Kyle's First Time

JealousBOy

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"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" 100lbs 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 really hard. It stuck out with a slight downward curve. I took hold of it.

"Yeah babe. Seven inches all for you." he moaned.

I remember thinking, "Wow. Seven inches?"*

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 longterm boyfriend and girlfriend. We moved in together while I started grad school.*

During this time I had kept in really god shape. Jake on the other hand just kept hanging out with his college buddies. They went drinking almost every other night. He lost his tight abs. While he didn't have a beer gut I have to say nothing was hotter then a pair of ripped abs.

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'.

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.*

"Baby you feel so big." I moaned 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?" he grunted.

"Yeah you're so deep." it felt so good to have him so far inside me.*

"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.*
 
I am guessing 18 year old Kyle and Matt are going to be in that wedding party !!! Sounds like another great story is on its way . . .
 
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 cousins others were just friends of the bride and groom. This afternoon would be mostly 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.

Across the hall Jake shared a suit with the younger cousin of the groom his name was Kyle. Kyle had just had an 18 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." she asked plainly.*

"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.

"Hi 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 demanded.

"I'm going swimming. Isn't that obvious?" he said.

"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.*

"Go for it." he said and walked away.
 
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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 decided that Jake was just under a lot of pressure and that him handing out with a teenager at the pool didn't mean a thing. I walked down to the pool to set and watch. Just as I round the corner I saw Jake and Kelly in the pool. He had his groin pushed tightly against her tight bikini bottom smirking as he grinder 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." she continued.

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? What..." and that's when I heard the moaning.*

"Are they. Are they screwing in there?" I demanded.

"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 so deep, it's so deep. You're really big. Oh shit." she moaned as she bounced.

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 their. I was shocked.

Kyle, skinny shaggy haired Kyle was I. The edge of my bed sitting on his towel using both of his hands to beat off the biggest cock I had ever seen. Just as I entered the suite my mouth hung open.

"Shit." he released his humongous cock fro. Both hands and it hit his tight abs with a heavy audible thud. The giant head oozing precum as it rested just below his nipple line. He quickly pulled the towel over his groin trying to cover his massiveness.*

"I'm really, really sorry. It's just...well I thought...you were gonna be a little longer. I'm sorry." he stuttered.

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 cockedhead.

"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.*

How could this kid be so fucking big? I thought.*
 
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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 two inches wide. It looked more like a big 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." I laughed.

"Uh, Uh ok. Sorry." he replied.*

I walked by him heading for my suitcase.*

"To you jerk off a lot in girl's rooms?" I asked jokingly.

"Ha, ha. I wish. I've never really messed around before." he said.

"Oh."*

"Yeah. Kinda sucks. I was just turned on by the whole...(he nodded to the suite across the hall) I just felt like I'll never get a girlfriend cause I'm kinda shy and not really built or anything."

"Trust me. You measure up just fine. You'll destroy a girl with that thing." I laughed.*

"Jake must be really big though. The way Kelly was acting and...what she was saying. He's big right?"

"Yeah. He's the biggest I've been with (yet) but believe me you don't have any thing to worry about." I smiled.

"But Kelly was acting like he was huge. I mean how does someone like me compete with that?" he seemed frustrated.

My stomach felt a pang of jealous each time he mentioned Jake and Kelly.

"Well did you see his dick?" I asked.

"No."*

"Well unless he has grown two inches since last night you definitely have him beat." I said as I shuffled through my bag.

"Two inches?" he said in a surprised whisper.
 
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“Yeah, pretty sad huh?” I responded as I fumbled with some of my clothes in my suitcase.
“Um, can I ask you a question?” he asked.
“Yeah sure.” I said turning to look at him.
“Does size really matter to girls? I mean do they care?” he asked sincerely.
“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.
“Ha, ha. OK. So would I be bonus material.” He 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?” I said with a giggle. What was I doing?
“Uh, um. Well…ok but will you like show some too? Like maybe your underwear or something.” He asked hesitantly.
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 in 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.