Ugly Duckling to Sissy Princess Ch. 02

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JHouston
JHouston
451 Followers

Bernice said she knew just the place and took me to a boutique store downtown.

She picked out a lovely sequin tube dress that was tight-fitting and short, but not too short. It showed lots of leg, but, stopping short of being slutty. It also had small cutouts on the sides. "You'll look so hot in this!" Bernice whispered in my ear.

Then, she went to pick out stilletos and stockings.

Bernice was my cover. She would pretend to be picking out all these clothes for her. Then, I would try them on in the fitting room.

She pulled me towards the fitting room and told the clerk that she was going to try somethings on, but, she wanted me in the fitting room with her to tell her if I liked it.

The clerk's name was Clara. She was a cute petite Latin woman with long bond hair in her 30s. She said she was not supposed to let couples go into a fitting room together, but, she said she would make an exception for us, so long as we promised to behave.

I was embarrassed about changing in front of Bernice, but, she started pulling my clothes off like it was no big deal. I was completely naked, with my hands covering my dick, and Bernice helped me put panties on and the dress.

Then, she helped me with the black sheer pantyhose and with the stilleto shoes. Her help dressing up was very sensual. I gained about five inches with the stillettos and I was almost the same height as her.

Bernice pulled out the short black wig and put it on me. She adjusted it, until she was satisfied with it.

"You look so pretty, even without any make up on." She said and squeezed my ass.

The one benefit of having a small dick is that erections are not so conspicuous. However, in a tight fitting dress with thin fabric, even small dick erection are conspicuous.

Bernice noticed it and giggled.

"Its so small and cute!" She cooed. I turned red with embarrassment.

"Play with it, sissy." She whispered in my ear.

I ignored this request, thinking she could not possibly be serious.

"Seriously, you fucking little sissy, let me see you play with your tiny pecker!" She commanded in harsh new tone.

"You are joking right? I am not doing that!" I protested.

Like a switch, the sweet giggling Bernice transformed into a dark and moody bitch that you do not want to fuck with.

In a menacing voice she spoke in my ear, "Do as I say or I'm leaving you here with nothing but the sissy clothes you have on. Good luck getting home like that."

I looked at her. Was she kidding?

She must have read my mind. "Not kidding." She said. "You haven't seen my dark side. But, trust me. You're better off doing exactly what I tell you to do right now!" She threatened.

"Bernice, no! What the fuck! We need to get out of this fitting room or we will get in trouble!" I said.

She grabbed the clothes I had taken off and was about to leave with them.

I grabbed her arm. "Okay! Fine!" I said.

"Get on your knees, sissy, and play with your little peepee." She commanded.

I lifted my dress, got on my knees, and started playing with myself. This was humiliating, but, I had to get through it. I closed my eyes to concentrate and be done with it quickly. It was actually easier than I thought. I just had to think about Bernice.

Then, getting right in front of me, she put her right index finger on my lips. She said, "Give my finger a blowjob."

"No!" I said defiantly.

Bernice grabbed my regular clothes, and again, threatened to leave with them.

"Okay, okay, okay!" I said.

I started to suck her finger. I was shy at first, but, she encourage me saying things like, "Oh, that is good, baby! Yeah, tease the head! Fuck that finger with your mouth!"

She thrust her finger in and out of my mouth while grabbing and pulling on my hair. As weird as this shit was, I was getting very aroused very quickly.

She whispered, "You love sucking cock, don't you, little sissy!" and that pushed me over the edge. I started to cum.

"Do not a drop on the floor! Collect all of it in your hands or I will make you lick it off that disgusting floor!" She said.

I managed to catch all of it in my hands.

I was still on my knees and I told her, "I need napkins, please. Can you bring me some?"

She gave me an evil grin. "Napkins? No, no, no! You are going to eat your own cum and lick your hands clean!" she said.

"That is fucking gross! I'm not doing that!" I said.

Suddenly, we heard Clara. "Are you guys almost done in there?" She asked us. "Almost." answered Bernice.

Bernice whispered in my ear, "How would you like to get caught in this fitting room in that pretty dress, pantyhose and stilletos, and holding your cum in your hands? They will call the cops on you, sissy!"

"You wouldn't!" I said as I started to get on my feet.

Bernice pushed me back down on my knees and said, "Are you prepared to make that bet? That would be a very serious gamble on your part!"

"I can't do it!" I said sheepishly, hoping she would have some mercy.

"Okay, I am going to help you." She said, sounding like a teacher that is helping a student with a math problem.

"I am going to teach you a visualization trick to help with your task. First, close your eyes." She said.

I closed my eyes.

"I know you have fantasized about sucking Ted's big fat cock. First, you need to admit it! So, go ahead and admit it, right now." She commanded in my ear.

I wanted to end this ordeal, so I reluctantly admitted it. "Okay, fine, a may have fantasized about it once or twice." I said.

"See now? Isn't it good to finally admit it?" She said.

Then she added, "You know, you have no reason to feel ashamed about it. Hell, every sissy wants to suck Ted's dick. Most of them already have."

