Tormenting Herself for Fun part 2: An Unexpected Visitor

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This is a continuation of my previous story “Tormenting Herself for Fun”. It will probably make a lot more sense if you have read that one first.


Almost two weeks had passed since Maria’s last live stream. The brand on her butt was healing nicely; she would never be able to go out in public wearing a thong without the risk of someone recognizing her, but she would never do that anyway. Her hair had grown out to a rough stubble a few millimeters long. She sat in her office chair naked, working on drawing the schematics for her next project. It was taking longer than expected because she couldn’t stop distracting herself by rubbing her head.

The doorbell rang. Maria figured it must be UPS or Amazon and didn’t bother to answer it. She had been keeping all the blinds in the house closed, and hadn’t worn clothes in the last two weeks, except when she threw on some sleepwear and wig to pick up deliveries or the mail. She didn’t feel like getting dressed at the moment, so she opted to ignore it.

The doorbell rang again.

“Ugh, I guess they need me to sign for something” she rolled her eyes and threw on a bathrobe and sloppily tossed on the silky black wig that sat on a mannequin head beside her.

Maria walked to the door and looked through the peephole. She expected to see an annoyed delivery person, but instead it was a girl with bright pink hair in a floral sundress. Maria opened the door. The girl’s eyes lit up when she saw Maria’s face, as if she was seeing an old friend for the first time in ages.

“Hi, I’m Naomi, it’s great to meet you!” she reached out for a handshake, but shrugged and withdrew when it wasn’t reciprocated.

“I think you have the wrong house” Maria responded.

“No, Maria, I don’t think I do. Although it feels weird to call you that when I’ve always known you as C. Nice wig.” she grinned devilishly.

Maria had always worried this day might come, when someone from the internet found out where she lived and showed up at her door. At least, she thought, it was a girl, and not some creepy dude with a neckbeard and a fedora. She invited the stranger inside to avoid making a scene.

“So, do you want money?” Maria asked.

“No… no” replied Naomi “If I asked you for money I’d just be taking my own money back”.

“Then what do you want” Maria replied, confused.

Naomi leaned over to her and whispered seductively “I want to ride the Demon.”

Maria certainly wasn’t expecting that from her first stalker.

“By the way” Naomi continued “Is the brand real?”

Maria untied her bathrobe and threw to the side, she was naked again. Then she turned around and bent over to give Naomi a view.

“Wow” beamed Naomi “That’s hardcore! Can I feel it?”

Maria allowed her to rub the still-healing brand on her butt cheek. Once she realized that her intruder was here to adore rather than threaten, she had begun to revel in it a bit.

“You are the real deal” praised Naomi “but when I take a ride on the Demon, I’m gonna walk away with my ass still pristine. I can tell you wanted to be branded, the way you dropped the razor and then missed a spot on purpose. You could have easily avoided it.”

Maria wondered whether or not she should be offended. She had legitimately tried to complete the challenge to avoid being branded on the ass, but the goal she set for herself was more difficult than it might seem to someone who hadn’t been in her position.

“Yeah well that’s what you think right now” replied Maria. “By the way, how did you even find me?”

“Oh I’m a software engineer” Naomi responded. “To be exact, I’m an ethical hacker. My day job is hack into systems to make my clients aware of their vulnerabilities before someone less honest than me does it. I have to say, your devices are ingenious. I would expect nothing less from someone with a Ph. D. in electrical engineering from MIT. But your security suuuucks. It took me a couple hours to figure out your name and address.”

Maria was still reluctant to let anyone else into her basement, so she tried to dissuade Naomi. “You know you need to have your nipples and clit pierced in order to hook everything up, right?”

“Not a problem” Naomi responded. She quickly put her purse on the ground, lifted up her sundress and tossed it aside. She wasn’t wearing anything under it. Both of her nipples had the same studs as Maria’s, and her clit had a similarly styled ring. She had tattoos around each nipple in a sunburst design and a mandala design below her large, shapely breasts. Her pubic hair was carefully crafted into a V shape, met at each side by a floral tattoo that wrapped around her hips. “I’ve had the nipple studs for a while. Just got the clit done before I left. You should have seen the TSA guy’s face after I walked through the scanner at the airport this morning.”

“Ok well…” Maria paused while she thought of other things to dissuade her guest. She took off her wig to reveal the nearly bald head underneath. “You do know that it’s basically impossible to avoid having your head shaved, and once you are locked in, there is no way out until the time ends?”

“I’m counting on that” Naomi immediately replied. “I’ve damaged my hair so much with all the times I’ve dyed it. What better way to start fresh.” She reached up to Maria’s scalp and rubbed it, almost purring. “I can’t wait for my head to feel like that. I wish you could strap me in right now, but I know we’ll need some time to hype up the show. It’s Thursday and I’ll be in town until Sunday, so what do you say we run the livestream Saturday night?”

