Scott and Connor Ch. 01

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Freshman begins sexual journey with a senior frat brother.
6k words
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Part 1 of the 8 part series

Updated 06/09/2023
Created 06/09/2018
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When you are a farm boy from a small town in a rural area, you don't talk about feeling different from the other kids. I had learned to talk about girls like I meant it; I didn't.

I chose a college in a good-sized college town, far from the farm. I was hoping to see a different side of life. And I did. There was an active LGBT group and occasionally I saw a same-sex couple or two walking across campus. Still, it wasn't exactly San Francisco.

I'd gone to my share of parties, mixers, frat houses, and so on. I didn't hold out a lot of hope or expectations — the hooking up was overwhelmingly hetero, of course, and that obviously was not my scene. But or lack of anything better to do, here I was...another night at another frat.

That's when I saw one of the seniors I'd spotted around campus.

He was loud, always talking big, and had a braying laugh that fit his wide, toothy smile. He was on one of the school sports teams, amazingly hot, and probably significantly out of my league.

He looked over at me and smiled. I looked away nervously, and he laughed and walked over. Damn.

"Welcome. You new?"

"Um, yeah."

"I'm Connor. Got a name?" He stuck out his hand.

I shook it and said "yeah, of course. I'm Scott."

"Well, welcome to Alpha Epsilon, Scott."

We talked for a few moments about the frat, the kind of people that joined, and the service projects they liked to work on.

"I'll tell you the best thing about us, Scott. Play your cards right, and one of three things can happen."

"What are those three things?" I asked, taking the bait.

"First, we might let you pledge. Second, you might get one of these lovely ladies in bed tonight." He broke off to wave and smile at someone across the room.

After a moment, I said "what's the third thing?"

He lowered his voice and whispered, "depending on what you like, you might get one of these hot guys in bed tonight..."

I dropped my jaw in shock and blushed. Shit. Connor smiled as he saw me react.

"Ahhhh, ok, number three for you, huh? Don't worry, man, we're open minded here. Everyone is welcome."

"No, man, it's not like that, I just... I... Well, I don't really know what I like." Why was I being so open with this guy? I didn't know, but I just felt like it was ok to tell him.

"First timer, huh? That's cool. This is the place to come to fix that!" He draped his arm over my shoulder and guided me toward the kegs. "Need a refill? A little 'liquid courage'?"

"No, I'm good. Still working on this one," I said, lifting my half-filled beer cup.

"Cool." His arm was still on my shoulder. It felt damn good. My cock was stirring.

Connor guided me toward another room, deeper in the house. As he led me through the house, a couple of his buddies looked at him — us — and smiled. One shot him the thumbs up. "Hey, Connor, man, who's your bud?"

"Derek, buddy..." He greeted him with a big "bro hug", slaps on the back and all. "This is Scott. It's his first year. Scott, Derek is one of our frat officers. He's in charge of recruiting new members."

"Aw, c'mon, Connor. You do just fine recruiting new guys, too." He winked and they both laughed. I got the sense there was a joke I was missing, but it hadn't quite connected. "Well, nice to meet you, Scott. Hopefully there's some Alpha Epsilon in you." They laughed loudly as Connor led me away.

I didn't hear Derek turn to another brother and say "Connor will make sure of it before the night is over."

I walked deeper into the house with Connor. Toward the back, we found a quiet corner in the library.

"Scott," he half-whispered, scanning the crowd surreptitiously, "I'm glad you're here."

I was startled. "You... you're glad I'm...? Why?"

"I saw you at the fundraiser for the theatre. And I know you've been here once or twice. And I saw you in the library." He smiled. "The biology section."

My jaw slackened. "I can't believe you noticed me," I said, laughing.

Connor looked me straight in the eye. "Yes, I noticed you. More than once. Dude, you're...well, I don't know, but I definitely noticed you."

He was suddenly really really close to me.

"Connor..."

"Shhh," he said, putting his finger over my lips. The touch was electric. His finger held there, then slid gently over my lips, tracing their curves. His hand slid to my cheek. His thumb stroked my lips as he hovered over me, closer.

"Scott, I have to ask you a question."

I gulped nervously. "What question?"

He looked straight into my face and whispered, "are you gay?"

I paused a long time. This could be very very dangerous. Was he baiting or mocking me?

"Y... Yes," I finally said in a hush. "Yes, Connor, I am. Please...don't..."

"Don't what?"

"Don't humiliate me."

His eyes bugged and his jaw dropped. I felt his hand grip my head firmly and turn my face toward his. "Humiliate you?? I would never do that, Scott. Oh my God, is that what you thought?"

