Benjamin was 24 years man living with his mother. He had lost his job, so he couldn't afford to live on his own for now. One day his mother came back home earlier than usual.
"Where's lunch, Benjamin? I have my friend coming over."
"It's not ready yet, mother. I thought you are coming back in an hour."
"I did text you a message, though. You are living under my roof, jobless, and you can't make lunch on time. Are you looking for a job at all?" mother was angry.
Benjamin said nothing. He has been looking for a job for a month now but it was not easy to be found. He came to the kitchen and started preparing the food. He heard the doorbell ringing. Mother said "hi" to her friend. He recognized Isabella's deep-sounding low voice. She was the usual guest of his mother.
Isabella was 40 years old but a very beautiful woman. She had vivid red hair, it was curly and short. Hair perfectly matched her personality, she had a lot of energy and always had many radiant ideas.
Benjamin caught a glimpse of Isabella through the kitchen door. He's always found her sexy in some way. He loved the view of her red hair shining in the sunlight, her deep voice, and her laugh.
Lunch was prepared and served on the table. Benjamin's mom complained about him being jobless. It was humiliating, he didn't want Isabella to know every little detail about him being unemployed. It was humiliating.
"If you need a little gig until you find a job, Benjamin, I need someone to clean my garage. I was thinking of hiring someone from a cleaning company but since you don't have a job, I believe you could clean it as well," Isabella offered.
"You are so generous! Benjamin would be happy to help you, right?" said Benjamin's mother.
Benjamin nodded his head. "Garage cleaning is not so bad," he thought.
After lunch and a dessert, Isabella was about to go home.
"Why don't you go with Isabella today? It's not like you have anything else to do," said the mother.
"Sure, I guess I could go today."
"Perfect!" Isabella didn't hide her joy.
"You must do what Isabella says," said Benjamin's mother.
Isabella was living nearby, just a couple of blocks away. They didn't talk much while they were walking. Finally, Isabella's home was reached. They went straight to the garage. He was supposed to clean it but it was already tidy.
"Isabella, I don't understand."
"Well, don't act so surprised. It's not about my garage. Remember the last time you were here?"
"Yes..." he remembered they were here with his mother two weeks ago.
"Well. You have nothing to say? Nothing to admit?"
Benjamin was thinking. Last time while Isabella and his mother were having tea, he went to the toilet and noticed Isabella's bedroom door open. The drawer was open and he had noticed some red laces, so, he had to check. The drawer was full of sexy underwear. He has never seen so much underwear in one place, he touched most of them to feel the fabric. He had no idea he was watched.
"So... you have nothing to say?"
"I'm sorry, I didn't mean to offend you, Isabella. They looked so sexy, I had to touch them. Please, don't tell my mom."
"Don't worry, if you do as I say I won't be telling your mother."
Benjamin was relieved. He couldn't afford to make his mother angrier than she is. He was living in her house, he had to follow the rules.
"Anyway, you cannot be unpunished, right? I think it's only fair if now I will see your underwear, isn't it?"
Benjamin didn't know how to react. "No way she's seeing me in my undies," he thought.
"Well, what are you waiting for? Do I have to call your mother and tell her how you smelled my lingerie?"
"No, please don't call my mother. She will make me move out."
"So.. chop-chop!"
Benjamin started undressing. He removed all his clothes until he was in his underwear. Truth to be told he'd always saw Isabella as an attractive woman, despite the fact she was a friend of his mom! He couldn't believe he was only in briefs in front of her. It was something sexy about it and it made him feel the arousal. He's always found strong and controlling women sexy. Being dominated in bed always awakened his imagination.
It wasn't a surprise Isabella's controlling voice made all his blood rush to his cock. As his cock was getting harder, he tried to hide it with his hands and blushed a little. He had no intention to let Isabella see his temptation.
"Well well well... What do we have here? Don't be so shy, it's not something I haven't seen," said Isabella. "Stand straight and put your hands to your sides."
"But I don't want you to see me like that, Isabella."
"First, from this moment I am not Isabella to you. You must only call me mistress. Second, you don't have a choice because I will tell your mom you were looking through my panties like a dirty boy you are."
