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A Favor for the Freshman Ch. 01

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Roommate needs help to get off. What will I do?
2.3k words
4.6
13.6k
36

Part 1 of the 2 part series

Updated 06/23/2024
Created 06/11/2024
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Some time ago, I wrote a fan sequel to 'The Freshman Favor Ch. 01' by Fit_for_a_Fuck. It's a really great story but unfortunately ended before I felt the story ended, so I continued it. However, because I can't get permission from the original author (they haven't replied to my messages), my AU fan fic sequel isn't allowed under Literotica rules.

So, my only option, if I want to publish my second chapter, is to write my own version of the first chapter. The upside to this is that I can change things however I like. Not that I want to change much, as it's a fantastic story, but anyway here's my take on it.

I would still recommend you read the original too, as it's a really good story.

***

My name's Ash. I'm your typical nerd. I'm short for a guy, pretty scrawny, though with a bit of a bubble butt and thick hips and thighs, and into nerdy things like sci-fi and tech.

My best friend since we were kids is Jeremy. He's totally different from me. He's tall, muscular, and cool. If it hadn't been for him, I would never have been invited to any parties in high school and probably never would have even kissed a girl.

When we graduated high school, we went to the same college together and even shared a dorm.

We studied different subjects and Jeremy spent a good amount of time training with the football team but we still spent a lot of time together, playing video games and chatting.

One Saturday night, about three months into our first year at college, we went to a party the football team was throwing in a dorm across campus.

I got ready -- t-shirt, jeans, thong, sneakers. Yeh, thong. I got into wearing women's lingerie in high school. I was straight but it excited me to feel like I was barely wearing anything beneath my jeans. Since this revelation, I wore a thong or silky panties under my regular clothes ever since.

When we were both ready, we walked across campus together, Jeremy carrying the heavy case of beer like it was nothing.

When we got to the dorm where the party was happening, it was already in full swing. We heard the hip-hop music played from a block away, there were dozens of people in the hallway, girls grinding themselves against the guys, bras and panties flying, and everyone looked like they had a good buzz going.

As a nerd, I didn't expect to get much action but I managed to get dances with a few girls, just by being at a cool party in the first place. But Jeremy got even less attention than me. He was a jock and well-liked by the rest of the football team, and I thought he was really cool, but he didn't have the 'look' the party girls were looking for. I think the main problem were the deep pockets and scars on his face from some terrible acne he had as a kid. He would approach a girl or two and they would refuse him and I would feel really sorry for him, especially when a girl was grinding against my junk on the dancefloor.

Other jocks managed to fuck two or three girls a night, let alone one, but Jeremy never seemed to get any luck.

Around 2am, we got back to our dorm, totally wasted.

Jeremy went to the bathroom for a piss and I started getting ready for bed. I removed my t-shirt and pulled my jeans down, forgetting the bright red thong I was wearing beneath, just as --

"Ash, what are those?" Jeremy asked, coming out of the bathroom.

I stood up straight and turned around to face him, trying to cover my thong with my hands and the jeans I was holding. I could feel my face going bright red with embarrassment and humiliation.

"Nothing, dude, just my boxers," I tried to style it out.

"No no no, that's a thong, man, a woman's thong."

"Well ... yes, I guess it is," I said, not knowing what else to say. "I'm not gay or anything. I just, it's just, I like the way they feel."

I picked up some gym shorts and slipped them on over the thong.

"Don't worry dude, I'm not judging. It actually looks pretty good on you," said Jeremy, as he went over to his bed and slipped his own jeans down.

"Erm, thanks," I said awkwardly.

We both climbed into our own beds and turned the light off.

I laid there, staring into the dark, for a long time before I finally fell asleep.

"Ash," I heard, waking me up, "you awake?"

"I am now, why?"

"Dude, I'm sorry, I just... I can't get that thong out of my head."

"I thought you said you wouldn't judge?"

"I'm not judging, I'm ... horny."

"You what?"

"Listen, I haven't been laid since we got to college, I'm getting really depressed with all the rejections. When I saw you in that thong, like I said, you looked good!"

