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A Lost Bet Ch. 03

I woke up the next morning feeling a little tired, a little stiff, and definitely sore. But it wasn't the kind of soreness that came from exercise. It was just my rear. The beads and the pounding from Tom had done their job. As I rolled out of bed, I felt the tampon in my rear and immediately wanted to get rid of it. I started to walk but even that felt different. I hoped the feeling would go away, but I didn't that it would because I knew that whatever Frank and Tom had planned for me would probably culminate in some sort of anal experience. As I grabbed my things and made my way to the shower, I heard Frank in the kitchen.

“Good morning Jo. Did you sleep alright?”

“I slept better this time than I did back at your house Frank, if that's what you're asking.” My feelings were still a little raw and bitterness coated my words. Frank just shook his head and went back to eating breakfast.

“Jo, while you're in the shower, I'll lay out your ski outfit for you.”

“Why? Do you think I'm incapable of dressing myself,” I snapped.

“Dammit Jo. Just chill for a minute. All this hostility is going to make this week really rough and it doesn't have to be that way.” Frank sounded exasperated.

“Alright, alright. I'm sorry.” I said. “I just want to go get cleaned up.”

“Fine, but don't take too long. Tom should be ready in a few minutes too, and I'm eager to hit the slopes.” Frank looked like he was done, but there was one more thing he wanted to say… “By the way Jo. One last request.”

“What's that Frank.”


“What? Why?” I asked.

“Well, for two reasons,” Frank responded. “The less important reason is that I want you to.” He paused for a moment. “The more important reason is that if you're going to be out wearing women's clothes, do you really want a lot of people looking at you?”

That caused me to pause because up until that moment, I hadn't considered that Frank and Tom might actually make me leave the house en femme.

“Frank, you're not seriously going to make me go outside dressed like a woman are you?” I started to feel panicked.

“Yes Jo, I am. But I still want you to be comfortable.” He said. “I figure that if you shave…everything…then maybe, with a little make-up, you could pass for a woman. I mean, you won't be able to stand up to any in-depth scrutiny, but hopefully, it will be just enough to minimize the stares that I know you're worried about getting. Just trust me.”

And with that, I was face-to-face with a stark realization. Frank and Tom wanted their 'ski bunny' and I was it. And if they wanted to go out on the town, they planned to drag me along. If I didn't want to be further embarrassed, I needed to get with the program. I started to shake.

“Frank, please don't make me do this. Don't make me go out like a woman. Just give me my ski clothes so I can be a man for the day and when we get back, I promise, my attitude will change. I'll be more feminine in the cabin. I give you my word. Just don't make me go out dressed.” I begged with fear and nervousness tinging my voice.

“It's too late Jo,” he said and I cringed. “I'm not doing this to be cruel. Honestly, it's just that the only clothes we brought for you are women's clothes, so you don't really have much choice as to what you're going to wear. Where you do have some control is in how people respond to you. I can guarantee you that wearing the outfits we brought will generate stares if you've got facial hair. Take the hair off and you'll get away with a lot more. Plus, I've got another special item for you that should also make it easier.”

“God Frank. Do you hate me? Is that why you're torturing me like this?”

“No, it's not that at all. Tom and I just have specific things that we like and want. This time around, we hadn't planned on things taking the turn that they did, but now that we're here, we both intend to make the most of it. If you could stop being so pissed off at us, you'd see that our behaviors towards you are limited in their context. Once the bet is over, we'll treat you like the man you are. But until, we're treating you like our girl. And we want to make that easy for you, but you keep fighting us every step of the way. Now I don't mind a little bit of a challenge, and a little fight from you keeps it interesting and fun. However, once we step foot outside that door, Tom and I will only be able to do so much for you. You're the one that's going to control how others perceive you. If you want them to see you as a man en femme, then that's what they'll see. If you want to make them second-guess what they're seeing, then do what you've gotta do. The second option will be less embarrassing for you, I guarantee it. But if you want to fight us, go ahead. You'll be bringing the external humiliation on yourself, then you'll have to deal with the consequences once we get back and are behind closed doors.” Frank stopped his diatribe and stared at me. “Jo, I've told you what I wanted. I've given you options when I chose to, but now, we're entering a situation that is beyond my control. It's your turn to make the decision. What are you going to do?”

Tom had, without my knowing, stepped out into the hallway and he echoed Frank's question, “what are you going to do Jo?”

