Matters of Size Ch. 01

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Matters of Size: Prom Night

******CHAPTER 1******

Back when I was in high school, I wasn’t exactly what you would call a “player.” In fact, I don’t even think I really understood how sex worked until eighth grade, when they forced us to take a sex ed class. It’s not that my parents were conservative—I wasn’t sheltered at all—and I wasn’t a dork either. I had plenty of friends, and I was the best runner on the Track team. In retrospect, I think several girls had crushes on me—but I was totally oblivious.

Which ties directly to my chief problem: I’m really shy around girls. I mean REALLY shy. To give you some perspective here, a girl at a bar once asked me if I wanted to go back to her place, and I responded by explaining that I didn’t get into cars with strangers. So, yeah—needless to say, I wasn’t exactly a “go-get-’em” kind of guy when it came to women.

Being as shy as I was, it wasn’t hard for me to maintain a low-profile among the girls at my school—and I managed to keep from so much as kissing a single girl even once. Until, that is, Prom rolled around. Like I said before, I was a fairly popular guy, and all of my friends had dates. I would look like an idiot if I went stag, and staying home was out of the question. I began to ponder whether I should ask a girl (despite my shyness, I had plenty of female friends), and if it weren’t for Megan, I would probably still be wondering.

I had known Megan for several years, and in fact she was one of my best friends. It had taken a while, but over time I had overcome my shyness around her, and she was one of the few females I could really talk to–so I guess it’s not too surprising that she would ask me. By the time she did, Prom was right around the corner, and I knew I probably wouldn’t get another chance–but even if I had, I probably would have accepted anyway.

As Prom crept closer and closer, Megan became increasingly excited. I was more on the stressed side—I had never even been close to having a girlfriend, and I really didn’t know how to act. It did seem weird just how excited she was, though—I don’t think she stopped talking about it once.

Finally, after all the wait, it was time. I got a bouquet of flowers, I picked her up on time, and everything went great. I was probably a little awkward at first, but eventually I loosened up, and we had a great time. I drove her back to her house, and I thought that would be it. But she paused before getting out of the car.

“Hey,” she said, “why don’t you come in and hang out for a little bit? I’m sure your parents won’t mind.”

“Maybe not, but won’t yours?” I replied nervously.

I hadn’t expected anything like this.

“No, they’re out of town for the month. Come on, it’ll be fine,” she insisted.


I figured I might as well.

“Alright, if you say so.”

I parked the car in her driveway, and followed her into the house.

“My room’s upstairs,” she said casually, “Just wait a minute while I change into something more comfortable.”

I was a bit more relaxed now, and I made my way up to her room. It was medium sized, and very tidy. I couldn’t help but notice, however, that a stray pair of panties had fallen just beneath the edge of her dresser. The thought of her panties just lying there—and not on her body—gave me an instant erection. I tried to ignore it, though, and I quickly laid down on Megan’s bed so the panties would be out of sight. I heard the sound of a door shutting somewhere down the hall, and the sound was immediately followed by Megan’s voice.

“Alright, I’m done,” she said, and I heard the door open.

I looked up and opened my mouth to greet her, but somewhere along the line I completely lost track of what I was going to say, and I just sort of sat there, slack-jawed. This was because all she was wearing was a lacy bra and what could only be Victoria’s Secret panties.

“Oh!” she exclaimed.

She smiled and giggled, her ample breasts bouncing as she did.

“Sorry, I didn’t mean to catch you by surprise,” she said unapologetically.

“Um,” I said like an idiot, “What are you…”

She just winked and walked over to the bed. Grinning, she slid on top of my legs, straddling me.

“Come on,” she said, “I know you’re hard right now.”

I’m pretty sure the look on my face was more than enough of an answer, and she reached for my zipper. My heart was racing. What if we had sex? Did she have condoms? Would she enjoy it? I had never done it before, and I was understandably nervous.

She slowly unzipped my pants, and removed the button. She then grabbed the waistband of my boxers, and yanked them down.

She let out a high-pitched snort, and her demure smile changed to an amused grin.

“Uh, is something wrong?” I asked frantically, wondering what could be the matter.

“Oh, well, it’s nothing,” she said, but it was obvious she was just barely able to contain herself.

“It’s just…” she said slowly, “I thought you’d be a bit… bigger?”

She said it like it was a question. I was confused at first. I had always thought Kartal Escort I had an average-sized penis. They had explained the mechanics in sex-ed, but they had never shown us a model or given us any measurements. It had never occurred to me that my penis might be any different than average in size.

