Mommy's Naive Sissy Ch. 01

Editor's note: this story contains scenes of incest or incest content.

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Note to reader:

This is pure fantasy, take it for what it is. Don't try in to inject realism into this story, it won't work! Just enjoy!

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My name is Jesse, I turned 18 this week. Mommy says we are going to have a special celebration all week long for my birthday!

When I was young, I always imagined that I had been named after the famous cowboy outlaw, Jesse James. However, growing up in a house full of girls, that illusion did not last long. And after my sisters moved away, it was always just Mommy and me.

My parents were divorced. My Dad had some high-level job with a big company and traveled incessantly, I hardly ever knew him. I never understood why Mommy put up with him, guess all the traveling eventually did their relationship in. My only memory of him was that he didn't like my sisters and Mommy treating me like one of the girls. Guess he was disappointed I would never be a macho, football jock.

We lived out in the country on a few acres of land, so we rarely saw any neighbors. I could run and play in our huge yard wearing whatever I wanted! Our TV broke when I was younger and for some reason, Mommy never got it fixed. I didn't have a computer and Mommy never let me use her cell phone. So, I never had much contact with the outside world. Looking back at it, I guess I have lead a sheltered life - but I wouldn't trade it for anything!

I had three older sisters; Kristen, Jill, and Melissa. I never felt like I knew them that well, however. The girls were all separated by about two years, then I came along. I am 7+ years younger than Melissa. I always thought I was a mistake or afterthought, although no one ever said that to me. My instinct, however, told me that I was not like the other boys I read about.

Puberty seemed to pass me by for some reason. I never had much body hair and I never went through any sort of physical change. Mommy noticed too I know.

"Jess, now that your 18, I think we need to face some facts," she told me the day after my birthday.

"What do you mean, Mommy?" I asked as we sat across from one another at our kitchen table.

"I think we both know that you are not like other boys," she said. "Do you even think of yourself as a boy?"

"I've never thought of myself as a boy, Mommy."

"I haven't either," she said. "I've always thought of you as my little girl, my fourth daughter. Today we'll start changing a few things, okay?"

"Whatever you want Mommy. I just want to make you happy."

"I just think, well, if we both consider you a girl, we should make that a reality," she continued. "I want to start dressing you like my little girl."

"Oh Mommy! I would love that!"

"I also think we need to do something with your tiny cock. In my mind I always referred to it as Itty Bitty!" she said with a smile.

"Oh Mommy! I love that name! From now one, we'll call her Itty Bitty!"

That day, that discussion, changed my life forever. I got the feeling that Mommy had been waiting all my life for me to turn 18 so she could "set things right" as she called it.

She handed me a birthday present wrapped in pretty pink paper. On the nametag is said, "To Jessica and Itty Bitty with love, Mommy."

I tenderly opened the package. Inside was the dress I always coveted! It had been Kristen's when she was younger. It was a white, sleeveless, shift with lots of lace and ribbons! There were pink bows on each of the shoulders and all around the hem! Mommy also included pink ruffled panties, white ankle socks trimmed with lace, and white, patent leather Mary Jane shoes.

"Normally, I think you should wear high heels. But we'll start with these shoes for now," Mommy said.

"Yes Mommy! I love high heels, and I love seeing you in high heels," I responded.

I lifted the dress out of the box and held it up to look at it. A tiny, pink, lace sleeve fell into my lap. It was elasticized on the open end. I picked it up and looked at it, wondering what it was for.

"That's Itty Bitty's outfit, it matches yours!" Mommy said proudly.

"Oh Mommy! You thought of everything! Itty Bitty will be so happy!"

Mommy had me drop my pants so she could show me how to put on Itty Bitty's outfit. Itty Bitty likes Mommy, she was twitching and trying to grow in Mommy's hand. Mommy petted her and even gave her a nice long kiss! Mommy is so sweet!

I gave Mommy a hug while she was still sitting in the kitchen chair. I felt my legs press against her boobies. It was such a special moment; I had never felt so close to Mommy. As she hugged me, she gently rubbed my bootie with her hand that wasn't petting Itty Bitty.

After Itty Bitty had her outfit on, I stepped into the dress and rest of my new outfit. It felt delicious! Mommy had her cell phone out snapping lots of pictures.

"Twirl around for me Jessica, I want to see those pretty pink panties!"

From that day on, I was Jessica, and my thingy was Itty Bitty. We never had many visitors at our house, but when we did, I was always introduced as Jessica and have lived my life as a girl ever since.

As my birthday week went on, Mommy had new surprises for me each day! The next day she told me she wanted me to have boobs like hers. Good thing I didn't argue, Mommy had already scheduled the surgery for next week! I will finally feel like a complete girl!

The day after that, she told me that I was going to start sleeping in her bed with her. All my new girl clothes would also be moved into her room! This was going to be so exciting, sleeping and snuggling with Mommy every night! I inwardly hoped we would get to wear fun nightgowns!

The last day of my birthday week, Mommy had one more celebration for me!

"Jessica, I think we should go out for a nice birthday dinner at a fancy restaurant!" Mom said.

"You can bring Itty Bitty along," she said with a smile.

For the occasion, Mommy had bought me what she called a "big girl dress". I hope Mommy will always pick out all my clothes! The dress was a light pink, classic shift with a V-neck. She liked me to wear sleeveless dresses whenever I could. She also bought me some light pink, patent leather, four inch, closed toe, spiky pumps. Mommy liked me in high heels. White thigh high stockings and white lacy panties and a push up bra completed the outfit.

