The Teamviewer Mature Files

"Yes, Mistress." With shaking fingers, I grabbed some out of my desk drawer.

"Good, now chant after me: No more male panties. No more male panties. Cut them up while you chant."

Shit! The scissors had been left right there on the table.

"That's a girl."

I started cutting up my jockey shorts while chanting like an idiot drone to her will. Maybe after we'd done about everything embarrassing, maybe she'd let me go and I could get on with my life. The male "panties" were soon bits of cloth at my feet.

"Now, hold your balls up so I can tell how big they are. Oh, God, is that all? Can you even get a girl pregnant? Look at that little dick and useless bag of white-trash, slave-making sperm. Do you have a ruler? Put a ruler up against your body so I can see how big a white boy's dick is? I heard they were small, but I can't believe it."

Oh fuck! I had a ruler in my desk, too. I did as she suggested, even when she asked me to turn this way and that, and to put my dick right up near the camera, while holding it alongside the ruler.

"Two and a half inches? Really?"

"It's not really erect, Mistress," I tried.

"Probably because you're been playing with it, too much. No wonder. You have a white boy attitude, sissybitch. White privilege, we call it, down here on my side of town."

"Yes, Mistress. Sorry, Mistress."

"Alright, well, good thing I bought you the smallest chastity device available. You might as well use the smallest ring, too. The worst that can happen is you lose circulation and it all falls off." She laughed. "You'll not even notice."

The ring was only an inch and a half, inside diameter. I didn't have a clue how it fit.

"Push one ball through, then the other. Then bend your dick and push it through."

I did as she suggested, and it was super hard to do because I literally felt each testicle pinch through, one at a time. By the time I got to the dick part, I'd grown a three and a half inch erection, making that a little harder. With a serious strain, I finally got it all through then adjusted the skin so the ring was snug up against my body. The ring felt too tight, and if I moved it reminded me that it was there. Also, there were other parts, suggesting they might compress it tighter.

"Excellent. Now, you have some lube in that one box, I noticed. Lub up your useless dick a little. There you go. Now, put some on the little tube in the middle of the chastity cage. Good. You'll need the small spacer, since your balls are so tiny and we need it tight. Good sissybitch."

Oh, hell. I had it all prepped, and was holding it in my right hand, with my dick in the other. Was I really going to do this thing? I looked at the lock, on the table before me. It had two tiny little keys, though the lock looked like a solid one, and the keys pretty facetted, meaning the lock wasn't a cheap thing. On the other hand, those keys looked a lot like a couple I had on a lock in my bottom drawer. I could switch them, if she asked me to send some keys. She'd never know.

"Are you ready to fuck your little pee-pee with that thing and end up all frustrated and miserable for your mistress? This will be like real torture, won't it bitch?"

"Yes, Mistress. I'm ready, Mistress." All the while, I dreaded having to shove that central pipe up my pee hole, even if I did have a plan to rid myself of it later, when she was no longer that interested in the new guy. I'd have the right keys, and she'd have the useless ones, none the wiser. Still, the pipe part of the pathetically short, two-inch long chastity cage was almost a whole inch longer than the cage, itself. I'd end up impaled clear past the ring around my balls, inside my body. Was it even safe? The impaling end of the hollow tube even bulged out some, like a bead. Was putting that so far in me even sterile? With it in me, my dick would have maybe a tad over a half inch of space around the impaler before it abutted the ring, where they coincided up against my body. That seemed really tight, even if I did have a tiny white-boy penis.

"Put it in. I'm about to have an orgasm, just watching you do that to yourself." She had one hand in her crotch.

Oh fuck. I aligned the impaler and because of all the lube, it didn't even hesitate when I pushed it into my pee hole. God, that felt strange. But, I could stand it. The lube helped, a lot. I pushed it in an inch, feeling it start to resist. I had to pull it back out."

"That's it, fuck yourself with it a little. More lube, sissybitch. Work it in. You can do it."

"Maybe I—"

"You're not going to disappoint me, are you. I'd have to find something else to fuck your pee hole with. Something fatter. I can go buy it, right now."

