Sweet Baby 01

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Timmy meets his shemale pornstar parent!
3.7k words
4.54
25.8k
61

Part 1 of the 10 part series

Updated 06/15/2023
Created 09/10/2022
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I have written several chapters to this story, but there are still many chapters left to be written. I hope you enjoy your first encounter with Sweet Baby. Please leave feedback as it encourages me to write more!

Sweet Baby

Born to be a Porn Princess!

by Mistress Tawny Suede

Chapter One - Introductions

"When, Mom, when?"

That was the question I had asked my mother for the last dozen years.

"When will you tell me about him? When can I meet him?"

My father had walked out on us when I was only four years old. Now, I had just turned eighteen and could not remember anything at all about him. There were no pictures of him in the apartment where my mother and I lived. Mother never ever talked about him, except to tell me to shut up whenever I brought him up.

Without a father to guide me and set examples, my life so far had been..... interesting. I was shy and introverted. I was not athletic. Yeah, I played some sports with the other kids in the schoolyard, but never signed up for any organized activities. I was short and slim, not muscular. I did try to get involved in school activities like chess club and the science club, but even there I was too shy to make any friends really.

I adored my mother. She was very beautiful and dressed to show off her assets. Yeah, I mean her tits and her legs. I know it may not seem right to talk about my mother that way, but it was true. Mom and I had an unusual relationship. She worked as a bartender downtown and so she dressed sexy to bring in the tips. She always talked about how low her actual pay was and that she had to rely on tips to make enough money. She worked five nights a week. I saw a bit more of her on Mondays and Tuesdays, but the rest of the week I barely saw her.

She was a good mother, don't get me wrong, but she knew that she had to make money for us to live on.

If I came straight home from school, we usually spent about an hour together over dinner and then she had to head out to go to work. The bar closed at 3 am and it took her close to an hour to get home, so when I got up in the morning she was still asleep in bed and I got my own breakfast. Some mornings the door to her bedroom would be open and she was not there - that meant she had hooked up with some guy for the night and gone back to his place. I didn't mind. She was always home at dinner time.

But Mom was never there to help me with my homework at night, or to listen to any problems I might have from my school day. I could have used the help, but then, how much help would she really have been? I took after my mother in that I was not overly bright. I had been held back during one year of high school. If I had had any other options for work or something, I would probably have dropped out. But being small and anti-social, I had no prospects for work. I stayed in school because I had no other options.

I took after my mom in another way too. Early on I started exploring her bedroom. The drawers, her closet, her makeup table. I think it started because I loved the smell of her perfume and the feel of her lipstick on my cheek when she leaned in to kiss me every evening when she went to work.

At first it started with me just laying on her bed and inhaling her scent from the sheets and pillow but eventually led to me smelling the clothes in her closet and exploring the scents of the various cosmetics on her makeup table. Soon I was trying lipstick on my own lips and, after looking for tips on the internet, trying some of her mascara and eye liner to enhance my eyes. I discovered that I was a very pretty boy.

It got to the point where I could not wait for mom to leave for work so that I could explore her makeup even more. I always waited at least an hour after she left, to ensure she would not come home feeling sick, or having forgotten something (I almost got caught once early on, and so I was very careful after that.). Every evening I started with painting my fingernails and touching up my toe nails. Yeah, I left those painted all the time and made sure that no one at home or at school ever saw me without socks!

I had no idea where this was going. I didn't want to be a girl. I didn't feel gay at all. Well, truthfully, I didn't feel anything though I did get a hardon. I just.... it just made me feel good to put on a bit of makeup and a pair of stockings and walk around in mom's heels for awhile. I did wank off while dressed up. I couldn't help it, honestly!

I have no idea if mom knew I was going through her things. She must have noticed things out of place, but she never asked me.

But I had no plans for this to go anywhere. It was just something to do with my evenings instead of watching tv, or doing homework!

My point here, I guess, is that if I'd had a father to set examples for me, my life might have turned out differently.

Well, a regular father anyway. As it turned out.....

So as I say, my father had left us when I was about four years old, and I cannot remember anything about him at all. A few times a year I would pester mom for information about him. Anything really... a name... what he did for a living.... why he had left. Every time, mom would deflect the conversation, though sometimes she would get downright angry and begin to cry!

