I [M] broke the tension and fucked my ex’s best [f]riend

When I was younger I was good friends with 2 girls, Fiona and Janet. They were best friends but they were complete opposites. Fiona was uptight, insecure, and conservative; Janet was quiet yet easygoing with a wild streak. Fiona was intense about her career and found great success. Janet bounced around various service jobs and partied every weekend. Of course, Fiona was the one I fell in love with and dated for years.

I was always attracted to both of them. Fiona was pale and skinny with big breasts. Janet had darker skin and hair with wide hips and juicy thighs. But unlike Fiona, Janet was *sexy*. In the way she talked and moved and everything else about her. She was confident and mysterious. She was in never in a relationship and usually just hooked up with older men outside our friend group. My friends lusted after her but she wasn’t interested.

After I started dating Fiona, Janet was often the third wheel in our relationship. Going out to eat, to movies, things that friends do. Sometimes it got a little more interesting, like when Janet drove Fiona and me back to my place one NYE. We left Janet to crash on the couch while we had a huge fight upstairs followed by makeup sex. I knew that she gave Janet the intimate details of our sex life, and Fiona had even hinted to me that she bragged to her friends about my penis size.

One time Janet hosted a party at the house where she was living. Fiona was uncharacteristically forward and horny that night. At one point my friends drafted me to roll a joint, so I went to Janet’s bedroom where we had put our stash. Fiona followed and locked the door behind her. I sat down to roll the j and she unzipped my pants and started playing with my cock. I started getting rock hard and gave up rolling as she pumped me up and down. Then we froze like deer in headlights as we heard a key unlocking the door. It was Janet. She looked at the scene with a mix of annoyance and amusement, pointedly glancing at my cock in Fiona’s hands. “Just make sure to clean up,” she said and walked away. I was a little embarrassed but Fiona was fine. She got on Janet’s bed and pulled her pants off. I quickly pounded her and got back to the party.

Time passed and Fiona and I started having ups and downs that devolved into constant fighting. She tried to force me to be a better version of who I was. I wasn’t ready to grow up yet. I broke up with her rather abruptly and broke her heart. She lost it and began to hate me. We met to exchange each other’s things we had shortly after. She made me feel awful about dumping her and made two rules: I couldn’t hook up with anyone until she moved on, and I was never, ever to hook up with one of her friends.

The first rule I disregarded, but I couldn’t let go of the second. She had a point. Were the roles reversed and she hooked up with one of my best friends, I would be devastated. Regardless, I started moving on. I still saw Janet every now and again. It was a little awkward at first. No doubt she had heard the sordid details of the breakup from Fiona, to whom I was public enemy #1. But she didn’t seem to act different toward me, to my relief.

One summer night my friends and I had come back late from bar hopping. We still felt like hanging out, and just as a joke given the late hour, one of them texted Janet and told her to come over. To everyone’s surprise, she responded that she would be right there. She had just got off her shift bartending and was still in her “uniform,”–eye makeup, a blouse unbuttoned and tied above her midsection and impossibly short jean shorts. Everyone, myself included, was stunned when she walked in. All of us (male/female/gay/straight) thought of Janet as “the hot one” in our crew. But we had never seen her like this. She joked that it got her good tips, then sat down, kicked off her shoes and unbuttoned the top button on her shorts to get comfortable.

We all stayed up until sunrise laughing and reminiscing. Finally people started to go home or retire to the bedrooms. I volunteered to sleep on the pull out couch and to my surprise, Janet asked to share. I assumed it would be platonic and said sure, knowing that I would struggle not to get a massive erection. We unfolded the couch and Janet turned her back to me. She took off her shirt and pants and unhooked her bra before putting her blouse back on and doing one button. We got in bed, keeping our distance, and began to talk. She criticized me for things I had done to Fiona, none of which I didn’t deserve. But she told me she and Fiona hadn’t been getting along recently either and weren’t speaking. We talked some more, half-hugged, and went to sleep.

A little while later I had a party at my place that quickly got out of control. Way too many people were there, including Janet. I had been fantasizing about Janet since that summer night. But she still felt unattainable to me.

My living room became a dance floor, lights were turned off, music was turned up. The punch I had prepared with an excess of vodka and moonshine was flowing freely. I took a break from the madness to do a check around the house. Smokers on the back patio. My lightweight friend getting sick in the upstairs bathroom. A random guy making pasta to an audience in my kitchen. I checked the front stoop and saw one person out there smoking a cigarette. It was Janet. My heart started to race but I told myself not to get too excited. We were just friends. I grabbed a cig from my back pocket and went outside, winging it.

As soon as I walked out my front door and Janet turned to look at me, I felt an unbelievable energy. Like a pot about to boil over. It was burning hot and electric despite the cool night. I knew she felt it too by the look in her eyes. The sounds of the party inside felt miles away as we started to talk and make pleasantries. But in an instant we snapped together like magnets and kissed each other deeply. She opened the door and started leading me to my bedroom. I was in disbelief–*this is really happening*. For the brief moment my rational brain could form a thought, I remembered Fiona’s rule. But instinct took over. Besides, Janet, her supposed best friend, was in on it too. Fiona could often be controlling and bossy. In a sick way, it felt cathartic to cross her like this.

Before I could even close the door to my room, Janet was stripping off her clothes. She jumped on the bed and I got on too. She unbuttoned my pants as I took off my shirt, pulling out my cock at full mast. “I heard you were big,” she said coyly before beginning to suck it vigorously. I had been with some girls before and after my ex, but none of them blew me like this. She worked the head, deep throated, and grabbed my balls to tease me. But I knew I wanted more. I flipped her on her back and kissed down from her neck, down to her nipples, stomach and waist. She started breathing heavily as I licked her pussy, which tasted like nectar. I couldn’t wait any longer. I popped back up and slowly slid inside her, inch by inch. I started to thrust, working up speed and she began to moan and say my name. For years, I considered Janet almost *intimidatingly* hot. And here I was, deep inside, holding her body as she wrapped her legs around my thighs and dug into my back with her fingernails and came. I finished soon after and pulled out right before I shot a massive load uncontrollably. It covered the bottom of her waist and her abs that pulsed up and down as she caught her breath. She scooped it off and licked her finger. She told me I tasted amazing.

We laid there a bit before the inevitable round 2. I went back to the party and she said she was tired and would stay in bed. I tried to make small talk as I made the rounds but I couldn’t stop thinking about Janet. How much better she was than my ex. How *I* just fucked *Janet*. How she was still lying there underneath my sheets naked.

I went back up after an hour and got back in the bed. At first I thought she was sleeping, but soon her hands made their way over to my dick and started playing with it. I grabbed her ass–really grabbed it–for the first time. “You like?” she said knowingly. It was firm yet bubbly. We started kissing and then fucking again. And again. And again and again. I lost count. Still have no idea how I kept it up for so long.

At 3 in the morning I had her face buried in a pillow with her ass up, fucking her hard. “Right there!” she screamed and I stopped. “Right there…” she moaned again. I paused with the widest part of my cock, right below the head, just inside her opening. She rocked back and forth on it, tensed up, and came hard.

She left pretty early the next morning. We said goodbye, didn’t talk for a few days, then texted back and forth a bit before completely falling out of contact. I spoke to my ex a few more times but it always got uncivil fast. I never told her about what happened with Janet, and she never called me on it either. A few years later Janet randomly got in touch with me again after I had moved to a new city asking if she and a friend could stay with me for a weekend. I obliged and we ended up hooking up again.

Source: reddit.com/r/gonewildstories/comments/kffxm8/i_m_broke_the_tension_and_fucked_my_exs_best