It's 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 of 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 then 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?
“It’s 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 emails, 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 losing 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 the 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 of 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 started 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 a debut this public?
“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 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, karaoke, 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 nights 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, it's 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, it's 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 anyway.
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 unladylike 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 a 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 mindset 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.
The black panties had several white ruffles along the back that were cute and sexy at the same time. I originally planned to wear a fancy bra with ruffles that matched the panties, but I decided to wear a corset instead and see how I did. I just wouldn't lace it very tight. I was getting excited just thinking about the cute and sexy outfit, so I quickly pulled the panties on and tucked my hardening clit away.
I decided to do my make-up again since that let me calm down last night. I decided to keep it pretty simple. I started with the liquid foundation. I wasn't sure if that was better or the powder, but I figured I could experiment with different looks on different shifts.
Once the foundation was nicely blended and I had that smooth even look, I went to the eye shadow. I went with a light pink color. I debated trying to do a darker color and go for the smoky look, but I remembered I was keeping it simple. So, I got the pink covering my eyelid and decided to skip trying eyeliner. I needed a lot more practice with eyeliner before trying it for my public debut.
I just did a quick pass with mascara. Not really doing things thick, just thick enough to give a little pop. I then put on lipstick. I went with a soft pink shade here. I found the color matched my eyeshadow pretty well, so it seemed to tie things together.
I then slid into my corset and did the door knob trick to get it tight. Basically, you tie the strings from the corset off to something sturdy, like a door handle and then walk and lean forward, so your own weight tightens the corset down. I could get my steel-boned corset down really tight that way. This time I got it just tight enough to squish everything in, but not restrict my breathing or anything. I slid my largest falsies into the cup. These were a decent size, giving me about a C cup with the corset. While I love the idea of huge basketball sized tits, falsies could get pricey, and I wasn't sure how in the way such gigantic breasts would be while working. So, I'd go moderate for now.
I slid on my back-seamed stockings, reveling in the feeling of the sheer material on my smooth skin. I hooked the tops of the stockings to the garter tabs hanging down from the corset and checked that my seams were straight. I admired my form in the mirror and with the exception of my relatively short hair, I looked like a really cute girl.
I grabbed my French maid dress and slipped it on. I struggled for a few minutes to get it zippered in the back, eventually getting it to close up. I wondered again if girls were supposed to be double jointed to get dressed. I squared the neckline so it showed a tease of cleavage. I then put on my long blonde wig, quickly brushing it out, then I looked in the mirror again.
Oh yeah, that was just an amazing feeling. I couldn't believe how good I looked and how good I felt. To be my femme self was just an amazing feeling. Of course, I could also feel it stirring in my clit, so I figured I'd better wrap up and get going, or I'd never get out the door.
I quickly wrapped the little white apron around my waist, pinned the white hat to my wig and then grabbed my white gloves. I tucked those into my purse along with my keys, wallet and phone. I then slid on a pair of Mary Janes with a chunky two inch heel. While I wanted to go with some sky high 'fuck me' pumps, I figured I'd better start slow and build up.
I bounded out the door, a spring in my step that reflected my excitement. There were still some nerves, too, but mostly just excitement. The drive over to the restaurant seemed like I was driving in a new world. The buzz I had from being out dressed was pretty intoxicating. I did feel like everyone was staring at me, but after a few minutes I was able to let that go, and just enjoy being out.
I pulled up to the restaurant a little giddy. I popped out of the car and saw a few other girls arriving at the same time.
A cute leggy blonde in a skimpy and sexy pink outfit came bounding up to me, “Are you Shawna?”
I nodded, “I am. You are?”
“I'm Tara Carolina. Everyone is so excited to meet you,” she gushed, giving me a big hug. She then looked me up and down, “Damn girl! Showing off on the first day? You are too damn cute.”
I blushed a little, but I was also taken in with her enthusiasm and excitement. It helped that I was already buzzing from being out, so this was just kicking it up. Even my nervousness was disappearing.
Tara waved to another girl that came over, “Candy! Come meet Shawna.”
A dark haired bombshell scurried over and gave me a big hug, “Hey Shawna, welcome! I'm Candy.”
I looked over their outfits and Tara was in a very pink, sexy and frilly two piece outfit. The top was a strapless wrap-around like a bandeau, the bottom was basically booty shorts, but in ruffled pink. Both pieces were frilly, her blonde hair hanging down loose, framing her bright smile and eyes.
Candy was almost the polar opposite, she had a tight red blouse that highlighted her cleavage paired with a short black skirt that was short enough to show off her stockinged legs, but was just long enough to maintain modesty, barely. Her dark hair was styled and pulled back.
They each took me by the arm and we walked arm-in-arm to the building, their energy filling me up. We came in the door like a tornado. The hostess, Talia, greeted Candy and Tara then, “Who's your new friend?” she asked. Then she looked again, “Wait… is this…?”
Tara nodded, “Meet Shawna, quite a step up from the suit, huh?”
“Oh honey,” Talia gushed, “You are super cute.” She pulled me in for a hug, too. This was so wild that everyone was so welcoming and friendly. I'd just gotten here and I already felt like one of the girls.
