I was never the biggest ladies man in high school but when I got to college I saw an opportunity for a fresh start. To give you guys a picture I’m 5’10, and I weigh about 140 lbs. Just an average dude who’s kinda skinny. My roommate was a guy named Alex, super friendly dude. An athletic type, muscular, 6 ft and a good looking black dude. He grew up next to the University, so he knew the campus pretty well. He even gave me a tour of the city, showed me all the cool restaurants and even outdo out his favorite clubs. I never went clubbing in high school, but I figured I would try it. All I’d need is a fake ID, and Alex said he’d help me out.

All of the sudden someone ran up to Alex and hugged him. Then as they stepped back, I got a good look at them. She was unbelievable!! Her face was a shining tan tone, and her lips were intensely red. She had a cute button nose and big beautiful blue eyes. Her dirty blonde hair flowed down to her shoulders. Then I examined her body. That was the true masterpiece. She had huge pornstar tits and a slender waist that extended at her hips. She knew she was gorgeous the way she had such an air of confidence in the way she walked and dressed. A transparent crop top and the shortest short shorts!! But anyways enough fantasizing lets sea back to reality.

“Hey, Lilly! How was your summer?” Alex asked.

“Incredible, I’ll tell you all about it later. By the way who’s your new friend?”

“Oh right! This is Jake,” he said.

“Nice to meet you, Jake, I’m Lilly.”

I froze. “Nice to meet you too,” I said nervously.

“Okay, well, I’m setting up a party tonight. You guys are welcome to come.”

“Cool sounds like a plan,” Alex said.

“Okay see you tonight,” Lilly said.

“See ya,” Alex said.

“Yeah, see you tonight,” I said.

As she walked away, I couldn’t take my eyes off her ass, so pert and round, and hang out of her shorts. Alex interrupted my staring.

“Dude, you really need to be more subtle,” he said.

“Yeah, sorry.”

“I don’t blame you. Lilly’s killing dudes left right and center with that bod.”

“You can say that again?”

“Shame, though, no girl can say no to this dick,” he said jokingly while grabbing his crotch.

“Did you and Lilly ever?”

“Oh yeah, I even got the vids on my phone.”

“It’s fine, I’ll take your word for it.”

It’s like I met my opposite, he was athletic, I was a nerd, he was a socialite, I was a loner, he was a ladies man, and I had never even kissed a girl. Despite my jealousy of him, he was still a nice guy, and I liked him.

As we were getting ready for tonight, I saw his box of condoms on his desk, on it, the text read Magnum XXL. I had never worn a condom before, so I felt like trying one on. I went into a free toilet and made myself hard, I just thought about Lilly. Then I tried on the condom, and it just dangled off my dick. It was way too big! Surely he wasn’t that much bigger than me! Oh well, maybe he’s just freakishly big.

I decided that if I planned on getting lucky tonight, I needed some protection, so I went to buy some condoms. So I just went to the pharmacy an bought myself a pack. As soon as I came back, we took off for the party.

We were greeted at the door by Lilly. “Hey, so glad you guys could make it! Can I get you guys a drink?”

“Yeah sure,” Alex said.

We followed Lilly to the bar. Alex whispered to me, “If you wanna fuck Lilly tonight you’re gonna have to be more confident, order something strong but don’t get wasted.”

“What do you guys want?” she said.

“Just a beer,” Alex said.

“I’ll take a glass of whiskey,” I said.

“Ooh, who knew the new guy was so classy! A whiskey, a beer and a vodka martini,” she ordered.

We got our drinks.

“Well I’m gonna go fuck some of these babes, I’ll see you guys tomorrow,” Alex said as he left.

“Ugh, I love Alex, but he is such a douche sometimes,” she said.

“Whatever, it’s college, if he isn’t gonna fuck now when else is he?” I said.

“Good point, what about you? What are you like with girls?”

Shit, I couldn’t tell her I was a virgin.

“Well I only had one girl, and it was from my Freshman year right up until graduation, she went to uni across the country so we thought it would be best to stay friends.”

“Damn, that’s impressive. I couldn’t keep a relationship to save my life,” Lilly said, “Anyways, do you wanna go dance?”

“Yeah, sure.”

We started dancing with each other until she began to pull us closer together until she went for it! I couldn’t believe it this gorgeous girl was making out with me!

“Let’s take this upstairs,” she said.

She dragged me upstairs and went into a bedroom and locked the door. She threw me onto the bed and proceeded to remove all her clothes. I stared at her incredible body! I couldn’t believe this girl wanted me!

“Your turn,” she said

I removed everything except my underwear. I went in to make out with Lilly, and she pushed me away.

“EVERYTHING,” she said.

So I removed my underwear and saw her trying to hold in her laughter. As soon as she saw it her hands rushed to her mouth.

“Is it hard?”

“Yes,” I said shyly and embarrassed.

“Oh my god,” and she just burst out laughing. “That’s such a pathetic excuse for a cock!”

