The Freshman Favor Ch. 01

Story Info
College freshman agrees to help out his beefy roommate.
3.6k words
4.44
107.2k
130
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Ash?" I heard my roommate Jeremy call out. "You ready yet? You're taking forever in there."

"Yeah, man," I answered. "Be out in a sec."

I was two months into my freshman year at college. I was on the college swim team. I stood at about 5 feet 8 inches and weighed somewhere around 160. I was pretty slender but had some weight around the mid-section, hips, and thighs. At the time I had bleached blonde hair that I spiked. All in all, if you had to label me I was pretty much your typical preppy guy. My roommate Jeremy, on the other hand, was on the football team and played linebacker. He was massive! He was probably 6 foot 2 and weighted at least 250 pounds, had short hair and a ton of muscles.

It was Saturday night and we were getting ready to head out to a party that the football team was throwing in one of their dorms. Even though I wasn't on the team I knew most of the guys through Jeremy so I usually went to their parties. They were always pretty crazy. Naked chicks. Binge drinking. Loud music. The works, you know?

I got done taking a piss and pulled up my thong. Yes, that's right, you heard me, a thong! I wasn't gay or anything. I just liked the feeling. During high school I developed a bit of a lingerie fetish. Not on girls, but on me! I just loved the feeling of wearing next to nothing under my jeans. It just always felt so liberating. So, I wore either silky panties or skimpy thongs most of the time under my regular clothes.

I washed my hands, slapped some gel in my hair, and came out of the bathroom. Jeremy was standing in the room with his arms crossed.

"Come on, man," he said. "We're gonna be late."

"Okay, okay, I'm coming, dude," I said.

We left our dorm and headed across campus, a case of beer in tow, to the dorm where most of the football players lived. When we got there the party had already started. There were dozens of people in the hallway, walking from one room to the next. Hip-hop dance music was blaring and the girls were grinding up against each other. Bras and panties were being thrown carelessly around and the guys were yelling and urging the girls to makeout with each other.

The party girls never really went for Jeremy, not the way they did with the other jocks. Most of the football players could fuck several girls a night, let alone one. It wasn't that he was ugly or anything, it's just that he didn't have that "look" that they were after. For one, he was really big! And his face had deep pockets and some scars on it from the terrible acne he had when he was a kid. Every time I saw a chick turn him down, I have to admit, I felt a little sorry for him, especially when there was a girl grinding up against my junk!

It was around 2 in the morning when we got back to our dorm. By that point we were both pretty wasted. Jeremy headed straight for the bathroom to take a piss and I started to get ready for bed. I unbuttoned my shirt and threw it on the floor. I grabbed a white tank top and tossed it over my head. I unzipped my jeans and slid them down my legs, forgetting that I had a skimpy flesh-colored thong hidden underneath. And then...

"Ash, what are you wearing?" I heard Jeremy's voice ask from behind me.

I stood up straight and felt my face grow red.

"Ummm...nothing, man...just my underwear," I said, trying to brush it off.

"Dude, those are chick's underwear. That's a thong, man."

"Uhh...yeah....yeah, it is. I mean...I'm not gay or anything, dude...I just like how it feels."

Not knowing what else to do, I quickly grabbed a pair of gym shorts that were lying on my bed and slipped them up my legs, covering the thong.

"They don't look that bad on you," Jeremy said walking over to his side of the room and slipping his jeans down. "Don't feel bad, dude. I won't judge you for it."

"Uh, thanks, man," I said, not knowing what the hell else to say!

We both climbed into our respective beds and shut our lights off. I laid there for a few minutes and then rolled over onto my stomach and dozed off.

I was awakened by the feeling on something hot pulsating against my backside. I felt hot breath against the back of my neck that sent shivers down my spine. Something long and hard was moving back and forth between my asscheeks. And, to my surprise, my cock was as stiff as ever!

"Wh...what...is...going on?" I mumbled in my drunken daze.

"Shhhhh...just go back to sleep," I heard a low voice answer.

I dozed off for just a few seconds. I woke up again when I felt my shorts sliding down below my buttcheeks.

"What the fuck!?" I yelled sitting up.

I curled up at the top of my bed and flicked on the lights. I saw Jeremy sitting at the bottom of the bed in only his boxers with his head in his hands.

"J...J...Jeremy," I muttered. "What the hell are you doing, man?"

"I...I'm sorry Ash...I really am," he said, sadly. "It's just that...I haven't been laid since high school. None of the girls here will even look at me. I'm desperate. Then...when I saw you in that thong...I got...really turned on and thought...maybe I could just dry hump you while you were sleeping."