I nodded nervously.

"Scott... I'm gay, too," he said. "And you are fucking hot..." He was leaning closer with each word. Our faces were practically touching. "I can't resist a hot blond farm boy..." he murmured.

And then he whispered: "And I have been hoping to meet you for a while." On the last word he closed the last distance between us and pressed his lips to mine.

It was an amazing kiss. I felt his tongue play on my lips and I opened my mouth to him. As he crushed his lips on mine, his tongue shot into my mouth and tangled with mine.

I backed away, shocked. "Connor... I... shit, man, it's..."

He looked wounded. "You're not into it." He sighed, disappointed. "I'm sorry."

"No!" I yelped. "No, that's not it, it's just... dude, we're in the middle of the room."

A huge smile broke out on his face. "You want to take this where we'll be alone?"

I nodded. He grabbed my hand and half-dragged me from the room, headed for the back stairs. Two flights up and we were at his bedroom door. He spun me around, grabbed my head and planted his lips on mine again. Since there was no one around, I wrapped my arms around him and let it go. I kissed him hard, tangling my tongue with his. He shoved on the door and we half walked, half stumbled into his room. He kicked the door closed with his foot.

He fell onto the bed, dragging me with him. We wrapped ourselves around each other, kissing and hugging for a good half hour. At some point he stripped my shirt over my head, then his joined it on the floor. He was muscled without being ridiculous or showy, and damn his body felt good.

At some point he rolled on his back, pulling me on top of him. His hands slid over my ass and pulled me into him.

"Scott, I won't beat around the bush. I want to fuck. I want us to go all the way, but..."

I was stunned into silence. He waited.

"Scott, are you a virgin?" he finally asked.

I nodded.

"I thought so. I really want to with you, but this has to be how you want your first time."

I thought for a long moment.

"Are you really good in bed?" I asked.

He laughed uproariously. "I think I can say yes to that."

I leaned down and kissed him. "Then I'm ready."

I melted into his arms as he hugged me and kissed me, and I kissed him in return. At one point I started laughing. "What's so funny," he asked.

"This is a huge cliche," I replied. He looked confused. "Senior frat bro beds the freshman and busts his cherry at a frat party?"

He smiled again. "You ready?" he asked. He lowered his eyes and gave me a sultry, almost malicious smirk. "Ready for sex, little virgin?" he whispered.

I inhaled nervously and nodded.

He got off the bed and started to strip his clothing. He shucked his shirt easily, as did I.

Then he dropped his pants.

I stared at his crotch and my jaw dropped. His penis, half hard, stood out from his groin at a low angle.

It was long. Really long.

"Whoa." I whispered.

"What?" he asked, smiling.

"Um..." I stammered, just kinda staring at it.

"I know," he said with a huge shit-eating grin.

"That's huge," I said. "I don't know if it will fit."

"Nah, it will," he said, stepping out of his pants crumpled on the floor and walking closer.

He reached the bed and put his hand on my chest. "Let's try." He gently pushed, and I toppled backwards onto the bed. He grabbed my belt, opened it, and pulled down my zipper. Grabbing my pants by the cuffs, he tugged them off. I scootched upward until my head was on a pillow. He climbed into the bed on his knees. His long cock swung between his legs.

Connor flopped down beside me, bare-assed naked, as was I. He threw the covers over us and burrowed under them. I felt his arms reach around me and pull me close. He kissed me hard, snaking his tongue into my mouth. I met him equally passionately. Our legs started to wrap around each other. He slid a hand around my back as I slid one around his head. Slowly, his hands found their way to my ass.

"Top or bottom?" he asked.

"Uhhh, I don't really know. Maybe both?" I replied.

"I like both, too. But I think I'll top you first..."

He sat up and rolled over toward the nightstand, digging in the drawer for a bottle of sex lube. Then he turned and knelt between my legs.

"I know you're clean," he said. "I am, too. Tested, totally clean." He must have read the confusion on my face. "I want to do this bare," he explained, with a smirk and a wink. "No condom, just my bare dick in your ass. As long as you're ok with it."

I thought about it for a moment. All of those years of safe sex lectures were clanging in my head, but this was my first time...

"Connor, do you swear you're clean? No diseases, no chance of catching something?"

"I swear. 100 percent."

"ok," I said.

He opened the lube and ran a ribbon along the shaft of his cock, and then squirted some on my hole. With his left hand, he started spreading the lube on his cock. I felt the fingers of his left hand teasing my anus and groaned. One slipped inside me, and I closed my eyes as the pleasure radiated up.

