u/Beginning_Plate1968

The First Time I Bottomed for a Twink

I posted part 1 of me topping this twink last week so if you didn’t read that go check it out if you’re interested!

A few weeks went by and James and I continued our relationship. Topping was pretty new to me and, as much as I enjoyed it, I really wanted to bottom. So one night I invited him over, told him I wanted to bottom, and he agreed.

James was bottom vers, but hadn’t actually topped before. He was a little nervous, but was excited to pleasure me. He had me lie on my stomach and placed both hands on my ass. He spread my cheeks apart and his tongue brushed over my hole. My muscles spasmed at the sensation and I let out a slight moan. This got a chuckle out of James and he smacked my cheek, hard. I flinched, buried my head in the pillows, and whimpered. He kept eating my hole and I was in complete bliss.

He kissed his way up my body, from my ass to my neck, sending shivers of pleasure through me. His kisses trailed up my neck and to my ear and whispered, “Get on your knees and suck my cock.”

I rolled over and he took my place. James lay on his back, hands behind his head. He looked so cocky and smug. This was a totally different side of James that I hadn’t seen before, but I liked how dominant he was acting. I got between his legs and kissed his thighs, his balls, and ran my tongue up his shaft to his head. I slapped it against my tongue and took him into my mouth. I was deep throating him when he grabbed the back of my head and began thrusting into my mouth. My eyes watered, but I stayed there like a good boy, letting him use my mouth however he wanted. He released the back of my head and I gasped for air, tears sliding down my cheeks.

“Come up here,” he said, patting his lap. I wiped my face on the back of my hand and sat in his lap. He got the lube and spread some on my hole and his cock. “Are you ready?” I nodded, anticipating a slow start. James’ had a six inch cock, but was particularly thick, especially his shaft beneath the head.

Suddenly, a wave of pain blasted through me as he slammed his entire cock into me. I gasped in complete shock. Pain radiated through my entire core and we stayed like that as it began to fade and my breathing became more steady. I opened my eyes and looked down at James. He was looking up at me with a smug look on his face. My hand shot out, grabbed his face, and I whispered “Don’t you ever fucking do that again.”

James didn’t say anything back. I grabbed both of his hands and pinned them over his head by the wrists. Once the pain faded, I slowly slid up and down his cock. He said, “Keep going, that feels amazing.” He bit his lower lip and moaned. I sped up and he matched my speed, thrusting up into me. His eyes were closed and I could tell he was close to finishing. Suddenly, I lifted up off of him and his eyes shot open. “Why did you stop?”

“I waited so long for this. You’re not finishing that quickly,” I responded. I released his hands and slid off of him. He motioned for me to lie on my back.

He grabbed me by the back of the knees and pushed my legs back, my hole exposed to him. I grabbed my legs and he released them. His fingers found my hole, his other hand on his cock. He pressed into me and reclaimed hold on my legs. He began taking deep, long thrusts into me and I was moaning immediately.

“I can’t hold out any longer. Your ass feels too good,” he said. He leaned down and kissed me. James sped up, pounding my ass until he came, flooding me with his huge load. He leaned back, with his cock still in me, and wrapped his hand around mine. He stroked my cock and I rocked my hips down onto his in time with his hand until I shot my load, coating my stomach and chest.

reddit.com
u/Beginning_Plate1968 — 2 days ago

The First Time I Bottomed for a Twink

I posted part 1 of me topping this twink last week so if you didn’t read that go check it out if you’re interested!

A few weeks went by and James and I continued our relationship. Topping was pretty new to me and, as much as I enjoyed it, I really wanted to bottom. So one night I invited him over, told him I wanted to bottom, and he agreed.

James was bottom vers, but hadn’t actually topped before. He was a little nervous, but was excited to pleasure me. He had me lie on my stomach and placed both hands on my ass. He spread my cheeks apart and his tongue brushed over my hole. My muscles spasmed at the sensation and I let out a slight moan. This got a chuckle out of James and he smacked my cheek, hard. I flinched, buried my head in the pillows, and whimpered. He kept eating my hole and I was in complete bliss.

He kissed his way up my body, from my ass to my neck, sending shivers of pleasure through me. His kisses trailed up my neck and to my ear and whispered, “Get on your knees and suck my cock.”