Candy tugged on my arm, “Come on, we'll go meet everyone.”
Talia said, “I'll let Don and Sandy know that you're here.”
Tara gave me a quick hug, “I'm going to get started on prep stuff. I'll introduce you to the kitchen staff when you come back.”
Candy took me around to meet the other girls, there were just a few other girls working. Lunch was apparently a bit lighter than dinner was.
We met Jessica who was also done in a French maid look, Melissa was done up a classic Playboy bunny with ample cleavage and Elizabeth who was looking very regal in a white wedding dress. We also met the bartender who was named Rallie. Rallie was done up in an equestrian riding outfit with full jodhpurs and a riding crop.
Candy then handed me off to Tara who introduced me to the cooks Jack, Mark and Paul. Jack was the sous chef, but the head chef wouldn't be in until dinner, so Jack ran the kitchen for lunch. There was something odd about all the line cooks that I couldn't quite place at first.
“Are all the cooks really short?” I asked Tara, realizing most of them were around my height or shorter, and at 5' 6” I'm not very tall. Not super short, but definitely under average.
Tara leaned in, “All the cooks are F2M.”
“Ohhh,” I said. “That's kind of a reversal.”
Tara just nodded and introduced me to Sandy, “Shawna this is the front of house manager, Sandy.”
“Welcome Shawna,” Sandy smiled and like everyone else pulled me in for a hug. She looked me up and down, giving me a big smile, “Wow, you really are cute.”
“Are you kidding me? I feel like a plain wallflower with how gorgeous all of you ladies are,” I shook my head, looking at Tara's super sexy look. Sandy was done in a super sexy all-black ensemble with a knee-length leather skirt, dark blouse and thigh high boots. She looked fierce and powerful, especially with her long dark hair pulled back in a tight ponytail
It was true. All of the girls were super cute, super pretty, super sexy or some combination of all three. Everyone was also really sweet and so welcoming. Like I said, I was the sort of person who never really fit it anywhere, but I really felt like I was vibing with the girls.
Everyone took some time to show me the ropes. Overall it was a pretty simple system and they used a tablet to enter the orders, which really streamlined everything and made it so you only had to carry one item. The check could also be done that way, too.
There were a few rules, but one that everyone hammered home was that any unwanted physical contact by the customers was strictly forbidden. Most of the guys knew that and knew they'd get tossed in a second if they got too frisky. It was also emphasized that there was to be no sex on the premises.
Since I'd waited tables before, I picked up the system pretty quickly. I started out with Sandy taking the tables and me shadowing her, but after lunch was over she had me start taking the tables directly and by the time dinner rolled around, I was flying solo with Sandy just staying close by in case I needed help or had a question.
As dinner rolled around, the rest of the dinner staff arrived. I met Kris who was statuesque and had a kick-ass punk rock look going on. She had a ripped Ramones t-shirt with a black mini-skirt adorned with several pins and lots of belts hanging off to match with her boots. Her hair was in a casually messy type look. There was Samantha who was going for a business look with a skirt suit in gray with a red blouse giving a pop of color and unbuttoned enough to tease some cleavage. Her bob style hair worked with the professional look.
I was amazed at how much fun I was having. The customers were all great, with lots of the guys flirting and offering me their phone numbers and e-mail addresses. Melissa said that would happen every night and she always had her pick of guys if she wanted a date… or a booty call… or whatever.
There was definitely a sexy vibe in the air and I was feeling so sexy and powerful as I went on that I started getting seriously aroused. With my hefty tuck I was steady dripping into my panties and they were getting soaked.
Even the other girls were in on the action as the girls all flirted and teased the guys and each other, too. There was no rule on the girls getting frisky and apparently a few of the girls would play up making out with each other. Apparently the guys would really tip heavily with those kinds of shows.
When Tara came up and started kissing me, I almost came in my panties. She left me breathless with just a quick smile and saying, “You taste sweet.” She patted my ass and walked away giving me a wink and a smile. It took me a few minutes to catch my breath.
This scene really caused me to test my tuck and a few minutes later I had a problem in that my clit had slipped out my tuck and I was making a pretty heavy tent pole in my panties. Thankfully the flouncy skirts on the dress hid a lot, but I knew I was going to have to get myself under control.
I asked Jessica to cover for me, so I could go to the bathroom. I went into one of the bathrooms, I realized there were multiple bathrooms and all of them were single occupant unisex rooms. It occurred to me with all the gender bending going on here, that was probably a very good idea.
I stepped into the gleaming bathroom which had a toilet, sink and lots of lights around the large mirror. It vaguely occurred to me that it would be good for doing make-up. I had just pulled my clit out and was debating how quickly I could jerk off when there was a knock on the door.
“Occupied,” I said quickly, but the door opened. Did I not lock it? I couldn't remember I was in such a rush. Sandy came in, closing the door behind her. I definitely heard the click of the lock there. With her in the Domme get-up I was even more excited than I was before.
