What Goes Around Comes Around - 2

*Authors Note: Annabelle Brito reviewed and made significant suggestions that have greatly improved the story. I wish to thank her for the time and effort she put in. Her contribution to this story can’t be overstated. The characters and events are from my perverted way of thinking. This is complete fiction and any resemblance to persons living or dead is pure coincidence. I hope you enjoy it. Please leave your comments, good or bad. I try to learn from constructive criticism. If you prefer you may email me at kjensen0611@gmail.com. I will answer all emails.

(Previously from Part 1)

I stood there stunned, unable to respond. She had tears in her eyes. I heard what she told me but was having trouble processing it. All I could think about was all the times we kissed, I was kissing a boy. I allowed a boy to give me a blow job and to masturbate me. I felt like my whole world had morphed into something I was not prepared for. 

“Please say something Mark” she begged. 

Tears were rolling down her cheeks and falling onto the carpet. She dropped to her knees and continued to cry.

“You really are a boy.” I said softly, in disbelief.

“I’m a girl!” she cried. “”I’m just in the wrong body, but I will have it fixed. You’ll see!”

Her tears continued to flow. I wanted to hold her and tell her it was alright but all I could think about was how I had been kissing a boy the whole time and I felt ill. I then made the worst decision in my life.

“I can’t do this Serena. I am not gay. Serena? Is that even your real name? Never mind, you don’t have to answer.”

I turned and walked out of her house hearing her scream “Please don’t leave me!” as I left thinking about how ‘she’ had lied to me".

(Part 2)

I barely made it home before I burst into tears. I lay down on my bed and cried myself to sleep. Mom woke me when she came home and took one look at me and knew all was not right in my world.

“You’ve been crying” she said. “Did something happen between you and Serena? Did she break up with you?”

“No mom” I said and started to cry again.

“Calm down sweetie and tell me what the problem is.”

I managed to pull myself together, sort of.

“Serena is a boy.”

“What? Say that again. I don’t believe I heard right.”

“She is a boy or rather he is a boy.”

“I don’t understand.”

“She says she is a girl in a boy’s body and will have surgery when she is 18. But mom, all along whenever I kissed her I was kissing a boy. It makes me ill just thinking about it.”

“Well, did you feel ill when you were kissing her?”

“No, of course I didn’t. I thought she was a girl and I loved kissing her.”

Then I broke out in tears again.

“Well Mark, you have to decide what you are going to do.”

“What do you mean? I ended it.”

“How did Serena take it?”

“She cried and begged me not to leave.”

“How did that make you feel?”

“Not very good, I was crying also.”

“Do you love her?”

“I did when I thought she was a girl. Now, I don’t know. Mom, I am not gay! I would never have kissed her if I knew she was a boy.”

I couldn’t tell mom about her jerking me off and how I played with and kissed her breasts.

"Try to calm down Mark, no one is saying you are gay, but it sounds like you may have broken Serena's heart, she seemed as if she really liked you and trusted you enough to tell you she was born a boy."

"I just don't know what to do now, I can't face her right now," I cried.

“I’m so sorry you are so sad Mark. But remember, whatever you decide to do, you have to live with the consequences.”

That was the end of the conversation. I thought she would be more sympathetic to me. She never brought it up again, nor did I. I moped around for a few weeks. I was fired from my job since I couldn’t concentrate and was making too many mistakes. Serena was always in my head. Although we had only been together for 3 months, it seemed that no matter what I did or where I went I thought of Serena. 

Whenever I thought I had made a mistake and should call her, the picture of her with her tiny prick and balls appeared in my mind. I didn’t think I could get past that.  Despite that I could not get her out of my mind. 

I’m not sure what caused me to change my mind, but several weeks later  I decided that I had made a terrible mistake. I needed her and knew that I could not live without her. If she had her surgery in 2 years she would be a girl. I decided to call her and beg her forgiveness and ask if we could start over. 

I called her and received the message ‘this number is no longer in service’. I went to her house and there was a ‘For Sale’ sign in the yard. I rang the bell and banged on the door but there was no answer. I walked around the house and found a window I could look through. The house was empty. They had already moved. I had no way to contact her. I sat on the front steps for awhile and cried.

My last hope was that she was still attending Jane Powers School. School was still 2 weeks away. I spent that time in mental agony. When I didn’t see her the first day of the new semester I asked at the office and they told me she had not enrolled for that year. They had no other information they could or would give me.

I watched my grades drop drastically but didn’t really care. When I would be taking a test Serena would pop into my mind and I would lose my focus. I somehow managed to pass all my classes but just barely. Mom wanted me to see a shrink but I refused. I told her I would work it out, but I didn’t. I dropped out of school at the end of the year and got a minimum wage job. 

Mom told me to seek professional help. I ignored her and told her to mind her own business. She was disgusted with me and when I turned 18 she told me to get my shit together or she would kick me out. I didn’t. She did. She told me it was tough love and when I was ready to move on she would welcome me back with open arms.

I found a room to rent but between the rent and food I had little left over. I changed jobs frequently over the next couple of years. The jobs got worse every time I either got fired or decided to up and leave. 

Then Mom almost died of a heart attack. I was unable to care for her, so her cousin in Centerville took her to live with her in her apartment. Her cousin saw what a mess I had become and would not allow me to see her. I don't blame mom for keeping her distance from me. I was a total mess and would have only upset her. She was 42 and far too young to experience that. I felt awful letting her down like that without attempting to reconcile with her. I knew deep down that she wanted only the best for me but I refused to listen to her. I considered offing myself but didn’t have the courage. 

I drifted through life for the next several years with Serena never far from my mind. I knew I was obsessed with her, but could do nothing to change it. I lived with her ghost and the beautiful memories we had before I destroyed it. 

I often wondered what became of her, did she find happiness? Did she marry someone? Did she complete her transition? Did she hate me? Was she dead? ….. Did she even remember me? 

Working at an office furniture warehouse was the only job I could get that had decent pay and somewhat mediocre benefits. One day, we had an order to deliver and assemble an office desk at the Jane Powers School. 

 

It was weird going back. I noticed that the photo of my coronation as the winner of the first ever womanless beauty pageant was featured prominently in their glass case. 

There was a lot going on in the office that day. I overheard that they were holding a carnival that night and the new recently promoted principal wanted to impress representatives of their school's sponsors as well as potential donors. 

While installing the desk I noticed an open room with boxes labeled, "Permanent Records: Student Confidential " each with a year.  The boxes were from the last decade. I was tempted to look through, but with people coming in and out realized I would be caught. I heard one of the office ladies mention that the office would be open during the carnival, so the staff and VIPs could use the restrooms instead of the port-a-potties meant for parents and students.

I was still so obsessed with Serena that I decided that that night would be a good opportunity to sneak in the office and find any information of what happened to Serena. 

Most of the carnival was being held outside. I should have tried to dress less suspiciously, but I went into the office side door in my black jeans and black hoodie. Little did I know I was spotted entering via one of the security cameras on site which had been installed sometime after I left school and was being monitored. It was another stupid decision I regretted making. When I heard someone approaching the record room, I quickly ran out and tried to get out through the window of the office administrator. Unfortunately, it couldn't open the whole way up and I got caught halfway out effectively trapping me. I tried to break free, but my jeans were caught on some kind of clip of the window. I couldn’t get back nor could I go forward. I was trapped. Being trapped in the window frame with my butt exposed was beyond embarrassing.

