Jack to Jackie

[Sissy Baby Rachael]

Once upon a time there was a little man named Jack. Jack was rather small at just five-foot-two, was not very strong, and has a very boyish face, which he hid under his long greasy hair and beard. He was a trouble maker who had a rap sheet longer than himself. Nothing too serious, of course. A lot of burglaries and pick pocketing, some drugs, and a little alcohol.

Jack was walking down the street one day (slightly tipsy) when he was suddenly jerked in to a dark alley by two tall, muscular men. They lifted him up off his feet and pinned him up against the brick wall.

“You owe us a lot of money Jack,” the one on the left growled.

“I-I-know R-r-alph,” Jack squeaked, “you’ll get it. When have I ever cheated y….”

The other man, Rich, wrapped a hand around Jack’s throat and squeezed a little. Jack squeaked and began to thrash about.

“You’ve got twenty-four hours to pay up before we come find you, and next time we won’t be so nice.”

They let go and Jack fell to the ground, landing on his side and letting out a moan. The two men stepped over him and walked away, leaving Jack quivering on the ground.

Jack suddenly realized that he was wetting himself. He was so scared. He began crying out of embarrassment. Not wanting to be seen like this, Jack began running to the outskirts of the town and in to the woods. He must have run for hours before he became tired and fell to the ground. He was cold and tired and hungry.

He noticed a small light in the distance. He realized that it was a rather large two-story wooden house, with a garden in the front yard. He had just found his next meal.

He ran to edge of the garden, fell to his knees, and began pulling carrots out of the ground and eating them with the dirt on them. He was on his third one when he felt a presence behind him. He slowly turned around and looked up.

There stood a giant woman. She looked to Jack to be nearly seven feet tall. She was plump, pear-shaped, with an ample bosom. She had a round face and short blonde hair.
Jack panicked and attempted to crawl backwards, slipping and hitting his elbow.

“Why you poor little thing,” she said in a warm voice, “who would abandon such a sweet little baby?”

She reached down and lifted him up as if he weighed nothing at all. It was as if he was simple a doll. She cradled him in her arms.

“I’m not a b-baby!” I yelled frantically squirming and trying to get away.

She giggled.

“Not a baby? But you must be. An adult certainly would know better than to steal from someone’s garden. And besides, adults don’t do that,” she said pointing at Jack’s wet pants.
“I must at least for the moment believe that you are in fact a baby and the answer to my prayers.”

Before Jack could say another word, she turned and carried him in to the house. Everything seemed to be a blur to Jack until they arrived in the bathroom. She set him on the floor and turned on the water. She filled the tub with water.

She stood up and opened a cabinet. She took out a large white tube. She turned back to Jack and knelt down. She began undressing him.

Jack squirmed and tried to get away. She gave him a pop on the behind.

“Stop it,” she said. “This is for your own good.”

Suddenly, he was naked. He turned bright red. The woman giggled.

She squeezed some cream out of the tube and began spreading it over Jack’s upper lip and jaw. Next, she spread it over his chest and back. Then she started at his feet and worked her way up his legs. He was starting to get excited as she reached his groin. She worked there long enough to get Jack excited and stopped. Jack let out a moan.

The woman giggled. She sat there just looking at Jack, as if she were waiting for something. Suddenly Jack realized what it was. His skin began to tingle at first and then start to itch slightly. He went to scratch himself and before he could the woman scooped him up and lowered him in to the tub.

Jack’s head went under the water and he popped back up. Looking down he saw that most of his body hair was gone. He tried to stand up, but the woman easily held him in with one hand and began to scrub him with a wash mitten with the other, wiping away more and more hair with each stroke. She took her sweet time, exploring every little nook and cranny. Once again she got Jack excited, but let him have no relief.

Jack was starting to cry in frustration as the woman forced him to lean back and began putting shampoo in his hair. The sweet smell of lavender reached Jack’s nostrils. Despite the complete humiliation of what he had just been through, everything that had happened that day had left Jack exhausted. He simply lay there whimpering as this complete stranger gingerly massaged his scalp and cleaned his hair.

After what seemed like an eternity, he felt himself being gently hoisted out of the water. The woman gingerly dried him off with a towel and then picked him up naked. She began carrying him to another room in the house.

Jack opened his eyes and his mouth dropped open.

