My Roommate's Older Brother

My Roommate’s Brother Likes Sleeping Naked

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“You don’t mind if I sleep naked, do you?”

Cruz asked the question like it was the most casual thing in the world as he hooked his thumbs into the waistband of his underwear and shoved them down his thick thighs. It was late on Saturday night and I was in the middle of pulling the sheets back on my bed when he said it. He had already made up his mind that he was sleeping in my bed tonight because apparently he hated sleeping alone in new places.

“Yeah, it is fine… I guess,” I replied, my voice coming out quieter than I wanted. I pulled my shirt over my head, stripped down to my underwear, and climbed into bed on my side, turning away from him so I faced the wall. My heart was already hammering against my ribs so hard I could feel it in my throat.

Cruz got in right behind me. The mattress dipped heavily under his weight. I felt the heat of his body before he even touched me, radiating off his skin like a furnace.

“You know how I hate wearing clothes,” he said with a low laugh as he settled in. “And it is you. You have already seen everything anyway.”

I lay there staring at the blank wall trying to process what was happening. Taylor’s older brother was now completely naked in my bed. This was the same guy who had jerked off in front of me while eating pizza on a Friday night, the same guy who had fed me his cum with his fingers, the same guy whose thick load I had swallowed on my knees just this morning. And now we were sharing a bed like it was normal. I was way past the denial stage. Whatever was going to happen tonight was going to happen. There was no point pretending anymore. My cock was already half hard again just from the thought of him lying naked behind me.

He lay on his back for a minute, the sheets rustling as he got comfortable. Then he rolled onto his side behind me, facing my back. His breath brushed warm against the back of my neck, sending a shiver down my spine.

“Back home I could never fall asleep without cuddling my girl,” he said quietly. “That is why sleeping alone feels so fucking weird right now.”

A strange little twist pulled in my chest. I was not sure if it was jealousy or curiosity or something else entirely. The idea of him cuddling someone else every night made my stomach feel weird.

“You have a girlfriend?” I asked softly, trying to keep my voice steady.

Cruz chuckled, the sound vibrating against my skin.

“Nah. We broke up a few days before I drove up here. She did not want to do long distance if I moved for the job. So now it is just me… and this weird empty feeling at night.”

He moved closer. One heavy, muscular arm slid over my waist and pulled me back against him. His thick cock, already half hard, pressed firmly against my ass through the thin fabric of my underwear. The heat of it made my breath catch in my throat. I could feel the weight of him, the way it throbbed slightly against me.

“You don’t have an issue with this, yeah?”

I hesitated for only a second before the words slipped out.

“Nah…Not really”

No more pretending I did not want this. I pushed my ass back against his cock, grinding slowly. His breathing got heavier instantly. He moved fully behind me, his massive chest pressing against my back, his thick thighs molding perfectly to the shape of my legs. His heavy cock nestled right between my ass cheeks, only my underwear separating us. I could feel every inch of him, hot and thick and starting to throb harder with every slow movement.

“Well, you walked off this morning, so I thought you were weirded out,” he murmured against the back of my neck, his stubble brushing my skin.

I frowned slightly. “Weirded out? When?”

“When you swallowed my load,” he said, his voice low and rough. “You did not even give me a chance to jerk you off.”

My mind spun. Jerk me off? He had actually wanted to touch me? All this time I thought I was just his convenient little outlet, but maybe he had been thinking about me too. The idea sent a fresh wave of heat through my body and made my cock twitch hard inside my underwear.

I reached down, took his hand that was resting on my waist, and slowly guided it to the front of my underwear. I pressed his rough palm against my aching bulge.

“Well… now you can return the favor.”

Cruz did not hesitate. His big, manly hand started stroking me over the fabric, slow and firm. At the same time he began grinding his cock against my ass in slow and lazy movements. His cock grew fully hard within seconds, and I could feel his precum starting to leak through my underwear from behind. Every few minutes he would push forward a little harder, pressing us even closer together until there was almost no space left between our bodies.

Then his hand slipped inside my underwear.

The second his rough fingers wrapped around my bare cock, I had to bite my lip to keep from moaning out loud. His grip was strong and confident, nothing like my own hand. The contrast between his thick construction-worker fingers and my smaller dick made my head spin. He stroked me slowly, thumb brushing over the leaking head, spreading my precum around while his own hard cock continued to grind between my cheeks.

“It’s not that different from stroking yourself,” he said casually, voice low in my ear.

I was breathing hard now. “What do you mean?”

“Jerking off a dude,” he replied simply.

I turned my head back to look at him, shocked. “Wait… is this your first time with a guy?”

Cruz looked straight into my eyes and nodded.

“Shit, you are way too comfortable for a straight guy’s first time,” I said, half laughing, half in disbelief.

Cruz laughed softly, his hand still slowly working my cock. “Maybe you just remind me of my girlfriend a little.” His hand slid out of my underwear and moved back, cupping my ass and giving it a firm squeeze through the fabric. “I have always jerked off side by side with the dudes in college, but this is the first time I have actually touched someone.”

I smiled, feeling a strange mix of nervousness and excitement bubbling inside me. The fact that this was new to him too somehow made everything feel even dirtier and more intense.

I got a little bolder and pushed my ass back against his hand again.

“Well… have you thought about doing more?”, I asked.

Cruz’s hand suddenly stopped squeezing my ass and he slowly pulled it out of my underwear completely.

“You mean…fucking you?”

“Yeah… I mean… if you want to,” I stammered, suddenly feeling extremely exposed as I stared at the wall again. “Like… only if you wanna try it.”

Silence filled the room. My heart was pounding so hard I could hear it in my ears. Had I just crossed the line? He was literally grinding his naked cock against my ass, but actually asking to get fucked felt like stepping into completely new territory.

After what felt like forever I turned my head back to look at him, nervous about whatever expression I would find on his face. My stomach was twisting in knots. Part of me was scared he would laugh and tell me I was crazy. But a bigger part of me was already buzzing with excitement at the thought that he might actually say yes. That this massive, straight, tatted construction worker lying naked behind me might really want to fuck me tonight. I could barely breathe as I waited for his answer.


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