Becoming Brenda's Slave

I could not remember much about the cab ride back to my hotel. The pain of being brought so close to orgasm and then being denied was all I could think about.

When I reached my room, I removed my clothes and began to examine the cage that my cock was imprisoned in. It was made of a hard semi-transparent red plastic and it jutted straight out from my pubic mound before it curved and pointed downward. The downward curve was fine, as long as my cock was limp. However, if I started to get an erection, it would force my hard shaft to bend unnaturally making the erection painful. I also noticed that the inside surface of the cage was covered with little spikes that would dig into my flesh if my cock became fully erect, making it even more painful.

There was an opening in the end of the cage which would allow me to pee if I needed to. I then examined the strap that was attached to the bottom of the cage and was wrapped around the base of my testicles. The strap was adjusted just tight enough that it caused my balls to be swollen and distended, but not too tight so as to cut off the circulation. The effect was that it made my balls very sensitive to the touch.

I ran my fingers over my stretched scrotum and I immediately felt my cock begin to respond. It didn't take long before my cock started to grow, reaching the limiting confines of the curved cage. I groaned in frustration as there was no way for me to stimulate myself further.

I looked at the locking mechanism that was on the bottom side of the cage at the base. There was a small key hole and I thought about picking the lock but then I noticed there was a little adhesive seal that Brenda had applied across the seam of the cage where it opened. If I were able to pick the lock and open the cage, the seal would be broken and she would know what I had done. I decided it would be best to leave it alone and try to get some sleep.

I then remembered the envelope that she had given me. I looked at it and remembered her instructions to not open the envelope until morning. I thought about going ahead and opening it right then, but I had a strange feeling that she would somehow find out. I set the envelope back down on the nightstand and crawled under the covers.

I slept fitfully that night, thinking about my predicament and wondering about what was in the envelope. There was also the ever ongoing throbbing of the denied orgasm in my loins that kept me tossing and turning all night as well.

When morning finally came, I dragged myself out of the bed and stumbled into the bathroom. As I lifted the toilet seat, it suddenly occurred to me that if I tried to pee like this with the cage on, I would make a mess all over the floor. I realized that I was going to have to sit on the toilet like a woman in order to relieve myself. As I sat there, I had a feeling that this was also a part of her plan.

When I was finished, I returned to the bedroom and picked up the envelope. I sat on the bed and opened it. When I broke the seal, I caught a faint whiff of Brenda's perfume and the sweet smell somehow seemed to brighten my mood. I found myself looking forward to getting on with serving her. Inside the envelope was a hand-written page of instructions and also another smaller sealed envelope. I unfolded the sheet of instructions and began to read.

"I hope you got a good night's sleep." the note began.

I groaned as the long night had been far from 'good'!

The message continued, "You are going to have a very busy day and night ahead of you! After you shower and clean yourself up, I want you to go to an ATM and withdraw $500 in cash. Do not spend this money on anything. You will know when it is time to use it."

"After you get the cash, you must then go to this florist (she gave an address) and order two dozen red roses to be sent to my room this afternoon. You will then go to this wine store (another address) and pick up an order that I have placed there."

"After that, go to this address (this time it was just an address but no name of the business) and ask for Cheryl. You will find another sealed envelope with these instructions. You are to give this second envelope to Cheryl and she will then give you further instructions. Do not dare open her envelope! Remember if you are a good boy and follow all my instructions, you will be rewarded tonight!"

The note was signed with a red lipstick print. I noticed that the small sealed envelope had the name "Cheryl" written on it.

I quickly showered and got dressed, eager to begin my journey towards my promised reward.

There was an ATM just a block away from my hotel. I walked down to it and withdrew the $500 as she had instructed.

Once I had the cash, I hailed a taxi and gave the driver the address of the florist. I had the cabbie wait for me when we reached the flower shop. I ordered the roses and gave the cashier the address of her hotel and room number. The flowers cost just over $120 which I charged to my credit card.

