A Lost Bet Ch. 04
Keywords: 04, Ch., Bet, Lost, A,
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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 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 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.
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Keywords: 04, Ch., Bet, Lost, A,