A Lost Bet Ch. 07

Finally, after a few moments of silent deliberation, Charles lifted his wine glass and took a sip to calm his nerves. "Okay. I'm in. I care about you two too much to not give this a shot," he said while looking at Chantelle and Maria. Immediately, they both started beaming and the mood in the room lightened significantly.

"Now the fun begins," Alex surmised with a smile. "What should we do first?"

I jumped in and said "first things first...a shave. Ladies, why don't you handle that? That way you can decide how much hair you want to leave him with. Gentleman, you're with me...we're going back to that magic chest of yours to pick out a suitable outfit for Charles' coming out party." I clapped my hands and got a bunch of "yes ma'am's" and "yes sir's" from the comedians I was working with. There were smiles all around, and even Charles looked like he was getting caught up in the moment. I hoped he'd continue to feel that way as the evening progressed.

After the ladies took Charles off to the bathroom, Alex and Mark led me back downstairs so we could see what outfits might be available in the trunk.

"Sorry, I forgot something upstairs," I said once we got down there. "Start pulling outfits out, but give me a minute to ask Chantelle something first." The guys nodded and I scampered back up the stairs.

"Chantelle, can you come out here for a minute?" I called through the bathroom door. I stood patiently waiting for her to stick her head out. Once she did, I asked "was there anything in particular that you wanted us to have ready for Charles? Any outfits you wanted to see or anything like that?"

She paused for a minute pondering how she wanted to answer the question. She glanced over her shoulder to watch Maria's efforts at shaving Charles and then turned back to me. "Something cute...like a sundress with a pair of flats...and a short wig, if they've got one." I nodded and shooed her back into the bathroom. With a smile of gratitude she turned and went back to the two loves of her life.

As I made my way back downstairs, I couldn't help but wonder how I'd gotten to be the de facto expert of feminization. The only answer I could come up with was that I was entrenched in it and the others were interested in my experience...and they trusted my judgment as to what would make the process easier and less traumatic than mine. I knew that I'd have to talk again with Frank and Tom about how this all came about. But that was a concern for another day. For today, it was time to help Charles get dressed.

"Alex, do you guys have a sundress, flats, and a wig that will fit Charles?" I asked as I got to the bottom of the stairs.

"Yep. At least to the sundress and wig. The only shoes we have are heels," Alex said.

"Well, I guess he'll just have to make do," I responded.

"Don't worry," Mark interjected. "It will all be fine." They dove into their chest to find the requested items, as well as a few items of underwear that he might want. "Actually, we were thinking about the bet and we have an idea for a photo that just might win the prize."

"What's that?" I asked with blatant curiosity.

"It's a surprise," Alex whispered with a mischievous grin on his face. "But I'm sure you'll love it."

I started to respond when I heard the door open and Chantelle and Maria came downstairs leading a very naked, very clean-shaven Charles. He was wearing nothing but a towel, while the girls were wearing nothing but grins. As they reached the bottom of the stairs I asked him "are you ready Charles?" He nodded.

"Then step right up and see what's been laid out for you." I stepped back as Alex and Mark hammed up their display of the outfit.

"First," Alex said in a faux French accent, "we thought it would be nice if you started with a pair of pale pink, boy-cut, cotton panties and matching cami." He handed the lingerie to Charles who first took the panties and drew them up his legs. They fit quite snugly around his hips and nestled just a little bit into the crack of his ass. I slipped up next to him and whispered "you're probably going to want to tuck 'little Charles' between your legs for now. It will help the panties fit better." He paused and made a few adjustments, dealing not only with the first-timers discomfort of being tucked, but also being tucked in a semi-hard state. Next he took the cami and slid it over his head and arms. As he settled it around his frame, he looked pretty good. He wasn't muscle-bound to begin with, more lithe and sinewy, so the lingerie seemed to accentuate the softness of his frame...making him appear more toned and sensual.

Mark jumped in next with an accent that was an obvious parody of someone gay. But he did it so well that we couldn't help but laugh (and I couldn't help but wonder if maybe he was telling on himself...you know, a little more gay than bi?). "The next thing we have for you is this lovely, flouncy, lavender sundress and matching 3" heels. You'll look FABU in this ensemble." We laughed at Mark's impression as Charles stepped into the sundress and slid it up and settled the straps on his shoulders. The change was amazing. His appearance was taking on a decidedly female form, especially once he stepped into the heels. I heard Maria whisper to Chantelle "My God, his legs are better than mine," to which Chantelle could only nod in agreement.

"Ladies," I asked, "would you be so kind as to help Charles with his wig and makeup?" They quickly agreed and settled him into a chair (not the same one that I'd been attached to) so they could get to work. They fiddled around getting Charles dolled up with just a little makeup...some lipstick, light eyeshadow and very little else. Finally, they settled the wig into place. It was kind of a dirty blond, layered wig that fell to right between his shoulder blades, and with his skin tone...it worked.

