Cunt-ry Club

Before we begin I should tell you that my older sister is a whore although she calls herself a prostitute and my parents refer to her as a sex worker.

My parents eventually came to accept my sisters choice of professions a couple years ago even though they still disapproved.

Callie (my sister) is four years older that I was and what happens in this story began a little after I graduated from highschool at about the time I was looking for a job under my parents order that I either get a job, go to college or get out.

College wasn't really an option as we were not well off financially, except for my sister who made gobs of money and I had fairly poor grades in school.

Getting out wasn't a great idea either even though I really wanted my freedom but with no money or friends, I had nowhere to go.

So, a job was a priority.

And this is where my sister comes into the picture.

Due to a certain misunderstanding, my sister thinks I was gay or trans. I won't bother you with the sordid details but just tell you that once she walked in on me beating off wearing one of my mom's bras.

To me the bra was just jack off material but my sister now believes I am a sissy of some sort. The strange thing is that she began treating me better after that embarrassingly horrid incident.

Now back to my sister helping me get a job.

"Come work with me at the club. You'll make a ton of money and get to wear the kinds of clothes you like." Callie offered one evening after dinner. My parents insisted she come for dinner regularly. Ugh, she still thinks I wanna walk around in a dress or something... although?... no, absolutely not.

"Um, no thinks. I get the money and all, but I really dont want to be a gay sex worker." I said for the umpteenth time.

"Listen baby bro, there are plenty of straight jobs available. It has a hotel and restaurant along with a golf course plus lot of other things. There are plenty of jobs you could do without spreading your legs if you're really worried about that." she said placing a hand on my back and then added, "I know almost everyone there and could easily get you a job."

Yeah, I bet she did know everyone there, every guy that is.

I really did need a job but didn't really want one but out of politeness to my sister I asked, "I dunno, what kind of job would a guy like me get. My grades sucked."

"Ha, I dont think they give a shit about grades for most of the jobs. There's housekeeping, janitorial, kitchen help, bussing tables, grounds work... hell they even pay the towel boys twenty five bucks an hour to clean up in the locker room." she said.

I relented and allowed my sister to put in a word for me at the club. I was surprised when she came back not five minutes after our conversation to tell me I had an interview the following day at six thirty in the morning.

I guess she really did know people.

The following day I got dressed for my interview at Andolin Hills country club. I knew of the place through my sister. I had never been there before since it was a private gentlemens only club for the rich. I wore the slacks and white shirt my parents bought me just for job interviews and took an uber at my sisters expense.

I got to the gate (yes it had a gate) and presented myself.

"Hello, I'm Blair Ainsley here for an interview with Mrs Perkins." I told the attendant at the gate giving the name of the woman I was supposed to meet.

He looked at me with a funny look. This was nothing new since my name elicited looks like that. I hated the name but was stuck with it.

I was given a visitors badge and detailed instructions on where to go and not to go and then let inside.

I put the badge on and made my way to the main building making sure to use the staff entrance and then on to the office where Mrs Perkins was waiting.

"Well now, aren't you everything your sister said you were. You know we dont normally give interviews on such short notice but Callie is quite popular around here." she said looking me over. Yeah, I bet she was popular around here.

"Thank you. I'm kind of in a bind. I gotta get a job or move out since I can't afford college." I said omitting the fact that my grades were too poor to get into college. No need sharing that information on a job interview.

"I certainly understand. Many of our employees are working their way through college. Now if I remember what your sister told me, you're looking for something domestic? Well we have plenty of jobs like that." she said ushering me into her office and into a chair to begin filling out the multitude of paperwork that went along with every job known to mankind.

I looked at the paperwork and then asked, "Don't I fill these out after I get the job?"

"Your sisters recommendation is enough for me. Cleaning hotel rooms with occasional work helping out in the kitchen isn't exactly, well you know... It's not rocket science. Still, I do hope you know how lucky you are to have this opportunity. At twenty five dollars and hour plus tips many people would kill for this opportunity." she explained.

I filled out the paperwork remembering why I hated school but also thinking about the money I would be making. It took almost forty five minutes.

When I had finally finished, Mrs Perkins took the paperwork and then said, "All right then, everything seems to be in order, lets get you your uniforms and I'll show you to your locker and we can get you on the work schedule. You'll be training with Ashley for a couple weeks till you learn the routine."

I was led out of the office to a staff changing room in the basement of the hotel portion of the country club and to my utter humiliation, my locker contained five different colored short skirted maids dresses in my size.

"Your sister said you'd be fine with these. We have our own laundry service so we take care of cleaning your uniforms here. There's even overtime available from time to time working in the laundry if you want it." she said and then added, "Go ahead and get changed. Dealers choice on the color and I'll be back in a half hour to get you started."

I sat on the bench in the staff changing room wondering what to do.

On the one hand I did need a job and I was terribly curious about what wearing a dress felt like since I had been masturbating while wearing moms underwear for years but on the other hand.... wtf?

