Delivery Girl: Fluidity’s Crossdressing Adventures

By Rebecca Stone

"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.

Continue reading about her experiences in the full eBook.

• Language: English
• Publisher: Rebecca Stone
• Release date: Jan 18, 2022
• ISBN: 9780463142059

Rebecca Stone

I love writing and reading erotica. I enjoy publishing my content online and get people's perspective on my writings. I hope my readers enjoy the content I put through. Happy reading!

Book preview

Delivery Girl: Fluidity’s Crossdressing Adventures

By Rebecca Stone

Published by

Ecstasy Publications

[e-mail]

Copyright 2022 Ecstasy Publications

All rights reserved.

No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, without the prior permission of the publisher.

The author asserts the moral right to be identified as the author of this work.

This is a work of fiction. Names, characters, places and incidents are either the product of the author’s imagination or are used fictitiously. Any resemblances to any actual person, living or dead, events or locales is entire coincidental

Authors Note:

All characters depicted in this work of fiction are at least 18 years old or above. Names, characters, business, events and incidents are the products of the author's imagination. Any resemblance to actual persons, living or dead, or actual events is purely coincidental.

Contents

Chapter 1: Pizza Delivery Route

Chapter 2: Semi-Official Day

Chapter 3: Unexpected Delivery

Chapter 4: Friday Night

Chapter 5: Dom

Chapter 6: Solo Weekend

Chapter 7: Get Together Surprise

Chapter 8: Wednesday After and Before

Chapter 9: Friday Solo Work

Chapter 10: Shower Date

Chapter 11: Shower Date to Remember

Chapter 12: Miss D

Chapter 13: Score Card

Chapter 14: New Wig and Nylons

Chapter 15: Video Party

Chapter 16: A Simple Visit

Chapter 17: Hot Bath

Chapter 18: Date Night

Chapter 19: Skater Girl Outfit

Chapter 20: New Roommate

Chapter 1: Pizza Delivery Route

For most of the week I'm the skinny guy who works at the Home Improvement store. As the weekend approaches, I may introduce myself as Fluidity. Lucky you or lucky me if we meet on the weekend.

Seven months ago, my friend Jimmy J invited me to ride along with him on his pizza delivery route on a Friday night. It was May, the weather was nice and it was something to do. Food delivery services everywhere were really busy so it shouldn't be boring.

Jimmy J knows who and what I am so I asked him if he would mind if I dressed for the evening.

Jimmy J said he had no issues with that because the pizza shop owners were a thirty something gay couple and he was used to it. I quickly reminded him that I am a cross dresser and not gay. He apologized and said he would pick me up at 5 pm on Friday.

I have been cross dressing for quite sometime so I had plenty of clothes and equipment to choose from. I settled on a simple outfit. Leggings with thick socks, high tops, my shoulder length brunette wig, a shirt and a light hoodie. My ankles are the perfect size but my ankle bones are pronounced so I cover them with the thick calf high socks.

I use a small battery razor every few days so my groin stays bare. I have found that once you are shaven clean it's easier to keep it that way with quick trims every couple of days.

I showered and started getting ready about 3 pm. It's funny to look at myself in the mirror wearing a bath robe and facial make up. I pinned the wig in place and looked in the mirror again. My reflection was taking shape and looking better. The semi low cut shirt identified me as a 34B but did not let you know what color my bra was. I slipped on a black thong and the black leggings. Thongs are very uncomfortable but they are a must with Leggings.

Jimmy J pulled up to my Condo right on time and honked his horn once. I grabbed my little bag, a black mask, my gray hoodie and slipped on high-top shoes and headed out the door. I jumped into Jimmy J's car and said Hello.

Jimmy J said Hello and stared at my chest.

I said yes I have boobs tonight, let's go. I put my seat belt on and positioned it right between my bra cups. I think they call this the seat belt effect.

On the way to the Pizza shop Jimmy J explained that I didn't really need to do anything tonight. He would go inside and grab the take-outs, make the deliveries and take care of the money. I had no issues with that and sat back in the seat. I was dressed in public for several hours so I was pleased.

However, within 2 hours it was quite obvious that this Pizza shop was very popular and the take-outs were non-stop. Jimmy J was a very busy person and was making that paper. As darkness settled in, I decided to ask Jimmy J if wanted me to help him.

I said I could make some of the deliveries tonight. You drive and I'll take the order to the door.

Jimmy J said I would have to discuss it with my bosses first. That made sense so I just sat back and enjoyed to ride.

We finished his evening route and he took me home. He handed me some cash but I refuse his offer. He said it's OK, just take it, I made good tips tonight and I enjoyed the company tonight.

I reached over the seats to verified that he had a good time tonight. It was affirmative. I took the cash and stated that I would consider the funds as my first paid to appear gig similar to what some celebrities do. I'm on my way to fame.

I asked Jimmy J if he wanted to come in for a night cap and to relax for a few minutes.

He said it was a long night and he had to do it all over again the next day and that he should go home to get some sleep.

I said look, I am not gay, have never had fem boy sex and I don't want a boyfriend but it looks like you could use some company. Plus, I had fun tonight being out with a trustful good friend while dressed. I also got a few looks, good or bad, from passing cars, so it was a good night for me.

He agreed to come in for a quick night cap and turned off his engine.

Before we entered my Condo, I turned to Jimmy J and started to brush him off with my hands. He was covered with flour and that needed to stay outside. In the back of my mind, I wondered if of my neighbors were looking out their window asking themselves who is that girl at Bryce's house?

He asked me what I was doing.

