Ugly Duckling to Sissy Princess Ch. 03

(Continued from Part 2)

Wow! The kiss! Wow!

Before I knew it, I was sitting on Ted's lap straddling him and we were French kissing in the most passionate and intense kiss of my life!

I don't even know how I got up here. Maybe I climbed on his lap or maybe he grabbed me and pulled me up here.

I was in bliss! The kissing was so amazing that my whole body just melted into it!

His big tongue penetrated my mouth and my small tongue welcomed the invasion and danced with his.

With Karen, I was always forcing myself to play the role of man who takes the lead and I was always awkward and clueless.

It was so much better with Ted, he took the lead and he clearly knew what he was doing!

All I had to do was submit to him. It was so delicious to submit to him!

Then, I felt something long and thick crawling between Ted's lap and my ass, and, I jumped up in surprise!

What the fuck was that?

The kiss had fried my brains, but, as the gears slowly started moving again, my brain said to itself - "It's his cock, stupid!"

Holy shit! It felt like a fucking animal crawling under me! Can a cock really be so long and thick?

Then, suddenly, I was back in my seat. He picked me up, like I weighed nothing, and placed me back in the seat next to him.

"Why did we stop?" I said nervously. Even though his cock has startled me, I did not want the kissing to stop.

He did not look at me. He just straightened up his shirt and tie and said, "We shouldn't have done that. It's too soon. You don't know what you are getting yourself into. Tonight is only about going to the party and having fun, nothing more."

I don't know why, but, his words stung like hell! Was he turning me down? One minute he was treating me like a beautiful princess, and he next minute, he was pushing me away?

What the fuck!

I faced towards the window and gave him my back. I was so pissed off!

Suddenly, I felt his hand on my shoulder, and he said to me, "Hey, I've got something for you."

I did not want to look at him, but, I turned around.

He had a square box in his hand and he wanted me to take it.

I took it and opened it. It was a leather choker. It sort of looked like a bondage choker, except it was very cute, with a little golden heart lock and golden chains. The lock had a tiny stone that looked like a diamond. On the back, it had golden letters, "OWNED BY TED".

"What is this?" I asked.

"It's a gift. It's real gold and a real diamond. It's so other people know you are with me." He explained.

What did it mean? I asked myself.

I was getting mixed messages from him and I wanted to scream!

"Well, what about you? Shouldn't you get one with my name on it?" I asked him.

"Touche." He said, giggling.

"Look Jason, I mean, Vicky, you need not worry about me. I am not going anywhere until we both figure out what we will happen between us. This choker is more for you protection. You will attract a lot of attention and it may be overwhelming to have every guy at the party hitting on you. This choker will make it known to everyone that you and I are - um - hanging out, so that you will not be harassed." He explained.

"Well, what if I want a lot of attention and a lot of guys hitting on me?" I asked him to see if that would provoke him.

For the first time, I saw his face transform into a cold and angry expression.

Before he became turned really angry, I said, "I'm kidding! I'm kidding!"

His jealous reaction confirmed to me that there was something he felt for me.

"Ted, I'm scared to death of tonight, I want to stay by your side the whole night." I said holding his hand.

I put the choker on, and said to him, "Thank you for this. I really mean it. It is a beautiful gift and very thoughtful of you to protect me like this."

His face went back to smiling. He had a great smile.

We sat in silence while as the limo drove on.

Then he finally said, "About before, it's not that I did not want to keep kissing you, it's just that, I noticed how excited I was getting and I don't want to rush you into anything. Besides, Bernice made me promise to keep my hands off you. She's taken a real liking to you and wants to make sure you are well prepared before you try anything with me. I can be really intense, and, I think you already know that I am very well-endowed. You need to proceed with caution."

He smiled. I looked away blushing.

Then, I felt obliged to be honest with him, "To be clear about something, Ted, whatever happens between us, - I'll play with that thing and do things to it that you will love, but, it is never going inside my, you know, butthole."

He giggled.

"Seriously!" I said. "That thing could tear and rip my butthole and I don't want to end up in the emergency room dressed like this and with a stretched out and ripped butthole." I said.

He roared in laughter. Was he taking me seriously?

