Under the shirt.

[jazzkriss21]

Wow, Emily's coming back

[Qwerto1232]

She will be back but not in chapter 7,8 probably in chapter 9 she finaly get her chance to look under that shirt.

[Qwerto1232]

Part.7

Fourth day started similarly as the previous two.
Milton woke up around ten.
Looking at his morning wood painfully reminded him of the promise he gave Helen.
He managed the situation by taking a cold shower.
When he was drying, someone knocked.
Milton put the towel around his waist and opened the door.
No one was there.
He looked around but the corridor was deserted.
Then he look down.
And there it was, a package in brown paper.
He took it inside, pretty sure what was in it.
And he was right.
After he opened it, another long stretched shirt fell on his bed.
”where did she always find these things?” wondered Milton.
There was a note too.
“At 11:00, wait in front of the hotel.”
Nothing more, not even a signature.
Which wasn't necessary, he knew who sent it.

10:55, Milton stood next to the main entrance to his hotel.
Nervously looking at people walking around.
Some of them give him strange looks.
Thanks to his outfit.
He was again in a public place, wearing only a long shirt. Reaching just under his butt.
Together with the shoes, it was all he was wearing.
To avoid people's eyes staring at him, he was looking down.
Which caused him to look at the hem of his shirt.
Which he nervously played with.

Car stopped next to the sidewalk, catching his attention.
It was Helen's car.
Milton approached it slightly faster as he should, the sudden movement made his shirt revealing his buttcheeks.
He quickly covers it with his hands.
Blushing, he was trying to open the car door, but they were locked.
“Hy sweetcheeks,” greet him Helen. Leaning to him from behind the wheel.
“Can I go in?” Asked Milton anxiously.
“Of course, but first I need to check if your outfit is as it should be.”
She smiled at him.
Waiting for him to prove that he is not wearing underwear.
Milton looked at her with pleading eyes.
But her expression didn't change.
So he looked around, and still blushing quickly lifted the front of his shirt.
Revealing his soft penis and balls to Helen's eyes.
And maybe the side of his tights to some lucky bystanders.
Helen was satisfied and opened the door.

“Where are we going? Asked Milton when the car moved.
“Thelma found the perfect flat for you. We are going to meet her.”
Informed him Helen and as before, her hand ended on his knee.

The place was part of the new apartment complex.
As they approached it, Milton noticed they were near the edge of the city.
At last he thought they were.
Judging by the forest he could see behind the complex.
Helen parked at a surprisingly empty parklot.
When they were walking to the complex, it felt strangely empty.
“According to Thelam, the complex has only a few tenants so far.
I think she mentioned that in your block you would be first.”
Helen said as they walked through the nice Iron gate.
The apartment block was in rectangle shape.
Inside was a big community yard; it looks like every apartment had access to it.
“Look, there is even a pool,” Helen pointed at an arrow showing a way to the pool.”
Milton gulped, remembering his experience in Helens pool a few days prior.
“Here we are, number.5.”
Helen stopped in the corner of the building.
“Thelma told me she will be a little late. But the key should be in the lockbox. We can go inside and look around.”
After she found the key they entered the apartment.
“Lamb, you know what to do.” Helen said with her eyes on Milton's shirt.
He sighed and took it off.
Looking around him where to hang it.
“Here, I will hold it for you.”
Helen said when she noticed his look.
He obediently gave her his only pieces of clothes.
And with a bad feeling in his stomach, watched as she put it into her purse.
Helens phone interrupted his dejavu.
She took it and listened for a few seconds.
“Understood, on my way.”
“Honey, I need to go now. Wait here for Thelma, when you finish here she will drive you to my house.”
Helen said, kissed him on the forehead and same as in the bathroom in the cinema. She was gone and with her his only piece of clothing.

Milton found himself again in almost the same situation.
He was alone, naked, without a phone in an empty room.
He had no way of contacting Thelma.
So he just waited, praying that she would arrive soon.
To kill time he started to look around the apartment.
Before he went into another room, he took his shoes off.
He didn't want to drag dirt on the new carpets.
Now he was really naked.

When he stepped into the kitchen, he saw that it was connected to the living room.
Similarly as in that previous place he saw.
This one however, looked bigger.
Or just appeared bigger, because there was no furniture.
From the living room led one door into a small yard.
He carefully looked through the glass door.
The neighbor's had the yard too, between them there was no fence, or privacy screen.
So until he built some, he couldn't go out naked.
”Why would I ever do that” Milton wondered.

Second door led to a bedroom, through a big window he could see the yard again.
To his surprise there was a bed already.
With mattress and bed sheets, no pillows.
It looked brand new.
Milton touched it and pushed, testing the mattress softness.
The he sit.
Wondering how long until Thelma arrives.

His thoughts were interrupted by the sound of the door opening.
”She is here” he thought.
He didn't know what got into him, but he decided to have some fun.
Maybe it was the state of arousal he was in.
Milton jumped on the bed, at all four. His butt facing the door, with his knees apart.
First thing that Thelma would see, when she enters, would be his balls, hard penis and even his butt hole.
Milton giggled, when he heard the door behind him open.