Reluctantly, I nodded my head and turned back towards the bathroom. “Okay,” I responded meekly. “I'll shave. I'll do whatever I have to in order to blend in as much as possible in public.” And with a tear in my eye, I closed the bathroom door knowing that I had just made a major decision to do whatever I had to in order to survive. It wasn't physical survival that I felt threatened with. It was my emotional well-being that I had to look out for. I figured that following the commands from Frank and Tom would be easier to cope with than the potential public ridicule I would face if I continued to be stubborn and obstinate. I wasn't happy with my decision because I felt like a piece of “me” was slipping away, but I hoped that in the long run things would be easier if I did things their way.

So, with my fingers crossed and a wish on my lips, I began getting cleaned up. I shaved my face, my body, my legs, even my groin. I showered, patted myself dry, then started putting on what was to be my public persona for the next few days. I slid on another pair of cotton panties, some hi-cut bikinis, and a matching camisole.

“Jo,” I heard Tom call through the door. “We left your clothes on your bed. Get a move on or else we're gonna get a bad parking spot and miss out on the best runs of the morning.”

“Okay, I'm coming.” I stepped out the bathroom and made my way across the hall to my room.

“Let us know when you're done getting dressed,” Frank said. “Don't forget, we've got at least one more item that ought to help. Oh, and don't worry about any tampons or other anal gear. At least not for today. Unless you need them or want them…?”

“No, no. I'm okay. I'll be dressed in a few minutes,” I responded.

As I shut my door, I looked at the clothes they had laid out. Since it was cold, they'd left me some silk thermals and sport socks to wear, but it was the ski outfit that did me in. They'd gotten me a baby blue turtleneck, a black fleece vest, a pink and blue ski coat, and some black stretch pants with a decisively feminine fit. I knew that anybody who saw me wearing those clothes would think I was a girl, so I was semi-glad that I'd gone along with Frank's suggestion to shave. After sliding into all the clothes but the jacket, I turned to the dresser. There, they'd left an array of make-up with a note that said “use only what you want…but lip gloss is required.” As a show of defiance, I only put on the lip gloss. It was like winning a small victory.

I grabbed my coat and headed out the room to meet the guys.

“Jo, like we said, we've got one more thing for you. Sit down please,” was Tom's request. “This will hopefully make it a little easier to feel feminine and it should pass casual inspections.” Then I felt Frank placing something onto my head. It was a wig. I knew that the minute I felt the strands brush the side of my face. Frank tugged it, and shifted it a little until Tom gave him the ok. “Have a look,” said Tom as he moved from in front of a mirror.

And there I was. A softer face, made so by the black wig that framed my face, falling to just below my shoulders, and lip gloss giving my lips kind of a wet look. I wasn't perfect. Anyone looking closely would be able to tell that I was a guy, but for the first time that morning, I felt like I had a chance of making it through the day without broadcasting my (remaining?) masculinity.

“We added some adhesive to the wig that will definitely keep it from falling off,” Frank said. “You can put it in a ponytail if you want, or even get it styled later on…if you want. But it won't come off until we add some of the solvent that came with it. So feel secure that you're not going to be flying down the mountain and then see your hair go in the opposite direction.” He smiled.

I offered a small smile of thanks back to both of them.

“Now, are we ready to go? Jo, got your tennis shoes?” I nodded.

“Okay then. Let's hit the slopes.”

“Oh yeah…Jo, one more thing to remember,” Tom added.

“What's that?”

“Well, we know you can keep a few small items in your pockets, so here's some lip gloss, a tampon if you need it,” Tom smirked as he said that, “some money, and your cell phone. Last thing. Don't forget to use the LADIES room if you have to go to the bathroom.”

“And for Pete's sake, sit down while you're in there,” Frank added through a sudden fit of laughter.

My blush would have been visible if not for my brown skin.

“Off we go.”