After being picked up by police, I was held in an interrogation room with one hand cuffed to the bar on the table.

It felt like I had been waiting for hours for someone to enter through the metal door. Finally a woman came into the room. 

"Mark Taylor, I am Sarah Bennett, an attorney. I am the sponsor for tonight's event at the school you tried to rob earlier tonight. You are in deep trouble, trespassing and attempted robbery on an important night at the school!" said the fairly attractive woman. 

"Wait, I wasn't going to rob any-" 

“Please let me finish Mr. Taylor. I am also the attorney representing the school and I am cautioning you that you do not have to say anything to me and, in fact, I would advise you not to speak to me but to get your own attorney. All I ask is that you listen to what I have to say."

I nodded.

"Thank you! Now you may not know this but you will be charged with trespassing, illegal entry, and attempted robbery just to name a few things. You were caught on video breaking and entering, we have you on camera. You are looking at a maximum of 10 years in a correctional facility."

"Wait! No! I was simply trying to find information on a friend."

She looked at me with silence, but was clearly skeptical. 

"Mr. Taylor, in light of the fact that you are a former student of Jane Powers School, they would prefer not to press charges. They would require, however, that you perform community service for a period of no less than 5 years.”

Thinking only that I could avoid prison, I replied “I’ll do it!”

“I really think you should talk to your own attorney.”

“I can’t afford an attorney. I will do public service. Now can you get me out of here?”

“If that is what you want let me make you an offer. I represent non-profit organizations like the Jane Powers School. I would take you on as my assistant. Note that should you not work out, that is if fail at your job, or leave before your term is up, we will press charges and you will go to prison. Do I make myself clear?

“Yes ma’am.”

The choice was clear, be sent to prison for up to 10 years and become some crazed prisoner’s wife or sign over 5 years of my life as Sarah's personal assistant. There really wasn’t any choice. The court had me sign a paper stating that I would abide by the terms which Ms. Bennett offered me. She would be the sole judge of whether or not I complied. After signing the document Sarah held out her hand to me.

“Welcome Emma!” she smiled.

“Emma? Why do you call me that?”

I am an alumna of Jane Powers School. I graduated the year before you started and was at the beauty contest which you won. When I saw your picture in the office I realized that you were the same Mark Taylor who won that contest.

“OK, but why call me Emma? That was a one night stand. My name is Mark.”

“I’m afraid that it will be more than a one night stand. You will be my maid and I will call you Emma” she said with a big grin.

And this is how I met and came to work for Sarah Bennett.  I moved into her house as her live-in maid. My wages consisted of room and board and clothing, the latter of which consisted of maids’ uniforms. I had no spending money of my own, though she told me she would deposit $100/week into an escrow account payable when I had served my time.. My working uniforms consisted of a knee length black a-line dress with a white pinafore, black opaque stockings and black court shoes with one inch heels. Underneath I wore panties, a bra, and a full length cotton slip, all white. Sarah set up a schedule of chores for each day of the week. 

I was to finish my chores by 4:00, bathe, and change into one of my French Maid dresses of which I had 5 of different colors, opaque hose that matched the dress I was wearing and 4 inch black stilettos. I would prepare and serve dinner to Sarah who usually got home about 6:30. I was totally emasculated and often wondered if I wouldn’t be better off in prison. 

Sarah was strict and hardworking and was actually quite pretty. She was already a highly successful attorney. It was not long before I became attracted to her. 

As far as I could tell, Sarah had no social life, so we spent many nights and weekends together. In some ways she reminded me of Serena. She had the same bubbly personality and take charge style. She was loaded with self confidence whereas I had none. After a time we became lovers. As a result of my low self esteem I always followed her lead. 

She allowed me men’s clothing when we went out together, but she kept it locked up at other times. I knew I looked like an effeminate man but it was a relief to wear trousers even for just a few hours at a time.

Then an incident happened that changed our relationship. I had just turned 25, had done nothing with my life. On our way home from a matinee at the theater, we were in a minor traffic accident. Sarah had been driving. I was in the passenger seat. The man driving the other car was rude, cursing and threatening her. I sat in the car wallowing in self pity and never moved. When we got home she was angry. I knew she wanted to talk about the accident and it made me very uncomfortable. I was not proud of how I behaved but at the time I felt paralyzed and to be perfectly honest I was afraid that the man would strike me, considering how effeminate I looked.

“So Mark, what do you have to say for yourself?”

“What do you mean?”

“That man was rude, cursing me, threatening me and you never got out of the car to defend me. Why not?”

“Well, I didn’t…”

“You’re a coward!”

“As I was saying …”

“I don’t want to hear it. Get out of my sight. I am too angry. I need to calm down, but don’t think you’ve heard the last of this.”

I knew that when she was like this it was best to avoid her. I retreated to the living room intent on reading, but with her in such a state I was unable to concentrate. I feared she would throw me out. If she did I would either be destitute or go to prison.

We ate dinner pretty much in silence. After we finished eating she told me to come with her to her study. She seemed to have calmed down, but I was still nervous about facing her. She sat in her accustomed place behind her desk and I was in one of the guest chairs opposite her. The chairs were designed so that anyone sitting in the guest chairs was looking up at her. She claimed it gave her a psychological advantage in any business negotiations. I was certainly at a disadvantage in this meeting and having to look up at her did not help.

“Your behavior today convinced me of something I have been thinking about for some time. You really aren’t a man at all. You act like you hate wearing dresses but you are not capable of functioning as a man. You may be a male but you’re not a man! In fact, I am more of a man than you are and I don’t think anyone would call me masculine in any way. Do you?”

“How masculine can I be when you make me dress as a woman?” I asked ignoring her question and feeling really hurt.

“You never initiate sex. If I want sex I have to initiate it. Why is that?” 

“I..I don’t want to impose myself on you.”

Providing sexual relief for her was something I didn't fully enjoy as I always thought of Serena, but signing that contract obligated me to serve Sarah and all her needs.

The first time we did it was after cleaning her house and running errands one day for her. She called me into her bedroom that night asking for a massage. I was shocked to find her on the bed lying down wearing a nighty.

When I asked her what shoulder she needed a massage, she smirked and  replied, "Silly, it's here!"

She then lifted her nighty and showed me her pussy. 

"It's been a long day at the office and I badly need some relief."

This then became a ritual almost every night. She would direct my head to pussy and have me tongue her asshole. Later she would have me start wearing a condom and have sex with her. I often had trouble maintaining an erection. She was always on top. I always thought of Serena as Sarah humped me. This wasn't exactly making love. She was using me like a woman uses a sex toy for private satisfaction. 

"Oh please, you should be lucky that I even allow you to touch me. Most men would kill to have sex with me!"

"I just don't want to take advantage of your kindness.”

I knew it was bullshit and suspected she knew it also but I did not want to tell her the real reason, which was that she was not Serena. I was afraid she would throw me out if she knew and that would most likely send me to prison. 

“When we do have sex I am always on top. You can’t keep an erection when you are on top. And when I am on top even then it’s 50/50 whether you stay hard enough to satisfy me. Fortunately you have a talented tongue. At least that stays wet and hard! I feel like I am the man in this relationship. What do you have to say to that?”

“I..I…”

Then I started to cry.

“You are a sissy. I should have realized that when you took to wearing your maid’s dresses so easily, but did not make the connection till now. Now I know how you won that beauty contest. It was natural for you.”

“I’m not a sissy” I replied with little conviction. 

“Really?”