“WHAT THE FUCK IS THIS??” some strange raspy voice asked.
Milton looked over his shoulder, in the door wasn't standing Thelma.
But some frightening strong women.
She was glaring at him with an angry expression.
He was so shocked he didn't move.
Showing this angry woman all his private places.
“ARE YOU DEAF, ANSWER ME!!” She yeled with that raspy voice.
Approaching the bed, her imposant statue towering over the scared naked boy.
Milton was so scared he couldn't answer.
The woman took Milton's arm and surprisingly easily dragged him on his feet.
Standing side to side, Milton saw she was a head taller.
“LET'S GO PERV, I WILL DEAL WITH YOU IN MY PLACE.”
She said and started to drag him outside. She doesn't even let him put shoes on.
When the door behind them closed with a loud click, Milton realized he was separated from his shoes.
The woman was walking in the direction to the opposite corner of the building. Dragging Milton with her.
He thanked God that the complex was empty, so nobody could see his walk of shame.

They ended in a similar apartment, but this one was fully lived in.
Inside she led him into a corner.
“HANDS BEHIND YOUR HEAD!”
She commanded, and delivered a sharp slap on his buttcheek when she tought he didn't move fast enough.
“DON'T MOVE!” She hissed.
If she wanted to say something more, she didn't get a chance.
Because her phone started to ring.
“I just wanted to call you. You won't believe what I found in one of the apartments.” The woman said when she picked up her phone.
Then there was a few seconds of silence.
Probably the person who was calling was answering the question.
“How the hell did you know that.? Is this some sort of joke?.”
Finally the women talked again, followed by another few seconds of silence.
“Well that's something.” the unknown woman continued in her phone call.
“In my apartment.”
“Yes he had.”
“Wait.”
Milton tried to catch another side of the conversation, but all he could hear was movements of the women behind him.
And some strange familiar snapping sound.
“Done, sended. Send me the address.” The woman said and ended the call.
“You can turn around, Milton.”
He exhaled when he heard his name. She must talk with someone who knows him.
Maybee Thelma or Helen.
He slowly turned, and started to put his hands down.
“Ee, hands stay behind your head.” The women hissed.
Milton, now facing her, could see that the anger expression was gone.
“So you are not a pervert.” She said, and before Milton could say something in his defense, she continued.
“At last, not that kind I tought.”
She said and watched as Milton's penis started to erect.
When he was fully hard she said.
“Ok, lets go.”
“Wwhere?” Wanted Milton know.
“You will see.” It was the only answer he got from her.
After that they leave her apartment.
She instructed him to walk in front of her.
That way, she could watch his buttcheeks flexing with each step.
They walked behind the building into a small parking lot.
With only one car.
She opened it and they both went in.
During the drive went silent.
Milton was still slightly scared, which caused his erection to fade.
His mood changed when he recognized the neighborhood.
They headed to Helen house.

After the woman parked in front of Helen's haus, she stepped out and went around the car.
She opened Milton's door and just said in a commanding manner.
“Follow me.”
Milton walked behind her to Helen's front door.
When they reached it, the woman said over her shoulder.
“Stay there.”
And she pushed the doorbell.
Because of the woman's strong frame, Milton was completely covered by her.
When Helen opened the door all she could see was the women.
“Can I help you?” Milton hears Helen ask.
“I am Barbara, I work as the manager In south apartment complex. Today I found something that belongs to you.”
“Nice to meet you Barbara, what did you find?” Asked Helen.
Instead of answering Barbara, just step aside.
Revealing naked Milton standing behind her, blushing and trembling.
When Helen saw him she smiled and said.
“O, yes. This one belongs to me.”
Barbara chuckled.
“Please come inside, you must tell me what happend.”
Helen said and invited Barbara inside. Milton followed her, when he walked over Helen she leaned to him and whispered.
“I hope you weren't a bad boy. You know what happened to bad boys.”
Milton gulped.
“Go and make us a coffee.” Helen said and with a slap on the butt sended him to the kitchen.
She and Barbara sit in the living room.
And Barbara started to explain what happened.
Milton could hear every other sentence.
“Imagine my shock when I opened that door and the first thing I saw was a pink asshole and a pair of balls.”
He heard Barbara say.
“OH my” reacted Helen, and Barbara continued.
Next thing Milton could hear was: “Marsh him naked to my apartment.”
“Thelma called.”