I couldn’t say a word, I was so humiliated. I felt like a failure as a man. Not good enough for that woman, I just watched as Lilly couldn’t stop laughing.

“There’s no way I’m fucking that, but I guess I can give you something else, trust me you’ll enjoy it but first let me get pictures.”

“What? Why?”

“To show my girlfriends, of course.”

“No way! I won’t have a chance with them if you do that.”

“If you let me, I’ll be your girlfriend.”

“Wait, what? I thought I was pathetic?”

“You are,” she said, “and you’re never gonna have any girl ever, so accept it. You can be my cuck.”

“What’s that?”

“Well, we’re a boyfriend-girlfriend couple except during sex you jerk off to me fucking other men.”

“What?” I asked stunned.

“Let’s try it, I’ll go get someone!”

She put a towel around herself and walked outside. I put on my boxers and waited for her. She returned two minutes later with some guy. Tall, buff, tanned guy with long her to his neck.

“Jake, this is Rob—Rob this is my new boyfriend, Jake.”

“Hi, Jake.”

“Who the hell is he?” I asked

“This is a guy I fucked last year, it was pretty great.”

“Why am I here?” Rob asked.

“I’ll answer that later, first get naked.”

Rob did as she said, removing his T-shirt to reveal his bulging abs and then his trousers. As he removed his underwear, his huge hard cock popped out! It put mine to shame!

“Now my turn,” Lilly removed her towel and showed off her perfect body. “Now your turn, cuckboy.”

“No way,” I said.

“Rob, remove his underwear.”

“Yes, ma’am,” Rob said.

I tried to run but his big arms grabbed me, and he threw me on the bed and held me down. He was so much stronger than me, there was nothing I could do. He then pulled off my underwear and revealed my pathetic excuse for a dick. He began to laugh, and so did Lilly.

“It’s even smaller than I remember,” Lilly said and keeps laughing. “Now because you disobeyed me I’m gonna punish you.” Lilly took my clothes and threw them as far as she could outside the room. “Unless you want the party to know you have a baby dick, you’re stuck here.”

I gasped. “You can’t!”

“Now now, babe, calm down. Sit over there,” Lilly ordered.

I did as she said.

“You’re a very sweet guy,” she said, “that’s what makes me want you as my boyfriend but because you’ll never please me with that stub I need someone else—like Rob.” She began to caress Rob’s huge cock. “Now, time for you to admit that Rob is an Alpha male and you’re just a Beta Bitch!”

“Rob is an Alpha male, and I’m a Beta bitch,” I said shamefully.

“Now watch what a real man can do to me.”

She begins to make out with this god of a man and slowly moves her mouth down until she was on her knees. Her mouth begins to kiss his dick until she fully loops her mouth around the tip. In one quick swoop, she sucks the whole thing down her throat, and I begin to hear gags. She then removes her mouth from his cock and lies down on the bed with her legs wide open.

“Wait, Jake come here and lie down on this side of the bed.” I do as she tells me. “When we begin fucking you start jerking,” she ordered.

Surely enough, Rob forces his monster cock into Lilly’s tight pussy, and I tug my little penis with my two fingers while Lilly screams and squirts all over Rob. It doesn’t take long for me to release two tiny drops of cum from my penis. Meanwhile, Rob saw me while he was plowing my ‘girlfriend’ and laughed.

“Looks like the loser enjoyed the show,” Rob said.

Lilly looked over. “Wow, that was quick,” Lilly said, “and talk about a small load! I’m sure you can go for a few rounds, Jake. Rob here has quite the stamina.”

As I kept jerking off and instantly cumming to another man fucking my girlfriend, I found my eyes more and more glued to Rob’s cock. It couldn’t be? It was turning me on! Instead of wanting to be in Rob’s position I wanted to be in Lilly’s!!

After my eighth load Rob finally pulled out his huge cock and release a giant load all over a Lilly, and even I got a fair bit on my face and body.

“OK, Rob, as usual, it was amazing, but I wanna talk to my boyfriend but don’t worry I’m sure he’ll still need you to do his job for him.” She passionately kissed Rob, and then he walked out.

“Did you enjoy that?” Lilly asked.

“No!” I lied. “It was humiliating as fuck.” I loved that part. “Your boyfriend got cum all over me!”

That was the best part!

“Don’t lie, you loved it! You’re a closet faggot who loves it when girls humiliate him,” Lilly said making me blush. “No need to answer, your face says it all.”

“Fuck you!”

She looked at me with rage, she grabbed my arm. I tried to pull away but even she was much stronger than me. She dragged me outside naked into a room full of girls, thankfully none that I knew. They all laughed when they caught sight of my penis, and they even took some shots of it with their phones.

“This loser is my boyfriend!” Lilly announced.

The girls gasped.

“But he can’t understand why I need a real dick to be satisfied!”

