Re-edited by me, originally written by JealousBoy
“Oh… It feels so good!”
“Take it take my big cock. Yeah, you like my big cock don’t you?”
My name is Emily. I’m a 24-year-old grad student. My boyfriend Jake is a world class jerk. We met in college. I was a cheerleader and he played basketball (although he wasn’t really a great player). The first time we had sex was really interesting. We had gone to a party together and I had gotten pretty drunk. Jake had been bragging to a few of the guys about his “big dick” (of course there were girls around too) so on our way back to his place I was sincerely curious.
He wasn’t lying.
We undressed in his room. He peeled my bra off. He was pretty rough with my breasts.
“Damn babe. These are nice.” he massaged them in his hands. I’m not a particularly big fitted girl but at 5’6″ 100 lbs 32B can look large. He was obsessed with my tits which led me to think that he was a boob guy.
I squatted down to unbuckled the jeans of his belt. When his jeans dropped to the floor I saw a pair of red boxer briefs with a big bulge.
“Are you ready for a big monster?” he said.
I quietly nodded and reached in the waistband slowly bringing the underwear to the floor. Now I had been with a few guys before Jake so I had some idea of big and small. All of my boyfriends since Middle School had gotten progressively larger in the dick department. Jake was no exception. His dick was impressively hard. It stuck out with a slight downward curve, which was perfect for my body. I took hold of it.
“Yeah, babe… Seven inches all for you.” he moaned.
I remember thinking, “Wow… Seven inches, really?”
I bounced on his dick for most of the night so I was fairly sore for the next few days. Over the next two years, we became long term boyfriend and girlfriend. We moved in together while I started grad school.
During this time I had kept in really good shape. Jake on the other hand just kept hanging out with his college buddies. They went drinking almost every other night. I don’t think it’s shallow to lose attraction for a partner, like when Jake lost his tight abs. He holds me to such high standards that I think it’s only fair. While he didn’t have a beer gut I have to say nothing was hotter than a pair of ripped abs for me.
As for his dick, it was the biggest I had been with but I also learned that he wasn’t exactly seven inches it was closer to six and three-quarters but it was still huge compared to my previous boyfriends’. As his gut grew though his cock became less stiff and lost even more size.
Now, back to the present…
I was riding my Jake on our bed. His big dick felt so good after not having it for a few days.
“Oh, you feel sooo big!” I lied, moaning as I bounced on him.
He picked me up and started driving deep inside me before he dropped me back on the bed. Now, on my back, he pummeled away at my pussy.
“You like that deep don’t you?”
“Ahh, you’re so deep!”
“Oh, babe! I’m gonna cum!”
It didn’t happen all the time but Jake usually made a point of cumming whether I did or not. In this case, I had not. He finished up and rolled over entering a snoring slumber just a few minutes later.
I laid in bed staring at the ceiling. Tomorrow Jake and I were standing up in his cousin’s wedding. Maybe he’ll think about a proposal. I thought dreamily.
We arrived at the estate the next morning. Jake’s cousin was getting married at a beautiful country estate that overlooked a private lake. I only met her a few times but she insisted that both Jake and I stand up in her wedding.
We had met most of the wedding party before. Some of them were Jake’s cousin’s others were just friends of the bride and groom. This afternoon would be reversal, prep, and a dinner. Then tomorrow morning would be the actual wedding.
The bride’s parents were surprisingly strict so all non-married couples had to share a suite with others in the party. I shared a suite with a girl named Kelly. She was the sister of the bride’s best friend. Kelly was a pretty girl. About 5’7” really thin with long blonde hair. She had just turned 19 and I could tell she had a bit of a wild streak. For example, when she unpacked her suitcase I noticed slutty black lingerie.
“What did she think was gonna happen at this wedding?” I thought to myself. I wouldn’t consider myself jealous, more like just apparent self esteem issues. Jake surely doesn’t help with that either with all his joking around.
Across the hall, Jake shared a suit with the younger cousin of the groom his name was Kyle. Kyle had just had his eighteenth birthday a few weeks ago. I know because the bride thought it would be good if all of us gathered to meet each other. I knew then that Kyle had a thing for Kelly. Even though Kelly seemed to shrug him off (she was probably interested in older guys) maybe that’s what the lingerie is for. I thought.
