Where We Left Off Ch. 05

Randy got in very late from work the next morning. John took me over his lap again and rubbed more ointment on my bottom. He massaged my whole ass. He then ran his finger gently down and up my crack. He would pause and rub over my entry every once and awhile. John stopped again and applied a lot of pressure on my entry with the inside of his thumb. He vibrated his hand while he did that. I got super hard.

"That's a good girl," John said.

John dabbed a little ointment on his finger and penetrated me. He gently worked his finger inside me and found my button. He massaged it with his finger til I came.

"Let's not tell Randy about this, I just felt bad about how he left you yesterday." John said.

John washed his hands and changed his pants. He took me out for breakfast, and we stopped for coffee on the way home. It was a nice cafe in a shopping center. John and I both ordered white chocolate mocha's. The barista was a handsome guy about my age. He was fit, chiseled, blonde hair, and blue eyes that I could stare into all day. I had never had a crush on a boy, I just liked cocks. This was a different feeling. I liked this guy. He was going to school to be an engineer. He seemed very happy in life. The three of us chatted while we waited. He really seemed interested in what I had to say. I blushed as we talked. I couldn't believe this hot guy cared about what I thought.

John and I sat down and talked about my future plans.

"So what do you want to do for work?" John asked.

"I don't know, I didn't mind working in a grocery store, but I hated dealing with customers," I replied.

"Are you good with computers?" John asked.

"Yes," I replied, "I've been building my own computers since I was thirteen. It's one of the few things my dad taught me how to do."

"Well it's settled," John said with a smile, "you'll come work for me. It's mostly data entry, document control, answering the phone, and helping me when I need help. I will pay you twelve dollars per hour, provide you health insurance, and provide you room and board. We only have customers at the office once or twice a month, it will mostly just be you and I."

I readily accepted. This was the best job offer that I had ever received. John brought me to a department store to buy me a few business appropriate outfits to wear if we had customers. He dressed casually in the office and kept outfits in a closet if needed.

We got home in the afternoon. Randy was awake and dressed nicely. Randy seemed happy for me when we told him the news. Randy took me to the side.

"I've been hanging out with this waiter at work," Randy started, "we've been together a few times and we decided that we are going to try dating. You and I can't have sex anymore. I'm sorry, we'll talk about it more later if you want. I have to go pick up Brantley for our date."

And that's how Randy and I ended. To be honest, I had been more of a participant in his sex life than in a relationship with him. Randy and I got along a lot better after this. I didn't dwell on it too much. I was focused on my new job.

The job was relatively easy. John had setup a very effective organization system. The work flow was very efficient. I was able to pick it up quickly, and John was able to focus on his job more. John gave me a three dollar raise after 90 days.

John and I spent a lot of time together. He became my confidant. I told him everything about my life. I told him everything about my relationship with Randy. I told him about Ranger Dick. I told John why I had resentment for Randy. John was sympathetic and believed Randy was in the wrong, but he asked me to forgive Randy in my heart. I tried to, for John. John told me about his relationships. John confided a lot in me as well.

John had noticed that I became more and more agitated over time. Masturbation really didn't do much for me. I had not had a good release since John fingered me a couple months ago. I was pretty ashamed to admit it to John, but he was understanding and charismatic.

"It's better for you when you are stimulated from behind?" John asked.

I squirmed in my desk chair and said, "Yes sir."

"I've been planning on helping you out there now that Randy is out of the picture. I think you cum better when a man help. John said.

John pulled off at a sex shop on the way home that afternoon. He picked out some toys to help me get the release I needed. He choose a couple different size plugs, a dildo with a suction cup, and a prostate massager. He even paid for them. At home he pulled me over his lap, pulled my pants to my knees, and worked some lube on my opening.

"Just relax," John said, "I'm going to help you."

John started worked the smaller plug into me. He played with it. He pulled it in and out. He then swapped it with the large dildo. John penetrated me with the rubber cock. He worked it into me slowly. He then pumped it in and out of me methodically. My cock strained on his pants leg.

"That's it, my sweet girl," John said as he felt my cock grow.

I could feel John's massive cock through his trousers. John hit my button and I moaned loud. John used my moans to figure out what I liked. He would build me up, relax me, and build me up again. He teased me several times. He then went for it and obliterated my button until I my whole body came in a massive orgasm. I blew my load all over John's khakis. John stood me up and wiped the lubed from my cheeks.

"We can do this whenever you need a release,"

John said, "a young girl like you probably needs release at least daily. Maybe more. I will keep these toys in my hidden locker so nobody finds them."

John always referred to me as a girl from then on. He had me wear sweatpants with no briefs in the office. He kept toys in his desk at work. He would have me place my balls on his desk and then bend over on the desk so my balls were hidden. At first he only toyed with me. He began to masturbate during our sessions after a week or so. His cock was huge. He had a huge mushroom head. It was almost half an inch wider in diameter than his shaft, and his shaft was a good two and a half inches. It stuck straight out for ten inches. I stared at it with lust as he stroked it and toyed me. He would catch his cum in a Kleenex at first. After a few days he started letting me stroke his cock as he toyed with my asshole. I looked forward to these sessions. His cock felt so powerful in my hand. John always stopped me if I tried to put it on my mouth. He did let me kiss the head once. He enjoyed shooting his load over my back. He would sometimes take pictures with his SLR camera. I wanted his kind soul and his huge cock so bad.