‘Uh, what—what do you mean?” I squeaked. “It’s about average, I think…”

Megan raised an eyebrow.

“What about the guys on the Men’s Underwear packages? Do you think they all just have comically huge dicks?”

Megan had more than a hint of humor in her voice.

“Well, I mean, I, uh,” I stuttered, “It’s not that small, is it?”

“Well, I don’t know,” she said, staring at my dick, “I guess it’ll probably be fine.”

“Here,” she continued, turning around on the bed, “You can start.”

For a moment I just stared at her round, beautiful ass. Finally I realized she wanted me to fuck her from behind. Anxiously, I pulled her panties down, and spread her legs apart a bit. I pulled my pants down all the way, and grabbed my dick in preparation. With one hand, I spread her pussy a little, and with the other I pushed it in. I marveled silently at the warmth and slippery softness of her vagina. Megan turned her head back a little.

“Come on, put it in,” She demanded impatiently.

“It is,” I replied, puzzled.

“Oh… I didn’t notice,” she muttered. “Just start, ok?”

I was a bit more comfortable now, and I began to move back and forth, slowly at first, then faster and faster.

“Can you pick it up a little?” Megan asked as politely as she could.

I moved even faster. It felt wonderful—in fact, it was one of the best feelings I had ever experienced. I let out a moan of pleasure and rolled my head back.

“Uh, could you maybe… push a little harder…?” Megan asked again.

She sounded annoyed, so I moved even faster. I must have pulled a little too far back, because all of a sudden, my cock slipped right out of her pussy. I was on the verge of an orgasm, though, so I kept moving, and when I pushed back again my penis poked into her pussy. It wasn’t enough to actually penetrate, but it was enough to make me orgasm, and I let out a loud groan as I ejaculated all over her pussy.

“Oh, man,” I huffed, “That was great!”

“Oh, did you come?” Megan asked, sounding genuinely curious.

“Uh, yeah,” I replied tentatively.

She turned over and looked down at her pussy, and her eyebrows rose in surprise.

“Oh, um… Yeah, I guess you did!” she said finally, almost too enthusiastically.

I must have been frowning because she looked up at me, and immediately continued.

“It’s just that, well, other guys I’ve slept with haven’t been so, uh… messy.”

“But I bet it’s just because you’re inexperienced!” She said quickly, smiling at me.

“Um, okay—I mean, as long as everything’s alright,” I stuttered.

“There’s just one thing I want to check,” Megan said quickly, and she got up and walked out of the room. Despite having just come, my penis became rock hard again when I saw my semen dripping out of her pussy as she walked away. She closed the door behind her, and I was left to my thoughts—which quickly centered on my dick. I stared down at it. It didn’t seem small, but how many dicks had I actually seen? I hadn’t seen any, really. I put my hand next to it. After comparing for a few seconds, I determined that my penis was a little longer than my thumb. That didn’t seem too small.

The door opened suddenly, and in walked Megan. In her hands were her Smartphone and a ruler.

“What do we need those for?” I asked, genuinely curious.

“You’ll see in a minute,” she said distractedly, fiddling with her phone. “I’m just looking something up on the internet.”

I sat there awkwardly, wondering what she was doing.

“Alright,” she said finally, “It says here that according to a study done in America, the average male penis size is six and a half inches. Six inches is below average, Five inches is small, and Four inches is considered a tiny penis.”

“O-ok,” I said, getting increasingly nervous. Those sounded like absurdly large numbers.

“I wasn’t really feeling it just now, so I wanted to use the ruler to see if I could figure out what’s going on—but ONLY if you’re okay with it, of course.”

She paused briefly before continuing.

“You ARE Okay with it, right?” she asked, smiling sweetly.

“Sure,” I said without thinking. “It’s totally fine.”

She nodded and smiled again before turning her full attention to my penis. She meticulously pinched my penis between her thumb and forefinger, holding my erect member straight in line with the ruler. She frowned quizzically.

“Maybe if I push it in a little farther…?” she muttered under her breath.

‘Eventually she shook her head and typed something into her phone.

“Sorry,” she explained, “just making a note of the measurement,”

She carefully put the ruler on her bed-stand before turning back to her phone. A few minutes passed, and I cleared my throat a couple times to no effect.

“So,” Yakacık Escort I finally said, “what was the measurement?”

Megan looked up, flustered.