I felt extremely vulnerable at that moment but did not know how to answer her.

“Wh..what are you going to do?”

“I don’t know. But for now you can sleep in the guest room. I don’t want to see you. Good night Mark! Oh and clean up the kitchen before you go to bed!”

With that she went up to bed. I cried a bit longer and then poured a glass of wine to calm myself down. I knew that everything she said was true but her verbalizing it brought it all into the open and made me face the fact that I really was a failure as a man.

I went up to the guest room and realized that I had no pajamas there. I hoped she wasn’t asleep when I knocked on her door.

“What is it?” she called through the door.

“I..I need to get my pajamas. The only ones in there are your old ones to be given to the church charity collection.”

“You can wear those. They should fit you ok. In fact, you should get accustomed to wearing them. You will no longer wear men’s pajamas in this house.”

I tried the door but Sarah had locked it. The only pajamas I found were frilly baby dolls. There were a couple of sexy nightgowns as well which she no longer wore. Knowing how she detested my sleeping naked, and not wanting to piss her off any more than she already was, I selected the plainest pair of baby dolls. They still had some lace on them but were dark green, not a pastel that the others were. As soon as I pulled the panties over my cock I had an erection. It was no surprise, I got an erection every day when I put on my panties.

I knew it would not disappear on its own. I lay down on the bed and I jerked off, culminating in ejaculation into my dainty panties. That tired me out and I fell asleep almost immediately.

I was awakened the next morning by Sarah. She knocked on the door and walked in. I had fallen asleep on top of the blanket and had been sleeping on my back. The stain on my panties was quite obvious to her. She started to laugh.

“So my sissy boyfriend is turned on by wearing pretty panties and a pretty baby doll. Why am I not surprised?”

I was too embarrassed to say anything.

“Come into the kitchen. I have to talk to you before I leave for work.”

“OK, but I’m going to shower and put on some clothes first.”

“No, I am not going to wait for you.”

“It was your idea that I wear this. I’m going to shower first.”

She grabbed my arm and surprised me with her strength by pulling me out of bed. She then twisted it behind my back and slapped my ass a few times. I could not break free and wondered how she could be so strong. Still holding my arm behind my back she marched me to the kitchen. It was still a mess from last night’s dinner. 

“I told you to clean up the kitchen last night. You are trying my patience.”

She surprised me then and pulled me across her lap. She pulled down my panties and spanked me hard. It took only 4 or five strokes before I was crying, reinforcing her belief that I was a sissy. When she finally allowed me to stand it took me several minutes to get my crying under control. She sat there with a big smile on her face.

“I want this kitchen cleaned before I get home tonight or that will seem like love taps. Do I make myself clear?”

 “Yes ma’am.”

“I will inspect it when I get home and there will be consequences if I am not happy. Do you understand?’

“Yes.”.

 “Good, I will see you tonight.”

When she came home she ordered me to follow her to her bedroom. There she ordered me to drop my panties and lie down on the bed. She lifted my dress and took a box from of the bag she was carrying. The box contained a pink plastic device. It had a tube with a ring attached to it. She put the ring around my balls and then fitted the tube over my penis. With a small lock she connected the ring to the tube and closed the lock.

"Hey! What the hell is this?" I replied in horror as I saw what she did to me.

She slapped my face aand said “You don’t talk to me like that.”

Then she examined her work and frowned.

“That was the smallest device they had but it is still too big. I guess it will have to do. You will not be able to achieve an erection with this device on and you will have to pee sitting, like a girl, which you should be doing anyway.”

“Sarah! How can I take that thing off?” 

“That's Miss Sarah to you!”

“Huh?”

You will address me in the future as Miss Sarah or ma’am!”

I was bristling with anger, but fully cowed by her I replied, “Yes ma’am.” 

Sarah smiled and nodded with approval.

"How can I take this thing off, Miss Sarah?”

“I have the keys. You will have to earn your release.”

“Why have you done this?”

“It is obvious that you are incapable of doing your job. You have a contract to fulfill and I want to make sure you fulfill it. If I am happy with your work as my maid you will be allowed ½ hour each week free from your cock cage so you can play with yourself.”

I burst into tears from the humiliation.

 “Do you know how to curtsey?”

No ma’am!”

“Don’t lie to me! I saw you curtsey to the judges at the beauty contest!”

The thought of it brought tears to my eyes.

“I’m sorry Miss Sarah, I did curtsey once before.”

 “Don’t ever lie to me again!”

“No ma’am I won’t.” I replied and dropped another perfect curtsey. 

I knew I had to get out of there but how? I had no money, no job, no access to men’s clothing, and no home. If I left without her permission I could go to prison. I was truly fucked. My only hope was to beg Sarah to release me but I was certain she would turn me down. I decided I would go along with this charade and hope to ask her when she was in a good mood. 

I continuing serving as her maid for the next few months. I found that I really did not mind doing the housework. Though somewhat physically taxing it did give me a sense of accomplishment. It would almost have been enjoyable if I could wear sweatpants and sweatshirt instead of the maids’ dress and feminine accouterments. 

Sarah left me a list of chores each day and inspected my work when she came home. I received demerits when it was not satisfactory. If I acquired too many demerits I was not allowed release. On a good week she would unlock my cage cock and allow me to masturbate. Though I was extremely horny I was only able to get one release in the time she allotted me. Sarah would often watch me masturbate which added to my humiliation as she found it entertaining. I was often unable to cum in front of her.

Before she arrived home in the evening, I had to change into one of my French Maid’s dresses and 4 inch stilettos. I wore it to serve her dinner and was at her disposal until she went to bed.  The only clothes I had to wear were my maids’ outfits. She had thrown out my men’s clothing. While my working uniforms were simple black dresses that I could have worn in public without the aprons, I feared being discovered as a man in a dress so I was confined to the house.

One day Sarah announced that she would be having a prospective client join her for dinner. 

"Everything has to be perfect tonight. If I can convince this client to hire me with a retainer it could be a real game changer for my firm. Don't embarrass me Emma!"

"Yes, Miss Sarah, I understand," nodding my head. 

That night I made sure the home was presentable for Sarah's important guest. The table was set with her finest dishes and sterling silver flatware which I had spent hours polishing.

She was happy with what I had done. The doorbell rang and Sarah cautioned me.

"There she is, don't forget how to greet our guest."

I opened the door and dropped my curtsey. 

"Oh I didn't expect, such a lovely welcome," said the lady.

I looked up, and I was stunned when I realized the client was Serena. I stayed down in my curtsey frozen with my mouth open, unable to speak. 

“Aren’t you going to allow me to come in?” asked Serena.

She was smiling at me and had a twinkle in her eye which I remembered so well.

“Yes ma’am, I am sorry.”

I stepped aside, feeling totally humiliated to have her see me like this. She oozed confidence and dignity, a huge contrast to my current position.

Serena was more beautiful than ever in her feminine white power business suit with her long straight hair hanging.  Any thought I had that I could stop loving her was for naught. She smiled at me and said “Hello Emma.”

“Emma?” asked Sarah “How do you know my maid?”.

“We go way back” replied Serena. "It's a small world."

“You will have to tell me” said Sarah smiling.

She turned to me and said “I’ve ordered dinner since your cooking is not yet up to standards for me to serve to guests. You will answer the door when the bell rings, put it on serving plates, set the table with 2 places, open a bottle of wine, and serve up the wine and food.  The meal has been paid for but don’t forget to tip the delivery person.”