She stalked over, smiling like the cat that ate the canary. She reached under my skirt and grabbed my clit with her hand, running her nails over my sensitive bits. I just moaned as her nails teased me.
“Having a problem, sissy girl?” she leaned in close, her lips inches from my ear.
My clit throbbed and I could only moan in response.
“Don't worry, it happens to all of us on the first day. We're actually surprised it took you this long,” she purred as she wrapped her hands around my shaft and started stroking. “You do want me to help you with this, right?”
I nodded and moaned. She then leaned in and kissed me, this wasn't a fun kiss like Tara's, this was a take-your-breath-away kiss. Though to be fair, Tara's kiss took my breath away, too.
She kissed over to my ear and nibbled on my ear lobe, which just made me throb even more, “Mmmmm,” she purred. “Does my sissy girl like that?”
“Oh my, yes,” I whispered. I felt like I was going to explode, but she was stroking just slow enough to keep me on the edge.
“I think you mean, 'yes Mistress', right sissy?” she growled, gripping tighter on my clit.
I gasped and blurted, “Yes, Mistress!”
She smiled and looked deep in my eyes, “Oh, good girl.”
I throbbed even more, and she said, “Oh does someone like being a good girl?”
“Yes, Mistress!” I squeaked out and she ran her nails over my balls making me really shudder in response.
“Okay, then my good girl, here's how this is going to work, Mistress is going to help you with your 'situation' here and I'm going to stretch your ass out. Then I'm going to suck you off and feed you your sissy cream. You're going to show me your full mouth and swallow like a good slut. Then you're going to kiss the toes of my boots and thank me.”
“Yes, Mistress,” I said, my clit throbbing even harder. I didn't think I could get more aroused than I was, but apparently I was wrong.
Sandy then moved me over to the toilet, sitting on the lid. She pulled me in close, her red lips wrapping around my clit head, her tongue tracing lines of fire over my head and her nails traced over my balls, across my taint and back to my crack. As she took my shaft into her mouth, she slid a greased finger up my asshole. It vaguely occurred to me to wonder where she had lube from, but that thought was gone as her finger slid into me. My head felt like it was going to explode now. She sucked hard and fast, while she pumped her finger in my ass at the same pace she sucked, which gave me this weird feeling like I was fucking myself in the ass.
I wasn't going to last much longer and told her. She took her mouth off long enough to say, “Beg to cum, sissy. Beg your Mistress for permission.”
I began begging in seconds, “Please may I cum, Mistress.”
“No,” she growled, between sucks. “Hold back, my little slut Shawna.”
“Oh please, Mistress. I'm so close, I can't hold back,” I begged.
She picked up her pace which was pushing me even closer, she ordered me, “Be a good girl, and hold back for Mistress.”
“Yes, Mistress,” I said, gripping hard and trying to hold back. I gritted my teeth and was getting past the point of no return.
A moment later, she hissed, “Are you ready to cum?”
“Yes, Mistress! Please?” I begged.
She just said, “Now, cum for me, slut.”
She kept sucking steadily and in no time, I was groaning with my orgasm. It felt like my clit exploded and as though fireworks were going off in my head. Sandy kept pumping my clit and ass for several moments, milking the orgasm out for much longer. She then held me tight to her as my body shuddered involuntarily.
She stood and pulled me in close, kissing me gently but deeply. Her tongue feeding my cum back into my mouth. Our tongues intertwined with my spending trading between us.
“Show me,” she ordered.
I obediently opened my mouth to show the pool of cum on my tongue.
“Good girl,” she smiled proudly. “Swallow.”
I gulped down the mouthful of jism, the familiar taste of my own juices making me somehow hornier.
“Very good girl,” Sandy said. Then she stepped back and pointed down to her boots.
I quickly knelt and kissed the toe of each boot, feeling a surge of excitement as I did so. Was I really ready for this? Whether I was or not, I was enjoying the hell out of this.
“Good girl,” she purred. “Stand up.” As I stood, she smiled at me. “Did you have fun?”
I nodded, “Yes, Mistress.”
“Good, then we have one more item,” she held up a small plastic item. It took me a moment to realize it was a chastity cage. “This will make sure you don't have any more issues during your shifts.”
My breath caught with my excitement. I'd always loved the idea of being a caged sissy, but somehow the idea of it actually happening was both scarier and more exciting than I believed.
Sandy manipulated my bits for a few moments. I wasn't entirely comfortable for parts of it, but then I was swiftly caged up. The click of the lock made me thrilled and I squirted a little.
Sandy caught the bit of pre-cum on her finger and held it to my lips. I dutifully sucked it clean.
“Are you ready, girl?” she grinned.
I looked down at my locked up clit, thrilled but also a little scared where this was going.
“Yes, Mistress,” I replied.
“Just Sandy for now. We'll talk more about the possibility of more 'Mistress' for you later,” she then leaned in and kissed me softly. “Now, fix your make-up, we'll cover you for a few more minutes.”
Sandy headed out and I moved over to the sink. I washed up, then I realized my make-up was in my purse in the back. I just cleaned up as best I could and hoped I didn't have that 'freshly fucked' look. I was pretty sure I was failing miserably.
