Author's note: This was inspired by the world of staciliv's "Another Really Stupid Bet." (Go read it now!) It inspired me after many years to write a follow-up with her gracious permission, and then a few more chapters about putting your money where your orifices are.
Disclaimer stuff: This is a work of fiction.
"Smile Puta!" The photographer instructed. "You must look your best for your debut!"
The asshole was joking. Nobody can tell the difference between a smile and a grimace around a ball gag. Still, I thought, I never looked better: A curvy five foot four inch woman of Puerto Rican heritage with golden skin, chocolate brown hair done up in a chiffon. A professional did my face, and my lips and nails shine with a bright red color. My D-sized tits (my girls!) are supported by a demi-cup harness. I'm forced to push them out standing in these stilettos locked on my feet and knee highs. I look like a lingerie model except for the ringed collar around my neck, wrist and ankle cuffs. One of the bouncers pushes my feet apart, widening my stance.
The photographer circles me, taking closeups. When the he crouches in front of me for the money shot, I thrust my freshly-shaved kitty at him in an act of defiance.
The photographer laughs merrily, "Such a hungry cono!" As he stands he give my belly a little pat. "Don't worry little cono, Semental will feed you soon." He slaps my ass as he steps away saying, "Ride hard puta!"
How did I get here?
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It was a stupid idea in the first place, but I had nothing for me in the States. I lost my job when my boyfriend John stole my car (and later I found out my laptop) so I couldn't get to work waitressing at the local bar across town or look for something online. We got into an argument the night before because I wouldn't give him a blowjob after he went down me. What is it with men wanting to stick their dicks into places they don't belong? I just don't like fellatio. I can eat pussy with gusto, but cock in my mouth bothers me.
Losing the car reminded me of my best friend Staci. It was originally her car. She got into some money trouble and went down to a bordello in Matamoros called Semental. We visited it a few years ago for our friend Margo's bachelorette getaway, along with our other friend Lisa. The bordello had an outstanding $10,000 challenge for women to ride a fucking horse, also called a Semental, for three minutes and get off. Staci said she would return in a couple days, but never came back, giving away everything she owned in the States.
I knew what happened to Staci. The Semental website had subscriptions where you could follow your favorite whore. I guiltily signed up (only $4.95 a month) to see pictures and videos of Staci in a gangbang or being hooked up to a milking machine, drool leaking from her ball gag. My "favorite" by far was watching her rematches with the Semental. I could see her trying to concentrate enough to get off of the horse in time to win, but every time she fell back into riding her mechanical lover into an orgasmic daze, followed by a marathon series of blowjobs until she was a cum-soaked mess. How could she be so cum drunk she would forget to stand up?
I told myself I was watching to look out for my friend, but I would stroke my kitty's clit to Staci's rides. Although I fantasized about it, I doubted the Semental challenge would work on me: I cum rather quickly and my clit gets too over-sensitized to orgasm any more. I'd be able to keep it together and hop off the second I had the chance.
I was out of a job and a car, and I was going to be kicked out of my apartment soon, so I said fuck all and decided I would take the Semental challenge. I applied online borrowing Lisa's PC and within the hour got in touch with the bordello. They agreed, but they needed me to stay in town at least a couple weeks while they prepared. When I told Lisa and the now-divorced Margo, they offered to come along, but I said no. I told them not to worry and that I would even find and convince Staci to come back.
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A large man from the club picked me up from the airport and drove me to Semental's. I didn't notice last time but it was actually a pretty legit operation. The "front" was a nice hotel where families could stay. It even had an indoor pool. The bordello side was connected at the back of the hotel bar/restaurant, separated by a beaded curtain. Burly bouncers made sure nobody got the two sides confused.
I talked with Julio, one of the managers. He was very attractive in a nice suit sitting behind a high, large desk. He told me I would have to get a very thorough physical, warning me that it would be VERY intense. He explained that although the challenge is simple, the club had to make sure the girl wasn't going to have health issues during her ride. (Besides being fucked out of her mind by the horse, I thought.) The waiting period was for the test results to return and to prepare the Semental for its challenger. I agreed and signed a small stack of paper.
We chatted for a bit. I told him about my first visit. He nodded and explained that a lot of changes have happened. When I asked about seeing Staci, he shook his head and said that while I was a good girl to worry about her, I wouldn't be able to see her for now. I sheepishly mentioned that money was tight and asked if he knew some respectable, albeit cheap, places in town.
"You said you were a waitress on your application. You can stay here and work for us," Julio suggested. "You won't earn that much money though." He warned.
I was taken aback by Julio, but then he laughed. "No, not that, you misunderstand. You look like you would fit right in our restaurant and bar as one of our waitresses." I remembered seeing the girls in the traditional billowing white blouses and long colorful skirts as we walked past the restaurant to the elevators. It seemed tacky but tame.
"Our girls live in a communal space on one of the lower floors of the hotel, below the office," he continued. "You may stay there for a small fee. I must warn you that our matron Mrs. Montenegro runs the place like a convent." He wagged his finger at me, "No hanky-panky, no men. Understood?"
