The Life of Ty

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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TheMilkman
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The Life of Ty

Post by TheMilkman »

Chapter 1: Introduction

I couldn't sleep. All I could think about was school. It was all too much. It should be illegal to put boys and girls in a prison everyday. It's all anxiety.

Ty just held onto his knees as his phone began to buzz. It was morning before the sun said hello. It was criminal how early he had to get up. Ty just jumped to his feet as he dragged himself to the bathroom. His long brown hair came down over his skinny pale body. Ty pulled on the waistband of his undies as he brushed his teeth.

"Woah lookie lookie!" Ty's little sister Ashley made her presence known as she woahed and pointed at her brother in his bright white undies. Ashley was three years younger than Ty but had the same long brown hair he did. A naked boy was unfamiliar to her and new territory. Ty pushed his sister into the hall as he moved to his room.

Ashley is so weird. Why can't she just be a normal sister. She's like a little gremlin. A monster in a little girl's body.

Their mother Cindy was ready to push the kids out the door. Ty pulled together a simple outfit of jeans and a plane shirt. The car ride only pulled the anxiety to the foreground as Ty thought about the battle ground that was fifth grade.

The whole year he spent his time like money trying to buy the affection of one girl. Ginny was the perfect girl to have a crush on. Her country accent was heaven and her blonde hair was the color of the sun. It was everything a boy could hope for.

Fourth grade was a tuff battlefield but at least Ty had a brother in this mess. Steven was tall and lengthy with his messy, curly, poofy hair.

Steven was vibing against the wall of the school as they pulled up. The brick wall was the perfect setting for the music video in Steven's head as he swayed and bobbed.

Look at this dork. Doesn't he know people are looking. I wish I could try not to care.

Ty left his thoughts in the care as he left with his sister following behind him. Steven pulled out his earbuds as he saw them approach.

"I been listening to this new song." Steven's dead slow voice crawled out as he flashed Ty his phone screen. Ashley made herself scarce as the boys walked into the school. The line for the lunch room was getting long as Ty spotted his first hurdle. Mat was being his normal crazy self as he was making a gun with his fingers and shouting die.

Mat was a pig, a brute, and a bully. His head was shaved and his eyes were mean. As Ty entered the lunch line he saw her. Ginny was just a couple people ahead of him. Ty pulled all the air into his gut before mustering up the nerve to talk to her. Too bad he was sorely interrupted before even getting words out.

"Dork!" Mat made eye contact from his spot a couple people in front of Ginny. "Morning dork!" Ty just kept quiet in his own little space as the honking voice of Mat cut through the morning air.

Ginny just didn't seem to notice anything happened around her as she was lost in conversation. Ty just didn't seem to have the hunger to stay in line. Ty just pulled his chin up as he started his strut for the playground. His eyes stayed to the left watching the girls talk as a foot found its way in front of him. Ty tripped falling to the ground as he put his hands out forward. Ginny couldn't help but hold back a laugh as Mat began explaining how bumbley Ty was.

Oh I just want to hit him. But I don't know how to. My arms feel like string. I'm not sure if I'm capable of throwing a punch. How do you even throw a good punch.

"Here let me help you up," Mat said, stepping out of line. Ty did not need his help. He did not want it. Ty would rather lay on the ground than receive help from the likes of him. This was not an option as Ty felt hands slide into his pants grabbing his underwear by their waistband. "Lift off!" And just like that Ty was lifted off the ground by his underwear. His tight white booty sleeve were yanked high letting him dangle as the line roared with laughter.

"Oh my....Ty......I can see your bridges," Ginny squawked covering her giggles. Once the line seemed to move Mat dropped him heading inside. Ty just laid on the ground fixing his underwear.

This was the life of our pour child. Fourth grade was a death trap filled with pitfalls and he had to navigate them all.
Supermario17
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Re: The Life of Ty

Post by Supermario17 »

Nice work, hopefully more soon.
TheMilkman
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Re: The Life of Ty

Post by TheMilkman »

Chapter 2: Wet Fruit

The scent of bacon brought Ty to his feet. The air around him was stale like the stink lines he created. Ty grabbed his towel as he walked across the hall. The bathroom lay empty as he locked the door behind himself. His hands shook a bit nervous as he thought about being seen in such a light outside the confines of this room. Ty gently pulled his undies down to the floor stepping out of them. Ty's limp noodle rested between his legs as he popped on the shower.