I took a deep breath and headed back out to the floor. It took me a few minutes to get back in the right headspace, but once I got going, I was back on. I was definitely able to focus much more, though there was a subtle feeling of being horny underneath everything.
Samantha pulled me aside at one point, “The girls all want to take you out after the shift to celebrate your first day. You're probably going to be sore and tired, so we'll keep it quick. What do you think?”
“Absolutely! You girls are the best,” I said. Samantha pulled me in and hugged me.
“Do you have something else to wear?” she asked. “Most of us bring another outfit to change into.”
I shook my head, “Nope, I didn't even think about it.”
“Yeah, I figured,” she said. “Talk with Rallie. She always seems to have a dozen outfits at any time and I think you're about her size.”
The next time I was over at the bar picking up an order, I said, “Rallie, apparently the girls all want to go out after work. Do you have something I could change into after work?”
Rallie looked me up and down, smiling big, “Yeah, I have a little black dress that should fit you. It's pretty slinky, but it's a great dress.”
“You are awesome, thanks girl!” I smiled and bounded away. I couldn't believe how awesome this night was.
The shift wrapped up, I was cut a little early to give me extra time to learn what side work I needed to do and how to fully check out. I was amazed that I pulled down several hundred dollars in tips and it was my first night. I forgot you could actually make some decent money as a server. Since a lot was done digitally, there was very little cash I actually handled which helped make things easier at the end of the night.
Once I was done, I found a shiny black dress hanging in the back with a note that just said “For Shawna. Enjoy! Rallie.”
I looked at the dress, trying to figure out why it was so shiny. I ran my hand over the smooth material and realized it was PVC, or maybe patent leather? Either way it was a really nice dress. It was also going to be pretty sexy.
I slipped into the small storage area in the back that the girls apparently used as a changing area. I slipped off my maid's dress and slid into the slinky black dress. This dress was magical. I felt so powerful and sexy in this dress. I applied some more make-up in one of the two well-lit mirrors in the space. Melissa and Samantha came in a few minutes later.
Melissa whistled, “Damn girl! You looking to break some hearts?”
I smiled and laughed, “It's Rallie's she letting me borrow it.”
“Then do yourself a favor and get one of your own, because this look works on you. You mind if we get changed?” Melissa asked, she was already taking her bunny ears and the wrist cuffs off.
“Sure thing, just… you girls are all so cute and sexy. I don't want to get worked up,” I said in the mirror.
“It happens to all of us. There's such a vibe of sex in the air, it's sometimes hard to keep under control, but we usually keep things well in hand,” Samantha said. As she said, 'in hand' she winked at me. Did they know? I guessed everyone had some idea what happened. Sandy said it happened to everyone on their first shift. I wondered if they knew I was locked up now?
“So, how do you keep under control?” I asked, putting my make-up back on.
“I'll show you,” Samantha said, stripping off her outfit and just standing in her bra and panties. She showed me the medical tape she used to tape herself back. “Medical grade tape will help keep under control under even the most stimulating of circumstances.”
“Wow!” I said, then I blushed red at seeing her in just her undies.
“It's okay, sweetie,” Melissa smiled. “You're one of the girls now. Of course, the girls are a bit friendlier with each other than the guys are.” She capped this statement, by blowing me a kiss as she slid into a mini-skirt and tank top.
I finished up and headed out. All of the girls got changed and we all agreed to meet at a nearby alternative bar called The Cauldron. Everyone met around the same time and we came in like a tidal wave. Apparently the girls came here after work a lot, so the bar knew what to expect. I did get a lot of looks in Rallie's dress, so maybe I would have to look at getting one of these on my own.
Most everyone wanted to get back to their lives, but they all wanted to welcome me to the fold. One thing almost everyone did was tell the story of their first night and at what point they had to sneak off to 'relieve some stress'. It was apparently something of a right of passage with the girls.
A few of the girls related their tips for keeping things under control. Some used a gaff, others used medical tape. A few girls who were on hormones said that usually helped them balance out.
Elizabeth added, “Though all of us were given a bit of help to start out.”
I looked aside at her and was about to ask what she meant, but Tara interrupted.
Tara led a little toast to welcome me. She said, “Everyone raise your glass…” Once everyone raised their drink, she continued, “Welcome the new cutie to the girls of Femboy Hooters. May your skirts always flounce properly, your seams stay straight and everything else hit the right spot.”
Everyone took a drink, I sipped my drink and said, “Femboy Hooters? I thought it was the 3-D Cafe?”
Kris leaned over, “That's the official name, but everybody just calls it Femboy Hooters. We started joking about it early on and it kind of stuck.”
“But none of us wears a uniform,” I noted.
“Actually the French maid dress is kind of the standard, so you're already working in the uniform. Also a few girls will wear a Hooters uniform,” Jessica teased.
“By the way, that dress looks good on you. You should keep it,” Rallie said looking me up and down.
“What? No. I can't do that,” I said, amazed she'd offer that.
