As I knelt next to Master, thinking of the last hour… my first hour in the BDSM world… I struggled to focus. I never considered myself a prude, nor did I think of myself as overly vanilla in regard to my sexuality, but the experiences of the last hour revealed that my experiences to this point were, indeed, rather benign.
My thoughts were repeatedly interrupted by people fondling my breasts as they came to speak with Master. Some of the men would expose their cocks, which Master clearly expected me to suck while they talked. This continued for an hour or so. During this time, Becca spent her time on her knees between Master’s legs, his cock in her mouth the entire time. While some of the cocks I sucked were thick and stiff, most of them were surprisingly inadequate compared to Master's gorgeous cock. Watching Becca, I found myself getting a little jealous.
After another hour or so of sucking the cocks of the men coming to chat, Master gently pushed Becca back before standing and returning his cock inside his pants. He grabbed the leashes attached to our collars and led Becca and me down from the platform and through the convention hall. On the way. Master pulled a gentleman aside and whispered something in his ear. The gentleman nodded and walked away. As Master led us through the hall, I glanced back at the gentleman Master had spoken with, only to watch him pick up a microphone and announce that the wagering room was about to open. I glanced over at Becca, who surprisingly didn’t seem confused, at least not as confused as I was.
My confusion increased as Master led us into a room in the rear of the convention hall, with a sign stating “Wagering Room” hanging above the door. Inside the room were tables with a plethora of sex toys, ranging from clamps and chains to dildos and vibrators, as well as floggers and strapons. There was also a variety of cuffs and other restraint devices. There were also two large wooden X objects and what looked like two sets of stocks you would see in Colonial Williamsburg. At the back of the room was another throne-like chair, with two large pet crates on either side.
Master led me into the crate on the left of the chair and Becca to the crate on the right, locking us in with small padlocks. I watched as people started to fill the room, mostly men, some leading women on leashes like Master led Becca and me. The many casually inspected the sex toys and the apparatuses before finding a place to stand around the outside of the room. Master then walked to the center of the room and stated that those in attendance should make their wagers and announced that the games would now begin.
I watched as many of the men wrote on index cards and placed them in a large glass bowl. After all the cards were collected, Master reached in and pulled one out. He read it aloud: “St. Andrew’s Cross, vibrators, and weighted nipple clamps.”
Master smiled and nodded, then snapped his fingers. Two very muscular men appeared seemingly out of nowhere, and they unlocked mine and Becca’s crates and led us each to one of the X-shaped devices in the center of the room. They secured our hands and wrists to the device, then stepped away. Master then approached and told us that the game was simple. The last one to orgasm wins the point for this round. He then attached the weighted clamps to Becca’s nipples, then another pair to mine. I groaned through the ring gag as the teeth of the clamps dug into my hard, sensitive nipples. Master then inserted identical vibrators into our pussies, stepped back, and pressed a button on a small remote control. Suddenly, the vibrator came to life in my pussy, and I could tell from Becca’s reaction that hers did as well.
The competition was over before it started, as I orgasmed within a few minutes. I wasn’t one prone to masturbating with toys, preferring to fondle myself with my fingers. So when the vibrations hit, my whole body convulsed with ecstasy. But Master decided to leave the vibrator on until Becca also orgasmed. As my body continued to shudder, I noticed that Becca, while clearly feeling the effects of the vibrator inside her, did not appear close to her orgasm. The minutes felt like hours, and I realized my body was starting to shudder again. Another moment passed before I again groaned with another orgasm, much to the pleasure of those gathered.
Becca finally… mercifully… reached her own orgasm a moment later, at which time Master pressed the button on the remote and turned off the vibrators. On a whiteboard along the wall, he gave Becca two points, explaining that was the result of my orgasming twice before she did. Master then told the muscular men to remove the vibrators, which they did, and then handed them to Master. Smiling, he slid Becca’s vibrator through my ring gag and fed mine to Becca, explaining that toys must be cleaned after use. I could taste Becca on the vibrator, finding her juices to be quite delicious, and hoped that Becca was enjoying my remnant as well.
While still secured to the crosses, Master reached into the bowl once more and pulled out another card. “Fill the cup, kneeling, wrists cuffed to ankles,” Master said. Snapping his fingers, the muscular man released Becca and me from the crosses, then set us on the floor on our knees. They cuffed our wrists to our ankles, and then Master came over and removed the ring gag from my mouth, explaining that this contest needed an even playing field. He then placed champagne flutes in front of us and explained that the first one to fill their flute with cum would earn one point for every guy it took to fill their flute. Second place would receive no points. Master then told the men in the room to form two lines and to pull out their cocks. The men were told they could hold our heads for balance, but they could not thrust.
