[M] The time I cheated with my best [F]riend from college

This happened a couple years ago. I think the backstory adds to this, but those that want to skip it can scroll down to the “- – -“

I met Annie during a chemistry lab our freshman year of college and we kept up over our time at school. We flirted on and off over that first year, but eventually she started dating someone else. It hurt, but I put a relationship with her our out of mind and focused on being friends. Some of my best memories of college were with her, lounging and watching Netflix in my apartment or playing horror games. Inevitably, we would end up leaning against each other during a movie or jumping, screaming, and laughing onto each other. Nothing sexual, but there was always a certain tension I couldn’t help but hope would snap. But she would always leave once we were through for the night, and nothing came of it.

I met her girlfriends or boyfriends as they came, and drank with her and talked shit with her as they went. Every breakup would rekindle that smoldering hope of us having a chance, but it never happened. Then we graduated, I moved back home, and she stayed in town for an internship. We stayed in touch though, sharing memes and the woes of online dating. She’d gotten back with a guy she’d dated in college, and I was a bachelor in a two bedroom apartment nicer than I had any right to be in at the time. Not that I’d gotten anyone back to see it. I technically lived with a roommate, but he traveled so much for work that I basically had the place to myself.

I had enough swipes, matches, and first dates to keep me busy, but far fewer second dates and nothing ever really came of them. So I didn’t have any plans when a holiday weekend rolled around and Annie didn’t want to be alone in our college town. Her boyfriend was traveling and she didn’t have any family in-state, and I had a “guest” room since my roommate was fairly clean and what he didn’t know wouldn’t hurt him. Besides, it’s not like we were gonna fuck on his bed or anything.

Annie made it up just before dinner, so we went to grab drinks and a bite and catch up. I couldn’t keep my eyes off her as we left the apartment. She’s nearly platinum blonde, hair just past her shoulders, gentle facial features, and shorter than me (about 5’5” or so). God, had I missed her ass though. Perfectly shaped for her hourglass frame, it would turn heads wherever she went. It was a mild winter, but cold enough to warrant a jacket. And the walk to the car was a blessed sight of that ass in tight jeans, swaying underneath her black pea coat.

After dinner and a few drinks, we went back to my apartment and quickly fell into our old ways. It was like we were back in simpler times again; comfy clothes and playing PS4, drinking whenever we got killed in whatever we were playing. And laughing and getting closer. And drinking and laughing and snuggling on the couch. She got up for another couple of ciders and said she wanted to see the balcony. I thought I could use the cold air at this point, so I led the way outside.

The temperature was sobering, but I didn’t notice much. All my swimming mind could focus on was Annie as she looked out over the balcony. She was still so beautiful, and she was one of my best friends, and she was so…here. I walked up beside her and put a hand on the railing to keep from swaying. I turned to look at her and she was already looking at me with something I’d never seen from her. I’d later realize it was lust.

Something bold (definitely the alcohol) took over me. I moved closer and she didn’t pull away. Her eyes flitted between mine and my lips. “Are we really doing this?” she whispered. I answered with one of the hungriest kisses I’ve ever given, and she responded in kind. Hands were grasping at clothes and our breath plumed hot in the chilly air. The blinds rattled when I ushered us back inside and closed the door hard. We were already back on each other.

—

I was bending to kiss her, so Annie pushed me back to the couch and was straddling me before I registered what happened. Thankfully I hadn’t had so much to drink that whiskey dick set in, and I had been so hard that it hurt nearly since the first kiss. The way she ground herself on top of me made it all worth it though. She shuddered as she continued, and pulled my head to the side to expose my neck. I could never have dreamed about the things she did to me with her talented mouth, and I will do anything for neck kisses to this day.

It started as a reflex, but I soon realized that I finally had her perfect ass in my hands. I dug in deeper, slipping my hands under her pj pants to get a grip of bare skin, and she made a sound into my neck that was equal parts squeal and moan. I nearly came right there, but I held on and I needed more.

