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Roommates to Bedmates

Category: Gay Male
11.06.2020
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I had just got back from work on a Friday. Brandon was already back at our apartment. He hugged me once I walked in. Since we’re just room mates, I wasn’t comfortable with it at first, but over time I got used to it. It’s not much of a big deal for me anymore. It’s sort of the kind of guy he is. We got along pretty well and had been living together for about five months now.

Sometimes we’d do shots together and have fun and laugh. Occasionally on Fridays he’d convince me to play strip poker with him. It’s gotten to be almost an expected part of the week. I pretty much always lose everything, but he wasn’t the type to try to look at me naked so it wasn’t too bad. Both of us are straight and although I wasn’t comfortable at first, he helped me to get used to it a little more. I may not have liked the method of course. He had been on some sports team during high school so seeing a naked guy meant nothing to him. One night a few months back, while we were playing strip poker, he started losing a lot. I was able to keep on just my boxers and pants, but he lost it all. He didn’t show any discomfort with standing in front of me and pulling down his boxers. He wasn’t hard so I couldn’t really say how big he’d be, but I imagine it was more than me. He’s six feet, but I’m only five foot six. He stood there a moment before sitting back down. I couldn’t help but look at his uncut cock. I tried not for it too seem obvious, but from what I could tell he didn’t notice at all. After then we just played some hands for fun, nothing won or lost. I lost a little more after then. I still considered myself a straight guy but I couldn’t help but have some thoughts.

But anyway, that’s the past, and today’s today. We’d each had our dinner before coming back like we normally do on Fridays. He likes us to get started earlier now. We just play until one of us is naked and then stop betting.

“How about a little change Brian,” he said to me, “Let’s do a few hands for shots?”

“Do I drink if I win or if I lose?”

“Lose of course.”

“Sure, why not,” I replied with a slight grin while sitting down. It didn’t take long before I’d lost a small handful of hands, and him losing only two. I knew it’d be harder to stay focused on the cards tonight.

“You look like you’ve had enough for now. On to the strip?” he asked me.

“Yeah, I think I’m done with shots for the night.”

The first two hands I lost right away, both of my socks. I shouldn’t have lost so easily on those two, but maybe the vodka was kicking in a little bit. I won the next out of pure luck. Aces over kings, dealt from the deck, and nothing but luck. He slipped off his shirt revealing his toned chest. He wasn’t bulky but by no means was he tiny. If it were a wrestling match I’d never have a chance against him. In short order the rest of my clothes were off, and I couldn’t consider myself sober any longer.

“One more hand, just one more,” I said to Brandon.

He looked at me, knowing I was sitting there nude, but dealt anyway. “One last one to wager on.”

I had a eight high, and didn’t do any better on the draw. He beat me with a full house easily.

“Wait, I don’t have anything else on,” I said to him, wondering how I had missed being naked.

“Well a bet’s a bet, you have to take something off.”

“I don’t have any clothes on though.”

“So maybe take off a little hair?” He said with a wry grin.

“You aren’t shaving my head!”

“I was thinking lower, make you a little more naked. After all, a bet is a bet. Now you have to take something off.”

“I’m not shaving down there!”

“How about if you just trim? That wouldn’t be too bad. A good reminder for you too.”

“I’m still not doing that to myself.”

“Fine, I’ll do it to you. You can let me or I can force you but you made the bet.”

I don’t know if it was the vodka or what, but he got a pair of scissors and knelt in front of me. It was the first time I was sure he had seen my cock. He’d he plenty of chances in the past but now he would, and up close.

“Don’t worry I won’t hurt you,” he said to me as I closed my eyes and leaned back. He ran his fingers through the hair and began slowly trimming it away. Even though my eyes were closed, he seemed to be careful not to touch my cock. But with the stimulation of his hands, I knew I had my cock erect and in his face. “There, that’s not so bad,” he said to me once he was done, gently brushing away whatever loose hairs were left. I looked down at my erect cock, which seemed bigger than it had been before, and right in his face, before looking away, suddenly realizing I’d just had my room mate kneeling in front of my while I was naked. He got up and went back to his chair, and dealt out another hand. “No more wagers, just for fun,” he said to me. My luck didn’t improve any but it wouldn’t hurt my pride any more now. Eventually I just gave up, and went to sit on the love seat, in my spot on the right, in front of the TV. He joined me as usual, since there wasn’t many other places to sit to watch TV.

“You know what, since you were such a good sport about it, I’ll meet you, well, sort of half way, ok?” he said to me.

