How I Was Turned Into a Sissy Pt. 02

Normally I am not big on writing sequels to my stories, but I have been asked if I could write a second part. So here it is... enjoy!

The morning after my wild night on Halloween, I woke up feeling different. I don't mean wearing the chastity cage either. After having anal sex with Carl, then with Linda, my introspection has changed. No longer did I feel like a straight man in my mind. After months of Linda poking at me being possibly gay, even though I kept on denying her notion, I took the plunge and had sex with the first man who hit on me at the party. The feeling I was getting was I am on my way to find the real me.

Getting out of bed, I smell the coffee brewing in the kitchen. Linda must be up. Glancing at the table, there was a note and a key.

The note read, 'I had no right to force the cage on you. Please take the cage off and bring the cage to me. Meet me in the kitchen. "

Thinking about the notion of keeping wearing the cage and possibly pleading with her, I decided to take off the cage. There is no need to make hasty decisions when your feelings are very mixed at the moment.

As I took off the cage, my cock sprang to life. The feeling I was getting was my cock enjoyed its prison. Grabbing my Ratt 'Out of the Cellar' t-shirt and the cage, I headed to the bathroom to use the bathroom. After I got done using the bathroom with my t-shirt and black boxers on, I headed to the kitchen.

Upon arriving in the kitchen, Linda was enjoying her cup of coffee with a Marlboro as she read the morning newspaper. Reaching inside the cupboard, I grabbed myself a small glass. I grabbed the pitcher on the counter and poured myself some orange juice, then proceeded to sit at the table with Linda.

As Linda slid me the sports page, she greeted me by saying, "How do you feel this morning?"

With my face red from embarrassment, I replied, "I am perplexed emotionally. What happened last night was profound to me. Maybe if we discuss last night, it might help me compartment my feelings better."

Linda agreed with me. For the next hour, we discussed my feelings and what the future might hold. I was still unsure if I really wanted to follow this new road in front of me. Linda assured me whatever I decided, she would support my decision.

As the conversation ended, Linda and I agreed I need to sort out my feelings and do any research I felt was necessary before I make my decision. She doesn't want me to pressure her into being her feminized sissy.

Linda said, " What she said and did last night in the heat of the moment."

The one thing Linda did offered me was if I need advice or help me with my emotions, she would help me.

Over the next couple of weeks, my emotions were everywhere. Lucky for me, I work from home as an accountant for my family's accounting business. Even though my mind was on what happened on Halloween, I was still able to do my job. My mom and grandfather thought it was best I work from home anyway.

My mom's explanation was, " I do my best work when I am alone and the office is not a fit for me."

The only catch was I had to come to the office once a week to pick up paperwork to work on from my home, and I attended the weekly morning meeting on Monday morning.

On this peculiar Monday, I left the office after lunchtime with my grandfather and mother. They have been happy with the work I have put in for the business. Between my organization and bookkeeping with the mixture of my talent dealing with numbers, they liked the arrangement we had.

As my grandfather said, "Why fix something that isn't broken?"

There I got rambling again. Back to our story, I was driving to Linda's store to see if she would like me to cook or get take-out instead. She owned a store for women's clothing beside the dominatrix business she did on the side. I've never been to her store or even inside the store. There was never a need to go when I don't shop for women's clothing.

Arriving at Linda's boutique, which is what she called the store, I exited my '90 Mustang and walked inside. Upon entering the store, I was amazed and shocked. I didn't know she was actually running a BDSM/clothing store. One side of the store was nothing but BDSM items, while the other side was clothes for crossdressers, TVs, and the dominant woman. The back wall was mostly dildos, sex toys, and accessories for crossdressers and TVs. There was a rectangular counter in the middle of the store so the store could be watched at all times.

As I look around, Linda is counting the cash registers down, setting them for peak hours, which happen to be between 3pm and 6pm. She looked up and was surprised to see me.

Linda came over and hugged me, then asked. "What brings you to my store? You never set foot in here. "

"I thought about what we are doing for dinner. I figured if I was in the area, I would stop," I explained.

"Are you sure you aren't shopping for women's clothes secretly?" Linda asked with a mischievous grin.

"I was just stopping to find out if you want a takeout or home-cooked meal," I said with an angry tone.

"I was just messing with you. I know you have a million of things going through your head. Are you sure you would rather not look around and explore? " Linda asked.