They were standing in a giant pink nursery! There was an enormous pink crib with a locking top and restraints. There was a large changing table that also had restraints. The changing station had three shelves loaded with stacks of disposable diapers, cloth diapers, plastic pants, rubber pants, baby oil, baby powder, and Vaseline. There was a large pink playpen with a locking top.

Jack knew what was going to happen, but he could not escape. He was carried over to the changing table and placed upon it. He tried to sit up, but the woman held him down with one hand.

“P-p-please!” Jack squealed beginning to cry again. “I know eating from your garden was wrong. I am sorry! But don’t put a diaper on me! I’m not a damn baby!”

“That remains to be seen. I happen to think you are, but I will give you the chance to prove me wrong.”

Jack held his breath.

“I am going to assume you are a baby and put you in a diaper for now. And I am going to feed you a bottle, since I know you must be hungry. I will put you to bed and if your diaper is still dry when I come to wake you at eight in the morning, then I’ll know that you are an adult. This means you did know that eating from my garden was wrong and I will give you one hundred swats on the bare behind with my paddle. Then I will give you your clothes back and let you go. If your diaper is wet, then I will know that you did not know better because you are a baby. You will still get ten swats for lying about being an adult. But you can keep your diaper on.”

Jack found himself shivering. One hundred swats!

“And if you are a baby,” she said, “then I will have no choice but to keep you here and care for you as your Mommy for the rest of your life.”

Jack began crying.

The woman rolled him on to his back and put his wrists in restraints, binding him to the table. Jack heard her open a bottle and then felt something warm being gently poured down his back. Baby oil! The woman took her time caressing and rubbing the oil in to his neck, shoulders, back, bum, legs, and feet. Her touch was so soft and the oil so warm that Jack couldn’t help but relax.

She undid the restrains, gently rolled Jack on to his back, put him back in restraints and repeated the process on his front side. She started at his neck and worked her way down to his waist. Once again Jack became excited. The woman noticed and grinned.

She moved to his feet and slowly worked her way up his legs, getting Jack even more excited. She finally cupped his balls in warm oil in her left hand and slowly slid her right hand up and down his member. The whole time she looked deep in to his eyes.

Jack cried at the fact that he was being pleasured in this way, until finally he felt the orgasm approaching. He closed his eyes and waited, but the woman suddenly stopped. Jack felt a cold baby wipe being wrapped around his member and rubbed up and down furiously, bringing him out of his trance.

“No!” he yelled. “Please, I want…” but the woman slipped a pink pacifier in his mouth and secured it behind his head.

“Just relax little one, Mommy will be done soon enough,” she cooed.

Jack experienced a sudden pain in his groin. Blue balls. He let out a moan around the pacifier as Mommy rolled him on to his stomach again. Jack felt the cool touch of baby powder. Mommy gently sprinkled a generous amount all over his back side and then rolled him over and began sprinkling it on his front. Jack inhaled a little bit and it caused him to sneeze.

“Bless you, little girl,” Mommy said.

Jack gave her a curious look. Little girl?

Mommy took a picture out of her pocket and held it up for Jack to see. It was her and a man who was even taller than she was, about a foot taller in fact. He had dark black hair, sharp features, and rosy cheeks. He was wearing a dark black suit and laughing heartily. And there was Mommy in her wedding dress, with her arms wrapped around him, smiling up at him.

“My husband and I always wanted a baby girl. We tried for years to get pregnant but we had no luck. He died a few years ago. Shortly after that, I discovered the world of adult babies. I found out that there were adults who wanted nothing more than to be treated like babies by men and women willing to be their parents. I knew I was too old to get pregnant so I prayed and prayed and prayed that an adult baby would find me, and it looks like she may have.”

Jack felt a pit in his stomach as Mommy grabbed his ankles and lifted his bum off the table. She slid a large disposable diaper underneath him and set him down. She pulled the diaper up slowly, letting Jack feel every inch of it touch his skin. Finally fastened the double tapes on each side securely. She patted the front of his diaper.

“There we go!” she said. “Now just to be sure that we don’t have any leaks,” she said, reaching up and taking two cloth diapers down. She folded them quickly and fastened them on over the disposable diaper with two locking diaper pins on each side. Last but not least she slipped some plastic panties over the diapers. Jack found that he could not bring his legs together.

Finally she undid the straps. Jack tried to roll over but she picked him up.

“Oh no, sweetie,” she said. “Mommy’s not done yet, she still has to get baby dressed for beddy-bie.”

