Simple Submission

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Her neighbor wants to be submissive while wearing a dress.
3.3k words
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Heidi had a good life here in Southern California. At the age of forty-three, she had a good job and a lovely house. Living in the city of Arcadia was almost the equivalent of an island paradise. She had friendly neighbors who reminded her why she stayed in such a quiet and clean suburban community. They were good people, the kind that never overstayed their welcome or caused any interruptions. One of them was the one who lived next door.

She had met Oscar approximately one year ago. She had grown to admire the eighteen-year-old man as a kind and sociable individual. He was handsome with his blond hair and overall skinny figure. Since Heidi was tall, Oscar was just a few inches shorter than her. But the two of them didn't mind it at all. Their friendship became more important. Since their introductions, their small talk slowly led to casual conversations. They grew to admire each other. Heidi would grow fascinated with Oscar's ambition, his search for fame as an aspiring writer taking the top spot on his checklist. Oscar, on the other hand, couldn't help but respect Heidi's success as a bank branch manager, leading to a great reputation on her part. Their friendship would never seem to end.

On a calm and cool Friday night, Heidi relaxed in her living room and began to read a book by the window. She had a clear view of not only the house form across the street, but also the distant foothills of the San Gabriel Mountains on the left. The moonlit sky made for an excellent mood as Heidi continued to read a book from one of her favorite authors.

The doorbell rang. She placed her bookmark between two pages and went to see who was at the front door. She smiled when she saw Oscar standing on the front porch. He had a skateboard in one hand and a flat rectangular box in the other.

Heidi asked, "What's going on?"

Oscar briefly gazed at his house next door. "Listen, I just arrived from the mall and my parents are at home. Can you please put this somewhere safe? I'll come back tomorrow morning and retrieve it."

Heidi felt suspicious. "What is it? What's in the box?"

"Oh, it's nothing. It's just something that I bought at one of the stores."

Heidi chuckled. "Can you be a little more specific?"

"It's just clothes."

"Why would you want to hide it from your parents?"

"It's...a little complicated. Just put in it somewhere safe. I'll see you again in the morning."

He handed the box to her and gave her a little smile before leaving. Heidi didn't know what to say, but she followed his instructions. She trusted him enough to not feel convinced that something disturbing lay inside the box.

She went into her bedroom, but before she could put the box in the closet, she just had a thought. She had never seen Oscar give off a little hint of mischief before. His current behavior made her want to see what lurked inside. At first, she tried to suppress her temptation as she wanted to respect Oscar's wishes. But then again, she needed to see why he would do such a thing.

Instead, she sat on her bed and placed the box on her lap. She opened the top and immediately froze as soon as she noticed the dark green dress from inside. Her curiosity had been followed by a mystified effect. She picked up the dress and had a good look at it. She examined it from top to bottom. The green dress included a halter neckline and a skirt that could have ended at the knees.

This became a mystery that proved to be quite difficult to solve. Heidi began to feel confused as to why Oscar would purchase something like this for his personal self. The only reason would have to be that he bought this for his girlfriend. Then again, he always mentioned that he didn't have one. Perhaps he bought it for his mother as a gift. Or perhaps, he bought it for himself.

Heidi's jaw almost dropped at the thought of the last possible motive. She wouldn't think of her young neighbor as someone who would want to wear a dress in secret. He wouldn't have kept a bit of his own information from her unless he absolutely had to. Heidi put the dress back in the box and closed it. She put it in the closet and kept it safe. She would need a definitive answer from Oscar. She would think about this new image all night, but at least she would discover the truth in the morning.

* * *

Saturday morning started with a cup of coffee in the kitchen. The clock on the wall read 8:12 AM. She waited for Oscar to ring the doorbell. She had placed the box on the graphite countertop. She kept her eyes on it. She always trusted Oscar, and she would never dare to believe that he would conceal some sort of dark side to his own persona. She only hoped that there would be no malicious intent for something like this. She almost laughed. Of course, no one would get hurt. It would be too silly for Oscar to behave in such a negative manner.

The doorbell rang. Heidi put her cup down and left the kitchen with the box in her hand. She opened the front door and smiled at Oscar who did the same for her.