I let out a sigh as I replied, "Sure, maybe a look will help me sort out my feelings. "

Linda clapped her hands happily and said, 'Feel free to explore and let me know if you need help."

I nodded my head yes as I headed to the BDSM side first. There were four sections to the BDSM side: hoods with latex and leather clothing, BDSM equipment, chastity devices, and disciplinary devices. The first item that caught my attention was a black leather hood with a hole for eyes and a mouth and a ponytail on top. This was interesting in itself.

I looked at the hood like it was speaking to me. Wondering how the hood would feel over my head starts to bring up some emotions. I felt myself getting turned on by this item.

Linda walked over and broke my trance by whispering in my right ear, "You know you want to try that hood on. I can help you."

I didn't say anything but nodded my head yes. She pulled the hood off the shelf and grabbed my hand to lead me to the dressing room. Upon arriving at the dressing room, Linda left the hood with me as she told me she was going to do a few things for me. I nodded yes as I took the hood.

Looking at the hood was like the hood was calling me. Now I am perplexed. Do you want to be like the gimp in Pulp Fiction, or do I want to be dressed in drag like in The Birdcage? My feelings and emotions were all over the place.

The smell of leather was intoxicating. Being around leather all my life. The smell never turned me on before. I decided to take the hood off the mannequin head. The hood was open to me now. Looking inside the hood, I wonder how the hood would feel tight around my head. I noticed if my hair was ponytailed, the ponytail fits through the hole on top.

As I was studying the hood, looking at the hood and taking in the aroma, Linda came in with a pile of items with a black and white latex maid outfit. Hanging the outfit up, she laid out the items on the bench.

"Since you are going to need help with putting on this outfit, I have put on the front door, 'Be back in 30 minutes.' Gone to lunch ' sign up for my undivided attention for you," Linda replied.

I said, "Thank you."

"NOW, STRIP DOWN!" Linda ordered.

I stripped off all of my clothes, standing naked in front of Linda again. What is wrong with me? Do I have crave this type of attention this much? Am I being weird because I slowly stepped into a world I thought I would never step into? Normal people don't do this kind of behavior.

Linda handed me the black latex stockings first. I sat down on the bench and slowly rolled each stocking over my shaved legs. The latex felt cool against my skin. Linda decided to hand me a pair of latex panties. Looking inside the panties, I noticed a small 1-inch butt plug sewn into the panties.

"I want you to wear these for what I have planned," Linda stated to me as I stared at the panties.

She squirted a little lube on the plug as I opened the panties up to put them on. I slid the panties up to my waist. As I pulled the panties to my waist, the plug slowly eased its way into my ass, making me feel full. I let out a little moan.

"Concentrate, Mike. I only have 20 minutes left," Linda exclaimed.

I nodded my head yes. Linda handed over a pair of size B silicone breasts. I looked at her like she was crazy. What in the hell were these for?

"If you are going to dress like a woman, you need to look like a female," Linda pointed out.

I put the breasts on like a bra. Linda clasped the bag for me. I felt the weight as the breasts hung on me. Linda smiled as she handed a black latex bra to me. Putting on the bra, I felt the weight get lifted a little bit as Linda clasped the bra behind me.

Looking myself in the mirror, I was amazed so far at how everything is turning out. Linda handed me the dress. I stepped into the maid dress and pulled the dress up over my new breasts and body. Linda zipped up the back, feeling the latex tight around me. What I didn't know was there was a corset built into the latex maid dress. I felt my waist shrink by one size.

"You look perfect. All you need is the hood and shoes. Bend over for me so I can put the hood on you," Linda ordered.

I bend over for Linda. First, she ponytails my long hair tight to the top of my head. Sliding the hood over my head, she pulled my brown ponytail through the tube on the top of the hood. Making sure the hood fit properly, Linda adjusted the hood and pulled the zipper down, making sure not to catch my hair in the zipper. As the zipper came down, I felt the hood face forming to my face tightly.

Linda looked at me and decided I needed something else. Linda ran out of the dressing room, then came back quickly with a tube of red lipstick. Slowly, she painted my lips red.

Looking in the mirror, I was awed by how I turned out. I saw a beautiful maid looking back at me. Linda smiled as she put a pair of black heels in front of me. I slowly put each foot in the heels. At first, I was unsteady, but I got the hang of walking in heels. Linda helped me to the counter with my clothes in her hands.

She put my clothes and a special treat in my bag. Ringing up the items, she gave me half of everything I was getting for the transformation. I gladly gave her the money.

