A Lost Bet Ch. 05

"Hot damn Jo! You look amazing!" Frank had a look of awe on his face as I turned around to give him the full effect.

"What? What?" Tom called out from the shower.

"Don't worry about it," Frank responded. "You'll see when you're done." Frank returned to memorizing every curve that was hinted at by my outfit. I could have sworn I saw him licking his lips.

"You look pretty dapper yourself," I said to him to try and get his attention focused anywhere else. I was afraid that he might decide that he wanted to have me as an appetizer...which might not have been too bad, but I still wanted to maintain some level of decorum.

"Thanks Jo," he replied. "Can I get you anything while we're waiting on Tom?"

"Just water, thanks. Now what you can do is tell me about the people we're supposed to be eating with. I know you said that you and Tom met them during 'my show,' the other day. But who are they? What's the plan for tonight?"

"Well, it's a group of about 3-4 people that we're planning to meet at the restaurant. It's supposed to be 2 couples, males and females. The plan is just to enjoy a night out on the town and to meet some new people. Whether or not anything physical happens...we'll just have to wait and see. But I do know that the women want to get to know you. Back at the show, they were real curious about what your experiences had been like."

I nodded as I thought about what I might tell them. As I sat down to wait, I watched Frank's eyes follow my every move. I gave him a little show when I crossed my legs and I know I saw the front of his pants start to bulge. "Everything okay Frank?" I asked sweetly.

"Hunh? Oh, I'm fine. You know...just...taking in the sights," he said with a smile. "And I've gotta say, you are a helluva sight."

Tom finally came out from the back room to join us. "So what was all the commotion ab...?" He stopped dead in his tracks as he gave me the once over...then the double-take. "Jeez, I think I'm having a heart attack." Frank and I laughed. "Seriously, Jo...you look amazing."

"Thank you Tom." I smiled at him.

"Frank, do you notice that something seems different about Jo? There's something...I can't quite put my finger on it..."

"You're right Tom," Frank said. "I had the same feeling but I also wasn't too sure about what it might be." They looked at each other, then looked at me as if they were waiting for an answer. I sat for a minute soaking up the ambience and letting their minds work before responding.

"Guys, it's nothing physical. I didn't do anything different. The clothes are the same ones we saw in the store. The wig is the same one I've been wearing for the last few days. The amount of makeup I'm wearing hasn't changed, still just a little lip gloss." I paused before continuing, "The only thing that's different is my attitude." I looked each of them in the eye for a moment, trying to see if they understood. I decided to tell them a little more.

"Look, while we were talking this morning, you gave me a few things to think about. And some of it represented the same 'struggles' we've been having since you guys started me down this path. Don't get me wrong, once we get back to civilization, my male stuff is coming back. There will still be basketball and football and poker and all the things that generally like to do when we're hanging out. But what I've finally come to grips with is the idea that, in a situation like this, where I'm under someone else's control, I'm free to do whatever I want and be whoever I want. Granted, it's not like I'm going to go out and be some tramp or floozy. That's just not my style. But I can get into being a lady, even one who occasionally acts a little slutty for the guys that I'm with, which is basically you two. I know that there are still things we might explore, but we've already done a lot. I've experienced a lot as your 'girl,' and it's been an eye-opener. A little uncomfortable, sometimes more than others. But I'm accepting that I've still done most of these things willingly, even under the threat of punishment, it was still my choice. And there have been parts that I've enjoyed. So, I say let's see where this goes. For this trip, I'm your lady and I expect to be treated like one. Of course, I think we're all about to see just what that means, but it ought to be an interesting experience. I guess you could say that I've gone over to 'the soft side.'"

The looks on their faces as I'd been talking changed from curiosity to confusion to understanding. They knew that I'd finally stopped resisting and that I was ready to relax and have fun and be open to whatever it is they still wanted to show me. I knew them well enough to know that they would still treat me with a level of respect, but I also knew that they still had some kinky stuff up their sleeves that they were waiting to roll out.

"Are you ready?" I asked them.

"Yep," replied Tom. "It's about that time."

"On so many levels," Frank added. "Let's go." Tom simply nodded as he helped me put on my outer coat. As we walked to the truck, Frank was even gentlemanly enough to open the door for me and hold my hand as he helped me in. Before long, we were cruising down the road on our way into town to meet our companions for the evening. Along the way, we recounted our day's exploits on the mountain and laughed at various jokes. We also talked about future get-togethers...where we might go and what we might do. We arrived at the restaurant almost too soon.

As soon as we walked in, Frank waved at a couple in the waiting area. "Hey Gina, Mark. Good to see you again. Have you been waiting long?"

"No, not at all," Gina replied. "You must be Jo," she said as she turned to look at me.

"I am. It's nice to meet you," I replied with an outstretched hand.

