Catching My Roomate & Helping Him Cum

At around 3:00 in the morning, I woke up in the middle of my sleep having to go take a leak. I wiped my eyes so I could see better and shifted my legs to the side of the bed where I kept my pajamas on the floor. I slept nude most nights because I like feeling free of clothes at night and plus, my roommate and I respect each others personal spaces in our apartment together so I knew, anything less than a house fire, he wasn't going to see me. But I stood up quietly on the carpet floors and lifted my pajama pants to my hips. There was no need to put on a shirt since my roommate and I were both guys who didn't mind seeing the other shirtless. But then, I stepped out of my bedroom and began tiptoeing down the upstairs hall to the bathroom next to my room.

At the end of the hall past the bathroom door was my roommate's bedroom. His name was Greyson and he had his name carved into a small piece of wood mounted to his bedroom door which he made back in Boy Scouts growing up. It was one of the only things he still had from his childhood after getting kicked out from his family home for telling them he was bi. That's when he stayed over at my apartment and we just started living together. He knew I was gay but I didn't want to tell him what my feelings were, afraid he might like me back just because of his situation with his family almost two years ago. He was cute, but I got my mind off of him and honestly forgot he was cute after a while. We were just roommates now.

Greyson's bedroom door was open just a few inches but just enough that when I came out of my bedroom door, I saw his tv was on. And I listened for a second to realize, it was playing some YouTube show he loved to watch all the time in the living room as he ate dinner. It was a little loud but I just woke up so obviously I didn't mind the noise if I slept through it most of the night so far. I went into the bathroom, closed the door behind me and turned on the small light above the sink. Then, I slowly walked over to the toilet and lifted the seat. I unbuttoned my pajamas, reached my fingers through the slit in my boxers and pulled out my flacid cock by its mushroom tip. 

I held it at the top and bottom like it was a cigarette as I aimed it downward into the bowl below me. I began licking my lips back and forth with my tongue seeing that even when I have a bladder full of urine, I can never seem to start my stream otherwise. My piss started slowly filling my tubes inside, making its way to the exit and then I heard the water splashing as my stream began pouring into the bowl, making it turn bright yellow. With every passing second, my body felt more relieved to release so much liquid from inside. 

Once the stream turned into drips, I shook my cock up and down as another drop of piss splashed into the bowl below. I pushed my cock back into its cave, put the toilet seat back down, and quickly washed my hands before turning out the light and heading back into the hallway. I tippy toed on the carpet back to my bedroom so I wouldn't disturb Greyson. But as I was heading into the doorway to my bedroom, I heard Greyson's voice call out softly, "Fuck!"

Wanting to make sure he wasn't hurt or anything serious, I made my way to his door and looked inside. His bed was across the right side wall to where his bedroom door opened. His tv was on the wall straight ahead which was still playing his favorite internet show fairly loudly. But Greyson was on the bed with his face planted into the pillow and his ass up in the air, doggy style. He had his head turned to side, away from the door looking at his cell phone on his nightstand which was playing some gay porno he found online. He had his right hand turned behind his ass, plowing himself with a dildo to the same rhythm of the actors in the porn video. His left hand was positioned underneath him, slowly stroking his cock with plenty of lube, making every bit of his cock reflect the light of his television.

I stood there for a second, not wanting to look away. Greyson and I both knew we each had some sex toys of our own. Honestly, there were a few times where him or I forgot to take our dildos or fleshjacks out of the shower after cleaning them but we never mentioned it to each other. We were both just good friends and roommates. And we both didn't want to make things awkward. Plus, we both knew this was the first apartment we had since leaving our family's houses after college so both of us having some toys was completely understandable. So, the dildo in his ass didn't shock me in the slightest.

What surprised me was that his ass was shaven clean and it looked so smooth and easy for a cock to slide in and out of with no hair at all. In fact, it looked like a perfect meal to eat him out with my tongue. And his dildo was making its way in and out with such ease. But it was tough to keep looking at his smooth ass without getting distracted by his giant cock. The glare from the tv shimmered off of every centimeter of his almost 9 inch cock as his hand slowly made its way up and down the shaft, revealing either the front or back of his shaft with every stroke. His ball sack was hairy. Greyson didn't shave it like he shaved his ass. But it too shimmered against the light of the television across the room from the door I was peeking in from. 