I got back into the cab and gave the driver the next address of the wine shop. He drove me to the shop and again waited for me while I went inside. I went to the counter and told the man working there that I needed to pick up an order and gave him Brenda's name. He disappeared into the back of the store for a while. When he came back, he was carrying four bottles of wine.

He set them on the counter and I could see that there were two bottles of red wine and two bottles of champagne. As he started to ring up the purchase he commented, "These are some very excellent choices sir."

The first bottle of champagne rang up for just over $60. By the time he had rung up all four bottles, the total was over $200. I paid again with my credit card and carried the bottles back out to the cab. I was starting to get concerned with how much this day was going to cost me!

Once I was settled in the cab again, I gave the driver the final address in her instructions and he drove off. It took nearly thirty minutes to reach our destination. Finally the cab pulled over to the curb and stopped. I looked out the window and saw that we had pulled up to an adult book and toy store. The driver asked me if I wanted him to wait on me but I decided to let him go as I was not sure how long this was going to take.

I paid the driver and then opened the door to the store and went inside. The front room of the store was filled with all kinds of sexy lingerie. There was a checkout counter by one of the side walls where a young man was ringing up a customer's purchase. I walked over to the counter and waited until he was done with the customer.

He asked, "May I help you?"

I responded nervously, "Uh, yes. Do you have someone named Cheryl working here?" He nodded, and for a moment I thought I detected a knowing smile cross his lips.

"Wait here," he told me as he walked to a back room.

As I waited, I idly browsed through the racks of lingerie, occasionally stopping to feel the silk and lace. I was lost in thought thinking about how good Brenda would look in some of these outfits when I heard a sultry female voice behind me say, "See anything you like?".

I turned around and saw a tall woman standing near the register. She had dark hair that was clipped into a bun at the back of her head. She was wearing a gray business suit with long slacks and black pumps. She was wearing black horn-rimmed glasses and my first thought was that she looked like a librarian. The suit she was wearing did a good job of concealing her figure but I had a feeling that she had a very sexy body hidden beneath.

"Hi, I'm Cheryl," she said as she extended her hand for me to shake. I took her hand and found that she had a surprisingly strong grip.

As we shook hands, she asked, "How can I help you?"

I reached into my pocket and took out the envelope with Cheryl's name on it. I handed it to her and said, "I am supposed to give you this."

She took the envelope from me and the first thing she did was examine the seal which I thought was strange. Once she was satisified that the seal was intact, she popped the envelope open and removed the contents. There were two pages of notes in the envelope. She read through the notes and a smile appeared on her face. I was dying to know what Brenda had written on these notes!

When Cheryl had finished reading the pages, she simply said, "Follow me," then turned and walked through the rear door to a back room.

As I followed her, I found the next room was filled with every imaginable sex toy that one could think of. We continued through the room until we reached a set of dressing rooms. She reached into her pocket and took out a key which she used to unlock and open one of the dressing room doors. She held the door open and instructed me to step inside. Unsure of what was going to happen next, I hesitantly stepped inside. She followed me into the small room and closed the door behind her.

Before I could say anything, she asked, "Do you have some money for me?"

"What do you mean?" I stammered.

"The note says that you have $500 cash for me. Do you have it or not?"

"Yes, it's right here," I replied as I reached in my pocket and pulled out the bills. I handed her the money which she quickly counted. She then unbuttoned the top button of her suit and stashed the money in her bra between her cleavage.

She then turned her attention back to me and said, "Take off your clothes."

"Wh-what?" I cried out. "Why do I need to take off my clothes?".

A stern look came across her face and she said through tight lips, "The note that you gave me said that you are to do everything that I say. If you don't obey me, I am supposed to call this phone number and let your mistress know that you are mis-behaving. It also says here that if your mistress has to get a call from me, she will throw away the key. I assume you know what that means?"

I nodded in defeat and began to remove my shirt. I stripped down until I was only left with my underwear. I suddenly was feeling very self-concious remembering that my cock was still imprisoned in its cage.

