Leaving Greg

My first few months living my life as Gregs sissy were mainly due to not wanting him to expose my life to my family, but the more i lived as his sissy the more i obeyed him out of wanting to please him.

I would spend my days perfecting my make up skills and practicing talking like a timid lady, so when he came home I would be able to impress him. Unfortunately, his gambling addiction was getting out of control and he would allow other guys to have their way with me for a price.

It got to the stage where i was being fucked by strangers on a daily basis. Hoping he would eventually change, i did as he asked. The more money i made for him, the worse it got. When I finally found the courage to refuse his requests, he immediately threatened to send my mum and dad videos of me sucking his cock. Thinking to myself that life couldn't be worse than what i was living now, I told him to do whatever he wanted and that i was leaving.

He made good on his threats, and i was now completely alone. My family did not want to know me anymore and i had nowhere to go.

Luckily I still had money in an account that Greg didn't know about and was able to stay at a motel until I found a cheap apartment to rent.

With nothing to hide anymore I lived my life as a lady and loved it. Shopping, eating out and just walking around the streets as a woman was something I never imagined myself being able to do. Needing money to survive however, I found myself advertising my services on an escort website, and would entertain clients in my apartment whenever I needed the money.

On this particular occasion, I met my client downstairs and after the formalities were over, I took him up to my apartment. In my apartment, Chris, the client, paid me my money and then proceeded to tell me that he had seen me outside on many occasions and couldn't believe that I lived in this apartment building as he also had an apartment in the same building.

Trying to keep it strictly business, I stripped down to my stockings and suspender belt, and moved in towards him letting my hand settle on his crotch. Through his pants I could feel the outline of what appeared to be a rather large cock. Unbuckling his belt, I dropped his pants to the floor, leaving him in only his briefs, which were ready to burst apart.

To relieve the pressure on his briefs, I quickly removed them for him to reveal one of the most beautiful looking cocks i had ever seen. It was at least 8 inches long, cut, and rather thick. It actually looked like a dick you would only see on porn videos and, I must admit, i was rather excited. I couldn't believe I was getting paid to play with this gorgeous thing.

Touching it, tasting it, everything about it was unbelievable. As he slid it into my little hole, the joy it gave me nearly made me want to give him his money back.

His time was up way too soon but trying to be professional, I had to call the night to an end, and showed Chris the door, hoping this wouldn't be the last time i saw him. Weeks passed and I never heard from him or saw him in the building. But then, one day as I went downstairs to pick up a package, i saw him across the road getting ready to leave the cafe he was in. As he crossed the road, I pretended to be looking in my mailbox so when he walked in we could bump into each other.

We talked for ages before heading to the lift together. Chris confessed he had been hoping to bump into me for a long time and as the lift stopped at my floor, I decided to invite him in for a drink, which he accepted immediately.

As we sat drinking a glass of red wine and talking, you could feel the sexual tension in the air. Telling Chris I needed to go to the bathroom, I excused myself and headed into my room. I changed into a red bustier, black stockings, black panties, and put on a white lace robe and my heels and headed back out to Chris.

Needless to say he liked what he saw and stood up as I approached before embracing me in his arms and kissing me. Telling me, in between kisses, how he hadn't stopped thinking of me since our first meeting, I could feel his massive cock grinding against my thigh, and I then admitted how I had also been thinking of him as well.

Taking his big cock into my hands, I found it very hard to keep myself from showing him just how much of a slut I really was. He was soon inside me, passionately making love to me till he ejaculated into his condom. Chris cleaned up and was about to put his clothes back on when I asked him to stay for dinner, which he accepted without too much thought.

We sat down and ate and talked for a while but it wasn't long before we were in the bedroom again.

After making love for the second time, we lay on the bed talking and watching tv. Laying next to him, listening to him talk, all I could think about was his awesome love machine. Even in its flaccid state it still looked amazing.

I left Chris on the bed as I went to the bathroom to freshen up, and as I walked back into the bedroom, the sight of him naked on the bed was too much to resist, and I found myself laying between his legs playing with his appendage. In no time it was standing to attention and I found myself kissing it while looking at myself in the mirror.

Chris looked at me a little surprised so I started to apologise but he assured me he was happy that I appreciated what he had. As i sat there measuring his cock against my face, looking in the mirror, I plucked up the confidence to ask him if he would mind if I took a couple of photos. He stood up in front of the mirror with me in front of him on my knees. Using my phone he took pictures of me lovingly sucking his big hard cock while looking up at him. When he was about to cum, he tried to move away from me but I wouldn't let him go. He warned me again that he was ready to cum, and with my mouth still wrapped around his shaft he unleashed a massive stream of hot cum into my mouth. Looking up at him, smiling, I milked his cock of every drop of his cum, swallowing it all.

With his balls drained completely, he lay back on the bed and told me that was the best head job he had ever received. Chris had work the next morning so we exchanged numbers and he took off with a promise that he would call me the next day. Laying on my bed, I began to look at the pictures on my phone and fell asleep hoping he would call me the next day.

As promised Chris called me on his way home from work and invited me to his place for dinner. He came past my room and we both headed up to his apartment. Over dinner he asked me if i was comfortable enough to tell him about my past and direction for the future.

For the next hour I gave him my life story and confessed everything to him, eventually breaking into tears. I explained to him that i was only advertising on escort sites as I had to make money somehow.

Chris was very understanding and also quite distressed as to what I had been through, and promised me that I would never go through anything like that again. we talked all night and eventually fell asleep on the couch together.

When I awoke, Chris had already left for work. There was a message on my phone from him telling me that he would love it if he could see me again that night and that there was a spare key in the drawer.

I went back to my apartment to clean up and change and headed back to Chris's before he got home. I took my maid outfit with me and changed into that to surprise him. I was in the bathroom when I heard Chris come home so kept very quiet and pretended to be cleaning when he came into the bathroom.

To say he was shocked was an understatement. He stood there staring not able to say a word. I walked up to him and started to kiss him. We were soon kissing like teenagers, our hands exploring each other's bodies. He was rock hard so I squatted down in front of him, released his throbbing cock from his pants and slowly teased the tip of his cock. As I took him into my mouth he couldn't control himself anymore and erupted into my mouth, apologizing for being too quick.

We spent the whole afternoon and night making love in every part of his apartment.

For the next few weeks we spent every night together before making the decision to move in together.