And that's likely when I should have walked away, knowing his "Fuck" from before wasn't that he was hurt but rather that he was enjoying the night by himself. But I was mesmerized by how amazing his ass looked. A long time ago, I used to imagine what he would look like naked but now it didn't cross my mind anymore. And of course, he looked nothing like I imaged. His ass looked so much tastier and smoother than any of my daydreams back in the day when he was a friend who just needed a place to stay.

I just kept standing there as he fucked himself with his dildo and ever-so-slowly stroked his cock. He looked like he was edging himself, getting his cock to a point near explosion and then backing off, all of a sudden seeming to let go of his cock and just continue fucking himself with the dildo from behind him. 

I began to notice my growing problem inside of my boxers and pajama pants. My 8 inch member was almost at full salute and making my pajamas look like someone set up a tent in front of me. I didn't want to just walk away and take care of my cock in my bedroom like so many times before. I knew I should but I didn't want this opportunity to go to waste and I wanted to watch until the end. Plus, Greyson had his head in his pillow and turned away from me so he was never going to find out.

So, I reached my hand down and started groping my cock through my silk-like pajama pants. My eyes were fixated on his cock which seemed to shimmer more and more with every stroke of his hand from the amount of lube he applied to himself. I began licking my lips, imagining the taste of his ass on my tongue and soon enough, I slipped my hand into my pajamas and let my cock spring out into the open air so I could begin stoking myself. My cock was already hard as a rock so I knew it was only a matter of short strokes until it was ready to explode into my hand and I could go back to bed happy. 

I wrapped my fingers around my cock at the base and pulled the skin upwards towards the tip and then back down again. I tried my best imagining I was the one topping him as I tried to keep my strokes in rhythm of his dildo sliding in and out of Greyson's perfect twink ass. Besides a few soft moans, Greyson did a good job of keeping himself quiet. I guess he knows that I'm just down the hall and while we both know the other jacks off and has a dildo or two, we try to keep our fun times quiet to not disrupt the other. 

Greyson kept his dildo deep inside of his ass as he took both hands and did a push up, lifting his head from being buried in his pillow. He eventually stood on his knees atop his bed, facing his pillows away from the door. He reached his left hand around himself to hold the dildo as he slowly sat down on his own feet. Greyson began holding the dildo in place by tightly squeezing it between both of his feet as he sat up and sat down onto the dildo. He was riding cowboy on his own dildo on his bed. I tried to do it before myself but with nothing to suction cup my dildo onto, I was at a loss. But Greyson figured out how to do it. Not only that but he perfected it and he was a pro at it.

He fucked himself for a good five to ten minutes, all the while, he was edging his cock to the breaking point and I knew he wasn't long from shooting all over his sheets and pillows. I began stroking my cock faster and faster, staring at him through the 2 inch gap in the door. I thought he was about to shoot when suddenly, he plunged the didlo deep into his ass and flipped himself over. He laid down on his back with his head on his pillow before opening his mouth and sticking out his tongue, looking like he was going to try to catch his own cum on his tongue so he could taste it. He looked down at his cock but from the corner of his eyes, he saw his door was slightly cracked open and from the light of his television flashing, he could only slightly see me standing there.

He released his cock quickly and jumped up towards the door. I quickly ran to my room and closed the door behind me, hoping he would get in the hall and think he was just mistaken. I jumped into bed and got under the covers. I even turned on my side, away from the door so if he came in, he wouldn't see I was still hard under the blankets. I pretended to be asleep as I heard him open his door and walk into the hallway. Maybe he went back into his room, thinking he saw something that wasn't there. It was a few minutes until I took a breath of relief. 'That was scary as hell' I thought to myself as I was still hard as a rock. This was by far the most risky thing I ever did to jerk off and I realized I loved voyeurism which is the act of watching someone else have fun while you jerk off yourself without them knowing you're there. 