One of Lilly’s friends grabbed a small plastic device and tried to put it on my penis. I moved away.

“Girls! Grab the loser!” Lilly said, and one skinny and bushy gorgeous girl grabbed, and even her tiny biceps were holding me in place.

“Haha, your boyfriend’s pretty pathetic Lil!” She said.

“You should see him jerk off!” All the girls laughed.

The other girl now placed the device on my penis, it was now completely locked away.

“Guess he won’t be doing any jerking off for a while.”

“Time to teach him a lesson,” Lilly said, she then proceeded to shove her pinky up my ass!!

“Whoa!” I yelled.

“Oh come on it’s only my pinky, you can barely feel it.” She said

“I guess.”

“Now think of my pinky as your penis, small, thin and well pink, except it’s slightly smaller than my pinky,” she said

“Is that what women feel when I’m inside of them!! Oh god!” It was nothing! I finally began to understand Lilly’s point of view.

“I think you’re beginning to understand! But just to be sure” she walked away and opened a closet.

I saw her with two huge strap-ons, I thought to myself that there was no way she was going to do this.

“Are these good?” Lilly’s friend asked.

“Yea, they might hurt but whatever.” Lilly’s friend put on the strap-on and passed the second one to Lilly. She held the monster dildo next to my tiny cock, and the room laughed. She removed my chastity to exposed my pickle sized boner. “You know Jake, I really like you. You’re sweet, cute and submissive as hell. Just because I will never have sex with you, doesn’t mean I don’t love you. You have to understand some are sex machines, like Rob. They’re built as the perfect love makers, you are the complete opposite, so you need some help to do the job of pleasing me. Just look at your dick versus this, it’s not even the size of the tip. Size matters and I want you to see why.” She put on the strap-on. “Now on your hands and knees, mouth wide open.”

“Yes, ma’am.” I obeyed.

“Andrea, shove that dildo in my bitch’s mouth!”

“Maybe he should ask politely first.”

“Plea,” I said.

Lilly grabbed my marble sized nuts and said “YOU FUCKING BITCH!! SHUT UP UNLESS YOU’RE SPOKEN TO!!’

“Yes, ma’am.”

“Good boy, now beg, beg for that dildo.”

“Please let me have it in my mouth.”

“Get on your knees bitch and suck it,” Andrea said. I put the tip in my mouth and sucked a small mouth full of the dildo. “Hah! Call that a BJ!!” She then forced my head onto it and shoved the entire shaft down my throat. I couldn’t move, I was too weak. Tears began to fall down my cheek because I was choking, but somehow I loved it. “Awww, Lilly! Your bitch is crying.”

“I can fix this.” She proceeded to pick up her jeans and remove the belt. She stood back and lashed her belt at my back! Thankful the metal was in her hand but still… the pain was unbearable. She then grabbed a baseball bat from out of nowhere and threatened “Now bitch! Get on all fours and if even an inch of that cock slips out your mouth, bye bye baby dick!” she held the bat again my nub, “I know it’s a small target, but I have three strikes before I’m out.” I carefully got on all fours and firmly pushed my lips against the base of the strap-on. “Alright here comes a big one!” FUUUUUUCCCCCKKKK! Lilly had no mercy with her strap-on, she slammed right up my ass into my stomach, and instantly my dick dripped out a tiny load of cum.

“Woah! you’re bf just precame!”

“Nope, that’s his full load, tiny penis tiny load.”

I think I let out six tiny loads of cum before we ended.

After that,, Lilly and I went into her room, and I was completely silent until she broke it. “You know the silence thing was just me going overboard, you can talk to me, I’m still your girlfriend.”

“OK… Well, can you help me get my clothes?”

“Sure here’s some underwear and jean shorts.”

“Are you serious?”

“You’re probably the same size as me and don’t worry about anyone seeing you’re bulge.”

“I can’t wear a girl’s clothes!”

“No one’s there, and if they are there tell them you’re going back up to fuck Lilly Carter, that’ll shut them up. Also baby sized your condoms are in your clothes.”

“But you said we would never fuck!”

“You want me to change my mind?” I instantly put on her panties and shorts, and they were loose because I don’t have Lilly’s curves but whatever. I ran down an outside grabbed my clothes and went back to the room. Dropped my pants and got ready to lose my virginity!

“Alright, let’s get this over with.” She whined. My dick was instantly hard, I approached her. “Woah! Condom dude, I don’t want my kids to have tiny penises!” I put on the xxs condom, a little loose but I didn’t care. I shoved my dick inside Lilly, she giggled. I kept trying to please her until I came, in under one minute. “Well, I guess you’re not a virgin anymore so congrats.”

“Thanks, babe, that was amazing.”

“To be honest, you did make me laugh, so it wasn’t too bad.”

“Was I that bad?”

“Yes, that was without a doubt the worst sex I’ve ever had in my life.”

“If I was the worst, then who was the best?”

“Actually, your roomie, Alex.”

The End.