2005 Story Archive

"Jim! Jenna is here." His mom called up to him.

Jim was fuming. He was fourteen! He didn't need anyone to baby sit him,he could take care of himself. He pretended not to hear his mother calling him. He heard her coming up the steps to his room. He quickly put on his Diskman, digging around in a box of junk he'd been given to sell at his swim team's flea market fund raiser, he placed his hand on one of those eight ball fortune telling balls. His mother appeared in the door way and motioned for him to follow her. He reluctantly got up and followed her down stairs.

Jim's eyes nearly popped out of his head. His sitter was a total babe. She was 5' 6", Strawberry blond hair that fell in an explosion of soft curls the cascaded nearly to her waist. Mark knew his mom was a C-cup this girl was far bigger than her, even stuffed as she was into her tight little top.

"Hi, Jim," Jenna said. "Glad to meet you."

Mrs. Chambers and Jenna spent a few minutes going over schedules and phone numbers before she left.

"I'll see you tomorrow evening, honey. Mind Jenna and don't get into any trouble. I know tomorrow's Saturday, but I want you to promise to stay at home all day."

Jim resignedly nodded. Baby-sat and grounded, it didn't get much worse.

Jenna was a college senior and had brought a lot of homework and study materials with her. She was open and friendly enough Jim decided, but she really didn't have much of an interest in a 14 year old.

"You can go and play if you want, Jim," she told him after supper.

"Play?" Jim thought. "I'd like to play with you."

The very thought of a woman this beautiful being interested in him,however ludicrous, turned him on immeasurably. His excitement grew, and before he realized it, he had a raging hard-on. Jenna, blushed and smirked as the front of Jim's sweat pants rose like a tentpole.

Blushing furiously, Jim backed out of the living room and went to his room. Lying on the bed, still very aroused, Jim picked up the eight-ball again and began tossing it the air and catching it in his hands.

Looking at the eight-ball, Jim decided to make a wish, just like he'd done a million times before. Wishes were okay -- they never happened -- but it was fun to pretend. Jim took the ball in both hands, shook it and solemnly said, "I wish Jenna found me attractive."

He flipped the ball over and in the dark window appeared a message ......

YOUR WISH IS GRANTED.

He hung out in his room for awhile, until he was sure his dick had gone down. Carrying the box and the eight-ball, he crept down the stairs and snuck past Jenna who had her books open on the couch studying. She hadn't noticed him. She looked even cuter with her glasses on, rubbing the tip of her cute button nose with the eraser of her pencil.

Shaking his head, Jim went to the kitchen and poured a drink of soda. As he was drinking, a voice behind him said, "What are you drinking there, Jim? It looks good."

Jim sprayed the contents of his mouth across the floor. "Uh, just soda. Do you want some?"

"I d like some water, but only if you'll pour it for me, Jim."

Stuttering Jim got a glass and poured Jenna a drink. She took the glass and drank it completely down. As she did, she ran her right hand across the side of her face and neck, then slowly slid the hand down her chest, side, and finally rested it on her rounded hip.

"That hit the spot. Would you pour me some more?"

When Jim shrugged, she asked him to come and talk to her awhile because she was tired of studying. Jim was elated, "Maybe the ball does work," he thought. Naw, that's impossible!"

Jim and Jenna went back together into the rec. room. Jenna put her glass of water on an end table. They spent the next hour together seated on the couch talking and watching TV. Jim couldn't help but notice that Jenna slowly but surely had worked her way across the couch until they were seated right up against each other. The smell or her perfume and the warmth of her body so close to him was driving him nuts. Then to Jim's immense surprise and delight, Jenna began to twirl his hair in her fingers as they sat there.

"I don't what it is Jim, but I really like you. You're a lot more interesting then most college guys I know."

She reached over to give him a friendly peck on the forehead, but when her lips pulled away, she had a strange look on her face. Jim didn't know much about women personally, but he had seen enough movies on the Playboy Channel when his parents weren't home to know what "that look" meant.

Jenna must have too, because she pulled back flushed and embarrassed.

"I just don't know what's come over me," she murmured, quickly sipping at her water. "There's just something about you Jim that I like a lot. Maybe you should be my boyfriend," she teased.

Now it was Jim's turn to go red. "I'm a little young for you ....."

"Well maybe I'm going to have to find the Fountain of Youth," she laughed.

"Or make a wish," Jim countered, remembering the eight-ball he'd used earlier. Handing it to Jenna, he said, "You could wish or something."

Jenna laughed, shook the ball, and wished for a long, tall drink from the Fountain of Youth. When she turned over the ball, a message appeared in the dark window ...... YOUR WISH IS GRANTED.

"Oh, boy," she said, laughing. Picking up her glass, she said, "Look out Jim, here I come." and drank about half the water in the glass with a gulp. Jim and she laughed together, Jim took the eight-ball back up to his room.

