Guys' Retreat Pt. 03

Part 3: Serving

I don't know when Vince came into the bedroom. Amazingly, I got to sleep quickly and slept soundly until about 7:00, when light came streaming into the room. I looked over and saw that Vince was still asleep in his bed. I didn't want that to change so I very quietly got my clothes together and tiptoed to the bathroom for a shower.

A long hot shower can alleviate a lot of pain. It felt good, but I didn't really feel like the pain was abating. I tried to think of the shower as a metaphor for washing away what had happened last night. But that wasn't working because I knew that last night was prolog to the next few days.

After my shower, I got dressed in the bathroom and planned to head directly to the kitchen for some coffee. But I'd left my phone in the bedroom and wanted to get it.

I was being as quiet as possible but either I woke Vince up or he was already awake and my movement roused him even more.

"Hey, you're up already," Vince said.

"Yeah," I replied noncommittally. I just wanted to get my phone and get out to the kitchen.

"Hey!"

"What?"

"I need some attention this morning." There were several reasons I wanted to get out of the room without waking Vince, but this was the most important one.

"Come over here," Vince commanded. What was I supposed to do? Kent and Vince had me in a cage just as surely as Nicole did.

Resignedly, I walked over to Vince's bed, pulled the covers down, and took care of his morning woody.

This was just as horrible and disgusting as it had been last night—in some ways it was worse without the beer and weed and in the light of the day. And it didn't help that, when I'd finished, Vince said, in a bright, cheery tone, "Thanks. That was great. You're getting really good at that."

Fortunately, Vince stayed in the bedroom for quite a while and there was no sign of Kent. I was able to have an hour's respite. Just me and my coffee. Somehow, my solitude gave me at least a brief moment of something approaching normalcy. That was broken when Kent came out of his bedroom and headed for the kitchen.

"Ah, you're up. Good," he said. I hoped that his approval of my being up wasn't motivated by the same thing Vince's was. Fortunately, it was not. But the cause of his pleasure at my being up was troubling, nonetheless.

"You can fix me breakfast," Kent said in a domineering tone.

"What?! ... Fix your own goddamn breakfast, asshole!"

"I don't think you quite understand the situation, Brian. For this trip, you're taking care of all of our needs. I know you'd be happy just to suck our dicks, but you'll do whatever we want."

Happy to suck their dicks! I thought. What an asshole! But he and Vince had me over a barrel. So I cooked the asshole's breakfast, and Vince's, too, when he finally rolled out of bed.

When I'd finished cleaning up, Kent called me into the living room area of the cabin.

"Vince and I have been talking about this situation and we've decided that we need to make this easier for you, Brian," he said. The words sounded good, but I was apprehensive and, as it turned out, for good reason.

"We think that your new role is difficult for you." That was an understatement! "It must be difficult for a straight man to do what you'll be doing while we're here." Right again, I thought.

"It must all seem too gay to you. ... So, we think it will be easier for you if we help you quit thinking of yourself as a straight man."

What the fuck?! What was he talking about?

"Well, I am a straight man. So that's that!"

"But you need to stop thinking of yourself that way. And we know how to help you."

And they proceeded to tell me their great plan to "make things easier for me". They were going to make me dress up in Kent's wife's clothes. Both Kent and Ann kept a lot of clothes at the cabin so they wouldn't have to pack much when they came up here. Kent told me that he had already picked out a nice outfit and laid it out on the bed in his room for me to try on.

"I'm not doing that," I insisted. "That's fucked up."

But Vince and Kent, drunk with their power over me, insisted and, when Vince started playing back some video from last night on his phone, holding it up so I could see it, I relented.

I walked into Kent's bedroom, resigned to my fate. It was going to be an even worse fate than I'd feared, I realized, when I saw what Kent had laid out.

Since he and Ann sometimes went into town when they stayed here, she had dressy outfits in addition to her clothes for hiking and just hanging out in the cabin. What Kent had laid out was, it seemed, the sexiest outfit of Ann's that he could find. It was a short, tight, green skirt paired with a sheer cream-colored blouse. And he'd laid out stockings, lacy panties with a matching bra, and high heels.