But I wasn't getting rid of my boner any time soon from trying to go back to sleep. So, I reached my hand down and began stroking it faster than before. I was hoping for a quick load onto my blankets and then fall asleep again soon after. But I heard my bedroom door open from behind me. 

Greyson walked into my room and I just held my cock still, as if I was asleep. He quickly made his way to the foot of my bed and tore the blankets from over me, revealing that I wasn't asleep and showcasing what I was holding. "Son of a bitch, Alex! That was you!" He screamed at me while he jumped on my bed, still nude. He manhandled and vastly overpowered me until his legs and feet were holding my legs firmly down and his hands were holding mine towards each of the upper corners of my bed. His face was inches away, glaring straight down at mine.

I knew he was furious with me and I felt like I was so tiny and powerless underneath him as he screamed at me telling me how his privacy mattered and I should never have betrayed our trust like that. But I knew how risky it was. I turned my head to the side so I wouldn't have to face him. I knew I fucked up big time so I knew what he was going to say. All I could say over and over was how sorry I was. 

"Alex look at me!" he yelled as I turned my head upright to see his face. "You don't understand Alex."

"No I do, I promise. I fucked up and I'm so sorry Greyson."

"No you don't Alex. That's why I came to you that night." he quickly pushed his hands forward, pushing my arms further into my bed before leaving them go and standing up.

"Wait, what do you mean that night?"..."What night?" I calmly asked him over and over as he walked out of my room and back into his bedroom. I followed him as he got to his bed and sat at the foot of it with the television now muted. "What night are you talking about?" I asked one more time from his doorway, now wide open.

"Remember that night I got kicked out and I came to you because you were the only gay friend I had?" Greyson said.

"Yeah, but I didn't know I was the only gay guy you knew at the time."

"Well, you're the one who had me confused for the longest time. I knew I liked girls but every time we hung out, I just kept wanting to reach down your pants and it confused me until I finally realized you were gay and thought maybe it was okay if I was too. So, that's why I turned to you after I was kicked out when they found out I liked you. I didn't come out to them, they just knew how I acted with you. And then when I moved in, I didn't want things to get weird but there was a part of me that did want things to go 'there' with us."

"Wow, I had no idea. I mean when you moved in, I wanted to tell you I had a crush but I didn't want to make you feel like you had to have a crush on me back in order to keep living at my apartment...so I pushed those feelings down and never thought about them until I overheard you jerking off tonight."

"Tell me, have you ever had a guy fuck you?" Greyson asked me.

"Yeah. You?" I replied.

"Yeah but there was never love there. It was a parking lot, late at night."

"Yeah...it sucks there wasn't love there but me too."

"So, where do we go from here?" Greyson calmly asked.

"I don't know but all I can say is we'll figure it out as we go. I can't hide it anymore and now that I know you..." Greyson pushed his hand over my mouth, stopping me from speaking.  

"Alex, do you mind me taking what I want right now?"

"No" I mumbled through his hand, still completely covering my mouth.

He pushed me back, further onto the bed and once again, used his overpowering strength to manhandle me into position where he was on top of me, holding me down and I was powerless underneath him. He held my arms and my legs in place with his raw strength and slowly bent his head down to kiss me. My lips glided across his like they were puzzle pieces, made to fit each other perfectly, side by side. I felt his tongue push its way into my mouth and mine was soon samba dancing with his. His hips were pushing his naked body and cock harder and harder onto my body, grinding against my cock. 

He pulled back his head above me and released my arms. He grabbed the pillow from above my head and picked my hips up with his strong hands to place the pillow underneath. He pulled off my boxers and pajamas with one swift motion and placed me back down onto the pillow. My ass was now at prime height for his cock to use. He lubed his cock with some bottle off his nightstand. He picked my feet up and placed them over his shoulders so there was no longer anything between his cock and my wide-open hole. He then placed his hard, mushroom tip against the pink ring of my ass. Greyson took his lubed-up hand and started playing with my cock and ball sack as he slowly drove his cock further and further into my hole. 

