The College Jock - Chapter 4 (Patreon)

Author’s note: All characters are consenting adults (18+). All sexual acts depicted are consensual between the characters.

Chapter 4

The week after our first fuck felt longer than the entire semester.

Jackson texted every day. Sometimes three times. Sometimes more. The messages started careful and then got filthier the closer we got to the weekend.

Monday morning, while I was still in bed.

Jackson:you sore from the other night?

Finn:a little. throat still feels it

Jackson:goodi keep thinking about how deep you took itnever had anyone do that beforemy dick gets hard every time i remember the sounds you made

I didn’t answer right away. I was already hard just reading it.

Later that afternoon he sent another:

Jackson:been watching that video i sent you againlooking at my own cock and imagining it in your mouthyou really took the whole thingstill can’t believe it

Tuesday he got more direct.

Jackson:i want more than your mouth next timeyou know that right?

Finn:i figured

Jackson:you ever taken a dick up the ass before?

Finn:twice. both times were smaller. and they didn’t last long

Jackson:mine’s not smallerand i don’t finish fast when it feels goodyou still in, bro?

I stared at the screen for a full minute before typing.

Finn:yeahi’m in

That night I went online and ordered from Amazon a set of silicone plugs and a realistic dildo that was still smaller than Jackson’s dick. They arrived Wednesday afternoon. I locked my bedroom door, lay on my back, and started slow. The smallest plug went in with effort. The middle one made me grit my teeth. By Thursday night I was working the largest plug in and out of myself while replaying Jackson’s video on mute, watching that thick cock flex in his fist and trying to convince my body it could take something even bigger.

Every time I got the plug all the way in I texted him.

Finn:practicing

Jackson:send a pic

I hesitated, then took a photo from behind, shorts pulled down, the base of the black plug visible between my cheeks. I sent it before I could overthink it.

Jackson:fuckkeep that in for an houri want you open for me

I kept it in. My cock stayed hard the entire time. When I finally took it out I was shaking.

Friday the messages got worse.

Jackson:i jerked off yesterday thinking about fucking youevery time i close my eyes i see you on your hands and knees taking ityou’re gonna look so good with my cock stretching that hole

Finn:you’re not helping my nerves

Jackson:goodi want you nervousnervous means you’ll feel every inchi’m not gonna go easy just because it’s your first time with something this sizeyou understand that right?

Finn:i understand, I want to help you Jackson 

Jackson:

you’re a nice dudetomorrow nightsame placeninethis time you’re staying longeri’m not done with you after one round

I didn’t sleep properly Friday night. I kept waking up hard, reaching for the plug again, trying to force my body to accept the idea of something thicker. By Saturday afternoon my hole felt sensitive and slightly swollen from the constant training. I cleaned myself thoroughly, more thoroughly than I ever had, and sat on the edge of the bed staring at the clock.

At 8:40 I left the house.

Jackson opened the door barefoot, wearing only a pair of old boxers. No shirt. His chest looked broader under the living-room light. The second he saw me he smiled, small and crooked, and locked the door behind me.

“You actually came, again.”

“I said I would.”

“Yeah, but people say a lot of shit.” He looked me over. “You nervous?”

“Yeah.”

“Good.” He stepped closer. “Show me.”

I knew what he meant. I turned around, pushed my jeans and underwear down to mid-thigh, and bent forward slightly. Jackson’s hand settled on my lower back. Two thick fingers pressed between my cheeks and rubbed over my hole. I was still slightly slick from the lube I’d used at home.

“You’ve been working on it,” he muttered. “I can tell.”

“Tried to.”

“It’s still gonna be difficult.” He said it simply, like he was talking about the weather. “My cock’s a lot thicker than whatever you’ve been using. You ready for that?”

I swallowed. “I want to try.”

Jackson made a low sound of approval. He steered me toward the bedroom this time. The sheets were already pulled back. He pushed me onto the mattress on my hands and knees, then moved behind me. I heard the sound of his boxers hitting the floor. The mattress dipped as he climbed up.

He didn’t rush the preparation. He spat into his palm, rubbed it over my hole, then pushed one finger inside. Then a second. He worked them slowly, twisting, stretching, while I breathed into the pillow. When he added a third I hissed.

“That’s it,” he said. “Let me open you up. You’re gonna need it.”