When he calmed down, he said, "Bernice knows how to train sissies and she knows how much a sissy can take. Look, if after a month she says your ass can take it, I will pound and ravage your ass like my bitch. If she says it is too small for my big cock, then, I'll settle for something else from you, and I won't be disappointed." He said sounding sensible.

He made this offer in such a casual and reasonable tone, and with his eyes gazing at mine, and I got lost in his charm.

"Fair enough," I said, without fully processing it.

Seconds later, it hit me that I had conditionally agreed to have full sex with him. I regretted my answer. What the fuck was wrong with me?

Before I could think of some way to back out of the deal, the limo stopped.

"We're here!" Ted said excited.

I looked around. There was a big wrought iron gate and tall walls surrounding a large gated community.

The limo driver talked into an intercom, and the gate opened.

Once past the gate, we entered a wooded property and drove past beautiful trees for another five minutes.

Then, I realized it wasn't a gated community. It was all just one estate, and, at the end of the road was the biggest mansion I had ever seen in my life.

I took a deep breath.

We reached the bottom of big marble stairs that lead up to gigantic doors of the mansion.

There was a gorgeous water fountain with three bronze horses about eight feet tall.

About five attendants stood ready to open car doors for guests. They immediately recognized Ted, and said to him, "Welcome back, Mr. Knight."

"Who lives here?" I asked Ted.

He answered, "Nobody."

He noticed my puzzled look and explained, "This house is owned by one of my clients, Stefano Francesco, but, he doesn't live here. He is an Italian billionaire and owns several dozen mansions like this across the world. No one actually lives in this mansion. He stays in it sometimes or it is used to host parties."

I looked up at the stairs. There must have been at least twenty steps to climb.

It appeared to be made out of stone and had six floors. It was magnificent!

As I started walking up the steps, a young attendant about my age saw me wobbling a little in my high heels and ran to assist me.

"Please, allow me to assist you up the stairs, miss." He said humbly. "Sure, I said."

I knew that he was checking me out, but, he looked down sheepishly when I looked at him.

Ted held my left hand and the handsome young attendant held my right hand. It felt nice to have two men holding my hand and helping me climb the stairs.

When we reached the top, the doors opened. It took four attendants to open the giant doors.

Oh my God! It was so extravagant on the inside! The ceilings of the grand foyer were about three floors high with art painted on the ceiling and and the most amazing chandeliers hanging from the ceiling and sparkling so bright!

The architecture was so rich and elaborate, with columns, arches, coves, crown molding and other fancy stuff like that all over.

There were statues, scultures and paintings everywhere.

Two giant magnificent marble stairways started on opposite ends of the room and converged up on the third floor leading to the bedrooms.

We passed under the stairways and walked down a wide long corrider until we reached the grand ballroom where the party was in full swing!

The grand ballroom had a DJ booth at one end and dance cages at the other. The floor vibrated with the thunder of the sound system.

The place was lit with candles and nightclub lighting - lazers and colored lights dancing on the walls, floor and ceiling.

The people looked beautiful and glamorous.

The women were very young, stunning and glamorous.

The men were older and less attractive. But, the beautiful tuxedos they wore made them seem ten times better looking.

"These are real women. I though you said it was a crossdressing party." I asked Ted.

"I'd say about 70% of these real women have cocks, and the other 30% used to have cocks." Ted said smiling.

"Unbelievable!" I said. "They are so beautiful!" I said amazed.

Then, the DJ shifted gears, switching from a Beyonce dance song to a love song, Thinking Out Loud.

Before I knew it, Ted had pulled me into the middle of the dance floor.

"I can't dance! I'm still learning to walk in heels!" I said to him.

He put his arm around my waist and said he would carry me, if necessary. I believed him, he was so strong.

He held me close while we danced and I rested my head on his wide shoulder.

I wanted him to kiss me so bad, and from the look on his eyes, he wanted to kiss me, too! But, it didn't happen. Whatever "training" I had to go through with Bernice, it would be so worth it to be able to kiss this man.

After the slow dancing, we walked around and Ted introduced me to many people.

All the men seemed to be middle aged and older and very wealthy. You could smell the power and money on them, but, they acted very cordial and sweet with me.