Finally, some time around when I was fifteen, she told me that once I turned eighteen she would tell me about my father. And anytime after that, when I brought the topic up, she would just say "When you are eighteen!" and that was all it took to shut me up.

So, here it was February and my eighteenth birthday was four days ago and I was asking my mother when she was going to tell me about my father. She looked frustrated, and angry, but also, I could see a look of resignation on her face.

A week later, I got my wish, and my life changed.

I came home from school as usual and could smell dinner cooking. Mom was quiet over dinner. Usually we had some conversation, but this night she barely spoke. After dinner, I cleaned up the dishes as usual while Mom went to her room to finish preparing for work. Usually Mom would just head out the door after giving me my usual scent-filled peck on the cheek.

But that night, Mom asked me to go to my room and wait. Soon after, I heard the door buzzer and Mom pressing the switch to let someone into the building. Then there was a knock at the door and I heard muffled voices. Shortly after, Mom came to my bedroom.

"Timmy your father is here to see you. I want you to wait a few minutes while I leave. I think it is best that you meet him on your own. We can talk tomorrow night over dinner." She placed her fingers under my chin and raised my head, looking into my eyes and smiling weakly. She gave me my usual cheek kiss and then left.

I was nervous. My father was here!

I heard the apartment door close as my mother left. I waited another minute and then walked into the living room.

Sitting on the couch were two people. A tall very handsome bald man, and my aunt Jennifer! Why was she with my father?

I guess I haven't told you about Aunt Jennifer yet, have I? There isn't much to tell really. My earliest memory of Aunt Jennifer is from about a year after my father left. She isn't my real aunt. She's just a friend of my mother who used to visit my mom a couple times a year. She always brought me a present, usually a video game or toy, and mom always left us alone for an hour or so for her to visit with me. I have to say, I always thought she was prettier than my mother. She always dressed very well, and I always noticed her large boobs. Her perfume was different than my mom's, and I always made a point of inhaling her scent deeply.

Aunt Jennifer visited a couple times a year for a few years, then once more a couple years later, but I had not seen her in almost ten years. I just assumed she had moved away.

As I stood in front of them, I asked the man, "Are you my father?" The man looked at Aunt Jennifer who nodded at him. He stood, picked up his briefcase and walked past me, looking deep into my eyes and smiling. He went down the hallway, into my bedroom, and closed the door.

"Where's he going?" I asked.

"He's giving us a bit of privacy." said Aunt Jennifer. "Come and sit here Timmy!" She patted the couch beside her.

A bit hesitantly, I did so. I smiled as the scent of her perfume hit me. She smelled just as she had years ago.

"What's going on? Why are you here?" I asked. "Why did my father leave us alone?"

"Timmy. I knew your mother years ago. Your mother and I were very close. Very very close. We were in love!"

"My mother was in love with a woman?" My face showed my surprise.

"Not exactly, Timmy. Let me show you some pictures." She opened her large purse and pulled out a tablet. She opened an app and showed me the first picture. It was my mother, and a man of about her own age. He was slim and very handsome, though in a way that might almost be called pretty.

"That's my dad?"

"Yes, that man is your father Timmy!"

She then flipped through several more pictures, which showed my mother and father in several happy situations. At bars with friends, on a trip down south somewhere, a wedding photo, and in various photos around this very apartment.

"Your mother was very happy Timmy, but your father wasn't as happy as he wanted to be." The next picture showed a closeup of my father's face. He had been crying. And his makeup was running. I was stunned. Yes, the man from all of the other pictures, was wearing mascara and lipstick and it was all a mess from the tears running down his face. I don't know who would take such a picture, or why they would keep it, but there it was.

The next few pictures showed the man looking happier, but they showed him wearing panties and bras and stockings... sometimes dresses... usually with lipstick and other makeup. Most pictures were taken with a cell phone camera in a mirror. But there were a few pictures taken in a bar, obviously by other people. There were other people in the pictures. Most were also men dressed as women, though in one the man... my father?... was leaning against another man, who had his arm around him, and the other man has a big lipstick stain on his cheek that matched the shade worn by my father.

"What do you think Timmy?" asked Aunt Jennifer, her shoulder touching mine as we stared at the pictures. Her aroma was intoxicating and I could see down her cleavage. My cock was getting erect and I tried to shift to a more comfortable position.

"I... I don't know what to think, auntie!" I said honestly.

