Sissified Ch. 20

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Roxie starts a new career.
2.5k words
4.53
21.7k
19

Part 20 of the 20 part series

Updated 06/10/2023
Created 06/01/2021
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This is the twentieth story in the series, please read the previous chapters so as to understand the story better.

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"Mom what's happening?" I asked.

"Don't you like your gift, sweetie?" mom replied.

I looked at the huge E-cup tits my mother had gifted me. I got up and squeezed them to make sure they were real. They were so soft and the nipples were much more sensitive. I got up from the bed and went to the mirror, the boobs did suit my body. I looked at myself from different angles and was satisfied with how they made me look sexier.

"I love them mommy." I screamed.

"I knew you would like them." Mom replied.

"This is the best gift ever." I said.

"I know sweetie, you like them so much you didn't even see the other changes." Mom replied.

"What are you talking about?" I asked and turned towards the mirror.

I looked at my face, it looked different. It looked more feminine and the lips were plumper. I looked hot now. I was so aroused when I saw how sexy I looked my clitty leaked a little. My mom noticed it.

"Guess you like the facial smoothening and the lips." She said smiling.

"Yes, mommy."

"Great. You rest now, we have a flight back home tomorrow and then we will be shifting to L.A." mom said and left.

I went to sleep feeling empty without my plug, they weren't allowed at the hospital. I managed to sleep. The next day I was discharged. Mom and mistress had already gotten me loads of lingerie and clothes for my new size. They dressed me up in a pink bikini panty and a deep cut short backless summer dress. My breasts were so huge and felt so heavy, the dress didn't support it much.

"Mom my breasts are heavy can't I wear a bra?" I asked.

"Welcome to our world, now you know how difficult it is for us?", mom asked smiling.

"I get it mom, but I really need a bra and the dress barely covers them." I replied.

"Sweetie it's a backless dress, a bra won't look good with it, and as for your breasts you need to get used to them." Mistress replied

"Ok, mistress." I replied.

We went to airport and got on our plane. Mom and mistress were sitting couple of seats infront of me and I was alone and a seat was empty near me. I was relieved to know I would be alone. As the plane was about to close boarding, a man came running in and got into the seat next to me. he was around 6"5', brown hair and so handsome.

After some time, I noticed he was staring at me. I looked at him.

"Hey didn't mean to stare, I'm Dave. I just thought you are really pretty." He said smiling.

"Well, thank you. I'm Roxie." I replied.

"So, Roxie, are you returning?"

"Yes, I just graduated and I came for a trip with my family."

"Oh, that's great. Well, I'm a lawyer and I live in L.A., I came here for a vacation."

"My mom's moving to L.A. and I'm going with her."

"That's great." He replied.

Just then there was a huge turbulence and my boobs slid out of the dresses and were completely exposed. Dave tried to not stare at them, I quickly fixed it.

"Sorry." I said as I saw a huge boner grow in his pants.

I liked the effect my new boobs had on men, looking at his boner I leaked a little. We talked for a while and then I nodded off. I woke you and saw Dave staring at my tits. I went near him and whispered in his ears.

"Do you want to feel them?' I asked

He looked around to check and every one was sleeping it was almost 11 pm now. He didn't reply. I grabbed his hand and put them on my boobs, he felt them and started squeezing them and playing with the nipples, it felt so good. We kissed for a long time while exploring each other. He asked me to follow him into the lavatory. We went inside without anyone noticing. We stripped and I got down to sucking his huge 8-inch cock.

"I want you to use your boobs. Give me a boob job." Dave said

This was my first time giving a boob job. I placed his dick in between my boobs and started squeezing, I moved them up and down and I could feel Dave liked it.

"They are so soft and feel great." Dave complimented.

He picked up and removed my panties.

"What's this you have been hiding?" he said looking at my clitty.

Before I could reply he grabbed it and gave it a slap.

"You like it sissy."

"Yes, master." I replied.

"Call me daddy." He said.

"Yes, daddy."

"Good girl. Now ask daddy to fuck your pretty pussy."

"Daddy, please fuck my pussy with your huge dick." I said seductively.

"Beg for it sissy."