I unpacked my things and walked over to Jake and Kyle’s room. Jake was sprawled on his bed watching a game on TV. Kyle was quietly unpacking his own things. I noticed that Jake’s things were thrown all over the floor.
“Uh, are you even gonna keep this room clean?” I asked him holding my hands on my hips.
“Why? It’s not like you or I have to clean it up,” he responded without taking his eyes off the TV.
We had fought most of the way up. Mostly it regarded his laziness both at work and at home. He seemed more interested in his video games or his newest sports magazine than our relationship or our apartment (or future for that matter).
“Whatever. Nice to see you, Kyle. Don’t take any tips from him.” I turned and stormed out.
I sat in our room and stewed for a while expecting Jake to come in and apologize. He didn’t. Kelly came out of the bathroom in a skimpy pink bikini that hardly covered her smallish but firm boobs.
“Uh… Did you want to go swimming?” Kelly awkwardly asked me, it was obvious she wanted Jake to come. Kelly would rather I drown.
“No thanks,” I responded.
She turned and walked across the hall. I listened, expecting her to ask Kyle to head down to the pool with her.
“Hey Kelly,” said Kyle.
“Hi, uh, Jake. Do you want to go swimming with me?” She asked blowing Kyle off.
That little bitch. She wanted Jake, not Kyle. I was furious. He better know what’s good for him I thought.
“Yeah sure. Lemme grab my trunks.”
“Ok, great. I’ll see you down there,” she said and skipped out of the room and down the hall.
I heard the bathroom door close. By the time it opened back up I was standing outside with my hand on the door frame.
“What do you think younger doing?”
I was concerned to say the least. This slut Kelly obviously was eyeing my man. She probably wants to hook up with an older guy to show off to her air-headed friends.
“I’m going swimming. Isn’t that obvious?”
“Without your girlfriend and with another girl?”
“Whatever. You need to loosen up Em.”
“What the hell? Loosen up? What would you think if I went swimming with Kyle alone in a skimpy bathing suit?”
He glanced back at Kyle’s shaggy hair and thin frame and began to smirk.
“Go for it,” he said while walking away.
Jake followed Kelly down to the pool. I could feel the rage building within me. I stormed out of the suite. I considered following in my own bikini. My tits were definitely bigger so maybe I could flaunt those to the other guys. What was I thinking? This isn’t me. I sulked for a little while.
Eventually, I calmed down and convinced myself that Jake was just under a lot of pressure and that him hanging out with that girl at the pool didn’t mean a thing. Still, I walked down to the pool to do some harmless spying.
Just as I go around the corner I saw Jake and Kelly being suspicious. He had his groin pushed tightly against her tight bikini bottom smirking as he ground against her. I knew exactly what he was doing.
“Yeah, babe. That’s all me,” he bragged.
“No way,” she whispered. “It’s like…huge. Definitely bigger than my ex.”
I was pissed. I stormed off to walk by the lake. Half an hour later I convinced myself that Jake just liked being a bragger and the incident in the pool didn’t mean anything.
By the time I made it back to the estate the sun was just beginning to set. I started walking down the hallway to our suite and noticed Kyle sitting on the floor outside of his suite knees bents chin rating on his knees.
“Uh, Kyle. Why are you on the floor?” I noticed a towel in his hands.
“Jake told me to give them some space. I just wanted to shower before dinner tonight,” he said.
“Some space? Wha-” That’s when I heard the muted moaning through the door.
“Are they… Are they fu-screwing in there?”
“Uh… I guess. Jake and Kelly went in there a little while ago. I was just about to get in the shower.”
I pulled him off the floor.
“Come on.” I took him by the hand and we both crept into the suite. Sure enough, Kelly was riding my boyfriend. Her legs spread as she bounced on his big dick. Her tiny tight exposed, jiggling with each bounce. Her eyes were shut and so were Jake’s. They had no idea we were there.
“Oh fuck, oh fuck! You’re sooo deep, it’s so deep. You’re really big. Oh shit!” Kelly moaning like a slut.
I was furious but I calmed a bit when I noticed Kyle’s eyes begin to show signs of watering at the sight. I turned and both Kyle and I walked out of the room.
“Ok, well. Kyle, you can use our shower, I guess. I’m going to go downstairs to give you some privacy. I’ll be back up later.” I walked away feeling surreal.