"Man, I wish wishes really worked," he thought, looking at the ball and tossing it back on his bed. Restless, he went down stairs to look at Jenna again. She was still sitting on the couch where he had left her , but she was staring off into space, her books and papers on her lap.

"Jenna?"

"Ooo! You startled me."

Jim thought that she looked different somehow, but he couldn't quite put his finger on it. She was certainly acting different -- she was more fun.

Her nose was no longer stuck in a book, and it was cute nose, too. She slowly started talking and then laughing with him. She asked him about school and she told him about her experiences. She started talking about her first cheerleading tryout and how she had broken a bra strap and her booby popped out in front of half the school!

He didn't hear the rest. She looked so pretty and perfect and, suddenly he realized what it was that was different. She looked younger.

"What? Do I have something in my teeth." she asked, breaking him out a stare he hadn't realized he was in.

"No. You look great!"

He stopped himself from saying "You look younger," but he left his mouth hanging open.

"I look what?" she purred seductively.

"Uh, great! You, you look great." He stammered trying to recover from the shock of his realization. "I'll be right back" He dashed up stairs to get the eight ball. Remembering what she had wished for and that it was happening. Jenna was getting younger. He almost thought it wouldn't be there when he rounded the corner into his room. He was relieved to see it sitting on his bed where he had left it.

"What are you doing up there?" He heard her call as she came up the stairs.

He quickly looked around for some place to hide the eight ball. As she approached he quickly opened his dresser but didn't have time to stuff it inside before she came into the room.

"So this is your room. Cute." She said with a big smile and started playfully looking around.

Jim watched her closely and he could see that she was looking even younger than she did downstairs. She didn't look like a college senior anymore -- more like a high school senior -- Jenna looked like she was eighteen. Her body was also starting to change, her jeans looked looser around her waist. She sauntered over to his bed and sat down. His heart was starting to pound with excitement and fear. He hadn't really thought about what he would do, even if she was young enough to like him, she didn't really know him and he didn't know her.

"What kind of music do you like?" she asked.

"All kinds really. Rock mostly, some Rap."

"Why don't you put some on?"

"Sure!" He said as he went to his CD rack. He would glance at her over his CD as he looked through them. He wasn't paying much attention to the CD's. He could see she was still getting younger. She looked all of seventeen now! Her face look cute and more innocent. His hands picked out a CD, he didn't even see which one. It was a slow romantic one.

She looked up at him and smiled knowingly as the music started. His face flushed with embarrassment and he turned to stop it. Her hand on his shoulder stopped him in his tracks he turned around to stand face to face with her.

"Dance? Why I'd love too." She cooed and slid her arms around him and pressed her body into his. The smell of her sweet perfume filled his nose and the warmth and softness of her breasts intoxicated him This was beyond his wildest dreams. Here he was with this gorgeous, sexy girl throwing herself at him. They slow danced for a while, their hands cautiously exploring each other. He ran his hands down her side and onto her nicely rounded butt. The song ended but she stayed close to him.

Even he knew what that meant. He kissed her long and deeply, finally they broke and he noticed that she suddenly felt slimmer in his arms and her breasts didn't press so much against his chest. He looked at her face and it looked softer and rounder. Her nose looked smaller and more upturned.

"That was nice. You're a good kisser." she said.

This is too weird. He thought as he looked at the sixteen year old beauty in his arms. She shifted a bit and noticed something strange herself.

"Wow! What's happened to my clothes?" She gasped as she tugged on her jeans. "How did they stretch so much?"

Her voice also sounded a more girlish tone now. She tried to get them to stay on her slimmer hips, but they were too large.

"You have a unique way of getting a girl out of her pants." She said teasingly as the slipped them off.

"I know you just want to get a look at my legs." She posed her legs for him and they were quite nice. He noted that her tits were also smaller now. Her top looked the right size now and as far as her was concerned she was the perfect age for him now.

"OK, it's your turn. Let's see your legs." She giggled and helped him take off his pants. "Nice and strong, sexy too." She purred. His heart was pounding so hard he thought it would explode. She was half clothed and was trying to get him undressed too. She took control and pulled his pants off and flung them to the other side of the room, and started on his shirt and it was soon gone.

She looked at herself in the mirror, and stopped. Her hands went to her face and then ran down her sides and flanks.

"Looks like I got my wish, doesn't it Jim?" she said in a voice made even more sexy to him by its higher, girlish pitch. She crossed to Jim's closet, opened it and took one of his button shirts.

"Turnaround, young man," she said in a mockingly stern voice. Jim obeyed and was bombarded with her oversized blouse, panties and bra. Turning, he faced the most beautiful fifteen year old he'd ever seen. Jenna's blond hair draped across the shoulders of Jim's shirt, which was now too big for her. Jenna came to Jim, and he noticed that now Jenna was shorter than he was -- no more than five-three."

"I guess I'm not too old for you now, am I Jim?" she asked, pressing her lips to his. Taking his hand in hers, she pulled him over toward the bed. "Make love to me ...."