"How big is it when you're, y'know...?" I asked.

"Hard?" he asked, fingering my tight bud. I felt a second finger slide inside.

"Yeah," I said.

"Big," he laughed.

"How big? Like, um, six inches? Seven?" I pressed.

"Eight and a half," he said proudly, while his fingers danced in my hole. My eyes widened. A third finger joined the other two, opening me up. "Sometimes nine, if I'm really horny."

His left hand was masturbating his cock and I watched as it got longer and harder. When he took his hand off it, it slapped up against his stomach. What had been a half hard-on was now a rock hard cock, ready to fuck.

He lifted my right leg, moved closer. I raised my left leg and balanced it on his shoulder. He squirted more lube on my hole. He thumbed my rosebud, testing it.

"You're ready," he said. And then he grabbed his cock and angled it toward my tiny rosebud.

"I really... I don't know if..." I stammered.

"Only one way to find out..." he said, moving into position. He placed the head of his cock at my hole, shifted his knees, and aimed. "Ready to try?" he asked.

I was nervous. I could feel the heat and hardness of his cock pressing in. "Can I try?" he asked again.

I nodded. "Um, yeah, ok. Go slow, ok?"

He smiled toothily, almost wickedly, and hissed "yeah!" I felt him start to lean in.

Connor had done a good job opening me with his fingers; the knob of his shaft spread my bud and pushed inside. He sighed and groaned, closing his eyes and smiling as his spear penetrated. I had only a moment to think about that when I felt a spasm of pain in my asshole. "Unnnggggh" I moaned. Connor stopped his advance. "OK," he said, "easy... Take a moment to get used to it." I was panting and grunting at the invasion by his shaft.

He kissed me again and then sat up. "I'm going to move again, Scott. Get ready." He pressed forward gently and I felt his cock slide a little deeper. It was stretching me, but not painfully. "You ok?"

"Yeah, yeah, I think so. It's...weird. But good. Fuck, you're big."

It took a few more minutes of gentle sliding back and forth, but I felt my hole relaxing around him. He felt it, too.

The thought crossed my mind that with Connor's cock in my ass, I was no longer a virgin...

"Connor..."

"Yeah, Scott?"

"You're..."

"Really big?" he laughed.

"No... Well, yes, you are. But... you're also... um... in me..." I finally mumbled out.

Connor leaned down and touched my cheek, smiling. "Yeah, I guess I am." He leaned down and kissed me. It was firm but a little more playful. He did it again. "How does it feel not being a virgin anymore?" There was a strange softness in his voice.

"Ok, I think."

"I'm gonna go deeper," he murmured. He braced his hands on both sides of me and pushed his hips forward. Several inches of his cock slid inside and I could feel the head of his cock rearranging my guts. I grunted. "You ok?" he said.

"Yeah," I moaned. "I'm ok. I think."

He started to withdraw, just an inch or two, and then slowly pushed in. I moaned. He pulled back a couple of inches and slid back in. I saw his eyes close as he began to rhythmically pump his hips back and forth. "Ohhhh, yeah..." he moaned as he started to move in and out of me. I was grunting and breathing pretty hard as he slid back and forth.

"Are you ok?" he asked again. "This feels fucking amazing..."

"Yeah," I said. "Yeah, I'm ok. It's...fuck, it's really big."

He kept slowly moving in and out, and I could feel my hole loosening around him.

"Are you all the way in?" I asked

He laughed. "No. Well, at least not yet." There was that evil smirk again. He looked down at his cock. "'A little more than halfway, though. Maybe three or four more inches to go."

He leaned down closer, and spoke quietly. "You want it?"

I swallowed hard. "Yeah, I think so. Easy though."

He gripped my ankles hard and spread my legs. He licked his lips. He gave a little grunt as he squeezed his ass muscles. I felt incredible pressure at my asshole as his shaft slowly ground forward. Inch by inch, the twenty-one year old senior drilled his incredibly long cock into me and slowly slid all the way up inside me. I felt his crotch pressing against my ass as he sheathed over eight inches of cock in my tight virgin ass.

"Yeahhhhh," he moaned, pressing hard against me. "Ohhhh, fuck, that's so good."

He started a gentle pump-and-thrust pattern. He'd pull back, pump a few short strokes halfway in, and then slide into me, all the way, and press against me hard as his cock penetrated deep inside me.

"How hard can you take it?" he asked, pumping slowly.

"I don't know," I said.

"Let's find out," he said. He slowly pulled back, until half his cock was out of me. He gave me three or four firm short pumps and then pushed forward firmly, burying the whole shaft in me in one long, slow thrust. I groaned, but took it.

