A Lost Bet Ch. 07

As I sat there and tried to keep my breathing out of the panic range, I continued reflecting on my options. After the first couple of minutes of alternating between swallowing with my throat and swallowing with my ass, I found a rhythm and pace that worked. But I didn't know how long I was going to be able to hold out because I was really starting to feel full. I had no idea how long Alex and Mark were gone, but I knew that if they didn't come back soon, I'd have to hit the panic button simply because I didn't want to drown. Already, with each turn of sucking on the "straw", I felt water leaking out of the corners of my mouth. Finally, when I didn't think I could take anymore and I felt like I was going to explode and was on the verge of hitting the panic button, I heard someone say "relax Jo...just slow yourself down, and relax." I looked up to see Alex sitting on the stairs, with Mark's frame highlighted by light from upstairs. "You didn't really think we'd leave you in such a precarious position with only a panic button, did you?"

Alex turned and nodded to Mark, then proceeded to come down the stairs and caress my face. I moaned a plea around the water with a tear in my eye and Alex moved close to reassure me. He shut off the water flowing through the penis gag and gave me a chance to swallow the water that had started to leak from my lips. "You were never in any danger Jo. I admit, your reaction was priceless and the desperate look on your face was such a turn-on, but we had our eyes on you the whole time."

"How's she doing?" Mark called down from upstairs.

"She's fine Mark. A little unnerved, but not broken. I think she just got a little taste of how extreme even little things can get." Alex kept petting my head as he talked and I found it incredibly soothing. "Still, I think we ought to move on to something else because I doubt that Frank or Tom would appreciate it if she ended up getting hurt through our games."

Mark moved to shut off the water pumping into my rear while Alex gingerly removed the penis gag and I coughed up a little water.

"Are you okay?" Alex asked.

I nodded, coughed again and squeaked out a "yes, but I REALLY need to go to the bathroom."

Alex and Mark laughed at that, and Mark proceeded to lift me up off the chair and put me over his shoulder. I groaned and felt the water sloshing inside of me. Being on his shoulder only made me have to go to the bathroom more. "Please hurry...I really have to go and I don't know I can hold it in much longer." And with that statement, even as I clenched my cheeks together as tightly as possible, I felt a few drops leaking down my legs. Mark started walking with me towards the bathroom and Alex followed. As soon as we got there, he set me down on the toilet. Thankfully, my penis was already tucked so when I started to pee, it was pointed in the right direction. My ass opened with the barest urging and with an audible splash, I heard the water filling the bowl. I was visibly relieved and Alex and Mark smiled at my apparent relief. While I sat there, Alex undid the collar keeping my head in position and Mark started to unbind my legs. Multiple types of relief started to flow through my body. Every time I thought I was through though, more came out. Alex was kind enough to untie my elbows, but he left my wrists bound together. Finally, after a few minutes, I was through and Alex and Mark helped me to my unsteady feet.

"Here we go," Mark encouraged as they walked me back into the playroom. "We're expecting company in a few minutes." They sat me down on the bed in the room and (finally) untied my wrists.

"Who's coming?" I asked. Mark slid my legs onto the bed and Alex nudged my shoulders down towards the bed.

"Roll over," Alex gently commanded. I complied and the guys proceeded to massage my arms and neck, legs and back. The feel of their strong hands working out the kinks that had developed from being bound in so many different positions almost sent me in to neural overload. I didn't moan...I purred from the feeling and relished the sensations being wrought on my body.

"To answer your question, a couple of ladies that we're familiar with are bringing their new boy-toy by. When we told them about you, they were absolutely insistent about coming by to meet you. I think they have an idea to do to him what Frank and Tom did to you...and they want your assistance." I abruptly looked up at Alex. "Relax and enjoy the massage. After talking with Tom and Frank, we, and they, realize that you've been on the receiving end of a most of these experiences...so to speak. So Mark and I agreed that it would be a good break for you to be on the other side of things for a little while. Are you okay with that?"

I closed my eyes and pondered his words for a minute. I wasn't sure what was expected of me. "Tell me more. I mean, what do these ladies expect me to do?"