She added, "But, you don't want to be an average-rate cocksucker. That will disappoint him and he will lose interest in you. You want to be a superb class A cocksucker!" She said.

"I can train you." She said.

Bernice grabbed my cum-filled hand and pushed them into my face. I had my own cum all over my face.

"Keep your eyes closed." She said.

"Now, visualize this." She said in a hypnotic voice.

"You have just given Ted a world class blowjob. He is very pleased with you and he has shot his load all over your face and lips and it has also spilled on your hands." She said.

"Show Ted how much you worship his cum. Lick your lips. Lick your hands. Savour Ted's cum!" She encouraged me.

As if in a hypnotic trance, I licked all the cum off lips and my hands. I kept licking even after there was no cum left to lick off.

It was a weird taste, but, not so bad - a little different than the cum I tasted in Carol's mouth. I guess each cum has its own distinctive flavor.

Bernice kissed me on the lips when I was done. "You passed your first test." She said and pulled me up on my feet.

I was about to remove my girl clothes to put my boy clothes back on, but, Bernice opened the door to the fitting room and gave me a hard push out!

"No!" I screamed! Bernice closed the door behind me and locked it!

"Why Bernice? I did everything you asked me to do!" I yelled at her.

"Please open the door! Someone is going to see me like this!" I actually started to cry in desperation.

Clara walked over and saw me crossdressed! I was mortified and covered my face with my hands.

"Bernice is such a bitch!" she said laughing. Apparently, they were friends and decided to play a prank on me.

"It's okay, honey." She said patting my shoulder. "We cater to crossdressers and transgender girls. This is a safe place and a no-judgment zone."

Clara hugged me and I hugged her back. I was so relieved by her words.

Bernice came out the fitting room laughing hysterically. I looked at her with hate. "You fucking bitch!" I cursed at her.

She was unfazed. "You have to get used to my dark sadistic side." She said.

Then, she grabbed my hand and pulled me towards a door at the back of the store. Clara grabbed my other hand and the three of us walked together. I was still wearing stillettos and they helped me walk without tripping over.

"Where are you taking me?" I asked them.

"There is a make-up room on the back of the store. Clara is the best make-up artist in town." Bernice said.

For the next hour and a half, Clara and Bernice worked on my face. I sat on a high chair in a room full of make-up. There was make-up everywhere.

I had seen my girlfriend put on eye liner and lipstick, but, I did not know there was so much make-up products that a girl could use on her face.

They layered my face with stuff and then added more color on top.

They experimented on me like scientists or artists, trying on different shades of different things. When they discovered the perfect tones for my skin, they wrote it down on a piece of paper for me to keep for future reference.

The nice sweet giggling Bernice was back and Clara was also nice and sweet lady. It was a fun experience to have them both do my make-up. I felt like one of the girls.

They also did the nails on my hands and feet!

I have to say that this experience was delightful! I almost did not want it to end.

"Wow!" - they both said in unison, admiring their own work. I wanted to see for myself, but, they kept me facing away from the mirror.

Clara went to fetch something and brought back a pretty box of costume jewelry. They put a lot of glittery and pretty costume jewelry on me, including, rings, pearl necklace, clip-on earrings, and even toe rings and an ankle bracelet.

"Almost done. Only a couple of more things." Clara said looking at Bernice. Bernice looked back knowing exactly what those thing were.

"Small and perky." Bernice said.

Clara left the make-up room and came back a minute later with breast forms.

The girls taught me how to put them on and, suddenly, I had small and perky breasts.

"And, what is the other thing?" I asked. They looked at each other and giggled.

Bernice pulled out something from her pocket. It looked like an itsy bitsy little steel cage and I looked to see if there was some tiny little creature inside. But, it was empty.

"What is that?" I asked.

"Pull your dress up and your panties down." Bernice told me.

"What are you going to do?" I asked, puzzled.

"It's a cock cage. You don't want your little peepee getting excited spoiling your feminine impersonation." She said.

Bernice was not shy at all about grabbing my dick to put it in the cock cage. The cock cage had a lock. Bernice locked it and put the little key back in her pocket.

"Give me the key!" I said.

"Trust me, it's better I keep it in a safe place. If you take this key and lose it while you are dancing tonight, you will need a locksmith to free your peepee." She said.

I was not sure I could trust Bernice, but, I looked at Clara and she seemed to agree.

I put my panties back on and fixed my dress.

With their work complete. They both stared at me beaming.

"What?" I asked. "Can I see now?"

They splashed some perfume at me and turned my seat around so I could see my reflection in the mirror, and I almost fell off my chair.

I stared at myself stunned. All three of us stared at me with amazement. I stood up and admired myself from every different angle.

I was finally able to say a word. "I am beautiful!" I said.

"Yes, you are a princess. You need a princess' name." Said Clara. "How about Diana or Victoria?" She asked.

"Oh, don't say things like that to her." Snapped Bernice.

"You want it going to her head, so she thinks she's some beauty queen?" Bernice asked.

"Vicky, that'll be her name. Vicky is not princess, she is my bitch and my slave!" Bernice said.