When he brings the coffee into the living room. Barbara finished her talk and asked.
“So If I may ask? What is the deal here?”
Helen waited til Milton put the cups in front of them, and then she gestured to him to stand next to her chair.
When he did it, her hand immediately couped his buttcheek.
Barbara smiled when she saw it and he blushed even more.
After one squeez Helen started to explain what happened from the second she saw him fall on the floor in the cinema and soiled his clothes.
As she was talking, her hand gently played with his cheek.
Squeez, fondel, gentl pat.
Keeping him on edge.
Milton could just stand there looking down avoiding Barbar's eyes.
When Helen gets to the part when she makes him cum in the cinema.
Milton looked up and met eyes with smirking Barbara.
She started looking down.
Milton followed her gaze, which ended on his hard throbbing penis.
His hands jerked as he almost covered himself.
Helen continued her talk when she finished her hand stay on Milton's butt.
Possessively couping his cheek.
“Wow, that was incredible. “ said Barbara “I hope Milton will move into that apartment. It will be great to have such a good obedient boy so close.”
“Of course if you will be ok with it?” Barbara aske Helen.
Milton wanted to say something but he realized she wasn't asking him.
Helen laughed “OH not at all, we can discuss this later.”
“Yea I took enough of your time.” Said Barbara and started to stand.
“Before you go, I think you could help Milton with his problem.”
Helen said, and with one finger pushed Milton's erection down and let it spring up.
Milton moaned.
“Really can I?” Asked Barbara with disbelief.
Helen just noded.
“Come here, aunt Barb will make you feel good.”
Said Barbara with her raspy voice and stretched her hands in front of her.
Milton looked at Helen, who just smiled and nodded slightly.
Milton slowly started to walk, his penis pointing to Barbara.
When he was in her reach, she swiftly grabbed his hips with both of her hands and easily turned him around.
Then she sat him into her lap.
“Damn you handled him like a small child. You must be strong.”
Reacted Helen.
“I train regularly, an old habit from my army career.”
Barbara explained as she positioned Milton in her lap.
His legs were held apart by Barbar's legs.
With one of her hand she put Milton's hands behind his head and held them there.
She pushed him slightly back so he was leaning into the chair.
And she could look at him from the side.
It wasn't the most comfortable position but that doesn't matter now.
With her one free hand Barbara started to explore his exposed skin.
First his collarbone from there she circled his niples and continued down to his belly button.
Milton started breathing deeply.
Waiting for her to finally touch his penis.
But Barbara was taking the time.
She circled around his belly button.
And watch how his penis started to twitch.
“OH, someone is excited,” Barbara whispered into his ear.
Another twitch.
Barbara put her hand over Milton's mushroom, but she didn't touch it.
Her fingers stop one centimeter from it.
Milton moved his hips up, in an attempt to touch Barbara's fingers.
But she expected it and moved her hand outside his reach.
Poor horny Milton tried it a couple of times.
Moving his hips up and down up and down.
But the hand always avoided him.
“Someone is needy.” Said Barbara smiling and exchanged looks with Helen.
“Please, “said Milton quietly, “make me cum. I need to cum.”
He almost whispered, eyes closed, blushing.
“Well if you ask so nicely.”
Said Barbara and firmly grabbed his throbbing penis.
Pleasurable moan escaped Milton's lips, when Barbara started to stroke him.
Moans, whimpers and deep breaths filled the room.
“That's a good boy.” whispered Barbara into Milton's ear and licked it.
Simultaneously she smeared precum on his mushroom.
“Cum for aunt Barbara. “
“Ahaah”
Milton moaned as his balls raised up, his butt clenched and ropes of cum flyed on the glass coffee table in front of them.
“OH wow, that is a big load. When were the last time you masturbated?”
Asked surprised Barbara.
“Two days ago.” Answered her question Helen.
Barbara node with appreciation.
After his climax calmed, Milton put his head on Barbara's shoulder, she moved his legs together and turned him to the side, so he was seated in her lap as a child.
Then she cuddled with him for a few minutes.
Until he fell asleep.

[jazzkriss21]

Will you be continuing this story?

[Qwerto1232]

Yes, but it will not be so fast as previous chapters. When I started posting i already had 5 chapters ready. Now we reached the point when I need to write next chapters. Chapter.8 is already in proces I had 1/3 of it already writen, maybee next week I will post it.

[Qwerto1232]

Good news i manged to finish new chapter today. Enjoy it.

Part.8

Milton woke up late, later than usual.
Sunlight from the window illuminated his closed eyelids.
His hotel bed felt really nice, then he remembered.
He wasn't in the hotel, he was in Helen's house.
He opened his eyes and looked around.
He was in a big bed in a very nice room.
After he stood from the bed He felt a fluffy rug under his bare feet.
When he looked down he saw his morning wood.
Usually he would take care of it.
But he promised Helen he wouldn't masturbate.
Maybe if he found her she would help him.
Milton left the room, painfully aware of his naked state.
Even when he spent the last five days basically naked, he still cannot get used to it.
As he carefully walked over Helen's house he thought about his new life.
Which makes him aroused.
The house was unusually quiet.
“Helen! Are you home?”
No answer, just silence.
After he found the bathroom and washed, he went downstairs.
In the living room.
Memory of what happened yesterday makes his penis twitch.
Because he couldn't do anything about his situation he decided to use the pool.

