A Lost Bet Ch. 04

Nis 15, 2024 // By:analsex // No Comment

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As I slept that night, I dreamt vivid dreams…sexual dreams. The next morning, I was able to remember one of the dreams that I had but I didn’t tell Frank or Tom. I kept it to myself because I wanted to understand what it meant. I’d dreamt that I was walking down the street when I got close to the entrance of a park. It was me in my male clothes. As I got closer to the entrance I heard a voice behind me. I couldn’t understand what it was saying but as I turned to look, I saw someone start to run after me.

As I started to run forward, I saw another figure start running towards me from in front of me. In order to get away, I turned into the park to try and get away. As I ran, the hedges started to grow taller and taller until they stretched far above my head. They were too thick to run through, so I twisted and turned along the path trying to get away. I ran full speed, missing some corners and crashing into hedges as I tried to escape from the voices of my pursuers. With each crash, my clothing became torn, and as some parts of what I figured was a maze got narrower, or were overgrown, I found myself losing some of my clothes entirely.

Finally, I entered the center of the maze but I felt a breeze all over my body. I looked down and realized that I was completely naked. I’d even managed to lose my shoes in the process of running away. I staggered towards what I believed to be a bench to catch my breath, but when I sat down, I fell straight through. It was as though the rabbit hole from Alice in Wonderland had swallowed me up. I slid down the hole faster and faster until I fell out onto a pile of pillows. I looked up, dazed and confused, but as I gathered my bearings I saw I was in a bedroom. I stumbled to my feet and looked around and there on the bed was a set of clothes that I could put on. The closer I got to the bed, the more the clothes looked like the very ones that Alice had worn in the story. I picked up the clothes and heard voices from outside the room…some in the hallway, others echoing down the tunnel through which I’d just fallen. I started rushing to get dressed in order to be able to make a partially decent escape…but I saw no door. Then, in the corner I saw nothing but a smile…the hallmark of the Cheshire Cat. “Now,” he told me “it’s time to find out just where the rabbit hole goes.”

I started awake. “Jo, baby…you okay?” Frank roused from his slumber and reached for me. I was sitting up, breathing hard from the experience of the dream.

“It was nothing. Just a dream.”

“Okay. If you say so.” He rolled over to look at the clock. “It’s about time to get up anyway. I must have been more tired than I thought.”

As I gathered the covers around me, I felt fresh cum leaking from my ass. Frank saw me squirm and said “I guess we must have gone another couple of rounds in our sleep.” He winked at me and made his way to the shower. While he was in the bathroom, I lay there contemplating my dream and figuring that the only meaning was that I was willingly ready to explore further dressing as a woman and whatever came with it. I had feelings of anxiousness and nervousness as I adapted to my new role, but I asked myself “how bad could it be? Last night wasn’t that bad. It was actually kind of nice.” I smiled as I thought about Frank’s seduction of me. It really had been an interesting experience.

With those thoughts and feelings in mind, I made my way out of his bed and back towards my room.

“Hey Jo,” Tom called out from the living room. “You guys sounded like you were having a REALLY good time last night.” He laughed. “Well, today, you’re with me. I laid out the outfit I want you to wear. I was going to wait for you, but it started getting so late that I figured you wouldn’t mind.”

“No problem Tom. Let me get cleaned up, get something to eat, then you can tell me what you’ve got planned.”

I turned into my room and started to gather up what I needed for the bathroom. I saw the outfit Tom had laid out for me. It was a black leather miniskirt with matching jacket, royal blue corset with matching thong panties, black thigh-hi stockings, and knee hi boots with a stiletto heel.

“Tom,” I asked, “where exactly are we going today?”

“Well, you’re going to be my arm candy while I do some gambling. It always helps to have a sexy lady on your arm when you’re at the tables.”

“Okay.” I didn’t say anything else. I simply went into the bathroom and started getting cleaned up. After a few minutes, I heard Tom and Frank’s muffled voices through the door…

“Frank, whatever you did last night really mellowed Jo out. What did you do?”

“Nothing big. Just treated Jo like the lady we knew he could be. I think she’ll be much easier to handle throughout the rest of the week.”

“Cool. Hey, check out this show that’s taking place at the casino tonight. You think we should go?”