"Oh come, come," she said as she pulled me into one of those hugs that girls tend to give each other. "I've heard so much about you that I feel like we're already friends." Her smile was mischievous, but sincere. "You look delectable in that outfit."

I smiled and complemented her back, "so do you. That dress looks fantastic on you." She gave a little twirl in her burgundy cocktail dress. "You're not too cold, are you?" I winked as she glanced down and saw her nipples pointing through the dress. She laughed.

"Not really. Besides, I've got Mark to warm me up." In the midst of me getting to know Gina, Mark had gone on to greet Frank and Tom. As I looked at him, I thought his face was kind of familiar and I realized that he must have been at the show earlier that week.

"Are the others here?" asked Tom.

"Yep. Elise and Alex are already seated," Mark informed us. "They're waiting on us."

Frank, Tom, and I followed Gina and Mark to a private booth in the back of the restaurant. It was obvious that the restaurant was designed to create as much privacy in a public place as possible. As I was introduced to Elise and Alex (apparently both of them had been at the show with Mark), I slid into the booth between Frank and Tom. Everyone chit-chatted as we looked over the menus and tried to figure out what we wanted to order. The waiters brought bread and water and took our drink orders while we continued to get to know each other.

"So, Jo," Elise started in, "I thought your performance at the show the other day was very memorable. I'd never seen a transvestite live before and you looked like you were enjoying yourself." I felt my face get hot and was thankful that my brown skin hid what would have been a raging blush. "I've been dying to know how long you've been dressing and what it feels like for you."

"Oh definitely," chimed in Gina. "I really want to know the full story because you really do look amazing and feminine and you seem to really enjoy being with Frank and Tom."

"Well...would you believe that this whole 'situation' started with a bet about 6 months ago?"

"No," Gina gasped. "Six months? That's it?"

"It's true," Frank said. "Tom, Jo, and I were playing poker and Jo lost a bet. He had to do whatever we told him to do and we asked him to dress like a girl."

"So, you had him dress like a girl. Did he look as good as he does now?" Mark asked.

"Did you do anything else that day? That's the real question," Alex chimed in.

"Well, we shouldn't kiss and tell..." said Tom, "but since we did more than kiss, I guess it's okay." Everyone laughed. "Once we got Jo dressed, it didn't take long before we had him serving us drinks and food...and after a few minor disagreements regarding point of view, Jo came around."

"Oh really?" asked Elise. "How so?"

Frank took this part of the response. "Well, he came over the couch after we tied him up and popped that cherry. He actually sucked his first cock that night...at least as far as we know."

"That was my first, thank you very much." The group laughed at my playfully indignant response. "The guys were my firsts for a lot of things. And I'll be honest, that first night left me pretty pissed off."

"I'll bet. It's just like a couple of guys to take advantage of a vulnerable young lady," Elise laughed as she responded with partial sympathy and scolded the guys. "Seriously though, you must have had a rough time."

"I don't know Elise," Gina replied. "After the first couple thrusts, I'd have imagined that Jo had a pretty smooth time." The laughter flowed freely at this point. The waiter returned with our meals so we put the conversation on hold while he was there. After he left, we started right back in.

"I'll be honest, it took me a few months after that night to even be willing to risk going out with those two again. My issue was that they told me that, now that they'd had me once, they were going to make it their goal to have me again and again whenever we were in private. That kind of scared me."

"So how did this trip come about?" asked Alex.

"It really happened because Jo made a mistake," said Tom. "Jo finally came by to hang out with us again for the superbowl. In the midst of the excitement of the game, he made a bet with Frank and Frank won...again. The bet consisted of this trip and Jo's obedience. And we have to give it to him, Jo has been a total sport going along with the bet. We've actually been talking a lot over the last few days and Jo has been coming to grips with 'her' position."

"Is that so?" asked Mark. I thought I caught a gleam in his eye.

"Within reason," I quickly added. "Yes, I've done some things over the last few days that are WAY out of the norm for me, but that's because Frank and Tom have generally treated me with respect and not made any demands that were inappropriate for the situation."

"So," Elise asked, "you were willing to do the demonstration at the sex show because everyone was doing it and it was basically okay?"

"Yes," I responded. "I'm not going to do anything in public that's going to cause me any unnecessary embarrassment and Frank and Tom have respected that. And as long as they continue to respect that, then I guess I'm willing to try most of the things they want to do...in private."

"So, what say we test that theory," Alex challenged.

"What are you thinking Alex?" asked Gina. Elise and Mark also looked curious, but I got the sense that they already had some ideas.

"Frank, if you and Tom are willing, how about we swap partners for the night?"

"What, you want to trade Jo for Elise?" Frank asked.

"No. I want to trade Elise and Gina for Jo...for Mark and myself." Alex said.

Frank and Tom looked at me. "What do you say, Jo? Are you willing?"

To be continued...