She showed him the box. "I put it somewhere safe, just like you told me."

Oscar nodded. "Thanks a lot."

Heidi suddenly pulled it away from him before he could even touch it. "But let's have a little talk first."

Oscar didn't flinch. "Okay, whatever you say."

She led him into the living room and the two of them took a seat on her sofa. She asked him, "So why did you want me to hide this in the first place?"

Oscar had a little smile on his face. "Are you sure you want to know?"

That just made Heidi even more curious than before. "Yes, I do want to know."

Oscar had his eyes on the box. "You looked inside, didn't you?"

"Yes, I did. And it shocked me at first. I kept wondering why you bought a dress and wanted me to hide it. I thought it was a gift for someone. But then...I started to wonder if you bought it for yourself."

Oscar chuckled as he brushed his fingers across his blond hair. "Well, you caught me."

"So it's true?"

Oscar grabbed the box and opened it. He looked inside and started caressing the dark green dress with slow and careful fingers. "You can just see this as my confession. I bought this for myself. I wanted to wear it. I've been wanting to since Christmas."

"But why?"

Oscar looked at her like a sly scalawag. "Because I want to know how it feels to submit. I want to know how to take it like a sissy."

"That sounds rather fascinating."

Oscar lifted the dress from out of the box. "This is a secret dream. A dream that I hope will come true someday."

Heidi only had one thing in mind. "I'd like to see you in it."

Oscar's smile grew larger. "With pleasure."

* * *

In her bedroom, Heidi watched as her young neighbor took off his clothes and put on the dress. He was careful with it, having it slide on his body in a slow and stable manner. He straightened out the fabric with his fingers before standing in front of Heidi.

"So how do I look?"

Heidi was enthralled. Oscar had somehow exchanged his original appearance with a more feminine appeal. The quick transition seemed flawless. The green dress fit him perfectly. His hairless legs were the perfect match for the skirt. The halter neckline didn't bother him at all.

Heidi couldn't help but feel so proud of Oscar's achievement. "Oh, it looks amazing on you."

Oscar made a complete 360-degree turn to give Heidi a complete look at his new exterior. The way he swirled around made the skirt soar in the air.

"It feels so good on me. I'm glad I made the purchase."

Heidi noticed that Oscar's tone of voice grew a little more womanly. The dress started to take possession of his state of mind and added a few new ingredients for his intended ways.

Heidi asked, "Isn't it nice to look like you're ready to submit?"

Oscar giggled more like a girl. "Oh, yeah. I'm loving it."

Heidi rubbed her chin. "But there's one more thing. You need a mate to complete this transition."

"Oh, you're right."

"But you know what? I think I'm to choose who it is."

"Really?"

Heidi pulled out her smartphone from her pocket. "You know Keith from across the street?"

Oscar nodded. "I've seen him before. He goes to my school. We take two classes together."

"That's good, because I hope he's in the mood to see the different side of you."

She called Keith's phone number and waited for him to pick up. When he did, she asked him if he could come over as soon as possible. Keith told her that he would arrive in a few minutes.

* * *

She led him into the living room and showed her the new and improved Oscar. Keith, a brown-haired eighteen-year-old skater, didn't look too shocked at this new image. Instead, he slowly licked his lips and whispered, "Where have you been all my life?"

Oscar giggled as he showed off his green dress. He stood on his bare feet as he twirled around the same way he did in front of Heidi just a short time ago. "Do you like it better when I'm like this?"

"Oh, of course. You should be like this more often."

Heidi sat on the recliner. "Why don't you stay here for a while? I'm teaching Oscar how to be a complete sissy?"

Keith raised an eyebrow. "Is that so?"

Oscar stepped closer toward him. "You see, I really want to submit to another man while I wear this. I want to know how it feels to be nothing more than a servant."

Keith chuckled. "You really look like you could be."

Oscar looked down at Keith's jeans. He continued on with his girly tone of voice. "Oh, I really want to see it."

Keith didn't waste any time as he unzipped his jeans and pulled out his cock. It had already grown erect thanks to the inspiring image of a classmate in a dress.

Oscar moaned. "Oh, yours looks really good."

Heidi leaned forward and stayed attentive to what transpired in her own home. "Try to be more seductive. Show him that you're willing to be used by him."