I’m not sure if Kyle took my advice but I went down to the bar. I ordered a glass of Merlot and sipped it. It sent down pretty fast. I’m not sure just how much time had passed but it felt like an eternity.
I went back upstairs. The door to Jake’s suite was still closed. I could hear his grunting along with her squealing. He was probably giving it to her doggie by now.
I turned and opened the door to my own suite forgetting the Kyle may be in there. I was shocked at what I saw.
Kyle—skinny shaggy haired Kyle—was on the edge of my bed, sitting on his towel. Using both of his hands to beat off the biggest cock I had ever seen. All I could do is stand in the doorway with my mouth hanging open.
“Shit!” He released his humongous cock from both hands and it hit his tight abs with a heavy audible “thud”. The giant head was oozing as it rested just below his nipple line.
He quickly pulled the towel over his groin trying to cover his massiveness. Like a thin towel could seriously cover up that obscenely big dick.
“I’m really, reeaally, sorry! It’s just… Well, I thought… you were gonna be a little longer. I’m sorry.”
I couldn’t take my eyes off his groin. Even though he pulled the towel over his ridiculously large teenage cock the towel failed to reach up passed his enormous plum-sized cock head.
“Uh, your…” I gestured to his chest where his monster lay oozing his thick juice.
He looked down.
“Oh,” he quickly covered the thick head.
Jake had always bragged about his size so naturally, I thought he was as big as they come. I mean I knew there were bigger out there but not like this. Kyle’s cock was easily two inches longer than my boyfriend’s but wasn’t the most impressive part.
It was the width or the crazy thickness. Jake always shoved his dick in while saying, “Yeah baby, you feel that thick cock stretch you open?”
There is no comparison. Kyle had to be over six inches around, maybe closer to seven. It looked more like a big fat cucumber than a cock.
I finally gained the composure to speak.
“Uh, it’s no sweat, but you better keep that monster covered up. I feel sore jut looking at it.”
“Uh, Uh ok. Sorry,” he replied.
I walked by him heading for my suitcase.
“Do you jerk off a lot in girl’s rooms?”
“Ha, ha. I wish. I’ve never really messed around before.”
“Yeah, kinda sucks. I was just turned on by the whole… I just felt like I’ll never get a girlfriend cause I’m kinda… y’know, shy and not really built or anything.”
“Trust me. You measure up juuust fine. You’ll destroy a girl with that big thing.”
“Jake must be really big though. The way Kelly was acting and…y’know what she was saying. He’s big right?”
“Yeah, he’s the biggest I’ve been with but believe me you don’t have anything to worry about.”
“But, Kelly was acting like he was huge. I mean how does someone like me compete with that?”
Kyle was clearly frustrated, and me smiling like I had a big secret probably didn’t help. The virgin didn’t know I was horny beyond belief for him. Although, each time he mentioned Jake and Kelly my stomach dropped; I was still furious.
“Well did you see his dick or just hear Kelly?”
“No, I didn’t see anything…”
“Well unless he has grown three inches since last night you definitely have him beat.”
After dropping that bomb on him I pretended to switch my attention to shuffling through my bag nonchalantly.
Kyle was in hushed disbelief. It dawned on him that he had a monster cock between his thin legs. I was still pissed at Jake so I loved to talk down on him and make Kyle feel like the stud he really is.
“Yeah, it’s pretty sad huh?”
“Um… Can I ask you a question?”
“Yeah, sure. I think you can ask me anything, especially now, Kyle.”
“Does size really matter to girls? I mean do they actually care?”
“Well, it helps. Like I said, Jake has been the biggest and it feels really good compared to someone smaller. I don’t think most girls choose a guys because of his size but it’s like a bonus.”
I shrugged my shoulders with a laugh. I felt like such a size queen slut and I loved it. While digging for my clothes in my bag I made sure to give Kyle a show with my bent over booty wiggling back and forth teasingly.
“Haha, okaaay. So would I be bonus material.”
Kyle gestured down to his groin while giving a laugh. I set the clothes in my hands back down and walked over to Kyle. With my hands at my sides, I looked at him.
“Why don’t you let me inspect it and I’ll let you know for sure?”
What was I doing? I was never like this before, and I’m doing it for Kyle? Weird.