She carried Jack over to the dresser and open one of the bottom drawers. She pulled out a large pink sleeper and some pink mittens. She slipped the pink mittens over Jacks fists, rendering his hands useless. Then she slipped his arms and legs in to the sleeper. He could feel her zipping up the back and realized he was stuck in this until she let him out. The sleeper was soft and snug and didn’t allow for much wiggle room.

Finally, the woman lay a large pink baby blanket out on the floor. She laid Jack down with his arms at his side and wrapped it around him tightly. He was completely in her control.

She picked him up and walked over and placed him in the crib.

“Mommy will be right back sweetie.”

She left the room. Jack knew trying to escape was futile but he couldn’t help but try. It was no use. Every bit of effort he made to move wore him out. He was getting hotter, sweatier, and more exhausted by the minute.

Finally, Mommy returned with a large bottle of milk.

“This should fill up Baby’s tummy nicely,” she cooed.
She picked Jack back up and walked over to the rocking chair. She sat down and took the pacifier out of his mouth and quickly slipped the nipple of the bottle in to his mouth.

Jack lay there refusing to drink.

She’s not going to do this to me, he thought, I won’t let her.

That wasn’t what Mommy had in mind. She gave the bottle a squeeze quickly filling Jacks’ mouth with milk and gently pinched his nose. He couldn’t breathe! He quickly swallowed and Mommy let go of his nose. He shivered and realized that he had no choice. He slowly drank while Mommy rocked and hummed.

Soon he felt the need to pee. It wasn’t urgent yet, but there was still a lot of milk left to go.

Finally after an eternity, the milk was gone and the nipple was slipped out of his mouth. Mommy put him over her shoulder and began to pat his back. Jack felt an enormous bubble bouncing up and down in his stomach. Finally, Jack felt it move up in to his throat and he let out a big belch.

Mommy slipped the pacifier back in his mouth and secured the strap again. Then she carried him over to the crib and placed him in the middle. She threw two large blankets over her already bundled up prisoner and tucked them tightly under the mattress. She raised the side of the crib, slid the top closed and locked it.

She then pulled the rocking chair close to the crib and sat down. She watched Jack try to helplessly squirm.

“Did Baby like her din-din?” Mommy asked.

Jack just closed his eyes in shame and tried to ignore his bladder.

“Oh, I guess my little girl is trying to hold in her fluids. Well, if she does she’ll prove that she’s a grown up and will be free to go. Of course she’ll be leaving with a very very sore bottom.”

Jack tried to ignore her.

The woman said: “Mommy is going to tell her baby a bedtime story and then put on a little music that helps Mommy fall asleep.”

This can’t be good, Jack thought.

“Once upon a time there was a little cloud named Clarrie. Clarrie lived in the sky above a tiny village. He loved flying very very much. He wanted nothing more than to fly far far away, out over the ocean like the bigger clouds. One day he did. He spent all day soaring over the ocean, picking up lots of water. This water made Clarrie very full and turned him in to a dark storm cloud. By the time he got home, he was sure he was going to burst. He just HAD to let the water out. But he knew that he couldn’t because it would get the people in the village wet. But finally, Clarrie couldn’t hold it any longer. The water came rushing out of him and hit the ground and Clarrie felt much better. And you know what else? The villagers weren’t mad. They were happy because Clarrie’s water helped their crops grow. The End.”

She blew Jack a kiss and walked over to the changing table. She pressed play on the tape player and walked out of the nursery, closing the door and leaving Jack in pitch black. Suddenly from the speakers came the sound of dripping water. It started off as a trickle and slowly built up to a heavy rain fall. Jack did his best to ignore it and finally passed out and fell asleep.

Jack awoke some time later for two reasons. One, there was light shining in his eyes. Two, his need to pee was unbearable. He couldn’t cross his legs or shift around or do anything to relive the pressure. What time was it? Surely it was at least eight by now and Mommy would be coming to check on him soon. He held off as long as he could until finally he couldn’t take it anymore.

Just as his bladder gave way, the door opened and Mommy came in! Why couldn’t she have come a few seconds earlier? Jack noticed the large wooden paddle in her hand and felt the wave of urine spread though his disposable diaper and leak in to the cloth diapers. He tried to yell, but the pacifier muzzled him.

“Well,” Mommy said, “it’s time for me to see what I’ve got.”