Oscar giggled. "I want that cock, Keith. I want it inside me. I want you to control me, make me your personal servant and have me do what you tell me to."

Keith pulled down his jeans and boxer shorts and kicked them away. "I really hope you stay this way as I put this deep inside you."

Oscar moaned. "Oh, I can't wait."

He got down on his knees and grabbed Keith's dick with his hand. "Oh, I want it on me. I want to feel it on my skin."

He began to stroke Keith's cock with his slow fingers. The erection remained the same, but Keith's demeanor grew just a little more antagonistic.

He whispered, "Yeah, point it right at your face. You're gonna feel it and you'll like it."

Oscar trembled with a girly attitude. "Oh, yes."

Heidi was silent as she watched her young neighbor begin the stage of his new ambition. His fingers accelerated as he kept the shaft pointed at his face.

Then she proclaimed, "Don't stop, Oscar. Be who you are destined to be and let it happen."

This time, Oscar grabbed the cock with both hands. He stroked it hard while never giving any hint of an abrupt halt to his continuous action. "Oh, I want to feel it."

Keith kept grinning. "You're my bitch, and that's all that matters."

Oscar licked the tip of the cock and smiled like a slutty servant. "Your dick tastes good."

Heidi giggled at the sight of her neighbor being naughty in front of her. "That's the spirit, Oscar. Keep showing him that you care."

Oscar's fingers picked up speed and now had Keith's erection moving on to its boiling point. The young man in the dress began to take quicker breaths amidst the tension growing from within. He licked the tip of Keith's cock once more.

"Oh, I want it so bad."

He continued to use a more feminine tone of voice, and it suited the situation very well. Heidi held her breath, eagerly awaiting the ejaculation caused by Oscar's submission.

Keith growled. "You're nothing but a sissy."

Oscar laughed. "That's right. I am nothing but a fucking sissy."

All of a sudden, Keith's semen made its presence known. His cock ejected huge spurts of it. They landed right on Oscar's face, neck, and chest. Scattered stains had just been formed on the green dress. Oscar let go of the cock and looked down at the mess he made.

He couldn't help but giggle like a young and naughty woman who found herself being used by her mate. "It feels really good on my dress. It feels even better on my skin."

He licked up a little residue that stuck to his upper chin. "It's warm. I love it."

Heidi was mesmerized by Oscar's new appearance. Outside of this house, he would be an ordinary eighteen-year-old skater without a care in the world. But inside this house, he had become something that she never expected to see. And she wanted to see more of it. Just the sight of her young friend being so submissive to another man made her tingle with excitement. She realized that she got a kick out of seeing him as a sissy in a dress. She currently had no regrets when letting Oscar be whoever he wanted to be in this house.

Keith's erection didn't shrink just yet. "I think you want a little more of it. Isn't that true?"

Oscar didn't wipe away the juices on his skin and dress. "Yes, I want more of it on me."

"How about INSIDE you?"

Keith took off his shirt, revealing his healthy physical state. It certainly made Oscar sigh with anticipation.

Keith took a seat on the sofa. "Go ahead. Put it inside you."

"With pleasure."

Oscar stood up from the ground and had his back turned on Keith. He lifted up his skirt and lowered himself down. His ass was right above Keith's upright cock. He took his time seating himself right on Keith's lap. Heidi watched as the cock slid right inside his hole. It made Oscar squeal. Keith stayed put as Oscar now had his ass prodded by the cock that he played with.

"Oh, shit! It's in my ass."

Heidi replied, "Don't be afraid. Just embrace it and you'll be the right kind of sissy to your classmate."

Oscar moaned. "I will."

He moved his hips up and down the cock. He kept his dress on as he made his next move. He slide in and out of the cock that seeped right through his narrow inner passage. It was the perfect sentient instrument that stimulated his senses. He moaned like a woman and squeezed his eyes shut.

"Oh, I fucking love it."

Heidi leaned forward. "It certainly makes you crave more, doesn't it?"

Oscar whined for a brief moment. "I'm glad that I submit."

Keith chuckled. "I know that I like you better this way. You're my bitch now. I wish I could see how well you're handling it."