I decided to give it a try since I was absolutely sure that no one I knew would see me wearing it as no one in my income bracket ever went to a country club in the first place.

Panties came first and as always when I put on moms panties, my prick got hard as a rock. The stockings and garter belt took some time to figure out how to put on but I managed. The bra with small silicone titties sewn in also contributed to my raging boner. I stepped into what turned out to be rather comfortable girls shoes that were black with a white bow on top. A petit slip that flared out several inches was next and all that was left was was the dress it self.

I had considered wearing a dress before to jackoff in but never had the nerve to pull it off let alone the money to buy a dress so this was new territory.

Unsure how to put it on, I treated it the way a child might and instead of stepping into the dress, I pulled it over my head and as I did, I felt every bit a girly girl.

I was just trying to straighten the flared out skirts when Mrs Perkins returned and humiliated me by zipping the dress up for me.

"Yep, your sister was right, you are pretty. Okay dear, time to get started." she said and led me up into the hotel lobby. I kept trying to pull the skirt down to hide my erection as we walked but the swishing of the skirts around my pantied ass and stockings and garters only made things worse.

I was marched straight up to a girl perhaps two or three years older that I was.

"Blair, this is Ashley. She'll be your supervisor for a while, just till you learn your way around. Just follow her and do whatever she tells you." and with that I was left alone with Ashley, both of us dressed as maids, her in pastel purple and me in a more conservative black with white frilly trim.

"Okay, here's the scoop, it's real simple. It takes about twenty minutes to clean a room but we get a full hour just incase the occupant needs a little attention and that's where the tips come from if you know what I mean." she said and I definitely knew what she meant. I had no idea what I would do if the time came.

Together we cleaned three rooms from guests whom had already checked out. Two rooms were fairly clean but the third required a little extra effort as it looked like they threw a party in there. I did manage to get a good look at myself in one of the bathroom mirrors. I looked like a boy in a little girls dress. My body fit the dress pretty well but my face was still the face of a boy.

The fourth room was still occupied and Ashley was excited. Unlike the previous three rooms, this one had a placard on the door requesting maid service.

"Money time." Ashley said as she excitedly ushered the both of us into the room.

Inside there were two dudes sleeping together in the bed. It seemed obvious that they were gay. Ashley didn't clean anything, she just went to the side of the bed and knelt down and just waited. When she saw me just standing there like an idiot, she motioned for me to kneel down on the other side of the bed.

Bewildered, I just did what Ashley did and knelt down knowing damn well what I was in for. My sister had arranged for me to have this job thinking I would enjoy it.

We didn't have to wait long, each of the two men soon released their mutual embrace and rolled over to face opposite sides of the bed. Ashley took the man on her side of the bed and began to suck his cock while I stared at a large cock pointed at my face.

I was sickened but excited. Terrified but curious. Humiliated but willing.

I gingerly took the cock in my mouth like I had seen countless women do on the internet and while trying to keep my teeth off it, began to suck giving my first blowjob.

I tried to mimic the moves I had seen in countless pornos and way sooner than I had expected, my mouth was filled with a warm salty and gooey liquid. Spermy cum.

I wanted to spit it out but something about the taste and also knowing men like it when girls swallowed, I took it all down. Immediately after the two men blew their loads in our mouths, they turned back over to give their attention to each other.

The tingly erection in my panties was there for the whole time. God I needed to beat off in the worst way.

We didn't do any cleaning at all in that room and just after we left I asked Ashley, "So, how do we get paid for that?"

"Oh, were on the menu through room service. It'll be in your paycheck." she said matter of factly. She then showed me the payroll app and after she showed me how to log in I saw that I had been given a tip of two hundred dollars.

I had sucked a cock and wasn't really disgusted by it. I mean I was truly disgusted by it but I somehow like being disgusted by it.

Ashley then showed me to a small clipboard that listed all the rooms that had pre ordered special "Maid Service." There were code letters indicating what the guest wanted.

H was for a handjob.

G was for gay.

D was for a double team.

A was for anal.

O was for oral.

S was for spanking.

P was for straight pussy.

B was for any type of bondage.

W was for watersports. Ashley had to explain what that meant. It meant getting pissed on.

Numbers indicated how many maids were requested.

There was also a small chart on the back of the chart that explained what tip was expected for each service and I noticed that a G and and A together paid one thousand dollars.

Gay anal. One thousand dollars. Wow.

I went back and scanned the chart and sure enough someone had requested a G and an A for after lunch. It also has an O and a B which would pay and additional two hundred for each.

That came to fourteen hundred bucks for whomever was that maid.

I had never, ever ever considered having a cock in my ass but here I was wearing a maids dress having just sucked a cock and now had a belly full of another mans sperm and I was seriously considering it.

I pointed at the line on the clipboard where the afternoon gay anal request was and asked Ashley, "What about that one?"

