Sissified Ch. 09

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

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I was woken up at 4:30 in the morning by a vibration inside me, I hit right on my prostate and made me leak a bit, I pulled the vibrator out and got to my chores, cleaning, washing and cooking. Ms. Robin came down in her nightie to have breakfast, it was a black transparent nightie, she was beautiful. She took a bite and gave me smile.

"We will leave at 10 do your training by then, you have a photoshoot today." she reminded me.

I nodded. I cleaned up the table and went to my room to get dressed. Ms. Robin had already told me what to wear, I wore a matching red silk pair of bra and panty with little bow on them, wore a matching garter belt and pantyhose. On top of these I put on short business skirt and a button-down shirt. I had to look professional today. I looked in the mirror, I looked different I normally wore provocative slutty outfits but these were different, I felt like a lady for the first time. I applied makeup and went out. Ms. Robin drove me to the mall. I went into the mall alone and met Janet, we drove to a studio.

"He is the photographer, lets meet him." Janet said.

"Hello, Dave." Janet said to him.

"Hey, Janet." he replied, he wasn't old, around 30, I think. He was Caucasian with an athletic built, he was handsome I thought.

"Are you the model?" he asked me.

"Yes." I replied meekly.

"He is Ron, he will be doing the new line of lingerie for well sissies." Janet explained.

"Ok, he looks so pretty I would have never guessed he was a boy." Dave said.

I blushed.

"Get changed and meet me in the shoot area." Dave said.

I followed Janet into the dressing room, the was make-up artist waiting. She redid my make up from the scratch, it looked so good, she even trimmed my eyebrows and styled my hair. My hair was quite long now, all the pills I took had shown the effect. When she was done, I looked completely different my eyebrows were trimmed and looked feminine, my hair was completely straight and curly at just the ends reminded me of scarlet Johansson. Next, I stripped and changed into the new lingerie. First one was a white set of bridal bra and panties with a white garter which I wore on one thigh, she put a veil on my head, the panty had a hole for my asshole and little space for my cage. I went out. Every crew member stared at me, I knew I looked beautiful, I swayed my hips with every step.

"Perfect!" Dave exclaimed.

I smiled.

"Now, give me a good pose."

I sat on the chair with my legs crossed like a lady and moved one of my hands up to a curve.

"Beautiful!" he shouted.

Next, I leaned against the wall with my feet together and my hands forming a heart over me. then I moved to bed and lied on my back gave a sexy pose. This continued for a while. Then I changed into a new pair of clothes, they were a pair of blue and white bikinis, this panty also had a hole for my asshole and space for my cage. I posed in them too. It was around 6 the photoshoot got over. I prepared to leave.

"Do you like Dave?" Janet asked.

"No, nothing like that. I mean he is handsome." I said.

"Oh cutie, you like him you first boy crush. Say what I will help you he is still in his room, now change into these." she said and handed me the bridal lingerie.

I got dressed, I was excited I wanted to know If I could get someone as handsome as Dave. I knocked at his door.

"Come in." he said.

I went in, he was shocked to see me all dressed up.

"What's up Ron?" he asked.

"Just wanted to meet you before I leave," I said biting my lower lip.

He looked at me.

"Do I look good in these?"

"You look stunning, if I may say even more beautiful than a real girl."

I pretended to drop something and bent over giving him a complete view of my ass and the butt plug. I saw him staring.

"Do you like it?" I asked sluttily.

He didn't reply.

"Go on touch them if you want." I said. He didn't move.

"I knew I didn't look good. Why did you lie?" I said with a hint of anger.

"No, you look beautiful, it's just that...."

Before he could finish, I grabbed his hand and put it in my ass, he fondled them and gave them a squeeze.

"Like them?" I asked.

He replied by smacking them. I moaned, he put his other hand on my ass and squeezed them, he played with them for a while the he leaned forward and kissed me, I didn't resist It was my first time kissing anyone, our tongues intertwined his hands moves up and removed my bra, he cupped my A cup boobs and squeezed them, played with my hard nipples and gave them a pinch. We stopped kissing and I got on my knees. I unzipped him his dick fell out. It was quite large around 8-iches in length it was already rock hard. I moved my hand up and down the shaft, I kissed the tip. Precum flowed out I licked it up, I tasted so good, I fondled his balls and sucked them while jerking him, then I placed my lips on the head and sucked, deeper and deeper I went every time, in no time he was balls deep in my mouth, I used my tongue to lick around his cock.

His eyes were shut, he was in so much pleasure. He looked down on me, I kept sucking him.

"You are so good." he said. I didn't reply.

After sometime his dick twitched and without any warning he came into my mouth, I gulped all his cum and then licked his clean. He was exhausted.

"Thank you for the pleasure." I said.

"Will we meet again?" he asked.

"Let's see." I said sluttily and winked, then I left the room.

I got dressed. Janet and I got in her car.

"So, how was it?" she asked.

"It was so good, I couldn't believe when I succeeded in seducing him." I replied.

"Why you are so beautiful you can seduce anyone you want."

"Thank you, mistress."

She drove to the mall, where Ms. Robin was waiting.

"I heard about your little adventure." she said.

"Here Robin." Janet said and gave Ms. Robin a pen drive.

"This is a video of you from Dave's room." Janet said.

I was confused.

