Guys' Retreat Pt. 04

Part 4: Brianna

I heard Vince drive up in the car. I didn't leave the room, though. Better to stay here as long as possible.

That turned out not to be very long, though.

"Brianna," Vince yelled, "come out here. We have some presents for you."

Reluctantly, I got up and went to the living area of the cabin. Vince had three large shopping bags sitting on the floor next to the chair he was sitting in.

"Look what we have for you, Brianna." Shit! I wish they would quit calling me that!.

"Kent told me that you were much more comfortable doing your duties dressed as a woman." It wasn't true at all, of course. And I didn't really think that either Kent or Vince believed it was. That didn't stop their act, though.

"Look, Brianna." Vince pulled out a shoe box from one of the bags. "Ann's shoes were too small for you but we knew that you wanted some high heels to make you really feel like a woman. So I got you these."

These were four-inch black pumps with ankle straps. Shit! I thought, how do they expect me to walk in those?

Worse was yet to come, though. Vince pulled out another shoe box and proudly opened it as if I would be delighted by his gift. He pulled the tissue paper aside to display what can only be called 'fuck me pumps'. They were pink suede platform shoes, with a bow on the side and heels that were at least 5 inches high.

"Aren't they sexy, Brianna?" Kent said. "Vince is really trying to make this easy for you. I'm sure that once you get the hang of walking in these, just putting them on will make you feel like an incredibly sexy woman. Right?"

It wasn't right, but he went on. "And, when you feel like a sexy woman, there's nothing you'll want more than to fall to your knees and suck a hard cock."

The shoes weren't all that Vince had bought. Obviously, he'd found a store that caters to transvestites. He pulled out item after item designed to feminize and humiliate me. There were breastforms, a couple of wigs—one blonde, one curly brown—and lots of lingerie. Ann's didn't really fit me very well and, besides, it looked like Vince had a taste for things that were more risque than what Ann had at the cabin.

"You did great, Vince," Kent said. "I'm sure Brianna is delighted—so delighted that she doesn't know what to say. But I know she'll love trying on all of these things. ... And, I'm sure they'll make her look and feel much more feminine. I can hardly wait to see her in them."

Vince and Kent decided that they shouldn't have to wait long. They also decided that I couldn't be trusted to handle my more advanced feminization on my own. The afternoon was spent in Kent's room with both Vince and Kent serving as my dressers and make-up artists.

About half the time when they were working on me, they ignored me as if I wasn't even there. I was just an object for them to work on—a project. The other half, they went into their banter that was based on the pretense that I was loving what was happening.

"Don't you just love this, Brianna?" they'd say as the pulled out the various items of clothing.

When they'd glued the breasforms on my chest and fastened the lacey lavender bra over them, Vince said, "Wow, Brianna! Look at your rack. You're going to have men cumming at the sight of you."

When they had the blonde wig on my makeup done, and my lips my glossed with deep red lipstick, Kent added, "Look at yourself; you look so pretty. You're going to make all the guys want to blow their load in your sweet little mouth."

I liked it better when they just treated me like an inanimate object.

They had me put on a very tight, low-cut cashmere pullover sweater and a very tight, short skirt. It barely covered the tops of my stockings. When I sat down, the straps from my garter showed. They didn't mind. They were aiming for crass, not class, and they were hitting their target.

And, finally it was time for the shoes. Fortunately, they asked me to try on the black ones, not the pink "fuck me pumps". I didn't think I'd ever be able to walk in those.

The black pumps were bad enough. I almost fell over when I stood up. When, at their insistence, I took a few steps, my ankles wobbled like crazy. How the hell did women do this? And, they made it look easy. They made it look sexy. I just looked like a newborn colt trying to stand on its own legs for the first time.

"Go look at yourself in the mirror, Brianna. You'll like what you see."

I was pretty sure I wouldn't, but I walked—or, really, wobbled—over to the mirror in the closet door.

The image looking back at me stunned me. I wasn't passable, not on any careful inspection. But I didn't look like a man in women's clothes, either. I'm a pretty thin guy but the breastforms and the skirt gave me a feminine shape. And my legs looked pretty terrific, actually. The make-up softened some of my masculine facial features and the wig completed the look. At a quick glance, I looked like a woman—a very cheap, slutty woman.

I looked at my reflection for a while, sometimes moving just to remind myself that it was really me in the mirror. Of course, Vince and Kent interpreted this—or at least pretended to interpret this as me admiring the change in my appearance.

"Nice, isn't it" Vince said—a statement, not a question.

"No!" I replied. "It's not nice. I look ridiculous and you guys are really fucked up, you know that?"

"Fucked up?! I don't think so," Kent said. "If you could think back to when you were Brian, I think you'd agree that Brianna is pretty hot."

"Whatever," I said in exasperation. "You guys have had your fun humiliating me and dressing me up. Now let me get out of these clothes." (I didn't think it would work, of course, but it didn't hurt to try.)

"Out of those clothes? Well, you'll be out of those clothes sometimes, Brianna. But you won't be in men's clothes this weekend. Women wear women's clothes, not men's clothes. So you'd better get used to it."

Vince chimed in, "In fact, you need some practice in those shoes. So, why don't you clean up the cabin and start cooking the chili; it's got to simmer for a couple of hours so you need to get going on it. Right now, though, you can bring us each a beer."

I didn't really have a choice—not one I could live with—so I brought them their beers and started on the chili. While I cooked and cleaned up, still wobbling in my high heels but improving, Kent and Vince huddled over a laptop doing God knows what. But they were up to no good, I could hear them conspiring and I knew the objective of their conspiracy was my further humiliation.

When the chili was simmering and I'd cleaned up the cabin enough to claim that I'd finished, I quietly went into my room, hoping they wouldn't notice and I could be left alone for a while.

And, for a while, I was. But only for a while.

"Hey, Brianna," Vince called out, "come here. We have a great surprise for you."

I doubted that, but I went out to see what fate awaited me.