The water was awesome.
He dived in and made a few laps.
As he was swimming his bare butt was popping over the water.
Two pale buttcheeks glistening under the sun.
After a few laps he decided to dive, and see how long he could hold his breath.
During his second attempt he saw someone stand on the edge of the pool.
Because of water distorsion he couldn't see clearly.
But it must be Helen or maybe her neighbor Edna.
He surfaced and as he was wiping water from his eyes he wanted to say hello.
But before he managed to do that, pain exploded in his ear.
“I GOT YOU, YOU PERV.” Angry voice said and someone was pulling him from the pool.
Milton struggled as the unknown tormentor pulled him by his ear from the water.
With water still in his eyes, he didn't see who exactly was holding him.
Based on the voice he guessed that it was a woman.
Then he saw something on her chest.
It was a name tag, no not a name tag.
It was a badge.
With name “SHARON”
“Sharon wouldn't arrest you, she would spank your bare bottom until your cheeks would be red as this towell.”
Memory flashed through Milton's mind.
“Please don't spank me.” He begged.
That seems to intrigue officer Sharon.
She slightly released Milton's ear.
“I am not going to spank you. She said with shock in her voice.
But then something changed in her expression.
“On the other hand, that is not a bad idea. Perv like you deserve a long painful spanking.”
She dragged poor Milton to the nearest beach chair.
She sat on it and put a towel over her lap, then she lowered the naked boy over it.
When Sharon saw the two cute wett globes.
She remembered how she sometimes spanked her boyfrends.
Unfortunetly her last boyfrend didn't like it.
So now, when she gets the chance to get her hands on this butt, she is going to enjoy it.
The boy in her lap was trying to stand, but she was holding him in place without a problem.

She couped his buttcheek and he froze.
“Listen you perv, I am going to spank you. Until I decided you had enough.”
With that said, she squeezed his wet buttcheek and then without a warning, she delivered the first slap.
Milton was caught off guard, still enjoying her fondling and suddenly, stinging pain exploded on his cheek.
He gasped and yelped.
Sharon didn't give him time to adjust and immediately spanked his other buttcheek.
Quickly continuing with another slap.
She was switching between his buttcheeks.
Left,right,left,right.
Thanks to the water the spanking must have felt especially painful.
But Sheron didn't care, she wanted to see that cute butt nice and red.
The yelps and sobs of the poor boy were music to her ears.
She continued the spanking for several minutes.
Until the skin had a nice deep red color. Then she stopped, resting her hand on the one of the buttcheek.
It felt incredibly warm.
At that moment the boy was just gasping and sobbing incoherently.
Sharon waited for a minute til the boy calmed.
Then she standed him up.
He was like a puppet in her hands, resigned to his fate.
His eyes were red and tears were running down.
Sharon put her hands on his hips.
He slightly jerked, when her fingers touched the side of his blistered buttcheeks.
“Shss,” she shushed him.
“Now it is over, you get what you deserve. I must say you took it like a champ.”
Sharon smiled at the boy, now when she turned his butt red and he was just a sobbing mess.
She started to pity him, she looked over his slender body.
His soft penis right in front of her face.
During the spanking she felt it was hard but it didn't last.
But it tells her the boy enjoyed the situation to some degree.
“Now you just need to stand in the corner and it will be over.”
She standed and took his hand, leading him to the house and put him in the nearest corner.
“Stand here until I tell you otherwise and hands behind your head.”
Milton obeyed, even if he wanted to touch his butt to ease pain, he feared that it would cause another spanking.
So he just stands there, his red butt facing the backyard.
He could hear officer Sharon moving somewhere behind him.

First thing Edna saw was Officer Sharon standing in Helen's back yard.
“Sharon, what are you doing here? Is Helen all right?”
“Oh, good day Edna, everything is ok. I just caught some pervert skinny dipping in Helen's pool. I take care of him”
Explained Sharon her presence to Helen's neighbor.
“A pervert?!” Asked Edna with shock in her voice.
“Yeah, but don't worry, I dealt with him. The boy will think about trespassing in our neighborhood.”
Edna looked at Sharon, confused.
“A boy?”
Sharon noded and pointed behind her.
Edna gasped when she noticed naked boy with a red butt standing in the corner.
She made a few steps closer.
“Oh my, Milton is that you?” Edna asked.
“Milton??” Wanted Sharon to know. “ You know him?”
Edna approached Milton, still obediently standing in the corner.
She gently touched his red buttcheek.
He flinched but stayed in place.
“Sharon did, did you spanked him?” Asked Edna with amusement.
“Well, he practically asked me to, and it was a good punishment for his transgression.”
Answered Sharon.
“So did you know him?” She wanted to know.
Enda looked at her.
“Yes, this is Milton, Helen's new friend. It is a long story. And I think Helen should be the one to explain it to you.”
Officer Sharon was looking at Edna with an open mount.
Slightly shocked with what she just heard.
Meantime Edna observed Milton's spanked butt.
“Damn she got you good.” She smirked.
And very gently patted his red buttcheek.
“Honey, where is Helen?”
“I don't know,” said Milton with a trembling voice.
“When I woke up, the house was empty so I just waited and went swimming to kill time.”
He explained, still facing the corner.
However Edna noticed that tension fell from his body, as she started to play with his bottom.
His shoulders slightly lowered and he moved his feet slightly apart.
“Now honey you can turn. Don't worry it is over.”
Milton slowly turned and looked at Edna.
She continued to fondle his butt.
Her warm smile makes him feel better but he still seems frightened.
“It looks like I should apologize.” Sharon said, looking at Milton.
“It's ok, you didn't know.” He said.
“Still, I need to.” Sharon started saying and then she noticed his erection. “I have an idea, I give you pain, now it's time for a pleasure.”
Milton looked at her, not sure what exactly she meant by that.
But Edna clearly did because she said.
“That's a great idea, wait here I need to grab something.”
With that she disappeared in Helen's house.
Meanwhile Sharon led Milton to the deck chair.
“Now lay here at your belly.”
She arranged a pillow in the middle of the chair.
When Milton lay over it, his butt was elevated.
The deck chair was made from stripes of fabric, with gaps between them.
His penis and balls fell into one of these gaps.
If someone would look under the chair, he would see one hard throbbing penis pointing to the ground.