"Well," Mark chimed in, "their new boy-toy is...a bit reluctant to try new things. He loves having sex with them, I mean, they're hot and bisexual, so what guy wouldn't love that? But they want more out of him. They want him to understand what it feels like to be patient and accepting of gentle touches and simple caresses. They want him to enjoy the act of surrendering himself to someone else instead of always being in control. They him to understand that by surrendering, he's actually gaining more control. They want him to appreciate the feeling of being penetrated, fucked, to the point of an earth-shattering, body-focused, over-the-top orgasm."

"Basically," Alex interjected, "we told them about how much you've come to enjoy your experience of being a girl...and we know about the feminine type of orgasms you have. They're written all over your face when you're riding someone's cock. I noticed it here. Frank and Tom noticed when they were having sex with you. And everybody saw it at the sex show (I blushed). Just open up and help this guy get a taste of what could be."

I was still a bit nervous. "Am I expected to be some kind of dom or something?"

"Not unless you want to," Mark responded. "We're not exactly sure that the girls have done that with him yet, but if that's what you're comfortable with, then yes. We'll be there to help as well. What do you say?"

"Okay, I'm in," I replied...as if there was ever any doubt. "But before they get here, can I have some clothes?"

We all laughed at that. Alex stopped rubbing my shoulders and neck as he went over to the chest that I had been strapped to earlier. As Mark removed what was left of my earlier outfit, Alex opened the chest and pulled out a pink bustier with matching thong, a pink ruffled skirt, and some matching pink and white skechers tennis shoes. As I put on the outfit, I relished in its soft comfort. The skirt was light and caressed my thighs and rear, and the bustier wasn't heavily boned so I had a lot of flexibility and even some cleavage to show. And the tennis shoes...after wearing heels for so long, I'd forgotten what really comfortable low key shoes might feel like. The overall look was sporty, yet sexy...and Alex pinched my butt as if to remind of how attractive he thought I was. But I could see it in his face. And as I looked at Mark, a similar look was written on his. Quickly, I leaned over to each one and gave them a quick peck and said "when do our guests arrive?"

The ringing of the doorbell answered the question for me. The three of us walked upstairs and headed towards the door to meet our guests. Alex was the first one there and opened the door. "Hey Chantelle, Maria. How are you?"

"We're good thank you. Hey Mark," Chantelle answered with a wave. "And you, you must be Jo. Cute outfit." She reached out to shake my hand and I shook hers back in a decidedly feminine fashion. I couldn't help but check her out with her long black hair and honey-colored skin. The jeans she was wearing clung to her in all the right places, and the red t-shirt she was wearing accented her breasts quite nicely. As I looked down, I saw that she had on matching red boots. It was a casual, yet very sexy outfit.

"Nice to meet you Chantelle, and thanks," I responded. "And you Maria." Maria smiled and shook my hand as well. I thought that she had to be Latina with her soft round face and brown curls. She'd decided to wear a long jean skirt with brown knee high boots and a white cashmere turtleneck. These two ladies were working their outfits.

"This is Charles," Maria introduced the man standing behind them. "Hi," was all he said as we ushered the three of them into the house. He was probably about 5'10" and maybe 170 lbs. His dark brown skin was accented by the grey sweater he was wearing over his jeans and boots. He was handsome, but he looked a little uncomfortable.

"Please, come in and have a seat," Mark offered as Alex took their coats and hung them in the closet. He led them to the living room (which I hadn't seen yet), and we all took seats. I sat on the loveseat next to Alex while Chantelle and Maria made themselves comfortable on the couch. Charles sat down on the big chair and tried to be casual. Mark kept going through the room towards the kitchen. "I've got some wine in here. Jo, can you help me bring out the glasses."

"Sure," I replied as I popped up off the loveseat and went into the kitchen. Mark had already set the glasses on the counter, so I picked up four of them and walked them back into the living room. Mark followed me in with the other two and the bottle of wine. As we set the glasses down, he started to pour and I passed the glasses around. When everybody had settled in and was sipping, he finally took a spot near the fireplace and I settled back into the loveseat.

"Well, we're glad you all decided to come through," Alex said. "Everything been going well?"

"Oh yes," Maria replied. "Chantelle and I have been having a great time together. We still miss you guys though. How long are you in town?"