She put down the tablet and looked at me. She took my hand and held it between hers. "Your mother tells me that you have been regularly going through her clothing and makeup. Is that true?"

"Um...." So she HAD noticed! I was beet red as I just nodded.

"I'm glad you feel that you can tell me that, Timmy! I know that many young men have the urge to explore their feelings when they reach puberty. I was that way too!"

"You?" I asked her? Hey, remember that I said I wasn't all that bright? Well it had not yet quite sunk into me yet.

"Yes, me Timmy. Those pictures you are looking at. Those are pictures of me! I am the man in those pictures!"

"You are? You mean...?"

"Yes Timmy. I am your father. When I was born my name was Martin. I grew up as a normal young boy. I got a good job and married your mother, and we had a beautiful baby boy. But I knew deep in my heart that I was meant to be a girl... a woman. And finally I could not resist that anymore and I moved away from you and your mother. It was the biggest heartbreak I have ever suffered... giving you up.

"But I had to be myself. I had to have the room to find out who I really was... to be myself."

"So you mean.... you're a woman now? I've heard of people who have had a sex change..." I said.

"Not quite, baby. You see, when I moved away and started living as a woman, I had some facial and other surgery soon after, and I started on female hormones. I found.... I found that they changed me, or rather, that they helped me find out even more about myself. I found that I became a very sexual creature. I liked sex. I craved sex.

"And, I liked my penis... my cock.

"You do remember me visiting you? You remember your Aunt Jennifer. Not just because of the Christmas gifts I send each year?"

"Yeah. I remember you visiting a few times. Sort of. But you never looked like this!"

Aunt Jennifer grinned. "Of course not, baby. That was before I had more surgeries. And definitely before I had these!" She cupped her hands under her breasts and lifted them. Her breasts were very large!

"But you stopped coming!"

"No baby, I stopped visiting," she almost laughed. "I never stopped cumming!"

"Your mother stopped me from visiting you. She threatened to go to court and get an order. Much as I hated to do so, I stopped visiting. I did not want that order. I figured that some day she might change her mind!"

"Why would she do that?"

"Your mother found out how I had started making a living, baby!"

"How.. How was that?"

"I never did have the surgery to become a woman. I still have my cock."

"You still.... Can I see?" I blurted out before I could think of what I was saying.

"Yes, baby. I have no secrets from you." She stood up and removed her skirt. My aunt Jennifer was wearing stockings and a garter belt. Under the belt she was wearing panties, which had clasps at the side. Masked by the panties was what appeared to be a cock! The panties were stained with lots of moisture where the head of her penis was nestled. "But.... you have to understand sweetie. You are such a pretty boy. You have been having an effect on me, just sitting here beside me."

She unclasped the panties at the side and drew them off. Freed of the restriction, her penis swung down from her body. It was large. It was thick. It was very wet. It was drooling precum. A long strand hung from the very tip.

I looked up at her beautiful face, then down past her large bosom, back down to her cock.

"Aunt Jennifer... you are SO beautiful!"

"Oh, baby! I was so afraid of what you might think!"

Almost involuntarily, my hand reached out, and then I realized what I was doing and I drew it back.

"Do you want to touch it baby? It's alright if you want to. It's getting hard because of you. All that jizz I am leaking is because you are such a pretty boy!"

I reached out again and my fingers touched the tip. It leapt upwards, getting even harder. Then my hand grasped her cock just below the head and auntie let out a sensual groan.

"Have you ever touched anyone else's cock before?"

I shook my head, no. My eyes did not leave her cock. I was fascinated by it. It felt so warm in my hands. It was hard, yet spongy. As I watched, the pee hole pulsed and some more precum slid out of the hole and drooled down in a string. It almost hit the carpet before I used my other hand to catch it. I didn't want to make a mess in the living room!

"Rub that around the head of my cock, dearie!" said auntie. I did that, and I found myself caressing her hot cock. I had seen videos online, of course, of people having all kinds of sex. So I had seen plenty of cocks fisted, and teased. But I had never thought that I would be... I mean, why would I have ever thought I would have a beautiful woman's cock in my hands?

"That feels SO good baby. You have wonderful hands! Why don't you stand up and give your auntie a kiss!" I did stand, but did not let go of her cock. Auntie drew me to her and then placed her lips on mine. And then she kissed me. Not a gentle kiss on the cheek like momma gave me, but a full kiss on the lips. Her lipstick felt so wonderful!