Edna comes back with some dose in her hand.
“This cream will help with that sore butt.” She said and kneeled next to the deck chair.
Sharon was kneeling on the opposite site.
Both women applied globs of the cream on their palms and then they started to apply it on Milton's butt.
He flinched when the cream first touched his skin.
But immediately he felt a nice cold sensation on his spanked butt.
As the soft palms smeared the cream over his buttocks.
“Mmmm.”
He moaned and closed his eyes.
Sharon and Edna looked at each other and smiled.
Then they continued massaging Milton's butt.
Sharon tried to move her fingers between his tights.
To her surprise, Milton put his legs apart to allow her better access.
She put the cream over his asshole.
He clenched his buttcheek when cold cream touched him there.
Edna gently patted his buttcheek and quietly said.
“Shhh, it's alright honey, just enjoy it.”
And continued applying the cream.
When he opened his legs, Sharon noticed his penis was in the gap between two fabric stripes.
She reached under the chair and carefully enveloped his throbbing penis.
Which caused Milton to moan again.
But he stayed laying, enjoying the attention.
As Edna played with his butt, fondling, squeezing and patting it.
Sharon started to masturbate him.
It didn't take long for Milton to start leaking precum.
Sharon continued.
“That's it,” she said, “ these hands can bring pain but they can bring pleasure too.”
Milton was lost in it, and soon he clenched his cheeks and cum into Sharon palm.
“That's a good boy,” she cooed as she felt his seme in her hand.
Edna fondled his butt watching it flexing.
“Yes, cum for us, like a good boy.” She whispered.

When Helen came home, she found both women sitting on her deck chair.
Watching Milton sleeping.
When she saw his red butt she looked at the two women.
“Long story, explain later.” Sharon quietly said.
Helen joined them and three of them watched one cute naked boy with a freshly spanked butt, sleeping near them.

[Trundle]

Great to see another chapter.

Poor Milton getting spanked !

I like how Milton seems to be constantly going from being punished and humiliated by the women to being jerked off in very pleasurable ways by the women. He never knows what is going to happen, it's from one extreme to the other so he's always unsure and unbalanced. I love it.

Can't wait for more.

[Qwerto1232]

Thanks for the comment, I am glad you like the story.
I have planed two more chapters. In the next chapter Emily finaly be back. Chapter 10 will be last for this story arc.
I have some idea for the second arc when milton starts working in his new job. And he finds out he is the only man in the office. Which brings som interesting situation. But after chapter 10 there will be longer pause. I will be working on my other stories.

[Qwerto1232]

Part.9

Officer Sharon needed to return to service.
She quickly say her goodbyes with Helen and Edna, and left.
But before that she very gently patted the naked butt of sleeping Milton.
He slightly jerked under her touch but continued sleeping.
His freshly spanked buttcheek was stil sensitive.
“We should put some sunscreen on that poor boy. Otherwise his butt won't be the only red thing.”
Advised Edna.
Helen nodded and brought the sunscreen.
Both women again kneeled next to a beach chair, and slowly started massaging the cream into Milton's back.
Soft moans escaped his lips, clearly enjoying their touch even sleeping.
Helen worked on his shoulders moving down.
Enda started on his calf and moved up.
Soon both women reached his butt.
But they avoided direct contact with the red skin.
“Helen?” Milton asked, and opened his eyes.
“Shhh, I am here lamb.” Henel assured him and put her hand gently on his buttcheek.
Edna stand up.
“I let you two alone.”
She said, kissed Milton on his forehead and left.
Milton wanted to stand up, but Helen didn't allow it.
So he just turned his head.
“Honey, are you all right?”
Helen asked with gentle concern in her voice.
And put her hand on Milton's red buttcheek.
“Yeah, it didn't hurt anymore.” He said thinking that she is asking about the spanking.
Helen smiled.
“No, I mean, about this. What are we doing together? Everything that has happened since the cinema.”
Milton looked as if he was thinking about it.
Helen waited and meantime fondled his butt.
“It's ok.” He said.
“You know you can end this if you don't like it.”
Helen assured him.
“I like it,” Milton almost whispered.
Helen's hand on his butt started to have an effect on him.
He moved his hips to better position his hardening penis.
Helen smirked when his butt flexed under her palm.
“Some things are embarrassing and sometimes I am frightened. But i like it too.” He confessed.
“That's great.” Helen said with glee.
“I wouldn't want to lose this cute bottom” And she gently slapped him.
“Now, I know how deliciously it looks spanked. I think I need to start spanking you.”
Milton's frightening look was priceless.

