Sweety

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My journey from boi to girl began with a simple word.
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"Sweety"

That was the word that changed my whole life. Or at least started to change it, I think. It wasn't the word itself; it was the moment that created the idea. The idea I wasn't who I was supposed to be. I wasn't a shy boy; I was a pretty girl that found her bliss in the arms of a man taking care of her. And me taking care of him.

Of course, I had no idea it was happening at the time.

"Sweety! Bring that tight ass over here and serve me!" I heard the rough voice say from behind my back. I felt my face flush, my cheeks turning deep red with embarrassment, my heart pounding. I knew where the voice was coming from; a pack of construction workers had arrived minutes earlier and spread themselves out over a corner booth. I knew as soon as I turned around, the man would realize his mistake, that my ass didn't belong to a cute waitress, rather a shy slim 18-year boy.

"Honey, we don't have all day." He said as I bit my lip down hard and turned to face him.

I don't know who was more embarrassed, him or me. As soon as he saw me, he started slumping down in his seat as his friends began to laugh and make fun of him. I tried my best not to look at him, took their order, smiling politely as they called him gay, faggot, sissy, some even suggesting he get my phone number. As I walked back to the counter, I had never felt so self-conscious. I could feel their eyes on my ass, loudly daring their friend to enjoy the view. For the rest of my shift, I kept my head down, staying away from the other waitresses. I couldn't bear anyone else making fun of me.

I shouldn't have been that surprised that he made the mistake of thinking I was a girl. I wasn't the most masculine guy in the world. I was a skinny eighteen-year-old, my skin was fair soft like an elf, and the only fat on my body was on my behind. I had tried to exercise it away once, but I had only made my butt more feminine. All of that and my uniform is a tight white shirt and skintight black jeans, which could have made me look like a girl from behind.

I had worked in the small diner for the last six months since dropping out of school. My mother convinced the owner to hire me as a waiter even though he only seemed to hire waitresses. She had a way of convincing men to do all sorts of things. Even though she was halfway through her forties, she was a stunner. She made sure always to wear flirty makeup, tight clothes, and high heels - but even if she hadn't, her large natural breast, round ass, and long blond hair would have made sure every guy she met chased after her.

Mom, or Carol as she liked me to call her since she felt too young to be called mom, had gotten pregnant at fifteen with some boy she barely knew. He bolted as soon as he found about me, and her parents weren't much more supportive. Since then, her main goal in life had been to take care of me, and she did a pretty good job. It took me years to realize how little we had and how hard she had to work for me not to notice.

After my shift finally ended, I popped behind the diner for a smoke while waiting for Mom to finish her shift. Since I was the only smoker, I could avoid any more jokes at my expense. I just wanted to forget what happened. But something about it stuck with me. I wasn't much of a lady's man, to begin with, and this, another man thinking I was a woman, wasn't going to help much with my confidence. I wondered if the few girls I had kissed had felt that way too. Did they feel like they were kissing a girl?

After probably more than three cigarettes, I headed back into the diner, looking for Mom. As I entered, I could hear her giggling, a ditzy bimbo type of sound she made when she meets someone she was attracted to. I quietly peeked into the diner to find her sitting on a man's lap, laughing and flirting. She glanced to me, giving that familiar sign; I'll be home late, don't wait up. This wasn't the first, second, or third time something like this happened, so I just let myself disappear without a sound.

On the bus ride home, I couldn't stop thinking about the incident. The uncomfortable feeling that a man had looked at my ass and found it to be sexy. Was it just an accident, a quick moment, or was my ass that feminine? I looked around the bus, the few stragglers on their way home, and suddenly felt self-conscious. I felt as though everyone was looking at my ass, staring at it.

We lived in a tiny one-bedroom apartment. It was the only thing we could afford, and that barely. It seemed like every other month, mom would have to take extra shifts and stay late to clean at the diner to make rent. My mom had tried once to save to go to college, but as I got old enough, I told her I had no interest in going. Of course, it wasn't true, but I couldn't bear putting more stress on her life.

I rushed inside as soon as I got home, still thinking about the incident. I threw my jacket on the couch; it was still pulled out and with a sheet from this morning. Mom slept on the couch and let me have my room. I took a long look at myself in the mirror in my room. With my back turned to it, leaning back, I tried to imagine what the trucked had seen. I couldn't believe that I hadn't seen it before. With my tight black pants hugging it, my ass came out nicely round, soft yet firm.

But maybe it was just the pants, I hoped.

I took off the pants, tight boxer shorts underneath and looked in the mirror again. My ass was still feminine, but the boxer shorts at least made it less so. I breathed a sigh of relief and started planning to ask permission to wear jeans to work. But then butterflies began to flutter in my stomach. And an idea started forcing its way into my mind.

