Sweet Baby 02

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Timmy's shemale parent begins Timmy's transformation.
2.7k words
4.66
14.8k
24

Part 2 of the 10 part series

Updated 06/15/2023
Created 09/10/2022
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Sweet Baby

Born to be a Porn Princess!

by Mistress Tawny Suede

Chapter Two - Beginnings

I found it almost impossible to pay attention at school the next day. When I got up in the morning, I had peeked in on mom and she had been soundly asleep.

Over dinner at home with mom, there was no sign that she thought anything unusual had gone on last night after she had left. She didn't ask any questions, nor did she seem to be waiting for me to ask her any questions. It was like, you know, she had done what she promised and we were never going to talk about it.

She left for work at the usual time and after that I could barely wait for eight o'clock to come. I was nervous, and excited. What exactly was going to happen when Roger arrived? I lay down on my bed and pulled my trousers and underwear down and slowly jerked my cock as I relived those moments with Aunt Jennifer... no MOMMY Jennifer the previous evening. I also reached up under my shirt and teased my nipples. They had always been sensitive and twirling them always gave me a sensual thrill!

Roger rang the doorbell right at eight o'clock. "Get your jacket kid, we are going for a drive." he told me. But first he brought in a hard sided case which he slid under the bed in my bedroom.

"What's that?" I asked.

"I'll tell you more about that when we get back!"

We drove for about fifteen minutes and pulled into a small suburban strip mall. All of the shops looked run down. Roger took me up to the door of a beauty salon that looked to be closed, but when he pushed the door it opened. The lighting inside was turned down low, but sitting inside were two women. Roger introduced me to Vivian Wynwood who was a matronly woman I would place in her mid-fifties who had bluish permed hair and weird looking spectacles. The other woman was a young girl not much older than me. Vivian said that Claire was her trainee.

Roger told me that I was to allow Vivian and Claire to do what they wished with me. Mommy Jennifer had given them specific instructions about my appearance. I was a bit nervous as I began to take off my clothes, as Vivian instructed. Roger used a remote control to turn on a tv set in the corner. As I stepped into a shower stall at the back of the shop I heard a basketball game on the tv.

Claire handed me a bottle of some kind of lotion and told me to spread it all over my body. Five minutes later, the small amount of body hair that I had had was all gone. Over the next ninety minutes, Vivian and Claire worked on my hair and my eyebrows. They spread moisturizers over my face and body. Vivian used a small gun to pierce my ears and put tiny studs into the two holes in each ear and she then she showed me how to clean them properly. She even used some other implement to stab my lips in a couple of places.

When they were finished I looked at the results in the large mirror that spread almost completely across one wall. I had never been a very manly boy... well, man since I was now over eighteen... but my hair was now styled much more femininely. My eyebrows had been tweezed and thinned and my lips were a different shape, again suggesting those of a girl.

"What do you think" asked Vivian.

"I, uh... ummm,," I stuttered.

"Not you dearie!" said Vivian

"Jennifer will be pleased, Mistress Vivian. Very nice!" said Roger to whom the question had been directed.

"I think he looks adorable, for a first session!" said Claire, standing on her tiptoes and giving me a light kiss on the cheek. Claire was a tiny girl, just under five feet tall. She had barely any bust and was almost rail thin, but her face was absolutely adorable. I wouldn't have minded asking her out on a date some evening if we were given a chance to be alone for a few minutes. But that was not to be.

"Lift your head up a bit, sweetie" said Vivian. I did so and she applied a very light coat of a lipstick and then handed me the tube. Looking in the mirror the colour was barely noticeable, but I did like the way that my lips seemed to shine a bit in the light.

"Thanks Mistress" said Roger. "We'll be back tomorrow night at the same time!"

As we drove back to my house, I found myself licking my lips, constantly tasting the lipstick. It was a strange sensation. I also pulled out my phone and used the reverse camera to admire my face, including pushing my hair back to admire the studs in my ears.

"You look very cute, Baby." said Roger, squeezing my hand. I grasped his and we actually held hands for the last five minutes of the drive. What had made me want to do that?