“Well I guess I can’t talk you out of this.” Maria shrugged. “I would suggest you spend the time looking at that cute butt of yours in the mirror, and enjoying the last few days where it won’t be branded with my initial. We’ll split the money 50/50.”

“60/40” Naomi responded. “And I fix the security vulnerability that allowed me to find you in the first place.” Naomi turned around and wiggled her ass at Maria playfully “Stare all you want, because after Saturday night, you’ll still be the only one in this room with an M on your ass.”

Maria took that personally.

The Live Stream

Though it had only been teased on the website for a couple days, the surprise live stream had drawn considerable interest from Maria’s viewers. Site traffic was already high from people downloading the video of Maria’s orgasmic depilation from two weeks prior. Just as before, a preview video was released as the timer to the live stream ticked down. This time, Naomi was tied naked and masked, her hair tied up with a cable that hung from the ceiling and forced her to stand on her toes, and her piercings glittering in both of her nipples and her noticeably swollen clit. Maria’s severed ponytail still hung from the ceiling, taunting Naomi with the fate she was about to endure. Maria donned her familiar Master B costume, though the helmet fit more loosely now that her long, thick hair was gone.

“Ladies and gentlemen, let me introduce you to my next victim!” Master B growled in his synthetically masculine voice. “She thinks that she can ride the Demon without cumming, and she is so arrogant that she is willing to risk not only surrendering that ridiculous pink hair of hers, but surrendering herself to my servitude and wearing my brand for life! This punk slut has a name, for now, but I won’t bother to tell you. After tonight, she will only be known as Slave D. Slave C begged for me to show her mercy, but mercy is not my style, and for that, I will force her to watch as her friend is transformed from a proud whore to a bald, branded slave.”

He held up a red hot brand with the familiar M design.

Naomi had indeed been arrogant. Because she was so sure that Maria had slow rolled and failed on purpose, she had agreed to let Maria make modifications to the conundrum which would increase the difficulty. Not to spoil the surprise, she had allowed Maria to make these modifications without telling her what they were.

The live stream began. Naomi sat locked into the Demon, her arms, legs and thighs held by metal restraints which would not unlock unless the timer ran out. The large dildos were fixed into place inside her pussy and asshole. The vibrating clips were attached to her nipple and clit piercings. Most importantly, the sextet of electric clippers were staged at the back of her neck, threatening to reduce her pink hair to stubble if she couldn’t resist the urge to cum. Maria, or Slave C as she was known to her viewers, was shackled to the floor and ceiling in front of her, naked except for her mask, and a vibrating magic wand tied in place against her clit. She was placed so that one of the cameras would show a clear view of the brand on her ass, proving to any skeptical viewers that it was not fake.

The timer started. Maria was worried that not enough people would tune in to the stream due to the short notice of the announcement, but she quickly realized that she had nothing to fear. The money rolled in from the viewers and the intensity of the vibrations inside of Naomi quickly shot up, from a 3 to a 5 to an 8 and to an 11. Naomi was grinding her hips on the machine, as if she wasn’t even trying to stop herself from cumming. Just after the 3 minute mark, the sensors registered an orgasm and the clippers sprung to life. Naomi screamed triumphantly as they made the way up the back of her neck, bouncing up and down as much as her restraints would allow, in order to prolong the orgasm. As the clippers moved up, some kind of design on Naomi’s scalp became visible. This was a surprise to Maria, and to everyone watching the stream. Clearly, this wouldn’t be Naomi’s first time being bald.

By the time Naomi’s orgasm was over, half her hair was gone. She was shaking, drenched in sweat, as well as other fluids. The tattoo on her scalp was a fractal pattern. Based on the shape of it, nearly the entire area under her hair must have been covered. Maria caught only a glimpse of it from her angle.

Naomi was determined not to make the viewers wait long. As soon as the vibrations started to intensify, she resumed bouncing and grinding on the machine. The intensity was only at a 9 by the time the clippers started up again. Naomi seemed to be pushing her head back against the clippers, like a cat begging for pets from her human. Her screams of pleasure were otherworldly, amplified by Maria simultaneously experiencing an orgasm as she watched. Naomi managed to hold it for an amount of time that didn’t seem humanly possible. Finally, as the last strand of hair was sliced from her head, the pink ponytail flew off and bounced around on its cord before coming to rest above her head. The intricate fractal pattern on her scalp was now almost fully visible, obscured only by a tiny bit of light brown stubble.

Naomi had forced the Demon to shave her head in only 9 minutes. She still had 36 minutes on the clock for the bonus round.

Bonus Round

The compartment in the front part of the Demon popped open to reveal a can of shaving cream, a miniature water bottle, a razor and a small towel, but the shackles around Naomi’s wrists did not release. She could see in Maria’s eyes that she was grinning, but had no idea what the stream viewers could see.

Master B appeared on the stream again.