“Uh,” she said, selecting something on her phone, “You were almost three inches.”


I couldn’t believe it.

Megan looked me straight in the eye, with just the faintest hint of a smirk.

“Your penis is two and three quarters inches long when fully erect,” she repeated matter-of-factly.

I looked down at my cock. It was now flaccid, and it had partially retracted into my body. It looked like I had a second belly button with the tip of a penis poking out. I reached down and tried to push the head out, but instead my penis shrunk all the way into my body. It looked like I just had balls and a piece of skin where my manhood should be. I looked up at Megan.

“You have a really tiny penis,” she remarked nonchalantly.

I didn’t know what to think. What impacts would this revelation have on my sex life? Would any woman want me? I wasn’t sad or upset, but I felt more than a little embarrassed.

“Maybe I should leave,” I began, but Megan cut me off.

“Oh, no, no,” she said hurriedly, “We can’t just let your tiny cock ruin our night together!”

“Look,” she continued, “I pleasured you, now it’s your turn to pleasure me. That sex we had earlier—if you can even call it that—didn’t do anything for me.”

My faced flushed with humiation. She had just plainly said that I had failed completely to satisfy her. It was like she thought that measuring my dick gave her the right to insult me as much as she wanted. I wanted to be angry, but I was beginning to feel strangely turned on by the way she was talking to me.

“Wh-what do you want me to do?” I asked slowly.

“Well, you orgasmed and I didn’t, so I think it’s only fair,” She said plainly, “You are going to lick out my pussy.”

I gawked, not just at what she had requested but that she had ordered me to do it.

Megan raised her eyebrows.

“Unless you can think of some other way to pleasure me with that dicklet of yours?”

“But, uh—isn’t it covered in cum?” I asked, though I knew the answer.

“Yes, it is,” she said, “You made a mess, and now you get to clean it up.”

“Well, can’t I, like—wipe it down first, or something?”

“No,” she snapped, “You have to swallow every last drop!”

I gagged at the thought, and panic slowly began to rise in my chest.

“Why do I—”

Megan cut me off immediately.

“Don’t talk back! Just eat it, Bitch!”

I was shocked—I couldn’t believe she had just called me a bitch to my face. I was angry for a moment, but then I noticed that my cock had emerged and was now standing short and stiff, its head pulsing purple.

“S-sorry,” I said, avoiding Megan’s gaze.

Megan noticed my change in posture and laid back, spreading her legs in front of my face. I stared into her beautiful pink-and-red labia, still covered with gooey white semen. My cum had even made its way just into her vaginal cavity—but not very far.

I bent down and drew my face close to her crotch. The smell of semen and vaginal fluids mixed into a pungent aroma that somehow aroused me even more. Without a second thought I shoved my face into her snatch, rolling my tongue around and mopping up as much semen as I could. Megan began moaning with pleasure almost instantly. Every few licks, I stopped to swallow the cum I had collected in my mouth. It was sticky and slimy, and it took several loud gulps to get each mouthful down.

As I shoveled semen out of Megan’s vagina with my tongue, I discovered that it actually tasted delicious. I became so distracted swallowing my own cum that I didn’t even notice when Megan came, despite her loud wails and wild convulsions. After a few seconds, she sat up and began to stare at me.

“Uh, you can stop now,” she said slowly.

I ignored her, and enthusiastically gulped down the last few licks of cum before pulling my face out from between her legs. I finally noticed her staring at me—she had a huge, unmistakable smirk on her face.

“Wow,” she said, “I really enjoyed that. I think you did too, though I’m not sure which part…”

She winked at me, and I felt my face flush a little.

“Most guys aren’t that good at cunnilingus,” she continued, giggling. “I guess you have to have other skills to make up for that pathetically tiny penis!”

My face reddened with embarrassment, but it felt really good to have her talk to me like that.

“Are you having a good time, little man?” she asked perceptively.

I nodded obediently.

“Well, don’t worry,” she continued, “I’ve got plenty of fun things for us to do—just you wait!”

“Like what?” I asked excitedly.

“Just be patient,” Megan said as she got up and strode to her dresser.

She rummaged through the top drawer for a few moments before pulling something out, and at first I couldn’t quite tell what it was. I watched curiously as she pulled a bottle out of the drawer and furiously squirted its contents Kadıköy Escort onto the object. Finally, she fastened it around her waist then turned to face me. My eyes bulged as a huge, jet-black dong swung around with her, bumping against her leg. It was a strap-on.