When we got home I unlocked the door and Roger followed me in. I ran upstairs to my mother's room where she had a full length mirror. I admired my new look as I turned and twisted to see myself from all sides. It was only my face and hair that looked different but I had to admit that Roger was right, I looked cute!

Roger called me and I found him in my room. The case he had put under my bed was now open. There were a few other things in it, but he had removed a brand new laptop computer and placed it on my student desk. As he started it up he told me to sit and I did. When it was ready he leaned over me and tapped a few keys. A video messaging software opened up and he hit a key to call Mommy Jennifer. Shortly her face appeared, and I could see my own face in the top right corner, the image of me that she was seeing.

"Oh baby! You look wonderful!" Mommy Jennifer squealed!

"Thank you Mommy!" I grinned and preened for her.

"Were you a good boy for Roger?" I nodded that I had been. "Good," she said. "This computer is a gift from me to you. We can talk on here anytime you wish. Just make sure that when you are done you put it back in the case, and lock it and put it back under your bed! Can you do that?"

"Yes Mommy"

"Good baby! Also on the desktop screen you will find links to a few websites that I'd like you to explore, including my own. I don't want to shock you, but they are a bit naughty! If you decide that you want to wank off while watching me on the screen, I'll take that as a compliment!" she giggled.

I just smiled at her. While she was talking I was aware of Roger standing behind me, gently rubbing my shoulders.

"Now as I said last night, if you want to come and live with me, you need to prove that you really want this. You have to prove that you will fit in. Part of that, is that you have to do whatever I tell you, and by extension, you have to do whatever Roger tells you to do as well, while you are in training!" Mommy Jennifer tried to look a bit stern, but to me she just looked... sexy!

"Oh yes Mommy, I will. I'll do whatever you want!

"That's good, sweet baby! Now go over to the case on the bed and open the red package."

I got up and did so. As I tried to open the package carefully it suddenly burst open and a dozen pair of girl's panties in all different colours, spilled out onto the bed!

"I think the pale blue pair this evening! Take off all of your clothes and put on the pale blue panties, then come back and stand in front of the screen." she told me.

I was a bit shy about taking off my clothes in front of Roger, but I did so much want to please Mommy Jennifer so I did so. The panties felt so nice as I pulled them up my smooth hairless legs! I pulled them up to my waist, but they did not fit well for a very obvious reason.

As I stood in front of the computer Mommy Jennifer smiled widely. In the corner of the screen I could see what she saw - pretty much just my panties and upper legs, but with my cock very rigid in the panties, and a precum stain spreading from where my peehole touched the fabric.

"Well, someone likes their new panties, don't they!"

"Yes, Mommy Jennifer, they feel very nice!"

"Well from now on you only wear panties under your clothes. I want you to put your boy underwear in a bag and Roger will take them away! Daytime and night time, you now just wear cute panties!"

"Yes Mommy Jennifer!" I demurred as I sat down.

"That's all I have time for tonight, sweetie! I have an appointment in a few minutes. A nice man is coming by shortly to give me some money!"

So far I had just seen Mommy Jennifer's face on the screen since she had been sitting so close. But now she leaned back and I could see that she was just wearing a robe which was tied loosely. Her large breasts were now very visible and they were so beautiful. My cock strained even harder in my panties. And then Mommy pushed her chair back and stood up. As she did I could see that she was not wearing any panties and her own cock was standing tall and was moist at the tip.

"My lovely sweet baby," she said. " I wish so much I could be there with you again! This is what you do to me!" she grinned as she pointed to her hard cock, which she waggled a bit and grinned!

"I love you Mommy Jennifer!" I blurted out!

"I love you too darling. If you continue to be a good sweetie, we can be together soon and have a LOT of fun together. You want that don't you!"

"Oh yes, Mommy!" I cried out, and I almost teared up!

"Mommy has to run now, sweetie!" She leaned in to the screen and I got the most erotic shot of her large breasts and her firm penis with a string of drool dripping from it! "Now be sure to thank Roger properly for all he has done for you. He will be back again tomorrow night! Good night dear!" And, she ended the connection.