“Yes ma’am” I said curtseying.

Sarah reached into her wallet and handed me money for the tip.

“Oh, and curtsey to the delivery person, male or female!”

“Yes ma’am” I replied and dropped another curtsy.

I was so embarrassed having Serena see me dressed like a maid and being treated like this. I had often envisioned meeting her again, but certainly not like this. What must she think of me?

The delivery boy who could not have been more than 17 laughed when I curtsied to him after opening the door. He could not take his eyes off me. It made me nervous to think he might have realized I was a man though he said nothing. He thanked me for the tip and left smiling at me.

I served them dinner while they discussed business. Though Serena looked at me and smiled she said nothing to me and I was afraid to try to talk to her. After I washed the dishes Sarah dismissed me for the night and told me to go to bed. 

The next evening Mistress Sarah came home alone. I served her and stood in a corner with my hands folded in front of me in case she wanted something which was my normal behavior. The rest of the week followed a similar pattern. 

When she came home on Friday night she said to me “Ms. Brogdon wants you to work for her. She has made it a condition of hiring my firm to represent her. I agreed to her terms conditioned on your agreement as well. I told her I would ask you, since you are not my slave. If you go to work for her it will be of your own free will. Do you agree?”

I couldn’t help but get excited at the prospect and hoped Serena was doing this so we could be together.

“Yes ma’am and thank you ma’am,” I replied while I dropped a curtsy as I had been conditioned to do.  

“Will you allow me to go to her in men’s clothing? All the clothes I have are these maid uniforms and female underwear and lingerie. You can’t expect me to go there dressed like this!”

“No, I have already disposed of the male clothing I was keeping for you. What you wear is of no concern of mine. All I know is Ms. Brogdon wanted you. I will call Uber for you. The driver should be here soon. Take your uniforms and lingerie, I will have no use for them.”

I changed into one of my work uniforms minus the apron. Though very short, it was far less sexy than the French maids’ dresses. Then I went to say goodbye to Sarah.  

She gave me a hug which surprised me. She talked kindly to me for the first time in many months.

"In a weird way, I'm going to miss you," she said. “It was good for awhile Emma. I really do wish you good luck in the future.”

I looked at her with surprise.

"Yes, Ms. Brogdon told me a bit about you Mark. Now go to her, she is waiting."

I couldn’t help but get excited at the thought that Serena was waiting for me, I had a big smile hearing that statement.

I thanked Sarah and then cursed myself when I dropped a curtsy to her.

The Uber driver kept looking at me in the rear view mirror. It felt like he was undressing me with his eyes. He had plenty of time to look at me since the drive from The City of Adams to northern Centerville was almost an hour. I breathed a sigh of relief when I finally reached Serena’s large yellow two story home. Though I did not know what to expect, it had to be better than the nightmare I was living at Sarah’s house.

My heart dropped when I saw two high end cars in the driveway, surely one of them belonged to a successful husband!

I took a deep breath and rang her doorbell. 

Serena opened the door and gave me a big smile and a hug. Our holding each other felt to me like we had been transported back 10 years. She kissed my cheek and stepped aside so I could walk into the house.

“So good to see you again Emma. Drop your bag and come in. We have a lot to talk about.”

She made us coffee and we sat at the kitchen table opposite each other. She asked about my life and I told her the unvarnished truth including how my mother had been taken away from me and my estrangement from her. I told her that I would try to get my life straightened and I wanted to start over with her, if she would have me. 

“A lot has changed since we last saw each other. I'll be as honest with you Mark as I was when I revealed my secret to you. You walked away from me that day. It made it difficult for me to trust people again. It took me a long time to get over that. We will have to see how it all plays out between us”

“You’re right, of course” I said unable to look her in the eyes.

“How are your parents?” I asked.

“My mom is good. My dad is gone. They were in an auto accident, and he was killed by a drunk driver who got out without a scratch.”

“I’m so sorry Serena.”

There was silence for a couple of minutes while we got lost in our own thoughts. 

“You really hurt me Mark! I was so much in love with you and I thought you loved me too. Your comments made me feel so small, so unworthy.”

She had tears in her eyes.

“I know” I replied and could feel tears forming in my eyes. “I know it’s no consolation but I hurt myself also. I tried to contact you to apologize and hopefully attempt to repair our relationship but your phone had been disconnected and your house was empty, up for sale.”

“Yes, my dad bought this business here in Centerville and didn’t want to commute. I finished high school in an all girls Catholic School, ironic, isn’t it?”

I nodded.

“As I said, it took me a long time to get over you, but I did and moved on with my life. I graduated with honors and a week later I had my first surgery. It wasn’t easy but now I am a woman, well, except for being unable to have children.”

I said nothing, beating myself up for not believing in her. 

“I took a gap year to complete my gender change and then went to college. I completed my bachelor’s in 3 years and my master’s the following year. Then I took over my father’s business after he died. Its profits now are higher than ever and still growing.

“I met Sarah when representatives of the Jane Powers School approached me and other heads of business about sponsoring future events and funding potential school programs. It's something I have been considering. I have a love/hate relationship with that school. I'm sorry this business talk must be boring you.”

I told her that I had the same feeling about our school days. I looked at her and had to ask her a more important question.

“Do….do you have a….husband, a… boyfriend?”

“No and I never married,” she replied. "I’m just married to my work, I guess."

“Do you have any feelings at all for me? Do you still hate me?”

“Emma, I never hated you. A part of me understood where you were coming from. I did not handle it well either. When I think of our previous relationship I dwell on the good times and the fun we had.”

Maybe there was still hope for me, I thought.

“Why did you want me to come here?”

“I was wondering when you would ask that. I did not like the way she treated you. I don't know her personally, but I have heard from some people that she can be a real bitch. I will be blunt however, I do need a maid!"

My mouth dropped open in surprise. 

"I hope you will serve in that capacity. I won’t force you if you do not want to be my maid. In any case I will tear up the contract and you will be fee to live your life as you see fit.”

Should you decide to stay, our relationship will be employer and employee. Your wages will be your room and board and medical care. I will also pay you $200/week. I do not want you beholden to me. Think of it as a favor for an old friend. You will have Tuesdays and Thursdays off. Is there anything else you need to know?”

“Umm…did by any chance, did Sarah told you about…" I stammered.

"Your chasity cage? Yes, I know. She told me all about it. I have the keys"

"Will you remove the chastity cage?”

“If you do not want to be my maid and choose to leave, then yes, otherwise no, at least not yet. I want to think about it. When I decide I will let you know.”

I nodded my understanding. I didn't want to risk losing Serena again. 

“That is a small bag you are carrying. You don’t have much in the way of clothes.”

“Sarah took all my male clothes and got rid of them. All I have is the dress I am wearing, another like it, a few French maids’ dresses, some lingerie and another pair of shoes.”

“We will go shopping tomorrow and I will buy you some regular clothes. Do you have any more questions for me?”

“No. I am tired. Do you mind if I go to bed?”

“Grab your bag and I will show you to your room. Being the weekend, I expect my breakfast to be on the table at 8:00. On weekdays it should be there at 7:00. You should be dressed in your work uniform, makeup, and hair done for the day. I normally have a small glass of juice, toast with butter, and coffee. I will let you know when I want something different. I’m afraid the kitchen is a bit of a mess. Please clean it before I come in for breakfast.”

My room was a bit bigger than the one at Sarah’s and had an ultra feminine décor. I was so tired I didn’t care. I stripped, used the toilet, and put on the only night clothes I had, the baby doll gown which got me into trouble. Yes, it had been washed. I was out like a light.