Rest of the day was pretty boring. They ordered food and watched some movies.
Milton laying on his belly on the couch.
His head on the cushion in Helen's lap.
During the movie she played with his hair and his butt.

Next morning, Helen woke up to the smell of an omelet.
She came down into the kitchen and there she saw Milton.
He was standing there preparing breakfast.
His naked butt still slightly red.
Helen stood there watching him, his buttcheek flexed as he moved his weight from one foot to another.
Slightly swinging his hips, as he was dancing to some tone only he heard.
Helen was mesmerized by his naked body.
But her stomach reminded her she is actually hungry.
Helen stepped closer to Milton and hugged him from behind, one hand gently squeezed his buttcheek.
“Hmm, making breakfast. Someone is trying to be a good boy.” She chuckled.
Milton looked up to her and smile.
“Maybe I really should spank you regularly.” she teased him.
“If you think it is necessary.” He meekly said.
She squeezed his cheek again and went to sit behind the table.
Waiting for him to serve her.
During the meal Helen let him stand next to her and played with his penis.
Making him hard but not making him cum.

After breakfast, Helen needed to go take some earands.
“I will be back in the evening. Will you be ok.” She asked.
“Yeah, I could watch TV or swim again.”
“It's a nice day to be inside, there is a nice park nearby. You could go there to stretch your legs.”
Helen proposed.
“I can't go outside, I am naked.” Milton said with slight panic in his voice.
Helen smiled and hugged him.
“Oh don't worry my lamb.” She said and again fondled his butt.
“I would not send you out in your birthday suit.” She assured him.
“Not yet anyhow.” She added with a mischievous smile.
“I left you some clothes on the bed.”
She said, last time squeezed his cheeks and left.

Milton walked to the guest room, hoping she left him some normal clothes.
But he knew what he would find there.
And as he expected, on the bed layed a stretched shirt.
When he put it on, he realized that he was naked for almost two days.
He checked himself in the mirror, everything was covered as usual.
So if he doesn't make sudden movements or raise his hands up, he should be ok.
Past few days he has become proficient in wearing so little.