I stood up and turned to Roger. I held out my hand to shake his. "Thank you Roger." I said, "Thank you for the evening."

But Roger did not shake my hand. Instead he pulled me to him and pulled my face to his and he kissed me! Not just a gentle peck on the lips, but a full blown kiss with his tongue in my mouth. I was startled at first, but then I kissed him back and our lips were locked together for a full minute. Towards the end of that minute, he took my hand and placed it on his groin. I could feel his hard cock in his trousers!

"Unzip me!" He said. My fingers fumbled nervously with his zipper. It was difficult getting the right angle. I tugged fruitlessly. I had never undone any zipper that I was not wearing. "Don't worry about it honey," Roger grinned. "You're going to get plenty of practise at this!"

I took a step back as Roger pushed down his pants and then his undershorts. His large cock stood up stiffly. He took my hand and pulled me back in for a kiss. This time I eagerly returned it, and my hand went instantly to his cock. It was warm, thick and throbbed at my touch.

"On your knees, Baby! Kiss it!"

I knew this is what Mommy Jennifer had meant when she said I should thank Roger! I sank to my knees, steadying myself for a moment with my hands against Roger's knees. As I did Roger's penis brushed my cheek and I could feel a slime trail there. I grasped his cock and planted a kiss directly on the tip. It was moist, and very warm. I could not resist taking a taste with the tip of my tongue.

"Use this," said Roger. He had reached into my pocket and pulled out the lipstick tube that Vivian had given me. I first pursed my lips to dry any precum off of them, then I applied a coat of lipstick. I smiled up at Roger. "Beautiful!" he said.

"Keep looking me in the eyes, Baby! Now open your mouth. No, keep looking at my eyes, not my cock!"

I did as I was told. He could see the delight in my eyes as he slid his cock past my lips. My rouged lips closed on his shaft and I sucked on my first cock. There were only two inches in my mouth but it felt wonderful! I wanted Mommy Jennifer to be proud of me!

I used my hand to grasp Roger's cock and I began to bob my head on it. I had watched many porn videos and watched girls give blowjobs to guys. Of course, I had always imagined that it was some girl sucking on my cock!

But now I had a nice firm dick in my mouth. A dick that was attached to a very attractive man!

Did I just say that a MAN was attractive? Hmmmmmmm....

Roger's cock hit the back of my throat. There was still so much of it that I had not sucked! When he pulled out, the drool I left behind was faintly coloured by my lipstick. I smiled at that. MY lipstick!

At first Roger was passive. He let me explore his cock with my lips and my hands. Occasionally my eyes would leave his and I would admire his beautiful rod, but he would take his finger and lift my chin so that I was looking in his eyes again. He would just smile, then push his cock deeper.

I sucked on his cock for about ten minutes. Every once in awhile Roger would shift position slightly, as if he wanted to get a better look in a mirror, or was concerned about angles for some reason.

But then his breathing got deeper and stronger. My hands on his legs could feel his muscles tighten. From my own masturbating I knew this meant he was close to cumming. Roger grasped my head and began to thrust more rapidly and firmly. Instead of me sucking him, he was now fucking my mouth!

It was only a minute, but it was a minute that began to scare me! He was forceful and began to hurt me! I gagged repeatedly as he hit the back of my throat. He did not attempt to go further, but the lack of penetration seemed to frustrate him and his speed increased even more!

Then... then... he grunted... he paused.. Then he pushed in to the very back and he suddenly shot a rope of cum into my mouth. Then a second and a third!. I barely tasted them before I had to swallow! And swallow again.

Then he pulled out of my mouth and the last two sprays of cum fell across my face! My left nostril was clogged and my left ear was slick with his scum!

Roger sat back on my bed. I remained on my knees and looked up at him, saying "Thank you, Roger!" He grinned.

Roger left five minutes later, giving me a hug and a kiss at the door. My own cock was straining in my blue panties and the entire front was transparent from my own wet secretions.

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petey377petey377over 1 year ago

lucky boi can't wait to find out what else mommy has in store for him! your stories are so HOT

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READ MORE OF THIS SERIES

Sweet Baby 01 Previous Part
Sweet Baby Series Info

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