I rolled over and he took my place. James lay on his back, hands behind his head. He looked so cocky and smug. This was a totally different side of James that I hadn’t seen before, but I liked how dominant he was acting. I got between his legs and kissed his thighs, his balls, and ran my tongue up his shaft to his head. I slapped it against my tongue and took him into my mouth. I was deep throating him when he grabbed the back of my head and began thrusting into my mouth. My eyes watered, but I stayed there like a good boy, letting him use my mouth however he wanted. He released the back of my head and I gasped for air, tears sliding down my cheeks.

“Come up here,” he said, patting his lap. I wiped my face on the back of my hand and sat in his lap. He got the lube and spread some on my hole and his cock. “Are you ready?” I nodded, anticipating a slow start. James’ had a six inch cock, but was particularly thick, especially his shaft beneath the head.

Suddenly, a wave of pain blasted through me as he slammed his entire cock into me. I gasped in complete shock. Pain radiated through my entire core and we stayed like that as it began to fade and my breathing became more steady. I opened my eyes and looked down at James. He was looking up at me with a smug look on his face. My hand shot out, grabbed his face, and I whispered “Don’t you ever fucking do that again.”

James didn’t say anything back. I grabbed both of his hands and pinned them over his head by the wrists. Once the pain faded, I slowly slid up and down his cock. He said, “Keep going, that feels amazing.” He bit his lower lip and moaned. I sped up and he matched my speed, thrusting up into me. His eyes were closed and I could tell he was close to finishing. Suddenly, I lifted up off of him and his eyes shot open. “Why did you stop?”

“I waited so long for this. You’re not finishing that quickly,” I responded. I released his hands and slid off of him. He motioned for me to lie on my back.

He grabbed me by the back of the knees and pushed my legs back, my hole exposed to him. I grabbed my legs and he released them. His fingers found my hole, his other hand on his cock. He pressed into me and reclaimed hold on my legs. He began taking deep, long thrusts into me and I was moaning immediately.

“I can’t hold out any longer. Your ass feels too good,” he said. He leaned down and kissed me. James sped up, pounding my ass until he came, flooding me with his huge load. He leaned back, with his cock still in me, and wrapped his hand around mine. He stroked my cock and I rocked my hips down onto his in time with his hand until I shot my load, coating my stomach and chest.

reddit.com
u/Beginning_Plate1968 — 2 days ago

The First Time I Fucked a Twink

A few years ago, I was in college actively on Grindr, dating and hooking up with guys. Eventually, I started exclusively dating a 19 year old twink, James, who was a year younger than me. Normally I’d go for older guys and bears so it was different dating somebody like me. He looked way taller in his pictures than he was in person. He was actually shorter than me, maybe 5’7”, and I found it kind of endearing.

James still lived with his parents conveniently near my apartment so he’d come over pretty frequently. A few times, if his parents were out, I’d go to his house.

Most of my previous sexual encounters I’d mostly bottom, but by now considered myself bottom vers and I think James did too.

The first time we had sex he gave my cock so much attention that I wasn’t used to. Eventually, I grabbed his face and pulled him up to me. I kissed him and I could taste my own precum on his lips and tongue. He straddled my hips and my cock brushed against his hole. I knew he wanted to bottom, but I wasn’t ready to give him that yet.

I told him to spin around. I grabbed his hips and lowered his ass onto my face. Spreading his cheeks, I flicked my tongue over his hole. James’s body shuddered and I went in again, sliding my tongue over his hole. I pulled back and he asked “why did you stop?”

I replied, “Suck my cock.” He tried to move and I clamped my hands over his hips. He looked back at me and I placed one hand on his back, pushing slightly, while the other remained on his hip. He understood then and leaned over, sliding his mouth over my cock and I went back to his hole. I leaked so much precum from this. I’d done this many times before, but always from James’s position. I never realized how hot it would be eating somebody’s ass while they suck my cock.

James pulled back, spun around, and straddled my hips again. My wet cock slid against his wet hole and he kissed me again. James said “get the lube.” I reached over, grabbed the bottle, and opened it. He took it from me, squirted some into his hand, reached back, and slid his hand over my cock. He squirted more into his hand and rubbed it onto his hole. I took the bottle from him, poured a small amount onto my fingers, and set the bottle down. I reached under him and slid my fingers against his hole, eventually sliding a finger into him. I circled my fingertip against his prostate and a bead of precum dripped out of his cock onto my stomach. I grabbed his cock with my other hand and began to stroke it while I fingered his hole. Precum leaked freely then, making a small pool on my stomach. I slid my fingers through it and brought them to my mouth. James bit his lower lip and breathed out “please, fuck me.”

