Aspiring to be Ass-fucked Ch. 03

Make sure you've read the first two chapters before reading this one. Hope you enjoy!

*****

"Come on, Fuck me. What are you waiting for?"

I bucked my ass up towards him.

He leaned forward for a moment but withdrew. He say back in the bad and drew a heavy sigh,

"I'm sorry, Holly. You seem pretty cool but this is all so weird"

I could have leaned forward and kissed the beefy football player, or blown him to loosen him up, but if he wasn't completely into it then it wouldn't be worth it. I started gathering my clothes from the various parts of the bed.

"I get it." I tried to reassure him as I slipped my panties back over my softening penis. "Just promise you won't tell anyone."

"I don't want anyone to know." Al admitted.

I smiled back at him and put my top back over my tits. He finally got his shirt back on and said,

"If you don't mind, could you leave before I do so people don't get the wrong impression"

I walked to the doorway and stood for a moment.

"If you ever change your mind, the offer still stands."

With that I turned my ass to him and tried to make it sway as I walked away.

Failure, but I can't be kept down. I quickly made my way back to the party and found things just as I left them. Lights flashing around revealing scenes of drunk dancers on top of each other. There must be some guy here that doesn't mind fucking a cute little thing like me in the ass.

I walked around the party looking for guys. I wanted someone strong but hopefully open-minded. The second part was the real key. I moved from guy to guy trying to entice them with my lovely lady lumps. Half the guys liked what they saw but were too drunk to pay attention for more than a minute while the other half were "taken".

The party was becoming incredibly frustrating. I was getting tired of the music and I could barely breathe in the crowd of people. I elbowed and squeezed my way through the thick crowd and finally found a door outside. It was a little cold out, especially in the minimal covering that my outfit provided. I could feel my nipples pointing through my sheer top. I sat in a wooden chair on the patio. It was actually pretty quaint considering where I was.

Behind the house was a stretch of grass and some woods. Surprisingly, the party was contained to the house and I only spotted one person outside. At the edge of the grass and the woods was a guy pissing roughly into the trees. He must have been hammered, because he started turning towards the grass, still peeing. I caught a peak of the dick and it's owner. It was Jeremy from my Writing class, and he had a huge dick! I'd never thought about him sexually before, but the more I stared at him the more I realized he was really hot. He wasn't built like a football player but he was in shape and most importantly; much bigger than me. He had short brown hair and a jawline like a movie star.

I decided to say something,

"How's it going there, Jeremy?" I smiled. He seemed surprised for a moment but then continued pissing as if I weren't there.

"Just finishing up." He smiled as the last drops of piss fell. He started walking towards me. "You are...Holly? From Writing?"

"Nailed it."

He put up his hand for a high five, then embarrassingly withdrew when he realized it probably had some piss on it.

"Enjoying yourself?" I asked smugly.

"Oh, I was just pissing on the frat lawn."

"I could see that."

"Yeah."

"Any reason?"

"The stupid frat wouldn't let me in so I wanted to piss on their lawn like they pissed on mine."

"They pissed on your lawn?" I asked.

"It's a metaphor, duh."

"Riiiight. A metaphor was streaming out of your dick just then, huh?" I said sarcastically. "Why wouldn't they let in such a smart guy as yourself?"

"They said I was a tranny fucker and they don't like my kind around there."

The answer shocked me. He said it with such vitriol. He could see the confusion and excitement on my face. There was a moment of silence before I said,

"I hate that word."

"Tranny?"

"Yeah, that one."

"I was just quoting them."

"Well...did you?"

"Did I what?"

"You know...fuck a transsexual girl?"

"Yeah." He scratched the back of his head. "Yeah I did, and I had a hell of a time doing it. I don't really care what those assholes think."

I smiled, I think I ran into a real catch.

"You're very open."

"I'm very drunk." Jeremy started laughing.

This guy was perfect, I decided to sink my claws in. I stood up from my chair and came closer to him. I let my fingers play with the railing of the patio as I inched towards him.

"You know, I think what you did is pretty brave." I drew ever closer to him. I started lightly touching his body, feeling his abs and shoulders. He seemed surprised at first but caught on quickly.

"What was she like? The 'girl'?" I asked as I brought his hands to my body.

"Well, she looked like a regular girl; Long red hair." He brushed my hair behind my ear.

"Skinny." He played with my belly.

"Tiny little tits." He cupped my large breasts in his hands. "Nothing like these."

He looked into my eyes, each of his words turning me on more and more.

He reached for my ass, "A cute little butt."