“Oh, don't worry, I'll borrow it back when I need it, or maybe I'll use it as an excuse to invite myself over and get it back… with interest,” she winked at me. I blushed, but also thrilled at the idea of playing with the cute Rallie.
Sandy then stepped up, “So girls. You know what happens with our new sissies. I have her key here, so Candy, I think you should start things off this time.”
Sandy handed the keys to my chastity over to the dark-haired bombshell who looked at me and gave me a wink.
Sandy said, “You girls know the rules, but let me explain it for Shawna. Each girl will get a turn with your keys and you have to 'earn' the keys from that girl. Who will pass it to the next keyholder… Once everyone has introduced you to the group, the keys will come back.”
I blushed scarlet red and all of the girls piped in about what they were looking forward to doing with me. A few girls related the stories of their initiation and how much fun they had. I thought back to the girls kissing each other and wondered just how frisky the girls would be with each other.
All in all, it was a nice time, even if it was a little short, but it was so nice getting to chat with everyone and how welcoming everyone was. It really did feel like I'd found a group of sisters, everyone giving me a hug and a quick kiss on the way out.
As Candy headed out, she got my phone number and texted me an address. “Come to that address in the morning. Do you have something more casual to wear?”
I nodded, a little worried about where this was going.
“Good, just wear some light make-up, and don't worry, this will be a lot of fun and you'll be looking fabulous for your shift tomorrow,” Candy smiled at me.
I slept a little uncomfortable that night since the cage kept me from getting hard and I kept waking up from the discomfort. Finally in the morning, my attempt to get morning wood actually got really uncomfortable and I eventually pulled out my dildo. I laid in bed in my lingerie and used my dildo multiple times, but after a while I was just getting more and more frustrated. So, I just got up and got started with the day.
I dressed in my mini-skirt and black stretch top combination I'd worn earlier in the week. I paired that with a pair of three-inch heel pumps so I could get myself used to being out and about in high heels. I put my Mary Janes in the car along with my maid dress pieces, for later at work.
I was feeling pretty sexy and femme as I drove to the address Candy sent me. I pulled into a shopping center and realized the address was for a hair and nail salon called 'Perfect Shape'. Oh wow! I was going to get a make-over? Well, this was not really how I expected this to go.
I walked up to the store and Candy met me at the door. She smiled big and gave me a big hug, “Hey girl, ready to get your nails done and your hair done? Well, not your hair, I figure you're still using a wig?”
I smiled back, “Yeah, it's a wig. I never really thought I'd do something like this.”
“It's a pretty wild experience, but you'll feel great and look amazing. If you grow your natural hair out, I'll bring you down and get you the full experience, but just getting the mani-pedi, facial and make-over is just amazing. I've got you scheduled with Julie, she's great and she'll go through your colors and give you some tips on really stepping up your make-up game,” Candy explained.
We went into the salon and Candy introduced me to Julie. Julie explained everything so fast it made my head spin. Before I really knew what was going on, I was in a chair, my shoes were off and one girl was attacking my feet and toenails, while another was working on my hands. While that was going on, Julie was looking at my face in the mirror and talking about the areas to highlight and the colors to use. It was all a lot to take in, so I mostly just nodded and said 'Yes' to whatever I was asked. Hopefully, I wasn't being asked anything too crazy.
My feet were also a little ticklish, so some of the work on my feet was really distracting since I was trying to not squirm or giggle too much, but it wasn't working. When Julie started rubbing some cold cream on my face, I almost jumped out of my skin!
Soon the face work was the most distracting part. I'm not sure what all they did, but some of it hurt and some it felt like popping pimples. I wasn't sure what to make of it, but it looked like Candy was going through the same thing, so I tried to relax and go with the flow.
After a while, the work on my feet and hands moved to just the nails and then Julie started working on my make-up. She made sure I was paying attention and gave me suggestions on colors. She was going slowly with the make-up and showing me how to do some simple tricks to up my make-up game.
When she was done, I looked like a new person. I was always amazed what a little make-up could do. She didn't even really do that much, she just knew how to make it work.
“You'll just need to practice, but if you're working the cafe, then you should get lots of chances to practice. In fact, I'll see you on Saturday night,” she winked as I got out of the chair and looked at my fingers and toes. I've painted my nails before, but having the matching colors was one thing, but I realized they'd put fake nails on my fingers! They weren't very long, just a little past my finger tips, but it was wild to have long nails for the first time in forever.
Candy gathered me up and we made our way over to the cashier. Thankfully I still had a lot of my cash from work, so paying was no problem.
“Obviously, it's a bit pricey to do this every day for work, but eventually you'll get good and just need to stop in for some maintenance,” Candy noted.
“How often do you come in?” I asked.
“About once a month or so, it depends on how much I need to touch up my roots or anything,” she said.
I nodded, then I almost jumped out of my skin again. My cousin Kelly walked in the door. Holy shit! I forgot this was the salon she worked at. She just smiled as she walked past. She gave me an odd look for a moment like she recognized me, but she moved on without saying anything.
Candy led me outside, “Are you okay?”
“Uh, yeah, my cousin works as a hair stylist here. That was her,” I explained.
