The Maid and the Pizza Guy

My name is Ryan I am 33 years old. I am 6'1 #200 with auburn hair and brown eyes. I am not in the best shape anymore but I wouldn't call myself fat either. I have been cross-dressing since the age of eleven. It started with just panties but has evolved to full dress over the years. I work as an electrician and take on side jobs when I can.

With the recent state of the economy I was forced to look for other ways to increase cash flow, so I placed an add on craigslist for handyman work. I got a couple of responses but not enough to really help. Frustrated I tried again only I posted my ad in the personal section for a handyman who was willing to work nude for a price. Being that I am a cross dresser I also offered an option of doing it wearing lingerie. I had a few replies right away from guys who wanted me to do general handyman work in the nude. It was great cuz they were easy jobs and I got to charge double my usual fee. Then one day I got a response from a guy named Dillan who was interested in having me do some cleaning.

He liked the idea of me cleaning around his place wearing lingerie. I told him that I didn't have much lingerie at the time but if he wanted I would clean the first time for free in exchange for him buying the lingerie for me to wear. He happily agreed and I gave him my sizes. A couple of days later he had gone to Victoria's Secret and purchased a really hot French maid outfit complete with stockings and a feather duster. And I began my new job as his maid.

I cleaned his place with him watching me a jerking off for a couple of weeks before we began having sex, and every time he bought me something new to wear for him.

After a few months of this I had more lingerie than most women. He even gave me a drawer in his dresser and some room in the closet. This carried on for some time, i'd clean he pay me, we'd have sex and then repeat the next week. Then one day I am doing my usual routine wearing the maids out fit when the doorbell rang. I was a little scared and started for the bedroom.

"Get back here and clean." Dillan ordered.

I was really nervous about it but I went back to my dusting. Dillan opened the door and I could see that it was a pizza guy. He was about 20 years old 5'10" with shoulder length blond hair and very good looking. Dillan asked him to step in. while he was getting his money I noticed the delivery guy checking me out, when I heard.

"Now I can give you a five dollar tip, or I can have my maid give you a blow job. "

I was in shock did he just say that? What now? Dillan waved me over to them; I walked up close to the delivery boy and whispered in his ear while rubbing his cock through his jeans.

"Don't worry I don't bite."

he didn't say a word but I could tell from his growing bulge that he was interested. I took him by the hand and led him to the couch. I reached out and undid his jeans letting them drop to the floor exposing his very nice seven inches. I began stroking his cock.

"Sit back and relax."

I said and I dropped to my knees and started sucking him. After a few mins he was really getting into it. I looked at Dillan who was watching us.

"You want to give me a hand with this? "

and with that Dillan was on his knees next to me taking over. I got up and sat on the couch and began kissing our hot delivery guy, and he started rubbing my cock through my lace panties. A few mins later the guy let out a deep moan and shot rope after rope of his hot sticky cum down Dillan's throat.

"Wow, that was great. "he said.

"But I have to get back to work."

Dillan and I helped him clean up and walked him out. As he was leaving Dillan told that if he wanted to come back by after he was done working that he was welcome. I hoped he would but I didn't think it would happen.

Later that night Dillan and I were relaxing on the couch watching a movie. I was wearing my satin garter slip with matching thong and sheer stockings, Dillan in just his boxer briefs, when there was a knock on the door. Dillan got up and opened the door.

"Hi, my name is Nick. "

he said as he walked in the door. I was instantly excited that my delivery guy came back.

"Have a seat, I'll get you a drink."

Dillan said as Nick made his way to the couch. He sat down next to me and I put my hand on his thigh.

"So Nick,"

Dillan said from the kitchen.

"I'm curious, have you ever worn women's clothes before?"

Nick instantly started blushing.

"Actually I have tried on my sister thong a couple of times. "

"Great"

Dillan said.

"Would you like to wear some now?"

he just smiled and nodded yes, so I took his hand a led him to the master bedroom. I showed him were I kept my lingerie and he picked out a pink fly-away baby doll with matching boyshort. I pick out a pair of white thigh highs to go with and show him into the master bath to get ready. We got into the shower and I helped him clean and shave.

After drying off I helped him into the babydoll and thigh highs, and I put his hair into pig tails. He waited in the bedroom as I went into the living room.

"Introducing the new Nikki"

To be continued.