"And where there would have been a pussy..." He reached for my crotch and felt my cock. I bit my lip and looked at him nervously. His eyes went wide for a moment. I was scared he was about to back off until he leaned in and kissed me. I could taste the beer off his tongue but all I could think about was his big dick ramming me senseless. He held my ass in his hands and and our tongues embraced each other.

"Jeremy." I said in between kisses, almost panting. "I want you to fuck me. Hard."

"What do you say we ditch this party?" He smiled that dumb 'guy' smile.

"My dorm is empty tonight."

He didn't hesitate for a moment. He took me by the hand and started running.

"Where's your dorm?"

"Leopold Hall, Fourth Floor!"

I called out from behind, laughing. Between the thought of being rammed and the full speed sprinting, I was running out of breath.

The first floor of Leopold had a lounge where some people were hanging out. We stopped running while we knew there were people around. Once we got to the elevator, I clicked the 4th floor and made out with Jeremy. The floor dinged and we made our way to my room. I fumbled to find the key card while Jeremy kept kissing me. I finally got it and entered the door. Thankfully Michelle was nowhere in sight.

Jeremy picked me up and brought me to the bed. His kisses traveled from my mouth down my body. He removed any obstacles in his way. Off with my top as he caressed my tits. As he approached my cock I undid my jean shorts and thew them somewhere into the room. He slid my panties down my legs and threw them somewhere as well.

My small little rock hard dick pointed right at his face. Before I knew it his head was down on it and bobbing like a pro. I'd never gotten a blowjob from a guy before, but Jeremy really seemed to know what he was doing.

It felt amazing having his mouth engulf my cock but I stopped him and said,

"Why do you get all the fun?"

I leaned up so I could start undressing him. Off went his shirt, revealing his impressive abs. I struggled to get his jeans off because of the big bulge at the top. He helped me out and I finally I was able to get his underwear off too. He huge dick flopped out of his boxers. I couldn't take my eyes off of it. It was the most beautiful thing I'd ever seen.

"It gets even bigger." He said.

My eyes grew wide and I dove head first into his cock. It felt good having his warm shaft in my mouth. I had my lips half way down before he said,

"You can do better than that." and he forced my head down on his cock, getting close to the back of my throat.

I tried to moan a sound of approval by I think any noise I made was muffled by his dick. As I bobbed on his cock he leaned forward and spread my ass cheeks apart in his hands.

"I can't wait to fuck this."

I tried to show my infinite approval by taking his cock even deeper into my mouth. I brought my head up for a quick breath and noticed that it was in fact even bigger than it was when we started. My head went back on his cock and he started rubbing his fingers around my asshole.

At first he teased it by just sticking the tips of his fingers in but he gradually put more and more in. His entire middle finger rummaged around my ass. It felt so much better that my finger ever had, because I knew I had no control. He stuck two fingers in and I brought my head back up to moan loudly.

"That's it, Holly, I've got to fuck your ass now." Jeremy said.

I removed my mouth from his cock and turned around on my knees so fast I was worried I scared him.

"Haha, you really want to get ass fucked, don't you?"

"You have no idea."

"Hmmm, maybe I shouldn't." He teased his cock around my butt, I could feel my own saliva on my backside. "No condom, no lube, no nothing. Maybe this isn't such a good idea"

The teasing was killing me, "Jesus Christ, Jeremy, would you fuuuuuuukkkkk."

I held out the last word with a moan as he suddenly thrust his cock deep in my ass.

"Oh my fucking god, yes. Keep going."

I felt like a bulldozer was thrusting in and out of me relentlessly. I'd been training for a year but nothing could prepare me for a cock that big going deeper than I thought possible. My hole was stretched and almost resisting as he pumped in and out.

"You're a little tight." He said. "We'll have to work on that."

I could barely say anything as the pleasure overrode my body. All I could do was moan and moan louder.

"Everyone on your floor is going to hate you." He laughed.

"Good."

As he fucked me I felt my own cock start to tingle. No one had even touched it and I felt like I was going to explode.

Just as it seemed I was going to need to buy new sheets tomorrow, I heard the door open and looked back to find a drunk Michelle and Chris stumbling into the room.

My first thought was; Shit, what the fuck, Michelle. And my second thought was; what if she sees my dick? Luckily from the angle Jeremy was fucking me, she couldn't see anything but his well toned ass.

Jeremy paused briefly and looked back. He seemed to recognize Chris.

"Chris?"

"Jeremy?"

"How's it going?" Jeremy asked.

"Uh...good I guess."

At that, Michelle took Chris practically by the cock and said,

"Why don't we let Holly and Jeremy enjoy each other a little bit."

