Femboy Hooters

Story Info
A restaurant with an all-trans wait staff in sexy outfits.
12.8k words
4.82
23.1k
57
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Femboy Hooters

by: Shawna Summers

This story is a work of fiction and a fantasy. Safe sex practices should always be followed.

A very special thanks to a wonderful group of girls that I've been chatting with for about 15 years or so. Some of those girls have been nice enough to lend their names to this story, so thanks to Tara, Candy, Rallie, Jessica, Melissa, Kris, Elizabeth, Tamra, Kristine and others who have kindly lent their names and some of their favorite looks to this story. I've had the pleasure to chat with and get to know these wonderful people over the years and they've always been there to support me. They've even gotten me through some tough times, even if they didn't always know it. The sisters I've gotten from meeting these girls means more than some of them probably know. Thanks girls, I love all of you.

(T/t, M/t -- chastity, oral, anal)

Its amazing how one person can be different people in different situations. I've always been a bit of a social butterfly, never really fitting in with one group or another, even back in school. I was something of an athlete since I was on the swim team, plus ran cross country and track, but I never fit with the jocks. I was a big-time gamer and comics nut, but I never really fit with the nerds. So on and so forth. This was true all through college and as I moved into work.

I did discover a side of myself that I learned early on to keep hidden. I discovered I loved wearing feminine clothes. Starting off sneaking panties and lingerie from my mom's hamper, then onto trying full outfits and experimenting with make-up. Thankfully she has a whole storage closet full out clothes that she rarely wore, so I got to play around a lot in there.

Discovering the online world really opened my eyes up and made me realize I wasn't the only guy in the world who enjoyed being their feminine self. Through it all, I was too embarrassed to try going out or doing anything in public, even on Halloween. Though I certainly wanted to.

When I finished school and got my own place, I was looking for jobs in my degree field, but in the meantime, I needed something to pay the bills. I'd worked at various summer jobs through school in food service, working as a busboy, dishwasher, cook, waiter and when I turned twenty-one, I even spent some time working as a bartender.

So, when a new restaurant opened in the area and had a lot of buzz about it, I checked it out. It described itself as a 'fast casual eatery for the discerning customer with a specialty in pub foods and spirits showcasing an electric atmosphere highlighting an adventurous and next-level style of service with costumes and specialty theme nights.' I wasn't sure what the hell that all meant, but the pictures on the website had lots of girls in cool and sexy costumes. Everything from French maids and cheerleaders to cosplays all the way to latex catsuits and even more wild stuff.

The idea of working as a waiter or bartender at a place that encouraged everyone to come in costumes seemed like a dream come true. Who knows, maybe I could even pick-up some pointers from some of the girls.

I submitted my resume to the 3-D Cafe and received a response for an interview back pretty much right away. They wanted me to come in on Wednesday afternoon. So, Wednesday found me in a nice suit with a fresh copy of my resume. I know a suit wasn't really necessary for a food service job, but I figured why not, right?

I entered and told the really cute girl working the front desk that I was there to meet with Donald Copperfield for a job. She did give me an odd look as I asked, but then shrugged and asked me to sit in the waiting area.

The girl was really tall, and as she walked to the back, I saw why. She was wearing what had to be 5" heels. Holy hell! That was some serious footwear. Her overall look was that of a slutty librarian, with a white blouse, black pencil skirt and those wicked pumps. The sheer stockings with a back-seam only enhanced her gorgeous legs and had me wondering how she worked a whole shift in those heels.

As I looked around, I realized all the girls on staff were wearing some kind of sexy outfit or wild costume. There was a French maid, a Hooters uniform, a cheerleader, while others were doing a secretary, MILF or fashion model type look. I also noticed most of the girls were very tall and a lot of them were wearing heels of some kind, some had more practical heels like wedges or chunky heels, but many were rocking sky high stilettos.

The tall hostess came back and called me to follow her. We went down a short hallway and came to a series of offices. One was partly open with 'Manager' on a placard. The hostess knocked and a voice from within called out, "Yeah, send her in."

I was confused for a moment. Her? I looked behind me and the hostess shook her head, gave me a slight smile and waved me in. I entered a small, but tastefully appointed office with a nicely dressed man behind the desk. I could see 'Donald Copperfield' on a little name card on the desk.