"When you get home, I expect dinner to be fixed and served when I get home. You are to stay dressed like this until after dinner. Do you understand, sissy?" Linda ordered.

"Yes, Mistress!" I exclaimed.

With that being said, I left with my bag in hand. I quickly walked to my car without being noticed. Starting the car, I headed home. As I was driving, it felt weird driving in heels.

Arriving at my house, I quickly pulled into the garage and shut the garage door. Thank God, no one saw me. I don't think I could handle the humiliation. Walking into the house, I set the bag on the counter. My work could wait until tomorrow.

Looking in the bag, Linda put in the bag for me a pair of black lace fingerless gloves with a couple of different magazines. Taking the gloves out, I slowly put them on over each hand. The lace felt different.

I decided to clean the house first, and then I would start dinner. I set up my video camera and hit record as I started to dust the table and pick up the mess in the living room. As I moved through the room, I could feel the plug move with each step. It felt weird, especially since the plug caused me to get hard in my panties.

To take my mind off everything, I started to vacuum the living room. Big mistake, the vibrations in my hand from the vacuum made the feelings worse. I quickly vacuumed to get the torture over with before I decided to explode.

After I put everything up and turned off the camera, I headed to the kitchen. Looking in the fridge, I see Linda did pull something out for dinner. This makes me wonder if she was plotting against me. Never mind, I pulled out a glass pan and put the pork chop in the pan. After I seasoned the chops, I put them in the oven. I decided to cook some broccoli and rice on the stove. That could wait until the pork chops are about done.

I sat down at the table and picked up one of the magazines. The magazine was called "Transformation." The magazine deals with TVs and cross-dressing. Reading the different stories and articles, I was started broaden my horizons on my fetishes. The article I was drawn to most was on the subject of chastity and bondage.

With the pork chops halfway done, I set the magazine down on the table to get up to cook broccoli and rice. Pulling two pans out, I placed the pans on the stove, then proceeded to fill the pans with the sides I was cooking.

As everything is cooking, I proceed to set the table for Linda and me so she can have a hot meal when she gets home. Placing the silverware and plate where she and I normally eat, I went and retrieved her favorite wine glass for dinner. Placing the wine glass on the table, all that was left needed was her and the food.

10 minutes later, Linda walked in. Smelling dinner, she sat down and waited for me to place dinner on the table. I slowly placed each dish on the table with the proper serving utensils. The next thing I did was grab the bottle of red wine in the fridge. Walking to the table, I slowly pour the red wine in her glass. Linda smiled as I finished my task.

Linda ordered me to sit down and eat with her as we talked about how I felt at this moment. I explained to her what I did when I came home, to which she smiled. After dinner, she ordered me to clean up while she would watch the tape.

She left for the living room as I started to clean the table off like a good servant. What I didn't know as I was cleaning was that Linda went to change into a new outfit. As I was finishing cleaning up by sweeping the floor, Linda called me to the living room.

As i walked into the living room, a beautiful statue of a woman in dressed in latex was standing in the room smoking a Marlboro Lights 100. Linda was wearing a black and red latex bodysuit with red leather thigh boots and red latex gloves. Her hood was red with a black spike collar around her neck. She pointed to the ground. I kneel before her like a good slave.

"I have seen someone embrace their kinky side by making a video of themselves cleaning. That makes me very horny and wanting to reward you. Are you up for a little adventure tonight?"

Linda asked me.

I reply with my eyes lower, "Yes, Mistress," as I remember remembering that response from a story earlier out of the magazine.

Mistress ordered me to stand up and stand still as she retrieved a couple of items. As I wait patiently for Mistress to return, I wonder what she has planned for me. Her click of her boots coming toward had me anxious and excited but scared at the same time. I trusted Linda fully, but now that's the way we are both dressed, and this new dynamic between us had me wary.

Mistress walked behind me, I felt something going over my eyes, causing my world to go completely dark. As I started to freak out as I thought I finally went blind from playing with myself after all the years, Mistress whispered in my ear to calm down.

Waiting for her next move patiently, I heard a ruffling of latex as she was preparing the next item. The suspense is killing me. What does she have planned? As Mistress ordered me, I raised my arms in front of me.

Standing before Mistress, I feel latex slowly covering my exposed arms until my hands hit the end of some type of enclosed sleeve. I felt some type of straps being pulled, which forced my arms into an x position tight across my chest. Mistress finished securing the latex straitjacket by pulling the straps between my legs and buckled the straps to the front of the straitjacket.