I slid my fingers out of him, lined my cock up with his hole, and pressed against him. My cock slid into him as his hole stretched around my cock. He breathed deeply as he sat all the way down and took a moment to allow his body to adjust. Soon after, he began rocking his hips. His cock leaked even more precum and slapped against my stomach. I gripped his cock and stroked him while he rode mine. He brushed my hand away and said “stop, I don’t want to cum yet.”

Eventually, James leaned down and said “pound my hole.” I reached around his back, grabbed his shoulders, and gave him what he wanted. He moaned loudly and begged for my load. My hips slammed into his until I finally came deep in his ass.

James sat up, my cock still in his cum filled hole, and began jerking his cock. James didn’t tell me he was a heavy shooter and I was shocked when the biggest load I’d seen shot out of him. His hole flexed around my sensitive cock. Cum sprayed out of him, hitting my face, the wall behind me, and pooling onto my chest and stomach. He laughed at the shocked look on my face, wiped the cum off my face, and put his fingers in my mouth. I licked the cum off and he leaned down and kissed me.

reddit.com
u/Beginning_Plate1968 — 10 days ago

The First Time I Fucked a Twink

A few years ago, I was in college actively on Grindr, dating and hooking up with guys. Eventually, I started exclusively dating a 19 year old twink, James, who was a year younger than me. Normally I’d go for older guys and bears so it was different dating somebody like me. He looked way taller in his pictures than he was in person. He was actually shorter than me, maybe 5’7”, and I found it kind of endearing.

James still lived with his parents conveniently near my apartment so he’d come over pretty frequently. A few times, if his parents were out, I’d go to his house.

Most of my previous sexual encounters I’d mostly bottom, but by now considered myself bottom vers and I think James did too.

The first time we had sex he gave my cock so much attention that I wasn’t used to. Eventually, I grabbed his face and pulled him up to me. I kissed him and I could taste my own precum on his lips and tongue. He straddled my hips and my cock brushed against his hole. I knew he wanted to bottom, but I wasn’t ready to give him that yet.

I told him to spin around. I grabbed his hips and lowered his ass onto my face. Spreading his cheeks, I flicked my tongue over his hole. James’s body shuddered and I went in again, sliding my tongue over his hole. I pulled back and he asked “why did you stop?”

I replied, “Suck my cock.” He tried to move and I clamped my hands over his hips. He looked back at me and I placed one hand on his back, pushing slightly, while the other remained on his hip. He understood then and leaned over, sliding his mouth over my cock and I went back to his hole. I leaked so much precum from this. I’d done this many times before, but always from James’s position. I never realized how hot it would be eating somebody’s ass while they suck my cock.

James pulled back, spun around, and straddled my hips again. My wet cock slid against his wet hole and he kissed me again. James said “get the lube.” I reached over, grabbed the bottle, and opened it. He took it from me, squirted some into his hand, reached back, and slid his hand over my cock. He squirted more into his hand and rubbed it onto his hole. I took the bottle from him, poured a small amount onto my fingers, and set the bottle down. I reached under him and slid my fingers against his hole, eventually sliding a finger into him. I circled my fingertip against his prostate and a bead of precum dripped out of his cock onto my stomach. I grabbed his cock with my other hand and began to stroke it while I fingered his hole. Precum leaked freely then, making a small pool on my stomach. I slid my fingers through it and brought them to my mouth. James bit his lower lip and breathed out “please, fuck me.”

I slid my fingers out of him, lined my cock up with his hole, and pressed against him. My cock slid into him as his hole stretched around my cock. He breathed deeply as he sat all the way down and took a moment to allow his body to adjust. Soon after, he began rocking his hips. His cock leaked even more precum and slapped against my stomach. I gripped his cock and stroked him while he rode mine. He brushed my hand away and said “stop, I don’t want to cum yet.”

Eventually, James leaned down and said “pound my hole.” I reached around his back, grabbed his shoulders, and gave him what he wanted. He moaned loudly and begged for my load. My hips slammed into his until I finally came deep in his ass.

James sat up, my cock still in his cum filled hole, and began jerking his cock. James didn’t tell me he was a heavy shooter and I was shocked when the biggest load I’d seen shot out of him. His hole flexed around my sensitive cock. Cum sprayed out of him, hitting my face, the wall behind me, and pooling onto my chest and stomach. He laughed at the shocked look on my face, wiped the cum off my face, and put his fingers in my mouth. I licked the cum off and he leaned down and kissed me.

reddit.com
u/Beginning_Plate1968 — 10 days ago