I said pizza places and pizza guys have flour everywhere, but my Condo doesn't. He laughed and allowed me to rub him up and down. I think there were three or four boner verifications.

Once inside I sat him on the small couch and grabbed him a beer from the frig. If he was looking, I gave him a long look of me bending over to get the beer. This is why beer is always kept on the bottom shelf.

I walked right in front of him and extended the beer bottle. Jimmy J was peeking at my crotch as he grabbed the bottle from me. I knew I was hard and so did he.

I told him to enjoy his beer and that I would be right back.

I went to my bedroom and pulled off my leggings and the very uncomfortable thong. What a relief. I kept my top on and changed into standard blue bikini panties. I slipped on my PJ bottoms and went back to the Living Room.

Jimmy J had almost finished his beer and stated he should get going. I stood up and dropped my PJ bottoms right in front of him. He immediately became nervous and was squirming around on the couch.

I said It's OK to look. I'm your business partner.

He said did you change your underwear?

I said So you did peek at me when I handed you the beer. And call them panties, my kind like the word panties. I have under wear for my day job and panties for the weekends.

Jimmy J confirmed that he looked at me earlier while I was directly in front of him. He said there was nowhere else to look. I asked him he liked what seen.

Yes, but I'm not gay.

I asked him which panties he liked better.

These panties provide more coverage. I could see everything when you were in your thong.

I said Thongs don't work very well for cross dressers, but did you like what you saw?

I'm not gay but you have an amazing body and it had a huge effect on me all night.

I asked him if he was still worked up as I reached down to check for myself.

He moaned If you're not gay why are you feeling me up now, like you on the front porch?

I replied that I normally get frisky when I have a chance to dress and having someone stare at my fake boobs all night amplified my senses.

I said look, all CD's want to turn a guy on at least once. I think I accomplished that tonight. I am a committed weekend CD but have no interest in sex with men. I am a bottom virgin and plan on keeping that status.

I continued with But I know you worked hard tonight and had to go most of the night with a boner at my expense so maybe there is something we can do about that.

He replied I'm not gay either so I don't think there is much we can do.

My response was to walk around to the rear of couch and bend over on my elbows and said come over here and let me know if you like the view.

He nervously came up behind me and asked What should I do Bryce?

Call me Fluidity when I'm dressed. Drop your pants and try rubbing off on my panties.

I've never done anything like this before Fluidity. Out of the corner of my eye I seen his jeans hit the floor.

I said Neither have I, but if you thrust your hips and rub yourself on my panties, I will wiggle back at you and see what happens.

I don't want to put it your butt.

I don't want it my butt either, now start rubbing.

He started to thrust and rub and I did my best to wiggle my butt all over him. We probably looked ridiculous but I think the job was getting done. I like this activity, but knew I would have to get better at it.

Jimmy J had one hand on my hip and one hand holding himself down on my ass and was getting after it when I felt my panties getting pushed aside. I wasn't ready to hit the panic button yet so I let the activity continue. I also felt the front of my panties getting wet.

A few moments later I felt his skin on my skin. He managed to push my panties aside and had his hot man meat right in crack. It felt great so I let it go for a moment or two and then said Watch what you're doing partner.

Jimmy J was still working himself deep into my butt crack when I felt my own release. Good thing I still the panties on or there would been a mess beneath me.

Then he started grunting so I knew what was about to happen. I wanted him to squirt all over the back but I was afraid to ruin the carpet if he missed.

It seemed like I had no choice but to spin around and drop to my knees and open my mouth. So, I did and said Put it in my mouth and finish. Jimmy J did not miss a beat and entered my open mouth while still thrusting his hips. Yeah, right Jimmy J, this is your first time LOL.

His release filled my mouth full. There must have been five or six streams. The temperature was overwhelming. I hardly noticed the salty taste. I figured it had been a minute since Jimmy J had sex due to the amount of cream to shot into me.

Jimmy J felt back against the wall and starting panting. The poor guy was totally spent. It seemed like my job was half over, now I had to do something with my mouthful of man seed.

I did not want to ruin the moment by running to the Kitchen to spit it out so I doubled down and swallowed. It was a hard swallow, but I did it in one throat motion. His taste was different than my own but it was basically the same.

Thanks Fluidity, that was amazing, but I'm not gay so I don't know how to take care of you. I cannot do what you just did.

I stood up and pointed to my very soaked panties. I said It happened when I felt the warm skin of your fat cock between my butt cheeks.

I peeled down the wet panties and took them off to protect against leakage on the carpet. I took the opportunity to show him my fully shaved crotch and said you need to trim down there if you like my mouth.

You mean this might happen again?

I don't know, it might be gay if we did.

I'm not shaving myself bald.

A little trimming will do. Just take it down a bit and be careful with the clippers.

Maybe you should it for me.

Maybe.

He was still staring at my wet and shaved crotch when I broke the ice with a my boobs are here joke. We both chuckled. I said for two guys who are not gay, that was a fair amount of sex.

What happens behind closed doors, stays behind closed doors. I nodded in agreement.

I knew he was spent but I dropped back down and sucked on him for another minute. I may have graduated from a weekend cross dresser to a cross dressing cock slut.

Jimmy J said he had to go and that he would discuss our delivery partnership proposal with his bosses the next day.

I told him to make sure his bosses knew exactly what I was bringing to the proposed partnership so there were no misunderstandings. I was planning on dressing for the job every Friday night.

Eat more oranges or strawberries.

He looked at me with a puzzled face.

It improves the taste and I closed the front door.

Chapter 2: Semi-Official Day

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.