Helpless and at her mercy, I felt myself getting hard in my panties. Bondage never turned me on before, much less dressing like this and being helpless with being at someone else's mercy. Was this some sick fantasy I had?

Mistress smiled as she kissed me with a mouthful of smoke. I coughed at first, but with her deep kiss, I melted in her embrace. There was something erotic about this embrace.

"Someone is enjoying this. Maybe I need to show control," Mistress exclaimed as she walked away from me.

Wondering what she meant by that comment, I heard her returning from wherever she went. Out of the blue, I felt something cold between my legs, causing my cock to shrink. Mistress was using one of my cold packs to cause me to go limp. As my cock was limp, I felt Mistress pull my cock out of my panties and slowly fit a metal ring around the base of my cock.

Oh no, she must have read where I put a placemat in the magazine I was reading. She was getting ready to chastise me again. Starting to struggle in my bonds, Mistress smacked my ass to calm me down.

"You are going to wear this cage. It is not ladylike to have a hard erection in your panties," as Mistress said as she put the cage over my cock.

With a swift click of the lock, it was official. I was under her control. Mistress ordered me to step out of my heels, which I obeyed. Placing a pair of black ankle boots in front of me, she ordered me to lift my feet up one by one as she slid the ankle boots on one at a time. She completed the task as she pulled the straps tight around my ankles and placed a small lock into each clasp.

Mistress looked at me and decided I was missing something. Pulling a black leather collar off my coffee table, Mistress fastened the collar around my neck and placed a small lock in the clasp, effectively fastening the collar around my neck. She finished my look by attaching a small chain lead to my collar.

"Now you are ready to be transported to my dungeon. I will lead you to my car and we will be off," Mistress explained.

In that instant, I felt the lead tighten and pull me to follow Mistress through the hallway to the garage. She led me around her Mercedes to the passenger side. Heard the door open; she helped me sit down and put my legs in the car.

I am glad she had tinted windows on her car, or otherwise I would truly be embarrassed. She slammed the door shut as she walked to the driver's side and got in herself. Starting the car, she put the car in drive and left out of the garage to our next destination.

At this point, I don't know or can't see where we are going. Mistress has the music cranked up in the car to distort me further. After 20 minutes, the car stopped. We must be at our destination. I was starting to get antsy in my seat. Mistress got out of the car first. I tried to wait patiently, but being in tight bondage and unable to see, I was getting anxious.

A few moments later, she finally opened the passenger door. Feeling two sets of hands on me, she must have gone to get someone to help her. Is it an another slave or a Dominant? Now I am really getting scared and anxious. I started to hyperventilate, but Mistress assured me there was nothing to worry about and I should calm down.

With me standing by the car, Mistress grabbed the lead and pulled me to follow her inside to whatever location we had arrived at a few minutes ago. I heard two sets of steps as I followed Mistress.

We continued walking down a hallway until we walked into the dungeon. The dungeon has a beautiful layout, if you wanted to call it that. There was an X rack against the back wall. Next to the rack, an oak stock stood beside the rack. There was also a chair with stirrups in the dungeon, across from the rack. A cage that looks like an iron maiden stood against the wall, not too far from the chair. The dungeon was complete with a cell with a bed, a latex vacuum bed, and a cabinet full of BDSM items. The dungeon was well equipped.

Mistress led me to the chair and pushed me into the chair. She removed my latex panties, exposing me to the cool air. One by one, she placed each leg in a stirrup, effectively spreading my legs open for her, exposing my cock in the cage as well.

Mistress stood between my open legs and placed her two fingers on her latex right hand in my mouth to get wet. I started to suck on them like they were a cock. The taste of latex was causing me to strain against my cage.

"Someone is enjoying that. Maybe I can make a call and you can suck a real cock tonight for me," Mistress said to me as I sucked her fingers wet.

After a few minutes, Mistress pulled her fingers out of my mouth and slowly started to push her fingers in my ass to see how loose I was from the plug. She was pleased with how her fingers went in with ease.

"You are nice and ready for my new plug," Mistress said with an evil grin.

Mistress pulled her fingers out after a hard shove on my asshole. I nearly jumped out of the chair. Walking over to the cabinet, she pulled out an inflatable plug for me. As I sat there anxiously waiting for what was next, Mistress walked back over and lubed the plug up.