Chantelle stood back with a satisfied look on her face. "Ladies and Gentleman and everyone in between, may I present to you for the first time ever...Miss Charlene." And with that, a new girl had been born. Charlene stood up, a tad unsteadily, but turned to face the rest of us while Maria and Chantelle stood behind her glowing like proud parents.

"Wow, Charlene..." Mark said with an appreciative smile on his face. "You look fantastic."

"I totally agree," Alex said after a short wolf whistle. "When you and the girls are doing your lesbian thing, somebody's going to have to keep track of who's who. You really do look...delectable." And if it was possible, Charles, now Charlene, appeared to blush a little bit. Shyly (and naturally too...what was that about?), she tucked a strand of hair behind her ear.

"Jo," she asked. "What about you? What do you think?"

I paused, but only for a moment. "Girl, you've got nothing to worry about. Shoot, you look better than me." Everybody laughed because it was kind of true. "You almost look like you've done this before. But that's beside the point...at least for now. Here's my real question for you: How do you feel?"

Charles, now Charlene, stood there for a minute as she gathered her thoughts. "Well, I suppose you could say I feel...pretty. Being shaved is different...and maybe that's part of what I'm feeling right now. I have to admit, the panties and cami feel...soft...silky...and they make me want to rub something just to feel them slide across my body." We chuckled. "It's more than that, though. I mean, I would never have thought that I could look like this. I mean, as a guy...if I saw me walking down the street, I'd take notice. But it's still a little overwhelming. And Chantelle," she said as she turned to face the girls, "I'm not ready to go out like this, so get that idea out of your head right now." Chantelle had a fake wounded look on her face because she knew that she'd been caught.

"Seriously though, I'm actually surprised that I look as good as I do. I was worried that you were going to have me look like a man in a dress, but that's not the effect that I think I'm getting...at least not if I'm reading the looks on Mark's and Alex's face correctly." Alex and Mark winked at him and gave a couple of wolf whistles as if to emphasize her point.

"You do look really good Charlene," I said. "And I think you benefited from having two women with you who were committed to creating a complete image for you, even if it was to complete their fantasy. Now I imagine that after tonight, there will be some shopping trips down the road for you...but I'll let you fantasize about that on your own. I think the question on everyone's mind is...what do we do with the rest of the night?" We sat there staring at each other with silly grins on our faces while we waited for someone to make the first move.

After a minute or two of people engaging in their own private visualizations, Alex spoke up. "Well I think that we should let Charlene get introduced to being a girl by another recent inductee...Jo, would you care to do the honors?"

"And what is it you'd like me to do?"

"Start with a kiss. That's always a warm welcome," Alex suggested.

I nodded and moved in to face Charlene...close enough to touch and leaving very little space between us. "Close your eyes," I whispered to her. She did and I moved in close enough for her to feel my breath on her neck. I let my arms reach up to caress hers, lightly running my hands from her shoulders down to her hands. As I took her hands, I intertwined my fingers with hers and moved to nuzzle her cheek. She stood motionless, but at each touch, I heard a small sharp intake of breath...almost a gasp. When I nuzzled her cheek, I felt her head move...turning to meet mine. Slowly and lightly our lips touched...gently at first, but with each passing second, the kiss became more intense. My tongue parted her lips to play tag with hers. And as our tongues danced together our hands came apart and pulled the other close. We kissed more and more passionately until soft moans were escaping from both of us. Finally, we separated and looked each other in the eyes.

"Well," Charlene said softly. "That was quite a welcome."

"Umm-hmmm," I echoed. "Just imagine what it will be like when Maria and Chantelle get their hands on you."

"Yes," Maria called out. "We definitely want our chance to break Charlene in...the right way."

"What do you mean 'the right way'?" Charlene asked with a slight tinge of anxiety.

"Don't worry Charlene," Chantelle reassured her. "We'll save the toys and things for when we get home. For right now, we think the guys have a plan." And with a nod of her head, she directed our attention towards Alex and Mark. As we looked in their direction, we saw Mark with the camera capturing the whole experience so it could be relived whenever we chose.

"Jo, you remember that we still have a contest to win, right?" Mark asked. I nodded. "Alex and I came up with a plan...a position that should get us the win. Are you game?"

I was a bit nervous because I couldn't foresee what they might have in mind. "I suppose so. But what's involved?"

"Wait a minute," Charlene interjected. "What are you guys talking about?"

Alex decided to respond to Charlene's query. "Don't worry Charlene. You might be involved in this, but not in any way that should make you too uncomfortable. It's Jo that has the decision to make because this might be a little tough at first."

"Okay, now I'm getting worried," I said. "What are you guys talking about?"

"Basically...a foursome Jo...and you're the center of attention," Mark said. "The challenge is going to be how much you can stretch."

I stood there for a moment and slowly, understanding spread over my face and my eyes widened as I grasped the full implications of what they were suggesting. "Wait a minute...you're telling me you want to fit two of you in my ass." They nodded slowly. I took a deep breath and pondered about what they were asking. Finally, I screwed on my resolve and said "O...K..."

To be continued...