Jack and Jenny

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Tail Plug

Jack was home for the summer, so his father made sure he would be working and not laying up on the couch. Jack always came home from college over the summer, so he could hang out with his friends and make some cash for the fall. His parents were going on a cruise for the next week and a half. So his father had him extra busy.

It had been a while since he had been home. After his work was done, he got in his truck and drove around to what had changed. It was a small town, so not that much was different. He saw some friends and had a few beers. After a few hours he decided to go home. On his way back, he was driving through his neighborhood and who did he see walking down the street? Jenny. Jenny was the girl who had lived in the house next to his for almost ten years. He had often fantasized about her, but because she was so young he knew nothing could ever happen. Although, she was looking good this afternoon.

Jenny was wearing a short, cut off tank top and some tight shorts. Jack could see those 18 year old cheeks just calling his name through those shorts. Jack, being the good ole southern boy that he was, decided to stop and say hello.

“Hey jenny.”

“Hey jack. When did you get home?”

“I’ve been back for about two days. Hey, do you need a ride?”

“Yeah, sure. Thanks.”

It was only a short ride to their houses. Jack pulled up right in front of Jenny’s house.

“Well thanks for the ride.”

“Sure. No problem.”

“Hey, what are you doing later?”

“Oh, nothing. My parents are out of town, and my dad left a list of chores as long as you are. I probably just chill out at the house, have a few beers and get up early tomorrow.” Jack had thought of Jenny as too young for so long, that he had forgotten just how old she was now.

“Well, that sounds terrible. How about I come by later and cheer you up? We can watch a movie or something.” Jenny, never being as honest and good as jack believed her to be knew exactly what she was doing. She had always wanted jack, the 24 year old stud. And now she was going to have him.

“Alright, I could use the company.”

“Great! Well, it’s already 6:00 now; I’ll be over in an hour.” And with that she jumped out of the truck before jack could say another word. However, she forgot to conceal her grin that was as wide as her pretty little face. This grin would puzzle jack for the whole hour.

“I wonder what she has in mind. She couldn’t want sex. She’s too young, too good, I know that can’t be what she wants.” Jack then began to think about the grin. “Maybe she does want me. I’m always hearing something about poker oyna how teenage girls are attracted to older men. But, me?” Jack, even though very confused, couldn’t help but notice that he was getting hard thinking about Jenny’s little plump ass, her perky breasts, and that voice! Her voice was one of those that made her sound about five years younger. Jack couldn’t stop hearing that high-pitched voice moaning in his ears.

Jack sat down on the couch, opened a beer, and thought over and over again about Jenny’s little grin. Then, he heard the doorbell ring.

He opened the door and saw her.

“Hi.” She said. She nearly knocked Jack and his raging hard-on back when he opened the door. She was wearing short, black, miniskirt that barely covered her ass. She had on some kind of red shirt that made her breasts look divine.

“Hi,” was that jack could muster up to say. Well there was no debating her intentions now. There was no way in hell she came over to just watch a movie dressed like that.

“Well, aren’t you going to tell me to come in?” she said with a devilish grin.

“Yeah, sure, come on in. Make yourself at home.” Jack said as he watched her ass as she walked in.

Jenny came in and immediately sat down on the couch.

“Can I get you anything to drink? Water, juice, soda?”

“I think I’ll have a beer.”

“No problem,” jack said. He got two beers and had a seat on the couch next to Jenny.

“Thanks, Jack. You know you’ve always been so nice to me.”

Jack just sat back and played along. He thought, “Well, if she’s come this far I wonder how far she wants to go?”

“Me? No, I’ve just done what I could.”

“Jack, stop it. You know you have always been nice to me. You never let anyone pick on me, you helped me with my homework a million times, and you always gave me a ride when you saw me walking.”

“Well, I just wanted to be nice. I figured you would’ve done the same for me.”

“I’m gonna do better than that. Jack you know I’ve always had a crush on you, right?”

“Really? I guess I just…”

She cut him off. “Listen, I want you hear and now. I want you to be my first.”

“Jenny, I’d love to, but….wait, you’re a virgin?”

“Not really. I had a guy once, but he was a virgin too and didn’t know what he was doing. That’s why I want you.”

Jack was so taken back that he couldn’t speak.


Jack couldn’t fight it anymore. That little voice of hers had flipped his switch and now he was going to fuck her like only a MAN could.

“Okay, I want you to go to my bedroom.”

“Yes canlı poker oyna sir.”

He watched her little plump ass walk through his living room, down the hall, and then lay right down into his bed. He told her to lean back and spread her legs. She did. Jack got down on her knees and began to lick and kiss her thighs. She moaned with desire.

“oh I like that.”