He looked up and did a quick double-take as he saw me, then looked back at a copy of my resume on his desk. He shrugged and said, "Thanks, Talia," to the hostess. He the turned to me, extending his hand, "You must be Gene, I'm Donald. Nice to meet you, thanks for coming in."

"Thanks, were you expecting someone else?" I asked.

"No," he shook his head. "Just a lot of the prospects come in costume or something fancy to show-off. We've had a few come in drab clothes, but they'd usually change here... you don't have a bag though."

"I... uh... no," I stammered confused. Then it hit me, the staff wore the costumes not the customers. Why they hell didn't I pick up on that sooner? "I get it. I was a little confused, I thought the customers wore the costumes. I didn't realize the staff did."

"Yup, you got it," Donald said. "Have a seat. So, based on your experience, I think you'd be able to jump right in. Do you have a specialty you wear?"

"I... specialty? Like a costume? Not really, I've done Obi-wan a few times and Indiana Jones, is pretty easy, too. I guess I'd go with one of those," I said shrugging.

"I think... maybe... you've misunderstood," Donald said simply. "The... uh.... staff are all... trans."

"I... what?" Holy shit! Was he serious? "Wait, the hostess...?"

"Yup, Talia was born Theodore, but much prefers being Talia, she likes the librarian look, if you couldn't tell," Donald explained.

"Oh, wow, how the hell did I miss that? I guess I was in such a hurry to apply, I didn't really pay attention..." I trailed off, realizing he had said something about the prospects coming in drab clothes. Attention to detail, right?

"Its okay, I'm sorry, it happened a few times before we opened, but I thought everyone knew by now. I guess I'll have to explain it better in the recruiting e-mails, but I have to be honest, you'd make a great server," he said matter-of-factually.

"I... would?" I stammered. Needless to say, my crossdressing heart was thrilled, but the male side was still fighting for control. The male side was loosing, badly, by the way.

"Oh yeah, I mean, you're about what, 5' 5" maybe 5' 6"? You could rock 4" or 5" heels and still be under 6' tall. Some of girls love their heels, but when starting at 6' and add a few inches and they look like Amazons. Gorgeous Amazons to be sure," he said. "And with your looks, well please don't take this the wrong way, but you'd make a really lovely girl."

I blushed slightly, the girl side just took full control! "Well, thank you, I appreciate that."

He smiled, "You're quite welcome, and I'm glad you're okay with that, some guys get a little upset, if they hear something like that. In the early days before we opened and the place was known, we got a lot guys storming out with the idea that they'd dress up."

"Yeah, I get that," I nodded. "But you see, I've... uh... well, I've got some experience."

"I know," he gestured vaguely to my resume, "You've got a nice mix of experience."

I shook my head, "No, I mean, I've got experience... uhh..." I waved vaguely to the front of the house.

Realization dawned and Donald's eyes widened, "Oh! So you are trans? Or at least a dresser?"

I nodded, not really trusting my voice. This was the thrill of a lifetime, but I wasn't sure I was ready for it. I was on the verge of doing a happy dance and crying at the same time. It was a weird mix.

"Well, great, then you can start right away," he moved his computer mouse and was starting to type.

"Well..." I started.

"Well?" he asked, looking at me sideways. Then after a pause, "Oh, you're still in the closet?"

I nodded, "Yeah, I've never actually told anyone about this before." My heart was beating like a jackhammer.

"Oh, gotcha. Wow, well then, first of all, thank you for sharing this with me, I know this can be a deeply personal, and sometimes guilty secret, but please know, I'm not going to judge you, and neither is anyone here. This is a great group of girls, honestly. They'd be ecstatic to help you out of the closet," he said gently.

I nodded, feeling a lot better hearing that. The idea of starting out in a judgment free environment was pretty tempting. There was still a nagging doubt. Was I ready for this public a debut?

"Also, remember, you'll be in make-up, a wig and a costume, no one outside of me and the girls would know who you really are," he said comfortingly.

I nodded, "Thank you, that's very sweet."

He sat back and smiled, "I work with a whole cast of trans girls, crossdressers and even a couple FTMs, believe me I have to be understanding and conscious of things. Some of the girls can be diii-vas."