"How was that?" he asked.

"Ok. I think."

"Try again?"

"Yeah, easy though."

He pulled back, further this time, gave me a pair of short stabs, and then pushed in again, a little faster and harder. He waited a moment, then pulled out more than half way, and then shoved forward faster again. On the third stroke, he pulled back pretty far and this time shoved forward really hard, going all the way into me in one quick stroke. He pressed down hard, making sure his cock was all the way in. He went really deep and I could feel the hardness of his shaft way up in my guts.

Then he smiled. "I think you're ready."

I wasn't sure what he meant and he gave me no time to ask. He grabbed my ankles, spread my legs wider, and shifted his knees. My legs were higher and his hips were more on top of me than before. It took me a moment to realize he was trying to make it easier for him to plunge into me. Instead of having to use his hip muscles to thrust forward, he would be able to use his weight and gravity to drive his cock down into me.

He pulled all the way back. I could feel an emptiness left behind as he pulled his cock almost all the way out. Reversing, he pushed down slowly but firmly, sliding his cockshaft all the way into me. He pressed his groin against my butt for a moment, then pulled back again and pushed down again. He did it again, then started to move in and out without pausing.

"Oh yeah," he moaned. "This is fucking awesome... I knew you could take it."

Then it hit me what he was working up to and what he might do.

"Um, are you...?" I asked.

"Am I what," he whispered, continuing to stroke.

"Are you...y'know...close?"

"No, " he grunted, plunging deep into my guts. He cracked a very nasty smile. "Well, not yet."

"Are you gonna..."

He laughed. "Am I gonna what?"

"You know," I said, sheepishly.

"Am I gonna cum?" he said.

"Yeah."

"Well, yeah, eventually," he laughed. He gave me a few more strokes and then pushed in really deep and held it there. "Want me to cum in you?" he asked.

"Um, well, I... I mean..."

"I can if you want," he breathed, resuming his stroking. "Taking a big load your first time...it's pretty hot." Connor was once again moving his cock rhythmically in and out of me. "Yeah, man, I should definitely cum in you..."

"Did you say a big load?" I asked.

He smiled, still thrusting. "I did. I cum a LOT, man. Really big loads..."

"Connor," I whispered, "um, no one's ever cum in me before."

"I kinda figured," he said, smiling hugely. "May I be the first?"

I nodded silently. He pumped harder, now determined to trigger an orgasm.

"Oh, yeah, gettin' closer..." he moaned, after less than a minute.

"Oh God, you're so deep..." I moaned.

"Yeah, man, super horny now," he said between thrusts. He smiled again. "Definitely feels like you got me to nine inches, unnnhhh..."

Connor's breathing got ragged as he kept stroking in and out. His eyes closed and his mouth hung open as the waves of pleasure radiating up his hard, thrusting cock soaked his brain in sex hormones and endorphins. His brain and body were completely consumed with the urge to complete the sex act and ejaculate. My own head was swimming as I realized what was about to happen. That massive sex organ between his legs had one single purpose: to breed. Any moment now, it would fulfill its purpose and start shooting his DNA into me.

Connor was going to cum in me. I couldn't stop him now if I tried.

"Ohhhhh, fuck... I'm really close..." he moaned.

Stroke..."Fuck, Scott, my dick's gonna shoot..." His grip on my ankles tightened.

Stroke..."Fuck..."

Stroke... "Oh, FUCK...!" He stretched my legs way up, opening me completely.

He plunged down hard. Every inch of his shaft plowed deep inside me. I felt the huge column of flesh start to throb, and then he groaned loudly as he released. I could actually feel the seed tube on the underside pulsing hard against my anus and realized it was happening. He was shooting his load and filling my guts with his sperm. The warmth spreading up inside me...was him.

His body was coiled tightly for several seconds — ten or fifteen — then suddenly relaxed and collapsed forward onto me. He started panting for breath, and I could still feel his cock throbbing and pulsating inside me. I think it took a while to drain his full load into me. After a minute, though, he seemed to return to Earth, smiling hugely.

"Shit..." he said. He leaned back and started to stand up. His cock pulled out of me as he got on his feet. It looked angry and bloated, and it was still hard and twitching. A long string of semen dripped from the tip and fell on the bed. He grabbed a towel and wiped his organ clean.

"Fuck..." he whispered, cleaning the shaft. "That was awesome."

He raised my legs and shoved the towel under my ass.

"What?" I said.

"Uhh, I just shot in you, man. It's gonna leak out all over the bed."

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