Guys' Retreat Pt. 05

Part 5: Brianna's Training

"Vince had a terrific idea, Brianna," Kent said. "It's really going to make this easier for you."

"Yeah," I said, noncommittally, knowing full well that whatever Vince had come up with wasn't going to be to my benefit, though I was sure it would benefit them.

"Yeah. We've been downloading some videos for you to watch. You're going to love watching these! They'll inspire you and make you love everything we do with you."

"Sit right there in this chair," Vince ordered, as he turned on the TV and began casting to the TV some videos he'd downloaded to his computer.

Now I knew what they'd been up to. They'd spent the afternoon finding and downloading a bunch of sissy training videos. You know ... the kind that pretend that they can turn you into a sissy cocksucker.

They insisted that I take hit after hit of a joint because, they claimed, it would make me more receptive to the message of the videos.

So, I spent the late afternoon stoned, watching videos that told me things like: "You're not a man"; "You're a cocksucking sissy bitch"; "You don't have a cock; you have a little limp clitty"; "Your little clitty couldn't satisfy a woman"; "Your clitty needs to be locked away".

My tormentors got a laugh when they heard the last one. "Well," Kent said, "you got that one down."

These videos showed men feminized and masturbating like women or servicing men in every way possible. And they kept reinforcing messages like, "You love cock"; "All you can think about is men's hard cocks"; "You want to suck cock"; "You want men to cum in your mouth"; over and over again.

There were a bunch that showed guys having sissygasms either from dildos or from being fucked in the ass by a huge cock. In some of them, the guy was wearing a chastity device; in one, it was the same model chastity device as mine.

"Look at that!" Vince said. "See, she can get off even with her little clitty locked up. Wouldn't it be great if you could do that, too?"

I couldn't agree that it would be, but I suspected that they were going to try to see if they could make me sissygasm.

I'd seen videos like this before; I'd seen some of these very videos. I'd even beat off to some of them. And, I was getting a little hard watching some of these now.

Fortunately, the tight skirt I was wearing kept my cock from making my chastity device rise up enough to reveal this to Kent and Vince. They would have surely used this for more humiliation.

My "friends" had strung these videos together so I'd have to watch one after another for over an hour.

I got a break from this conditioning only to cook and serve them dinner. Fortunately, "cooking" meant only heating the chili we'd made the first day. I was stoned enough that I don't think I could have handled anything more difficult.

While I served them, Kent and Vince continued to taunt me. Some of the taunting was feigned compliments—things like: "You know, Brianna, you have pretty nice legs. That short skirt really shows them off."

But most of it was about the videos I'd been forced to watch. Vince said, "I'll bet you got some great ideas from watching those videos. Now you'll know how to be a really great cock-sucking sissy."

And Kent chimed in, "And, now you can see how much fun it is to be a sissy for real men. I mean, it doesn't really matter whether you enjoy it. Your pleasure isn't the point. But, once you really accept your role, you're going to love it."

Then Vince pressed me to say what was the best trick I learned for pleasing a man's cock.

"All I learned is that you guys are fucking assholes!"

"Hmmm," Kent shot back. "Fucking assholes! Interesting idea, Brianna. Thanks for the suggestion."

This stupid pun cracked them both up.

After dinner, they decided that I needed a refresher course so I had to watch these videos for another half hour or so, until my tormentors had consumed enough beer and pot that they were ready to use me as they'd planned.

"Hey, Brianna," Kent shouted. "We think you've had enough training. It's time to show us what you've learned."

"You've done a good job, Brianna," Vince began. "We're happy to see how much pleasure you get from sucking our cocks and swallowing our cum." (How much pleasure I got was exactly zero, which both of them knew full well. But that didn't stop them.) "You know, though, if you really want to be a real girl, you need to go deeper."

Kent picked up. "Real girls don't just suck cocks and swallow cum. They want to get fucked; they want alpha men's cocks deep in their cunts."

"This is a big step for you, Brianna," Vince continued. (They'd obviously scripted this dialog.) "And we think you need to practice before you take it. So, we have something to help you get up to speed."

With that, Vince produced two very realistic dildos. One was about the size of an average cock; the other was frighteningly large.

"Sit down," Kent gestured toward the ottoman. He took the smaller dildo from Vince, handed it to me, and said, "Start with this one. Suck it like you're making love to it with your mouth. Get it good and wet."

So, there I sat, in front of my two tormentors (formerly friends), sucking on a rubber dildo as if it was a real cock. In one way, this was more embarrassing than sucking these assholes off. At least when I was sucking them off, they weren't watching me dispassionately and with disdain.

"Good," Vince said after a while. "Now, pull it out of your mouth and tell it that you want it to fuck you ... that you need to feel it in your pussy."

"Oh, come on!" I blurted out. "For Christ's sake ... this is fucking ridiculous."

"Do it," Kent said. "It's not a big deal, Brianna. You can do it. Remember all the pictures we have that we can share with the world."

I managed to express to an inanimate piece of silicone that I wanted it to fuck "my pussy". I was right that it was ridiculous. Kent was right that I could do it. And I did.

"Okay, Brianna," Vince instructed, "this is a big step for you. Get on your hands and knees and pull your panties down to your knees. Then lick that beautiful cock that you want so much one more time. Then, press the tip against your asshole, teasing your boipussy. Don't push it in ... not yet ... no matter how much you want that. Just tease your twat."