“Oh… and she doesn't know about Shawna?” Candy asked.
I shook my head in response. Candy shrugged, “Well, she sees a few of us in there, so I doubt she cares that much. She might be a good one to come out to, if you think you want to do that.”
I shrugged, “I hadn't really thought about it. We'll have to see. Thank you, this was a lot of fun.”
“Yup, I figure it's a nice way to get you feeling your feminine best. So, I'll be passing along your key, so you and I are done, but we should still go out sometime.”
“Really?” I asked. “That would be amazing, thank you.”
Candy gave me a big hug and we both headed to work. I practically skipped into the cafe, or Femboy Hooters as we were apparently calling it? Talia wasn't working the door, there was a very petite girl named Blake who was working. She was done up as a goth cheerleader. All she needed was the anarchy A and she could be one of the girls from the Nirvana video.
“Are you Shawna?” she asked. I nodded, and she got a huge smile. “I'm Blake, Sandy told me all about you! It's so great to meet you!”
She gave me a big hug and her smile was infectious. She had a really bubbly energy that could be annoying if overdone, but she balanced it out with being very sweet.
“Its great to meet you, oh wow! I love your nails, those look great. Nice color!” she gushed.
I blushed a little, “Yeah, Candy just took me to get them done.”
We chatted for a few minutes then I said, I needed to go get changed. She replied, “Oh great! I can't wait to see you in your 'uniform'.”
I went into the back to get changed. The statuesque Kris was there, she was done up in a much different look from her rocker look. She had a small floral skirt with some coconut halves on her breasts and a lei around her neck. It was a very fun and sexy look.
She greeted me with a big hug, her coconuts pressing into me, “Hey Shawna, sorry about my nuts.” She gave me a wink.
I laughed and told her how great she looked, she beamed, “Oh look at you, cute and sweet. I'll see you out on the floor.”
Samantha was working on her make-up, her slutty MILF look with the blouse unbuttoned very far down, the pencil skirt was very short. Her long brown hair pulled back. As she finished she slipped on her four-inch 'fuck-me' pumps.
She looked up, “Hey girl, Tara wanted to see you when you got in.”
“Thank you,” I replied. “How do you manage those heels for the whole night?”
“Oh, you build up to it. I started just wearing them for an hour or two, then I just kept building it until I could manage a double in heels and still go out dancing,” she explained.
I quickly got changed into my French maid dress; as I did, a tall, raven haired girl came in. She introduced herself as Tamra. Of course, she gave me a big hug. As I hugged her, I realized her dress was the same shiny PVC material from the dress Rallie let me borrow.
“Is that PVC?” I asked, my hands lingering a bit longer than was probably appropriate, or necessary.
Tamra to her credit took it in stride, “It is, isn't it great? I love the feel and the look is just amazing. I'll probably wear my latex dress tomorrow if you want to check that one out.”
“Oh, wow. You have a latex dress?” I asked. “I've tried to do latex before, but it always ripped after one or two wears.”
“Was it cheap?” she asked. When I nodded, she replied, “Yeah, that's the problem. The good stuff is really pricey. I think I know what we'll do when it's my turn with you. There's a local shop that sells some good quality stuff, we can check it out.”
She put the finishing touches on her make-up as I went out to start my shift. I got my table assignments and went to look for Tara. As I passed by one of the bathrooms, she came out dressed in a Harley Quinn costume, the 'Daddy's Little Monster” version. Her version had some seriously short shorts and her blonde hair was done up in a double ponytail for it.
Tara gave me a big smile and a hug. As we were about to start talking, a gentleman also came out of the same bathroom with a big smile on his face.
I looked from him to Tara questioningly, “Did you… and he…”
Tara just smiled and nodded.
“But I thought one of the big rules…” I started.
Tara jumped in, “It is, but just don't be obvious about it. A lot of us have a little fun. I mean, come on, things get way too sexy out here, you've gotta take the edge off somehow.”
I nodded, “Wow, that's wild. I'm not sure if I'd have the guts to do anything like that.”
Tara looked at me sideways, “It's easy, girl. Especially with how cute and sexy you are, you'll have the guys lining up to take a shot at you.”
I giggled, “Well, thanks. I guess what I mean is that I… uhhh… haven't uhhh…”
Tara looked knowingly, “Oh, you haven't been with a guy yet.”
“No,” I shook my head. “I mean, I've… used… toys, but…” I blushed about six shades of crimson.
“Oh, you're adorable. And you're right it's not quite the same, but that's fine, because I had planned for us to go out tonight after work, but now we have a goal. We're getting you some dick!” She smiled.
“Tara!” I gasped, then giggled.
“It's my turn,” she held up my key, and I blushed some more. “We're at least going out. What you do is fully up to you, but I know you want to experience being a girl fully, right?”
I nodded, not really able to form words, feeling like I was finding new levels of red with my blushing.
Tara gave me a hug, “It's alright, girl. I'm going to be with you. This is what having sisters is all about!”
She gave me a quick kiss on the cheek and made her way back to the floor. I went to work, hoping to distract myself from my thoughts about what tonight would be like. It was Friday, so things picked up quickly.
