Pizza Delivery with a Twist Ch. 02

Hi there, it's Brie and I'm back to continue telling you about my adventures in the strange world of pizza deliveries with my friend Jimmy J and the crew at the Pizza shop.

At the end of the first story Jimmy J was going to speak to his (gay) bosses about me joining the team. His angle was going to be related to the amount of business the pizza shop was experiencing and how a side kick might make the deliveries go quicker. He was also to make it clear that I'm cross dresser and I wanted to do so on the job.

Jimmy J called me and told me to be dressed and at the pizza shop by 4 pm to have a sit down with the bosses. I was excited and began prepping immediately. CD's with a few years of experience can be dressed in no time and that was me. I needed to be extra cute. Dress to impress as they say. Mission accomplished.

I arrived at the shop right on time and parked on the side of the building. I was getting nervous so I took several deep breathes, adjusted my wig and headed in. Jimmy J met me at the door, told me I looked great and pointed towards a small corner table. I took a seat as instructed and waited. I could feel everyone staring at me, the new girl, as I sat and waited.

A man walked out of the back and was coming my way. He introduced himself as Gary, one of the owners, and would be conducting the interview today. We shook hands and he took a seat.

Gary implied that Jimmy J had provided him with a great deal of information so he was not going to make a big deal out of my life choice. He went through the history of the Pizza business and their basic rules and regulations. Then he asked me why I thought our "buddy system" would work.

I told him that I thought the "buddy system" would improve Jimmy J's timing and efficiency based on last night.

"My idea is that the Navigator manages the streets and the funds while the Runner manages the delivery orders. The Navigator could sort out the orders and the money while the Runner was out of the vehicle".

Gary chuckled and agreed we could give it a trial for 2 weeks. He made it clear that splitting the tips was strictly between Jimmy J and myself and that I was to live up to golden rules at all times.

The customer is always right.

Be friendly and represent the pizza shop well.

If I dressed, I could be cute but not slutty.

I laughed at his last rule but agreed to all of them. He stood up walked over to the counter area and grabbed a visor cap that had the pizza shop name on it and handed to me.

"Welcome aboard. You can ride with Jimmy J tonight if you want to and if he agrees."

"So, for 2 weeks I only work for tips?"

"Yes, is that going to be a problem?"

"No problem, I just want sure everything is crystal clear between us."

"Sounds good, now go find Jimmy J so I can get back to work."

The visor cap was going to be a helpful tool. It would provide additional facial coverage and would make my cheap wig look better by adding a break line.

I found Jimmy J outside sitting at one of the picnic tables. I said "We are good to go and we can start tonight if you want to. Gary agreed to a trial for 2 weeks."

"OK, we can ride together tonight. I propose for the trial period we split the tips 60/40 in my favor and the gas money comes off the top."

I extended my arm for a handshake and said "Partner."

Jimmy J shook my hand and said "you have 45 minutes if you want to go home and change."

"I'll be in back in 40."

I made the short drive home and ran inside. For the first time in my life, I have 2 jobs and one of them allows to live life my way. I was very excited and started to change. I spent a few minutes adjusting the visor cap over my wig and forehead. I managed to pull a ponytail out the back and I was impressed. I should have bought one of these a long time ago.

I was going to upgrade my breast forms from 34B to 34C, but I remembered Gary's last rule. Cute, but not slutty. I found a plaid skirt with a length that I thought Gary would approve of and pulled it over my Leggings. I thought I might be safe with the Leggings under the skirt. I was fully covered so there should not be anything to complain about.

I pulled some knee-high socks on for additional coverage and comfort. I would be wearing a mask all night but put on a little lip gloss anyway. I slipped on my favorite high tops, grabbed a Hoodie and headed out.

During the drive back to the shop I kept telling myself "fem voice for the next 7 hours." I repeated it over and over in my head. I have several years of practice with my fem voice but never had to maintain it for 7 hours.

I parked in the same spot on the side of the building and went inside. The pizza world stopped spinning again for a minute as all eyes were back on me. Even the 2 girls who worked in the back that were checking me out. I assumed everyone knew what I represented. I was going to have to deal with it and so were they.

Gary came out of the back and walked my way.

"Ready to go?"

"Yes, ready and able."

"OK, you look great. Jimmy J is loading his car right now."

"Then I better get going."

"No flirting."

"No problem, boss."

I found Jimmy J loading boxes and containers into his back seat. He slammed the door shut and said "let's get this done."