"Daddy please fill me with your dick, I really need it. Please play with my boobs while you do it." I said.

"I can't say no to that." He said and picked me up again and pulled my plug out and pushed his dick in my pussy. It went deep and hit my G-spot. He continued ramming his dick, after sometime he came inside me and all the excitement made my legs shiver and I had a strong orgasm. He quickly pushed the plug inside to prevent his cum from getting out, we cleaned and went back to our seats my legs still shivering.

We slept and the next morning as we were about to land, he kissed me and gave me his card. We got off the plane and went to the bathroom. Mom and mistress were waiting at the exit when I saw them. I went closer and saw Dave talking to Mom.

"Hey, Roxie." Dave said as he saw me.

"You know my daughter?" mom asked.

"Yes, she was sitting next to me in the plane. Such is such fun to travel with." Dave replied.

"Yes, I know what you mean." Mom replied.

"Anyway, see you all later." Dave said and left.

"Mom how do you know Dave?" I asked.

"Well, he is my boss." Mom replied.

"Really?"

"Yes."

"OK." I replied.

I was excited I could meet him when I'm in L.A., I was happy. We went back to our house and got ready for moving. It was soon the day we were leaving. I was dressed in a tank top and a denim short with sneakers, my boobs felt like they might fall out anytime. Mistress came to meet us.

"I'll be missing you, Robin." Mom said.

"I will miss you both too." She replied hugging her.

She came to me and hugged me tightly.

"I'll miss you a lot sweetie, be a good sissy." She said.

"I will mistress." I replied.

"Good girl."

"So, your audition is on Saturday for the movie, Paul will call you with the details." Mistress said.

"Ok mistress."

"I would be like a dream come true if you come with us." Mom said to mistress.

"Well, I have been thinking about it. I received an offer from a university in L.A., and I might take it." Mistress replied.

"Really, its so great. When are you moving?"

"Next month."

"Great I will look forward to it."

Everything was packed and we were set to leave. Mom said goodbye to mistress and got in the car. I kneeled down infront of her and kissed her shoes, I looked up and said goodbye. I could see tears in her eyes.

"I have taught you well." She said crying.

"Thank you for everything, mistress." I said.

"You're welcome sweetie." She replied.

I got in the car and mom started driving.

When I woke up, we were in a really good neighbourhood with large villas, mom stopped infront of a huge building with two floors, the house was huge with a pool, garden everything. I excitedly got out and hurried into the house.

"The whole house is ours?" I asked mom.

"Yes, sweetie. Let me show you your room." Mom replied.

I went with her. The room was huge almost 4 times my previous room, it had a dresser and it was already filled with pretty clothes and lingerie and swimwear. There was a huge dressing table and the bathroom was big and had everything. I went back to the room with mom and noticed a pink door inside my room that mom hadn't shown me yet.

"What's there, mom?" I asked

"It's the best room, let me show." Mom replied.

She asked me to open the door and go inside. The room was filled with all kinds of toys; a fuck machine with variety of dildos, vibrators and dildoes of different shapes and sizes, vibrators and everything else.

"Do you like it?" mom asked.

"I love it. You're the best mom ever." I shouted excitedly.

"Oh, sweetie. You are such a good girl." She replied and hugged me.

We settled down quickly in the house. Before I knew it was Saturday. Paul had already called and told me the location of the meeting. I got up and got into my maid uniform and did the chores and got breakfast ready for mom. Mom came down in her sheer nightie and had breakfast.

"Good as always." Mom complimented.

"Thank you, mom." I replied.

"So, excited for the interview?" mom inquired.

"A little bit." I replied.

"Don't worry you will do great." Mom assured me.

I got dressed in a black lacy bra and panty with a short sundress and a pair of heels, I did my makeup and got ready to leave. Mom dropped me off at the location it was a big building. I went into the building and asked for Paul and the receptionist gave directions to his office. I knocked on his door and he opened quickly. I got in to see two people sitting.

"Roxie, this is our producer and the director and they will be doing the interview." Paul said.

I introduced myself, their names were Chris and Jack.

"Now would you please undress, so we can go on with the interview." Chris said.

I looked at Paul and he nodded. I got out of my dress.

