A New Life For Sissy

Dear Auntie Helga,

After my initial petticoating at Terri's house on the river bank, I did not go back for a visit during the following two weeks. I was afraid of how they might dress me, where we might go, and who might see me dressed like a prissy sissy. But, I soon learned that I could not escape so easily.

On a bright sunny Saturday morning, Terri and her two closest friends, Babs and Iris came to visit me at my house. When I saw who was at the door, I nervously invited them to come in. Mom was happy as usual to see them. She always seemed to prefer that I kept girl friends rather than the boisterous boys that I sometimes hung out with.

My Dad had passed on some years earlier. I had an older brother who was away in the Navy. So, it was just myself and Mom.

Terri and Mom had become very close. "Did Toby show you the baby doll that Ruth gave him during his last visit to our house?", asked Terri.

"Why, no he did not", answered the older lady ( every bit of 37 ). "Toby, bring me your dolly and let me see it". I reluctantly did as I was told. I brought my dolly and handed it to my Mom.

"Oh my!", said Mom. "What a lovely little boy dolly. What is his name"?

"Pansy", I answered shyly.

"Oh, such a pretty name for a sweet boy. I have always liked boys to be sweet, gentle, and yes, just a little girly too".

"At our house, Sissy likes to dress up in little girl's clothes", blurted out Terri. She even surprised herself with her boldness.

"Sissy?", asked Mom. "Do you girls call Toby, Sissy now"?

"Oh, we do so only with a touch of love", answered Terri. "Toby is...well...like one of the girls. We all adore him, just the way he is". The 15 year old girl was now wondering just how deep she had plunged her foot into her mouth. But, her fears were soon expelled.

"I am so happy that you wonderful girls have brought this to my attention", began Mom. "I have wanted to dress my son in girly things for years now. Wait right here. I have something to show you".

While Mom ( all the girls called her Mom too ) was out of the room, Terri quickly showed me some of the pictures she had taken on my last visit. These were taken with me wearing a very revealing yellow one-piece girls swim-suit. I knew at that moment that I had better cooperate.

Mom soon returned with a photo album. "These are all pictures of my brother, Marty. Even though he was 2 years my senior, he was always submissive to me. I even baby-sat him when we were left alone. I always enjoyed having an obedient jane-boy brother to tease and dress up. Now, I have my very own jane-girl son to love and adore".

The pictures were of my Uncle Marty at various ages of childhood. He was mostly wearing dresses, but also girly boy-suits or girlish shorts. In some pictures, he was wearing a diaper. There was even a picture of him at perhaps 17 years old in only a short-waisted blouse and a white cotton diaper. There was also a picture of Mom giving Marty a bath.

"We were afraid that dressing Sissy up in girlish attire might make you angry with us", spoke Babs.

"Certainly not", answered Mom. "In fact, it makes me very happy. If we keep Sissy dressed up in prissy feminine frillies, he is not so likely to be roaming off with those dreadful neighborhood boys. There is no telling what mischief they might get into".

"Maybe we should go ahead and get him into something more girly right now", suggested Iris.

"Brilliant idea", insisted Mom. "But I do not have anything right on hand".

"I brought a pair of shorts, just in case the weather were to get really hot today", said Babs.

"And Sissy already has his own panties", added Terri.

"Run and pick out a pair of panties for yourself", demanded Mom. I did as I was instructed. I picked out the biggest pair of panties that I owned. They were baby-pink bloomer-style, with a high waist and long legs. I thought that I was being clever. I was wrong.

At the sight of the bright baby-pink panties, Mom smiled and the three girls giggled. "Now, take off your clothes so that we can dress you, Sissy". Even Mom is now calling me, Sissy. Nervously, I did as I was told. The girls could not contain their girlish giggles as I found myself standing before them totally nude.

Mom held out the panties that I had myself picked out to wear. "Step into your sweet panties, Sissy". I did as directed. Mom pulled them up nice and snug. Then, she had me to do three deep-knee bends. This became a ritual, as it causes tight fitting panties or tights to fit properly.

Then Iris held out the lime-green shorts. "Step into these now, little Sissy", she ordered. I obeyed. I was not happy in the way they fit. My panty waist appeared high above the elastic waistline of my green shorts. And the short shorts were shorter than the legs of the bloomer-style panties.

Then Mom found me a girlish short-waisted T-shirt with a little pink bow at the throat. "Now, lets get her nails painted, some lipstick, make-up, and some sweet smelling perfume. All the girls pitched in. Then Mom tied a big pink bow into my hair. After that, I put on my uni-sex white sandals.

You look adorable!", exclaimed Mom. "We will have a great deal of shopping to do later. But for right now, you may go out and play with your wonderful friends. I am going to love having a sweet girly son".

I reluctantly went outdoors, carrying Pansy, with Terri, Babs, and Iris. I could not have been more nervous if I had been totally naked. "I look like a sissy!", I exclaimed, with tears in my eyes.

"Your name is, Sissy", reminded Terri. And my name has been Sissy ever since those long ago days.


Thank you for your letter Sissy. Your mother obviously did the right thing with you.

Auntie Helga

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