I just stared at him, not knowing what to say. I did feel bad for him, but this was taking it a little too far.

"I'm really sorry Ash," he apologized. "I'm just desperate."

I still didn't know what to say to him. Did I feel bad enough to give him some kind of relief? Would that make me gay? I had never really been attracted to men before, but my cock was stiff from Jeremy's desperate attempts to dry hump me. Was my body telling me to go through with this? I wasn't sure. Then, before I could say anything, Jeremy dropped a bomb.

"I know this is crazy, but...could you at least give me a handjob? Just to get me off. Then, I'll leave you alone."

What!? How did this happen? When did my own roommate think he could talk to me like some trashy party slut? I just stared blankly at him.

"I need this Ash," Jeremy begged. "I'll give you anything you want. Money? I just really fucking need this."

I really felt bad for the guy. Scenarios starting playing in my mind. Would a handjob really be all that bad? It wouldn't get awkward between us, would it? And besides, we were both so wasted that we'd probably forget all about it in the morning, right?

"Come on, Ash," he continued to beg. "Just real quick. It won't take long. I promise."

"Okay, Jeremy," I said, after a long pause. "I'll do it."

"You will?" he asked, almost surprised that I agreed to do it.

"If you really need it that bad, then, yes, I guess I can give you a handjob."

"Aw, man. You're the best, dude."

"Alright," I said hopping off the bed. "Go sit over there at your computer."

Jeremy gleefully jumped off the bed and sat in his computer chair and turned to face me. I noticed that his hand was already stroking the incredibly large bulge in his boxers. I walked over to him and reached down toward his crotch.

"Wait," he said, grabbing my wrist. "Could you...um...take your shirt and shorts off."

"Why?" I asked, laughing a little.

"I just...uh...want to see you in that thong again. That way I can pretend that you're a chick giving me a handjob...and not a guy."

"Wow, thanks, man," I said sarcastically. "That makes me feel so much better about this."

"I'm sorry, man," he apologized. "But you look really fucking hot in that thong. Seriously, dude, you got a great body."

"A great feminine body, though, right?"

"Well...yeah...take it for what it is, man."

"Alright then," I said, slipping out of my tank top and gym shorts and kicking them to the side. I now stood before my roommate in nothing but a flesh-colored thong.

"Turn around," he ordered.

I did as he told me. I figured I might as well do what he says and get this over with as quickly as possible.

"Could you bend over a little...and arch your back?"

"What is this, a strip club?"

"Please, Ash. I really, really need this."

I placed my hands on my smoothly-shaven thighs and bent over slightly. I felt my asscheeks spread open a little as I arched my back as much as I could.

"Awwwwww...yeah," I heard Jeremy moan from behind me. "That's so fucking hot."

I have to admit I was getting a little turned on knowing that a guy was really attracted to me and was getting off just by staring at my ass. So, I started to improvise a little. I shook my ass from side and side and up and down, popping my booty for my roommate's pleasure. I continued to hear him moaning and urging me on as I did my little dance for him.

"Ash?" Jeremy asked. "Could you give me a little lap dance, just to get me going?"

"I think you're already more than ready to go, dude," I responded, looking back at him and eyeing the gigantic bulge in his boxers.

"Just a little one? I just love watching your ass in that thong."

"Okay, man," I said with a smile. "Just a little one and then we're getting this thing over with, okay? This is getting weird."

"Deal."

I walked over to him and turned around so that my thong-covered ass was just inches from my roommate's face.

"I'm not really sure how to do this," I admitted.

"It's cool, just sit on my lap and rub your ass back and forth on my cock," Jeremy suggested. "Nothing fancy. I just need to feel your bare ass against my cock."

I blushed a little when he said this and got ready to try to give him a lap dance. I held onto my knees and squatted down until I felt my asscheeks graze the fabric of his boxers. I felt his hands grab my love handles as he guided my ass to his cock. He pulled a little on me and I sat down, immediately feeling his long hard cock fill the crevasse between my ass. With my hands still on my knees for support, I began rocking my ass back and forth against the bulge in his boxers.

"Awwwwwww....fuck yeah," he moaned. "That feels so fucking good."