“Uh, um. Well… Ok, but will you like to show some too? Like maybe your underwear or something?”
He was such a hesitant man and it was cute. I stepped back and lifted my shirt over my head revealing my tight white push-up bra. I dropped my pants to the floor and stood there in my underwear with my hand on my hips chest arched toward him.
I slipped my hands into the waistband of my tight white panties and dropped them to the floor exposing my freshly shaved vagina. I stepped out of the underwear that rested at my feet and I reached behind my back, unclipping my tight bra I let it slip down my arms. I have slightly puffy nipples, a trait that I think Kyle took a liking to. I was now completely naked in front of this horse-dicked kid. Now maybe he would show it to me.
“Better?” I asked, thinking “how could this kid be so fucking big?”
“Uh, yeah,” he gulped. “Do you want me to…um take this off?” he asked gesturing to his towel.
“It’s only fair seeing as I’m completely naked,” I said. I noticed the thick bulge under his towel start to lengthen. As he stared at my tits.
“Uh ok,” he said. Then Kyle slowly uncovered his cock. He sat on the edge of the bed towel at his side. He was somewhat slouching back leaving his taut abs flexed. I couldn’t believe what I saw. Kyle had, by far the largest cock I had ever seen.
A mammoth plum-sized head the lay just below his nipple line. Thick foreskin cover 1/3 of the wide head. Just enough of his heavy foreskin pulled over the thick ridge of his unreal cockhead.
Below his head was a wide shaft every bit as thick as his immense head. The shaft had uniform thickness all the way to his groin with a slight upwards curve that is great for getting to hard to reach places.
At the base lay a heavy nut sack that I didn’t notice before. The sack flopped on the comforter and held to large nuts easily the size of golf balls. I thought for sure my mouth was wide open.
“That’s unreal,” I said. His giant cock pulsed at my comment. I watched as it stiffened at my gaze, straightening from semi limp to rock hard.
“Uh thanks.” he said nervously and confused.
I knelt down in front of it.
“Do you mind if I touch it?”
“Erm… No, not at all!”
I reached out my greedy hands. At first touch, I was surprised by the thickness of this kid’s cock. “How does he fit this in his pants?” I thought. As I lifted it from his abs I was surprised by the weight. I fastened each hand to get a better grip. I had one hand at the base and one just below the mammoth head.
“Wow, my hands can’t even reach around it! That’s crazy.”
“Haha, yeah I guess.”
“No seriously, look.”
I adjusted his cock in my hands.
“I know, mine didn’t either the last time I tried.”
“Wow,” is all I thought. I brought my right hand down to grip the shaft just below my left which was at the wide base of his massive shaft. Removing my left hand I placed it next to my right. Now with both hands mid-shaft, there was only a small amount of cock left between my hand and the beginning of his cockhead.
“Wow! Over three fistfuls, not bad at all Kyle!” I was trying to boost his confidence, but at the same time I was sincerely amazed at this huge thing.
I inched my hand up encircling my thumb and forefinger around the edge of his heavy foreskin. The rest of my fist tightened around the bottom of his huge head and the top of his thick shaft. I could feel the thick ridge of his flared cockhead pushing against the thick yet tight foreskin.
I started to slowly jerk his manhood. I tried to pull his fat foreskin back but it proved to be too tight. His cockhead flared and he let out a grunt.
“Are you ok?” I asked. I noticed my cheeks felt flushed and I was breathing heavy.
“Uh yeah, it just feels really good,” he said.
I continued with the slow jerking. After a few strokes, I couldn’t bear it anymore. Like a lever pulled his cock shaft down until the massive head sat in front of my mouth. I looked up into his eyes then closed mine and opened my mouth.
I pulled his giant cock toward my willing mouth. Opened wide I felt the tip of his meat entering. He winced once it hit my teeth. “This kid is BIG,” I thought as I pulled him out.
Gagging I said, “Well you’re too big for my mouth.”
“Uh, thanks for trying. Never done anything like this before,” he said.
I can’t believe myself. This kid is six years younger than I am. He’s still technically a man age-wise but he’s so innocent. His cock is just so frigging huge, “I’m just sooo curious….” I thought to myself.
“Yeah, sure,” I said.