"Just another couple of days. Then we head back to the city."

"Did Elise and Gina come?" Chantelle asked.

"Yep, they're hanging out Frank and Tom, the guys who came up here with Jo," Alex responded.

"Well, tell them we said 'Hi' and we'll call them later," Chantelle responded. "Now Jo, you've got to tell us how all this came to be. I mean, have you always been a crossdresser or was this something new? Are you bisexual, gay, straight? What's it like for you?"

"Alright, alright," I laughed in response. "Slow down and I'll try to answer all your questions. It all started with a bet..." I started off by relaying the details of my story...how Frank and Tom had basically turned me into their plaything, the things we'd done along the way, and how we'd come to meet Alex, Mark, Gina, and Elise. Chantelle and Maria listened with rapt attention, occasionally taking a sip of wine, laughing at times, and appearing to get aroused at others as they licked their lips at the images of me being skewered and caressed danced in their heads. Finally, I finished telling the facts of my experience and started delving into the other side...the emotional and psychological experiences.

"...It's been a real interesting experience. I never would have imagined that I'd find myself in this situation, let alone find myself enjoying it. But once I started to loosen up and go with the flow, it got to be quite a bit more enjoyable."

"So, now that you're here, what would you consider your sexuality to be?" Chantelle returned to her previous question.

"You know Chantelle, I've been asking myself that same thing. The quickest answer is that I consider myself to be bisexual. But it's not necessarily that simple. The truth is, I think that I'm very much straight. When I'm in my day to day environment, I'm very heterosexual. I love women. I love being with them, talking with them, having sex with them, tasting them, loving them...I just love women. I walk down the street and imagine what it would be like to be with this one or that one. I also engage in very stereotypically male behaviors...I like sports, love technology, appreciate fast cars and motorcycles, and all that stuff." I paused to take a sip of wine and out of the corner of my eye, I noticed Charles listening closely while trying to appear like he wasn't being sucked into my story. "But when I'm dressed as a woman and hanging out with Frank and Tom, or Alex and Mark, I enjoy being treated like a woman. I was really uncomfortable at first because I was worried about being read as a man in a dress. But with Frank and Tom's urging, I started to go with the 'act', for lack of a better word. The more I let myself just relax and be treated like a woman, the more I was able to naturally emulate feminine behaviors, and the more a latent sexiness came out. I felt desirable...but in a different way from when I was in my 'masculine' mode. I saw other guys checking me out, and sure, some of them probably read me as a man, but nobody acted any differently. For the most part, I've been accepted and treated as a woman wherever we've gone. Granted, it's only been to a few places, but it's been good. And sexually, well...I'm not gonna lie. Being on the receiving end took some getting used to. I really struggled with it at first. But as I started to learn to surrender myself to the feelings and not get caught up in who was doing what to whom, I started to feel more pleasure. It's like I was given permission to be vulnerable, to be sexy, to be a woman. I stopped looking at things as 'being fucked by OTHER men' and started looking at it as 'being fucked BY men'. It was, and is, a subtle distinction but it works for me. I'm not necessarily attracted to guys, no more so than before...but when I'm dressed as woman, I can enjoy having sex with them. I just happen to be a woman with a little extra. I don't know...does that make any sense?"

I looked around at my audience and could see Chantelle and Maria nodding their heads. Even Alex and Mark seemed to understand what I was saying. Charles still looked skeptical, but if I understood correctly, he was going to have to get over it...or leave, I suppose.

"Here's another question for you Jo," Maria said. "Have you ever had sex with another woman while dressed as a woman?"

"Not yet I haven't," I replied. "Why, are you offering?" We all laughed.

"Maybe...probably," she responded. "I'm feeling a bit turned on...but don't want to go there just yet. Tell me, what do you think it would be like for you to have sex with a woman while dressed?"

I shrugged and said, "I don't know. I guess it would probably feel more like a lesbian thing to me. For some reason or the other, in my head, there's a real distinction between the male and female roles and the attire associated with each. I mean, if I were with another man who was also dressed as a woman, it would probably feel more like two women together than two men. Maybe it's just that societal double-standard that women can be affectionate, and we praise them for being bisexual, while men are limited in their options. Sorry guys." I winked as I said that and Alex and Mark laughed.