Apparently, the lunch crowd rolls right into the happy hour crowd and right into dinner, so soon I was jamming away at the tables. Thankfully even with it being busy, they kept our number of tables small so we could spend a little more time talking with the customers and showing off, even getting some photos with the guys.
I got to talk with several of the guys and found quite a few of them were regulars and came multiple nights a week. I didn't catch all of the names, but there was R.J., Dave, Peter, Jay, Bill, and others.
It was really great how nice and sweet most of the guys were. Sure they wanted to give me their phone number or their email address, but they weren't pushy about it. A few of the guys later in the evening had a little too much to drink and started getting a little pushy. Sandy was there in a moment and very quietly, but in that very commanding way warned them. She also reminded them, they got one warning; mess up again and they were out.
I was impressed how fast she and the other girls took care of things. She didn't do it in a big way to embarrass them, she did it quietly, but made sure they knew she was serious. I guessed her dominatrix look probably helped with that, too.
The guys were very apologetic and were well behaved after that. They did ask if I'd pose for a photo, so we did and they left a very nice tip. They also left their phone numbers, so I guess they were hopeful.
Interestingly, there were some ladies that came out, too. Not just trans girls, but genetic girls as well. Jessica mentioned that a lot of the ladies felt more comfortable here. Though some also came done up to try and show out as well. It made for a wild vibe on the floor and everyone would get pretty worked up. It certainly had me ready to go out on the prowl.
Again as the new girl, I got cut a little early, so I had time to clean-up, do my side work and prep work, plus I was able to redo my make-up and slide into the PVC dress Rallie let me borrow.
So, when Tara came to find me, she just gave me a big smile, “I guess you're ready to go out?”
I nodded and she got changed, too. As she did her make-up, I asked for a few make-up tips and pointers, so she was happy to show me a few ideas. As we headed out Tamra and Melissa joined us.
We hit a club that the girls regularly went to. So, several people knew all the girls. Quite a few of the guys also asked to meet me. On the one hand, I felt like fresh meat in a pack of wolves, on the other hand Tara, Tamra and Melissa kept me close and made sure the guys knew to back off until I was ready.
We got a table and got some drinks. I don't really drink much, so I made sure to get a virgin daiquiri.
Tamra laughed, “Gotta keep something as a virgin tonight?”
“You are incorrigible!” I told her.
“I don't know what that means,” she laughed. “I mean that literally. But I'm going to guess it means: I'm a bad girl. Watch out though, if you aren't a bad girl tonight, well, I might have to put you over my knee.”
My submissive side really wanted to see if she was serious about that, but I also didn't want our relationship to go that way. Well, not yet anyway.
Tara told me that she had a room for the weekend, so if I wanted to get wild, I didn't have to worry about taking someone home.
Suddenly Tara gasped, “Oh! I have someone you have to meet. Greg!”
She called over a tall guy who gave her a big hug and a quick peck on the cheek.
“Greg, you have to meet my new friend, Shawna. Shawna this is Greg. Greg comes to Femboy Hooters fairly often, though you haven't been there in a couple weeks,” she said accusingly at him.
Greg smiled as Tara playfully swatted his arm, “I was traveling for work, but believe me, if this lovely lady is there now, I'll happily come back.”
Greg stepped in and we chatted a bit. Apparently, he and Tara had a 'friends with benefits' kind of thing going. Neither were really interested in a relationship, but they were both really attracted to each other. Greg was very nice and I could see why Tara liked him. He was easy going, but had a quiet confidence. He was also cute. I wasn't sure about his age since he was slightly graying, but had a youthful face.
After a while of hanging out and talking, Greg and I got closer until he very gently and suddenly kissed me. To say my heart was hammering was an understatement. Being locked in the cage had me really horny and it only took a few minutes of kissing like that before I asked Greg if he wanted to go back to the room.
He smiled in response, and in a swirl we were at the room Tara had held for us. It was a small room, just an efficiency with a small kitchenette, a bedroom and bathroom, but let's be honest, for this, we really didn't need a lot more. I did have a text from Tara that said to take our time, she was going home with someone else, so we could play as long as we wanted.
Greg was very sweet as you'd expect, taking his time with kissing me and slowly working me out of the PVC dress. His hands caressing me and making me feel like such a woman. I was also exploring him and eventually got to 'down there' and realized he was well-hung, but not huge.
I slid his cock out of his pants while his mouth found my sensitive nipple and his sucking on my sensitive buds caused me to moan. My hands explored him to enjoy my first time playing with a cock that wasn't my own. I stroked up and down, while feeling his balls with my other hand.
I was a little hesitant at first, but then it occurred to me, I knew what I liked for oral, so I figured I could do the same things. So, I kneeled down and started simple. I licked the sensitive underside all the way up and down, which got some nice moans. I took that as approval and licked up to swirl my tongue around his cockhead, tasting the sticky sweet dab of pre-cum that was already dripping from him. Then I licked back down to run my tongue over his balls.