I looked down at his cockhead he had begun oozing a thick white liquid. It started flowing out the wide slit and down his thick foreskin. Some trapped in-between his cockhead and foreskin the rest flowing down the length of his thick shaft.
“Are you cumming?” I asked surprised but impressed with the volume.
“Uh… Oh, no… that… Uh… happens when I get close, though. Sorry, should I…-”
Oh my… This kid just covered himself in more pre-cum than Jake could even dream of shooting.
“Well, seeing as you have your own natural lube… I think we should try to stuff that thing in something. You wanna try to, like, screw?” I asked not able to believe my own language.
“Yeah! I mean, ye-… yeah,” he said sheepishly. He was too adorable, and I felt hot being so desired by him and being in control compared to with Jake.
Feeling carnal, I pulled him down off the bed. His massive meat flopping hit him in his chest, then his thighs, as well as my forearms before resting at a downward hang.
I laid on my back head towards the door of the suite. I pulled Kyle on top of me his giant cock resting heavily on my own tight abs.
His weighty cock oozed onto my stomach pooling heavy precum in my navel. He lifted his massive shaft and directed it to my soaked and swollen vagina.
“Ok, please go slow. You’re really, really, thick so you’re gonna have a hard time getting it in just don’t force it or you’ll wreck me down there got it?”
He nodded and swallowed heavily. Inching forward he pushed the meaty head against my tightness. He prodded a few times before stopping.
“It won’t go,” he said disappointingly.
Breathing heavily I responded, “Just be patient I’m not exactly ready for one this big. Just, um, rub it up and down the slit, it’ll go.”
That’s exactly what he did. A few minutes of rubbing ended in the end of his fat cockhead penetrating my pussy. I couldn’t feel the ridge which meant that only two-third of that massive head had entered but it felt so big. He pushed in more. Each time Kyle met resistance he rubbed his cockhead up and down my soaked pussy. “He’s persistent,” I thought to myself.
Finally, he entered. I felt the thick foreskin followed by a side cock ridge push past my entrance.
“Two inches,” I thought as he pushed deeper.
I could feel his foreskin pull and retract inside of my vagina. It felt like a heavy deep pop which caused a stimulating vibration deep inside me.
“Four inches,” I continued to attempt to keep a count in my head. I could feel it rise more up my body, the fat girth already widening me so much more than my boyfriend does.
Kyle was now masterfully rotating the massive appendage inside of me and flexing it, causing me to go insane with pleasure. Before I knew it he sunk about 2 more thick inches deep inside me.
“Six inches,” I felt stretched like never before. It was a mixture of severe pain and unbelievable pleasure as he filled me. He worked those six inches in and out. Slowly due to the shear thickness that pulled on my pussy.
While Kyle was doing well plowing into my tight vagina I wanted to get more inside.
“How about you let me get on top for a bit?” I was gasping and covered in sweat.
I flipped on top of him clenching my thighs against him fearing I would lose his mammoth cock. I kept it deep inside me as we rolled together which cause severe pain inside but it was worth it. I now sat atop of his freakish manhood. I lost some of the progress I made and some of the freakish length fell out when switching positions.
With my face toward the door of our suite, I aced my hands on his chest and cocked my hips. Rocking back and forth I wiggled my little ass and tight pussy on his massive meat stick hoping that more would sink deep inside.
“FUCK, it’s so fat too. OOOH!”
Drawing more of his meaty cock inside of me I could feel Kyle completely stretching me. I got back to six inch mark… I reached down gripping his monster cock, the thing felt even thicker, if that was even possible. My fingers were even farther apart while holding the impressive girth. I continued to sink lower.
“Six and a half.”
This was about as deep as my boyfriend could ever go. Kyle’s fist-sized head felt like it was approaching my lungs. A girl with a mission, I dropped my hips down further.
I suddenly felt a great pain followed by a euphoric rush. Kyle’s bulbous cockhead pushed hard against what felt like a wall in the back of my pussy, where no one else has reached before. I looked down and saw there was about two inches left. I did some shallow thrusts, followed by rapid shaking while I started to climax.
“Now that I took your virginity, you’re hitting the virgin parts of me, stud boy!” I never talk like this, ever, but this massive thing brings it out of me.
