My roommate and I gradually went from drinking buddies to fuck buddies, Part 4 (The finale) [MM]

[Part 1](https://www.reddit.com/r/gonewildstories/comments/9tp8oi/my_roommate_and_i_gradually_went_from_drinking/)

[Part 2](https://www.reddit.com/r/gonewildstories/comments/9tpbnl/my_roommate_and_i_gradually_went_from_drinking/)

[Part 3](https://www.reddit.com/r/gonewildstories/comments/9tpern/my_roommate_and_i_gradually_went_from_drinking/)

**Part 4 – The Finale**

We had fucked. We were drunk at the time, but it happened. At the same time, our relationship as roommates seemed to go on as normal. Normal, however, was a relative term. Since our previous parties, nudity became a periodic, yet regular, occurrence. We hadn’t become nudists, but there wasn’t much effort put forth to covering up. Just two nights after our drunken fuck, we were watching TV on the living room couch around 11 pm, this had been the standard routine for a year. It was getting close to bedtime, as we both had to be up early. “I was gonna jerk off before bed, but I want to use this screen,” Mark said, unprompted. “Well I could leave you alone to it or you can put something good up, I wouldn’t mind jacking off before bed,” I replied. After a brief pause, “alright, fuck it,” Mark said as he switched to the TV’s internet browser. For almost an entire week, this became the new routine: hang out after work as usual, end the night masturbating together, and go to bed. The only difference was, we hadn’t seen most of our friends in weeks. We watched a variety of porn, but it was either lesbian or straight. During this stretch of time, we were both too busy any of our “parties,” but not once did we talk about it. Maybe about a week into our near nightly sessions, we were having a few beers before deciding to jerk together before bed. “What do you want to put on?” Mark asked me, referring to the porn selection. “I have an idea. Let me find something,” I replied. I took the remote and searched for my personal favorite video. It’s a girl who wants to be gangbanged and makes her boyfriend watch. In particular, she orders her boyfriend to “keep those cocks hard for me, Billy.” By the end of the video, the group is fucking both her and her boyfriend. By the time this scene came on, Mark and I were steadily stroking away. “Not bad, right?” I asked. “Fuck yea, this is hot!” Mark replied. It wasn’t long before the two of us were watching this Billy character being double-teamed while his fictional girlfriend cheered them on. Mark suddenly paused the video, turned to me, and said: “where is your lube? I need to try something.” “It’s in the top drawer of my dresser, why?” I replied. He got up and removed his shirt and went to my room completely naked. He returned with the lube and sat down on the couch beside me. “So you’re saying if I put a finger in my ass it’s gonna feel amazing, huh?” He said. I replied, “don’t take my word for it, but I’m gonna need that lube, too.” “Ok, so what do I do?” Mark asked. “Well, get your fingers nice and slick, relax your ass, and just slide one in. It can take a minute to loosen up, but don’t worry if it feels uncomfortable at first. Getting the right angle is the hardest part. Here, check it out,” I replied. I reached out my hand and Mark handed me the bottle. I squeezed some of the lube out onto my fingers and slouched low on the leather couch. I brought my knees up to my chest and with one hand gripping my cock, I reached past my cock and started rubbing the lube around my asshole. I then slowly began to push my index finger in and out, going a little deeper each time. I was sitting in the corner of the sectional sofa, angled toward Mark. Mark was watching intently, slowly stroking his hard dick up and down. This went on for a minute or two. “Now I think I can get a second finger in. Once you get two in, it starts to really feel good,” I said. Mark watched as I pushed two fingers into my ass. Mark grabbed the remote and resumed playing the video. He grabbed the lube and applied some to his hand and mirrored my position on the couch. He angled himself in the opposite corner. In this configuration, we could both see the screen as well as each other. Mark started to rub his ass slowly and within minutes we were both fingering ourselves and vigorously stroking our cocks. “Oh damn, this does feel pretty good!” Mark exclaimed. After a few minutes, his breathing became heavy, and as I looked over I saw that he was no longer stroking his dick, just holding onto it. Instead, he was focused more on sliding his fingers in and out of his ass. “You get now why I asked you to fuck me?” I asked. Mark chuckled, “yea, I think so.” There was a brief silence between us, the scene on the television continued, now Billy was being mercilessly gangbanged and Mark was sliding his fingers to the knuckle and back out again. “Can I fuck you?” I asked, flatly. There was another brief pause. Billy was moaning loudly with a cock in his mouth on the television. “Ok.” Mark replied. Without another word, I stood up. My cock was rock hard as I kneeled in front of Mark. He was already in the perfect position. With my head just inches away from his asshole, I poured a line of lube up my shaft, across his ass, and allowed some to pour over his cock. I set the bottle down and gripped my cock at the base. I pressed the head of my cock against his ass and started to push. It popped right in. Mark moaned softly as I slowly thrusted in and out. Mark was on his back, slouched against the arm of the sofa. I pulled him towards me and started thrusting deeper. He spread his legs wide, with one resting on the back of the couch, the other in the air, and soon he was taking my entire cock as started to fuck him. I had one knee bent on the couch, and my other foot planted on the floor. When I pushed in deep for the first time, Mark moaned loudly, “holy shit, oh my god, just go slow, oh my god.” He wasn’t even touching his dick, just holding up his leg with one hand and gripping the couch with the other. I could feel that I was going to cum soon. His cock was glistening with the lube, so I reached down and started stroking him. His eyes went wide and he looked from his cock to my eyes and back again. I pushed in as I deep as I could go and started jerking him furiously. Mark began moaning even louder, louder than most girls I had ever fucked. It was hot. His already hard cock got even harder in my hand and soon I felt it begin to pulse as Mark shot string after string of cum into the air. I held on tight and started to thrust my full length in and out of his ass. It was only moments before I could feel my cock building up to an orgasm. With one hand still on Mark’s cock, I pulled out of his ass at the last moment and used my other hand to masturbate. I don’t know what came over me, but Mark watched as I held the head of his cock in front of my own and shot several spurts of come across his cock. Before it ended, I lowered my shaft and slid it back into his ass, allowing the final drops of cum to flow inside of him, Mark rolled back his head and moaned when I did this. I pulled out, released his cock from my grip, and backed away. It was a sight I’ll never forget: Mark’s legs were spread wide, his cock plastered in our cum, as a final drop of my own cum escaped his asshole. I sat back on the couch. He pulled himself upright, we were both sweating. Though we had a few beers that night, we were definitely more sober for this encounter. “Holy fucking shit that was the hardest orgasm I’ve ever had!” Exclaimed Mark. “Yea, I told you,” I replied. We parted ways and got cleaned up before going to bed.