Master then told the men to begin, and one by one Becca and I began our game of blowjobs. Most of the men came quickly and were kind enough to lift the flutes to our mouths so we could spit their cum out. After four guys, my flute was half full, which I thought was a good pace until I noticed that Becca’s flute was almost two-thirds full. Groaning in frustration, I sucked the next few guys harder and harder, hoping to suck out as much cum as I could. But it was fruitless, as Becca filled her flute after only six guys, giving her eight more points.
Leaving us on our knees, wrists and ankles still cuffed, Master reached into the bowl a third time and pulled out another piece of paper. Before reading, he announced that this would be the final competition for the night and that the odds would be doubled. Up until this point, I hadn’t noticed that many in the room were betting on Becca and me, and from the looks of a few faces, I was clearly losing money for them. Before I could further consider the consequences of my poor performance thus far, Master spoke once more. He announced that the final competition would be a “suck or fuck” challenge. He explained that one of us would be sucking dildos of increasing size while the other would be fucking dildos of equally increasing size. The last one to either gag or orgasm would win, with the victor receiving 15 points, making this a winner-take-all event.
Since Becca was in the lead, she was afforded the opportunity to choose to either suck or fuck the dildos. She chose to suck. I tried not to react, but in my heart I knew I was going to lose, as the largest toy I’d ever used was only 8” long, and that made me cum within minutes. I couldn’t imagine being able to take anything larger.
As I watched two trays of dildos being brought out, the two men from earlier uncuffed Becca and me. A tray of dildos was placed before each of us, and Master explained that we were to spend one minute with each dildo, starting with the 6” ones and working up from there. As the crowd gathered and began to cheer, Master leaned in close to me and whispered that he was betting on me to win. His words gave my spirit a slight lift, but also caused my nerves to explode. But before I could think more about it, a bell rang for us to begin.
I watched Becca grab her first dildo and begin to suck on it as I picked up mine and slid it into my sex. I was already soaked from the evening's activities, so it slid in easily, and I proceeded to pump it in and out, surprised that it was having little effect on me. After a minute, the bell rang and we switched to the 7” dildos. Again, Becca clearly was having no issues sucking on her dildo, but to my surprise, I was having little reaction to the one in my pussy.
The bell rang again, and I took a deep breath, knowing that the 8” dildo would likely be my undoing. I slid it in, and while I felt pressure for the first time, it was not enough to trigger my orgasm. I looked over at Becca and noticed a slight grimace on her face, as if she were struggling a little bit. For the first time, I felt I may have a chance to win.
Again, the bell rang, and I filled my pussy with a 9” dildo while Becca struggled even more to swallow the same. The seconds passed slowly, as I could feel my orgasm starting to build. But to my shock, I heard Becca start to gag as she pulled the 9” dildo from her mouth. The crowd reacted with a similar level of surprise, as I’m sure most, if not all, expected Becca to win.
Master walked up and waved his arms to quiet the crowd. He had Becca and me stand, then raised my arm to declare me the winner. He then stated that whoever had won the most money during the evening would be given a voucher that could be exchanged for a one-hour session with either Becca or me on the last night of the convention. Master also announced that whoever lost the most money would receive a voucher for a 15-minute pegging session with either Becca or me. I wasn’t expecting either of those and looked at Master with a mix of surprise and shock. Sensing my concern, Master simply put his finger on my lips, then instructed Becca to return the ring gag to my mouth. He then signaled the two men from earlier to return us to our crates.
As people started to exit the room, an announcement was made that the convention was now closed for the evening. Master made a point to chat with as many as he could as they left, while I watched from my crate. When the last person had left, Master came over and thanked Becca and me for being such good pets and gushed at how proud and impressed he was with us. He then reminded us both that our time was our own until the next evening unless he called on us prior to that. He then instructed the two men to return us to our rooms. Admittedly, I was ready to go take a shower and collapse on the bed in my room. As I waited to be released from my crate, I noticed two luggage carts being wheeled into the hall, directly towards us. To my surprise, the two men lifted our crates onto the luggage carts, respectively, and started wheeling us out of the convention center. As we left, Master instructed the men once again to ensure we got back to our rooms safely.
The ride back to my room was thankfully uneventful. Few people were lingering in the lobby, and most of those were drunk as they left the lounge. The elevator was empty, and no one was in the hallway as Master's helper unlocked my door and wheeled me inside. He unlocked the crate and helped me out. He then introduced himself as Marcus and shared with me that he was going to be my bodyguard for the remainder of the convention. He gave me a card with his cell phone number on it and told me that I should call him if I needed his assistance in any way. I was confused by that but thanked him, and he left.
I went into the bathroom and looked at my reflection in the mirror. I could not believe that the woman staring back at me, the woman caked in dried cum and sweat, was me. I took a shower, too exhausted to do anything other than clean myself, then fell down on my bed, dreaming of the night's events and wondering what was in store for the rest of the week.