I couldn’t move, I fell to Kyle’s thin chest, pressing my forearms into his upper body; I continued to shake with pleasure while his over-sized cocked pressed deep inside me. Once my orgasm subsided I began to rock my hips. Two to three inches of thick cock rocked in and out as I jerked my hips against his. I couldn’t believe how tight my soaked pussy was gripping his mammoth cock.
Before I knew I started to cum again. I just took his virginity and he made me cum twice and he hasn’t cum yet, and he doesn’t even look tired.
“I’ve never… I’ve never… felt like that before. That was sooo amazing. I’m dumping Jake later, but first I want more of this big thi-”
Speak of the devil, the door to the suite swung open and there was Jake with Kelly. I was still on top of Kyle with his large dick deep inside of me.
“Look what we have here. Un-fucking-believable. You couldn’t control yourself so you had to go fuck some teen twerp?”
Kelly looked frazzled as Jake started yelling at Kyle and I. I couldn’t help notice her hair was messy and her cheeks were bright pink.
“Couldn’t please a real man so you had to ride some kid, huh Em’?!” Jake mocked laughing.
With that, I put both my palms on Kyle’s chest and lifted my hips off of his. Slowly his massive cock snaked out of me. Seven inches, then six, five, four, three, then Kyle’s over-sized cockhead pushed my pussy lips further apart oozing precum as it did. It fell to his abs with an audible and heavy “thud” in the now silent room.
“Oh, my ga… he’s huge. He’s, he’s so much bigger than you!” Kelly shared with the room, not realizing what she’s saying in a state of disbelief.
Just over nine inches of the thickest cock I had ever seen was no laying on Kyle’s abs soaked with his precum and my juices. Not only that but I could feel myself gaping wide open, which I don’t think has happened with Jake ever.
“Uh, I think he’s got you edged out Jake by about four inches,” I teased.
“That’s gross! You’re, you’re a… fucking… fag kid.” Jake could barely complete a thought, he was dumbfounded by the horse-man hybrid in front of him. “Come on, let’s get the fuck outta here,” he said to Kelly but she stopped for a moment as if transfixed by Kyle too.
“Uh… uh, ok,” she said, and they left the suite.
It was no surprise that Jake acted like such a dick. He had always considered himself “huge” but the true was he was merely on the bigger side of average.
“Where were we?” I asked Kyle.
I rolled onto my back. Kyle positioned himself between my thighs, his thick cock waving ever so heavily just below his narrow waist. It was even larger than when it first went in me, and now it was slicked with my juices and his copious precum. He re-entered me just as thick as before. I felt him stretch my insides as inch after inch pushed deep inside.
“OOOooohmmm” I let out a deep moan as he pushed.
Kyle began thrusting. Nearly all but one inch of his massive cock was sliding in and out, pulling and pushing me. I started to cum, once, twice, and then quickly three times. Unbelievably Kyle continued to thrust.
I knew I’d be raw when we were finished, I didn’t know if my pussy would return to normal size. I would get sore after rough sex with Jake but this was different. Kyle, despite being gentle, had a horse cock and there was no mistaking that I would be hurting from the size of his monster.
“Ar-Are youuuu, g-gonnnna, cuummm?” I whimpered, I’m not even sure how I got the words out.
“Uh, yeah, yeah.” Kyle panted.
“Please cover me in your cum!” I was pleading. Shocked as the words left my mouth, but I just didn’t care. I was in complete lust over Kyle’s massive cock and cuckolding Jake.
“Are, are you su…-” I felt his body start to stiffen, “OHH!”
He began to thrust harder than before. As a result, plowing more of his monster inside of me.
“I’m gonna cum now.” He pulled out his massive cock, which seemed to take forever to drag out because of the length. As the wide head exited with a gentle “pop”.
Kyle encircled his hands nearly all the way around his sizable girth and began to pump. It was soon after that rope after rope shot out onto my neck, chest and abs. I was completely covered in his cum.
He released his grip on his immense member letting it hang heavily between his slender legs. It oozed the remaining semen. Dripping to the floor, it reminded me of Jake’s pathetic organism.
We held each other for a while. I felt his soft monster against my thigh as we lay on the floor of the suite.
Later that evening, I caught Kelly blushing as she stared at Kyle nearly the entire night. She had forgotten about Jake and so had I. Glancing at Kelly, I couldn’t imagine a girl her size taking a cock the size of Kyle’s but then again I didn’t think I could either.