Against every desire in me, I let go of her to pull her shirt over her head. I don’t remember what kind of bra she had on, or if she even did. My hands went back to her ass and pulled her in closer to me, grinding on me. Her hands were wandering too at this point, and she pulled my mouth to her chest. I’d known that Annie had great tits, but they’d never been my focus with her. Once they were in my face though, they were perfect and I wanted nothing more than to have them in my mouth. Our breathing at that point was nearly feral.

Due to a private school upbringing, I had never gone all the way with my girlfriend in high school. I’d made up some of the lost experience with college flings, but there’s one thing I did get plenty of practice with. Dry humping endurance and using my tongue. Thank almighty God, because I needed both right now. My tongue swirled and flicked around her tits, while she continued to ride me like a stolen horse and I held onto her ass for dear life. Even with my practice, I still had limits and I was fast approaching them. I was nowhere near through with her though, and the feeling seemed mutual.

The rest of our pj’s were torn off and Annie tried to climb back on top of me, but I knew that I would explode as soon as I slid inside her. So I stood up before she had the chance and pushed her back onto the couch. I knelt in front of her and spread her legs around my torso, pulling her into another ravenous kiss. Gradually, my kisses started trailing south, being sure to stop at her neck, nipples, and stomach. The sounds she made were growing less voluntary and more guttural, so I took even more time.

My fingers slid into her before my tongue did, but they didn’t need the help. She ran her fingers through my hair as I looked up at her, flattened my tongue, and ran it up between her lips. I thought she was going to crush my head in her thighs and I would have been perfectly happy to die that way. But her legs loosened and I could still breathe, so I kept working to make my friend cum her brains out. My tongue and fingers worked together, while the other hand snaked underneath her and took another handful of that perfect ass. Anything that made her whimper was repeated with enthusiasm, and it wasn’t long before her breathing hitched, she groaned like an animal, and her thighs threatened to behead me again. She collapsed onto the couch and pulled me up into a kiss wet with her juices.

After a moment, Annie stood up shakily and pulled me to my feet before taking my hand and leading me to my bedroom. Once again she pushed me down, but this time she remained standing. She spat in her hand and began to stroke me before leaning down and whispering one of the hottest thing I’ve ever heard. “Relax. It’s my turn to take care of you.” She finished the sentence by taking as much of me into her mouth as she could, and to this day I don’t know how I didn’t erupt in her throat.

Encouraged by the groans she pulled out of me, Annie kept bobbing up and down on me, taking quick breaks to continue stroking me before I was back in her mouth again. She must have felt me getting close because she stopped and climbed onto the bed with me at that point. She straddled me again and I put my hands on her hips, guiding her down onto me. I slid past her lips and into the tightest grip I’d ever felt. My grip tightened on her hips and she half-sighed, half-squealed as she began moving on me. Every stroke made me feel like I would burst, and I held out as long as I could. But I’m only human and I tried to tell her as much. “Annie…I’m gonna…” was all I could get out between breaths. She heard me, because she doubled the pace and pulled me into a crushing kiss. “Do it. Do it, give it to me.”

In hindsight, it was a risky, reckless move without protection and only trusting that Annie was on birth control without having talked about it. But in the moment, I could not have given a fuck less. I pulled her down by her hips came in her so hard that I saw stars and my mind went blank. It was one of the best orgasms of my life, hands down.

We stayed there for a while and basked, fingers grazing over each other. We took turns cleaning up after, but that’s about when the reality started setting in. She’d just cheated on her boyfriend with me and was still staying the night. We awkwardly said our good nights and she slept in the other bedroom. The next day was even worse. We talked, nearly fought, and ended up both swearing we’d never tell anyone. She told her boyfriend after a few weeks though, and they broke up not long after. She wasn’t ready to try us dating after that, but we kept being fuck buddies for a few more months. There’s another story there if you’re interested, but overall the whole shift nearly ended our friendship. Miraculously though, we’ve stayed friends through it all and have both moved on to happier, healthier relationships that aren’t just using each other for sex. It’s a hell of a thing to look back on though.

Source: reddit.com/r/gonewildstories/comments/yhng3q/m_the_time_i_cheated_with_my_best_friend_from