Sissified Ch. 19

This is the nineteenth story in the series, please read the previous chapters so as to understand the story better.

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I felt a sigh a relief when I saw my house. I tried walking as fast as I could without slipping my buttplug out of my loose cum dripping sissy pussy, my sissy clit was covered in dried cum and my panties were missing, it was January and I could feel the cold wind shrinking my sissy clit even more under my micro skirt. My whole body, face, hair and clothes everything was covered with cum. I rushed inside my house and quickly dropped the clothes into laundry and got into the shower and washed the cum off my, I slowly let my butt plug out and let the huge amount of cum flow out of my pussy. It was my last day at school before I graduated, finally the hellish month were coming to an end. My life was really hard inside school. As soon as mom dropped me off at school, I proceeded to the gym, where Jamal and his buddies would make me suck their sweaty cocks after their morning workouts, or if they are in the mood, they cream pie in my ass and let me sit through the class with a leaking ass. During the school hours I would have to serve multiple boys and girls throughout the day, sometimes even the principal wanted to spend some time with me. Mistress would give me punishments to stay after school and help in clean ups and the janitors would often try their luck with me and all of them did get lucky with me, I could proudly say I have seen every cock at my school, but finally the days were over, tomorrow was the graduation ceremony, probably the last time I see my school.

I got out of my bath and cooked dinner for mom. She showed up really late with a huge carton.

"What is it mom?" I asked.

"It's your outfit for tomorrow for the graduation party, Robin is the Chaperone. She reminded me of it and I got a beautiful outfit for you. By the way you don't have to go the graduation ceremony tomorrow, Robin would collect your certificate. You have to get ready for the party." Mom replied.

"But mom do I really need to go to this party?"

"Yes, sweetie. I already bought you a dress."

"OK, mom."

The following morning, we went to the salon and got some facials, manicures, pedicures, face treatments and applied some sexy make-up. Mom dressed me up in a red satin panty in which my clitty snugly fit, without any bulge, next I put on a purple long dress with slit up to my waist, I added a pair of red high heels. I looked at myself at the mirror and was amazed to see the beautiful girl looking back at me.

"You look so pretty. My beautiful daughter all grown up." Mom said with tears welling up.

"I will always be your little girl mommy." I said and hugged her.

Mom drove me to the school and I went to the gym which was the party location, no adult was present except for mistress as she was the chaperone. I went inside and looked around couples dancing and snuggling in the corners, single boys sitting hopelessly looking for girls for their last high school dance. Studs sitting together joking and getting drunk. I didn't fit anywhere. I went to grab a drink. I suddenly felt a poke on my shoulder. I turned around to see a handsome man, tall and muscular with blond hair and blue eyes looking at me.

"Hi, I'm Sam. I haven't seen you before." He said.

"I'm Roxie. I just came back to school for a month." I replied.

We continued chatting for some time. He had joined the school after I had left, he was such a sweet person. We talked a lot about school and our lives. I really liked him. He was going to Harvard and would be moving the next day. We continued talking. Suddenly he got up and grabbed my arm.

"Let's dance." He said.

I nodded and followed. It was a romantic song. He grabbed my waist and pulled me close, we started dancing. I could smell him, he smelt so good. His breath felt so good on my neck. His face slowly came close and we kissed, our tongues met, it was a deep long kiss. We decided to ditch the party and leave. We decided to go to his house. His room was so huge. He wasted no time. he started kissing me and undressed. I followed and got naked.

"That's a surprise." He said looking at my clitty.

"Is that a problem?" I asked.

"No, but I thought you were a girl."

I moved closer and grabbed his dick and started jerking it slowly.

"You want me to leave?" I asked.

"No." he said silently.

I went down and licked his balls and his shaft and slowly started sucking his 9-inch cock. He got rock hard. I started giving him deep throats. All this excited me and made my clitty leak with precum. I looked up at his face. I could see he was already in heavens. I got up and grabbed his dick and pulled him to the bed. I assumed the doggy position, with my ass high up. He jumped onto the bed and slowly started fucking my pussy. We changed positions and continued fucking for a long time. Finally, I fell asleep in his arms.

I woke up early next morning, Sam got up and drove me home. We kissed for the last time and he left. I went inside my house and got ready for the day. Mom came down for her breakfast.

"You had fun yesterday?" mom asked.

"Yes, mom. I met this amazing guy." I said and talked about my night.

"First love, such a beautiful thing, it's a shame he is moving." Mom replied.

"Yes, mom."

"Sweetie, I have something to cheer you up." Mom said.

"What is it mom?" I asked.

"It was supposed to be your graduation gift. It's a trip to Hawaii. You, me and Robin."

"Thank you so much, mommy."

"Anything for my cutie."

We hugged. Mom had said she would be packing my luggage. So, I just waited for the next day for my trip. Next day mistress had arranged a cab for us to the airport. Mom had picked a short floral skirt and a pair of heels for me. I slid on my panties and my bra to support my budding B-cup boobs. I put on my outfit and met mom downstairs. She was looking stunning in her denim shorts and white sleeveless top. We got into the cab and reached the airport where we met Ms. Robin, she was in a red top and a pair of shorts. We greeted her and then went into the airport. We went through security and waited at the lounge.

"Thank you, for the surprise. I'm so excited." I said.

