Anal Chastity

"I want to feel you bare in my ass next time." Bob proposes.

"Oh? And what are we going to do if you win?" You tease.

"Oh! Uh..., I meant I want to be bare in your ass next time." He sheepishly adds.

"Well, I want something too," You say, "I think the loser should have to wear a chastity cage until the next game."

"What? But we didn't order one!"

"Let's do it now," You reason. Bob doesn't seem happy, but he doesn't appear to be confident enough to challenge you.

The next day, delivery rings the doorbell around 4pm. You unpack the device and set it on the table before you as you start the game. It looks so small, you think, I don't think it would even fit me if I lost.

Fortunately, you don't have to worry about that. It's pretty obvious Bob isn't trying at all, only pretending to complete your ritual. Nothing comes out of your dick as you win, your testes having been drained dry by a month of orgasms. Your friend doesn't even notice, and when you inform him he doesn't bother arguing, just continuing to wank his half-hard penis.

"Put a little more effort into it," You tease, "Who knows when I'll let you cum again?"

Immediately, he's fully erect, and five seconds later he's orgasming.

"Good girl. Now that you're soft, we can fit your little clitty in its new home." You worry that he's going to get hard again, but thankfully he just quietly sits there while you place his best friend in prison.

"I think you need a new name now," You muse.

"What?"

"Yeah, I mean the Bob I know doesn't dress up like a girl, and he certainly doesn't let his best friend lock his cock away. No, you need a new name for your girly side. I know - Brittany! We'll call you Brittany from now on." He's obviously uncomfortable, but he doesn't complain.

At night, you hold the key to Bob's (no - Brittany's) manhood up in the light as you once again find yourself wondering about your relationship. A month ago Bob was your tough guy best friend, now he was willingly letting you lock him in a chastity cage. Are you guys in a relationship now? Is he your boyfriend? Or is she your girlfriend? You think back to yesterday, when you held his face in your arms. 'I'm just glad you're happy', he had said. It's enough to get you hard again, but you don't touch yourself. Instead, you ask why you didn't kiss him. Should I have? Did he want me to?

You're about to head over to Bob's for your reward, when he sends you a text:

• :( Looks like we're gonna have to postpone until later. Mom just called. She's coming back tomorrow. I need to clean -

You type your response without thinking:

• I'll come over and help. We'll do it twice as fast :) -

You can't help but feel depressed when you put your phone down. Soon, your amazing summer will be cut short. What does this mean for you and Bob? Are you just going to try and forget everything that happened? You push the tear-inducing thoughts from your mind. Tomorrow you will answer these questions; tonight you will ignore them completely.

Bob is all dressed up as he opens the door. "Thanks for coming!" The relief on his face is evident.

"Hi Brittany, why are you dressed up already? I think we should do the work first..."

"Oh, no, that wasn't my intent." Another cute blush creeps up under his mascara. "I just figured I'd make it worth it for you. You know, seeing how you're coming here to help and all, I figured you'd want to see me in the clothes cause you find it exciting or something and I just wanted to make it worth it for you and.... If you don't want it, I can take if off!" He exclaims with a worried look.

You assure him that everything is fine as you get to work. You start upstairs with the bedroom, splitting the work so that you are vaccuming while Bob dusts. With the feather duster in hand, Brittany kinda looks like a maid. Forcing the dirty fantasy from your mind, you get back to work.

Quickly, you make your way through the rooms, using your teamwork to your advantage. In the master bedroom, you move the furniture so that Brittany will be able to dust behind it while you wipe all the glass.

An hour later, you're finished with the second floor and ready to head down to the living room, where things get much more difficult. Despite your protests ('It's 90 fucking degrees outside!'), Bob insists on opening all the windows so that it stinks less from all your smoking. Your shirt is soon off as you start sweating, and you find it harder to concentrate as Brittany's dress sticks tightly to her form. At one point, you nearly drop a vase when you turn around to find her panties showing as she reaches for something beneath a cabinet. When you get up to the couch, you can't help but smile and think back to all the games you played. And all the cum you shot. You kneel down and examine the material, but thankfully you don't find any stains.

Your throat is so dry when you let him (her! I need to stop messing up!) know, that you decide to visit the kitchen for a drink. Grabbing two sodas from the fridge, a dirty thought sneaks in as you find Brittany facing away from you. Sneaking up on her, one beer in each hand, you slip your arms over hers and slam the ice-cold cans into her cheeks.

"AH!" He screams as he jumps up from the shock.

"Gotcha!"

You hand him a drink as the two of you take a small break before moving onto the basement. The basement proves to be the most challenging, with lots of heavy crap that needs to be moved around. Your muscles burn from the effort, the whole room closer to a gym in your mind. Why did we bother moving all this shit in the first place? Bob looks really out of place as his muscles bulge under the dress, but you do your best to ignore it. The whole room stinks of your masculine sweat, and you can tell Brittany finds it arousing.

You decide it's time for another break. You open up a pack of ice cream for yourselves and then soldier on. Brittany turns on the water hose and makes her way around the house, watering every plant her mother planted. Meanwhile, you fire up the lawnmower and criss-cross your way in front of Brittany's house, making sure it looks more or less flat. The scorching heat exhausts you more than the work-out, and as you complete your final turn, you find yourself wiping your forehead every few seconds. The sweat is coming out of your body, making your abs glisten in the sun.

"Whew, all done!" You call, shutting off the engine. "I don't know about you man, but I sure need a shower."

He (She!) nods, and you both take turns under a real shower.