"Who are these men?" I asked Ted.

"You really don't recognize any them? You just shook hands with a European prince, a Saudi shiekh, three senators, two congressman, three Fortune-500 CEOs and one justice from the Fifth Circuit court of the United States!"

"This is so surreal!" I told Ted.

"No, this is a normal part of your new life, get used to it." He said.

Ted and I danced to pop, hip hop and love tunes, and he introduced me to a few of the other sissies - Valerie, Cassandra, Jill and Sally. They were friendly, except for Cassandra. She was the prettiest of the four, but, she seemed like the type that hated anyone who could compete with her.

After about four wine glasses, I had to use the ladies room.

One of the attendants pointed me in the direction - down the hall and to the right.

I found the bathroom and did my business. It was weird to piss while wearing a cock cage, but it was doable.

When I got out of the bathroom, I heard strange noises coming the opposite end of a hallway.

I heard several feet shuffling around and I heard moaning noises.

The noises seemed to come from a room down the hall, but, this part of the mansion was far from the party area.

Maybe someone had sneaked into a room to have sex. It was none of my business and I just ignored it.

But, suddenly, I heard a girl scream, "No! Stop! It hurts too much! I can't do it! Stop it!"

I just wanted to mind my own business and go back to Ted, but, I couldn't just walk away from this. Someone might be in trouble.

I heard a man yell, "Cut!" Then, he yelled "God damn it, Stella!" He said more things, it I could not hear without getting closer.

I followed the noise to a closed mohagony door of the room where all the commotion was going on.

"What's the problem? Just fucking do it! It might hurt for a while, but, you'll be fine and you'll fucking love it later!" said the man on the other side of the door.

The old wooden door had an old fashioned key hole, like you see on some movies.

I peeked through the keyhole and saw five handsome white middle aged men and a white petite cute little sissy in a room that must have been an office. They were standing around a beautiful large desk and chair. She was about my size, but a few years older, and the men towered over her. The men wore dark suits, but, they had their cocks pulled out of their pants.

My God! They were all so well-endowed!

The little sissy was dressed like a schoolgirl with a little plaid mini skirt, blouse, blue blazer, high heels and white thigh high stockings. She was pulling up her panties and the men were putting their cocks back in their pants.

She sissy had blue eyes and long blond hair. She was so pretty.

They were all facing another man on the other side of the room. It was a big office with mahogony walls and a giant fireplace.

The man on the other side of the room was pacing the room and looked upset. There were about five more guys in jeans holding lights and cameras.

They were making a movie!

The pacing man appeared to be the director. He said, "Damn it, Stella! We have got to do this scene. This is what all your your fans all over the globe have been clamoring for!

We get emails all the time asking for this.

You've done many gangbangs before why are you being so difficult to work with now?

Stella replied nearly in tears, "Joe and Larry are hung like fucking horses! It took me months to train to take a 10 inch cock balls deep. They can take turns fucking me, but, I can't take them both at the same time! I just can't!"

"We have to give your fans double penetration! They've seen your ass get pounded by monster cocks already! What they really want is your tight little sissy ass pounded mercilessly by two monster cocks!" said the director.

"They want to see hard core stuff and you've got to deliver!" He said.

"But, I can't!" Replied Stella.

The director was quiet for a couple of minutes while pacing and pondering something.

Then, he said in a harsh tone, "I should just stop it right here and cancel everything. I should just kick your ass out to the curb and blacklist you from ever working in this industry! You had nothing when I first met you!"

He paused for a minute, then softened his tone and said, "But, I'd hate to see all that we've done together these past five years go to waste, and, I have a soft spot in my heart for you. So, I'm going to make you an offer you cannot refuse, Stella. I'm going to add to your compensation package five percent royalties! You'll easily make two hundred thousand dollars within just a month of releasing this movie! And, after this movie, you don't have to do any more. You can recruit other sissies for us and train them. I'll give you 10 shares of my company and big bonuses if you recruit the right sissy!"

Stella squealed with joy and ran forward to kiss the director. They embraced and she kissed him on the lips.

"I'll do it!" Stella said.