I didn’t hear anything for a minute, then finally Frank responded “oh definitely. That party will be worth the trip. I’ll tell uşak escort you what. You guys enjoy your day, then I’ll meet you at the casino around 5 this afternoon, a little before the show.”

I was curious as to what party they were talking about, but I didn’t have time to worry about it since I needed to get dressed. With that, I jumped in the shower and started my routine of showering, shaving, and putting on some light makeup. After I finished up in the bathroom, I went back to my bedroom to finish getting dressed. Once I was done, I stepped out into the hallway.

“Tom, do I look alright?”

“Jo, you look fantastic.” Tom was looking rather dapper in a pair of slacks, a short-sleeved sweater, with his leather coat draped over his arm.

“Are you sure we’ll be warm enough? I mean, we’re surrounded by snow?”

“Don’t worry. Once you get into the car, you’ll be fine. The casinos will be warm enough and we’ll be there for the afternoon. Frank will meet us there for dinner and a show later on this evening.” Frank then tossed me something. “Last thing Jo. Put this in.”

I caught it and looked at it. It was a large butt plug. “Umm. I don’t know if this is going to fit.”

“Come here,” commanded Tom. Slowly, I walked towards him. As I reached him, he put his coat on the chair then told me to “bend over.” I leaned over the table with my ass in the air as Tom started lubing up the plug. He pulled my thong to the side, then slowly and gently started filling my ass with the butt plug. I moaned as he pushed it in. Finally, when it was all in, I noticed that my breathing was a little ragged. “Don’t worry Jo. You’ll get used to it. I just wanted you to wear it because it will give you a little more sway to your walk.” As I stood up, I felt incredibly full. And as I walked towards the door, I noticed my hips swaying a little bit more as I tried to accommodate the plug in my ass.

Tom opened the door for me, and as I sat down in the truck, I really felt the pressure from the plug. I squirmed. “You doing okay over there?” Tom asked as he slid in the driver’s side. “Yeah, just adjusting. Don’t go over any bumps, okay?” I joked. Tom laughed and pulled off. We engaged in small talk all the way to the casino. He asked what happened last night and I gave him a brief description of the massage.

“How did you feel?”

“I guess I enjoyed it. I still feel a little funny, but last night was probably the most relaxing time that I’ve had with you guys so far.”

“Well, that’s good to hear. Hopefully you’ll enjoy today too.”

Once we got to the casino, we parked in the underground garage. “What are you going to do first?” I asked.

“I figure we’ll start with roulette, then maybe play some blackjack. We’ll see how things go from there. But first,” Tom said as he started to unzip his pants, “how about a little blowjob to take the edge off?”

“Tom, somebody might see.” I started to panic and backed up against the door as my eyes darted from side to side.

“No, they won’t. Trust me, nobody’s looking for anything down here. And even if they do see, it’s not like they haven’t seen it before.”

“What happened to not making me do anything out in public?” I asked, imploring him with my eyes to forego the blowjob.

“This…this is not public. I could have asked you to follow me into a restroom in the casino. I could still try to fuck you in the elevator. I could take you outside, find an alley in the cold snow and make you give me a blowjob there. I am ASKING you for one here in the privacy of my ride. I’m only going to ask the question one more time: Jo, please give me a blowjob before we go into the casino.” Tom looked serious, but I didn’t think he would hurt me if I refused.

“I…I can’t. I’m too nervous. I’m sorry,” I said as I put my head down and looked away. “Please don’t be mad at me. It’s just that…the cabin was one thing. This is another. I’m having a hard enough time knowing that I’m about to be in a public place dressed as a woman with a huge butt plug up my ass. Don’t you think that’s enough for me to have to do?”

“You’re right Jo. No problem.” And he zipped up his pants. “Let’s go.” He didn’t look happy, but he didn’t look pissed either. I really couldn’t get a good read on what he was feeling.

“I’m sorry Tom. Look, I promise I’ll make it up to you once we get back to the cabin. I promise,” and I smiled at him, my eyes begging for forgiveness.

“Come on Jo,” Tom said as he opened the door. “Don’t even worry about later. For now, just be a sexy lady on my arm.” He offered his arm to me as he walked me through the garage and into the elevator. He didn’t say much to me as we walked but I tried to dismiss it and focus only on being as feminine as possible. I figured that the less I talked, the less likely I was to be read as a man.

I was so focused that I missed Tom’s comments.