Mommy was so thoughtful. She even bought Itty Bitty a special outfit for the occasion!

"I got Itty Bitty an outfit to match yours!" she said excitedly. "Drop your shorts and let see if she likes it!" she continued.

I dropped my shorts and panties (again!) and let Mommy have her way. She held up a tiny light pink nylon sack, complete with a tiny white ribbon that was used to secure the nylon sack behind Itty Bitty's tiny nut sack. She slipped the nylon over Itty Bitty and wrapped the ribbon around her balls, tying it at the top in a perfect little bow. Itty Bitty started to stir and grow, or, at least as much as she can.

"Oh! She likes it Jessica! Itty Bitty looks so cute in that nylon sack! It looks like she's wearing a stocking!" Mommy squealed. "I had it custom made for her! We can call it her cock stocking!"

Itty Bitty definitely liked the feel of the cock stocking, she loves nylon as much as I do! She was so excited she started to dribble.

Mommy was watching Itty Bitty intently.

"Let's take her cock stocking off, I think she's going to piddle. I don't want her messing up her new present!" Mommy said.

Mommy reached down and untied the bow and removed the cock stocking. Not a moment too soon either! Itty Bitty sputtered and twitched, and then she piddled all over the floor.

Mommy and I stood there and looked at the little piddle puddle on the tile floor in front of me.

Mommy smirked and said, "We have a new house rule Jessica. If your little friend there makes a piddle puddle, you need to lick it up."

"Of course, Mommy," I said as I got down on my hands and knees.

I put my tongue to the floor and lapped up Itty Bitty's piddle. I love the way she tastes!

Mommy had laid my outfit for the evening on my bed. The light pink dress blended in with my pink bedspread. The dress was more mature then I prefer, but it will make Mommy happy! Honestly, I prefer lacy ruffles and bows on my dresses! The white thigh high stockings were brand new and felt awesome as I slipped them on! My matching white lace panties and push up bra were sensuous! I felt like such a big girl! Mommy had helped me apply my makeup for the evening. I stepped into the pink patent leather pumps and immediately, Itty Bitty started twitching!

"Naughty girl Itty!" I said to her chuckling. "You just piddled a while ago, you'll need to wait a while for your next one!"

Later that night we were enjoying a wonderful dinner at Mommy's favorite restaurant.

About halfway through the meal, I said, "Mommy, Itty Bitty needs to tee tee."

"That's fine dear, go ahead and take her to the ladies' room," Mommy said. "Do you want me to come help you with Itty Bitty's stocking?" Mommy asked.

"No Mommy, we can take care of it," I said confidently. I wanted to show her I was a big girl now that I was 18!

I guess I was gone too long, Mommy seemed upset when I got back to the table.

"Honey, where have you been? You've been gone for almost 20 minutes. Did you get Itty Bitty's stocking back on her?" Mommy asked.

"With a little help, yes," I replied.

I proudly held up a dollar bill.

"I earned a dollar while I was gone!" I said proudly.

Mommy raised an eyebrow and said, "And how exactly did you do that?"

"A nice man gave it to me!" I exclaimed.

I went on to tell Mommy how when I was walking out of the ladies' room, Itty Bitty's stocking fell off. I guess I didn't tie the bow tight enough! It fell out of my panties and right onto the floor! A nice man saw it, picked it up, and handed it to me!

"Is this yours young lady?" he said smiling and holding out Itty Bitty's stocking.

"Oh, my goodness! Yes!" I said blushing and taking the cock stocking from him. "It actually belongs to a close friend of mine," I said smiling.

"Your friend must be very small," he continued.

"Oh, yes she is!"

He then asked if he could meet her. I sort of stammered and didn't know what to say. He then offered me a whole dollar to go out to his car and introduce him to my friend. I thought Itty Bitty wouldn't mind, so I said yes!

We went to his car and sat in the front seat. I lifted the hem of my dress and pointed to Itty Bitty under my panties.

"Her name is Itty Bitty, she's pretty shy," I told him.

He asked me to take off my panties so he could see her better, which seemed like a good idea to me.

"My, my, she is very cute!" he said. He petted Itty Bitty gently and then handed me the dollar bill.

I told him I needed to get her cock stocking back on and get back to the table, my Mommy was waiting for me. The nice man helped me with Itty Bitty's stocking and even tied a nice bow to keep it in place. In my hurry to get back inside the restaurant, I left my panties in his car!

"So, you're not wearing panties right now!?" Mommy asked.

"No Mommy. And I think Itty Bitty likes it like this!" I said, blushing.

"She's twitching right now?" Mommy asked with slight concern in her voice.

"Yes Mommy"

"Is she going to piddle?"

I just looked Mommy in the eye and nodded yes. Mommy rolled her eyes and handed me her cloth napkin.

"Put this under your dress to catch Itty Bitty's piddle," Mommy told me.

I lifted my dress and stuffed Mommy's napkin on top of Itty Bitty. I was just in time! She sputtered her piddle and it quickly leaked through her cock stocking and soaked Mommy's napkin. Mommy was watching my face as I sort of glazed over with the rush of an orgasm.

When Mommy sensed that Itty Bitty was done piddling, she said to me, "Wipe your mouth dear, you have a crumb on your bottom lip."

I looked at Mommy and smiled. We both knew there was no crumb on my lip, she just wanted me to enjoy Itty Bitty's piddle from the napkin - which of course I did!

To be continued...