Day 100

by: Ms. Finch

Arriving home from work on Friday the 13th, my twenty-first day of servitude, I set about my “pre-dinner” preparations as Mistress had prescribed, comfortably excited over the prospect of another evening of “sissy-slave training” at the hands of my Internet Mistress.

I’d met Mistress online over three months previously, and we’d had the most erotically charged online relationship I’d ever thought possible. At her behest (and my own longing, I confess), I’d worked hard to develop the rituals – and to build the training devices – that had thoroughly dominated my last 99 evenings of “training.” Particularly joyful to me was my knowledge that Mistress was not a professional dominatrix, but rather, was a woman who genuinely enjoyed the feminization and domination of men that she found stimulating – men like me.

Stripping off my office attire, I peed and hastily douched my “ass-pussy,” as Mistress had me referring to my asshole, then stepped quickly into the shower, where I’d ritualistically shaved off every hair below my moderately-plucked eyebrows for the last 99 evenings. Once again, I smoothed the shaving gel over my body, shaving off every trace of the hateful hair of masculinity that Mistress had convinced me to remove.

Emerging from the shower, I toweled off briskly – Mistress didn’t believe in pampering slaves with long scented baths and body oils – and dressed in my “dinner uniform.” My dinner uniform consisted of a tight black corset with push-up breast cups, fishnet stockings that attached directly to the corset with four garters, a pair of killer 6″ black pumps with ankle straps, my blond ringlet wig, long red press-on nails, and a full course of long-wear makeup.

Mistress had required me to study half a dozen makeup books and get myself color-printed even before my first day of “official training.” I had never kept the makeup on for more than 4 hours, so I wasn’t sure why Mistress insisted on the long-wear stuff, but as the saying goes, “mine is not to reason why…” My last act was to generously lubricate my ass-pussy and coat my lips with ointment: both ends would need the protection.

Fully dressed for dinner, I walked over to “the training machine,” as I called it, a machine that I’d built to Mistress’ exacting specifications. First, I took the package that Mistress had sent to me, and, removing six numbered opaque plastic bottles, upended the first four into matching receptacles at the front of the machine and the last two bottles into receptacles at the back of the machine.

Then, climbing onto the long axis of the machine’s rectangular platform, I dropped to my hands and knees, draping my corseted waist across the small leather saddle that fit perfectly into the curved front of my corset. As my hands passed through two four-inch circles in the false floor of the platform, coming to rest on the penis-shaped grips below, I felt restraining belts inflate around my wrists, and automatically flip across my calves and back, pinning me firmly into place. I heard the screen and speakers activate as my triggering of the machine alerted Mistress of my “on duty” status, and the two, life-size dildos mounted at the front and rear of the machine moved forward on their own magnetically controlled tracks, stopping when they were poised a few millimeters from my lips and ass-pussy. In that position, I awaited my Mistress’ presence, my eyes fixed on the screen, eight inches in front of me. The two screens on either side of my head showed a relaxing screen-saver pattern as I waited. I didn’t wait long.

“Well slave, I see you’re ready for din-din! I bet you’re wondering what I’ve sent you tonight, hmmm? Before I tell you though, let’s set tonight’s “feeding depth,” shall we?” Mistress could “see” me because there were videocams set up in front of me, behind me, and on both sides, that she could redirect or control, as she could nearly all of the mechanisms in the training machine.

I heard Mistress click a switch on her computer, and instantly, the dildo poised at my lips slid forward about six inches, the restraining bar dropping behind my head, forbidding any backward motion. Mistress pushed another few buttons, and I felt the rough entrance of the ass-fucker as well. I estimated she’d given me only about 4 inches of the “12 inch monster” as I called it, but that was quite enough for me, thank you.

“Now, before I start dinner, let’s make sure you know the emergency procedure to release yourself. Go ahead and test it.”

I quickly gave the dildo in my left hand two twists backward, then gave the one in my right hand two twists forward, feeling the pneumatic bands relax instantly. Without waiting to be told, I restored the handgrips to the regular position restoring the bands to their previous level of snugness.

“Well, my little sissy, I hope you’re comfortable, because you’re in for some interesting training tonight. It is Friday the 13th, after all.”

Mistress’ keys danced over the keyboard, and I felt a searing pain in my backside as she sent the ass-fucker slamming to its full length, for the very first time. I’d have screamed, except that the sent the face-fucker into the base of my throat at the same time, the false patch of pubic hair at the root of the life-size dildo pressed into my nose.