“Jo…Jo…listen to me. I was going to let you off the hook, but I think you should know that muglalisahidi.com your refusal in the garage will have repercussions later on.”

“Like what?” I asked hesitantly.

“I’ll start with this,” Tom said as he reached into his pocket. All of a sudden, I felt intense pressure in my ass as the butt plug started vibrating and pulsing.

“Oh…n-n-n-no…turn it off…please turn it off…” I stuttered and stammered as I tried to maintain my composure. “It’s too intense.”

“If you’d only done like I asked, you could have just enjoyed the plug,” said Tom. “Since you still had to resist, you left me no choice. Well, that’s not really true. I’m going to enjoy watching you squirm for the rest of the day, and that’s a choice that…doesn’t really bother me at all. You?” He smirked as he waited for my response. I was speechless as I rode the sensations and tried to stay ladylike. “Good. Glad to see you’re not bothered. And you will make it up to me later. I guarantee it.”

We walked to the main casino floor. Or perhaps Tom walked while I stumbled along beside him trying not to fall over due to the random sensations sent through my nether regions. Over the next few hours, we stopped at the blackjack tables, roulette tables, craps tables, and finally, the poker tables. Tom only let me sit down at the blackjack and poker tables. Honestly, I wasn’t sure whether I was better off sitting or standing, because when I sat down, the plug got shoved further up my rear where it continued to twitch and vibrate and put pressure on my prostate. But when I was standing, I felt like me knees were going to buckle. There was no escaping its’ relentless assault on my ass. I was only minimally aware of the occasional soft moan escaping my lips, but Tom paid me no mind. It was some of the looks that I got from others nearby that let me know that I’d actually made a sound. I saw some of the quizzical looks on their faces, but tried to ignore them, and they ignored me as they focused on their gambling. But I know that every now and again, while Tom and I were at the roulette and craps tables and the crowds were pressed together, I felt a hand pinch my ass. I knew it wasn’t Tom because I could see both of his, but I couldn’t turn around to see who might have done it. It didn’t matter anyway, because I would soon be focusing on the vibrating butt plug again, alternately praying that the batteries would die so I could get a break and hoping it would continue so that I could cum. Neither one happened.

A few years later (okay, actually just a few hours later), we met up with Frank in the lobby of the casino.

“How’d you guys do?” Frank asked.

“I’m up about $700, so I’m pretty happy,” said Tom. “Jo is feeling something else for an entirely different reason.”

“Oh no. You didn’t have to use it on her, did you Tom?” Frank asked as he shook his head.

“Yep. She refused a simple request when we got here, and I had to remind her that even minor innocuous requests should not be refused.” Tom look disappointed as he continued on to say, “I thought that after last night with you, she’d be easier to work with, but since that doesn’t seem to be the case, I guess we’re running out of options.”

“What…what are you guys talking about?” I stammered through my sensual onslaught.

Frank and Tom both looked at me, then each one took an arm and they led me to a hallway leading towards the ballrooms. They said nothing while we walked and I continued to look from one to the other for a response. Once we were in front of one the ballroom doors, they stopped.

“Jo,” Frank said. “We’re about to go into a different kind of show. The show is called Erotique, and there’s a few things you ought to know. First of all, we’ll probably be a few of only a small group of Black folks in the show. So that’s going to draw attention to you regardless of anything else. Secondly, had you only obeyed, we might have let you enjoy the show in a different capacity. But since you continue to be stubborn, even after we had such a great night last night, then you’re going to have to learn a few things. One is how to obey. The second is how to give pleasure on a moment’s notice. The third is to surrender. I hate to say it, but in this show, the more you fight, the harder your life is going to be. I know I said back at the cabin that I don’t mind a little fight because I like the challenge. But here, and know that I’m telling you this because I like you, fighting back, resisting is bad. Like on Star Trek, with the Borg… ‘resistance is futile.'” Then he nodded at Tom who grabbed my wrists, turned me around and forced me to face the wall. As I started to stutter out a question, Frank produced a ball gag, seemingly from out nowhere and forced it into my mouth. “To keep the protests to a minimum,” he said. I started having flashbacks to the first night the guys had their way with me and I started feeling nervous. I tried to squeeze a question out around the gag, but succeeded in making nothing more than a few mumbling sounds. Tom slid my jacket off my shoulders and arms, then tied my wrists together behind me.

