Mark was a single 35-year-old male with an obsession on femdom. In his marriage he was too intimidated to broach the subject with his ex-wife. She ended up leaving him due to a lack of sex. It wasn’t that he didn’t want sex, he just had different needs and did not know how to communicate those needs.

It was Friday night, and Mark was wearing his chastity cage. He wore it often and had fantasies of meeting a woman with the same kinks that he had. He had been locked for close to 90 days this time. It was his longest lock up yet.

Tonight, he was looking at FetLife and saw a profile that caught his attention. It was a listing for a Domme who was 52 years old. She was into most of the kinks and fetishes he was into. But her list was much longer. Her profile name was Helenownsyou. Mark decided to write to her. He sent her a message that described his situation. He asked her about her interests, complimented her on her photos, and asked what she was looking for.

Once the message was sent he continued to look at her photos. She had close to a thousand photos. She was what some would call thick and others would call a small BBW. Mark found her curves mesmerizing. She also had a tendency to wear corsets and high heels, two things that were high on Mark’s fetish list. She had pictures of her playing with bound men and women. They were all almost always wearing lingerie and heels, even the men. Mark had never really considered cross dressing but the idea of being forced to like some of the men in the photos made him strain against his already tight chastity cage.

About that time, Mark noticed that he had a message. He opened it and it was from Helenownsyou. The message said, “Hello Mark, I am looking for a new slave. You will have to prove to me that you are up to it though. Step 1. DO NOT REMOVE THAT CHASTITY CAGE! Step 2. Meet me for lunch tomorrow. I will send you the details in the morning at 10AM. Step 3. DO NOT CUM.”

Mark did not sleep much that night. He leaked and strained against his cage. His balls ached from the worst case of blue balls he had ever had. But the main thing was he could not stop thinking about her.

The next morning, Mark checked his messages at 10AM and there was another message. This one said, “12:00 at Ben’s Diner. Bring your key and wear pink panties. Don’t be late.”

Mark didn’t own panties, much less any pink ones. The thought of wearing pink panties was humiliating and exciting at the same time.

On the way to the diner, Mark stopped at the local lingerie shop and bought some pink panties. Then it occurred to him, he didn’t have time to go back to his house to put the panties on. He asked the woman behind the counter if he could use their dressing room. The woman just giggled and pointed to the door at the back of the shop.

Mark arrived at Ben’s Diner and immediately noticed Helen at a table. She was wearing a red leather skirt and jacket with a light beige silk shirt. She was also wearing 5-inch red heeled shoes. He approached her and she got up and gave him a hug. He could smell her perfume and the scent of leather from her skirt and jacket. She had raven hair and blue eyes and he noticed her ample cleavage when she sat down.

They ate a late lunch and discussed Mark’s divorce, and it turned out Helen was also recently divorced. It seemed that Helen’s husband had introduced her to kink. Towards the end he did not want to obey her. Apparently, he liked the kinky sex but when Helen wanted to pursue long-term chastity and a real Female Led Relationship, he refused and she divorced him.

After lunch, Helen invited Mark to discuss her requirements of Mark, and if he wanted to pursue serving her. Of course, he wanted to serve her.

He followed her to her house and was impressed. She lived in the best neighborhood and her house was huge.

When they entered the house, Helen turned to Mark and said, “Give me your key. You will remove your clothes and fold them, place them on the bench. Leave the panties on. From now on you will not wear clothes in my house unless I approve them. Also, you will address me as Goddess Helen from now on. Do you understand, slave?”

Mark was stunned but managed to stammer, “Yes, Goddess Helen.”

Helen then opened a drawer next to the bench and pulled out a leash and collar. She then put it on Mark and led him down the hall to a room that she referred to as her play room.

Inside the playroom there were several large pieces of bondage furniture. Whips, paddles, and other bondage equipment were on one wall. In the corner was a sofa with a large yoga pad in front of it and along the wall were some chests that resembled black tool chests.

Goddess Helen told him to kneel on the yoga mat. She sat down on the sofa and crossed her legs. He couldn’t stop staring at her shoes. He moved his hand to cover his penis locked in the tiny cage under his panties. She said, “Look at me, slave! Do not cover yourself again!” Mark looked up and she said, “Now, let’s cover my rules: One. You have been locked for 90 days? That is a start. But you can do much, much better. Let’s make it 6 months?”