I was terrified, as my breathing was blocked, and the pain in my ass was like nothing I’d ever known. I’d already started the emergency release sequence before I was even aware of it, but her disapproving tone stopped me as the ass-fucker pulled back half way and the face-fucker pulled back enough to let me breath.

“Now sissy, I was just teasing you! Here, let’s start your dinner flowing, it’ll calm you down.”

She reactivated the face-fucker, and it started doing its thing, sliding back and forth, into my throat, and back leaving two inches in my mouth even at the shallow end of the stroke. I knew what to expect, and after a few minutes, I felt “dinner” pulsing out of the end of the face-fucker, at variable depths. Mistress said it was important to know how to “live off of cock pudding” for a slave like me.

“Tonight’s dinner is very special. The first course, that is now sliding down your throat is the usual blend of weight-loss powder and skim milk, with enough xantham gum to give it that nice cummy texture. By the way, this might be a good time to tell you that I’ve been spiking your first course with rohypnol since the first night, though I held it back until tonight’s second course, so we could have this chat while you are fully aware of what’s going on. You’ve been up to a hypnotic dose for two months now, which might explain why you haven’t noticed a few other things I’ve done to you.”

I realized that she’d activated the monster in my ass-pussy again, and it was sliding in and out of me, hitting bottom each time. I felt a strange pulsing from back there, too. She must have seen my eyebrows rise in surprise.

“Yes sissy, the twelve-inch monster has been doing you at full depth for two months now, and you’ve never noticed, other than to cum harder every night. It only hurt you tonight because I usually work it in over a few minutes, after the rohypnol relaxes you. The bottle behind you, that the ass-fucker pumps from is not simply lubricant, by the way, it’s a blend of the most powerful female hormones available, as it has been since the first day you began machine training. If I hadn’t been programming you through the rohypnol, you’d undoubtedly have noticed the breasts you’ve grown. Others have noticed, I assure you.”

I’d been starting on the emergency escape sequence from the first mention of the word rohypnol – I knew what that drug could do, why it was called the “date-rape drug” with good reason. But no matter how I twisted the cocks in my hands, nothing happened! I heard her giggling come through the speakers as she confirmed that she’d had me put an over-ride on the escape mechanism after my very first dose of the rohypnol.

“Now sissy, while you suck down your first bottle of dinner, I’ll let you watch this nice video montage, made by my other slaves, a cocksuckers-eye view of the world, so to speak.” I’ll come back to you when you’ve downed your first bottle.

I saw the screens clear around me, and I realized I was seeing footage of a man’s pubic mound moving toward me and away from me in time with the face-fucker, as if I were sucking the man’s cock. It was very realistic, and very hypnotic. The side monitors were synchronized along with it, presenting a 3-d realism that was astounding. It took half an hour for the first bottle to empty itself down my throat, by which time I’d seen a dozen different cocks sliding into and out of my own mouth. I’d swear that I could even smell the musk in the men’s pubic hair!

Mistress’ voice returned. “Well, sissy, I hope you enjoyed your first course! Tonight’s second course is very special indeed! A good friend of mine works at the local sperm bank, and it just so happens that they go through their samples every day, and dispose of the ones over a month old. There’s nothing wrong with them, really, they’re just not as reliable for impregnating women. I had her save up the last few month’s worth, just for you, sissy. That’s what is in the second bottle. And the third. And the fourth. And the one about to unload itself into your ass.” She laughed as she saw me struggling, and as tears of frustration started to flow down my cheeks, having no effect on my waterproof makeup.”

“Have you had time to remember the fun you had after you slipped rohypnol to my sister last year? You really shouldn’t have messed with my sister as you did, but you should NEVER have left her alone afterward in your unlocked dorm room. Do you know how many men fucked her that night, in her mouth, her pussy, her ass? Dozens. Maybe hundreds. And they took pictures, and movies. The humiliation was so great, she tried to kill herself. She’s locked up now, getting therapy. She may recover in a few years, or so the Doctors say. You won’t be so lucky.”

Her fingers started a new video montage series, and I realized I was watching myself, being fucked from front and back, but she’d put video footage in place to make it look like I was really sucking cock, and being fucked from behind. I didn’t quite understand it, but I realized that my video image had breasts! Very large breasts!