Oscar ad his mouth wide open amidst the pain and pleasure wrapped into one electrifying experience. He moved his hips quicker than before. He bounced up and down with glee.

Keith growled. "I think you're a pro."

Heidi laughed. "Believe it or not, this is his first time."

"He's already an expert."

Keith jumped up from the couch and stood up. He bent Oscar over above the coffee table and grabbed his hips. Still asserting dominance, he pushed his cock deep inside Oscar with quick speed. Oscar had to press his hands on the table's surface in order to keep his balance. His blond hair danced in the air as he moved to the rhythm of Keith's aggressive pounding.

"Oh, fuck me hard! I'm yours!"

Keith started to grab Oscar's hair and pull it. "You like that, don't you?"

Oscar moaned loudly. "Do it to me! Don't stop fucking me!"

Keith's hips and Oscar's buttocks collided with each other, and the smacking sound echoed all across the living room. Heidi just sat in her recliner and observed the simple submission that her neighbor had sought for. She was quite entertained by this new side of him. She had nothing but joy for his obedient behavior when having a cock deep inside him. With all that semen on his skin and dress, this riveting scenario seemed to fit his new persona. It thrilled her to see her younger friend become a submissive servant who was ready to consume everything aimed at his direction. She smiled. Oscar's new personality benefited both him and her. She wanted to see more of him acting the same way in the future. She wanted to see him continue his sissy ways with other young men. She hoped he would accept a new idea that just formed in her mind.

Oscar yelled, "I'm so fucking hot for you!"

Keith didn't stop thrusting his cock deep inside Oscar's ass. Oscar's whole body shook to the tune of Keith's powerful momentum. He continued to use his girly tone of voice, which was a clear indication of his true feelings. He never attempted an escape, which made it a little more pleasing for Keith.

"Here it comes. You're going to get some more of my load."

Oscar squealed during every thrust and almost had trouble speaking. "Give it all to me!"

Heidi sat up straight and waited for the second explosion to occur inside Oscar's walls. Oscar moaned the loudest when it happened.

"Oh, fuck!"

Keith shoved his cock deep inside Oscar's ass when the eruption became unstoppable. Oscar trembled at such force as he almost fell on top of the coffee table. Heidi sighed as the visual presentation of Oscar's wicked ways had been complete.

Keith pulled his cock from out of Oscar's expanded hole. His thick cum spilled right out of it and landed on the floor. Heidi didn't mind it. She had her sights on Oscar, who appeared to be delighted at the result of his dream coming true.

He straightened up and gazed at the small puddle of semen that had been formed on the floor. "This is what I wanted for a long time."

His tone of voice didn't change. He kept on clinging to his new personality.

Heidi stood up from the recliner. "You are looking to be the best in the business."

Oscar smiled. "I like the sound of that."

Heidi kissed him on the forehead. "You're right. I don't think your parents should know about this. They'll try to get rid of our special relationship if they did."

"I hope Keith gets to visit again in this house."

Keith put his shirt back on. "I'm lucky to have seen you like this."

Heidi raised a finger. "But it's not going to end there. Oscar, I love it when you're a sissy. So don't worry. There will be other men in your life. I'll personally select them and have them meet you here in my place. I'll even but another dress for you. I'll be in charge of your fun time. You submit and I'll watch the whole thing. It'll be our precious little secret."

Oscar giggled. "I can't wait for the next one."

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4 Comments
cdCindy1cdCindy1almost 3 years ago

Please tell us more. Please continue this story. I want to be like Oscar (he needs to be given a feminine name). I can't wait to find out how Mistress Heidi will control Oscar's femininity and sissiness.

cdCindy1cdCindy1almost 3 years ago

Love this story. I too want to submit to the control of a mistress, who will feed me big juicy cocks and watch me getting fucked by hot sexy men.

I can't wait.

AnonymousAnonymousover 3 years ago
Woman Mistress

Oscar is so lucky to have found some one to help him become who is...."I love pan ties"

AnonymousAnonymousover 4 years ago

Mmm loved this story, it sounds like heaven having a woman supervise the dressing and selecting the lovers, a perfect sissy life. I wish it was me, giggle. Please write again soon. X sissy Lucy

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