I neglected to set an alarm and as a result I didn’t wake up until 7:30. Since it was Saturday I didn’t have to have Serena’s breakfast ready until 8:00, but there was no way I could shower, dress, put on my makeup, fix my hair and have her breakfast on the table at 8:00. I had screwed up royally on my first day. 

It was 8:35 when I finally made it into the kitchen. Serena was sitting at the table drinking coffee and was not happy. When I entered she just pointed to the clock and shook her head. I knew I was in trouble. 

“Is this what it is going to be like Emma? If so I might as well terminate you now.”

“Please Serena, give me another chance. I forgot to set my alarm. I promise it won’t happen again.”

“You do realize your mistake will cost you. I can’t let my maid think that she can do whatever she wants when she wants, at least not when she is on duty. We are friends, but as my employee you must follow the rules.”

“I understand Serena. I am so sorry.”

For some reason I dropped a curtsey to her. She smiled.

“That was very nice! I think you should do that all the time when I give you an order, when you report to me, when you leave the room, and whenever you speak to me. What do you think?”

What I thought was that I wanted to tell her to go fuck herself and leave, but aside from being impractical, it would mean that I would be blowing any chance I might have of being with her, and I desperately wanted to be with her. I figured that maybe she was getting even with me for the way I treated her.

I swallowed what little pride I had and replied “Whatever you wish ma’am” and dropped another curtsey.

She smiled at me. 

"I was kidding. That was one of the things I disliked about the way Sarah treated you. For now, fix me my breakfast and then get to work cleaning the kitchen. You may eat when you are done with that.”

“Yes miss” I replied and dropped another curtsey to her.

She laughed and I turned beet red. Serena was not kidding when she told me the kitchen was a mess. It took me almost 2 hours to clean it up. She was happy when she inspected it.

“Good job Emma. Ok let’s go and get you some every day clothes.”

“All I have to wear is my maids’ dresses. Do I have to go shopping in one of those?”

“No I will loan you something to wear. You are perspiring. Take a shower and I will find something for you. One thing you need to know is that as long as you live with me you will wear only skirts and dresses.”

“Oh. I was hoping I could dress as a guy, at least some of the time.”

“No! I like my men feminized. I have no interest in masculinity. We will be shopping for girly clothes for you. Is that going to be a problem?”

“I..I don’t know” I replied feeling very dejected.

“Well you better decide quickly. If you want male clothing I will buy you some but you will have to leave.”

I couldn’t lose her after spending all these years looking and hoping to find her.

“I will wear female clothes for as long as you want me to.”

When we left the house I was wearing a very short read a-line skirt with a white cotton petticoat, and a yellow blouse. My petticoat showed every time my skirt moved which I found quite embarrassing. 

I tried on many dresses, skirts, and blouses before we, or should I say Serena selected for me. She bought me several new dresses, skirts and blouses. Why I needed that much clothing when I couldn’t go anywhere I didn’t know, but Serena insisted. I was afraid to argue with her for fear that she would tell the sales girl my true gender, but she never said a word. As far as I knew the sales girl did not know that I was a male.  I relaxed a bit after that and our next stop was for lingerie. Serena claimed I did not have nearly enough. A sales girl approached us as we entered the lingerie section.

“Good afternoon ladies! May I help you?” she asked

“Yes please, my boyfriend needs to be fitted for some new bras and he doesn’t have nearly enough panties.” Serena replied as she pointed towards me.

If a hole opened up in the floor and sucked me in I would have been grateful. Instead I just stood there. The girl looked shock for just a moment but recovered quickly.

“Did you say your boyfriend?”

“Yes, he is such a sissy, but I love him and want him to be happy.” Serena smiled and kissed me on the mouth.

Despite the embarrassment I felt at her revealing my gender I was in heaven from her kiss and her saying ‘I love him’. I only hoped it was true.

 “Come with me sweetie and I will measure you. Bras are so uncomfortable if they don’t fit properly. I will get you measured properly and you will have bras that are so comfortable that you will not even be aware you have them on” the sales girl said as she took my hand and led me towards the fitting rooms.

“I will pick out some panties for you Emma and meet you back there.” Serena told me.

“Emma is such a pretty name. Did you pick it?”

“N..no, Serena, my girlfriend did.”

I was shaking I was so nervous.

“No need to be nervous Emma. If your girlfriend hadn’t told me I would never have guessed you are a man. I will keep your secret. By the way my name is Kim.”

She led me into a fitting room and closed the door. 

“Take off your blouse and bra so I can measure you.”

She said nothing about my breast forms but went to work with her tape measure. 

“Stay right here and I will bring back some bras for you to try on to be sure of my measurements. Once we know that we can go back and pick out some pretty bras for you.”

She determined that with the breast forms I wore a 36C bra. She came back with several bras for me to try on. While I was doing that Serena came in with a dozen pairs of panties. It looked like she picked out the girliest ones she could find. They were a mix of pastels and flower patterns held together by the laciest of fabrics.

I put my bra and blouse back on and we went out to look at bras for me to pick out. Serena and Kim accompanied me and told me to pick out some I liked. I selected the plainest ones I could find but was over ruled by the girls. I wound up with 6 bras covered with lace in the various pastels that matched some of the panties that Serena had chosen. My embarrassment increased when I had to try on each and every one in front of the girls.

The final stop was for shoes. The shoe salesman fitted me and brought out shoes for me to try on. While sitting on the low stool helping me he kept glancing up my skirt. This made me uncomfortable and I prayed he could not see my panties. Strangely enough though, it caused me to try to get erect inside my cock cage.

We were both exhausted when we got home. Serena told me to put my new clothes away and change into my French Maid’s dress while she ordered pizza. I had to serve her but she allowed me to sit and eat with her. We had a very friendly conversation.

The following week went fairly smoothly. Tuesday, though technically my day off, I served Serena breakfast. I pointedly wore one of my new outfits quietly stating that I wasn’t on duty.

“You didn’t have to do this Emma. You know I meant it when I said you are not on call on your days off.”

“I just want to thank you for all you have done for me. Though I am technically your maid, you treat me as your friend. No one has treated me so kindly in a very long time.”

Not having any male clothing I wore one of my new dresses and just lounged around all day reading some of Serena's fashion and celebrity gossip magazines along with watching day time soaps which I quickly got addicted to. I wanted to go someplace, but even though I passed pretty well as a female, the fear of being discovered and making a mistake that would reveal my true gender never left me.

Things went smoothly for a couple of weeks. Serena treated me much better than Sarah had when I was her maid. It felt like we were getting closer, but there was no physical contact between us.

One morning while serving her breakfast she told me to get something to eat and sit with her.

 “We are friends Emma. I hope we will stay friends. I have missed you all these years. I hope we can remain friends. I don’t have time right now, but I have something important to discuss with you. It will have to wait until tomorrow. I think you will like what I have to tell you.”

She kissed my cheek as she was leaving for work. I was floating all day.

She called me mid-morning and said “I am having a potential client join me for dinner tonight. You will have to be a maid for dinner. After cleaning up you will be off duty and I request you go to your room. To make it up, you may take tomorrow off.”

I wore my French maid’s dress and greeted Serena's guest with a curtsy when I opened the door. I don’t think I had ever felt as small as I did at that moment. This large man in a dark blue business suit, unnerved me, clearly undressing me with his eyes. 