I should have stopped spying at that point, but, I became hooked on this drama. How could Stella take to monster-sized cocks in her ass? She was as tiny as me. I couldn't believe she could even take one of them!

The guys helped Stella rub a whole bottle of lubrication on her ass.

"Okay, places people. Back to the beginning of the scene." said the director.

One guy in a suit sat in the chair behind the desk and Stella took a seat on the other side of the desk.

The four other suit guys were spread out.

"Lights, camera, action!" Yelled the director.

The man on the chair said, "Ms. Jenkins, I understand that you want to go on the highschool senior's European tour, but, cannot afford the cost."

Stella answered, "Yes, my family cannot come up with four thousand dollars, but, I want to go so bad! I would do anything to go!"

The man said, "I have reviewed your request for a travel scholarship with my colleagues on the school's finance committee. We sympathize with you, Ms. Jenkins, really, we do. But, I'm afraid there is no scholarship available for European trips."

He continued, "You know we are a very progressive private school and we gave you an academic scholarship because of your exemplary grades and because we wanted to include a transgender girl in our class body. I wish there was something we could do, but, there isn't."

Stella sat silently for a minute.

Then, she stood up, and walked to the other side of the desk where the man was sitting on the chair. She sat on the desk close to him.

"Mr. Stevenson," she said calmly. "I want to go to Europe with the girls so bad! I'm eighteen now and I'll be the only one left behind. Please, please, please sir. Help me!"

The guy playing the role of Mr. Stevenson swallowed and said, "I wish there was I way. Honestly, I do. But, there isn't!"

Stella looked around making eye contact with each of the men acting as professors.

Stella spoke again, "You all got your bonuses today. You could do a very generous thing with part of that money. Each of you could donate eight hundred dollars to my new travel scholarship. I would definitely show my appreciation."

Stella touched her lips with her finger and said, "I know you are all curious about me. Please contribute to my travel scholarship. You will feel very good about it."

The men looked around uncomfortably not knowing what to say or do.

Then, Stella put her hand on Mr. Stevenson's crotch and all the man gasped in surprise.

Mr. Stevenson grabbed her hand, as if to pull it away, but she squeezed his cock and he made a moaning sound.

All the men stood frozen as Stella got down on her knees and pulled Mr. Steven's cock out from his pants. She started sucking it!

Mr. Stevenson moaned and said, "Holy shit! Fucking amazing! It's the best fucking blowjob I've ever had!"

Mr. Stevenson said, "Yes, you really should not miss that trip!" and he pulled out money from his wallet.

The other professors pulled out money from their wallets, too, or wrote checks to Stella. She counted her four thousand dollars in cash and checks.

She squealed in delight to have the money for her European trip.

The men came closer to her and, getting on her knees, she pulled out each of their cocks out and starting sucking cocks while jerking them off with her hands.

She had to open her mouth really wide, because, she had a small mouth and the cocks were enormous.

She was able to deep throat them, though she couldn't swallow them all the way.

The men moaned and grunted in a chorus of ecstacy.

I felt myself getting very wet watching this. The cage was begining to feel small with my stiffening cock.

Then, the guys picked her up and laid her face down on the desk, with her ass at the edge of the desk, so they could take turns fucking her from behind.

They pulled on her hair, grabbed her by the throat, and pounded relentlessly, as if determined to get every penny worth of their $800 contributions to her "travel scholarship".

Her little ass was getting impaled and jackhammered by cocks that were huge enough to fuck cattle!

She screamed and arched her back! Her tight little sissy body jumped every time a cock sunk balls deep inside her.

"She is so damn small and tight!" One of the guys said.

This was brutal to watch, and yet, I felt myself getting very wet.

Then, one guy, with his cock buried balls deep inside her, grabbed her from behind and picked her up.

There was terror in her face. It was time for her to face the worst part of it all.

Another guy darted over to her and grabbed her from the front.

She closed her eyes in fear.

With one guys cock still balls deep inside her, the other guy in front of her aimed his cock at her hole, and, started to push it in.

Stella's face showed signs of excruciating pain, but, she held back tears and screams.

Then, having managed to squeeze his tip in, the man in front of her thrusted hard pushing his cock balls deep into her.