Being celibate for the next few weeks would be just what I needed after my train wreck breakup. Cheap room, board and I get paid? "Sign me up!" I smiled reaching over to shake Julio's hand. We added a direct deposit form to my papers.
The office shared the floor with a large clinic where I had my examination with two of the doctors on staff. Doctor Smith was an older graying man, while Doctor Cruz was young, tall and handsome.
Unfortunately for me, Doctor Cruz had a bedside manner like a drill sergeant. He marched me into an examination room, told me to strip and give a small urine sample before ordering me onto the examination table. He started measuring every inch of my body, taping electrodes and leads everywhere. He took some blood samples. He dragged me from the table to a corner with some rulers on the walls and had me do some poses buck naked.
"Bend more!" He ordered, as I touched my toes. I heard the snap of a camera behind me and I covered my crack.
"Do not be a baby," he scolded, "We are doctors and this is for your medical record, not for InstaPorn!"
I removed my hands and gave him the finger before turning back around.
I was glad Doctor Smith was the OB/GYN. He was very understanding. He recorded the long history of my sexual adventures with men, women and women with men without batting an eye. Doctor Cruz came and took some very intimate measurements of my waist, belly, vag and even my asshole, but Doctor Smith did the actual examination. Doctor Smith gently explained every test and warned me when something was going to be painful. I screamed and almost jumped out of the chair when he shocked my poor pussy and nips on my girls.
"I'm sorry Maria, the Semental use some TENS technology," he explained, "We have to know your limits. We don't want you to have a heart attack during the challenge."
Julio wasn't kidding when he said the exam would be intense. My face went beet red when Doctor Smith used a powerful vibrator to masturbate me to a loud orgasm. "STOP IT! STOP IT! I'M TOO SENSITIVE!" I screamed as I sat up and dove to protect my precious clit from the vibrator in his hand.
Doctor Smith told me there was no need to feel ashamed, this was all part of the exam, and the walls were soundproof. He let me cool down and noted the time when I could feel sensation again. I told him overstimulating my clit was my secret weapon to winning the challenge. I really felt bad when I gushed all over his gloves when he made me cum two times in a row massaging my G-spot with a wand deep inside me.
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Julio delivered me disheveled and waddling to Mrs. Montenegro on the staff dorm floor. That tall bitch was ICE, dressed in a high collared, long sleeved, full length dress and high heels. She even carried a switch! Her long black hair was pulled back so tight I wondered if she could blink her hard dark eyes. She looked down at me disapprovingly while Julio explained I was just here for a couple weeks. Julio insisted I was a good girl.
"Maria, I know you belong here," he turned to me pleadingly, "Promise me you will follow the rules! No hanky-panky, no men. Otherwise you won't be able to stay here and you will not be able to do the challenge."
I nodded. I could play along. Heck, my kitty already had a workout and needed to cool off for a few days.
The floor was divided in half with large rooms on either side. One one side was a common bedroom with six twin beds with small nightstands in between. It really was like living in a convent. The other side had the showers and dressing room where we could hang our restaurant dress or any dresses we had. The rest was Mrs. Montenegro's room and and office.
After assigning me to a bed, the Ice Bitch sniffed me haughtily and declared I was reeking and informed me good girls don't masturbate or have sex before marriage. (Since never, I thought.) She ordered me to leave my bag on my bed, take a shower and meet her in the dressing room. The shower felt good and I met her in the dressing room wrapped in a nice long towel, carrying my clothes. She sized me up and handed me one of those big white puffy blouses, a long skirt, a pair of black knee highs and black flats. Before I could put my waitress uniform on, the bitch had me run to my bags for a fresh bra and panty set.
"I don't want your filthy undergarments touching our uniform. We run a respectable establishment," she haughtily informed me. (Fuck her, I was going commando when she wasn't looking.) The blouse neckline was almost up to my throat. I expected something off the shoulder, to show the girls for tips. I asked Mrs. Montenegro if she had something more revealing. She slapped her switch in her hand so hard I jumped.
"Only good girls work in our restaurant! Families bring their children in for birthdays. Only putas stick out their tetas to any man. Julio said you were a good girl, but I already have my doubts."
Jeez, I was just asking. I clipped on my name tag and went downstairs.
Once I got to the restaurant, I was in my familiar environment. There were only five waitresses, including me. I met the cook and manager, hard at work in the kitchen. I shadowed one of the waitresses, Yolanda, a local girl, who was bigger than me but less curvy. She helped me through the menu, taking orders and the layout. It was almost like working at one of those knock-off chains back in the States. I felt bad I couldn't wait by myself, so I helped the other girls as best I could, bussing their tables for them.
We were so busy, barely keeping up with the tourists and businessmen, but no locals. I asked Yolanda what happened to the sixth girl and she shook her head disgusted, "She decided she didn't want to be a good girl anymore." She glared at me, "Don't be like her."