And off we went. We got to the slopes and, while we had missed a chance to lay “first tracks,” we still got to do some great skiing. The guys were gentlemanly in their behavior towards me all day. They joked with me, teased me, and flirted with me as though I was a real girl. It was a little unnerving at the beginning because I was so worried that I'd be “read.” Of course, it probably was a little easier since I had on ski clothes, which are generally a little bulky, hiding me. Still, once we got going, things were okay. I actually forgot about my appearance while we were actually skiing. Once we stopped for lunch though, I was reminded of my current state because I had to go to the bathroom. And that was the one time during the day that the guys subtly reminded me of my current position. When I made my intentions known, Frank leaned in and whispered, “remember…it's the door with the girl on it.” Then he sat back with Tom and laughed. I quickly hustled off to take care of business, remembering to sit down while I was in the stall, and even going so far as to touch up my lip gloss as I was at the sink. I quickly made my way back to the guys who were still sitting at the table, enjoying what was left of lunch.

“Ready to go?” Tom asked as I got back to the table. I nodded. We gathered up our things and made our way back out for the afternoon runs. It felt really good to be floating down the mountain, twisting and turning and enjoying the challenge. But after about 2-3 hours, we were all ready to call it quits. We knew it was time to go when Tom got to the bottom of the hill and, in trying to show off, came to a stop, then promptly flipped over when his skis stuck in the slush at the bottom of the hill. We all laughed and got our gear together as we headed back to the truck.

“Jeez, I'm sore,” I said as we climbed into the truck. “It's been a long time since I've had that type of workout.”

“Really,” said Frank. “What about last night?”

“That was different and that resulted in a different type of localized soreness. This, this is an all over type of soreness.”

“Tell you what Jo, since you've been such a good sport today and it looked like you actually enjoyed yourself, how about I give you a massage after dinner?” I looked shocked and surprised at Frank's offer. But being naturally suspicious, I had to ask “what's the catch?”

“No catch,” Frank responded. “Just trying to be nice. I'm not saying that there won't be 'extracurricular activities,' I'm just trying to help you take some of the edge off.”

I looked at Tom for confirmation.

“Jo, you should do it. It doesn't all have to be forced. We told you that we wanted you to have a good time too, so let us hook you up. Once we get back to the cabin, take a bath, read a book. We'll have dinner, then for tonight, I'll make myself scarce. You two can have fun and do whatever. I'll rejoin the activities tomorrow. Does that sound any better?” Tom asked.

I was skeptical but figured I might as well take the shot, if for no other reason than to see if they were being sincere, or if they were just trying to sucker me in for something else.

“Okay Frank. After dinner, I'll take you up on your offer.” I was still a little nervous about getting a massage from a guy that I knew, but I figured he'd already fucked me, so it's not like I had to worry about him making a pass. That was guaranteed. But it was still different, because before, I hadn't been in control. I had been forced to submit. Now, I was giving myself over to Frank willingly and that was my struggle. That was the thought on my mind as I fell asleep for the rest of the ride back to the cabin.

“Jo, wake up Jo. We're back,” Tom said.

I had no idea that I'd been that tired. “Oh, okay. Thanks.” I almost fell out of the truck while trying to gather my things together.

“Hey, try not to drown while you're in the bath, okay?” Frank laughed as he noticed my struggles. “Here, let me take the skis and poles.” I was again surprised by his behavior because it was just so different from anything I'd seen or experienced before. I decided not to look a gift horse in the mouth and let him carry my equipment into the house while I headed straight for the bathroom to start the bath, then to my room to change. As I went into the bathroom for the bath, I heard the guys watching TV and planning dinner, so I figured I'd be undisturbed for awhile. As I started to lower myself in the tub, I remembered the wig and quickly found one of the scrunchies they'd provided me with and tried to put up my hair the way I'd seen past girlfriends do it. It wasn't perfect, but at least my new hair didn't get wet.

I must have lounged in the tub for almost an hour, just soaking the stresses of the day away. Finally, when my stomach reminded me that it needed attention too, I got out of the tub and dried off. As I made my way across the hallway I heard Frank call out “I left two outfits on your bed for you to wear tonight. Your choice.” Then he went back to watching TV. As I entered my room, there on the bed were my options. One was a black sheer teddy with an open back. The other was a sheer black chemise with matching thong panties. I was intrigued by both of them, but decided to go with the teddy. Slowly, I pulled it on, first sliding my legs in, then tugging it close against my body, tucking my penis beneath me, before finally attaching the halter straps behind my neck. It was a unique type of feeling, being wrapped in the teddy as I was. I decided to keep Frank guessing by grabbing one of the sweaters that he'd bought for me on the way and pulling that on. I also grabbed a denim skirts and quickly slid that on with a pair of pumps before sauntering out for dinner. As Frank looked up with a question in his eyes, I ignored him and sat down at the table while waiting for Tom to bring the food.