Together they pulled down the covers of the bed and as Jim moved to get in, she stopped him. As he stood facing her, Jenna starting kissing Jim's face, neck and shoulders. Then, she bent forward and kissed his chest, pausing long enough to take his nipples between her teeth and run her tongue across them. Jim was moaning, this was beyond his most wildest fantasies.

Jenna was kneeling in front of Jim. her hands ran up and down his sides, then suddenly, her hands darted across his backside and then his groin. Jim gasped, as Jenna massaged his cock through his underwear. Without warning, she reached either side of his briefs and slide them down to his ankles. His cock stood out stiffly from his body, and before he could even react, Jenna slipped her mouth over the tip of his dick and then took it fully inside of her mouth.

In and out, in and out, Jenna worked Jim's cock like a piston. Jim felt the pressure building within his balls, he groaned and took her hear in both his hands as she continued to suck him. Before he even realized it, he erupted with a load of his young semen within her mouth. Without missing a beat, Jenna continued to suck and swallow, finally stopping and looking up at him. Jim learned at that moment that a girl could suck and smile at the same time.

Jenna stood and whispered, "You taste as good as you look. But I hope you've saved some because we re not leaving here until I've had your cock in my pussy."

Jim looked at her and realized that Jenna was still getting younger. She now looked his age -- fourteen. Her young shapely limbs were getting lost in Jim's now too large shirt. Jenna noticed, too. Stopping before the full length mirror on Jim's closet door, she looked at herself, brushed her hair back with her hands and giggled.

Looking at Jim in the reflection, Jenna said, "Experience is a great thing, the only problem is you have to be older to have a lot of it. When you get older, Jim, you'll hear people say 'I wish I knew what I know now when I was a kid.' Now thanks to you, Jim, I will."

She raised her hands to the buttons of the shirt and unfastened them. Then turning she let the shirt drop from her shoulder. Fully naked, her breasts -- no longer as big as they were when she was older, hung straight, proud and pert from her chest. Her features, more childlike than before, still looked sexy as she gazed at him with the eyes of a 23-year-old woman.

The hair of her pubes was light, sparse and downy. She ran her hand across the lips of her vagina and moaned, "All for you Jim."

She joined him in the bed. "Have you ever made love to a woman, Jim?"

"No."

"Then let me show you how ......"

Placing Jim on his back, Jenna straddled him and slowly began kissing him up and down his body. Slowly, but expertly, she moved her moist slit up and down the shaft of his penis. Jim fondled her breasts and then reached up and kissed them, greedily sucking her small nipples. Jenna began to moan with passion, then reaching between her legs, she guided Jim cock to the entrance or her pussy.

"In here Jim, that's where I want you."

With a thrust, he plugged her pussy with his cock, thrusting deeply and hungrily into her. Without realizing it, he pulled her to her side and then on her back and mounted her as if he'd done it a thousand times.

"Oh, Jim, Jim, yes, yes, deeper, harder, Jim, I want you, give it to me, give it to me, oh Jim, oh, Jim, yes, yes."

Jointly moaning, the two young lover climaxed together, Jim shooting even more hot juices into Jenna than he had when she sucked his cock. Jenna writhed and rocked back and forth screaming with a woman's lust, and a young girl's voice.

Jim and Jenna laid -- still locked together -- until his flaccid penis slipped out of her. He cupped her face in his hand. "You've gotten younger," he said.

"Really? I've always liked older men. Who knows Jim, if this keeps up, you'll be baby sitting me in a few hours," she giggled.

Jim rose to go to the bathroom, and yelped when he noticed his cock and thighs were coated with a thin sheen of blood.

"I'm bleeding," he yelled.

Jenna lifted up the sheets and stared at her crotch. "I'll be," she said. "I not only got younger, I got cherry again!"

"What?" Jim asked.

"Cherry. Cherry. It made me a virgin again. You busted my hymen, Jim. As far as my body was concerned, it was my first time, too. I don't know any other girl that can claim that!"

Jenna started wiggling in the bed. "What's the matter?" Jim asked.

"Gotta pee. This body is smaller than I was before, and all that water's got to go somewhere."

She stood, and giggled again, "Ooo, I'm leaking."

Jim cocked his head to one side.

"I'm full of little Jimmy wrigglers, and some of them are falling out!" she said as she padded to the bathroom. She turned on the shower and called Jim to join her. They soaped each other and kissed and then dried each other off. As she combed out her blond tresses, Jenna observed that she had regressed to about thirteen, but didn't seem to be getting any smaller or younger. She stood at just five feet tall, and weighed no more than 95 pounds.

The two then went back to Jim's room, stripped the bed, remade it and climbed in together. Slowly, but finally, they fell asleep, nestled together like two spoons, Jim with his hand cupped around Jenna's now much diminished breast.

Continued in Part 2

Back to Babysitter - part 1 by Chronos