Randy and Brantley were an item. I didn't care for Brantley very much. He was cocky and spoke with a stereotypical effeminate lisp. Still, I liked him because he made Randy happy. I was a secretary that got finger banged a lot. I guess I couldn't make too much fun of Brantley.

I was closing out the weeks paperwork on a Friday afternoon in October. It was much cooler now, the leaves were turning orange. John walked up behind me.

"Any plans for dinner?" John asked as he cupped my butt cheek in his hand.

I laughed, we ate dinner together every night.

"No plans, John." I replied.

"Can I take you out for dinner tonight?" John asked, "A date."

"Sure," I said, but not entirely sure of what he meant.

We went to a nice restaurant downtown. John had reserved a table. The menu was in French, John helped me choose what to order.

"I think we have been getting pretty close since you moved here," John said.

"We have," I replied, "I have enjoyed spending time with you." I blushed a little, not sure what this was about.

"To be honest with you," John said, "I like you. I like you that way. I enjoy how we play together and I want to do more, but I have a problem. I'm not attracted to boys."

This was the first time that John had acknowledged that I was male in a couple months.

"Ohhh," I said looking down. "I knew there had to be a catch," I thought.

"Do you like me, that way?" He asked, "Tell me the truth."

"I do." I said, barely audible.

"What if, we tried a relationship where you were a girl?" John asked, "You were treated as a girl, you wore makeup, you dressed as a girl, you peed sitting down, and I made love to you like you were a girl. How would that be?"

"You would accept me like that?" I asked.

John nodded.

This was something to think about. I had for all intents and purposes been a girl with Randy. I was androgynous, I only bottomed, and I got mistaken for being a girl frequently. John had already treated me as a girl for months. It wouldn't be very different for me, but it would make a difference for John.

"I could try," I said, looking at the table.

John paused and then said, "Before you agree. You must understand that I will not touch boy parts. I am a dominant. You must be completely submissive to me, one hundred percent of the time. There will be simple rules to follow. We will go over them. I discipline my submissive partner with spankings that can be painful, but only when needed. I'm never cruel with discipline. I also enjoy giving light playful spankings to my submissive partner when having sex. I will sometimes film you being spanked. I will sometimes film us making love. You will sleep in bed with me at night. You will always be ready when I need you. I will treat you fair, and I will take good care of you."

I nodded.

He added, "Our arrangement at work will remain the same. I will be your boss and your dominant at the same time. You will get paid and still receive raises based on merit and inflation. You will not need or have access to your finances. I will put your paycheck in a separate joint account. I will make small and safe investments with this money so you can have a retirement. You will be able to monitor your money. You will have immediate access to this money if our relationship ends."

I said, "I understand," as I was nodding slowly.

"Do you agree?" He asked

"Yes," I said, "I agree."

"Okay," he said, "you are a girl now and you are my submissive."

We stopped off at an Asian Nail Salon on the way home. John had already arranged an appointment for me in the waxing studio.

"All body hair," John told the salon lady, "below the eyebrows."

She nodded.

John smiled at me and slapped my ass.

The Asian lady that waxed me was probably in her sixties. She didn't look like she put up with any funny business.

"On table, now." She said.

She pulled off all my clothes. John sat in a chair in the corner and watched. She waxed me from head to toe, front and back. She waxed my face and my privates. It was pretty painful, but not as bad as I expected.

"Looks good," John said. He then handed me clothes to wear. He had already thrown away my old clothes. It was a black thong with a sort of padded front, cut-off jean shorts, a strapless padded bra, and a black tube top that barely covered my bra. He also had a pair of black high heels for me that he told me not to put on yet. The asian lady looked at me and smiled.

"You look better as girl, suit you better," she said.

John and I both got pedicures and manicures. John had them paint my nails Ferrari Red. I looked like a hooker. I could see John's hard cock through his pants as we got in his car. John pulled out his cock in the car, grabbed my hand, and had me stroke him slowly as he drove home.

John had more clothes waiting for me at the house. Lots of thong panties, padded brassieres, blouses, skirts, dresses, cut-off jean shorts, cut off t-shirts, lingerie, stockings, garters, high heels, dress shoes, sandals, and boots.

"I figured out your sizes from your laundry," he said.

I couldn't believe it, it must have cost John a fortune. We went to the bathroom where he had makeup, a makeup tutorial, and an enema bag for me. He showed me how to flush myself out with the enema.

"You need to flush yourself when you wake up, after you poop, lunch, and before bed. I do not want to get a urinary tract infection." John said.

I nodded in agreement. We then tried out some makeup. I managed to put on a basic foundation and lipstick. John watched me get dressed. My thong poked out the top of my shorts and my cheeks hung out the bottom of the shorts. John and I looked at myself in the mirror. John looked very pleased.

"What's your name?" He asked.

"Tiffany," I answered with confidence.