Jack then worked his way up to her pussy, and began to lick her from her asshole to her clit.

“Oh yes jack! Oh my god that feels so good!” she cried out.

Jack ate her until her little pussy was gushing. Then, he applied his fingers. He played with her asshole with one, and inserted the other into her tight teenage pussy.

“Oh my god jack, I had no idea! I had no idea it felt this good! Oh my god, I think, I think, I think I’m gonna CUM!!!” she screamed as she climaxed.”

Jack paused then rose to his feet. Jenny lay there stunned by her first orgasm.

“Oh god jack, that was unbelievable!”

“Were not done yet sweetheart. Take off your clothes.”

Jenny, noticing the bulge in Jack’s pants, immediately threw her clothes to the floor. “I’m ready, Jack.”

“Now I want you to suck my cock.”

“Yes sir!” Jenny said with joy.

Jack had thought he would have to teach Jenny about this too, although he soon noticed she had a very good idea of what she was doing. Jenny sucked the head of his cock, and massaged his balls.

“Oh yeah, Jenny. Just like that.”

Jack then pushed her head down, and he could feel her swallow all of his pride, and yet she didn’t choke or cough once. She simply took what he gave her, all of it.

“Alright, now I’m gonna fuck you.”

“Yes, sir. Just tell me how you want it.”

“Get on your back and spread your legs.”

Jack now took the head of his cock and pressed it right up against her pussy. He looked her straight in the eye, as he pressed himself inside. Her pussy was very tight and very wet. He felt the walls of her pussy stretch and squeeze his cock the further he went in.

“Oh my god jack you’re so big! Oooohhhhh, yes! Yes! Yes! It feels so good jack. Fuck me jack, fuck me!”

Jack began to slide in and out, in and out. He felt her sweet, wet, pussy squeezing his cock the whole time.

“My god you’re tight!”

“I…Lied…all…I’ve ever…done…suck…cock,” was all she could say in-between Jack’s thrusts. “I am a…virgin, I…wanted…you to be my first,” She finally sputtered out as jack took himself out for a moment.

“Well, then I’m a lucky man, baby. Get on your hands and knees for me…I’m gonna fuck you from behind.”

“Oh internet casino yes jack…,” she said as he slid his big cock down her asscrack, over her ass hole and into her pussy.

Jack began to fuck her from behind, as she wailed loudly in ecstasy. He began to spank her ass in time with her thrusts. At this time, Jenny could barely do anything but moan and cum. Since he began fucking her she had already come four times. Jack then began to fuck her in as many positions as he could; sideways, her riding him, missionary, and many more. Jenny could do nothing but cum and moan more than she had ever before.

After having a go at her riding him, Jenny’s little teenage pussy was tired, and dripping with cum. “jack, before you cum…,” she said in between a position change, “I want to fuck my ass.” Jack’s mouth dropped open.

“Are you sure you’re ready? It can hurt a little at first,” jack warned.

“I’m ready Jack; I put my vibrator up there all the time. Besides, I want you to have me first…in every way.” She said and smiled looking back at him as she pushed her ass into his crotch.

Jack was up for the challenge. He fucked her pussy for a minute to lube up his cock and then prepared to do the deed.

“Mmmmm…,” she said as he began to finger her asshole and get it lubed. “Oh yeah, oh yeah,” she said as he eased himself in. Jack had had some anal before, but Jenny was different. She was a teenager, and her ass was virgin.

He pushed himself deeper and deeper, as Jenny moaned. Then he began to fuck, pulling himself almost all the out, then plunging himself as deep as he could. Jack had expected to see Jenny wince with pain (he did have a huge cock), but she just moaned with joy and wore a smile the whole time.

“Ooohhh jaaacckk…yes…I …like it…so…muuucchh,” was all jenny was able to cry out.

Jack had his way with jenny’s ass for a good while, and then he knew it was time. Jack told her, “Jenny, push up against me, I’m…gonna…CUM!!” Jack said as his cock erupted with cum all inside jenny’s ass.

“Oh yes baby, cum in my ass…” Jenny said with all the energy she had left.

Jack soon fell to her side.

“My god! You are a sexy little fucking machine aren’t you?”

“Well…I…try,” she said while still trying to slow her breathing.

They laid there for a while, just trying to recuperate themselves enough to get to the bathroom.

In the bathroom, Jack took a five minute piss, and Jenny tried to get all the cum that was oozing from her ass.

“Oh baby, were gonna half to do this another time,” said jenny while she tried to walk to the bed.”

“Any time you’re ready,” jack said right behind her.

Jenny putting her clothes on, “well how about tomorrow? My parents won’t be back until Monday and yours for another week and a half.”

The end?

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