Mark said, “No…please…”

Goddess Helen grinned and said, "Ok, a year then… or do you want to negotiate some more? No? I didn’t think so.”

Mark felt his tiny cage get even tighter and he moved to adjust it.

“WHAT ARE YOU DOING, SLAVE?”

Goddess Helen then stood up and walked to the wall with all the bondage gear hanging on it. Mark could hear her heels clicking on the hard floor and then he heard the clinking of metal. He knew better than to turn around and look for the source of the sound. She stopped right behind him and instructed Mark to put his hands behind his back. He obeyed and she strapped his wrists together tightly. Then he heard a lock click shut. Next she strapped his arms together just below his elbows.

She then instructed Mark to stand up. Then he heard a hum followed by something clicking to the strap around his wrist. Then another hum and he felt his arms raising, forcing him to bend forward.

Goddess Helen walked back to the wall and came back with what turned out to be a spreader bar. She attached it to his ankles. Mark had never felt so vulnerable before in his life.

Goddess Helen said, “You are about to find out the consequences of disobedience. It will not be tolerated, slave!”

He heard her go to the drawers and then behind him again. He felt something cold in his ass and then a cool sensation as Goddess Helen squirted lube into his ass. This was followed by a burning sensation as his virgin ass was stretched to accept a butt plug.

She walked back to the drawers and came back with some chains and straps hanging from her hands. She sat on the sofa and grabbed Mark by the hair, pulling his head back roughly. She was holding a head harness with a ring gag. “Open wide, slave!” she ordered.

Mark knew he had no choice and opened his mouth. Goddess Helen wedged the O ring in, forcing his mouth even wider than Mark thought possible. Then she busied herself with buckling all the buckles. Once she was satisfied, she locked all the padlocks on the head harness. She then held up the chains. They had nipple clamps on one end and a ball weight on the other end. She saw the fear in his eyes. Mark had always had overly sensitive nipples.

She giggled a little and said, “ You are going to love these, slave. The harder you tug on them the more they pinch. After a while they won’t hurt as bad… as long as you don’t move. But I have a feeling you will be moving a lot.”

She then went to the wall and brought back four implements: a single tail, a strap, a paddle, and a cane. She laid each on the sofa next to her. She picked up the strap and said, “I’ll bet you are eager to get started.”

Every time she struck with the strap, the force drove Mark forward, causing the ball weights on the nipple clips to sing and bounce, further torturing his nipples.

Next she used the single tail. It stung and caused Mark to dance around, at least as much as his bondage would allow.

The paddle made him feel like his ass was on fire and it was humiliating.

The cane was the worst and after 5 strikes he had tears in his eyes and he was sobbing.

Goddess Helen then came and sat on the sofa. She grabbed Mark by the hair and pulled his head back. She reached down and removed first one nipple clamp and then the other. She then pulled and twisted on each one. Mark didn’t know how much more he could take and was trying to beg her for mercy but all that came out was an unintelligible gurgle.

Finally she stopped and said, “I am going to go change. I will let you rest here. Don’t run off, now!” And she got up to leave. Then she came back like she forgot something and put the nipple clamps back on Mark.

It seemed like he was there forever. Finally he heard the click clack of her heels on the tile floor. She walked up in front of him and she was wearing black leather shorts, black thigh-high boots, and a black leather Demi cup corset. But the thing that struck fear into Mark’s heart was the 8-inch strap-on sticking out in front of her.

She said, “I am going to make you my whore tonight. You will never be the same after this. I am going to peg you until you beg me to turn you into my sissy slave. You will have to convince me, not just say the words.”

She pegged him until he tried to beg but the gag was still locked in place. Finally she removed the gag and he begged and begged even more. She just laughed and kept pounding away. Finally, she quit, removed the nipple clamps, lowered him back to his knees, and sat on the sofa. She then ordered him to lick her boots clean.

She said, "The next time I have to discipline you, you will get 'The Stick'. Now, let’s get you sissified. Finish going over my ground rules, and then I am going to peg you again.”

“Yes, Goddess Helen. As you wish, Goddess Helen.” Mark knew he was lost and completely out of his depth.

To Be Continued…