Masturbating with a dildo in front of them was the most degrading and humiliating thing they'd made me do so far. And that's saying a lot.

Kent continued my instructions, "Now tell it to quit teasing you. Tell it you want it to fuck you—that you need to feel it in your cunt. And, then, press it into your ass. (You can use some of this lube if you want.)"

Again, I was pleading with a piece of plastic to fuck my ass. These guys were sick puppies. I did pause to slather lube on the dildo. There was no way I was going to try this without that.

As I gently pressed the fake cock against my anal sphyncter, I could feel myself open to it. As the head disappeared into my asshole, Kent commented, "Look at her, Vince. Look at her take that hard cock in her cunt. She's loving it."

Ignoring his taunt, I pressed the dildo completely into my ass. I'd done ass play before, both alone and with Nicole. I actually found it pleasurable. Not now, though. Not as part of this degrading abasement in front of my former friends.

At their instruction, I fucked myself with the dildo, at different speeds and to different depths. They also made me moan and say demeaning things: "Oh, God ... I love to feel your hard cock in my tight little pussy;" "Please fuck me harder; I need this;" and shit like that.

As this went on, I saw Vince approach me with the huge dildo. I blanched in fear. There was no way that was going to fit in my ass without tearing me open. Fortunately for me, Vince had other plans.

"Every girl's dream, Brianna, is to take two cocks at the same time, one at each end," he said. Then, turning to Kent, "Isn't that right, Kent? Don't real girls fantasize about being spit-roasted?"

"They sure do, Vince. And Brianna is doing such a wonderful job that she deserves to have her fantasies realized."

Vince said, "Let's do this right, though. Brianna, you can stop that for a moment. Take that cock out of your cunt and go clean it off. Then hustle right back here to make your fantasy a reality."

When I came back, I saw that they'd fastened the big dildo to one side of a doorway, a few feet up from the bottom. Vince took the smaller dildo from me and mounted it opposite the huge one.

"There you go, Brianna," Vince said. "Your dream is ready to become a reality. Now get down and show those two cocks what a real girl can do to please two hard cocks at once."

So, to their commands, I impaled myself from both ends—the large dildo more than filling my mouth while the smaller one penetrated my ass—moving back and forth so that I would "please both cocks, as I was instructed to do.

When they tired of watching me spitroast myself, Kent told me that I had one more task before the pièce de résistance. I knew what that would be so, in a strange way, I welcomed the delay—until I found what it was.

"Now that you've got that big cock all excited and wet, you need to satisfy it. And I know just how you can do that."

Kent got up and picked out a big pot from the kitchen. Putting it upside down on the floor, he pulled the monster dildo off of the door jam and stuck it to the top of the pot.

"Now, Brianna, you'll want to lube that big cock up real good before you sit on it. Right?"

"You're kidding," I protested. "There's no way that thing will fit in my ass." He wasn't kidding, of course. And he insisted that I'd find a way to fit it in my ass or I'd be sorry.

The smaller—well, normal human-sized—dildo had stretched me out some. Maybe I could do this without severe damage. I lubed up the dildo really well and, squatting down over the pot and lining it up with my asshole, I began lowering myself onto the huge phallus.

At first it seemed that there was no way it could fit. It was like pushing where there was no opening. But then I felt my asshole begin to yield. It opened to admit just the tip of the dildo. But, once that was in, it was just a matter of pressing down, slowly, to get the whole thing in me.

It took a few minutes of sliding down and up, each time trying to go a little lower, before I could feel the fake balls pressing against my bottom. I'd taken the whole thing and it hurt, a lot, but I didn't die.

"God! Look at her," Vince cheered. "She's taking the whole thing."

"She's a certifiable cock slut, to be sure," Kent chimed in. Then, turning to me, he added, "Good girl! Now bounce on it so that your little caged clitty flops uselessly. You know, now, that your pleasure doesn't come from your cock; it comes from your boipussy pleasing a huge cock."

Though my ass had opened to accommodate the huge dildo, I couldn't really bounce up and down on it quickly. That still hurt too much. But I did what I could and I made my dick flop up and down to the rhythm, just like so many of the sissies did in the videos I'd been force fed all day.

Both of my tormentors were encouraging me to have a sissygasm. But all of their vile taunts were to no effect. Despite the pressure the dildo was exerting against my prostate, I felt no orgasm building. Eventually, they gave up their hope of forcing me to have a sissygasm.

Vince thought it was time to change from a spectator to a participant. I was allowed to get off the phallus I'd been impaling myself on and was instructed to crawl over to him and service his cock with my mouth.

As the dildo slipped from my sphincter, I felt a sensation of emptiness. It was a relief to feel my asshole no longer being stretched to its limit, of course. But I was surprised that I also felt somehow deprived.

As I was on my knees, sucking Vince's cock, I tried to remember how many times I'd done this in just the last couple of days. I couldn't. Everything was blurred together in my mind. Being stoned and a little drunk does that to you. Maybe it was a blessing that I wasn't completely sober throughout all of this. A foggy mind was a blessing. Unfortunately, I wasn't so stoned that I didn't realize that the worst still lay ahead of me.