Serving him dinner was even worse. It seemed that whenever I was near him he would lightly graze his hand on my butt checks and run his hands up my legs under my skirt. The worst part for me was that each time he did something like that I would start to get erect. I did not think I was attracted to men but what he was doing was certainly arousing me.

I wasn’t sure if Serena knew what he was doing to me but she said nothing.

While placing the dishes in dishwasher, I heard our guest changing the discussion of sales reports to repeatedly commenting how lovely Serena looked in her gray business outfit.

"I'm flattered, but, I'm not looking for a relationship right now, plus it's getting late," she said.

"Yeah…uh…lets continue tomorrow over a video conference?" he said.

“That won’t be necessary. I don’t believe we can do business” Serena replied.

He was not very happy when he picked up his laptop and left.

I was relieved after he left. I cleared that table and retreated to the kitchen, with the realization that Serena could have any man she wanted and there would be no shortage of potential suitors.

The next morning was my day off, but I got up early to eat breakfast with her. I hoped she would talk to me, but she had some contract to read over breakfast and other than a greeting we had no conversation. After she ate her breakfast she made a point of washing the dishes and wiping off the table and kitchen counter, emphasizing that it was my day off. 

“I will be home early and we will talk.” 

I was relaxing with a book when a couple of hours after she left the doorbell rang. It was her client from the night before. 

"Hi, is Serena home?"

"No, she is not."

"Oh, darn. Well I just wanted to tell her I decided her proposal was excellent."

"Oh good, I guess," I weakly answered.

I was puzzled. I thought I heard her tell him they would not be doing business.

"Yes, it will be a mutual benefit for both sides. Also I may have left a file with sales information here on her table or living room, would it be okay if I come in?"

He then pushed me aside and walked into the house. He closed the door and I noticed that he locked the door quickly.

Before I could say something he grabbed me and kissed me. It was not a chaste kiss. He pushed his tongue into my mouth! After a struggle I finally was able to push him away. 

“You better leave now!” I demanded.

"I was hoping to have some personal fun with Serena before I leave town tonight, but you will have to do."

He twisted my arm behind my back and told me if I screamed he would break it..

“You have been asking for this since I got here last night the way you were flirting with me, shaking that ass in that sexy dress you were wearing.”

“I wasn’t” I cried.

“Well I disagree, and now I’m going to give you what you asked for!”

He slapped my face, ripped off my dress, petticoat, and panties. He was not happy to see the cock cage. 

“What! You’re not even a girl!” he said shocked.

"Please leave!" I begged looking away.

"I don't know what kind of freaks Serena keeps around, but it doesn't matter. I’m horny as hell so you will have to do.”

He slapped my face a few more times before he dragged me over to the sofa and threw me onto its cushions. 

He told me not to move and quickly removed his pants and boxers displaying a cock that even semi-hard was far larger than mine with a full erection.

He turned me on my stomach and spread my legs apart. He put a couple of couch pillows under my groin forcing my butt up. Lance then spanked my butt emphasizing his control.

“Hold still! I'm going to enjoy this sissy girl.”

Being pinned to the sofa, all I could was to lay there crying as I felt his erect cock touch the opening of my asshole. Then he entered me and he was not gentle. The pain was excruciating and I continued crying. When he finally came he collapsed on top of me. He lay on top of me for awhile pinning me to the sofa. I lay there crying not wanting to look at him. He started to put on his clothes when I heard the front door open.

“What the hell!” cried Serena.

“Nice of you to show up. Your maid was very accommodating but I have plenty left for you, you bitch!”

“Serena run!” I cried hoping she would get away from him.

Then I heard a scuffle and a scream and then a body falling on the floor. I couldn’t bear to look and was too weak to help Serena. I realized the scream was not from Serena. I looked up and saw Lance on the floor holding his groin. There was also blood streaming down his face onto the carpet. Serena looked untouched.

“What happened Emma? Are you alright?”

I couldn’t speak and just lay there crying.

Lance tried to get to his feet but Serena kicked him in the head and he fell unconscious.

 “I rolled over onto my back and began to cry.”

“I am going to tie this asshole up and I will take care of you. Ok?”

I nodded. Serena disappeared and returned with some thick rope. She hog tied him and gagged him. Then she held me close and we both cried until there were no more tears.

“Tell me what happened Emma” she said softly.

My body was sore from his slaps and strikes. I told her what Lance had done to me and more tears came as I relived it. She just held onto me and said nothing. Finally I stopped. 

“I have a phone call to make. Then I will help you.”

“Please don’t call the police! I couldn’t bear to have them see me. I just want to forget the whole thing.”

“I am not calling the police.”

“What…..how did you beat up Lance?”

She smiled at me.

“When I told my parents that I was a girl and when they accepted it, my dad enrolled me in Martial arts courses. He anticipated that I might need to know self defense. I have black belts in karate, jujitsu, and tae kwan do. Now let’s get you cleaned up I will take care of you.”

Serena helped me to my feet and helped me into her bathroom where she had a large soaking tub. She filled the tub with warm water and added some feminine smelling bath salts and bubbles. She removed what clothes were still on me, told me to wait there, and left the room. She returned about a minute later with a key and removed my cock cage. To my surprise she put both the cage and the key in the trash. 

“We will not need that any more” she stated.

She helped me into the tub and told me to relax. I was still upset and didn’t think much about what she was doing. She told me to just sit and enjoy the bath and left the bathroom for a second time. 

I heard her talking on the phone. She was gone about 20 minutes and I heard the door bell and voices but couldn’t understand what was being said. When she returned she was in white panties and a white bra. She carried in some lingerie which I recognized from our trip to the mall. She looked magnificent. As she had said, she was now a woman. 

She kneeled by the side of the tub, grabbed a wash rag and soap and gently bathed me. I found myself relaxing under her touch, almost forgetting my trauma. When she finished bathing me she had me stand and rinsed me off. She held a big fluffy towel for me to step into and patted me dry. She held out panties for me to step into and then dressed me in a waltz length silk gown.

 “We need to talk. Do you want to lie down for awhile first?

“No Serena.”

She took my hand and led me into the kitchen and had me sit.

“Would you like some tea or coffee?” she asked me.

“Yes coffee, please. I will make it.”

“Sit sweetie. I will make it after I grab a robe.”

She was being very affectionate to me, more affection than I had felt from anyone since we broke up those many years ago.

“Emma, I need to apologize to you for what Lance did to you. I saw the way he grabbed you last night. That was why I told him I wouldn’t do business with him. I take full responsibility for what happened. I sent him on his way without really hearing his proposal. I had no idea he was some kind of criminal. I never dreamed he would do this.”

“It is not your fault Serena. You could not have predicted what he would do. I love you and I always have.”

Her smile lit up the whole room and it was aimed at me. I reveled in it. She took my hand and raised it to her lips.

“I am also sorry for taking you on as a maid and humiliating you at the lingerie store. I thought I wanted revenge for the way you treated me, but I felt even worse after I did that. You did not deserve to be treated that way and I am truly sorry.”

“I understand. I deserved it. I did not handle learning you were born a male very well.”

“I am dismissing you as my maid Emma. Instead, if you still want to be with me, I want you to live with me as my partner and my spouse.”

“Yes, yes, yes! A thousand times yes. It’s all I ever wanted.”

“Before you agree there is one condition. If you want us to be lovers, you must remain as Emma, not Mark. You need to live with me as the girl I fell in love all those years ago.