The park was pretty close to Helen's house, one may say it was an extension to her backyard.
Milton was glad he didn't need to walk a great distance.
Mainly because the only shoes he found were flip-flops.
When he entered the park, the nervousness he felt disappeared.
Only person he could see so far, was some jogger on the opposite side of the park.
And even him looked like he was leaving.
Milton watched as the jogger disappeared between the trees.
Then he looked around.
In the middle of the park there was a big grass area with picnic tables.
Around the area led the path, he could see several crossroads and smaller paths disappearing in the forest.
Before he could decide where he wanted to go.
Someone behind him said his name.
“Milton is that you?” The girl's voice asked.
Milton, shocked by hearing his name, slowly turned around.
Few steps from him stood a girl, she looked vaguely familiar, but he couldn't remember where he saw her.
She looked almost like Gwen Stacy from Miles Morales Spider-man.
She even had the same haircut.
Right now she was wearing a tank-top, short shorts, on back she had a small backpack.
“Emily, cashier from the cinema.” The girl introduced herself when she saw that Milton couldn't remember her.
“Oh, sorry I didn't recognize you without your uniform.” Milton managed to say, and subconsciously gripped the hem of his shirt.
Emily smiled and waved her hand.
“That's ok, I see you are wearing your uniform.” She said with a smirk.
“M My uniform?” Asked Milton with confusion.
“Yeah, that long stretched shirt.” Emily pointed at his shirt.
“Yeah,” was the only thing Milton managed to say and then he laughed awkwardly.
Emily stepped closer to him.
“So what are you doing?” She asked.
“Nothing, just want to go for a walk.”
“Wana company?” Emily asked.
“I know it here, I can show you the best spots. Where no one will see us.”
She added.
Milton looked more confused than before.
Trying to process why she wants to go with him somewhere private.
Before he managed to say something, Emily took him under the arm and started walking.
He had no choice just to walk next to her.
As they proceed through the park, Emily casually questions him.
How is he doing? How is Helen? What are his plans for the next few days?
Milton is answering her questions as he tries to act normally
Which is not that easy, when the only thing he is wearing is the long shirt and pair of flip-flops.
Suddenly Moly stops.
“Here it is,” she says and pointed to a small path leading into a hill.
“It leads into a perfect hiding spot. You can see the whole park from there. But no one can see you.”
She winked at him and started to walk on the path.
Milton is trying to follow her, but the flip-flops aren't exactly hiking boots.
Even Emily noticed his troubles.
“How about you take them off.”
Milton looks at her with fear in his face.
“Took what off?” He asks with panic and strongly grips the hem of his shirt.
Emily noticed it but doesn't comment on it.
Instead she says “Your shoes, you can't climb this hill in flip-flops. Better to go barefoot.”
When she sees his hesitation she adds.
“Don't worry it is mostly grass. You will be fine.”
Milton gulped and without a word he took his shoes off.
Emily observes him as he takes them from the ground.
Looking where to put them.
“Let me..”
She said and took the flip-flops from Milton's hands.
He watched with concern as they disappeared in Emily's backpack.
“Let's go.” She says with glee and continues walking.
Milton obediently follows her.
When they reach the beginning of the spot where the path starts to ascend.
Emily stops.
“After you,” Milton said, “Ladies first.”
He tries to act as a gentleman.
But in reality, he tries to avoid going first. Because in that case it would be impossible for him to conceal his lack of pants and underwear.
Emily giggles.
“You are saying that just so you can ogle my butt.”
She accused him.
Milton started to blabing.
“No I don't want to, it's just if you fall.. can catch you.”
“So you are saying my butt is ugly? Not even worth one look.”
Emily hissed.
Milton doesn't know how to react.
But is saved by Emily's laugh.
“Chill dude, I'm just messing with you.”
She said and started to climb the path.
Milton watches her make a few steps.
His eyes instantly point on her butt.
He gulped, and looked down.
Last thing he needs now is an erection caused by the flexing butt in front of him.
The ascent wasen too difficult, Milton easily followed Emily to the top.
Emily made the last step and stood there. She quickly looked around and then down at Milton.
She then reached with her hand to help him make the last step.
Milton reluctantly took her hand, and with his other he tried to tug the hem of his shirt down.
He knew that when Emily would pull his hand his shirt would go up.
Revealing his lack of underwear.
So he tried to hold it down.
Even if that meant to stretch the collar of the shirt almost to his midriff.
“Here you go,” Emily said and pulled him up.
He made the last step, as she was pulling him, Emily took one step back.
Forcing Milton to follow.
He made one step too, but he calculated it wrong and ended in Emily's embrace.
“Wow,” she said, slightly surprised.
But before he could react she hugged him.
Milton felt her hands on his back.
He didn't know what to do so he just waited.
His hands on his side.
Emily continued hugging him.
He wanted to say something but she interrupted him, and whispered to his ear.
“Btw, I know you are naked under this shirt.”
Milton's heart skipped the beat. He froze not knowing how to react.
After a few seconds of awkward silence he managed to say with a forced smile.
“Everyone is naked under their clothes.”
Emily continued hugging him, and whispered again.
“I mean, this old, long, stretched shirt is the only piece of clothing you have right now.”
“Don't be ridiculous,” tried Milton.
“I am wearing shorts, they are just realy short.”
“Right,” said Emily,
”So if I do this.” She moved her hands on his butt, still covered by the shirt.
“And then this,” she continued. And before Milton could react her hands disappeared under his shirt. And landed on his naked buttcheeks.
He gasped and Emily laughed.
“As I say.”
She squeezed his buttcheeks and let him go.
She took a step back and took his hands into hers.
Not allowing him to cover.
Milton was looking down, not capable of looking her into eyes.
“So why are you running around wearing only a shirt?” She asked.
Milton didn't answer.
“Come on, you can tell me.” She begged.
“Please.”
Milton looked up and their eyes met.
“It's a long story.” He try to avoid it.
“I have time,” Emily said.
“Can we go elsewhere? This is not exactly a good spot for a talk.”
Milton said with defeat in his voice.
Emily led him deeper on the path.
In the end of it was a small clearing between the trees.
They could see a whole park from there.
It was a really nice view.
“Start talking.”
Emily commanded after she sat on a log laying on the ground.
Milton carefully sat next to her and started to tell her what happened since he fell in the cinema.
Obviously he left out some details, especially that spanking he got from Officer Sharon.
“Wow, that sounds awesome and kinky.”
Reacted Emily, when he finished talking.
“Damn Helen is lucky. I would like to have a boy toy.”
She added and caused Milton to blush.
“Can I?” Emily asked unusually quietly.
“Can you what?” didn't understand Milton.
“Can I take your shirt off?” She asked with hope in her voice.
When she saw he was not answering she said.
“Come on, it's not like you weren't naked in front of women. And from what you told me, you clearly like it.”
Milton looked at her not knowing what to say.
Emily stood up, looked at him and gestured to him to stand too.
When he was standing Emily commanded.
“Hands up!”
He obeyed and when he put his hands over his head.
He could feel the hem of the shirt to slightly rise.
Revealing tip of his penis.
Emily took the hem of his shirt into her grasp and looking into Milton's eyes she started to lift it up.
Agonizingly slowly.
Without breaking eye contact she raised his shirt to his neck.
And then with one quick motion she took it off.
Milton instinctively covered his crotch.
Looking at Emily as she was putting his shirt into her backpack.
Again, Milton found himself at the mercy of a woman, he met just a few moments ago.
She had all his clothes and could make him do whatever she wanted.
He was naked, trapped and helpless in public.
So why was his penis starting to rise?

