cock deeper inside her pussy. I started to thrust into her in the most discreet way possible. She moaned, but most of the sound was covered by the pillow. I was barely hanging on. Actually, I wasn’t holding on. I was going to cum at any moment, “I’m about to cum” I whispered directly into her ear, hoping she’d let me know if it was okay, or if I needed to pull the fuck out, but she didn’t say anything. She just continued to move her body against mine.

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I couldn’t hold back. My dick started to erupt inside her warm pussy. It felt like it nearly doubled in size, and apparently the throbbing of my cock was enough to push her over the edge. I wish I could say I timed this mutual orgasm, but it was all luck. As shot after shot of cum pumped inside her pussy, her ass and thighs started to shake against me. I looked over at her and she was biting down on the pillowcase. I held my fingers against her clit as her orgasm spread throughout her body.

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Rachel was breathing hard when she turned her head to face me and kiss me gently on the lips. She smiled and then slid out of the bed and walked to the bathroom. She turned on the shower and that’s what woke up Tara. She reached over and grabbed me to cuddle. My dick was still out at this point, covered in Rachel’s juices. I was afraid she would want me to turn around to face her, but thankfully that didn’t happen.

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“I have to pee so bad,” Tara said. Rachel was taking forever in the shower, so finally Tara just jumped up to see if the bathroom door was locked. It wasn’t, so she walked in and went pee. I took this time to run to the kitchen and clean up with a paper towel. As far as I know, Rachel never told Tara about this incident, most likely because we broke up a short time later for other reasons.

Source: reddit.com/r/gonewildstories/comments/b3ul2v/mf_the_one_and_only_time_i_cheated_sleeping