I began to moan loud, not having to care anymore if my roommate found out I had something up my ass and was enjoying it greatly. He pulled his cock out and pushed it back in harder, pile driving me into his submission. Faster and faster his cock pounded my ass. With every pound, my moans became increasingly loud. I knew I wanted him to do this to me for almost two years and I was going to make sure he knew this wasn't like the time I got fucked in a parking lot by a random stranger. He was pounding me as fast as his hips could move forward and back. Greyson took his large hand and covered my mouth once again so I couldn't moan anymore as his fucking suddenly slowed to a stop. I felt his cock expand and suddenly felt his massive load of warm liquid being shot deep inside of me.

He slid his cock out of my hole and released my mouth from the grasp of his strong hand. He began taking my legs and putting them back down on the bed and repositioned himself so his cock was right above my mouth. I opened my lips wide enough for his cock to enter and I scraped all the cum off of him as he pulled his cock out. He was now all clean, besides the sweat which was dripping from his hair and the sweat glistening off of his chest.

Greyson backed up so his cock was right above mine. He bent over and started kissing me with his tongue once again. In the middle of our beautiful kiss, his right hand began wrapping my cock below him, stroking it with the lube from earlier and precum which dripped out along the way. He stood on his knees and positioned my cock upright, directly in the path of his tasty hole. He sat down and in one smooth motion, I felt my cock penetrating deeper and deeper into his body. 

I reached my hands out to touch his knees beside me and feel his chest, wet with sweat, as he rode me as fast as he could. I thrusted my hips up and down to match his ride and we were perfectly in synch, like all good friendships are. My cock was having the time of his life feeling every inch inside of Greyson's tight hole. I was really giving it to him, as much as I could from below him. He predicted correctly that I loved to feel like I wasn't in control of anything in these moments but he knew I enjoyed it too much to not move my hips to fuck him harder. 

I stopped thrusting and began shooting load after cum load inside his hole. He kept riding me up and down, making the sensation much more intense and making me cum harder and faster. After my shots were all fired off, he bent down and we kissed once again. We kissed for quite some time, just him laying on top of me, making out. And I loved it. I had nowhere else in the world I would rather be than under him with his tongue in my mouth, letting me know I was his property now. Though our make-out session, my cum slowly dripped out from his ass onto my lower chest but I didn't mind being wet. I just kept kissing him until we were too tired to kiss any longer.

He got beside me on the bed and held me with one arm around my chest. "So, do I have to go back to my room now?" I asked him.

"Alex, you can stay here if you want. You don't have to go if you don't want to." He whispered in reply as he turned off the television and put his hand back over my chest, holding me in place, as if to tell me I wasn't going anywhere even if I wanted to.

I fell asleep quickly after, only now with a giant smile on my face and his sweaty and warm body skin-on-skin to my one side.

The next morning I woke up before him but with his hand still over my chest, I didn't have the heart to wake him. I just turned my head and watched him sleep for a while. Who knows how long I watched his eyelashes flutter and how many times he licked his lips with his tongue or how many tiny little snores his nose made or how many breaths of air I felt hit my shoulder. When he finally woke up, he saw me looking at him. "Are you staring at me again?" he whispered.

"Maybe. You're beautiful Grey."

"You really have a thing for watching people when they don't know it, don't you Alex? And what's with Grey instead of Greyson?"

"I don't know, nickname maybe. Don't you like it?" I replied.

"It's a nickname. I never had one before but I like it. Anyway, are you hungry for breakfast?"

"Yeah. Are you hungry for breakfast?"

"Starving after last night."

"Good" I replied as I turned over to kiss him. My right hand slowly made its way, softly gliding down his chest towards his cock. I kept kissing him as I wrapped my hand around his hairy cock and balls and played with them until he started growing harder and harder. I lifted my mouth from his and started kissing his neck and then chest.

"I thought you were hungry for breakfast, Alex? Not that I mind."