I tried to tell her we were one and the same, but she held up her hand to stop me.

“I know what you are going to tell me, but please listen. I was serious when I told you I have no interest in masculine males. I never have. Remember when I had you try on that dress that I made for a friend a few days after the pageant.”

I nodded, remembering how she gave me a hand job and allowed me to touch and suck on her breasts while I was wearing that dress.. 

“You were the friend I made that dress for. I wanted Emma to stay. I was hoping to have you associate being dressed like a girl with sex. I know it was devious and under handed and I am very sorry for doing that to you. It was what I needed then and it is what I need now. I knew how you felt about dressing up as a girl and that just asking you to do it would probably not work. I wanted you to crave wearing skirts, dresses, and lingerie. I know that I failed in that attempt. Unfortunately, I am not turned on by masculine men, only by feminized men.. I have tried both as well as women. The only people that I find sexy are feminized men like you."

"Like me?"

"I hope you can understand.  I love you, but if you want to be my lover you will have to agree to be Emma, fulltime.”

“I don’t understand. Do you want me to change my sex?”

“No, I will make good use of your boy bits… in time. But I do want you to appear as a female and I want you to have breasts.”

I was stunned to put it mildly.

“Breasts? But how?”

“I would have you get implants and take low dose female hormones that will not affect your ability to perform in bed.”

“What if I choose not to be Emma? What then?”

“I will buy you men’s clothing if that is what you want and I will give you money to get started with a new life, but you cannot stay with me as my lover.”

“I need to think about this.”

“I know what I am asking. It is a huge thing to ask. I hope the answer will be yes. If it is not, I would hope that we could still be friends. Please take all the time you need and be sure of your answer.”

She kissed me and told me she would leave me alone.

I sat at the table for a couple of hours draining the coffee pot. I never wanted to wear female clothing and yet I had worn it almost non-stop now for a couple of years. 

I thought about it for several hours. Serena came in to tell me she was going to bed. She kissed me on my cheek as she said good night.

I told her I would sleep on it and let her know the next day.

I slept little. I tossed and turned trying to decide. Being with Serena had been my fondest wish and I could make it come true, but at a price that I didn’t know whether I could or would want to pay.

If I left and resumed being a man I would either never see her again or see her as a friend, frustrated that I could not be her lover. I knew that I could not just be her friend. It would hurt too much. I finally fell asleep not knowing what to do.

I woke up early still undecided. I got out a pen and paper and wrote the pros and cons. I realized that it was not a logical problem but an emotional one. I was hopelessly in love with Serena and I needed to be with her even if it meant I had to be a girl for her. I knew that I hadn’t been much good as a man on my own.

I got out of bed, showered and shaved all over. I spent a lot of time on my makeup and hair. I looked as good as I possibly could make myself look. Then I got dressed in my black French maid’s dress with white petticoats, black tights and 4 inch stilettos.

I went to the kitchen and prepared her breakfast. I went outside to the garden and cut a couple of roses. I even waved to the man next door when I heard him whistle at me as I bent over to cut the flowers, knowing I was showing him my panties. I put the roses in a vase and on a tray with her breakfast. I carried it to her room and knocked on her door.

“Emma, please come in.”

She sounded nervous. I smiled to myself. I opened the door and walked in. She looked at me with her mouth open and just stared. I curtsied.

“Your breakfast is served madam.” I said placing it on the table next to her bed.

She grabbed me, pulled me down on top of her, and planted kisses all over me. Then she rolled me onto my back, pulled down my panties and tights and had me sit on the bed's edge.

She got out of bed displaying her beautiful figure covered in her short black nightie. Her long brunette hair cascading past her shoulders covering her perfect breasts which pressed against the silky material containing them.

I took in her presence. She looked me dead in my eyes ready to devour me. I was as hard as I had ever been, my being raped a few hours earlier was just a distant memory.

"Emma, I'm beyond happy to have you back in my life.”

She then pushed me onto my back and lowered herself onto my erection and what I had been dreaming about for so long became a reality at last. 

**********************************************************

Lance woke up with a terrific head ache. It took a few minutes for his eyes to focus and realize he had no idea where he was. He tried to get up, but his body wouldn’t move. 

He was spread eagled on a bed with his wrists bound to the head board. He attempted to move his legs but they were bound to the foot board of the bed. 

“What the fuck!” he screamed.

He looked around and saw that the room he was in was some kind of large storage room filled with boxes and furniture parts. 

He heard a door open. A statuesque woman appeared next to his bed. She was wearing a black corset that pulled in her waist, black panties and black fishnets. She carried a whip. He couldn’t see the stilettos she was wearing but he heard them as she walked into the room. The last thing he remembered was getting kicked in the groin by that bitch Serena Brogdon. He could still feel the ache in his balls.

“Hey! What is this? Untie me now you whore!” he yelled. “What the fuck have you done to me?”

The olive skinned woman smiled at him. It was not a friendly smile. She flicked her wrist and the whip she was holding landed on his cock which caused his morning erection to subside rather quickly. He screamed.

“I suggest you calm done and show me some respect.”

“Like hell I will. Release me or I will…”

“You will what?” she said waving the whip.

Lance realized he had no leverage and forced himself to remain calm.

“What have you done to me?” he asked calmly.

“Nothing yet.”

Lance could feel his temper rising but he managed to hold it back. He vowed to himself that when he was free she would pay.

“What are you going to do?”

Ignoring his question she held up a picture and asked him “Have you ever seen this girl?” 

It was a picture of Emma.

"No. Never seen her." Lance said struggling against his ropes.

The dark skinned mystery woman cracked her whip once more on her male captive.

“Try again!” she said.

"Ok..ok..maybe I have seen her, but that is no girl. It is a sissy faggot who acts as a maid for one of my business associates.”

"The one you raped?"

Lance couldn’t help but laugh at the memory.

"No, I didn't rape anyone! I-"

Lance then felt whip hit his testicles with force.

"Ahhh!!…you bitch…okay..okay, I did fuck that sissy, it's what sissy faggots want. I did her a favor.”

“How do you decide who is a ‘sissy faggot’?”

“Any guy walking around in a dress wants a piece of meat up his ass, so I gave him what he wanted. Who are you?”

“I represent the ‘TG Correctional Society’. The name is a bit misleading because what we do is correct bigots who prey on the transgendered like you did to Emma.”

“What are you going to do to me?” Lance said suddenly nervous.

The woman then walked over to a table and clicked off a recording device. Lance realized that he had just incriminated himself. 

“What will happen to you? Well for starters, since you are tied up and unable to do anything, I thought I would fuck you” said the woman beginning to pull her panties down.

“That might be too bad” thought Lance, that is, until the woman pulled down her panties showing Lance an 8 inch cock that was only half hard.

“Would you call me a sissy faggot?  I also like wearing dresses.”

Lance was silent realizing he may have said too much. The woman released his legs and Lance tried to kick her. She was ready and with a flick of her wrist struck his nut sack with her whip. He howled from the pain. With surprising strength the woman brought up one leg at a time and fastened it to the head board bending Lance in half and exposing his anus. 

She then spread a generous amount of lube in his asshole and on her hard cock. Without mercy she rammed her cock into him. Lance let out another scream. She got into a steady rhythm and while doing so masturbated the helpless man. When she felt him tensing up she released her own sperm into him. He came with her spewing his seed all over his face, chest, and belly.

“That will be the last time you ejaculate” she declared, laughing.

