The time my boyfriend gave me permission to fuck my best friend. [MF]

So I’ve been thinking about writing this out for awhile now. I’ve been a long-time reader of this sub, but I’ve always been too shy about my writing skills to contribute. I wanted to tell you all the story of the time my boyfriend gave me permission to fuck my best friend.

My name is Alice. I’m white, about 5’7”, with medium length dark blonde hair and glasses. I have really good skin, so I almost never wear makeup. I have a pretty ballin’ figure – 36-29-37. This story takes place during my senior year of college, which made me 21 years old at the time. I had been seeing my boyfriend, Jake for a few months. He was cute, outspoken, and the life of the party, but this story isn’t about him.

I had been dating Jake for about six months when I met Dean. While I loved Jake very much, Dean and I clicked right away. We had many mutual friends on campus, and so hung out nearly every day. I found myself seeking him out more and more. Now, Dean was pretty much the stereotypical nerd. Shy, introverted, with a passion for technology and Dungeons and Dragons. He was cute in his own way, with unruly dark curls, a full beard, and broad shoulders. Dean stood over 6 feet tall and had the deepest brown eyes I’d ever seen. I kept finding reasons to be alone with him, to sit next to him, to brush my leg up against his. I admitted to myself that I was fully smitten, and somewhere along the way Dean and I had formed a very close friendship.

After a few months of this, I felt a huge guilt. I confessed my feelings for Dean to Jake. In tears, I explained the crush I had developed, thinking that Jake would break up with me on the spot. To my surprise, Jake was pretty okay with the whole thing. He told me that it was natural to have feelings for other people, and didn’t we have friends who were polyamorous? After confirming that nothing more than the occasional hug had passed between us, Jake suggested that perhaps Dean and I needed to get all this sexual tension out of our systems, and gave me permission to try to court Dean into my bed.

I was ecstatic. The next time Dean made a suggestive comment my way, I fired one right back at him. Never one to play games, I sat him down and told him about the conversation I had had with Jake. Dean was blown away, but was thrilled at the idea of us finally hooking up. We set a date for the next weekend, where I would come spend it at his place.

I arrived the next weeekend feeling nervous. Dean and I were such close friends by this point. What if things didn’t go well? What if, after all this buildup, he didn’t actually find me attractive once he was in bed with me? What if I flubbed the date and didn’t even get that far? We started by watching a movie on the couch and cuddling. Dean was a lot bigger than I was, and I loved the feeling of laying back against him with his arms around me. I was aware of every part of my body that touched his. There had always been sexual tension between us, but now it was even moreso. Knowing that we wanted each other and that we could have each other at any time changed the mood of the day drastically.

We had been chatting through the movie, which was one I had seen before. About halfway through, I looked up at him to make a comment and decided this was a moment as good as any. I leaned up to kiss him. He kissed me softly, almost chastely. I leaned into his chest while we kissed, his arms still wrapped around me. We remained this way through most of the movie: talking, kissing, and occasionally breaking into giggles because after all this time we were actually, finally doing what we’d dreamed of for months. My heart was fluttering, my skin tingled beneath his hands. I wanted more, but we were on the couch in his living room in the middle of the afternoon, with his four roommates home.

We made dinner and socialized with Dean’s roommates throughout the evening. We decided to move into his room to watch some TV for a bit before bed. As much as we wanted each other, we were both very nervous. Neither of us wanted to fuck this up, and both of us had Jake in the back of our minds. We cuddled on his bed while watching Scrubs and decided around midnight that we should try to sleep. I got about no sleep that night. Between being in a different bed and the thrill of being in bed *with Dean*, I was very restless despite being so tired. Dean and I spooned on our sides, and I tried my best to get some sleep. We both slept very lightly.

Around 5am, I was relatively awake and noticed Dean shifting. I rolled over in his arms to find him watching me. I leaned up to kiss him. We kissed slowly, with our hands resting relatively still on each other. Dean rolled over to be on top of me and continued kissing me slowly. I was so on edge already that I was getting aroused pretty quickly. Everywhere he touched me seemed to burn. I pulled his shirt over his head and continued exploring his body. I ran my hands all over his back, chest, and shoulders. I’m a sucker for a man with broad shoulders. Dean slipped his hand under my top and was caressing my stomach while kissing the side of my neck. He pulled down my collar to kiss lower. He was teasing me. I was squirming and trying to take my top off for him, but he was having none of it. He used his weight against me so that I couldn’t get myself in a good position to undress myself. He kept kissing me, touching me, *smirking* at me – I wanted him badly, but he was going to take his time and make me wait.

Finally – *finally* – he pulled me forward so I was sitting up and pulled my shirt off. Since we had been sleeping, I wasn’t wearing a bra. I have C cup breasts with pink nipples, which at this point were already very hard from all the teasing. He pushed me back down and caressed one breast with his hand while kissing and sucking on the nipple of my other breast. I was in ecstasy. My hips seemed to be bucking against him of their own accord. I felt like I had no control over my body anymore. Dean alternated by kissing my neck and my breasts and I thought I was going to come right there. My panties were very, very damp. My whole body was on fire. I couldn’t think, I couldn’t do anything except squirm and moan, trying to keep quiet so his roommates wouldn’t hear. I could feel his erection pressing into my thigh and I wanted so badly to rip his pants off and fuck him, but Dean was not going to pass up the chance to spend as long as possible teasing me.

“You promised me hand-tying,” Dean growled, nuzzling my ear as he loomed over me. Dean and I had discussed what we wanted our first sexual encounter to look like. He loved being tied up and I loved being held down. While this seemed incompatible, we decided we would just take turns.

“I did,” I gasped out. When did I start breathing heavily? I could barely think, let alone form coherent sentences.