"Oh, don't mention it honey." Mom replied.

"This is only the beginning I have a wonderful month-long trip planned at Hawaii." Ms. Robin replied.

"Month?" I asked.

"Yes, I forgot to mention. I just got a promotion and will be moving to L.A. soon. The raise came with a hefty raise as now I'm the head of the whole L.A. division." Mom said.

"Wow, mom I'm so happy for you." I said.

"Yes, sweetie. We will have an amazing life there." Mom replied smiling.

"What do you mean by we? I am going to college." I asked.

"Well, that's not possible. You managed to complete school, but with such low marks its impossible for you to get into any college." Ms. Robin replied.

"I can't go to college?" I asked as tears welled up in my eyes.

"Don't worry sweetie, you will have a lot of careers after we return from Hawaii." Mom said hugging me.

I stopped crying as we heard the boarding call for our flight. We sat in the plane. Slowly I drifted to sleep. I woke up as we were about to land. We collected our luggage and went to the resort. It was an expensive one. I spotted a couple of celebrities at the resort. I was so excited; I was going to be staying at the same place as them. We went to our rooms and changed into bathing suits. Mom had packed a pink minikini for me. I was embarrassed to wear it. But once I looked in the mirror my thoughts changed, I had become such a beautiful girl, my bulge wasn't even visible anymore. I proudly wanted to show the body I had. I went down to the pool and met Ms. Robin and mom.

"You look amazing in it." mom said.

"Thank you, mommy." I replied.

"Come here, let me rub sun lotion on you. A nice tan would look good on you." Ms. Robin said.

I went to her and she rubbed lotion on me, she covered every inch and even made me remove my bra in public. I quickly slept face down to cover my boobs, no one except me was topless. After 30 mins Ms. Robin asked me to turn around to tan my front side. I slowly turned realising every eye turning along them, all of them went straight to my breasts. I felt exposed but somehow all this turned me on even more and I could feel myself leaking.

"Roxie, I want you to be ready tonight, there is someone special I want you to meet. He will be picking you up. Be sure to give him a good time." Ms. Robin said and smacked me on my ass.

"Yes, mistress." I replied.

We went back to our rooms. I started preparing for my date, I went to the bath and saw my beautiful tanned body with perfect tan lines. I bathed, washed my hair and gave myself an enema. I put my plug back inside and did my make up. I put on a pair of red satin panties and put on a red backless cocktail dress. I put on matching necklace and ear rings, and finally the hells the match the look. I waited in my room, around 8 the bell rang. I opened the door. He was around 195cm, fair and had brown hair. He was wearing an expensive suit. He looked amazing.

"Roxie?" he asked.

"Yes."

"I'm Paul. Nice to meet you." He said and kissed my hand.

We went to his private cabin at the resort. There he had a table set up for us.

"Well Roxie, I must say you are really beautiful." Paul said.

"Thank you. You are quite handsome too." I replied.

"Thank you." He replied.

We continued our dinner. I slowly touched his feet with my toes and made my way to his dick. I could feel his huge dick growing with every stroke.

"Roxie, do you really need it that bad?" Paul asked.

"Yes, please." I replied leaking in my panties.

He picked me up and went to the bed. There he asked me to take his cock out. It was so huge around 9-inches, nothing I couldn't handle, I started sucking and pretty sure I gave him the best blowjob of his life. He asked me to stop and lie on the bed, he slowly put his dick inside and started fucking me, his huge cock grinded against my prostate and I leaked like crazy. Finally, he came inside me, and I squirted from the excitement. He thanked me for the fun and said good bye. I left the room and came back to my own. Exhausted from all the sex I fell asleep quickly. Next morning when I met mom and Ms. Robin they were really excited.

"Seems you had a really good night." Mom said smiling.

"Yes, mom. Paul was so big." I replied.

"Well, you will be happy to know that Paul is a casting director and he really liked you." Ms. Robin said.

"Casting director, like in the movies?" I asked.

"Yes, honey. But Paul deals with specific type of movies. You will find out later." Mom said.

"Anyway, today I will be giving you your graduation gift." Ms. Robin said.

"Thank you. What is it?" I asked.

"Patience sweetie, you will know soon." Ms. Robin replied.

After the breakfast we went to huge hospital. It was a world famous, plastic surgery hospital. We went inside and met the doctor. He was a young man around 30, handsome.

"Roxie, so nice to finally meet you." He said shaking my hand.

"Nice to meet you." I replied.

"You are really pretty, but I can see you getting even better." he said.

I was confused why was I here for. I looked at mom. She smiled at me.

"That is the reason why we are here for Dr. Zakir." Ms. Robin said.

"Yes, I really want to start the procedure." He said.

"We can start now, if you are ready." Ms. Robin said.

"Great." He said and went inside to get ready.

"Mom what is going on?" I asked.

"Don't worry sweetie. Trust me and go inside." She replied.

I went inside, I was stripped and given a hospital gown and asked to lie down. They gave me an injection and I slowly drifted into sleep.

Slowly I opened my eyes, Mom was sitting next to me, reading a book. I called her.

"Sweetie you are awake. You have been out for 2 weeks. You are doing great." She said.

"Mom what happened?" I asked while getting up.

I felt something heavy on my chest, I looked down to see a pair of huge E-cup boobs.

To be continued.........................