"I'm sorry, Mistress." I squeezed more lube on the thing. "Here I go." It went in more smoothly with more lube. I didn't feel as much resistance then, as it moved to the ring, I could feel my whole dick back there, like someone was squeezing it tight around and inside the ring. Finally, the slightly wider portion of the tube slipped past the ring and I had to align the pins on the ring so the device holes lined up. After a couple tries, the pins slid through, including the bigger central one, where a smaller hole near my body awaited the lock.

"Oh, there you go. No more penis time for you, sissybitch. Now, put the lock through the hole and snap it on."

This was pretty erotic, in a way. I picked up the lock. I threaded it through, and after a breath of air, snapped it locked. Clink!

"That's a girl. Now, no more penis for you, like god intended for all the girls. We can expect a much more enlightened attitude from whitey, I should think. I will probably have to arrange a kind of conjugal visit, for when I decide you've earned some penis time. Or maybe not. We'll see."

"Yes, Mistress," I said. I shifted a little, and the probe in my dick was almost overwhelmingly debilitating. How did a person stand it? The impossibly small cage around my cock was one thing, but the probe was absolute torture, like someone was sticking her finger up my dick and every time I moved, wiggling it around in my groin, particularly near the ring. I felt like I was peeing, constantly. If I had to hold it in, could I? Seriously, I felt like I was being raped by an unwanted intruder, no matter how I moved. I even sensed some air up there inside. I couldn't stand five minutes of this.

"We should try one of the keys, just to be safe," she said.

"Thank God," I let slip, as I picked up the keys and slid one into the lock. I tried twisting it, but nothing happened. I tried the other one. I turned it over and it didn't even go in, so that wasn't the problem. I tried to put it in a little, halfway, most of the way, and turn it. I tried forcing it a little, but that wasn't the problem.

Damn, if I wasn't stuck in this. Maybe I just didn't know how the lock worked? Maybe I had to push it closed more to get the key to engage. That didn't work because it was all the way closed already. The chastity device was solid stainless steel, for crying out loud. The bars were thicker than the openings between them. I'd need a toothpick to even touch myself.

If I got an erection, I'd be out of room, more than an inch short. In fact, I was getting one, and already felt the pressure. As it moved, the bead at the end of the rod inside of me fucked my hole. My dick and balls seemed to pull out from my flesh because there was nowhere for everything to fit inside the cage. I'd never seen my junk out like that before. The pressure was only worse and from every piece of my package. I wondered if I could even lose the erection, this way. Would I lose circulation, so constrained? The idea of my dick dying and falling off no longer seemed remote. It'd likely happen in my sleep, when I wasn't paying attention for hours on end.

"Good. I needed to check. I paid special to have them send me the right keys and to just put any old keys in yours. You have to check the keyholder box for that service. It cost us thirty extra dollars, but it was worth it, just watching your face, sissybitch, and you saved that much on this month's credit interest, alone. I got it all on video, too, so I can watch it over and over. I think you almost turned a shade of green there, for a minute. That's priceless." She started giggling, and almost fell off her chair.

"Shit!"

"It was so... worth it." She tried to compose herself.

"Fuck me, Mistress." I tried to steady my breathing. "I don't think I can stand it. How long do I have to keep it on?"

She didn't answer me. "Women have their periods and put things up inside, all the time."

"I'm serious... Mistress."

"You'll adjust."

"Adjust? It's pulling hair, Mistress. The thing is so tight it's pulling my pubic hairs."

"Glad you mentioned that, but before we do, look in the bottom of that box over there from Amazon. I think the blue-tooth camera is inside."

Teamviewer Femdom File

By jo199

Chapter Four.

I found myself shaving my chest and legs under the mist of a hot shower and the prying eyeball of a portable camera bluetoothed to the computer. She'd been most insistent that I leave a landing patch of hair just over my penis. She'd given me the option of a triangle or a rectangular, "As long as it's neat and big enough for anyone to take notice, should they catch you out of your panties."

I gasped. "What if someone should see me with no hair?" I'd asked. "A date would—"

"Let me worry about your hookups, boy. I decide who you get on with, and who you don't, from now on. You don't want to get a reputation as a loose slut, anyway. A girl has to think about her reputation. In fact, I'm kind of insulted. Aren't I your girlfriend?"

I realized it was a moot point until this settled down. She was right; dating at the moment would just be way too much. And, people got tired of things. I was betting she'd tire of me in a couple more days. "Yes, ma'am."