I didn't have a choice, at least not an acceptable one. So, I stripped out of my clothes and began putting on Ann's. Fortunately, Ann was not petite and I was small for a man. Things didn't fit perfectly, but they did fit. Sucking in my stomach, I could fasten the skirt. And I could hook the bra on its largest setting. Even the panties fit, though they didn't hide the bulge of my chastity cage. The shoes were a problem. I had to cram my feet into them to get them on at all and, then, they hurt like hell. I decided to leave them off.

Before going back out to the living area, I glanced in the mirror. I looked ridiculous! I didn't look the least bit feminine. My face and hair were unchanged and you could see the hair on my chest and, through the stockings, on my legs. I was just a man in drag. It was jarring and unattractive. Maybe Vince and Kent will agree and give up on this particular humiliation, I thought, or at least hoped.

There was to be no such luck. When I walked out of the bedroom, Vince gave out a wolf whistle. I wasn't the least bit attractive so this was just designed to humiliate me.

"You think she's hot???" Kent needled Vince. "I think she needs some work."

"Well, yeah," Vince agreed. "But she shows promise."

"Perhaps. ... That remains to be seen. But we'll do what we can."

"Come here, Brianna." Okay, so now I'd lost my name, too. They were going to call me 'Brianna'. Shit!

When I was standing in front of Kent, he made me turn around slowly posing for him.

"Where are your shoes, Brianna?"

"They didn't fit so I left them in the bedroom."

"Okay, that's a problem. We'll need to come up with a solution because you can't really feel like a woman without nice high heels."

"But that's not the only problem, Brianna," he continued. "We need to do something about that disgusting body hair. Don't you know that a woman should be smooth all over?" He paused, as if thinking more deeply about the issue. "And we need get some make-up on you. You know, there's nothing wrong with making the most of what you have by laying on the make-up."

"Don't you think those things would be good places to start, Vince?"

Vince agreed and Kent gave me my orders.

"We can wait on the make-up but, right now, you need to go to the bathroom, strip down, and shave off all of your body hair."

"Hell, no!" I said. "That's like a permanent change. I'll be shaved when I go back home. What will I say to Nicole?"

"First," Kent replied, "it's not a permanent change; hair grows back. Second, and this is really the important point: I don't give a damn. So, you'll go back home shaved. It doesn't matter to me. What will you tell Nicole? I don't give a shit."

And I could see in his face that he didn't. This guy who for years I'd thought was my friend, really didn't give a shit if he ruined my life.

"Now GO!" he shouted.

So, just minutes after I'd put on Ann's clothes, making myself look ridiculous, I was in the bathroom taking them off so I could make myself look even more ridiculous.

It's not a small job to shave your entire body. I'm not extraordinarily hairy but, still, there's your arms and legs and chest to do. I did it all. But I skipped my pubes. Kent had said "all of your body hair". But what he's seen that he didn't like was the hair on my legs and chest. And I'd taken care of that.

Putting Ann's clothes back on, especially the stockings but the other things, too, was a totally new experience. I'd never realized what a difference being shaved would make in how the lacy panties and bra would feel or how different, and more sensuous it would feel to pull the stockings up over smooth, hairless legs.

When I was dressed again, I went out to the living area. Kent was there but Vince wasn't.

"Vince had to run an errand into town," Kent explained. "Let's have a look at you now, though. I'm sure that if I approve, Vince will, too."

So, once again, I was posing in drag for my former friend. Kent was showing signs of approval. Then, he said, "Now, pull up your skirt and pull down your panties. Let me see what you've done with your crotch."

Well, I hadn't done anything with it, but I had to show him, anyway. He took one look and immediately sent me back to "finish the job".

I did the best I could around my chastity device and went back out for inspection. At this point, Kent was satisfied—with my grooming job, but not in other ways.

"Well, Brianna, you've done about as well as you can at this point," he said. "Now get over her and give your first blow job en femme. ... I think you're going to like it better."

I was pretty sure he was wrong. But he didn't really give a damn how much I disliked it. He only cared about whether I did it. And, on that score, he had me by the balls.

Kent started to unzip his pants and then stopped. "No, I think you should unwrap your present yourself."

My present, I thought. Fuck you, you asshole! But I got on my knees in front of him, opened his pants and, when he raised up in his chair, pulled them down to expose his cock.

It was completely soft now; it didn't look nearly as formidable as it had last night when he was assaulting my mouth with it. But I knew that would change.

