Twenty year old Mary Kent was happy. She had been left with her younger step brother Terry in the big manor house that had been in Terry's family for generations. Mary's mother Elizabeth had married Terry's father 6 years ago, and in that time Mary and Terry had become close. Terry had taken to Elizabeth as well and she to him. They were a happy family, save for the fact that Terry's father Thomas was a workaholic who was rarely home. Elizabeth had finally gotten Thomas to agree to a romantic getaway, so that left Mary and Terry alone for the summer. Once a week, Sally Masters the grounds keeper and her wife Tammy came by. Tammy cleaned the house and grocery shopped for them, while Sally tended the yard, other then that the two were pretty much left alone.
Mary, like her mother was tall and athletic, she had green eyes and blonde hair. She was intelligent and kind, and was very good at reading people. Terry, also took after his mother, he was short and petite and even though 18 he had no facial and very little body hair, his eyes were also green and he too had long blonde hair. He called it his rock rebel hair, but he really wasn't fooling anyone, he looked like a girl, and Mary often dressed him up in her old clothes. She would put make up on him and take him out as her little sister. Terry made such a convincing girl that nobody ever suspected he wasn't a boy.
Lately Mary had gotten the idea of making Terry her little baby sister. She had discovered a magazine Terry had hidden called Frilly Frolics, in it were stories of boys and men dressed up as baby girls. Intrigued, Mary searched the internet and found everything she wanted to know, including all she would need to satisfy Terry's secret fantasy. She enlisted the help of Sally and Tammy, Sally's family had worked for Terry's for generations so Mary knew they could be trusted, also she liked them as well. Mary spent quite a bit of money on turning one of the spare bedrooms into a sissy fantasy for Terry. She had taken him out for the day dressed as a teenage girl, he wore a floral baby doll dress with tights and a ribbon holding his pretty hair in a pony tail. Mary took him shopping and to a movie, then to dinner, giving Sally and Tammy plenty of time to do their thing. Now at last everything was ready and Mary walked into the living room and over where Terry was sitting.
"I'm bored," She declared as she sat down next to him, "wanna play with me?"
"What shall we play?" Terry asked looking up from his book, he loved Mary and would do anything she asked of him.
"A dress up game," Mary declared, "I pick a costume and you wear it and roll play for the rest of the day."
"Why do you get to pick?" Terry asked playfully
"Because I thought of it first, and because I am older wiser etc." Mary said with a laugh and held out her hand. "Come little sister."
"Ok. I submit, as always." Terry said with a theatrical sigh as he took her hand. He would often protest when she dressed him as a girl, pretending he didn't like it, though they both knew he did.
She led him down the hall towards his new room.
"I have decided that you are going to be my little baby girl!" She opened the door with a flourish and Terry nearly cried with joy at the sight of the pink frilly princess dream bedroom. A large pink crib more than large enough for petite little Terry dominated the room, there were stuffed toys, dolls, a closet bursting with frilly dress after dress, a huge doll house and pink toy box lined another wall, a pink dresser and changing table below cabinets and shelves full of cloth diapers powders creams etc.
"Oh my God.....how did...." his voice trailed off in wonder
"Don't be mad, but Sally and Tammy know, I needed their help to make this surprise for you." Mary cupped Terry's face in her hands and kissed him in a very un sisterly way, "I love you baby girl, I know that's what you are, and it's ok. I was snooping and I found your Frilly Frolicks, so I know this is what you want."
"I...I do, I really do want to be a baby girl.....I don't know why......" Terry's eye's welled with tears and Mary kissed them away.
"It's ok Terry, I love you and Mom loves you. She will be ok with this I know she will, and Dad won't even notice he's hardly ever here." Mary began to help Terry out of his sweat shirt and sweat pants, "I am dying to get you dolled up as a 2 year old girl, hurry honey lets get you naked."
In no time Terry was naked and lying on the changing table, waiting for his beloved step sister to transform him into the sissy baby they both knew he really was.
Terry got an erection as Mary slid a thick cloth diaper under him, "My baby loves her diaper doesn't she?" Mary said with a laugh as she sprinkled powder liberally on Terry's bottom before pinning him snugly in the soft diaper with pink ducky diaper pins. She popped a pink soother in Terry's mouth and pulled pink plastic panties up his legs and over his diapers, rubbing the front of his diaper with her right hand and smiling at him. Terry gasped with pleasure as Mary increased the pressure and rubbed faster until he climaxed less than a minute later with a satisfied sigh.
"My little baby doll is excited isn't she precious?" Mary asked him in a syrupy voice.
"Yeth Mary I am Thawk you" Terry said with the soother bobing in his mouth.
"Your welcome my darling." She leaned down and kissed him warmly and Terry felt like the luckiest sissy baby in the world.
Mary had him sit up and slipped a white sleeveless petti dress over his head, it as fluffy and short, so short that it would leave Terry's diaper half exposed which is exactly what Mary wanted. Next she put a pink empire waisted baby dress on him over the white petti dress. The pink baby dress was just as short as the petti and it had puffed short sleeves adorned with pink lace as did the 3 tiers of lace that hung down from the adorable empire waist which was adorned with frothy pink lace.
"Lie back down Princess." Mary cooed as she put thick pink rhumba tights up Terry's legs over his panties and diapers, the tights were baby pink to match the dress and had 5 rows of white lace across the seat over Terry's thickly diapered bottom. White lace anklets and pink Mary Jane shoes were soon on his feet, and Mary deftly tied his hair with 2 pink bows into adorable pigtails and after adding a little makeup she steered Terry in front of the full length mirror.
The young sissy swooned at the sight, he looked exactly like an adorable toddler princess. "Oh Mary thank you thank you thank you!!" He jumped up and down with pure joy and leapt sobbing into her arms. Mary easily held him against her and Terry wrapped his arms and legs around her as she carried him out to the living room and sat down in the plush rocking chair cradling Terry on her lap. She kissed his tears away and told him she loved him and that he was her sissy baby from now on, and that they would be together always.
From the chair's side pocket she pulled a baby bottle of apple juice , Terry's favorite and teased the nipple into his mouth. Terry suckled contentedly knowing he was loved and that his fantasy of being a pampered toddler princess was coming true. He looked up at Mary and she beamed a smile down at him and they both felt bliss.
The end
Just a short story, I hope you liked it. Thank you for taking the time to read it. :)