I laughed, "Yeah, I'm not surprised."

"But they are a great group of girls, and I think they'd love to have you in the fold," he said.

Well, hell. He didn't have to sell me any more! I nodded and smiled, "Okay, I'll do it."

He smiled, "Welcome to the club! Let's get you in the payroll system and then I'll give you a tour."

We went through the usual basics of getting someone set-up. Name, social, address, all that stuff. It only took a few minutes and Donald was walking me out to the floor showing me the basics. There were several different areas. The restaurant area with booths and some tables was the main focus. The bar area that also had a dance floor and some risers for a DJ or small band. There was the club area in the back where they could have parties, dancing and some of the theme events. Next, there was a small stage where they would have events like costume contests, karoke, drag shows, even band performances. There was also the back area where they had the offices and the private rooms for smaller events and parties. Since the place had only been open a few months they were still building up a clientele and trying out different theme night and events to see what really hit with everyone. They were also talking about doing a party bus and other ideas for private parties.

Donald didn't really introduce me to any of the girls yet. He said he'd have me come back tomorrow at lunch and have some of the girls walk me through the basics. Then he asked the burning question.

"Do you know what you're going to wear?" he asked.

I nodded, "Oh yeah, I'm going with the French maid! I can't wait. I'm nervous, but really excited, too."

"That's great, I can't wait to see how you look. I'm sure you'll be adorable," he said as we walked me to the door.

I pulled out my phone and went into my hidden folder and found some of my dressed up pics. There were a few of me in my French maid costume. Sure, I'd posted a few of the pics on social media and trans and kink friendly sites, but I'd never really shown these pictures to anyone IRL before.

I showed Donald and he looked taken aback, "Holy hell!"

"What?" I asked nervously, worried I'd shown one of my 'racier' pics.

"No," he said quickly. "Nothing bad, its just, well, you're gorgeous. That's not through an editor or filter or anything?"

I shook my head, "No, just plain ol' me. Well, and a crapload of make-up and falsies."

He laughed, "Well, if you look that good, you're going to slay them here. One last important question. What's your femme name?"

I hesitated there. Well, there was a girl on the swim team named Shawna that always had a confidence I envied. She wasn't the prettiest, the sexiest or anything. All in all, she was fairly average, not ugly, just cute, maybe a little plain, but she carried herself with a self-confidence that my shy, nerdy self always envied. If my femme self wanted to emulate anyone, it was her.

"I'll go with Shawna, its what I've usually used online," I said.

"Just Shawna? No last name? Some of the girls like to go alliterative, some go the drag route and make it a joke or a phrase," he explained.

"How about Shawna... Summers?" I'd used that a few times online, I reasoned.

Donald looked sideways at me, "You know that sounds like a porn star, right?"

"Really," I blushed a little. The idea that the name sounded slutty kind of thrilled me. What did that say about me? Hopefully that Shawna was a lot more adventurous than Gene.

"We'll see you tomorrow and you can meet Sandy and the other girls," he said, as I headed out.

I headed out still in a bit of a daze. Was I really going to do this? I was scared, but I was also rock hard I was so excited. I immediately went home and figured I should practice my make-up and wearing my heels. Oh! And my femme voice. I was going to have a lot to practice.

I reasoned the best way to get in the mood was to get femmed up. So, I dug through my clothes and found a nice set of stockings and matching lingerie. I pulled out my pumps with the three inch heels and grabbed my black mini skirt and black stretchy top.

I showered and made sure to catch up on my shaving. I generally keep pretty smooth, but I figured I should be completely updated for my big debut. In the shower and let the warm water relax me. I was already nervous about tomorrow. Nervous, but excited. Maybe a little too excited, I knew I was going to need to take the edge off, but I wanted to practice my look first.

After drying off, I slipped on my panties and tucked down. I debated practicing taping down, but I was a little too worked up for that. I could barely get myself tucked back as it was. I decided to practice my make-up since that would hopefully settle me down a little. If nothing else, having to focus should take my mind off my excitement.

I debated if it was better to go with a liquid foundation or just use some powder for a base. I figured I'd try the foundation first and see if I got too sweaty or anything. I used my make-up wedge to apply the liquid foundation and blended it in until I had everything nice and even.