So I went into the bathroom and did as she asked. Once started, there was no way I could shave without shaving everything down as tightly as possible. Otherwise I'd itch. The Nair burned, but by that time there wasn't much hair for it to dissolve. I showered the last of my hair off and dried before going back to my room.

"Aren't you sweet. Much better, Joe," Linda said from the computer screen. "Put on the hoop earrings."

One pair had screw-on, so I fumbled around until they dangled.

"Now, adorn yourself with some panties and a bra and go stand with your nose in the corner of the living room. Wait! Don't forget to turn the speaker up and bring your little camera, so I can check on you from time to time during my day."

"During your day?" I strained, putting on the panties.

"Do I look like I'm not busy?" She spread her arms, displaying all the flowers scattered and arranged on tables.

I started hooking the bra in front, then twisting it around to reach into the shoulder straps. "But—"

"Get, bitch. I want you in the corner, like I told you, or else bad things are going to happen!" She put her fists on her plump hips and glared, leaning into the camera. Once so close that I couldn't see her hands anymore, my bank account records came up in a tiny window over to the side.

"I'm sorry for being slow. I'm getting right to it, Mistress." I grabbed the blue-tooth camera and plugged it into a wall socket before plopping it onto a side table. I'm not even sure if it was adjusted right to catch my whole body, but I aimed it in the general direction. In a second, I was standing in the corner with my nose up tight,

"Hands on your hips."

Shit.

"Pinky fingers pointed out!"

Shit.

"Now wiggle your little male pussy if you feel yourself stiffening up, Joe. I don't want you passing out like those soldiers do when they're made to stand at attention too long. See how nice I am?"

"Yes, Mistress," I yelled so maybe she could hear it in the computer speaker a room away.

"Now, sing the words I taught you, slut!" boomed on the speakers that were turned way up.

Shit. "I'm a little sissy maid, cock sucking money pig," I had to sing sixteen lines of that. She'd taught me to sing it to the tune of Little Teapot.

"Louder. I can't hear you."

I sang louder.

"Try your sissy voice!"

I had to almost scream in a cappella.

"You only have to sing and sway your pussy every fifteen minutes, Joe. I don't want you to get hoarse."

I had to count off the minutes in sixty second bites: sixty seconds, sixty seconds, until ten minutes. When I went over to eleven, she yelled, "That's thirty more minutes in the corner for being late." Shoot. I found myself singing, "I'm a little sissy maid, cock sucking money pig," every five minutes, just to be sure.

"Sway those hips while you sing, bitch!"

"Sorry, Mistress. "I'm a little sissy maid, cock sucking money pig...."

"Thirty more minutes. I don't see those pinky fingers up."

"Thirty minutes more added to what?" I mumbled so low I was sure she couldn't hear it. I kept my hands curled, except for the pinky fingers, both of which felt like they were going to fall off.

After a minute she added. "Let me help. I'll let you keep your fingers together, as long as you have them open, palms facing the floor. Elbows rigid. Swing that pussy when you're like that. Otherwise, pinky finger while standing still. That's better. Like a little sissy."

I tried facing my palms parallel to the floor and wiggling. It was stupid, so I went back to standing still with my pinky fingers sticking out. Once, I got confused and didn't wiggle my ass while singing.

"Another thirty minutes, sissy."

After that I tried to keep it straight. Wiggling my ass was the important thing. Sometimes I did that even when I wasn't required, mostly out of paranoia.

###

"Gee, Sissybitch, you have a fairly nice business going there," she said the next day. I'd just finished affixing the last of ten blue-toothed cameras to their mounts, as she'd instructed from the floor plan. Them and the expansion router had come in yesterday afternoon. I did this while only wearing panties and a bra because she'd decided to give me a break from a dress for the morning.

I leaned toward the microphone and hit respond. "Thank you, Mistress."

"I want to hire your services. I have a business, too, you know."

"Well, uh—"

"Don't you think black people can have businesses, Sissybitch?"

"No, Mistress, or I mean, of course black people—"

"Or is it women who can't own successful businesses, in your mind?"

"Of course women can have businesses. Two of my clients are women, Mistress Linda."

"Good. I'll start feeding you the particulars on my lawn care business right away. Soon as you get that started I can demote the accountant doing that one."