“Huh, what do you mean?” I replied.

“Just so you don’t feel so bad, I’ll strip too, ok?”

I don’t know what it was. Nothing told me to say no. I just shrugged and said, “Go ahead.”

He stood right in front of me. He didn’t block the TV, but there would be no way to watch the TV and not see his body as he slowly undressed, or at least he seemed to slowly undress. There was that body that I had only seen once before. With his short black hair, blue eyes, and toned body he just seemed to halt in time. I couldn’t help but look him up and down, and having my eyes stop halfway at his firm but not hard cock, not to mention untrimmed hair unlike me now. He sat back down as if nothing at all had happened. We were both straight, and when he had moved in he even had a girlfriend. There was nothing at all there to really give me any other idea.

We sat there and watched a movie. I can’t recall what it was. My mind had been thinking too much about him, and occasionally my eyes wandering over too him as discretely as I could, which isn’t easy when drunk. I could only wish for chaste thoughts, but that would have been completely futile.

“It’s getting late, and I think I should be going to bed now,” I said to him.

“Alright, good night Brian.”

“Good night,” I replied as I tried to get up. Immediately upon standing, I fell down and landed onto Brandon’s lap. Without hesitation he wrapped his left arm around my shoulders, and his right hand on my hip, holding me closely so I wouldn’t fall. I felt his cock slowly rising against my butt. I had to ignore it. It’s something easiest to just ignore after all.

“Are you alright,” he asked.

“Yeah…I’m fine…” I tried to get up a little, but he held me tight still. “I just need to get to bed, that’s all.”

“Let me help you, because I don’t think you can make it on your own.” He didn’t seem to wait for me to answer, before standing us both up, and him keeping his arm around my slender waist to support me.

“Thanks…I think the last thing I’d want to do is crawl,” I said with a light chuckle. Once we got to my bed, I ended up pulling us both down onto the bed. He ended up in the middle of the bed, with me on one side, and the sheets on the other. “Good night, Brandon, time for you to go to bed,” I said one last time before pulling the sheets over both of us, and curling up and quickly falling asleep.

* * *

When I awoke in the morning, Brandon was behind me, curled up with me. His left hand was over my stomach, his hand covering my belly button. I could feel his firm morning cock against my butt. I lifted up my head, and looked behind me to make sure it at least wasn’t some random stranger. His eyes were still closed as I laid my head back down, still too tired to try to get up. Then I felt his fingers tap against my stomach in rapid succession. Now I knew he was awake, and he knew I was. Neither of us moved or said a word. Here I was, a straight guy, who just woke up naked, with a naked guy holding me. I had no idea what to think. I slowly moved my hand down onto his, not moving his away, but only resting on it.

“Good morning,” he said to me.

“Good morning,” I replied, not looking back at him.

“Do you remember last night?”

“Yeah…at least I hope I do…we didn’t….you know…?”

“No, you know I’m not the kind of person to do that. I just wanted to make sure you’d be safe through the night. Want me to go now?”

“Thanks…and….it’s alright.” I don’t know what made me say it. It was really unusual. It’s almost as if I didn’t really say them. But he pulled me just faintly closer to him.

“I know it’s probably not the best time, but I figure the best time was a little while ago. I don’t really know how to say it except to just say it.”

I paused for a second without doing a thing besides closing my eyes. After waking up naked to your room mate, what could possibly be new information to be told.

“It’s just that…I’m gay. So if you want me to go, I will, and there’s no need for you to feel bad about it.”

I didn’t know what to say. Now I just learned I didn’t have a somewhat affectionate room mate, but a naked gay man behind me with his cock against my butt.

“Alright, I’ll go. Good bye, Brian.”

I clenched his hand tightly before he could start to get up to leave. To this day I don’t know what made me do it.

“Don’t, at least, not this moment….”

“So you’re not mad?”

“I’m….tired….and….thinking.” I didn’t know what I was thinking. I just liked the feel of him with me.

“About?”

Now I had to find an answer. What answer could there be? I’d never so much as considered myself bisexual let alone gay. “What to do really… To be a hundred percent honest, I’d be lying if I were to say I’d never thought about you in a way more than just a friend. But I never thought of the possibility of anything ever happening.”

His fingers began to slowly stroke my stomach. He didn’t say a word, and only listened.

“I’d never even hugged a guy until you. My luck with girls is marginally better. But here I am, my room mate’s cock against my butt, and I do consider myself straight, and I haven’t made you leave my bed yet.”

He backed away a little so his cock wasn’t touching me anymore, but didn’t say a word.