He spent a long time on my hole, more patient than I expected, until I was pushing back onto his fingers. Only then did he pull them out. I felt the thick, blunt head of his cock press against me. Even after all the plugs and the dildo, the size difference was immediate and terrifying.

“Breathe,” Jackson said. “I’m going in slow, but I’m not stopping once I start.”

He pushed.

The head stretched me wider than anything I’d taken. The burn was sharp and deep. I clenched the sheets and forced myself to stay still. Jackson kept steady pressure until the head finally popped inside. I made a broken sound into the pillow. He stopped there, one hand on my hip, letting me feel the stretch.

“Fuck,” he muttered. “You’re tight as hell. Even after all that practice.”

He gave me maybe ten seconds. Then he started sinking deeper.

Inch by thick inch. The burn turned into a full, overwhelming pressure that made my eyes water. I could feel every vein, every ridge. My hole felt like it was being forced permanently open around him. When he finally bottomed out I was shaking, breathing in short, panicked gasps. But the feeling was so good, I felt so full and complete.

“That’s all of it,” Jackson said, voice strained. “You took the whole thing. I can’t believe, bro. You’re a champ. Tell me you like my big cock.”

“I love your monster cock, Jackson.”

“Fuck yeah, dude, as you should.”

He stayed still for a moment, fully buried, both hands gripping my hips. I could feel his cock throbbing inside me, thick and relentless. My own cock was hard and leaking onto the sheets.

Then he started moving.

Short, careful strokes at first. Each one dragged the thick shaft against my prostate and sent conflicting sparks of pain and pleasure up my spine. I bit the pillow to stay quiet. Jackson’s breathing grew heavier behind me.

“You feel unreal,” he said. “I’ve never been inside anything this tight. It’s like your hole doesn’t want to let me go.”

He gradually fucked me deeper and harder. The wet sound of it filled the room. Every thrust forced another high pitch noise out of me. The stretch never fully stopped burning, but underneath it something else started building — a deep, helpless pleasure that made my thighs shake.

“You okay?” he asked once, still thrusting.

I nodded against the pillow. Talking felt impossible.

“Use your words.”

“I’m okay,” I managed. “Don’t stop. I never felt a cock so big inside me, this is actually amazing.”

That was all he needed.

Jackson’s control started slipping the same way it had with my mouth. His thrusts got longer, harder, deeper. The thick head of his cock punched against my prostate on every stroke until I was moaning openly into the sheets. Sweat dripped from his chest onto my back. His hands tightened on my hips hard enough to leave marks.

“This is what I’ve been thinking about for ages,” he growled. “A little hole stretched around my cock. Taking every fucking inch. You’re not quitting on me, are you?”

“No,” I gasped. “I’m not.”

“Fuck, dude. I’m not pulling out until I fill you up.”

He fucked me harder after that. The bed creaked under the force of it. I could feel how close he was getting in the way his cock swelled even thicker inside me. My own orgasm was building whether I wanted it or not, driven by the constant pressure against my prostate and the sheer intensity of being opened so completely.

“I’m gonna cum, Jackson. Give it to me, Jackson. Faster.” I choked out.

“Do it. Cum on my cock. I want to feel it.”

A few more deep thrusts and I came hard, spilling onto his sheets without anyone touching me. My hole clenched around him in tight waves. Jackson cursed loudly and drove in to the hilt, burying himself as deep as he could go.

“Take it— take every drop—”

He came with a deep, animal grunt, flooding me with his load. I felt every spurt. He kept grinding through it, pushing his cum deeper, until the last tremor left his body.

For a long minute afterward he stayed on top of me, chest heaving against my back, cock still twitching inside my ruined hole. When he finally pulled out I felt empty and stretched and full at the same time. His load should be so into me that I actually thought it would be possible for me to become pregnant.

Jackson rolled onto his side and pulled me with him so my back was against his chest. His arm locked around my waist. I could feel his heart still pounding.

“You didn’t stop,” he said quietly against the back of my neck. “Even when it hurt.”

“I wanted to do it.”

He was silent for a moment. Then he gave me a friendly punch on my arm.

“We’re doing this again,” he said. “Soon. Fuck. I never had anyone who loves my cock.”

I should have been scared by that.

Instead I just nodded, still shaking, his cum still deep inside me, and already knowing I would say yes again the second he asked.