Ten minutes later, the whole wad downloaded. I had books for twenty-seven trucks, two cars, forty full-time employees, a few part-timers. Healthcare, tax pipelines, client billing; it was extensive. Usually a company like that had more than one bookkeeper on staff. It'd tax that person just to feed me the right data in a timely fashion. Even scheduling seemed an accounting function, I noticed. Did they even have managers? Well, yeah, but mostly rolling, and apparently one or two guys who drank a lot of coffee (my guess).

It looked like they were on the edge of being illegal because of plain sloppiness. The company worked out of a small warehouse two cities over. It was going to take me an eighty hour week just to park all the data into databases that had a prayer of allowing me to keep track of it.

I sent Mistress Linda a note saying it'd be a month before I could pick it up fulltime, and even then they'd need to run parallel with the old accounting firm before we turned the switch. I sent that alongside a quote for services. It was five figures a month.

She sent a note back. "No problem. I'll make sure they pay the figure and I know the process of sending the data. Those suggestions for the bookkeeper are also helpful. They'll toe the line for you, sissybitch.

I was in the process of sending another note back when she came online. "I'll have to contact them directly, Mistress. Maybe several times a week."

"Fine. I'll set it up. Use this number." She sent one via messenger. "Just tell them you are sissybitch. They already have your number."

I sat there in my panties, stunned.

"Shouldn't I use the name Joe for professional contacts?"

"Oh, that's right. Joe then. And, I have two more companies like that, followed by my own, of course."

"I can't handle all that work, Mistress Linda?"

"No problem. We'll set one up per month. By then you'll have more capacity. I'll make sure you get what you need. A bigger server, a couple stations. I know a computer guy."

"A computer guy?"

"One of my sluts. He already said you'd do better with a higher capacity line. Get this going, and let him do the work. He's one of mine, anyway. Everything's free for me."

Free? "Free?"

"Soon as you get this company all set to go and do a day's work without that other firm, we'll see what we can do about that chastity, sissybitch." She leaned into the camera shot and in the process showed considerable cleavage.

What in hell was going on? Well, at least I was getting a big client. And the dick-piercing chastity thing off. A client as big as this one nearly doubled my income. Maybe this disaster was about to turn? "Alright, Mistress," I said.

"Good. I told the computer guy to get his ass over there tomorrow morning, five o'clock, sharp. He will be decking the place out with a little office furniture, a server, four desktops, as well as meeting with the provider for more capacity. Shoot, sissybitch, I'm doing all the work for you."

Something wasn't right. I had to type it; I couldn't speak for the sake of a sense of dread: Yes, Mistress.

"In the meantime, clear out a room. This one's good. The family room and the other spare bedroom, too. Just empty them, for now. I have a dumpster being delivered later this afternoon."

"Empty them?"

"Use your discretion. You might want to move things around, but yes, most of the stuff will have to go. I'm remodeling for your new business, sissybitch. You can't stay small forever. I'm bringing you three new clients. Say thank you for making something out of you other than the small-time vision you had last week."

"Thank you." I think I breathed the words rather than said them. Up till then my business had been comfortably just right for me. I suppose I could have been bigger, but I was just one guy. I bit off what I could manage. How would I manage three times the workload? These new businesses didn't seem tiny.

"If you took the two side tables and chairs out of your bedroom, you could fit two dressers and another small bed in there, in case of guests. You don't need so many bedrooms. You can eat in the kitchen, and still have the living room free for TV and this computer desk. And, that basement is a mess. By all means, don't add anything to that. In fact, with the dumpster there, I suggest cleaning out at least a third of that junk, too. You have all night. A clean house is a clean slave."

I'd never heard that saying before.

I typed, hoping to get something on record: If my business expands, I'll maybe just get a bigger house and better furniture.

"I think that's a wonderful idea, sissybitch. We're working on it. I'm with you one-hundred percent of the way."

I had a brainstorm, just then. I said, "I'll be too big. I'll need an assistant or two. I can't dress and act like we're doing with others in the house. This slave arrangement is going to become impractical for us both."

It was my way out, finally. She'd see sense in it, now that she wanted me to do her books instead of playing S&M bullshit like we were. The incentive to make better money with a capable accounting and consultation firm in hand would change the balance entirely in my favor, finally!!! She'd forget everything we'd been doing entirely. I had the ace. I'd stumbled on it like the goodie godmother had hit me with her wand.