"This was already planned out, I made sure you tried hitting on Dave, so I had installed a camera in his room when he was photographing you." Janet explained.

"You have become so good at it. Your training is almost complete. Now let us go home." Ms. Robin said.

We got in the car. We reached home I changed into the maid uniform and started preparing dinner. After dinner Ms. Robin got a phone call from Janet.

"I have good news, they liked your photos they have selected you to be the new line's model." she said.

I didn't know how to react. So, I just smiled.

"Your photos will be on all the billboards and all of advertisements of their stores." she explained.

I was shocked to hear, this everyone will be seeing me in those clothes, I thought.

"But mistress everyone will see me in those clothes, everyone will know. I will never be able to go back to normal." I said crying.

She pulled me to the mirror.

"Look at yourself, how do you look?" she asked.

I looked in the mirror, she was correct I was completely different, no one could possibly recognize me. I smiled at her.

"See, you look different, no one will recognize you, all they will see is a beautiful sissy. Now due to this you will be getting huge checks every month, you will clear your debt in no time, then I will help you go back to normal." she said.

"Yes, Mistress." I replied.

"Good, now they will be requiring some documents to make a contract."

"I have them at home, mistress." I replied.

"I will drive you there tomorrow, we need those." she said.

I nodded.

"I have ordered a new gift for you, it's quite expensive, it will reach any moment now." she said.

I had changed back to my T-shirt, when the bell rang. I went to the door and opened. There was a girl with a huge package beside her.

"Is this Ms. Robin's house?" she asked.

By now Ms. Robin has come to the door.

"Yes." She replied and signed the delivery.

I took the package and thanked her.

"Sissy she is a woman and how have I taught you to thanks women." Ms. Robin said.

I got on my knees and kissed her shoes. She blushed and left.

I took the package into my room, Ms. Robin followed. I opened it, there was a weird machine inside it, I took it out and assembled it. There was a small motor and a rod, the platform had 4 constraints, I didn't understand what it was, I looked at her.

"Don't you get what it is?" she asked.

"No, mistress." I replied.

"Silly it is a sex machine, I'll show you how to use it." she said.

She got me on my fours on the platform and bound my feet and hands with the constraints. I was in a dog pose locked, I couldn't move then she took a dildo and fixed it in the rod of the machine, then applied lube over it and pulled my butt-plug out. I finally understood what it was.

As she turned it on the dildo slowly pushed into my ass, it moved in a slow rhythm, it felt so good, it vibrated, and it aroused me so much when it touched my prostate.

"This is to control the speed." she said showing a remote.

I was in too much pleasure to reply.

"Glad you like it. I'll now set it to random, the speed will change randomly, I will check in on you after some time." she said.

She pushed a button and left the room. At first nothing happened it went on with a slow pace, then suddenly it increased, it kept on increasing with time, after 15 mins I was about to cum, but it suddenly stopped, I was so aroused, I prayed for it to start again, I wanted to cum. It started again with a slow pace and then it increased and slowed down again, then it got to the fastest setting, all these different patterns made be so aroused, but every time when I was just about to cum, it would slow down, it made me so frustrated.

This went on for 2 hours, by now a huge pool of precum was there below me. Ms. Robin returned.

"Look how much mess you have made, all that sissy juice. Have you squirted yet?" she asked.

"No, mistress, every time just when I'm on the edge it slows down." I replied.

"Oh, my poor sissy, I didn't know what random was, let me help you." she said and pushed a button and sat on my bed.

The speed slowly increased and kept on increasing, but this time it didn't decrease. The dildo pounded my ass, and hit my prostate every time. I started shaking, my limbs were paining, I gave into the pleasure. I came hard, the machine didn't stop I came again, the machine continued pounding me, I came again. I was exhausted by now.

"Please stop it mistress." I cried.

She looked up from her magazine, and clicked a button and the ponding stopped.

"Did you like it?" she asked.

"Yes, mistress" I replied.

"Good now clean it up and go to sleep we have to go to your house tomorrow." she said and left.

I licked my cum clean, and got into bed, and slept instantly.

I got up and finished my chores, after breakfast I went to my room and dressed up, I wore a black lacy panty and bra. I covered them with a pink crop top with "sissy" printed on it and put a micro skirt on my waist, I put on make-up and nail paint. Put on my red heels and went to meet Ms. Robin. She was ready and we went to her car and go into it. She drove to my house, dropped me.

"I have some work, you find the documents I will pick up in an hour." she said and drove away.

I went into the house, I unlocked the door and got in. so much had changed since I was last here, I realised I went to my room and got the documents, I sat on my bed.

I heard the main door open, I got out of my room to check.

"Feels good to be back here." a voice came from downstairs.

It was Mom, she was back from her trip. I hurried back to my room, as I was walking, I slipped and fell. She heard the sound.

"Who is there?" she shouted.

I didn't reply I couldn't let her see me like this.

"Ron Is that you?" she shouted again.

I kept quiet.

"Whoever it is come down or else I'm calling the police." she said.

I had to stop her from calling the police, otherwise there would be huge problem, I went down and stood before her.

"Who are you?" she asked.

I stood there with my head facing down.

"Speak or else I'm calling the cops." she said.

"Mom, its me." I said.

"Ron?" she asked with a fading voice.

To be continued...