“Well well, it looks like the bitch didn’t manage to keep her pink hair after all. Those of you who tuned in last time know what’s next. She will have until the time runs out to shave her head completely smooth. If so much as one hair remains at the end, she will be branded. However, since she was so sure that this challenge would be easy, I’ve decided to less of a generous master. I am now putting that can of shaving cream up for sale. If $1000 is donated in the next 5 minutes, I will take it away from her, and she will have to render her head marble-smooth with nothing but a tiny bottle of water and a cheap disposable razor.”

Maria knew that was an easy target when she recorded the clip. When she had been in Naomi’s place, there was no 5 minute period where less than $3,000 was generated. Sure enough, about a minute later, a hole in the bottom of the compartment opened and Naomi could only watch as the shaving cream fell out of reach. Then her wrists were released.

Naomi poured most of the water onto her head and rubbed it into her stubble. without hesitation, she picked up the razor and began to scrape away at it. The way she methodically attacked the short hairs, her right hand pulling the razor while her left hand trailed behind it to check that the skin was smooth, she looked like someone who had done this hundreds of times. This was because she had.

Unbeknownst to Maria, Naomi had kept her head shaved smooth for over two years after she got her scalp tattoo, before letting it grow out again. Even as she screamed out in orgasm, Naomi didn’t even slow down. She had shaved her entire scalp completely smooth and only 21 minutes had gone off the clock. All that remained was her eyebrows, but instead of trying to shave them, she was focused on her next orgasm. Naomi gyrated her hips while pressing down on her clamped clit with one hand and rubbing her smooth scalp with the other. Finally, when she was finished cumming, she poured out the rest of the water onto her fingers, spread it across her eyebrows and reduced them to nothing in a matter of seconds. The clock hit 25 minutes.

Naomi was not free to go, though. Instead of her legs being released, Maria’s shackles popped open.

Master B appeared on the stream again. “Hmm… I see that she has managed to shave herself smooth without the use of shaving cream. Slave C failed to make her own head presentable with more time and resources, so now the punk bitch must show my stupid slave how it’s done. Slave C has let her head grow rough, and now my new submissive must make it as smooth as hers, or she will get the brand.

The cutscene ended. Maria now leaned over Naomi, her head between her breasts. She hadn’t had time to reprogram the image software, so she fidgeted on the side of the machine for a switch she had installed. If Naomi hadn’t full shaved her by the time the clock hit 45 minutes, she would hit the switch to engage the brand.

With no water remaining and only a dull razor, Naomi had to get creative. She reached her hand between Maria’s legs and covered it in the ample moisture, pressing down on the vibrator and inserting two fingers to make Maria moan and release more fluid. It was the first time another person’s fingers had ever been inside of Maria. Naomi then spread the moisture around Maria’s stubbly scalp, and reached between her own legs to gather more fluid.

She scraped at the top of Maria’s scalp with the dull razor while using the other hand to finger her, causing both girls to simultaneously orgasm as the sybian inside of Naomi reached its max setting. As she continued to rub their combined juices into what tiny amount of hair Maria had, she seemed to be intentionally going slowly. By the time the clock hit 32 minutes, she was about halfway done. Maria stuck a finger inside of herself and wetted the short hairs on her eyebrows which were only beginning to grow back. She grabbed Naomi’s hand and held it so the razor touched her brows, and Naomi slowly erased the stubble. Maria lowered her head again and let Naomi go back to work, fingering herself while rubbing Naomi’s beautifully tattooed scalp.

It didn’t take much longer for Naomi to reduce Maria’s remaining hair back to smooth, pale skin. By the 40 minute mark, there was nothing left. Naomi had completed the challenge with ease.

Naomi then reached for her mask and took it off. There was no point obscuring her face when her distinctive tattoo was on display. She instructed Maria to stand up and slid her hand onto her hip.

Undoing the ties that held the magic wand vibrator against Maria’s clit, Naomi inserted two fingers inside Maria while teasing her pierced clit with expert flicks of her tongue. As she moved her fingers inside of Maria’s pussy in alternating motions, Maria pushed down on Naomi’s bald head with one hand while hanging on to the ceiling rope with the other. At the 44 minute mark, Maria experienced the first orgasm of her life that she herself hadn’t caused, as the vibrations of the machine simultaneously caused Naomi to burst out in pleasure. Naomi then grabbed Maria’s hand and pulled her down so she knelt on the floor. As the timer neared 45 minutes, she whispered to Maria “Don’t act like I don’t know what this button does.” she winked, and then took a clump of wet stubble from the towel and rubbed it across her scalp. “Oops!” She said sarcastically as she held a hand over her mouth. With the other hand, she guided Maria’s finger, and as the clock hit 45, she hit the button.

The branding iron struck quickly, and Naomi would now wear Maria’s mark for the rest of her life as a reminder of this night.

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