"This is breakfast for me. Then you can have whatever you want for yours." I replied to him between the kisses going down his chest. Eventually I came to his cock, standing 9 inches tall in front of me, towering above my eyes from this view. I circled the base of his cock with my tongue and began kissing and licking his hairy ball sack before licking the side of his shaft all the way up to the top. From the corner of my view, I could see him looking down at me with anticipation, knowing what was coming next. 

I kissed his mushroom head and swallowed all 9 inches deep into my throat from having no gag reflex. "Holy shit, you go deep." I heard him excitingly explain. I kept my lips tightly wrapped around his shaft as I sucked in air as hard as I could and made my way back to the top. I twisted my head slightly to one side, made my way back down all the way, then sucked on my way back up. I kept twisting my head, allowing him to feel a new sensation from a different angle each time as I played with his balls with my one hand and used my saliva as lube to wrap my hand in front of my lips and slide my hand up and down with my mouth, adding to the pleasure.

He tasted like every good...nope, I'm wrong. He tasted like every great cock does. There was still a little sweat taste on his shaft from last night and his cock tastes like nothing else I could describe or compare to. Cocks are like that, they have their own unique but incredible taste to them. And honestly, it was a taste I haven't had in a while but I loved the taste on him. So, I didn't mind that it was taking him a little bit to work up his cum. He edges himself and that's what edging trains you for, stamina to go for a while. But seeing that I love the taste, it was all the better for me.

On another trip down to have his cock deep in my throat, I felt his cock stiffen more than it was before and widen in girth slightly. I backed off, wanting for his cum to shoot into my mouth, not in the back of my throat where I couldn't taste it. He shot on the roof of my mouth and it was powerful. It felt like rockets of warm cum being thrusted inside the roof of my mouth. And the best part was, all his cum accumulated on my tongue, letting me taste his sweet cum for as long as I wanted. 

I backed my head up, slowly sliding his cock out of my mouth, cleaning it off on the way. But he placed both his hands on the back of my head and forced me back down on his cock. He wasn't letting me go until I swallowed his entire load. I guess he wanted to make sure I was full for breakfast. But after three big gulps, it was all warming my tummy and fuck, did it taste amazing! 

He let my head go and sure enough, Greyson didn't want a regular breakfast either. He saw my cock was hard and went straight for it with his mouth as soon as he was free from my head being on top of him. He devoured it like a hungry canine who waited all day for breakfast. I held onto his hair as I enjoyed his wet and soft touch of his lips quickly swallowing and slowly releasing my shaft. It didn't take me near as long. After all, I was pretty much hard as a stick before he even woke up. 

I shot a warm load deep into his throat as I heard him loudly gagging on my shaft and cum. He was swallowing it as I was shooting it but his gagging sound just made me more excited and made me cum an even larger load. He came up for air a few seconds after gulping down the last drop. 

After both of us took a moment to breath and have both of our cocks calm down from the excitement of the night, we decided to go to an actual restaurant for breakfast. Normally, a load of cum is filling but the exercise involved in fucking each direction last night and giving each other blowjobs this morning made us both starving for even more. So, he got dressed in his room and I began to get dressed in mine. But because I wanted to look good for him on our first day out together, I took a minute choosing a t-shirt when he came into my bedroom and started talking from behind me. "I think this will make a nice sized office for us...What do you think, Alex? My desk over here and yours over there on the far wall?" 

"Office? but then where am I going to sleep every night?" I replied, still picking a shirt out.

"My bed, silly. Now, pick a shirt, I'm starving."

"Okay, but I want to look nice for you."

"We're going to McDonalds. We don't smell good enough for anywhere fancier."

"You smell great, just the right amount of sweat."

"You're cute Alex, but we smell so McDonald's then we can come home and get a shower together so we can go somewhere else later."

"Wow. Shower together?"

"What? So, you're telling me you don't want to come home and jerk off thinking about last night? Why would I let you do that...and let you use your Fleshjack again or those crusty socks I always find in the laundry bin? No, the days of you having to do things by yourself are over, Alex. You're all mine now and I plan on using you in every room in the apartment, even our new office."