“Well, that wasn't quite what I bargained for,” said Frank.

“True,” Tom added, “but you didn't specify in the note that she couldn't wear something on top of the outfits that you selected.”

“Well, I guess I'll just have to be more specific next time,” Frank responded with a smile.

As we ate, we talked about the runs we enjoyed during the day and we made plans for the rest of the week. We decided to take the next day off, then ski at a different resort for the following days. But as for tomorrow, the guys wanted to take me to the casinos for a little gambling and a show.

“I'll go to the show, but I'm not gambling. Don't think I've forgotten that that's what got me in this mess…or position to begin with. No thank you. No gambling for me.” They both laughed.

“That's fine. You can be my arm candy,” said Tom.

“Well, you two have fun tomorrow. I think I'm going to gamble for awhile, but maybe I'll hook up with you for the show. But as for tonight, I think I'm ready to flex my muscles a little bit.”

“That's my cue. You kids be good now.” And with a wink and a nod, Tom excused himself from the table, put his dishes in the sink, then retired to his room to watch movies or sleep.

“So…” Frank looked me up and down. “Where would you like to receive your massage? Your room or mine?”

“So many decisions,” I joked. “What am I to do?”

“Pick one, before the decision is made for you.” Frank was about to take control again. “I'm going to clear the table. When I'm done, I'm going to find you wherever you are, then I'll give you a massage and we'll see how things go from there.” He got up and started stacking dishes. I waited until he had ventured further into the kitchen before sliding my chair out and making my way down the hall. I was still mentally adjusting to the role that I had so willingly taken on during the day, but I swallowed my nervousness and made my way into Frank's room. As I stood in the doorway, I heard footsteps behind me.

“Go ahead.”

I turned to face Frank. I looked him in the face and let him see my confusion and distress.

“Don't worry about anything. What happens here stays here.” With that, he gently grabbed my waist and guided me further into the room. “Before we go any further, I want to see what you're wearing. Just take off the sweater and skirt. Keep the shoes on.” Then he stepped back and waited for me to strip. Slowly I shimmied out of the skirt, letting it fall to my feet. As I started pulling the sweater up over my head, I heard him say in a soft voice “very nice.” I stood there before him, dressed only in a teddy and pumps, with my hair hanging across my shoulders and my hands crossed in front of me.

“Lie face down on the bed.”

I moved around the side of the bed and crawled onto it. I put my face on the pillow and tucked my hands underneath the pillow so he wouldn't see them shaking. I heard him taking off his clothes. By the time he got close, he was wearing only his boxers. Then I heard him turn on some soft music. He didn't sound like he was close by so I opened my eyes to peek at where he was. I saw him lighting candles around the room and I thought to myself “is he trying to set up a seduction.” I didn't say a word. I just lay there and closed my eyes waiting for him to make the next move. I felt him looking me up and down, soaking the image of me in and burning it in his memory. I closed my eyes and waited for him to make the next move. I smelled it before I felt it. It was the scent of perfume. Then, I felt lotion being spread on my back. I felt Frank's hands kneading the muscles in my back, pushing all soreness and stress away. He started up towards my shoulders and worked a knot that had been there all day. “Relax” was all he had to say. Then he continued with the massage. He spent a few more minutes working on my shoulders and arms, then started working his way down my back again. I felt him spread more lotion on my lower back as he neared my hips and ass. He massaged my lower back and ass and only flirted with my asshole. I felt his fingers dip into the crack of my ass and just lightly probe my hole before he continued past it and started working on my legs. Slowly and methodically, Frank worked the muscles of my legs and involuntarily, I felt a moan escape my lips. I blamed it on the skiing we had done earlier and appreciated the relief his hands provided. Minute after minute, he worked on my legs moving with tender care further and further down until he reached my feet. I was surprised when he started taking my shoes off. I started to say something, but Frank stopped me. “I'm going to put them back on in a minute. I just wanted to massage them too, and put some lotion on them.” I didn't say another word. I was still somewhat dazed by Frank's outpouring of gentleness and caring, and I was relishing the sensitivity with which he treated me. His massage nearly put me to sleep, but I suppose it was my curiosity at where he would take things next that kept me awake. Still, I could see how people got addicted to receiving massages.

Updated: December 17, 2016 — 12:23 pm
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