Enhanced by AI.
----
I'd been running my mouth about my latest hookups when Jackson leaned back in his chair, beer bottle dangling from thick fingers. The conversation had gotten explicit fast: Jimmy on the baseball field, the couple from the club who'd invited me home. Everyone at the table was sharing war stories.
"Not bad," Jackson said, that half-smile playing at his mouth. "They sure sound like fun."
Jackson was nice but quieter than our mutual friends, but he had this presence — broad shoulders, forearms covered in intricate tattoos, the kind of guy who looked like he could pin you down without breaking a sweat.
Three days later, my phone buzzed while I was eating cereal.
*Been thinking about that conversation. You seem like you know how to have a good time. Want to grab beers at mine tonight? Fair warning — I like it rough.*
I stared at the text for a full minute. Jackson was trans, I knew that much from our friends. But the way he'd been looking at me during that conversation, like he was sizing me up...
*Never been with a trans guy before,* I typed back.
*Cool. We can talk it over. Maybe wrestle a little if you're up for it.*
My dick twitched at that. *Yeah. I'm up for it.*
His apartment smelled like cedar and coffee. Jackson handed me a cold bottle, our fingers brushing. He was wearing jeans, a hoodie and his hat.
"So," he said, settling onto the couch beside me. "What's got you uncertain?"
I took a long pull of beer, buying time. "I don't want to fuck up. Don't want to say the wrong thing or... I don't know, treat you like some experiment."
"Appreciate that." Jackson's knee knocked against mine. "But I wouldn't have asked you over if I thought you were an asshole. And honestly? The fact that you're nervous is kind of hot."
The beer was working its way through my system, loosening the knot in my chest. "You mentioned wrestling.", I said trying to sound a little more sure of myself.
Jackson's grin was pure predator. "Yeah. You game?"
We pushed the coffee table aside, cleared space on the living room rug and he took off the hoody. I'd expected maybe some playful grappling, but Jackson moved like he knew exactly what he was doing. Within seconds, he had me on my back, his weight pinning me down.
"Jesus," I breathed. His thighs bracketed my hips, hands locked around my wrists. The heat of his body pressed against mine, and I could feel every inch of muscle definition through his shirt.
"You like that?" His voice had dropped lower, rougher. When I nodded, he shifted his grip, one hand sliding down to rest against my chest. I could feel my heartbeat hammering under his palm.
That's when I felt it — the soft hair of his treasure trail brushing my stomach as he leaned closer. My cock was already half-hard, but feeling that intimate touch, knowing how strong he was, how easily he controlled my movement, made blood rush south fast.
Jackson noticed immediately. His eyes flicked down to where my sweatpants were tenting, and his smile turned wicked. "Well, look at that." He was able to carry me to the bedroom.
Before I could respond, he'd hooked his thumbs in my waistband and pulled my sweats down. My cock sprang free, and Jackson made a sound of appreciation low in his throat.
"Nice," he murmured, then wrapped his mouth around me without warning. He worked me with his tongue, taking me deep, his hands gripping my thighs to keep me still. When I tried to thrust up, he pressed down harder, reminding me who was in control.
"Fuck, Jackson—" I gasped, tangling my fingers in his hair.
He pulled off with a wet sound, looking up at me with dark eyes. "Your turn."
I fumbled with his boxers, hands shaking slightly from arousal and anticipation. When I got them down, I palmed his ass, squeezing the firm muscle. Jackson groaned and pressed closer, his bare chest against mine now. His skin was hot and solid, dusted with coarse hair that tickled my nipples.
"Touch me," he said, guiding my hand between his legs.
My fingers found wetness, heat, the soft folds of his pussy. Jackson was already soaked, and when I stroked tentatively, he rocked against my hand.
"More," he commanded, and I obeyed, working my fingers deeper. He was tight and slick, clenching around me as I explored. The sounds he made were pure sex — low growls and breathy moans that made my cock throb.
"Need to be inside you," I managed.
Jackson reached down, positioning my cock at his entrance. The first touch of my head against his wet heat nearly undid me. He lowered himself just enough to take my tip, and the sensation was incredible — soft and hot and gripping.
"Please," I begged, not caring how desperate I sounded.
He sank down slowly, taking me inch by inch until I was buried completely. Jackson's internal muscles clenched around me as he began to move, riding me with increasing urgency.
"Your ass," I gasped when he paused, both of us breathing hard. "Want to fuck your ass."
Jackson's eyes lit up. He pulled off me, turning around and presenting himself on hands and knees. When I pressed against his tight entrance, he pushed back, taking me deep in one smooth motion.
The sensation was overwhelming — the grip of his ass around my cock, the sight of my shaft disappearing into him, the way he moaned when I hit deep. I gripped his hips and started thrusting, losing myself in the rhythm, while his hand reached for my balls.
"Harder," Jackson demanded, and I gave it to him, slamming into his ass until we were both slick with sweat and the bed beneath us was soaked.
"Gonna come," I warned.
"On my back," he gasped. "Mark me up."
I pulled out just in time, stroking myself as Jackson presented his broad back to me. My orgasm hit like lightning, painting his skin with thick ropes of cum. He turned his head to watch, eyes heavy with satisfaction.
"Fuck yeah," he murmured. "That's what I'm talking about."
I collapsed beside him, both of us breathing hard. The room smelled like sex and sweat and satisfaction.
"When can we do this again?" I asked, already wanting more.
Jackson's laugh was rich and promising. "How about next weekend?"