“Are you ready Frank?”

“Yep. Let’s go.” Then Frank opened the door and guided me through the door in front of him. We took a couple of steps down a short hallway, then knocked on another door. A slat slid open and an eye looked us all up and down, then slowly pulled the larger door open. As we entered into the darkened room, my eyes started to adjust and I took in the scene around us. It was nothing like I’d ever seen before. Everywhere I looked, I saw people in bondage…people having sex…people being teased and tortured… I turned and looked at Frank and Tom with fear in my eyes because I knew what they were thinking. My eyes pleaded with them to walk us out of there. I pressed myself against Tom trying to coax forgiveness out of him by offering myself to him, but he just turned to Frank and said “I think our little Jo is feeling kind of frisky. Where should we start?” Either he’d misinterpreted my body signals, or he was just choosing to ignore my desire to escape.

Frank took my arm and started leading me through the room towards a corner that seemed to have an array of spanking mechanisms. As we walked, I saw people turning to look at us making our way through the room. I looked around and was able to spot only one or two other Black faces and I knew that Frank’s words were true. I was going to be an attraction.

When we arrived at the corner, Tom unzipped my skirt, pulling it to the floor and I heard a few whispers and giggles as the crowd noticed that, not only did I have a large, vibrating butt plug in my ass, but I was also a man. “Mmm… I’d like to get a piece of that ass,” I heard someone say, but I had no idea who it was. More comments followed as Frank and Tom pulled me towards one of the devices. There was a woman standing there, and she almost looked like a saleswoman.

“I see you’ve got a ‘bad girl’ there. Does she need a proper spanking?” She asked with a twinkle in her eye. Her name tag said “Lisa,” and she and the guys started to talk as if I wasn’t even there.

“Lisa, our girl Jo just refuses to act right. We figured that we’ll have her make the rounds of some of the activities here until she gets her attitude right. What can you tell us about what we’ve got here?” Frank asked her as he pointed at different set-ups.

“Well, we’ve got various hand-held spanking instruments that you’re welcome to use, and buy if you’d like to take them home with you. We’ve got paddles, whips, rulers, breadboards, belts…and a couple of other things that I KNOW you’ll enjoy. If you’d like to try some of them out, why don’t you get…Jo, is it?…set up, or tied down over here.” She pointed to what looked like a padded counter. Frank and Tom dragged me over to it as I tried to resist being moved over there. But there was nothing I could do. The pushed me over the padded edge of the counter and spread my feet apart. Tom secured my feet to each leg of the counter while Tom grabbed a chain that was hanging down and tied my wrists to it. It was a position I’d been in before, but this time I felt much more vulnerable. I could almost feel the tears start to form in my eyes.

“Don’t cry yet Jo,” said Tom. “We haven’t even started yet.”

Then Lisa noticed the butt plug. “Did you want to take out her plug, or leave it in?”

“Leave it,” both Frank and Tom said in unison which drew a round of laughs from the gallery.

I continued to moan and struggle in my bonds but there was nothing I could do to free myself. As I looked ahead, I saw Lisa moving a mirror in front of me so I could see exactly what they were about to do to me. “Such a deserving girl. I’m sure that whatever you’re about to receive, you had coming to you.” Then she returned to Frank and Tom and discussed the merits of each spanking instrument.

I heard her say “the smaller instruments give a more focused sensation and tend to leave marks. See?” Then I jumped as she slapped my ass with a ruler. Again and again, harder and harder…she just kept spanking my ass and legs. “You’ve got to be careful though, because if you hit too hard with the smaller ones, the likelihood that you’ll break the skin goes up. You want to try and find a balance. The larger tools, you want to be more careful for a different reason. While they do produce an overall stinging sensation in the spank-ee, you don’t want to hit too hard. I’ve heard of people actually causing internal injuries from spanking someone too hard with one of the larger paddles or breadboards.” She then proceeded to demonstrate what a good level of force could be. “Anything that strong or less should get you maximum reaction without feeling like you’re not doing your girl too much damage. Here Tom, give it a try.” I looked on in horror as Tom wound up and proceeded to paddle my ass. With each stroke, I squealed and moaned. After about 5 strokes, Tom backed away and Frank came from the other side with one of the breadboards. The larger paddles left my entire ass tingling and each stroke forced the butt plug further and further in. I was losing myself in the pain and humiliation.

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