"She'll be mine to abuse and train, until it is time to pass her off to Ted." She added.

Then, Clara said to Bernice, "Ted is going to have such a major hard-on when he sees her. Vicky is going to be a big hit at the party!"

Bernice nodded.

"You think Ted can keep his hands off her for now?" Clara asked.

"It'll be hard with this one, but, he better. He has already made that mistake once. I'm not going to let it happen again. I will train her to know what to do and prepare her for all the challenges." Bernice said.

"You cannot throw these newbies to the lions without some training. Ted can get pretty rough." Bernice explained.

I kept starring at my own reflection and ignored their crazy talk. I was sure they were talking a lot of shit just to fuck with my mind.

I was so giddy and excited by my transformation! I was stunning! Even Carol would look plain and ordinary standing next to me right now.

Bernice called Ted to tell him I was ready. He was already on his way to pick me up for the party.

"You'll have trouble keeping your cock in your pants. But, you be a gentleman tonight!" I heard Bernice say to Ted on the phone.

"Don't you fucking touch her tonight, even if she begs for it. You have to let me train her, first." Bernice said emphatically.

She hung up the phone and announced, "He will be here in ten minutes!"

The next ten minutes seemed like an eternity. The girls gave me instructions on how to sit, stand, walk, smile, talk like a girl, flirt, etc.

The only thing they did not have to teach me was how to be a nervous wreck.

Bernice got a text from Ted telling her that he had arrived and was outside waiting in his limo.

Suddenly, I felt light-headed and dizzy. I thought my knees would buckle.

I told the girls, "I changed my mind! I cannot do this! My head is spinning!"

They giggled and each of them grabbed my hands and led me to the door.

My heart was pounding so fast, I thought I would drop dead any second.

We opened the door and there he was.

Ted looked at Bernice and Clara, still holding me. Then he looked straight at me - his eyes scanned me up and down.

His mouth formed the biggest grin I have ever seen. He was delighted by what he saw.

I noticed, for the first time, how handsome he is. He is very tall, dark and solidly muscular with the face of a black Adonis.

He looked very sharp and dapper in his black tuxedo.

I felt like a high school girl going on her first date, and not with just anybody, but with with the hottest guy in school!

I walked slowly towards him, trying to be graceful.

He walked towards me and we met half way. He took both of my hands while facing me.

With my heels on, I was a lot closer to his face, though he was still at least a foot taller. We gazed into each other's eyes for a minute. He smelled of fine gentleman's cologne, and, he had taken some breath mints, because his breath smelled nice and minty.

"My name is Vicky." I told him.

With a wide smile, he asked me, "Vicky, how do you feel?"

"Nervous!" I said nervously.

"But, I like how I look!" I had to admit. "Thank you for paying for it." I told him.

"I knew you would look amazing, but, you have surpassed my greatest expectations!" He said.

I blushed and looked away.

"You look very nice, too." I said sheepishly to Ted.

He led me to his black stretch limo and gently guided me inside.

Before I got in, I looked back at the girls. They were still standing in the same spot and looking proudly at me. I waved them good bye and mouthed the word "Thank you!"

They waved me back smiling.

Ted got in and the limo, and we took off.

Ted reach over to hold my hand and we gazed at each other, and nervously laughed. His dark brown eyes looked down at me with attraction and desire. I felt incredible! No one has ever looked at me with such intensity!

At that moment, one thing became crystal clear to me. I was completely under his spell. He could get me to do anything he wanted.

I closed me eyes, because I was suddenly very scared.

I felt his hands touch my face and pulling me closer to him. I could feel his breath on me as our heads came closer together.

I kept my eyes closed knowing that our lips were about to meet.

When our lips made gentle contact, my mouth yielded to him in a quick and quiet surrender.

His tongue met no resistance in its invasion and penetration of my mouth.

JHouston
JHouston
451 Followers
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AnonymousAnonymous7 days ago

Sorry had to quit reading when this just became a recap of the first story we don't need that we just need a new story dislike

MichaelfantasiesMichaelfantasiesabout 2 months ago

This part 2 has gotten "Vicky" in much deeper and quicker than I expected! I'm not sure if I could go along with everything Bernice was expecting, like wearing a chastity device! I'd be so terrified if someone wanted or expected me to wear one! Such things would be going to fast, for me! For "Vicky," though, is seems like "she" is accepting these things quite well ! Then again, she has Ted !

mumblegooseeggmumblegooseeggalmost 7 years ago
I'd love to be Vicky too

...but unfortunately I am 6'1" and 250 lbs (and a senior citizen on SS and Medicare) so I guess I'll never meet a Caroline or a Ted. Oh well, I'll just read on, fantasize and wank off. Isn't that what Literotica is for?

Great story, JHouston!

AnonymousAnonymousalmost 7 years ago

God, i wish i was Vicky. my dressing has never been this wonderful. Your story is making my little sissy cock so hard.

AnonymousAnonymousalmost 7 years ago
Soooo HOT!!! 💗

This story has me soooo HOT! I can feel exactly how Vicky feels, and I LOVE it!!! 💋

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