And then she put her tongue in my mouth, and kissed me with passion. Our tongues swirled and I almost fainted from lack of oxygen.

Then I felt auntie's hands tugging at my belt and my pants fell to the floor. My underwear swiftly followed and auntie had my own cock in her hands!

I was also leaking precum and auntie used her hand to quickly spread the slickness around my cock head and shaft. I almost came right away at her touch, but not quite. Her hand felt SO good!. My own hand mimicked her actions.

Auntie kissed me harder. The waxy sensation of her lips on mine was so sexy. Her perfume was intoxicating. Her mouth was delicious. Briefly she released my cock and drew me tightly to her. My cock pressed against hers and my body spasmed. But not my cock. "Not yet baby! Mommy will make you cum, but not yet!"

We again resumed sliding our hands up and down each other's cocks. I looked down at the delightful dick in my hands. I was close.... so close.... but then auntie arched her back and moaned. I felt her cock pulse and then she shot several ropes of cum that splashed against my belly!

"I'm cumming!" I cried. Just as the first jet was about to leap from my dick, auntie fell to her knees and took my cock in her mouth! I shot three streams of jism into her mouth as those beautiful red lips sucked on me! Auntie looked me square in the eyes as she pulled back to show me her mouth full of my cum, then she swallowed and opened her mouth again to show me it was all gone.

I collapsed on the couch, panting. Auntie plopped down beside me and smiled.

"Was I the first person to touch your cock, sweetie?"

"Uh huh," I replied. "That was... that was wonderful!"

"For me too, baby. For me too," she said. My belly was covered with her jism, though it had started running down my legs. She used a finger to scoop up a blob, and popped it into her mouth. She then scooped up another blob and offered the finger to me. I hesitated and then opened my mouth. She slid the finger in and I closed my lips. She then moved her finger back and forth slowly and I sucked on it as if it was a miniature cock. My cum... her cum... it was my first taste of cum. It tasted salty, but also strangely sweet. It was my auntie's cum!

Auntie raised her voice. "You can come out now Roger!" And the man came back from the hallway. I reached for my shorts to cover my dick, but auntie laughed. "You need to get used to people seeing you naked if you want to come and live with me!" she said.

Auntie was putting the rest of her clothing back on. Roger just stood there smiling, but also looking at me strangely. When I looked right at him he just smiled, and winked!

"Live with you? You want me to come live with you?"

"Not right away sweetie. But soon. It is what you want, isn't it?"

Was it what I wanted. I hadn't even thought about it. But when I DID give it a thought,.. "Yes, auntie Jennifer. I want to come live with you. I... I want to BE like you! You're beautiful!"

"Well if you want to live with me. If you want to become like me... well, you have to prove yourself first!"

"Prove myself?" I asked. "How do I do that?"

"Don't worry sweetie, I'll let you know. I'll guide you. Roger will come by tomorrow night at eight to help you begin, won't you Roger!"

"Yes, Miss Jennifer. I'm sure Timmy and I will get along just fine."

"Hmm.... not Timmy. Call him Baby, Roger! He is about to be reborn!"

"And Baby.... after everything we just talked about, I think it is appropriate for you to stop calling me auntie now. You can call me Mommy Jennifer!"

With that, she and Roger left.

I had to spend the next half hour cleaning myself up, and cleaning up the couch and carpet, removing any of the spilled cum that I could find.

It was only later, when I went to bed that Auntie... no, Mommy Jennifer's words sank in. I had just jerked off and been sucked off by my own biological father!

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5 Comments
AnonymousAnonymousover 1 year ago

sissy boy and his sissy father! what a great combo! wow, turned me on!

you asked in the intro -

Please leave feedback as it encourages me to write more!

so I am greatly encouraging YOU .. urging you .. please continue !!!

petey377petey377over 1 year ago

oh my want to know what happens next please

300bowler300300bowler300over 1 year ago

More, Please...Lots more...!!!! Hugs and Kisses Betty jo xoxo

KatiwantsKatiwantsover 1 year ago

Wow so very wonderful!! I hope there will more to cummmmm!!!

jrichard1953jrichard1953over 1 year ago

Loved this story. can't wait to see how it develops!

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