“It’s ok… I…didn’t mind to be honest… I don’t know why. Hold me tightly?”

With that, he moved against me again, putting his forearm on my chest and holding me firmly against him, his legs curled up against me, and used his right hand to gently stroke my hair.

I paused for a few moments, enjoying his warmth. “This is all so much and so fast… Can you give me some time?” I said. He kissed my cheek and got off on the other side of the bed. Before leaving the room, he turned to me, with my eyes staring straight ahead at his now flaccid uncut cock. He only paused, and left.

* * *

I didn’t move from my bed until late in the afternoon. I heard him in the shower and making lunch. I got out of bed, and got dressed, skipping a shower. I opened my door and our eyes met. Neither of us spoke at first. “Cheeseburger, Brian?” he said to me.

“Yeah, sure.” He often made me lunch so this was no surprise. I sat down, looking at the counter, not saying a word. I didn’t know what to say. It seemed as though we would just ignore it for the time being. He put my lunch in front of me, and left for the love seat. “Thanks,” I told him quietly. He didn’t answer, but may not have heard me. I must have taken half an hour to eat that one cheese burger. I listened to the TV in the background. My mind was lost on Brandon. What else could I think about? I slowly moved and sat next to him. He seemed to act like normal, while I was sitting there thinking of him. A man who 24 hours ago was my room mate, now it was all so confusing.

The hours quickly passed. Maybe it was slowly, but I don’t know. It’s an odd feeling, wanting to kiss the person sitting right next to you, and at the same time almost being repulsed by the idea. I didn’t just want to kiss him. Part of me wanted him to make love to me.

“What do you want for dinner?” he asked me. I didn’t reply, I barely heard him. “Brian?”

“Huh, what?”

“Dinner?”

“Oh, I’m not hungry. Too much on my mind I guess.” I just shrugged it off. He would know I was thinking about him, but knew to let me think. He ordered a pizza, and when it arrived put a couple slices on a plate and put it on my lap. I was looking down at the floor the whole time, still lost in my thoughts. I wasn’t hungry, at least didn’t feel hungry. He sat next to me, eating the rest of the pizza. I put one of the slices back onto the pizza box on his lap, and slowly started eating the other. “Are you alright?” he asked me.

“Yeah…I’m fine….don’t worry…”

I ate dinner even slower than I ate lunch. After the hours had passed, I looked at the clock, ten o’clock. We normally both stayed up until midnight. I wasn’t tired at all. I had too many thoughts to keep me awake. I put my plate in the kitchen sink and stood besides the love seat, watching the TV. Now would be the best time to decide what to do, I thought. I closed my eyes, and said “Your bed room or mine?”

He looked at me, at my closed eyes, and asked, “What do you mean?”

“If it’s alright anyway, should we sleep in yours or mine?”

He stood up, and moved in front of me before taking my hands in his. I opened my eyes to gaze into his soft blue eyes. “Tired?”

“In a couple hours…but I want to go now…”

“Ok, mine then…” he said before turning off the TV, putting his arm loosely around my waist and walking me to his bed room. I walked in front of him, and once I reached the bed, quickly undressed all but my boxers. As I was going to get into his bed, and wrapped both arms around my waist and pulled me back into him. “Are you sure?” he said softly.

“Want me to take them off too?” I knew it wasn’t the question he meant, but knew it would give the answer. I told him how to answer by putting his index fingers on the inside of my boxers at my hips. He slowly pushed them down until gravity pulled them to the ground. I stepped out of them and stood there, closing my eyes. I heard him undress behind me. I felt his arms encircle my chest, and his hips against me from behind. He was still six inches taller and made me feel so secure. I’d lived with him five months and knew I could trust him. He turned me around, and I looked up at him.

“Have you ever been with another guy at all before?” I asked him.

“Before my last girlfriend I was….yes… Have you?”

“Like I said, you’re the first guy I’ve even ever hugged.” I closed my eyes timidly, half embarressed. His left hand slowly raised to my chin, tilting my head back, as his right hand reached behind and cupped my butt. I opened my eyes to gaze into his once again, parting my lips ever so faintly as he kissed my so softly. I wrapped my arms around him tightly, as he held me even tighter.

“Let’s get into bed, dear, ok?” he asked me softly. Before I could answer, or knowing I wouldn’t utter a word, he swept me up and laid me in the middle of the bed. I turned onto my side as he curled up behind me, pressing his body fully against me. I nestled my body against him, ensuring that I could not ignore his manliness against me. He held me tightly, protecting me from what, I did not know.