What would it look like if I wore panties? Would it look like I was a girl?

Without thinking, I reached into the dresser to mom's underwear drawer. We had to share the dresser since the only place in the apartment to keep a dresser was my room.

Her underwear drawer was a total mess, thongs, girl boxers, and panties heaped together. She would never notice if I took one and tried it on. I grabbed a pair of black girl lace shorts. I couldn't believe how soft they felt, running up my legs. I adjusted my penis, tucked it in, and turned to the mirror. I didn't even realize I was holding my breath ... until I saw.

A nice bubble butt hugged by lace shorts. Not only a feminine ass but a sexy one too. My mind started to wander. I wondered if this was what the trucked had imagined was under my jeans when he called out. I wondered if he had fantasized about touching my ass, caressing it, kissing it. Then without warning, a thought popped into my head. What if he got hard watching my ass. His cock straining against his jeans.

I looked back in the mirror, only now realizing I had been caressing my ass and seeing that my dick was sticking out of the boxers. I let my hand down into the panties, pushing my dick back down, tucking it in. I started rubbing it ever so slowly ... when I heard the front door open.

The world suddenly went into slow motion. I could feel my heart pounding like it was trying to escape my chest. I quickly turned to lock on the door, reached down for my pants, struggling to get them back on. Felt like they had shrunk somehow.

Click. The front door closed, followed by laughter and the sounds of two people stumbling across the living room. Mother was drunk.

"Shush, be quiet," she said. "My son is sleeping in the other room. "

My heart started to get back to its normal rhythm. If I just made sure to be quiet, my secret would be safe. But, I couldn't believe what I had been thinking—trying on mom's panties.

"I thought you liked to make noise," a gruff manly voice said.

It must be the man in the suit from earlier, I thought. He must be married or something since mom brought him home instead of going to his place.

"I been known to make a lot of noise, Ted. But has to wait for next time". My mother said in a hushed voice.

"I look forward to it." The man said. "Now, let me see those special skills you were bragging about."

This was not the first time my mother had brought someone home with her, and unfortunately, my room wasn't soundproof. Usually, I would ignore these visits by putting on headphones, blasting whatever pop music was popular at that time. The guys mainly were gone the following day. But this time was different. I found myself leaning with my ear against the door.

I could hear him grunting, taking deep breaths, and blowing them out his nose. And a wet slurping sound in a constant rhythm.

"Deeper," he moaned. "Deeper."

My heart began racing again. I was matching the rhythm of the slurping sound. My cock straining against the fabric of the panties as his groaning becoming louder.

Listening wasn't enough. I had to see it. So gently turning the doorknob, and ever slowly pushed the door open, creating a crack just big enough to see through.

There he was. And older handsome man, muscular build and just a hint of a belly. He sat on the couch, feet apart, his pants down his ankles. My mother nestled in between his thighs. I could see her blonde hair bobbing up and down, on all fours and ass up in the air. His cock disappearing into her throat.

His eyes were closed, head hunched back, clearly enjoying my mother's mouth. He bit his lip in-between moans. My hands started to rub my dick through my panties, feeling the wetness of the precum that was dripping out. I opened the door just an inch further, trying to get a better look, realizing I wanted to see his cock. I couldn't believe myself; why was I thinking about another man's cock.

My heart skipped a beat when I saw my mother get to her feet. I tried as I could, but she was blocking my view as she danced around, taking off her shirt and jeans, revealing a tiny little red thong wrapped around her tight ass. It didn't stay on for long, as the man ripped it off and pulled my mother onto his lap.

"I'm going to take that beautiful little ass now," his strong, built arms holding, squeezing my mother's buttocks.

My mother kissed him deeply, manoeuvred her pussy onto his cock, letting out a low grunt as she did.

"Nothing goes into this ass unless there's a ring on my finger," she said, bouncing on his manhood.

The man smacked my mother's ass, started moving his hips in step with her, his mouth engulfing her breasts, enjoying my mother's company. But with just a little less enthusiasm than before. He looked a bit disappointed.

I slowly closed the door, the moaning echoing in my room. Lying in bed listening to my mother get fucked, one hand caressing my ass, feeling the softness of the panties, I came harder than ever thought possible.

Spent, emotionally and physically, I drifted off to sleep.

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PlatstelpaPlatstelpaalmost 3 years agoAuthor

Thank you everyone for your positive comments, I'm working on the next chapter, so hopefully soon.

AnonymousAnonymousalmost 3 years ago

Please continue this :)

Riki1942Riki1942almost 3 years ago

This was a very good start and set up for another chapter. I hope the story continues!

AnonymousAnonymousalmost 3 years ago

part 2 please

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