The next evening I had just made a dinner and was sitting at the table eating when Mark came home. He had some take-out food and joined me at the table for dinner. We greeted each other and exchanged some boring details about our day. I knew I was the more comfortable one with my sexuality, so I initiated something that had been on my mind all that day. “So about last night…” I said. Mark looked over at me and nodded, his mouth was full. “If you’re down to do that every now and then, so am I. I just don’t want it to get weird or anything. I mean, I really like it but at the same time I’m not gonna try and find some random guy off craigslist to try it with. You told me how good it was for you, too.” “Nah, I get it,” Mark replied. He paused to swallow his food and continued, “I’ve been thinking about it all day today, too. If it feels good for you and me, then fuck it. I’d just be jerking off anyway, and god damn did that feel good last night. Like, I don’t know if I’d rather fuck or be fucked.” “Alright cool. So, our little secret then?” I asked. “Sounds good to me,” replied Mark. ‘Was it weird that I jacked you off?” I asked flatly. “Eh…not really, I guess. I mean, your dick was already up my ass so it’s not like we were getting any more gay.” Mark laughed as he said the last part and adjusted his shorts. It was obvious this conversation had got him hard, I wasn’t exactly soft either. Just like every time we had hooked up before, my heart began racing. Ever since we started our little parties my mind had gone back to the time a mutual friend of ours had traded blowjobs with me. It wasn’t something I had really thought about since, but our recent antics had brought that memory back with perfect clarity. “Would you let me suck your dick?” Mark seemed to be in shock as I said this. I’ll admit, I was too. Of all the phrases I ever thought I’d mutter in my lifetime, this wasn’t one of them. I got out of chair kneeled to the floor before crawling in front of Mark’s chair. “Oh shit, um, ok,” Mark whispered. He unbuckled his belt and slipped his shorts and underwear down. His cock sprung from boxers and leaned to one side. He was as hard as he gets. I grasped his cock with one hand and immediately started sucking. Mark pulled up his shirt and leaned back in his chair, deeply exhaling. It had been years since I had done this. His cock filled my mouth. I tried my best to get it as far down my throat as I could, but couldn’t get more than about a third of it in, although Mark didn’t seem to mind. After a few minutes of steadily bobbing up and down, I pulled back and said, “I think you’re going to like this.” I started sucking the index finger of my other hand and rolled it across the saliva covering Mark’s cock. Then I put his cock back in my mouth and started circling my wet finger around his asshole. Mark responded by leaning back further and arching his ass up, giving me the green light. I pushed my finger in. I thrusted my finger back and forth before going all in. Once in, I felt for his prostate and started to flutter my finger against it. Within thirty seconds Mark was breathing heavy. His cock swelled and I felt the warmth of his cum pouring into my mouth. I pulled back so that just his head was resting in my lips. As the pulsing in his cock subsided, I let his cock fall from my mouth and somehow managed to swallow what felt like a cup of jizz. “Sorry, I don’t know why I felt the need to that,” I said. I took a sip of water to wash his cum down. “No, that is more than ok. How have I not met a girl that would do that?” Mark asked. “You just have to ask,” I said. “So is that how this’ll work now? If I need to get a nut off I can just ask you?” Mark said, with a wide grin. “Hey, don’t act like last night won’t be the last time I’m gonna fuck you!” I stated firmly. “Great, anytime I bend over I’m at risk of getting your cock in my ass then?” He chuckled. “Well, we’ve kind of been playing roulette with that one,” I said. “How so?” Mark asked. “Ok, so if I’m planning on doing anything with my ass, I always to try to clean it up a bit first. We’re both decently healthy, so I know that if I’ve taken a shit earlier in the day, it’ll more than likely be cleaned out. But most of the time, I use an enema. You can buy special douches but the enemas are pretty cheap.” I said. “So now we’re going to have to plan ahead to fuck each other?” Mark asked. This is where we set up some ground rules. ‘Grilling at the pool” became the code phrase when either of us texted the other about a possible session later in the night. We decided that we had to always let the other know if guests were expected and we also agreed to continue to keep it a secret.

