A New Life Ch. 01

My life change the day that I won the lottery. I had lived my life as a loner, with little to no contact with my family. Both my parents passed away when I was long and I was estranged from my only sister. When I won the lottery and it was announced publicity, family found me. I disappeared again taking some time off from a normal life to pursuit some of my darker fantasies.

I first took almost a year to just work out. I wasn't out of shape but I want to lose enough weight to have a more feminine body type. I started growing my hair out and had all my body hair permanently removed, leaving me smooth. I started to do give myself daily enemas and even on occasion tried female hormones. During this year, I answered several personal ads from men who's wives were out of town. I would spend weekends swallowing load after load of cum. Offering my ass up as a toy to groups of men. I was slowly becoming a whore but I wanted something more.

My closet started be overran with womens clothing. Where my shirts once hung, dresses and blouses dominated the racks. My boxers were replaced with slews of panties and bras. My bathroom slowly became littered with make-up and hair care products. My closet was filled with high heels and ladies boots. I had a stripper pole put in my studio apartment and practiced all the time. An old cabinet I had once stored random things in, was now filled with sex toys of all kinds. Giant tubs of lube, dildos of all sizes and shapes, vibrators of every fashion and more butt plugs then I could count. My life was becoming dominated with being more feminine and sex.

My goal was to finally find a couple in their early 20's to late 40's to serve full time. I wanted to live as a female and live-in maid. I found several couples on BDSM sites looking for such service. One couple I moved in with for two weeks to "test the waters". While I had a pleasurable time, they were into much more violence then I was looking for. Needle play and some extreme water torture. While I enjoy pain, I don't want the whole relationship to be based on it. They understood my feelings and wished me well, but right after leaving there home I decided I wanted piercings.

I pierced both my nipples, my penis and tongue. I had two sets of holes put into my ears also which I took to wearing my lady like earrings. Bigger hoops and such. By the time I felt I had the body I wanted and I had been on female hormones for roughly 7 months. My hips seemed a tad bigger and my penis a tad smaller. My chest was a little saggy, all which made me happy. I started toying with the idea of surgeries but decided I didn't want to do anything that extreme just yet, first I needed a couple to live with. All the while that I was looking for my ideal couple, I was still whoring myself out to anyone. If my ass was empty for a single night, it wasn't for a lack of trying.

I answered an ad for a couple in their mid 30's looking for a live in maid. They wanted a CD who would prefer to live as a female. The more I read into the ad, the more I wanted to live there. I immediately called them to set up a time I could meet them. A female answered and introduced herself as Sara. She was shocked by the quick response but also happy to hear my eagerness. I told her I could fly in and be there the next day. She said her husband Tom would be home in a couple days from a business trip and that the upcoming weekend would be prefect for a visit. She asked me to send her pictures of myself, dressed and nude. She giggled a she instructed me to show her I know how to use my pussy, I blushed so red that I wished she could of seen it. I was so excited to take them that the moment I hung up, I set my camera and tripod up.

I pulled out several outfits I thought would show off my feminine side best. The first was a white silk gown with a line of lace that wrapped around it from top to bottom. I slipped into white silk fullback panties with a small amount of lace of each side. Tucking my little, and getting smaller, penis between my legs, I slipped on my white heals with straps that wrap up my ankles. I sat down at my vanity and started my make up. I used bright red lip stick to contrast my outfit. Next I brushed my hair out and did my nails. After looking myself over in the three mirrored wall I had, couldn't help but want to call someone for a booty call. My ass throbbing to be abused.

I started the camera on a 15 second auto snap. I posed as sexy as I could on the edge my bed. Sliding my gown up to show off my panties and attempting to act as feminine as possible. After I took at least 50 pictures, I changed into a maid outfit I had of my own. It was very very sexy, almost nothing to it. After I was dressed up, I took out a small bottle of lube that has some special ingredient that makes my ass burn. Next I found a feather duster I had bought that had an 8in long and 2in wide dildo for a handle. I took many photos of myself dusty stuff while slightly bent over and my ruffle panties peaking out. I swallowed almost the whole "handle" and dusted things off for a long set of photos, then I took it deep into my ass. The lube made me burn but it made me want more. I dusted several things with my feather duster sticking out my ass before stripping naked for another set of pictures.

I put in a set of pink hoops in my nipples and a pink ring in my cock. My ass was on fire as I took out a huge plug. It similar to The Spade but a tad smaller. It is as big as I can take without passing out. I started the video camera as I started to lube my ass and plug up. I used a a large amount of lube on both before gently sitting down the plug. I position the camera to film the dildo and my ass from an angle as I gently pushed it deeper and deeper in. I felt my ass stretch out farther and farther as I let out some very feminine cries. When I had it half way in, I picked up a dildo sitting next to me and shoved it down my throat. My pathetic cock starting squirting before it even popped into place. I came almost instantly a second time when I finally felt it pop into place.

I sat for a moment catching my breath before I sat up to show the camera my newly plugged ass. I picked up the camera to film my sweat covered body and show the cum spattered on the sheet. I instantly set the camera down to film me licking up very drop of cum and sticking my cum covered tongue out to show the camera. I swallowed greedily before I replaced the camera to film me removing the huge plug. This is almost harder then getting it in but I wanted to show Sara I could do it. In all the film was 54 minutes longs. It showed me cleaning up 5 loads of cum I shot out as I used the dildo.

I think cleaned up before preparing the pictures and video for email. After emailing them I went and took a shower for almost an hour. When I returned, there was a response from Sara telling me that she came herself no less then three times looking through the pictures and watching the video. She wanted me there that weekend and if she had her way, I would be moving in tomorrow.

The only thing I could think was "What am I going to pack?"