"Erm, thanks?" I said, not sure where this was going.

"Listen, I know this sounds crazy, but, we've been friends a long time, and well, could I ask you a favor? Would you ... give me a handjob? Just to get me off, so I can get to sleep."

I was confused. My best friend -- only friend really -- wanted me to wank him off? And he liked the way I looked in women's lingerie. But he was my friend. I guess all it would be would be a mechanical operation -- moving my hand in a way to get a result. That wouldn't make me gay, would it? But then I realized I was hard. Harder than I'd been in a while. Was I getting into this? Was my body telling me to do it?

"I'm sorry," said Jeremy, "it's too much isn't it."

"No," I said as a reflex, without thinking. Then I had to follow it up. "It's just that, it's a bit weird. But we're friends. If you want a favor from me..." I left the rest unsaid. We were probably so wasted neither of us would remember in the morning anyway.

"Seriously?" Jeremy asked, "you'll really do it?"

"Sure," I said, taking the final leap. "Just this once though."

"Yeh, just once, no worries," Jeremy agreed enthusiastically. "You're the best, dude!"

Jeremy got out of bed and sat on his computer chair, turning it to face me. I saw the large bulge in his boxers and gulped.

I walked over to him and started leaning forwards.

"Hang on," said Jeremy, "first, could you take off those gym shorts? That way I can pretend it's a girl giving me the handjob, not a guy."

I just nodded and took off the shorts, revealing myself to someone in my thong for the first time.

"Could you turn around?"

I did what he asked and turned my back to him.

"What about arching your back a bit, bend over a little?"

"What the fuck?" I asked.

"Come on dude, I really need this. You look so good in that thong!"

I again did what he asked, bending forward a little, arching my back, pushing my butt out, my cheeks parting a little.

"Mmmm, that's hot," Jeremy moaned.

"Hearing his response got my motor running a little. It was a good feeling, knowing someone, even a guy, was attracted to my body and was getting off on looking at my ass. Without really giving it any thought, I felt my body start moving, shaking my ass gently from side to side, even twerking a little."

"Mmmm, very nice, how about you back that thing up?" Jeremy asked.

Did he mean he wanted me to put my ass in his lap? I looked back at him, uncertain.

"Come on dude, just a little lap dance? It'll get me going faster."

I figured it would probably get all this over faster so I went back to twerking and started shuffling backwards until I felt his thighs either side of mine and I lowered my booty a little and found his lap, an impossibly hard-feeling sausage laying there.

I put my hands on my knees for support and started grinding my almost bare ass on his hard cock between my cheeks.

"Fuck yeh, that's fantastic, keep going," Jeremy encouraged me.

He grabbed my hips and started guiding my body, directing how he wanted me to grind my booty on his cock.

It felt surreal and the weirdest part of all was that my little cock was as hard as I can remember it ever being, leaking pre-cum into my lacy red thong.

There was something oddly reassuring and safe-feeling about being moved and used by Jeremy's big, strong hands. I hardly needed to do anything. He could lift me like I was nothing and direct my ass to where he wanted.

"So, how about that handjob?" Jeremy asked after a while.

"Sure," I said, without thinking. I'd kind of forgotten that I'd agreed to wank him off as well as let me grind my almost bare ass into his monster cock.

I turned to face him and knelt on my knees between his thighs, without really thinking about the submissive role I'd adopted, and then I found out just how monstrous his cock really was.

I tentatively reached for the waist of Jeremy's boxers. He lifted himself off the chair for a second so I could pull down his underwear for him, and his massive manhood came waving into view.

I looked at it in awe as it stood before me, twitching slightly with his pulse. It must be at least 11 inches long and thicker than any cock I'd seen.

I felt small and emasculated in front of this virile sign of masculinity.

I gulped nervously.

"Okay, go ahead."

I nodded absentmindedly and slowly reached out. My small hand looked like a girl's as I stroked him tentatively.

He moaned as I touched him.

When I reached the base of his cock, I tried to grasp it, though my fingers didn't touch my thumb, and started a jacking off motion, stroking up and down the incredible member.