"Oh you don't want that one honey. He always does more than he requests. I mean he always pays but you never know what else he's gonna add to his bill. Plus he likes anal and he's pretty big. I did him once when he requested a girl and it hurt like hell. Stay away from him. Also, he just loves leaving the girls tied up till he checks out for another maid to find. You get paid extra for that too but it kills your entire day." Ashley explained.

"So how do you know which ones to take?" I asked.

"If you see something you like, just put your four digit number under the line request so no one else will take it." she said then added, "If no one wants a particular one then someone might be assigned it but that rarely happens."

I looked over the sheet and only the one requesting gay and anal was still unclaimed. Probably due to his perverted requests.

I wrote my employee number under it while Ashley watched. I looked at her and said, "I need the money." Truth was, I did want the money but really I was curious as hell.

Knowing I was headed up to have a man fuck his cock into my ass, I went up to the room indicated on the clipboard and let myself in.

He was a big man maybe six foot six and seemed made of muscle despite his age of around fifty. He was naked and seated on a chair waiting for me.

"I never fuck men sweetie unless they are total failures of a man and have to wear a dress like a maid. Tell me sweetie, tell me you're a failure of a man and have to wear a dress and work as a maid?" he said softly but in a demanding way.

I hesitated before saying, "I'm a failure of a man so I wear a dress and work as a maid." The words burned but also excited.

He slowly got up and walked over to me and took me by the hand and roughly threw me on the bed face down and then demanded, "Say it again bitch. Make me believe it."

"I'm a failure as a man and have to wear a dress and work as a maid." I said.

"Louder bitch." He demanded. "Yell for me." He then spanked my pantied ass real hard three times.

"I'M A FAILURE AS A MAN AND HAVE TO WORK AS A MAID IN A DRESS." I yelled half crying from the pain.

He spanked me again three more times.

He then left me sobbing on the bed while he retrieved something from a drawer.

I soon found my hands being placed in leather cuffs behind my back. Then a huge rubber dong was shoved in my mouth and a strap was used to hold it in gagging me. I was then pushed up further on the bed still on my stomach when he took hold of my ankles and put leather cuffs on them and secured them to the corners of the bed to keep my legs permanently spread for him.

I was having second thoughts but all I could do was cry through the gag as no coherent words came out.

He got on the bed and soon I felt my panties being roughly pulled aside and a finger being shoved up my ass.

"Holy shit, I think I got me a virgin cunt here." he said as he began to finger fuck me.

One finger at first that was soon followed by another and eventually another. Fuck me it hurt. I seen women get the pussies plowed many times on the internet but I never knew that it could hurt. I knew nothing about ass fucking... nothing at all.

Once he finished fingerfucking me with three fingers, I felt his weight on me and his cock at my ass hole.

He pushed inside me and I never felt such pain in my life. I screamed through my gag and tried to beg for him to stop but he ignored my incoherent pleas for mercy and kept pushing on inside me.

My face was buried in the pillow and was soon becoming saturated with sweat and the drool that escaped while I tried to scream.

I dont know how long it took but eventually he was balls deep inside of me. He then started to fuck me.

I cried through most of it as he plowed me like a snow plow clearing the road. Like a chainsaw cutting me in half. It hurt and all I could do under his weight was take it. Him being a foot taller than I was, I was totally helpless and I began to hear my own words, "I'm a failure as a man and have to wear a dress and work as a maid."

The pain began to subside and soon my dick got hard again and without even being aware of it at first, I began humping the mattress in time with the cock that was pounding my ass. It began to feel good... real good.

I was still covered in sweat and my face was covered with smeared drool and somehow the dirtiness of it made me even more excited and I saw myself as a whore and liked it.

He pounded me for a good twenty minutes if not more before he made four or five truly violent thrusts and I could feel my insides being filled with his man seed, his jiz, his sperm.

A man was cumming inside me like I was a woman and it felt good.

I felt empty when he pulled out and just as Ashley had suggested, I was left bound and gagged on the bed for the rest of the day and all night. He fucked me two more times before he checked out the next morning.

It was Ashley who found me the next morning and she diligently cleaned the room before releasing me from my bonds.

"We called your sister and she told your family you worked a triple your first day to impress your boss so they know why you never came home. Get cleaned up and be back here tomorrow. A day off is one of the perks of being left tied up all night." she explained.

The pain in my ass was still potent but it also kept my dick hard as I made my way back the the staff changing room. There was another man and woman there getting changed into their uniforms. The guy was headed to the kitchen to work as a waiter and the girl, a maid. No one gave me a second glance as I changed out of my dress and into my old boy clothes.

I checked my payroll app and found I had earned one thousand dollars for each of the three gay ass fuckings, two hundred each for the spanking and bondage plus an additional five hundred for being left tied up all day and night. That came to three thousand and nine hundred dollars. I never did give him the oral he had ordered.

I was quickly coming around to my sisters lifestyle.

I cant wait till tomorrow. As I rode home again in an Uber paid for by my sister, I began to miss wearing the dress and began to wonder what wearing a dress out in public might be like... to live like a girl?

I knew I was gonna find out.