Cheryl saw my hesitation and said, "Come on, let's see it."

I finally pulled off my underwear and stood before her very red-faced.

She laughed and said, "My my, will you look at that! I can see that your mistress has you under control!"

She reached out and lifted the cage up so that she could get a better look at it and my balls that were streched out by the strap. She took her other hand and began teasing my balls with her fingernails. After a few moments, my cock started to respond and began to grow in the confines of its prison. Once I had reached the point where my erection was getting uncomfortable, she stopped.

She opened the door and told me, "Wait here. I'll be back in a few minutes."

When she returned, she had a small bag which she set on the shelf. She reached into the bag and pulled out a pair of latex gloves and a bottle of lubricant. She put on the gloves and removed the cap from the lube. "I want you to spread your legs and then bend over and grab hold of your ankles," she instructed me.

I did as I was told and I suddenly felt that my ass was very vulnerable in this position. I was right to be concerned. I heard her squirt some of the lube into one of her gloved hands. The next thing I felt was my ass cheeks being spread and then one of her lubed and gloved fingers entering my ass. She slowly stroked her finger in and out of my ass for a few moments before she inserted a second finger and then a third. She continued to work her fingers inside of me for several minutes until my cock started to grow uncomfortably inside its cage again. Finally she stopped and said, "There, I think you should be ready now."

She reached back into the bag and removed a very large butt plug. It was made of black rubber and was about 4 inches long. It was tapered in shape such that the tip was only about a half inch wide but it was about 2 inches in diameter at the base. There was a flange below the base that would keep the plug inserted once it was inside. She held the plug down in front of my face so that I could see it. I started to protest but she quickly reminded me that she would call my mistress if I didn't cooperate so I told her to go ahead.

She lifted the plug back up out of my sight and I heard the sound of more lube being squeezed out. I felt her hand spreading my cheeks again and then I felt the hard rubber tip of the plug touching my opening. She slowly began pushing it inside me.

At first it was OK, but as she pushed it in deeper, I could feel the widening base of the plug stretching my hole further and further. The pain of the rubber stretching my ass was almost too much for me to bear and I was just about to cry out when I felt the base of the plug pop inside me and my asshole closed around it. The pain had stopped but I now had a strange feeling of fullness in my ass. She then told me to stand up and as I did, I could feel the plug in my ass even more.

She then removed a pair of red thong panties from the bag and she knelt down and held them at my feet and told me to step into them. I did as I was told and once my feet were in the openings, she slowly slid the panties up my legs until she had pulled them up over my caged cock. She adjusted them so that they fit snugly over my captive member and the strap of the thong went up my ass crack. She then stepped back and admired her work.

"How does that feel?" she asked.

"It's a little strange," I replied.

She then instructed me to take a few steps around the room. I found that the plug in my ass was making me take short, mincing steps and I felt a little ashamed.

She laughed at me and said, "Wow, look at you walking around like a little slut! Don't worry, you will have plenty of time to get used to it. Your mistress left instructions that you are to wear these things for the rest of the day until you meet her this evening."

She then instructed me to get dressed but she kept my male underwear saying, "You won't need these anymore".

Once I had put my clothes back on, she led me out of the dressing room and towards another area of the store which was full of adult videos. I was very self-concious about the way I was walking and I tried my best to hide it but I was sure that anyone who saw me must know that I had something up my ass.

She led me to a back corner of the video room and said, "I want you to wait right here. Your mistress has a shopping list here and I am going to go gather up these items." With that she turned and left me there.

After she left, I started looking at the racks of videos in front of me. Suddenly, to my horror, I realized that she had led me to the gay porn section of the store. All of the videos around me were of men fucking and sucking each other without a single female in sight.