She walked over to the crib and set the paddle down. She lowered the side. She untucked the blankets from the mattress. The unwrapped Jack and unzipped his sleeper, and pressed against his plastic panties checking the diapers for wetness. They were soaked of course. She looked at the tears in his eyes and Jack thought he saw a sympathetic look. She picked him up and began patting his bum and rubbing his back.

“There, there,” she cooed, “it’s OK Jackie. Mommy’s not mad at you for wetting your diapers. That’s what babies do. Don’t cry honey. You’ve made Mommy so happy.”

Jack wailed at his new name but the pacifier muffled all the sound.

Mommy pulled Jack back and looked down at him.

“Now Jackie, Mommy still has to give you ten spanks for eating out of her garden yesterday. But like I promised, you’ll get to keep your diapers on.”

She picked Jack and the paddle up and walked over to the rocking chair. She sat down and put Jack over her knee. He was shivering in fear. He felt her placed the paddle on the diaper and then heard the whoosh! as it came up in to the air and another whoosh! as it came down and smacked him on the behind.

“One,” Mommy said.

Jack let out a cry, but not because it hurt. The diapers provided more than enough padding for his behind. No it wasn’t pain that made him cry, it was simply the humiliation of being spanked in a diaper by someone who had no intention of ever letting him go.

The paddle hit his backside a second time.

“Two,” Mommy said.

This continued until Mommy said ten, at which point she held Jack to her chest, comforting him.

“There, there Jackie it’s all over.”

But Jack knew it was not over. It was only beginning.

SIXTY YEARS LATER

Sarah stood by the crib, crying as she looked down at Jackie. She had passed away peacefully in her sleep. She had changed so much since the day Sarah had caught her in the garden. She was older of course and had the wrinkles to prove it. She was toothless as a newborn. Sarah had removed Jackie’s teeth in her sleep one night so that she could start breastfeeding her. Jackie was also shrunk as she had gotten older, as everybody does.

Sarah walked back to her bedroom and laid down on the bed. She closed her eyes and thought about all of the joy that Jackie has brought her during their time together. She thought about her husband Richard and how much joy he would have gotten out of helping to care for Baby Jackie. She cried herself to sleep and in her sleep her heart gave out and she peacefully passed away.



Sarah felt a warm light on her face and awoke with a start. She was at the top of a large hill over-looking a small town. She could see many homes, some small some large. There were adults, men and women. And children too. “Where in the world am I?” she asked.

“Heaven of course,” she heard a man. She turned around to see a man of about ninety-years-old. He had salt-and-pepper hair, soft blue eyes, and a handsome face. He looked so familiar…

“Richard!” Sarah exclaimed. She rushed forward and threw her arms around his neck. They kissed each other, tears running down their faces.

A few feet away, an angel stood next to a baby carriage. He smiled down at the man trapped inside.

“Jack, you brought no good to Earth until you made Sarah happy. All she and Richard ever wanted was a REAL baby girl to care for. You are finally going to fulfill their wish.”

He held his hand out over Jack’s face and Jack felt warmth entering his body. Suddenly, it seemed he was watching from above. His body shrank, his head and torso becoming smaller and smaller and his arms and legs retreating. His hair shortened and thinned. His features became softer and he gained some baby fat. He felt his privates retreat in to his body and looked down just in time to see them replaced with a slip, which was quickly covered by a diaper. Then he was in a pink sleeper. He truly was a baby girl now.

He tried to yell, “No please, I’ll do anything!” But all that came out was: “Ya! Gi goo gabba goo goo!”

The angel smiled.

“Goodbye, Jackie.”

Jackie wailed and wailed until Richard and Sarah’s faces appeared over him.

“Is this…?” Richard said, getting choked up.

“Yes, this is our baby girl, Jackie.”

Richard had tears in his eyes again as he reached in to the carriage and picked Jackie up.

“I love you sweetie, I’ve been waiting for you and your Mommy for a long time.”

“And now we’re a family,” Sarah said, “forever.”

And in that moment something strange happened. Richard and Sarah began to change too. They were starting to get younger just like Jack had. Richard’s hair grew longer and changed from gray to black. His face lost its wrinkles and gained back its color. Sarah’s age melted away too. Suddenly they were the same couple Jack had seen in the wedding photo all those years ago. They were that young, healthy, joyful couple totally devoted to one another. Only this time they had they baby girl. And the three of them stayed that way forever.

The End

[Nanny Rachel]

What a great story...keep them coming...there were lots of twist there which was good...Rachel..