“Like it?” she inquired, smiling coyly.

I was lost for words.

“It’s eight inches long and two inches thick,” she continued.

“This is what a real man’s penis looks like. Your pathetic little cock is barely as long as this baby is wide!”

Megan hopped onto the bed, straddling my legs. She grabbed my dick and placed it next to her strap-on, and began to laugh.

“Look at this,” she said, “It’s so fucking tiny!”

I had no idea how to respond, but her abuse just made my erection harder.

“What are you going to do with it?” I squeaked, fearing I knew the answer.

“What am I going to do with it,” she mimicked, laughing. “I’m going to fuck you with it!”

With that she grabbed my legs and manhandled me into a belly-up, spread-eagled position. She reached down, flipped a switch, and a humming sound emanated from beneath the straps. Tightening her grip on my legs, she shoved the strap-on into my anus.

I gasped at the pain that immediately shot through my butthole even as Megan began to moan with pleasure. She had, thankfully, applied copious amounts of lube, but the pain was tremendous. She pounded me relentlessly, pumping the dildo all the way in and out each time.

“How do you like being fucked like a bitch?” she gasped, to which I replied with a loud groan as she shoved the dildo even farther in.

She reached down and began vigorously pumping my tiny erect penis with her thumb and forefinger. She yanked it up and down faster and faster, and my groans of pain quickly turned into groans of pleasure. Megan jerked me harder and harder, and I quickly approached climax. She screamed and thrusted the dildo into me one last time as she came. With the dildo still inside of me, Megan gave me one last stroke and pointed my little dick straight forward, and I ejaculated all over myself. It was the most cum I had ever shot, and string after string landed on my chest and face.

Panting quietly, Megan reached down and switched off the vibrator. She gently pulled out the strap-on, and laid down on top of me. Her whole body was touching mine, and she draped her arms around my head and shoulders in a loose embrace. She licked a long line of cum off of my face before resting her head against mine.

“I really enjoyed that,” she said after a moment.

“Yeah,” I said slowly, “me too.”

“You know,” she whispered, “I always suspected you had a tiny dick.”

I blushed at her bluntness.

“Uh, why?” I asked, wondering who else might know.

“Well, to be honest, I’ve been checking you out since we met,” she explained, “And I’ve never once seen a tent in your pants, if you know what I mean. What really convinced me were those gym shorts you had last year. They were practically skin-tight, but you didn’t have any more bulge than I would have if I had worn them. From a distance, it even looked like you had a camel toe!”

My face went completely red with embarrassment as I considered just how many people might already know about what I had just discovered—that I had a really tiny penis. Megan glanced at my expression and grinned.

“Don’t worry,” she said, “I haven’t heard any rumors about you. Not many of the girls know you well, so your little problem hasn’t gotten much attention.

“Which reminds me,” she said suddenly, and scrambled off of the bed.

She walked to her dresser and retrieved her phone.

“Oh, good,” she said after a moment, “It’s almost midnight.”

I wasn’t sure what she was talking about, but she seemed excited. I was about to ask her what she was talking about when the doorbell rang.

“Megan, I thought you said your parents were out of town!” I exclaimed as I reached for my clothes.

“It’s not my parents,” she replied, snatching them away.

“Now come on,” she ordered, and briskly exited the room, clothes in hand.

I stood there dumbly for a moment, wondering what was going on. Eventually I came to my senses and dashed down after her. Megan’s front door opens directly into her living room, and as I entered it I saw something that stopped me in my tracks. There, spread across Megan’s couches, were no less than six teenage girls, all from my class. As soon as I entered, they all turned to stare at me, and I just stood there, naked and dumbfounded, unable to move. Hoping to retreat, I stepped backwards—right into Megan, who quickly yanked a zip-tie around my wrists.

“Megan! What are you doing?” I asked frantically as she dragged me over to the couches.

She threw me unceremoniously onto the one empty couch and immediately pulled another zip-tie around my ankles. By now the other girls were standing all around us, giggling and snickering as I struggled uselessly. I glanced at the girls faces, and realized that I knew most of them, at least in passing. There was Jasmine the cheer team captain, Samantha the gymnast, Chloe from Statistics class, Naomi (a shy girl from my homeroom), Ellen (she was the valedictorian), Rachel, my hot lab partner—and, of course, Megan. Megan reached down and grabbed my flaccid dick, pulling it up as far as it would go.

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