With his cock now flaccid, she grabbed a cock cage and locked it on him. She held up the keys so he could see them.

With that cage on you will be unable to achieve and erection and these are the only keys. She calmly walked over to a toilet in the corner of the room, dropped them in and flushed the keys down the drain.

The screen then went black. The private video that Brenda Flores, founder of the TG Correctional society had sent to Serena of Lance's capture was proof that justice had been done.

"Brenda Flores is a friend of mine. She got tired of the neglect and discrimination our community was getting from both sides of the law, hence founded the society" Serena told me. "Brenda said he cried like a little girl."

Serena held me tight.

"Lance Johnson is one of his many names, turned out he was a con artist with a history of theft and sexual assault. I will not allow anything to happen to my loved ones," said Serena kissing me on the forehead.

The video was sent to Serena's email on an encrypted link. She wanted to reassure me that Lance would never hurt us again or anyone else.

"My god! What will happen now to him?"I said watching the repeat on her laptop.

Serena smiled, "Not exactly sure, but I think he will get plenty of cock where he is going."

******************************

Lance was groggy as opened his eyes. The last thing Lance remembered was a giant needle going into his ass after Brenda had her way with him. When he was fully awake he noticed he was enclosed in a large crate. There were some holes that allowed for air and light to come through. Through one of the holes, he noticed he was in a large airplane hangar. Lance was uncomfortable as he felt some large cylindrical object up his bum. He tried moving to get it, but the straps around his chest, waist, and legs prevented him from moving much. His hands were also useless as they were enclosed in fingerless mittens and tied tightly to his sides. He tried to yell, but his mouth was gagged shut with electrical tape.

The space was tight. He felt soft cushion padding around his body. The more he struggled the more he sensed his appearance had been altered. He thrashed and struggled as much as he could, but it was to no avail. The restraints were locked in tight.

He turned his head and felt hair moving on his shoulders. He always had a buzz cut. Where did that hair come from? He wondered what was going on. He felt pressure on his chest and looked down to see two mounds protruding. He could feel the cage restraining his cock and balls as well under the pink maid dress he was wearing. 

"Ahhh..mphhh! he groaned in agony. 

Flores & Associates Shipping was the name on the plane door. 

"Hurry up and get the rest of the four crates on the plane, we are running late," one of workers outside yelled. 

Lance tried yelling, but it was futile.

"Mmmphhh!"

"Did you hear something?" said a loading worker. 

"No, plus they told us not to open them and to be honest, I don't really care. All I know is that it sounds like there are animals in there and they need to reach their destination now," said their loading lead. 

"Someone is paying top dollar to get these crates out of the country and to….Kha…wait no…I can't even read it, let alone pronounce it.  Just hurry up everyone!"

The crate containing Lance was then placed along the other three large crates also making similar muffled sounds. 

The large compartment of the plane holding the crates went dark as the large hatch closed down effectively silencing any sounds Lance and his peers made. The only sound they heard now was the sound of the plane's engine coming alive.

Epilogue 

The walk along the gardens of the Jane Powers Finishing School was lovely. Ever since my wife Serena became a very generous financial donor to the school it has been improved upon after years of gradual neglect. 

"I loved this school as a teen girl, Miss. Chen. I regret I could only spend one year here. I met my lovely wife Emma here," said Serena to the newly appointed Principal. 

"How wonderful! It’s just so wonderful knowing our most generous donor also happened to be alumni. And please call me 'Jessica,' Miss Chen sounds too formal."

Serena smiled and nodded.

"The staff and students can't begin to express how thankful we are, the school has had its ups and downs in recent years."

"Yes, I heard that the first ever womanless beauty pageant may have created resentment among some closed minded parents as well as some other donors who pulled out their support," Serena said to her. "Either way, it's all in the past."

"Yes, it was quite unfortunate," Jessica Chen said. "But things have changed and are continually changing in this community."

"I'm sorry you had to keep your relationship with Miss Shultz a secret for so long, I know it was more than fear of losing both your jobs. People can be so closed minded. She was a great principal when we attended."

"Dana and I are in a better place now that, we have each other and are honest about it. The future and educating the future leaders is what is important," Jessica said. "The sister school is almost complete in Centerville, we are beyond excited when it opens later this year all thanks to you and your associates."

"It will bring both our towns together and bring new jobs to the city as well as better educational opportunities for the children there."

"Emma, what do you think?"

CLICK CLICK CLICK

Walking with my high heels was something I was still getting used to, the grassy path not making it easy on me. Being out in public now permanently as Emma was still taking some getting used to. I felt nervous at times, but not as nervous though as when we met my mom at her home. With the help of Serena we were able to purchase the house and give it back to my mom.

I day dreamed about reintroducing Serena to my mom and introducing myself as Emma to her as well.

**********************************************************

Seeing her aimless directionless son Mark, now her daughter Emma was a shock especially with everything I put her through, but seeing how happy I was now and complete after being reunited with my love Serena at my side, she was more than accepting. Our reunion was a happy one.

On that day when Serena would ask my mom for my hand in marriage, I felt so vulnerable and nervous sitting in my yellow sundress trying my best not to fidget too much, which caused my butt plug slightly to press upward inside me. It was Serena who insisted, I guess not only to keep the fire in the bedroom, but as a reminder that she wore the pants (figuratively speaking, of course) in the house even after she completed her full transition making her a whole woman. She didn’t transition to spend her life in trousers.

My mom of course said, "yes" as she now had two daughters. 

"I'm so happy for you two," my mom said to Serena taking a sip of her tea.

"I always liked you for my Mark…err…Emma,"

"That's ok Mrs. Taylor," Serena said to her.

"Oh please honey, we are family now, just call me Monica or mom."

Serena nodded.

"Serena honey, you don't look any different from the last time I saw you years ago at the dance, still taller than Emma even in her heels. I'm glad you and Emma are together, especially with the way  it ended. I'm sorry that happened."

"It's all in the past," Serena smiled. "Emma is now here with me to stay."

"I felt terrible for you honey, he wasn't ready for it, I talked to him, but like his father he was so far up his ass that he couldn't think straight," my mom said.

We all laughed a little at my mom's honesty.

Serena leaned in next to me and whispered, "I rather enjoy being up your ass." 

Serena must not have measured her tone correctly, because my mom's eyes went wide while sipping her tea at the implication. I smiled nervously turning beat red and wished I could disappear right there and then that day. 

**********************************************************

"Emma! Did you hear me?" yelled Serena. "I'm sorry again for being late, Emma is such a girl. She takes forever getting ready. By the way, I hope her skirt isn't too short…I mean I don't want the rest of the donors at the meeting thinking she is some kind of tramp."

"Please, Mrs. Brogdon, your Emma looks lovely in that white dress, I love the floral pattern. It is so pretty. She is perfect, and you have to tell me which salon she gets her adorable short hair done."

I couldn't help, but blush at her comments. 

"I can see why you made her your wife."

Serena couldn’t help but smile knowing everyone believed that I was her trophy wife.

"Oh here we are, as you can see the auditorium exterior looks so much better after the improvements."

"The Brogdon-Taylor Center?" said Serena looking at the lettering naming the new auditorium. 

"Please watch your step. Just past the entrance, there will be a plaque recognizing you and your wife in helping sustain this school, but we wanted to ask if you wanted to include perhaps a personal message below your names?"

Serena looked me in my eyes took my hand into hers and gave me that same smile when we first met all those years ago and said, "How about… What Goes Around Comes Around?"

The End.