I looked over my options for eye shadow and decided to go a little wild and try a purple color I'd gotten a while back, but had never tried before. I rubbed the small brush in the violet make-up, getting a nice coat on the brush and tapping off the excess. I did the usual starting inside my eyelid by the bridge of my nose and used smooth even strokes to get a nice coverage on the inside of my eyelid filling in most of the area below my brow. The color was a little dark on my fair skin, but it wasn't a bad effect. If I did it again, I might try to blend it with a lighter color to brighten it up a little.

I got out my mascara and pulled the long brush out of the jet black container. Again, I got the brush nice and evenly coated. I found that rolling the brush got a nice thick coat of mascara on my lashes. My lashes were pretty thin, so I wound up painting my lashes with the tip of the brush more than anything. I got some pink powder on another brush and lightly brushed that on my cheeks for the rosy cheeks.

I then went to the lipstick. I decided to go with the 'look at me' fire engine red for this time. I figured I'd go a little more demure for tomorrow. Although, thinking back most of the girls were definitely 'put together' and going for a pretty glam look with their make-up, then again there were a lot of girls and plenty of different looks.

I filled in my lips with the bright red and it was definitely an attention drawing color. A very attention drawing color.

I looked at my make-up and decided it looked pretty good. If I could get something looking this good for tomorrow, I'd probably get a lot of attention. Well, to be honest, if I was wearing my sexy French maid dress, I was probably going to get lots of attention any way.

I pulled on my bra and put in the small inserts I had. They would only give me an A cup, maybe a B. If I made some decent money, I'd have to invest in some decent falsies. I had a larger pair that were about a B maybe a C, but I loved the idea of having really big tits.

I rolled up the stockings into little donuts and slid them up my smooth legs. The sheer material feeling so wonderful gliding across my hairless legs. The sensation was enough to make my head swim a little. Stockings were definitely one of my favorite parts of dressing up.

I pulled on my mini-skirt and slid into my black stretchy top. Slipping my feet into my three inch pumps and I checked out the look. I was amazed at how sexy I looked. The black was definitely a basic color and worked in lots of combinations. I wondered how it would be to mix colors and styles. Well, I'd hopefully have lots of chances to do that.

Of course, now I was getting even more excited. Before I did anything I decided to get some pictures. So, I took some selfies, but I wanted some actually pro looking pics. So, I set up my ring light and put the phone on a stand. Framing myself up within the timer was always the problem, but I got a few decent pics.

I debated trying on a different outfit, but I was already making a very un-ladylike bulge in my panties. So, I decided to play some. I got out my favorite dildo and first I practiced my oral skills on the nine inch toy. It was big, but not too big. A nice size, but not too thick.

I got really excited blowing my faux lover, so I got out my lube and began fingering myself while I kept fellating the toy. It only took me a few minutes before I was stretched out and I began sliding the toy into my ass. I slid it in slowly at first, but I was really horny and it was matter of moments before I was plowing my ass, moaning and groaning with need as I tried to hold off playing with myself. After a few minutes, I was so worked up, I was overcome and had to stroke myself. I came in about five strokes, the orgasm exploding out, my cum shooting all over my stomach and even up to my chest.

I lay there panting for a few moments, milking my cum out of my clit as the dildo slid out of me. I began scooping up the cum, licking it off my fingers until I was just smearing it around.

I eventually cleaned up, removing my make-up and getting as much of the cum off as I could. I decided to get in the right mind set and laid down to sleep in my lingerie. I thought it would take me longer to sleep since I was pretty excited about tomorrow, but in true post orgasm fashion, I dropped off pretty quickly, dreaming of showing off in sexy costumes and getting lots of attention from guys.

I awoke feeling super sexy and horny. I didn't usually sleep in my lingerie, but apparently I needed to do it more often because I woke up feeling like a sex kitten and ready to take on the world. I kind of wondered if I should take care of myself before going to the cafe, but decided I should wait.

So, I got up and showered, making sure to touch up on my shaving, especially for my face. I didn't grow much facial hair, but the last thing I wanted was five o'clock shadow on my first day. I changed out of the lingerie I slept in and pulled on a new set that I thought would be better with the French maid dress I planned to wear.