----
I'd been running my mouth about my latest hookups when Jackson leaned back in his chair, beer bottle dangling from thick fingers. The conversation had gotten explicit fast: Jimmy on the baseball field, the couple from the club who'd invited me home. Everyone at the table was sharing war stories.
"Not bad," Jackson said, that half-smile playing at his mouth. "They sure sound like fun."
Jackson was nice but quieter than our mutual friends, but he had this presence — broad shoulders, forearms covered in intricate tattoos, the kind of guy who looked like he could pin you down without breaking a sweat.
Three days later, my phone buzzed while I was eating cereal.
*Been thinking about that conversation. You seem like you know how to have a good time. Want to grab beers at mine tonight? Fair warning — I like it rough.*
I stared at the text for a full minute. Jackson was trans, I knew that much from our friends. But the way he'd been looking at me during that conversation, like he was sizing me up...
*Never been with a trans guy before,* I typed back.
*Cool. We can talk it over. Maybe wrestle a little if you're up for it.*
My dick twitched at that. *Yeah. I'm up for it.*
His apartment smelled like cedar and coffee. Jackson handed me a cold bottle, our fingers brushing. He was wearing jeans, a hoodie and his hat.
"So," he said, settling onto the couch beside me. "What's got you uncertain?"
I took a long pull of beer, buying time. "I don't want to fuck up. Don't want to say the wrong thing or... I don't know, treat you like some experiment."
"Appreciate that." Jackson's knee knocked against mine. "But I wouldn't have asked you over if I thought you were an asshole. And honestly? The fact that you're nervous is kind of hot."
The beer was working its way through my system, loosening the knot in my chest. "You mentioned wrestling.", I said trying to sound a little more sure of myself.
Jackson's grin was pure predator. "Yeah. You game?"
We pushed the coffee table aside, cleared space on the living room rug and he took off the hoody. I'd expected maybe some playful grappling, but Jackson moved like he knew exactly what he was doing. Within seconds, he had me on my back, his weight pinning me down.
"Jesus," I breathed. His thighs bracketed my hips, hands locked around my wrists. The heat of his body pressed against mine, and I could feel every inch of muscle definition through his shirt.
"You like that?" His voice had dropped lower, rougher. When I nodded, he shifted his grip, one hand sliding down to rest against my chest. I could feel my heartbeat hammering under his palm.
That's when I felt it — the soft hair of his treasure trail brushing my stomach as he leaned closer. My cock was already half-hard, but feeling that intimate touch, knowing how strong he was, how easily he controlled my movement, made blood rush south fast.
Jackson noticed immediately. His eyes flicked down to where my sweatpants were tenting, and his smile turned wicked. "Well, look at that." He was able to carry me to the bedroom.
Before I could respond, he'd hooked his thumbs in my waistband and pulled my sweats down. My cock sprang free, and Jackson made a sound of appreciation low in his throat.
"Nice," he murmured, then wrapped his mouth around me without warning. He worked me with his tongue, taking me deep, his hands gripping my thighs to keep me still. When I tried to thrust up, he pressed down harder, reminding me who was in control.
"Fuck, Jackson—" I gasped, tangling my fingers in his hair.
He pulled off with a wet sound, looking up at me with dark eyes. "Your turn."
I fumbled with his boxers, hands shaking slightly from arousal and anticipation. When I got them down, I palmed his ass, squeezing the firm muscle. Jackson groaned and pressed closer, his bare chest against mine now. His skin was hot and solid, dusted with coarse hair that tickled my nipples.
"Touch me," he said, guiding my hand between his legs.
My fingers found wetness, heat, the soft folds of his pussy. Jackson was already soaked, and when I stroked tentatively, he rocked against my hand.
"More," he commanded, and I obeyed, working my fingers deeper. He was tight and slick, clenching around me as I explored. The sounds he made were pure sex — low growls and breathy moans that made my cock throb.
"Need to be inside you," I managed.
Jackson reached down, positioning my cock at his entrance. The first touch of my head against his wet heat nearly undid me. He lowered himself just enough to take my tip, and the sensation was incredible — soft and hot and gripping.
"Please," I begged, not caring how desperate I sounded.
He sank down slowly, taking me inch by inch until I was buried completely. Jackson's internal muscles clenched around me as he began to move, riding me with increasing urgency.
"Your ass," I gasped when he paused, both of us breathing hard. "Want to fuck your ass."
Jackson's eyes lit up. He pulled off me, turning around and presenting himself on hands and knees. When I pressed against his tight entrance, he pushed back, taking me deep in one smooth motion.
The sensation was overwhelming — the grip of his ass around my cock, the sight of my shaft disappearing into him, the way he moaned when I hit deep. I gripped his hips and started thrusting, losing myself in the rhythm, while his hand reached for my balls.
"Harder," Jackson demanded, and I gave it to him, slamming into his ass until we were both slick with sweat and the bed beneath us was soaked.
"Gonna come," I warned.
"On my back," he gasped. "Mark me up."
I pulled out just in time, stroking myself as Jackson presented his broad back to me. My orgasm hit like lightning, painting his skin with thick ropes of cum. He turned his head to watch, eyes heavy with satisfaction.
"Fuck yeah," he murmured. "That's what I'm talking about."
I collapsed beside him, both of us breathing hard. The room smelled like sex and sweat and satisfaction.
"When can we do this again?" I asked, already wanting more.
Jackson's laugh was rich and promising. "How about next weekend?"