“Are you still straight?” he asked quietly.

“I doubt it… Kind of hard to have a boyfriend and be straight, right?” I knew calling him a boyfriend would catch him off guard. Nothing of the sort had come up. He only held me closer, and whispered in my ear, “right.”

“I don’t know what to say, Brandon. All so fast, so helplessly spiraling out of control.”

“I’m in control though, so don’t you worry. I’m here to help you.” He squeezed me tightly, but not tightly enough for me to turn around quickly and hug his firm warm body tightly, our bodies aligned as much as our difference in height would permit. “Don’t you worry, dear,” he softly said.

“I trust you, after all, you haven’t made one obscene gesture to me yet.” He kissed me softly again. I merely relaxed, parting my lips, as his tongue pushed through my lips. I was helpless in my ecstasy of being with him.

“Don’t you worry, Brian, you’re my best friend, and I guess now my boyfriend. I wouldn’t want to offend you at all.” he said to me.

I looked straight into his eyes, and told him, “you will not.” I turned back around, and whispered, “but for the moment, hold me.” He didn’t hesitate before curling up closely with me, his now firmer cock against me. I enjoyed his warmth, his being. “So…” I said, attempting to force a conversation.

“Curious about anything?” he replied.

“I don’t know… This is all really new for me…so I’m somewhat lost in it all, like what to do.”

He chuckled lightly, causing my to curl slightly tighter, which would be obvious to him with him so closely against me. “No, it’s ok. You’ll learn, if you want that is. If you don’t want to, we won’t.”

I turned my head and looked back at him… I had always been somewhat naive about sex. I had only known there were gay men, not what gay men did. I was always too embarressed to find out more. “Making love,” I said to him softly.

He smiled softly, with a charm and made me melt more than I had already. “Well, generally there’s a guy called the top, and one called the bottom. The top…well think of it like a man and a woman having sex. The top is like the man. The bottom is like the woman, but instead of a pussy, he uses his, well his butt.” I looked away, slightly surprised. I mean, sure, I liked the feeling of his cock against my butt, the more it was pressed against it the better. But the thought of it in my butt, I was shocked. “It can be very pleasurable for both.”

“Yeah….or else they wouldn’t do it, right?”

“Right,” he said softly. His hand slowly moved to my butt, softly caressing it. “You know I wouldn’t want to hurt you.”

“So I guess you want to be the top?” I asked meekly.

“If you want to, you certainly can.”

“No, no…it’s quite alright… I….” I trailed off, too embarressed to finish my thought.

“Go on, said it babe,” he pushed on.

“I kind of like your cock against me…and want to feel you in me.” I quickly pulled the covers over my head to hide. He hugged me as tightly as he could, making sure his cock would be touching my butt firmly.

“I want to cum inside your cute little body, Brian. I want you to feel me as no man ever has.”

I pulled the covers down slightly, brushing back my somewhat long hair, and looked at him. “I thought you said you had…”

He interrupted, “not as a top…so you will be my first, sweet heart.”

I kissed him quickly, and turned to face him completely, and looked down at his cock. “It looks bigger now…”

“Yes darling, but don’t you worry. Don’t worry at all.” He got up and out of the bed, and I could see just how big it was. It was seven inches long, and thicker than mine was too. It was the first time I had really seen his hard cock that big. Without a thought in my head, I leaned quickly forward and took his head in my mouth. I instantly stopped, and looked up at him, as if for approval almost. He smiled softly, and stroked my hair. “It doesn’t take long for you, does it?”

I slid the head out of my mouth, and looked down at the floor. “I guess now…” Before he could give me any reassurance, and kissed and started licking the head of his cock, knowing it would soon fill me up inside.

He cupped my cheek and gently pushed my head away while smiling at me. “You are too cute, Brian, you know that?” I blushed slightly, half amazed at what I had done. In his hand was a condom and something called KY jelly.

“What’s that for?”

“Well the condom’s just for safety…and this stuff’s so it won’t hurt your cute little butt. I want you to enjoy our first time.” With that I got on my hands and knees on the bed, and looked over at him, smiling.

“I want you to enjoy it, Brandon.”

“Not like that… Lay on your back.” I laid on my back and looked at him, not knowing what he would do. He moved his right hand between my legs and spread them before kneeling in front of me. I looked up at him, the man who would be the first to take me. “Lift up your legs sweetie,” he said calmly, putting some jelly on his fingers. I lifted my legs, and closed my eyes as he put the jelly on my little butt hole. Knowing those were his hands and what he was about to do made me let out a small moan, at least until I heard myself and stopped, and smiled at him.