Michelle winked at me as she closed the door and went off to bang Chris somewhere else.

Once the door was completely shut, Jeremy just shrugged and resumed fucking me. He had to be the coolest guy I'd ever been with.

The intrusion was a bit jarring however, and I had lost the momentum from the would-be orgasm I was going to have. I soon felt it building up again however. I moaned loudly as he pounded me even harder.

"I. am. going. to. cum." I tried to say between his thrusts and my own moans.

He slammed into me harder than ever, his whole cock in my hole. With every thrust his balls hit my taint and I felt my cock start to spurt cum all over my sheets. I nearly screamed as I came and Chris seemed like he was about to stop.

"Don't you fucking stop until my ass is leaking cum." I said authoritatively.

He smiled and continued ramming me. His thrusts started to feel more deliberate and I could feel him tense up until he finally shot his load inside my ass. He kept thrusting for another couple seconds before pulling out. I could feel his white seed dripping down my asshole. He collapsed on the bed next to me and gave me a kiss. I couldn't smile harder if I tried. He seemed satisfied too as we laid down next to each other, catching our breath.

"You have an incredible ass, Holly."

"And you have an incredible cock."

"Round two?"

"Round two!"

At that, he started to get up but seemed to have trouble moving. Being the hero that I was, I told him to stay down and I positioned myself over his cock. He slid into me and we went at it again. This time though, when I came, my cum hit his face. I was about to apologize but he stopped me and brought my face close to his and had my lick my own cum off of his face. It was salty and gooey and oh so delicious, I don't know how anyone could resist swallowing it.

Chris came again and this time he actually seemed spent. He laid down on the bed and practically passed out. I cuddled up in front of him and fell asleep.

***

I woke up before Chris did, and I was worried he was too drunk to remember last night. At the very least he would be hungover. He didn't give me too much time to think though, as I saw his eyes open.

He sat up on the bed and looked at me. We were both naked and I saw him scratch off some dried cum off his chin. I must have missed a spot. He looked at me.

"Holly." He seemed to be reminding himself.

"Yeah?"

"I'm not crazy, right? We fucked last night, didn't we?"

"Yeah, we did. It was really good." I smiled.

"Good, that's how I remember it."

I got up from the bed and walked to the fridge. He saw my dick as I went to get him some water.

"Oh, right. Yup, we definitely fucked." He smiled and I smiled back.

I came back to the bed and gave him some water.

"I had a really good time last night. You're really hot and you're damn good in bed. I'd really like to do this again."

"Oh Holly, I had a good time too, but I'm a little hung over now."

"Not right this second, you idiot." I playfully punched his shoulder.

"Ouch. I'd like to do this again too, but preferably with less alcohol involved."

"Agreed."

"What do you say I gather my clothes back and sleep in my dorm for the next 88 million years, and you and I get dinner tonight."

"Only if you give me a little treat after." I teased.

He smiled his 'dumb' guy smile.

I kissed Jeremy goodbye and started gathering my clothes from the four corners of the room. All my dreams had come true last night I wanted more. Jeremy was perfect.

I realized I was tired too, so I slipped on some sweats and fell asleep.

I woke up to the sound of the door opening. Michelle walked in.

"Hey roomie, you had a fun night." She practically winked.

I forgot she walked in on us last night and I had hoped she would be too drunk to remember.

"So did you." I responded.

"I really did. But Chris is old news, that guy you were with was cute. How'd you bag that?"

"It's a long, strange story. Anyway, we're going to see each other again."

"Way to go Holly. He wasn't weirded out by your thing?"

"My thing?"

"You know." She whispered and pointed down at her own crotch. "Your...dick."

"You knew about that?"

"Holly, sweetheart, it's a dick, it's kind of hard to hide when you're only in panties."

I wondered how long she knew. Come to think of it she probably knew the first day she saw me in just panties. I figured the awkwardness between us when I first arrived was just because we were both new.

"I guess I didn't know why I thought you wouldn't notice. He was totally cool with it."

"Wow, what a catch. I see a lot of double dates in our future!"

I smiled at Michelle. For all her faults, she really was a good roommate and friend.

Just then I got a text from Chris.

-Jeremy wants your number and snapchat. Should I give it to him?

-Yes.

A minute later I got a text from Jeremy saying it was him and what the dinner plans were and then I got a snapchat.

I opened it up so see a picture of Jeremy's dick hard as a rock. The caption read, "Ready to get fucked?"

I responded with a picture of my asshole and the caption,

"Always."

The End...for now.

*****

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