I continued massaging my roommate's cock with my bare ass. Up and down, up and down, up and down I moved my booty across his very long cock. The weirdest part of all this was that my own dick began to harden even more. I didn't know what to make of it; I just kept working my ass over on my roommate's giant rod, trying not to think about how wrong it felt. After a while, I started gyrating it side to side in a circular motion, trying my best to imitate what I'd seen strippers do on the internet. The next thing I knew, I felt Jeremy's large manly hands firmly grip my hips. He let out boisterous moans as he pulled my ass deeper into his crotch, grinding monster cock against my butt cleavage. I started to feel a little dirty, like I was being used. It felt wrong.

"So...how about that handjob?" I said flinging his giant hands off of me and quickly standing up. I was trying my best to move things along and get this over with before it got any weirder.

"Yeah...okay...go for it," Jeremy urged.

"How...how do you want me?" I asked nervously.

"On your knees," he said with a devious smile.

I just stared at him with an accusing grin and said, "On my knees? Come on Jeremy, really?"

"It's no big deal," he assured me. "Just get on your knees and stroke my cock until I cum and then we'll be done with this."

"Okay," I said. I placed my hands on Jeremy's massively muscular legs for support and lowered myself to the floor. When I got to the ground on my knees I felt dwarfed, even though he was sitting in a chair, by my roommate's 250 pound frame. And, along with being in a submissive position, I felt a little emasculated by the whole situation. But my dick was still standing at attention and I was a little freaked out by it.

"Here," Jeremy said lifting his butt up off the chair and sliding his boxers down. "Get to it."

My mouth dropped open and my eyes widened. I was staring at a massive cock. It must have been at least 10 or 11 inches long and pretty thick too. How were these party sluts not taking advantage of this monster? Why would any chick turn a guy this well-endowed down? I gulped a little, nervously thinking about what I had promised to do.

"You okay?" he asked me.

"Mmmmhmmmm," I hesitantly responded, gulping a little.

"If you don't want to Ash...," he said, sounding disappointed, "I understa..."

"No, no, no," I said, cutting him off. "It seems like you really need this and I promised, so...here goes nothing."

And with that I reached my dainty little hand out and touched the tip of Jeremy's cock. He shuddered and moaned as soon as he felt my fingers gently brushing along the length of his shaft. After teasing him for a few seconds, I reached the base of his cock and wrapped my small hand around it. Then, I began slowly jacking him off.

"Is this good?" I asked, trying not to make eye contact. I didn't want it to get any more awkward than it already was.

"Oooooooo...yeah," Jeremy moaned. "Holy fuck...that's so fucking hot, baby."

I didn't know what he meant by this. Was it hot just because he was getting off? Was it hot because he was imagining some hot chick doing it? Or was it hot because I was doing it?! And "baby"? Why was he calling me "baby"? These questions reverberated in my brain as I kept stroking my roommate's engorged member.

"Ash?" I heard Jeremy ask.

I looked up at him and met his eyes, not missing a beat with my strokes.

"Could you use both hands...and some spit?" he asked.

I let go of his cock and brought my hand to my mouth. I gathered up as much saliva as I possibly could in my mouth and then spit a big wad into my hand. I brought my other hand up and rubbed the spit in both hands. Then, I reached out with both hands and gripped Jeremy's rod. I rubbed some saliva along his shaft and then, with both hands, started rhythmically stroking his smooth cock.

"Yeah...yeah...oh yeah...that's it...that's it, baby," he moaned loudly. "Just like that. Stroke my cock...stroke my cock, baby."

There was that "baby" word again? And why was he talking so dirty to me? This was getting too weird. I just wanted to make him cum as soon as possible and forget the whole thing ever happened.

I jacked him off for a few minutes, trying my best to get him to cum.

"I don't think I can cum like this," Jeremy said.

I looked up at him suspiciously and said, "What do you mean, like this?" I was a little nervous that he'd try to get me to give him a blowjob or something.

"No, I mean, I don't think I can cum sitting down. Do you think it would be okay if I stood up?"

"Umm...," I hesitated, letting go of his cock.

"Don't worry," he assured me, standing up without my permission. "I won't cum on you. I'll warn you before I do and then you can get out of the way."

"Okay...just hurry it up, already," I said. I was getting impatient with his demands.

"Alright, put your hands back on my cock," he ordered, pointing down to his swollen penis. "A few more strokes should do it."

I obeyed and quickly wrapped my sticky hands around his cock once more. I began jacking him off more rapidly than before. I noticed strands of precum leaking from the tip of his penis. A little bit ran down the shaft and through my fingers, mixing with my saliva to create a really sleek lube. Up and down, up and down. I slid by slick palms up and down my roommate's long shaft.

"Faster...faster...oh yeah," Jeremy moaned.

"Should I move now?" I asked, looking up at him.