When Emily took care of his shirt it was safely hidden outside of his reach.
She looked at the naked man in front of her.
Nice body, nothing extremely muscular but still she could see some abs.
She smiled when she saw how he was trying to hide his penis.
She decided not to spook him so she let him cover himself.
“Turn over.” Emily commanded, and with glee watched as Milton obeyed.
It felt so powerful, he had no choice but to listen to her.
Milton facing away from Emily.
Desperately tried to keep his throbbing erection under control.
Which was a lost fight from the start.
Meantime Emily was looking at his butt.
“Damn that is a gorgeous butt.” she thought and bit her lip.
She wanted to touch it again, without hesitation she made step closer and gently couped Milton's left buttcheek.
She felt how he trembled, but made no attempt to stop her.
She gently squeezed and fondled it.
Quiet moan escaped Milton's lips.
Emily chuckled, he was clearly enjoying it.
Then Emily noticed something odd.
Milton's butt was more red in comparison to the rest of his pale body.
“No way.” Emily thought and leaned closer to Milton's ear.
“Milton, why is your butt red?” She asked.
Still fondling his buttcheek.
Not waiting for his answer she continued.
“Wear you a naughty boy and get spanked?”
Emily asked, barely suppressing a laugh.
Milton shaked his head.
“Really? Because from where I stand. It looks like your cute bottom was spanked.”
And as to emphasize her words she slapped him.
“So wanna try to answer again?”
Milton noded.
“I thought so. What happened?”
Milton quickly summarized his interaction with Officer Sharon.
“Wow, that must be a view, you, standing naked in the corner. Like a naughty little boy. These cheeks red as Rudolph nose. I bet they were nice and warm after that.”
Emily said and squeezed his buttcheek again.
With one hand playing with his butt, she moved her other hand to his belly.
“Hands behind your head.” She commanded and Milton obeyed.
Then she moved her hand down.
Until she felt his erect penis.
Milton shivers when her fingers graze his throbbing shaft.
Another moan escaped his lips.
“Someone likes to be naked outside.” Emili whispered to his ear and patted his butt.
Before he could react, her hand enveloped his erection and squeezed.
“Aahh..”
“God, you are hard. I bet you would like me to jerk you off.”
Emily said and moved her hand up and down.
Milton noded and Emily continued stroking him.
After a few slow storks, she cupped his balls.
“Nice.”
And continued with storking.
Milton started to breathe heavily and pushed his hips front and back.
His senses started to overload.
He grunted and speeded his pelvis movements.
In reaction Emily started to spanking him.
SLAP
Her palm landed on his left cheek, squeezed it and then.
SLAP
Landed on the right and again
SLAP on the left.
As she spanked him, she felt his precum leaking from his mushroom.
She started to jerk him faster.
And when she delivered another slap on his butt, he came.
Streams of cum floated into the grass.
One, two, three.
After the last spank, Emily left her hand on his buttcheek.
Gently couped it and massaging it.
“That's a good boy, cum for me.”
With her other hand Emily continues to milk every last drop of his cum.
“That was awesome. “ she cheered him.
Milton just gulped, he was so drained he couldn't even speak right now.
“Thank you.” Emily said after a few seconds and hugged him.
Her hands returned to his butt cupping and squeezing it.
With one hand she dragged her fingers over his back, from his butt to his neck.
Milton shivers.
Emily grabbed his neck and kissed him.

Then she led him back from where they came.
Milton was really anxious as they walked through the forest path.
He was still naked, and jumping with every sound from the forest.
Emily watched his nervousness with a smile.
When they emerged from the forest, Milton noticed they stood exactly where he entered the park.
“Unfortunately I need to go now.” Emily started.
“But we definitely need to meet again. Give me your number.”
After he did, she started walking away from him.
“Wait!!” Milton shouted.
“Yes?” Emily asked innocently.
“I need my shirt back.”
“No you don't. I am still a little mad at you for lying to me about that spanking. So as a punishment you will go back to Helen naked. From what you told me it is not far. So you probably won't be seen by anyone.”
Milton makes one step closer to Emily.
“I wouldn't do that,” She warned him. “I am a pretty good runner. And the last thing you want to do while naked is chasing a woman in a public park.”
He froze in place, as he realized his situation.
“So be a good boy and do as told. I can see you like that idea of streaking. You are hard again.”
Milton looked down at his hard penis.
Then he turned around and started running.
Emily quickly snapped a photo of his back and then watched with a big smile as his red butt disappeared in the distance.

[Jeepman89]

Great chapter. Love that he is totally naked and stranded on his own in public.