“That’s right, sissy, you’ve got breasts. 40DD, to be precise. You’re wondering how you could miss them all this time, aren’t you? Well sissy, you haven’t really been going to your old office job. You quit that two months ago. You’ve been working for a friend of mine doing office work – dressed as a woman – ever since. You’re quite good at typing, filing, and making coffee, but you’re even better at sitting prettily at a desk, filing your nails, touching up your makeup, and reading women’s magazines.”

Her words were matched by more video footage of me working, as a sexy secretary. I could see my breasts growing as the video approached the present, but there was a huge jump in the middle, when I’d obviously been given breast implants. And, I noticed other changes as well. After what looked like two weeks on the job, my lips seemed strangely plump beneath my lipstick. I realized that they’d been injected with collagen for that bee-sting look. My eyebrows had almost disappeared, leaving only a fine, dark arch high above my carefully made-up eyes. My ears were pierced, with several heavy, bangle earrings dangling from both earlobes, and my blond hair…wait a minute! I’m not blond…and that’s not a wig!

“Ah, you finally noticed the hair, I wondered how long that would take. That’s right sissy, you’re a blond, a nice, sexy blond, and that’s your very own hair, bleached, permed, and curled. The hormones made it grow nice and full, and fast. You’re the envy of half the women at the salon, where you go every week for a nail and hair touchup. The rest of your cosmetics, by the way, are permanent. Tatoos and electrolysis, the wonder of modern technology”

I felt tears rolling down my cheeks as my body was filled with sperm from each end. “Watching your transformation has improved my sister’s state of mind considerably, sissy. And I have other plans to help that along. She’s going to watch your life destroyed, as you nearly destroyed hers.

I’ve already planted videocameras in the homes of your family and friends, so I’ll be able to film the expressions on their faces when they view these videotapes of your transformation. While you were under the rohypnol, you signed over everything you have to me, and agreed to give me a binding power of attorney, which is how I got the court order to change your legal identity to your new, lovely feminine self. There’s only one last thing to take care of, and then, you’ll never see me again. I’ll tell you about that after you’ve finished all your bottled sperm, asshole.”

For the next two hours, I knelt there, on all fours, sucking, being fucked, and above all, swallowing…mouthful after mouthful of sperm, literally, two gallons, one squirt at a time. My bladder emptied itself, and I realized that my penis was pointed over a drainage tube, and that I must have done that before. The realization of how much I had been brainwashed brought fresh tears to my eyes.

“Well sissy, I see you’re nearly finished! Well, I’m going to offer you one last chance at redemption. While you finished those last bottles, some men have entered your apartment, and are about to carry the training machine out to a nice club where you can experience the same gang-bang treatment you gave my sister. I’m afraid that you’ll need some surgery to put your butt back together after that, but that’s okay, you’d be having surgery down there sooner or later anyway. So, before they unplug the training machine…your last chance at redemption. You’re already addicted to the rohypnol, and I’ve already implanted a new persona for you via the training machine. Your choice is this: if you want to avoid having your friends, relatives and co-workers see all this, if you’d rather just “disappear” and be presumed dead in a few years, you can use the “emergency release” sequence on the training machine one last time. It will flood your body with a huge dose of the rohypnol, and administer enough electroshock to your brain to terminate your primary personality completely. What will be left behind will be a very dumb, very fluffy bimbo, who works as a secretary by day, and a hooker by night. Now, make your last free choice, you fucker, and then live with it!”

I just knew I couldn’t live with my entire family seeing what had been done to me. Psychic suicide seemed the best way out….the only way out. I twisted on the dildos, one last time.

“Hello, Hotsex productions. Yes Ma’am, we did produce “Payback is a Bitch, the Destruction of Don. Did you want to order a set? I’m sorry Ma’am? You said you’re his mother, and you want to know where he is? You got a copy of the tape in the mail? I’m sorry Ma’am, I can’t help you, I’m only the receptionist. I could put you through to Ms. Johnson, the president of the company, Ma’am…oh, you’ve spoken to her already? Well, have a good day, Mom, I have to get ready for my night job. I’m a hooker, you know. Oh, I’m not supposed to admit that, am I? I’m so forgetful these days.” Did I say Mom? Oh, I meant Ma’am, of course. I have to go now, my boss gets so angry if I don’t bring in enough money…bye bye!

The End

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