Dean smiled at me and leaned over to his nighstand, pulling out a couple of men’s ties. He offered them to me, and I pushed his shoulder to indicate he should lie back. I tied each one of his hands to the headboard and sat back on my heels to admire the sight before me. Here was Dean in the pre-dawn light, sprawled out on the bed. Topless, still wearing his pyjama pants that were tented up where his erection was straining against them. As much as I wanted to strip him down and ride his cock right there, I decided some payback was in order. I started by kissing his neck and jawline, while I let my hands roam over his stomach. I would trail my fingers down to his waistband, then bring them back up. Occasionally, I would slip my hand into his pants to brush my fingers along his lower hips, never actually touching him where he most wanted to be touched. I started kissing his chest, moving lower and lower just to change my mind and come back up to his lips again. I decided he needed a better view, and took my pyjama bottoms off, leaving on only the black lacy thong I had specifically picked out in case of sexy times.

“Oh God,” he was breathing. “Oh God, please. Please,” he was trying to keep quiet but couldn’t help himself. He wanted me. I felt so powerful. I decided to oblige him and pulled down his pants and underwear all in one go. This was the first time I had seen Dean naked. He had an average-sized dick, about 6 inches. Thankfully, he firmly believed in manscaping and had trimmed the area. This would make my job a lot easier. I lowered myself down to be at eye-level with his dick. I decided I wasn’t done teasing him yet. I started by licking the shaft from balls to tip. He groaned and started squirming ever so slightly, still chanting his refrain of “Oh God,” and “Please,” under his breath. I had never been with a man who was so vocal before, and I was loving it. I continued licking his shaft, occasionally taking just the head of his cock into my mouth. I wass alternating between sucking the head and licking the shaft, continuing to tease him as he had been teasing me before. Without any break in the rhythm, I suddenly took his whole dick into my mouth. I’m no deep-throat expert, but Dean having an average sized cock meant I could take it all without any trouble. I looked up with his cock in my mouth to find him watching me. We locked eyes and I realized I was so turned on just by giving head, I might have been enjoying it more than he was.

I continued sucking Dean’s cock for a few minutes, but I didn’t want him to come yet. Dean had assured me that he had a pretty quick refractory period and could go several times in an encounter, but I was super horny and didn’t want to chance it. I crawled back up to kiss him deeply.

“You promised me you’d pin me down and fuck me senseless,” I murmured in his ear. I wanted him, and I wanted him now. I untied his hands and flipped over onto my back. He’d told me he wanted to fuck me missionary, as he wanted to see the look on my face as he slipped into me for the first time. He grabbed a condom from the nightstand and rolled it down on his cock. It was swollen and red after all that sucking, he looked as turned on as I felt. I was still wearing my panties, so he hooked his thumbs into them and pulled them down. He stared at my body appreciatively and for a moment we just looked at each other without saying anything, like *holy fuck we are actually going to do this*. Dean settled himself between my legs and lined up his cock with my entrance. I have bigger pussy lips (I’m never going to be a porn star, sadly), so I’m harder to get into. I helped guide him inside of me and with a single push, he was in. I wanted to cry out with joy, I felt so full and wonderful and this was amazing.

Dean apparently felt the same way because suddenly, he grabbed my wrists and pinned them above my head. He leaned into my wrists almost painfully as he started fucking me furiously. There was no more teasing or finesse, he was pounding into me quickly and hard. I bucked my hips up to meet his, taking him deeper with each thrust. There was no way he could keep going at this pace after all our foreplay, and sure enough, he started groaning and thrusting even deeper. He came inside of me while pinning me down and I was more turned on than ever. I didn’t want our session to end just yet.

Dean pulled out of me and took off the condom filled with his come. He pulled out a second one and started rolling it down on his still-erect cock immediately.

“Um,” I interrupted. “Aren’t you going to wait to soften and then get hard again? Won’t the condom get all weird?”

Dean started chuckling. “Who can be soft when you’re around?” He asked, while grinning at me. Suddenly, he was on me again, kissing me and grabbing my breasts. He slipped inside me much easier this time and started fucking me again. He hadn’t been kidding about that quick refractory period. I was more turned on than I had ever been in my life, I was moaning and squirming and running my hands all over his body. I couldn’t even think, I was just acting purely on instinct. I’m not sure if it was because I was nervous, but I couldn’t get over the edge into orgasm territory. I had him but I wanted more, *more* of him. I was grabbing him everywhere I could reach, holding him close to me, pulling him in deeper as if my life depended on it.

“I want to be on top,” I choked out. I was so frazzled and horny, I don’t even know how I was still forming coherent sentences at this point. I pushed him over onto his back and straddled his cock, sinking down onto it, revelling in the feeling of being stretched out and filled. I leaned back slightly and his cock found my sweet spot, It felt amazing and I was so close, but I just couldn’t get over the edge. Dean put his thumb on my clit and starting slowly circling it. I looked down at him and he was staring up at me with this lust filled expression like I was some sort of goddess, and suddenly I was coming hard, my pussy clenching and spasming around his dick as I cried out in pleasure.

I grinded on his cock slowly as I felt the aftershocks of my orgasm surge through my body. Dean held my hips and pulled me in closer to kiss him again. He wrapped his arms around me and continued kissing me as he pulled out and brushed my hair away from my face. We laid like that for quite awhile until we realized that it was after nine in the morning and our entire encounter had taken about four hours, and that we should really get up and face the day.

Unfortunately due to circumstances, that was the only time Dean and I ever slept together. We are still the best of friends to this day, and he was one of my groomsmen when I married Jake a couple of years ago.

Thank you all for reading!

Source: reddit.com/r/gonewildstories/comments/8ib1hg/the_time_my_boyfriend_gave_me_permission_to_fuck