I jumped into the passenger seat and put my seat belt on, taking advantage of the seat belt effect. Jimmy J said that once we were in the busy neighborhoods, we would lose the seat belts to save time.

Pulling into the first neighborhood Jimmy J started to explain his regulars. White house with big porch - good tipper. Red brick house with tall bushes - normal tipper. Split level house - wish he would order from somewhere else and so on. He had them all marked.

"You are going to have identify your own marks as time goes on, but you need to know who is who."

"I'll pay attention."

He pulled over and said "top pizza box and the medium size container. $25.50."

I grabbed the two items and headed to the door. A thirty something guy answered the door and said "perfect timing."

I handed him the box and container and said "$25.50." I could see into his house and knew there were at least two children in there.

He handed me $40 and said "No name tag?"

As I was reaching into my Hoodie pocket for change, I said "My name is Brie. I'm in training so I don't have a name tag yet Sir."

He said "Keep it" and backed into his house.

I marked him as Friendly Flirty Family Guy (FFFG).

Jimmy J had a container on his center console for the money. I put the money in the container and said "Next."

Jimmy J pulled out into the street and drove to the next house. This continued until the back seat was empty. Then it was back to the Pizza shop for another load. We delivered about 7 car loads during the course of the night. It was very busy and basically non-stop.

During the route I managed to mark several houses that Jimmy J said were regulars. It went from FFFG to Bitch Girl (BG), Mad Guy (MG), Under Dressed Lonely Lady (UDLL) and many others in between.

Under Dressed Lonely Lady (UDLL) was very a friendly mature woman with boobs the size of Idaho. I was still chuckling when I got back in car.

"Was she wearing much?"

"A Night Coat that was totally see through."

"Expect the unexpected."

And then there was Paint Guy (PG). I literally spent 2 hours with this guy 4 days ago at the Home Improvement store creating a large paint order for his business building. He was calling me "Bryce" by the time we completed the paint order and now I was standing in front of him as "Brie" and he didn't know it.

At the end of the night Jimmy J drove us back to the shop for the last time. He went into the office to sort out the money and I plopped down in a chair. I was exhausted and didn't care that all of remaining employee eyes were still on me.

Louie, who is Gary's business and life partner, came out of back area and introduced himself. I stood and extended my arm for a hand shake. He shook my hand and stated that our buddy system seemed to have worked out well. We out performed all of the other drivers. I smiled and said "Thank you, boss."

I made it through the entire evening without anyone calling me out and looking down at me like they knew something or giving me the side eye. I was just a female delivery person. It was a pretty good night all and all.

Jimmy J came out and handed me $210 and said "Successful first night on the job." He followed that up with a "Let's go, we're done here."

I thought to myself "No rude comments and a pocket full of cash. It was successful."

"Do you want to stop by for a few minutes?"

"I don't know, you look pretty tired."

"I just want to celebrate for a bit. I made money tonight."

"OK, maybe for ten minutes."

He followed behind me so I could pull into the driveway. As soon as we were in the door I started to strip down to my bra and panties. He stood there and watched me throw my clothes this way and that way.

"Drop your jeans."

He was out of his jeans quickly and approached me. He hadn't trimmed yet, but I wasn't going to worry about that tonight.

I stepped back and asked him if he liked my body.

"Yes, your body is almost perfect."

"Almost?"

"I wish you had bigger hips."

"Me too, but they don't sell hip implants."

"Yesterday you said you weren't looking for a boyfriend. Has anything changed?"

"No, I'm just horny from a successful night on the job and now I want to give you a job."

"Can I sit on the couch? I'm exhausted too."

I led the way and extended my hand indicating where to sit. I dropped my panties and started to undo my bra.

"If you need the bra to keep your boobs, then leave it on."

I left it on and kneeled in front of him, grabbed his rising flag pole and started to slowly stroke it.

"No kissing, but you can touch me anywhere you want, if you want to".

"Sit on lap."

I stood up, turned around and sat my naked butt on his naked lap. I carefully position myself on his tool so he was positioned right in my crack. I took longer than I needed to and I think he enjoyed it.

He reached around and started groping my fake boobs. I slowly moved back and forth in an effort to hot dog myself.

"Can you feel me squeezing your boobs"?

"Not as much as I had hoped for, but I know you are massaging my chest."

"They feel really good in my hands. Are they available in different sizes?"