This was such a strange situation, I couldn't really remember how I had got myself into it. I felt almost like I was floating, watching the situation from outside my body, like all this was a dream.

"Oh fuck, yeah, that feels great, baby!"

Did Jeremy just call me baby? Just ignore it and carry on -- it might make it go faster.

"Ash?" Jeremy said a couple of minutes later.

I looked up at him.

"Could you use both hands?"

I just nodded and added my other hand to the task.

"And, erm, use some spit?"

I spat into my hands and rubbed it in to my friend's monster cock as I continued jacking him off with both hands.

"Oh yeh, that's it, that's so fucking hot, baby! Yeh, stroke it, just like that, stroke it baby, yes baby," he carried on encouraging me and calling me baby. I just ignored him and continued my task.

A couple of minutes later, Jeremy stood up in front of me, making me feel even smaller and weaker than ever. Subservient.

"That's it, look up at me as you jack me off, that's it baby."

"Just, warn me before you cum won't you?" I asked.

"Of course, dude! Just, keep going, I'm nearly there. Yeh, that's it baby, so fucking hot, yes," he carried on his encouraging dirty talk, looking directly down into my eyes this time.

This felt so weird but I just couldn't turn my eyes away from him.

I picked up the pace, jacking him as fast as I could, trying to get it over with. He was producing more and more precum, making it easier to glide my small hands over his massive cock.

"That's it, nice and fast," Jeremy moaned. He sounded like he was close.

I kept jacking, waiting for the warning to get out the way.

"Yes, that's it, so close, keep going, so fucking hot, baby, so hot, that's it baby," he groaned.

Then he grabbed my head with one massive hand, then he grabbed both of my hands on his shaft with his other hand, and he kept me pumping, his tip pointed directly at my face. I tried to move away but he was too strong. I couldn't move at all unless he allowed it.

"No, please don't," I whimpered, probably too quietly for him to hear as he roared, "take my cum, you little slut!" and I was struck by a river of hot thick cum, right in my eye, splashing over my face, over my nose, some even getting in my hair. It kept coming, covering me, plastering me in thick white cum.

"Thanks dude, I really needed that," said Jeremy. I was able to open one eye enough to see him walk past me and flop into his bed.

Silently, I got up and went to the bathroom to clean up.

I guess it wasn't all that bad, I reflected. I was doing a favor for a friend and it got a bit messy. Still, it was the last time. I wouldn't do it again, no matter how much he asks.

I pulled my thong down and stepped out of it and started the shower.

I was still as hard as steel.

I got into the shower and started stroking my cock as I felt my friend's cum washing away from my face.

I was hornier than I'd been in my life. The situation was so taboo, my friend and roommate treating me like a slut and cumming all over me after I gave him a lap dance. I wasn't gay but it was seriously hot.

I thought of Jeremy's masterpiece of a cock as I humped my hand until I spurted my pitifully small amount of cum against the shower wall.

When I got back to our room, Jeremy was fast asleep.

I got into my bed and soon fell asleep too, wondering what would happen in the morning.

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4Leather4Leather10 days ago

Love it. Can’t wait for the next chapter. See if this goes anywhere.

AnonymousAnonymous13 days ago

we short sissy guys all have that big jock guy best friends who we want to make us feel like a real girl. cant wait for the next part.

TinaMichele189TinaMichele18914 days ago

I love it. I had a roommate he showed me his cock one night when he was drunk...it was a huge nice big and thick cock...many times I fantasized about that nice cock busting my ass or spray cum on my face. Maybe one day!

GracefulFeminizationGracefulFeminization14 days ago

Lovely!

I also loved the original story and always hoped to see more of it!

ShortyMacShortyMac14 days ago

I can relate to how Ash is feeling. Being 5’4” 100 pounds when I was in high school. At that time only sexual thing I had done was my best friend Robert and I use to jerk off next to each other. We never touched or anything. Then when I turned 17 my Father signed the paperwork to join the Navy. After boot camp I was assigned to be base personal at NAS Miramar. At that time found out about gloryholes in bookstores. Every weekend was there getting sucked off. 🤤

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