Benjamin felt his cock is already hard, there's no way back now. He removed his hands.
"Wait... Benjamin, is it getting bigger? Did it just throb? Wow... you really can't handle yourself, can you?"
He had always found her voice intimidating. The fact she was humiliating him, turned him on even more.
"If you think I'm going to touch you, you're mistaken," said Isabella. "You're a big boy, you can take care of yourself! Lay down on the bed."
Benjamin obeyed. He had always been dreaming about a dominant woman, so, he didn't want to miss a chance of exploring this fantasy. In addition, he knew Isabella will tell his mom about the panties' drawer if he won't comply. It was good motivation.
"Benjamin! Why are you looking at my breasts without my permission? I can see they are distracting you too much."
Isabella opened the same drawer I had a peek at. She took out a black eye mask. Benjamin realized it is for him.
"This should help," said Isabella and blindfolded Benjamin. "Much better, right? This way my hard pink nipples can't distract you."
Benjamin knew he had a choice, he wasn't tied up and the information about the drawer wasn't that important after all. It was just an excuse to stay in Isabella's bed. He wanted this and she knew it.
Even though Isabella said it is a punishment, she knew he was checking her out every time she visited his mother. She knew he wanted this. His reactions showed clearly she was right but Isabella wanted to check that theory.
"Benjamin, I don't want to do anything to you if you don't want me to. You may go, I won't tell your mother anything, this much humiliation is punishment enough. You can stay if you want to and we will finish the session."
Benjamin didn't move a muscle. He wanted this. He wanted to be dominated by her. Isabella was right.
"Are you staying? Wow, Benjamin, I didn't expect that from you," giggled Isabella. "I have a surprise for you... Get ready!"
Benjamin heard she took something from under the bed. He felt something soft on his chest tickling the nipples.
"Do you remember my hard nipples? I want yours the same, so I will pay A LOT of attention to them. I will not go easy on you. You must be punished for sneaking to my panties' drawer."
She was teasing his nipples with the feather. Benjamin felt a little pinch on his nipples and gasped. As the feather was going down, Isabella bit the nipple, only a little bit, though. She was touching the sides of his stomach. His body twitched.
"Are you ticklish? Don't worry, I'm not done with you," said Isabella and circled the feather around Benjamin's belly button.
The gentle torture didn't seem to end. He felt the feather going down his belly to his... cock. After she had tickled his cock, the feather teased his thighs and balls.
"How does your cock feel? I see it is still hard."
"I can't handle it anymore, Isabella."
"Benjamin... what did I tell you before? Am I Isabella to you? Repeat what you said again correctly if you don't want any additional punishment!" said Isabella and returned with the feather to teasing his cock.
"I can't handle it anymore... mistress."
Isabella smiled and stopped tickling him with the feather. Because of the blindfold, he couldn't see the satisfaction in her face as she left the feather on his belly.
"Now... This is a punishment, so, you don't deserve to be touched by my hands today. Don't even think about it. Since you've decided to do everything I say, go ahead and start stroking your cock."
Benjamin didn't overthink it, he automatically started stroking his cock. He loved Isabella's controlling voice. She somehow made him safe.
"Slow strokes only, Benjamin! I bet your cock can't handle fast stroking straight from the beginning," giggled Isabella."I'm sorry, but you have to take some deep breaths and stroke it slowly. You know it's better for you."
Isabella always liked to control men, especially those younger than her. She's always found Benjamin attractive and she was amazed how willingly he let her control him. She wanted to make him feel the best way possible, she wanted to feel the best way possible herself. She was controlling but gentle, she didn't want to scare him off from the very beginning.
"You may speed it up a bit. Do you like being tortured like that? How do your balls feel? Do they even have any cum?"
"They do have a cum, mistress," Benjamin protested.
"Shh! Don't you ever talk back to me if you don't want to be punished. Talk only if I ask you something. From the look of your balls, I wouldn't be so sure if it has cum. Go ahead and massage them a little bit to make sure they do have some cum."
Benjamin was a little bit frustrated. He always has cum! Although she let him massage his balls and that is pleasurable.
"You may stroke as fast as you want. At least for now."