"You have a great figure, could you turn around please." Jack said.

I turned around, Chris moved towards me grabbed my bubble butts and squeezed them and spanked them.

"They feel and look great." He said. He slid my panties out and grabbed my clitty and jerked it a little with two fingers, I leaked a little.

"Sorry, it doesn't get hard anymore." I said meekly.

"Oh, is it so. Its better this way." He replied.

Jack got off his seat and grabbed my boobs and gave them a squeeze and played with my nipples.

"These look great too." He complimented.

I was completely naked now with two men feeling me. it got me a little excited and made me leak.

Jack scooped my juice and fed it to me, I licked it from his fingers.

"So, why don't you show us your skills." Jack said.

They removed their pants and I got down to my knees and grabbed their cocks. I jerked them a little and started sucking on Jack's cock while giving a hand job to Chris. After a while I turned to Chris's dick and gave it a good deepthroat. I got on my fours and Chris pushed his cock into my pussy while I still had Jack's cock in my mouth. they continued this for while and changed their positions.

Finally, Chris came in my pussy while Jack came deep into my throat.

"You have a great career in this industry." Jack said.

"Thank you, sir." I replied breathlessly exhausted from the interview.

Paul guided me out and mom was waiting for me outside. I got into the car and she smiled at me.

"Today's your lucky day sweetie." Mom said smiling.

"Why mom?"

"Well, I had a call from Dave and he told me all about you and what you did in the plane."

"Mom, I can explain."

"I understand sweetie, you liked him and slept with him that really isn't a problem. In-fact Dave liked you so much he wants me to make you, my secretary." Mom said.

"Mom, you're making me your secretary?" I asked.

"Yes, I don't have much choice." Mom replied.

"But, mom what about the interview I just had?"

"Don't worry about it, you can do both."

"Ok mom."

Mom took me shopping for office clothes as I would be starting the next day.

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Almost a year had passed since I had moved to L.A., my life was so different now, morning I would wake up to do my maid duties, it was so much work. Now that Mistress had moved in the top floor of the house, I had to clean both the houses, we had breakfast together, then mistress would leave for her job at the university and I would change into my formal clothes, which consists of tight blouses and shirts and tops and mini formal skirt with full set of lingerie including garter belt and stockings. Completed with really high heels. I would leave with mom and do my job as her secretary. Sometimes Dave me ask to come to his office and he would fuck my tight pussy. Mom occasionally uses me to get deals for her company, she would offer me to the clients and after I had my time with them, they would always agree to the deals. I had to go to my shoots after office. I had become pretty popular, and had a lot of views and made a lot of money. Mistress and mom played and trained me daily, I would both lick their pussy and kiss their feet goodnight. My life had changed so much since the time Mistress caught me masturbating to sissy porn. I look at my big boobs, my slim waist, the juicy bubble butt, toned and hairless body, with the perfect pretty face and the long blonde hair. I looked so much better than when I pretended to be a small dicked boy. After a long tiring day, I went to my room and stripped and got into the bath tub. I looked down at my clitty, it was just the head poking out and my had gotten so small they weren't even noticeable. I looked at it and thought about the changes in my life. I got out of the bath and went to the pink room and started the fucking machine and laid down on my back. I selected the largest dildo and pushed it inside and started it, It pounded my sissy pussy and made my clit leak a lot, finally I squirted all over my belly, I closed my eyes and thought about the days to come.

THE END.

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AnonymousAnonymous2 months ago

great story wish some one did this to me when young sounds great life RB

AnonymousAnonymous4 months ago

Very good story

All the characters are significant and Ron/Roxie embodies perfectly the journey of dreams

of a cute girly boy living with respect enthusiasm devotion and pleasure all the paths of a marvellous

and complete sissification. Ron was born to be Roxie.

Great bravo to the author

AnonymousAnonymousabout 1 year ago

Please continue the series don’t stop

AnonymousAnonymousover 1 year ago

Please write more add nipple clamp and lot of boob play

Monalott69Monalott69over 1 year ago

This is a great story, I could not stop reading it. Your are a awesome writer and will follow you to read more of your stories.

Thanks Mona

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Sissified Ch. 19 Previous Part
Sissified Series Info

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