“Is that all, now?” I asked quietly.

“No babe, not quite ready,” he said, and slid his index finger into me as I let out a small gasp. He rubbed the inside of my, pushing inside my butt hole from side to side. He pulled out his finger, and I let out a small sigh.

“Now?” I inquired.

“Almost. Two this time, ok?”

I smiled to him, and lifted my legs a little more. He lubed up his index and middle finger, and slowly pushed both inside me deeply.

“It hurts, stop!” I cried out. He didn’t stop, and gently rubbed me until a was calm and it no longer hurt.

“Trust me sweetie, it’ll hurt a little at first, but you will love it.” I couldn’t help but trust him now. I had gone too far to want to turn back entirely. He slid his fingers out, and looked at me. “Now it’s time, just breath slowly.”

I slowly took deep breaths as he rolled the condom onto his long hard cock, and lifted my hips. I closed my eyes as he placed the tip of his cock against my virgin butt hole. He gently pushed forward, until the head was in and I opened my eyes as wide as I could.

“It hurts, no more!”

“Ok sweetie, I’ll hold it, just breath, relax.” He gently rubbed my butt with the head of his cock in my. I slowly breathed until it no longer hurt, and looked at him.

“Cover my mouth, and all the way, and hold it?” I begged.

“If you wish, I will.” With that, and covered my mouth and I closed my eyes, and he slowly drove all seven inches of his cock into my body. I tightly latched my legs around his thighs, not letting him leave me, breathing deeply in the hope the pain would leave me, so only the pleasure from him would exist in me.

“Brandon, it….feels so good but painful…” I uttered. He kissed me softly, and smiled.

“Want me to start moving in and out?” he asked. I only nodded, and released my legs from his thighs so he could. Very slowly at first, and only about half an inch he fucked me. I grabbed the sheets on the bed out of pleasure. He felt so wonderful inside of me, a pleasure neither of us had quite experienced before.

“It’s too much, wait, I want to enjoy it longer,” I said, writhing in pleasure. He silenced me with a deep, long, passionate kiss, never ceasing from his thrusting, and only going faster and with deeper strokes.

I cringed as I came between our bodies. Never before had I felt such pleasure, such pure ecstasy. He buried himself deeply into me, and looked down into my eyes just as my orgasm was subsiding. He took his hand, and dipped a finger into my cum and licked his finger clean. He then used his fingers to clean off my stomach, all the while his cock deep in me. I closed my eyes, knowing now that my pleasure was not over with a simple orgasm. He suddenly kissed me with such fury that I could not resist. I felt my own cum drift into my mouth as he started to pump his cock deep into me, deeper than had brought me to come. I was beginning to become delirious in the ecstasy from this man, my room mate, who shortly before was a straight man to me and nothing more. Here I laid with his cock thrusting deeply into me, and our tongues sharing my cum.

I writhed as the pleasure did not cease, and with the strength of his thrusts, so did the pleasure. A pleasure stronger than my orgasm overcame me, and I was helpless with him. I could not stop him, and the look on his face told me he was no longer in control, that his fury was pure instinct to come in me.

He slowed his pace, and looked into my eyes. “You trust me?” he asked softly.

“Yes, oh yes I trust you. Come in me, fuck me until you come!”

He pulled out of me entirely, and looked down at me. He removed the condom and didn’t hesitate to thrust his entire cock deeply into me. “I want to fill you with my cum, sweetheart.” I looked up at him, and only said, “Come in me.”

He needed no more encouragement to begin thrusting in and out of me harder than before. I pulled the sheets so hard out of ecstasy that they began to rip apart. His long thick cock was driving me insane with pleasure.

With one massive thrust, he forced his cock deep into me. I looked at his face, and could feel his cock pulsating inside of me. I wrapped my legs around him tightly, holding him.

He left his cock in me, as his orgasm became subdued. It must have lasted several minutes, by the look on his face, and the increasing gooey warmth in me. He collapsed on top of me, and I held him tightly. His cock slowly softened and came out, his come leaking out of me. I kissed his cheek, and smiled at him, and whispered in his ear, “you’re still in me.”

The sweat was beading all over his face. I rolled him next to me, and wiped his face dry.

“That was amazing,” he whispered to me, gasping for breath.

“Absolutely….exhausting too,” I added, before turning on my side, and putting his hand over my belly button, holding me tightly, safely. We drifted off to sleep together, the same way we had awoken.

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