I was now very uncomfortable knowing that I had something stuck in my ass and I was wearing womens underwear looking at gay porn movies. I was petrified that someone I know might walk by and see me. A couple of women shoppers passed by and looked at me and as they continued I saw them whispering to each other and laughing. A short time later, a young man came over and started browsing through the movies. He looked at me and smiled and I realized he was checking me out! I quickly turned away and tried to act like I was busy doing something, anything else.

Cheryl was probably only gone for about 15 minutes but it seemed like an eternity. When she finally returned, she was carrying two large shopping bags and one small one.

"See anything here that you like?" she said with a twinkle in her eye.

"No," I replied.

"Are you sure? There are a lot of good quality videos here," she said.

I was now very red-faced and was looking down at the floor. Finally she laughed and said, "All right, come with me. I think we're ready to check out now."

She walked away quickly and I hurried to follow her. My hurried pace and the plug in my ass made my walk even more feminine than before and I could feel the eyes of the gay man following me as we headed to the front of the store.

Once we made it to the front, Cheryl set the three bags on the counter and started ringing up the items that were on the list. When she was finished the total came to about $280. I groaned as I pulled out my credit card again and paid. I was in for over $1100 now!

Once the sale was complete, she handed me the small bag and said, "This bag is for you. These other two bags will be delivered to your mistresses hotel room. There is a taxi waiting for you outside that will take you back to your hotel. Once you get back to your room, you may open your bag. Any questions?"

I shook my head, "No."

"Thank you then and good luck," she smiled at me, "I think you're going to need it!"

I made my way out to the waiting cab being very mindful to try to control how I was walking. The cab driver took me back to my hotel, where I paid him and carefully made my way back up to my room.

Once inside my room, I opened the small bag that Cheryl had given me. Inside it was another hand-written note from Brenda and a DVD.

I read the note and it said, "Your assignment for this afternoon is to watch this entire DVD. You need to pay very close attention to it and don't try to skip any of it as I will be asking you questions about it later. This evening you will bring the wine that you picked up and arrive at my hotel room at precisely 8:00 PM. Don't be late and don't attempt to remove any of the special 'items' that you are wearing." It was signed with another kiss print.

I pulled the DVD out of the bag to look at it. It was titled "Cruel Femdom Fantasies" and the cover stated that it was four hours long! I looked at my watch and saw that it was already 1:00PM so I powered up my laptop and inserted the disc into the drive.

The video was divided into five scenes. Each of the first four scenes focused on a different beautiful dominatrix and her male slave. There was heavy emphasis throughout all of the scenes on cock and ball torture. All four of the slaves were screaming and begging for mercy before the end of their repsective scenes.

I found myself becoming scared by what I was seeing but also found that I was getting very turned on. Before the end of the first scene, I had a raging hardon that was painfully grating against the inner spikes of my cock-cage.

I removed my clothes and tried to find some way to stimulate myself but it was no use. The best I could do was to massage my distended balls through the silky material of the thong that I was wearing. By the end of the second scene my cock was dripping a steady stream of pre-cum that soaked into the material of the panties but I could not achieve orgasm no matter how hard I tried.

The final scene of the DVD had all four mistresses gather together with their slaves for a party. The orgy that followed was insane! Each of the mistresses took turns torturing each of the slaves. The slaves were all made to service each mistress in any way that she desired. The mistresses also made love to each other forcing their slaves to watch. Finally when the mistresses had all had multiple orgasms, they forced the slaves to perform sex acts on each other until all four of them had cum.

When the video ended, I could barely walk because my cock was so hard and in so much pain from its prison. It was just after 5PM and I decided that I needed to try to lay down and get some rest before the evening activities continued.

When I awoke, it was just after 7:30 and I started to panic. I hurriedly put on some clothes, grabbed the bottles of wine from the refridgerator and headed downstairs to get a taxi.

Traffic was heavy and the cab ride over to Brenda's hotel took longer than usual. We finally pulled up in front of her hotel and I paid the driver, grabbed the wine, and headed inside. I knew that I was mincing my steps again from the ever-present butt-plug in my ass but I didn't care as I wanted to make it up to her room on time.