My first time with another man by deano7

I took the bus over to his place. It was dark and raining lightly but I didn’t care. The mist from the rain was helping calm my nerves. After a minute of second guessing everything I finally texted that I was here. A few minutes later his tall, brooding figure greeted me. We exchanged an awkward handshake and I went inside. His apartment was small and I was immediately greeted by his bed. “This way,” he motioned me over to the next room in the open floor plan. He had an accent, it was European but I couldn’t tell where. There was a small couch and table and his laptop laid wide open. It was paused on a threesome video. “Water or wine?” He asked.

I accepted some water but thinking back, wine may have been better for my jitters. He disappeared into the kitchen as I took off my shoes and jacket. He returned with a bottle of water, turning on a small heater and dimming the lights. The glow from the laptop video illuminated us as he sat down next to me, my heart skipping a beat.

“You like?” He nodded to the blonde on her knees pleasing the two cocks she held in each hand.

I mumbled something in approval and we both stuck our hands in our pants, horny but still too shy to rush things. A few seconds later Leo dragged his pants and boxers down revealing his thick uncut cock, glistening from his precum. From our texts I had assumed that he was six inches like me, but as I snuck glances at his package, I knew it was at least 7.5 when hard.

Not wanting to lose my courage, I automatically followed his lead and tugged my sweatpants and briefs off. Instinctively, he placed his left leg over mine. He was hairy in a rugged kind of way and his average-athletic build stood out next to my lean slim figure. It was almost an out of body experience because the next thing that escaped my lips was “Can I?”

My hand reached over and began stroking his cock up and down. Leo leaned back, extending his arm over mine and began fondling my nipples. I don’t know what I expected from my first time jacking off with another guy, but this wasn’t it. The threesome played for about 20 more seconds before he got up. “Come on,” he said as he closed the laptop and walked over to his bed.

I sat there for a second, frozen. I was not prepared for this but my curiosity eventually won as I walked over to his bare body spread out on the bed. I laid down next to him, his pale body visible in the darkness. We began toying with each other’s nipples and as we both became fully erect again, our lips met. A wave of confusion, excitement and sensation went through my body as I tasted the minty breath strip that couldn’t mask the heavy cigarette taste underneath. Our tongues explored each other’s mouth and Leo began taking charge. Perhaps he had been in charge this whole time but I had only noticed when his warm, giant hands made its way down by back and onto my ass.

I shuddered. “I’ve never been with another man,” I whispered in his ear.

“Never?” He asked.

“No not even jerking off.”

“Have you ever had poppers?” I shook my head no. “It’s not a drug, I promise,” he began, each word drenched in his accent. “You just sniff like this.” He raised a tiny bottle to my nose and I trustingly inhaled.

Leo took two sniffs himself and placed the bottle down next to us. “Suck it,” he whispered to me. I knew what he meant. I knew what he wanted me to do. But I was nervous. I stared into his eyes as I made my way down to his cock. I already knew I was going to be terrible at it. Having no experience of giving a blow job, I wasn’t sure if my mouth could even take his dick.

I took a deep breath and began to blow him. He was so thick, I held the base with both hands as my mouth went down his shaft. He reached his hand to the back of my head and began fucking my mouth until I began to choke. My eyes sprang water as I tried to engulf every inch of him. I could hear his heavy breathing and I focused on that to get out of my own head.

He never offered to suck mine, and even though part of me wanted my cock in his mouth, I didn’t mind him being the aggressor, the masculine one for once. It felt nice to not be in control or making the decisions. Suddenly, his fingers plunged into my hole and I squirmed in pain. He offered me more poppers. My hole was tight and unfamiliar with anything going in it, but I couldn’t tell him to stop. This feeling of euphoria was new.

He flipped me over onto my back and pressed his hairy chest against mine. I could feel his cock throbbing at the base of my hole, anxiously waiting for a way in as my legs rested against his shoulders. He slowly pushed the tip into my tight, tan ass and every caution about using protection or saying stop flew out the window. He pushed even deeper but the pain was new and electric and I began to moan “I can’t”.

Have you ever wanted something so badly but was terrified at the same time? That was me, wanting to please him but anxious of the pain. He continued to push but my hands pushed against his broad arms in instinctive defense. I could feel the restraint in his body that begged to fuck me as he kissed me again. His dark beard tickled my chin as he aggressively nibbled on my lip.

He reached over the side of his bed and fumbled in the dark. He fingered my ass with lube this time before sticking a butt plug into my hole. As it began vibrating, I felt heightened arousal as I closed my eyes in pleasure. I could feel him watching me, probably half-amused and half-turned on by the show I was providing. After a few more minutes of butt play, I climbed on top of Leo and began kissing him passionately.

“You like kissing?” He asked in a telling sort of way.

I kissed on his ear and neck. “I like you,” I admitted to this tall handsome stranger, tracing his nipples with my fingers. He led my head over to his nipples, guiding me to suck on them and lick them.

I rose back up to his mouth, unable to get enough of his tongue exploring between my lips. “Cum on my chest,” he commanded. The butt plug had slipped out and I sat back against his cock, grazing against my ass. I began stroking myself, staring intently at him trying to memorize his face and this moment. Watching his dark black hair sweep to the side and his rugged hairy chest awaiting my load. His piercing eyes focused on me while his large hands wandered back to my ass.

It wasn’t long before I came all over him and even onto the bed. He reached out for a nearby towel and I helped him clean it up.

We began to kiss some more. Man, maybe I do have a thing for kissing. “Where are you from?” I finally asked.

“Italy,” he whispered to me. In one final attempt he flipped me over, head down on his bed and ass arched up. His cock toyed at the entrance of my hole before going in halfway. Fuck, it was still painful. Perhaps my ass just wasn’t ready, because I pleaded for him to stop. Like a perfect gentleman, no matter how much aggression and adrenaline had built up, he forced himself to stop and began to jerk off.

“I’m sorry,” I whispered, wanting so badly to give him all of me. He quietly came and wiped himself with the same towel I had cleaned up with. He kissed me again and began slapping my ass. I could tell he was used to getting what he wanted. I laid in his embrace wondering when would I see him to do this again…

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