This arrangement lasted for nearly two months and to this day I still don’t know what to make of it. Almost every day during this stretch would involve us hooking up. Two or three times a week I’d send or receive a text saying: ‘Go to the pool tonight to grill?’ Other nights were just masturbation sessions where more often than not he’d request a prostate massage, in either case, I was swallowing a load of his cum almost every night. I even got him to suck my dick a few times, although he never got into as much as I did. He wasn’t good at keeping my cum in his mouth and would complain about it in his beard. Mark mostly enjoyed fucking and getting fucked. Some of the best nights were when we went out drinking and would meet girls, only to come home and spend the night drunkenly taking turns fucking each other. However, it all went south when I met my current SO. Once we started dating I think Mark became rather resentful. It wasn’t long before we were fucking once a week, at best. When things got serious and I moved in with her, Mark started making demands about paying a full month’s rent for 3 days of my stuff being in his garage and that all these items I had bought around the house I had given to him and had no right to take. By the time I got him to agree to half the month’s rent, I was pretty resentful of him, too. That was the last I ever talked to him. On the plus side, I’ve never needed to look at porn again, I have a lifetime of quality spanking material saved up in my head.

If anyone has actually read any of this, I hope you enjoyed it!

Source: reddit.com/r/gonewildstories/comments/9tphgg/my_roommate_and_i_gradually_went_from_drinking