Are you talking to me? There's no one else here so you must be talking to me.

Ty's baby banana bounced between this thighs as his inner monologue spouted movie quotes in the mirror.

Come with me if you want to live. Shaken not stirred. Bond, James Bond.

Soon the water was hot enough. As he pulled himself under the shower his turtle peaked its head out. A couple of show tunes later and he was all cleaned up and ready to party. Showers used to feel like torture for Ty but now he enjoys them getting a little time to sing his heart out and not feel like a sissy. With his towel wrapped around his waist he made haste to the laundry basket.

The path was set. There was a couple feet of distance down the hall, and then the stairs, after a corner around the kitchen there was the living room with the laundry basket sitting right on the couch.

Ty just crossed the room as he dived into the basket for his clothes. Unbeknownst to him another sat quietly in the corner. Sitting calmly in the big chair next to the fireplace was Jessie, the typical mother's friend type. She was young at 27, and a babe to be sure with her short curly blonde hair as perky lips. She was surprised to have an almost naked Ty enter her sights but not put off by it in the slightest. Her lips puckered out as she watched his hips sway across the room. Jessie bit the tip of her fingernail as she watched his body climb onto the hamper. His legs dangled as he searched aimlessly. Jessie couldn't help but think about the last time she was in the presence of a strapping young man. And then it happened. Ty's towel decided it was too tired to continue to hang on to his waist.

Jessie's eyes went wide as they were glued to his bulbous backside. Her mouth fell open as she leaned forward taking in the view. Like a fresh fruit under the faucet Jessie watched a single water droplet slide down the rounding side of the left cheek. Jessie quickly covered her mouth stifling her reaction only for her lips to curl with a giggle.

"Hehehehe." This sound sparked a response from Ty as he pulled his head out of the basket cranning it backwards looking over his fresh rump. Jessie pulled away from her face pinning her hands between her knees as she tilted her head. "Well today sure is my lucky day." With a click of the tongue and a flick of the wrist she pointed out the misshap in front of her. Ty's eyes followed her finger as the sunlight through the curtains shinned off his posterior. The towel resting on the floor flipped a breaker in Ty's head. Jessie multipled into a room full of girls as he butt was on full display. His cheek began to flare up with embarrassment. His limp noodle twitched as blood rushed through his body. Like a dear in headlights he stood, hands in a laundry basket, frozen (petrified even) to the thought that someone (a pretty girl even) was seeing him naked.

Ty looked down at his growing embarrassment as something else began to grow. Limp no longer was his manhood. It suddenly became a vicious cycle.

Embarrassment = Excitement

Excitement = Embarrassment

It was a problem spiraling out of control. Ty bounced on his feet as his member flopped. The thought of her seeing his pecker as well was to much.

"Oh Ty your so adorable with this little guy hanging between there. Wow look at him, excited to see me. Woohoo so cute, dance for me." All these thoughts of what she might say swirled around in his head until he realized reality was much worse.

"I see London." Her words came up quickly as he heard her get up. "I see France." Her foot steps pulled her close. This was a nightmare.

No Jessie go back to London. I hear the weather is nice, and there's so many sights to see, and so many places to eat at.

Panic was crashing him out as he wiggled back and forth on his feet like an animal trying to scare off prey. Ty hoped her sight seeing adventures were over but they had just begun.

"I see a little boy with no underpants." And just like that Jessie was on her knees face first with the naked bottom. "Let's get you cover." And with that she pulled up his towel wrapping it around his waist. Ty's face shot right up as his body trembled. Jessie's lips exhaled a soft giggle as her face pressed against the full mood making a soft landing. "We wouldn't want anyone to see you naked now would we?" Her hands pulled the towel up as it slid by his chubby gerth. Jessie pulled the towel tight before standing up more. Before Ty could even think of answering her she curved her face around to his. "Now would we?" And just like that she kissed him on the cheek. Jessie just pulled herself up as she made her way to the kitchen only to stop and look back. "By cutie."
Last edited by TheMilkman on Wed Jul 09, 2025 4:16 pm, edited 1 time in total.
Supermario17
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Re: The Life of Ty

Post by Supermario17 »

Another good chapter, keep it up!
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