"It's okay, we understand," Mark said. "Actually, even for us being with you dressed as you are. We don't look at you and see a man in a dress. We see a woman...period. The fact that you still have a penis doesn't dissuade the image. It's just another part of you to be touched and played with."

Chantelle was nodding her head, almost unconsciously. Then she looked at Charles who had been silent the entire time. "Charles, what do you think? After everything that Jo just said...how do you feel about it?"

Charles looked startled by suddenly being the center of attention. He cleared his throat before answering. "I don't know Chantelle. It's a lot to take in. And my thoughts and feelings are two different things. I feel nervous. I think and wonder about my own sexuality if we go through with this. I admit, Jo you did an excellent job explaining things, although I'll probably have some other questions later on. Still, I like your conceptualization of sexuality. It's a good rationalization that, honestly, not everyone is going to accept. But I get it. And I can admit to some curiosity. Still," and he turned back to Chantelle, "are you sure this is what you want? For me to dress and be a woman?"

"Not all the time baby," Chantelle reassured him. "...Just sometimes. And I think that it will only enhance things between you, me, and Maria. It's not like we're out to hurt you. We do care about you and want you to feel included, but we...no, I need you to let yourself go. Let yourself feel things that will make our bedroom adventures sooooo much more enjoyable." There was a gentle pleading in her eyes that was echoed by Maria's. I got the distinct impression that Charles was not merely a boy-toy as Alex and Mark had suggested. He seemed to be more of a boyfriend who happened to be dating two lesbians. But with the opportunity to join them on an even deeper level, I didn't see how he could turn them down. I understood his angst though because, obviously, I'd gone through a similar process. What I thought was great for him, however, was that he was being given a choice as to whether or not he wanted to participate, whereas in my situation, it had been basically forced on me and I then chose to adapt to it.

I suppose my thoughts must have been written on my face because out of the corner of my eye, I saw Mark make a small gesture to Alex. Alex then turned towards me and put his hand on my shoulder. "Hey Jo, what's the matter?"

"Nothing, nothing," I quickly replied. "Just thinking about some things."

"What things?" Maria asked.

"Oh, just...my situation," I said as I moved some strands of my wig behind my ear. "I guess being here and talking about everything and thinking about Charles' 'opportunity' has me thinking about some things that I want to discuss with Frank and Tom."

"Go on," Chantelle encouraged.

"Well, I was just thinking that one of the main differences between my experience and Charles' is that he's being given a choice, when my choice was really more of a forced decision. I don't know...I guess...I mean, I've adapted to the situation and even come to accept it and enjoy it. But still, I kind of envy you, Charles, because you're being invited to explore something different. You're not having it forced on you. I understand that you still may have some reluctance and whatnot, and maybe that's the challenge. Since I was kind of forced to do it, in some ways it made it more okay because I wasn't the one in control. If I did something that I wouldn't have otherwise done, I could always rationalize it and say 'I did it because they made me do it.' But for you, you're making a conscious decision as to where you want to go and what you want to do." I realized that I'd been rambling for a couple of minutes, so I tried to stop and pull myself together. "Just ignore me. I'll talk to Frank and Tom about 'my stuff' later on. For now, the question is to you Charles: what are you going to do? I promise that if you decide to go through with it, we'll try to make it as interesting and enjoyable for you as possible. So...?"

And with that, the attention was effectively shifted away from me and back to our star of the moment. Charles was faced with a decision that would invariably affect his life from this point on. We could all see the internal struggle that he was facing, but as I looked around the room, I could see that he was not the only one with stuff on his mind. Chantelle looked hopeful, as did Maria. Alex and Mark seemed to alternate between approval, curiosity, and resistance. I knew that they'd go for it though seeing as how they'd already enjoyed my pleasures and treasures. I think their reticence stemmed from actually being involved in the transformation process. Of course, for me, I was still coming to grips with what I would suggest if Charles said yes. Mentally, I was revisiting all the things that Frank and Tom had had me do and trying to modify those past actions to make them more...sensitive to Charles' situation.