"Yes, all sizes. I have two sizes. These are 34B's. I have a pair of 34C's. They are also many types of applications. These are inserts that slip into the bra cups. They also make a vest type and adhesive types."

It's nice being felt up while you have a hard cock splitting your buns, but was time to get down to business. I shifted and started working my face down to his lap.

"Do you like either of the girls at the shop?"

"Karen is really pretty and nice, but she has a boyfriend."

"Is she the brunette with the big boobs and those wonderfully wide hips?"

"No, that's Suzie. She is a bit of a goth girl outside of work. Karen is the blonde with normal boobs and hips."

We both chuckled. One day on the job and the office gossip has already begun.

"Do you like any of the guys at the shop? That guy Rick looked pretty hot."

"For the last time, I am not gay. And you should know that everyone in the shop knows what you are all about."

"I figured as much. Are there any major problems I should know about?"

"I spent more time explaining to the crew that I am not gay. No one has really said anything."

"OK straight guy. You want me to suck your dick dry and swallow your hot load now?"

As he was pushing my head down to his lap he said "shut up."

"I'm not going to apologize for not being any good at this. It's only my second time."

I opened my mouth and allowed his boner to enter and started sucking as best as I knew how.

Note to self "watch a few porn movies for educational purposes."

Based on Jimmy J's moans and groans I wasn't that bad. His hips were thrusting as if he were fucking my mouth. I used a free hand to gently massage his balls. They felt large and full as I was soon to find out.

Within a few minutes his body tightened and he erupted into my mouth. Another full load, just like last night. I would have been able to contain his load but he kept thrusting with every squirt which forced some of his juice out of my mouth and down my chin. I swallowed what I could and wiped my face off with my hand. I showed my hand to Jimmy J and started to lick it clean while he watched me. His head dropped back on the couch as he exhaled deeply. He was spent and going limp.

We stayed there on the couch for a few minutes catching our breath. He was rubbing my shoulders and I was rubbing his legs. I went back down on his limp dick for a few minutes.

"You sucked on my spent dick last night too. What's up with that?"

"I'm not sure. When I looked at your spent dick last night, I found it to be appealing. Same with tonight. Are you too sensitive for a second round?"

"Yes".

"OK, I'll stop. Go get dressed."

"Are we going to do this after every shift?"

"Probably not. You shouldn't expect it but you should take what's made available to you."

"Are you ready to admit that you are a gay cross dresser?"

"No, I'm a cross dresser who has additional experience."

"Fair enough. I'm out. I'll see you next weekend."

He was dressed headed for the door.

"What are you going to do during the week?

"Buy some new clothes and try to find a better wig."

Once the door closed, I wrapped my panties around myself and made a mess. Time for bed.

A few days later (Wednesday evening) I was near the Pizza shop after shopping so I stopped in. I was only dressed in a black skirt, wig and a little make-up. I wanted to give everyone a chance to say or ask anything without Jimmy J being around.

"Are you working tonight?"

It was Suzie, the goth girl. She was a prep cook.

"No, I was shopping nearby and thought I would stop by and say hello to everyone. Truth be told I'm willing to open up a Q&A session if one is required."

Sal, the counter manager looked up at me and then around the shop.

"I think we're all good here. Everyone chooses their own life style and we are not judges"

"Thanks, that is what I was hoping to hear. I'll be going so all of you can get back to work."

"See you this weekend" was the popular response.

I approached Suzie and whispered in her ear "I would not refuse your assistance with making me up with a darker look. No pressure, just a thought."

Her eyes went big and I envisioned her jaw had dropped under her mask. She didn't say yes and she didn't say no. She was frozen.

I repeated "No pressure Suzie."

"Hey, while you're here would you mind dropping off one order? We messed an order last night so Gary wants to send one of our regulars a free pizza. You don't need to collect any money. Just drop and go. It will be ready in 2 minutes."

It was Rick, the oven master. The hot one I mention to Jimmy J.

"Sure."

"Let him know that we are sorry for the mistake and it's on the house."

"No problem."

Suzie approached me and held her hand out implying she wanted my phone. I couldn't read the look on her face so just I handed to her my phone. She entered her number and handed it back to me.

"Let me know when. I'm usually free on Thursday's."

I looked her in the eyes and thanked her.

"Be careful what you wish for."

Rick handed me the pizza box and address. I turned and waved good bye to everyone and I was off.

The address was very close. I found it and pulled over in front of the house.

"Hey, I've been here before."

End Pizza delivery with a twist 02