That really got some noises out of him, so I did that for a few minutes before moving back up and ran my tongue over him to get him nice and wet, then wrapped my lips around his shaft and started gently sucking him into my mouth. I bobbed up and down a few times, getting a little deeper with each thrust. I was enjoying seeing my lipstick marks going further down his length each time.
I got a little too overzealous and tried to take him deep throat and instead wound up making myself gag and cough. I took that moment to go back to stroking him, while I cleared my mouth and pulled a stray pube out of my mouth as well.
I was really enjoying the hell out of sucking his cock, and I wanted more. So, once my throat was settled, I started sucking him down again. He gently ran his hands over my hair (well, okay, wig) and shoulders, murmuring his approval. Punctuating it with moans and groans. I have to say hearing all the noise was a hell of an ego boost. I felt powerful and also kinda slutty, but I was enjoying both parts of it. I was now wondering if I could make him cum like this.
I wanted to practice my deep throat first, and Greg didn't seem to mind, so I kept working deeper on his shaft again, then when I was ready, I very slowly got him to my throat, opened as wide as I could and gently pushed. It wasn't quite like deep throating my dildo, but the results were much more fun as he began muttering “oh fuck, yeah” over and over.
I pushed slowly up and down like that, pausing to take a quick breath now and then, and also letting some spit drip out, until I had him comfortably in my throat and began really bobbing up and down in earnest. The noises he was making now were making me absolutely drip in my cage. My panties were already wet when we started, they had be about soaked by now.
We went like that for several minutes. I was starting to get tired, but I didn't want to tap out yet, so I kept going when he said the words, “I'm gonna cum.”
That spurred me on and I was able to bottom out and take him balls deep as he groaned hard. I pulled back and began bobbing most of the way down his cock, feeling him spurting in my mouth was one of the hottest things I've ever experienced and I had a little mini orgasm. I could feel my clit squirting as he shot stream after stream of cum in my mouth.
He looked down at me, panting for air, “Holy shit, girl. You've really never done this before?”
I looked up, smiled and showed him the load of cum in my mouth before I made a show of swallowing. The taste was odd. Mostly a little salty, the texture was more the odd part, but I'd eaten enough of my own cum to be used to that. It was interesting that his tasted quite a bit different than mine. Not bad, just different.
I smiled up at him and shook my head, “Nope, never with a live cock. I've practiced quite a bit with my toys though.”
“Well, that was amazing for a first time, mind-blowing, so to speak,” he laughed. “Give me a couple minutes and we can see what other firsts we can get you through.”
I smiled as he pulled me up and kissed me. I was a little surprised since I thought some guys weren't big on kissing after blowjobs, but he didn't seem to mind at all. In fact, making out was definitely having the right effect on him and soon he was poking me in the stomach with his hardening cock.
“How do you want to be?” he asked.
I shrugged, “I don't know.”
“Then lay on your back, I want to watch your face as you take me in,” he said.
He kissed me again as laid me back on the bed. He pulled my panties down and commented, “These things are soaked, girl.”
I blushed a little, but felt oddly proud, then I gasped as he slowly worked one finger into me. I moaned as he fingered me for a few minutes before working a second and finally third finger in. I was thrashing about, moaning and groaning, my clit absolutely throbbing in its cage.
Greg leaned in to kiss me again, then stood up, pulling his slick fingers out, he lubed his cock and pressed it to my rosebud. He'd opened me pretty well and the first few inches slid in quickly, making me gasp and arch back. It felt like my brain was going to short-circuit.
He stayed there for a few moments, letting me adjust before he pulled back and thrust in again deeper. He kept working me like that, making me hornier and hornier until he finally bottomed out and I was begging for him to fuck me.
He took pity on me and began sawing in and out slowly. This elicited new waves of pleasure and all sorts of new noises on my part. My eyes focused briefly and I saw him watching me. I smiled up before my vision blurred again and I rode the crest of another wave of pleasure. When he picked up the pace and began really slapping into me, I almost screamed.
I managed to clamp it down into a strained groan, but the smile on his face said he knew that he was hitting the right spot. I wrapped my legs around his back and he laid down on me, kissing me as he began slamming into me.
The intensity overwhelmed me and the strange sensation built slowly in my toes and moved quickly through my whole body erupting through my brain and out my clit. I'm not really sure what happened but everything overwhelmed me quickly and I must have blacked out.
I came to and Greg was looking down at me, “Are you okay?”
I groggily smiled and said, “Yeah, just… that was intense.”
“I'll say,” Greg replied. “I didn't think I was going to cum again, but your sissygasm was so hot to watch, well, I came really hard.”
“Oh, I kind of wish I'd been awake for that,” I muttered.
“Well, that gives us something for next time,” he said and kissed me. “I'm slipping out.”
He pulled out, which was a really strange feeling. First, suddenly felt very empty, and I wanted to be filled again. I also realized there was a huge amount of cum dripping out of me. I rolled to my side and eventually was able to walk over to the bathroom and get cleaned up.
Greg and I flopped into the bed. Cuddling after the intensity of everything, it was very nice and before too long I dozed off into a quiet sleep with a big smile on my face.
I was definitely enjoying being a girl.