I put my thumb under his cock and raised it, stroking it between my thumb and fingers for a few seconds as it began to respond.

"I said a blow job, not a hand job. Get to work, bitch."

I didn't get to work right away, though. I was in turmoil. I looked up at Kent and pleaded, "Why are you doing this?" I felt my voice quaver and realized that I was on the verge of tears. I tried to control my voice so Kent wouldn't notice. "I thought we were friends."

"We were, I guess," he replied. "Things change." Kent seemed completely untroubled by the change. Hell, I guess he liked it.

"Why? ... Why do this to me?"

"Bad luck for you, I guess," he said. I suddenly felt silly, in women's clothes, on my knees, looking up at Kent with his dick in my hand. But I didn't want to let go of his cock because he looked like he was going to actually try to explain this to me and I was sure that If I did anything to distract him from that, he'd stop. And letting go of his cock would surely distract him. So, I just sat there kneeling before him and holding his cock in my hand.

"Ya see, Vince and I decided we weren't going to do the whoring thing this trip. It was getting kind of old, anyway. He's in a new relationship and he's trying to make it work. I don't want to run the risk of having happen to me what happened to you. So, picking up sluts at a bar or hiring hookers was out."

Kent went on, "We figured that, as far as sexual release went, it was going to be whacking off to porno flicks. And that's how it started out. But then Vince discovered your secret." He paused for a minute, taking a drink of his coffee. "And Vince argued that, since Nicole had already emasculated you and you were always kind of effeminate anyway, we might as well take advantage of the situation to get off in more interesting ways than just jacking off."

Effeminate! Shit! What the fuck?! It was true that I was a shorter and thinner than Kent or Vince. I was shorter and thinner than the average guy, and they were both definitely taller and more muscular than average. But effeminate?

Kent's "explanation" didn't make sense to me. Friends don't do things like that to friends. In fact, decent people don't do things like that at all. But I guess it made sense to Vince and Kent. Or, at least it made enough sense that they were willing to offer it as an explanation.

"Speaking of getting off in more interesting ways, Brianna," Kent said, remembering why I was kneeling at his feet and holding his cock, "get to work. You've got a job to do."

I wasn't going to be able to delay any longer. I'd figured out this morning with Vince that, given that I couldn't refuse their demands, the best thing to do was to get it over with as quickly as possible. I began stroking Kent's cock again and brought my lips to it.

As I wrapped my lips around Kent's rapidly hardening cock, he began taunting me. Maybe his purpose wasn't to humiliate me further, but that was the effect.

"Oh, God, Brianna, that feels so good." He inhaled hard. "You're a great cocksucker." I didn't want his praise but I was working hard to try to get him off and get this over with. I was bobbing my head up and down over the head of his thick shaft and jacking the base of his sock with my hand.

"Kiss my balls, Brianna," Kent commanded.

Jesus Christ! Was there no end to the humiliation he would subject me to? I thought. But I didn't have a say in this so I pulled my mouth off his cock and kissed his hairy balls. That wasn't going to get him off so, as soon as I thought he'd allow it, I licked my way back up to the head of his shaft and began trying to work him to an orgasm again.

I cupped one hand under his balls, thinking that this might help speed things along. I'm not sure if massaging his balls helped or not, but soon I felt his hips begin thrusting. He put his hands on the back of my head to control my movement as he began driving in and out of my mouth.

And then his cock exploded. Kent held my head hard and kept his cock buried deep in my mouth as he shot stream after stream of salty cum into my mouth. I was having trouble breathing and gagged as his cock pounded the back of my mouth as if trying to invade my throat. But I couldn't pull away. He was holding me tightly.

When Kent finally collapsed back in the chair, I pulled away, gasping for breath. My mouth was still filled with the taste of his cum and I swallowed several times to try to clear the taste from my mouth.

Kent recovered before I did. "That was terrific, Brianna. Now isn't it so much easier for Brianna to suck a guy off than for Brian to do it?"

It wasn't! But Kent wasn't really asking a question. I didn't know what he was doing, really, other than playing a sick game of humiliation. I didn't care. For the time being, no demands were being made of me. Vince was still on his errand, whatever that was, so my room was a place of solitude. I closed the door and flopped on the bed, hoping to fall asleep. It didn't work, but at least I was alone.