Getting between my legs, Mistress slowly rubbed the plug against my hole. I moaned with pleasure as she teased my hole.

"Please put in the plug in my hole," I was thinking.

She was getting me to crave some anal play by teasing me. Slowly, she shoved the plug in my asshole. I moaned in pleasure as my asshole was being invaded by the plug.

"I wish it was a real cock," I was thinking to myself.

My craving for cock must be kicking in at this moment. As she slowly expanded the plug, I moaned in pleasure as the plug filled my asshole like Carl's beautiful black cock. After this, I might call him while I am dressed as a latex maid.

"Someone is craving something. Let me resolve your problem, sissy," Mistress said.

Mistress walked away and slowly put on her starpon harness. She made sure her 8-inch black life-like cock was perfect in the harness. Slowly stroking her cock with her left hand, she slowly placed a cigarette between her ruby red lips and lit the cigarette with her lighter.

Mistress walked over and pulled on my plug. I moaned in pleasure as my asshole wouldn't give the plug up. It felt so good, feeling full. She slowly let the air out of the plug. Pressing a button at the bottom of the chair, the chair laid down, with me on my back with my legs spread in the air.

Pulling the plug out, Mistress stood between my legs as she stroked her cock with lube. She was preparing me for her cock. With a slow movement, Mistress slowly penetrates my asshole with her cock. I moaned slowly as I took her cock.

Mistress slowly fucked me as I moan in ecstasy. I feel myself building up come in my caged cock but am unsure if I could come before her. With each pound, I was getting hornier and hornier. I want to get on all fours and be fucked doggystyle. Mistress smiled, and she waved her left hand to come over.

"Maybe you would like a cock to suck as I fuck your ass," Mistress suggested.

My mouth opened wide as a stranger's cock slowly invaded my mouth. The stranger was dressed in a leather vest with leather pants and leather combat boots, all in black. The stranger was also wearing a black leather hood as well.

I was being split roasted as both Dominants worked me over. They took turns with my mouth and asshole. The stranger's cock felt familiar as the stranger fucked me. Eventually, Mistress took her strapon harness off and and forced me to lick her vagina to pleasure her.

As I was being fucked, I matched the speed with the stranger as I licked my mistress to orgasm on my face. Instantly, we all came at once. There was a loud pleasure moan let out by all in the dungeon. I collapsed in the chair, worn out and used.

Mistress and the stranger sat down and cleaned themselves with a wipe before zipping up their clothes. Currently, I was spent. Mistress removed my blindfold, and the light blinded me at first. I saw a black muscle man before me. I was surprised who it was. It was Carl. How does he know Mistress?

"Good evening, sissy. You are probably wondering how I know Mistress Linda here. Basic, she and I are partners in the club and her store. I helped trained her to be become a powerful Domme, " He explained.

" That night, I met you; it was set up by Mistress Linda. She figured, with you dressed as a female, you would come out of your shell. I proved her right," Carl explained.

"Now you have two choices: either serve both of us or take everything off and never come back to the club or the store again. You will never hear from me again, either," Sir explained.

"I want to say I am sorry for betraying your trust by setting you up with Carl. We have been friends for a long time. After we ended our romantic relationship, I noticed you were miserable and lonely. You were having a hard time figuring out your romantic life.," Mistress explained.

"You and I should have talked about your feelings before you decided to dress a woman for Halloween and go out in public. Please forgive me. I don't want to lose my friend. I understand if you don't want to continue this dynamic. I would love to train you for both of us if you can forgive both of us for deceiving you," Mistress said.

Yes, they deceived me and betrayed my trust. Deep down inside, I also understand Mistress's heart was in the right place. She has been right. I have been miserable and needed to come out of my shell. I thought about the proposal. They gave me a craving I wouldn't be able to quench. I made up my mind.

"May I answer, Mistress and Sir?" I asked.

They both said, "Go ahead!"

I said with a smile, " I would love to be trained as your sissy, please. I have this craving to serve you both, and I don't want to lose you."

They both smile. Mistress sat me up and had me stand up to remove the straitjacket. I am finally free from my bonds. As I was getting feelings back in my arms, Sir whispered something in Mistress's left ear, to which she said, " That is a good idea. Tell her."

" For your final test, how would you like to be a latex doll this Saturday for our Rubber Ball? " Sir asked.

"I gladly accepted, Sir," I said with a smile as I hugged Mistress to let her know i forgave her.

To be continued...