"No, no, I'm not quite there yet. Just keep going, but do it with just one hand now."

I took my left hand away and placed it on my naked thigh and continued stroking the entire length of his cock with my right. Was he ever going to cum? God, he was taking forever? I just wanted to get it over with and go to sleep and wake up and forget all this ever happened. Then, all of a sudden, I felt a big meaty hand grab my shoulder.

"Hey, what the hell?" I said.

I let go of his cock and tried to get away, but he was too strong and held me in place on my knees before him, just inches from his swollen cock. He took his free hand and grabbed the base of his cock. He began violently jacking himself off, all the while keeping the head of his cock pointed directly at my face.

"Get ready slut," Jeremy replied, staring down at me with a sadistic look. "My big load is going all over that pretty face of yours."

"No, Jeremy, please don't," I pleaded, but to no avail. I was getting scared; scared that he would hurt me, but also strangely turned on. My cock was still standing at attention inside my thong

"Here it comes bitch," Jeremy said. "Get ready."

Not having any choice, I closed my eyes and prepared myself to get soaked by my roommate's load.

"Aaaaahhhhh...ahhhh...ooooooo fuck...I'm gonna cum you fucking slut!" Jeremy yelled as his cock shot strand after strand of hot cum all over my face. The first couple landed on my nose and slid down my cheeks. The rest hit almost every part of my face. My chin, cheeks, lips, eyelids, and forehead were all covered with hot sticky jizz, a little even got in my hair.

After every drop of cum was out of his cock, Jeremy released his grip on me and I tumbled to the floor like a sack of bricks. Jeremy continued standing over me, panting heavily, as I wiped the cum from my eyelids with my hands. Not knowing what to do, I remained on the floor, ashamed and embarrassed, covered in my roommate's cum in nothing but a skimpy thong. I felt dirty and used, but I was still hard.

After about a minute Jeremy pulled up his boxers and walked past me to the bathroom. I picked myself up off the floor and grabbed a tank top to wipe the cum off of my face as best as I could. Questions were racing in my mind. Why did he use me like that? Would we ever be able to go back to "normal" after this? What was I to say to him when he got back from the bathroom? Finally, the door to the bathroom opened and Jeremy walked out and sat on the edge of his bed.

"Listen, Ash," he said in an apologetic voice. "I'm sorry about all that. I guess I got a little carried away."

I just sat in silence on my bed, staring at the floor.

"It was wrong, man. I shouldn't have done that to you. I mean, you were trying to help me out and I took advantage."

I again felt sorry for him. Was it so bad what happened? I was just helping out a friend, right?

"It's okay, Jeremy," I finally managed to spit out. "As long as you got what you needed and this is the last time you ask me to do something like that, then I don't mind."

"Wow, thanks, man. You're really a great friend, Ash."

"No problem. What are roommates for? But now I'm gonna go get cleaned up."

"Sounds like a good idea," he said chuckling a little. "Sorry about all the jizz. That's the first time I came in days."

I let out a hesitant laugh and headed for the bathroom. I stripped my thong off and looked in the mirror. Jeremy's cum had already started drying on my skin, leaving crusty patches all over my face. I looked down. My dick was still as hard as ever. So, I took out a bottle of lotion and squirted some in my hand.

Slowly, I began jacking myself off. I couldn't help but think about Jeremy's huge cock while I did. Although degrading and wrong, the whole situation was a little erotic. The feeling of doing taboo things with my roommate, being treated like a dirty slut, being used and dominated by a big strong man, it all made me really horny for some reason.

It didn't take long for me to cum. Once I did, I hopped in the shower quickly and washed my roommate's cum off my face. Then I toweled off and went back to our room. Jeremy was already sound asleep so I quietly got into my bed and passed out, nervous about how awkward the morning would be.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
19 Comments
mic1980devmic1980dev3 months ago

fucking hot, cool written , please more, more facials suck and fucking, love it

dominanceaddict1dominanceaddict1over 1 year ago

Sad that this ended after 1. Great

AnonymousAnonymousabout 4 years ago
More

This sorry is awesome more please!!

AnonymousAnonymousover 7 years ago
What an asshole

I would've punched him in his Jimmy and left him crying

AnonymousAnonymousalmost 8 years ago

Hope you continue this.

Show More
Share this Story

Similar Stories

Party Slut Never fall asleep at parties!in Transgender & Crossdressers
Changing Room Prank Mark and Greg help me discover myself with a harmless prank.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
Drink or Dare A drinking game with new friends changes everything.in Transgender & Crossdressers
More Stories