This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Eighteen year old Jeremy Briarstein is forced to remain home while his parents go on an extended twenty year anniversary vacation. He is further dismayed to discover he will be in the charge of a “caretaker” a glorified babysitter named Carmen Rendon-Gould. A wannabe dominatrix, Carmen is quick to discover a little secret about Jeremy, he is a secret cam sissy and blackmails him into being her personal bottom bitch after catching him in a compromising position. She then trains Jeremy into being the camera famous sissy of his dreams.
The Hollywood Hills. The famous neighborhood with million dollar mansions and billion dollar views. Along the famous stretch of Mulholland drive, sits a house jutting off the side of the hill facing Los Angeles’s Westside region.
This house was so spectacular that despite hanging off the hill, it somehow sported a pool, that’s how you know they have money. This dead-tech postmodern abode belonged to the Briarstein family. Parents Gene and Elaine Briarstein are sitting in their living room addressing their only child, eighteen year old Jeremy. Their professions and appearances aren’t important, if they could afford this overpriced house, just know whatever they do, they make money.
The focus is that of Jeremy. A recent high school graduate, he stood a stark five foot six inches, relatively small for a guy. Very skinny in his chest arms and stomach, with more muscular legs and a fairly toned ass, not the flat or flabby asses of guys who don’t take care of themselves. He had brown eyes and curly brown hair in sort of pompadour style.
His parents had begun their conversation explaining to the recent graduate that they would be going on a three week excursion throughout Europe as a sort of extended twenty year anniversary present to themselves. Jeremy was at first thrilled, thinking this would be three fun-filled weeks of no responsibilities or things to do, until he was told that he would be under the watchful eye of—
“A babysitter? For real?” Jeremy snorted.
“No, I didn’t say a babysitter” Gene scolded his spoiled brat of a son. “She’ll be more of a—what did you call it?” he asked Elaine.
“A caretaker, honey.”
“Well whatever you call her, it’s such bullshit”
“Jeremy, language!” his mother spat.
“It’s not fair! I’m eighteen now, I can stay home on my own.”
“Legally you can” His father added.
“So, what’s the big deal, then?” Jeremy asked.
“It’s three weeks, my son” Eaine added. “Maybe three days we could see that working out, but nearly a month completely unsupervised? I don’t think I have to tell you that’s a recipe for disaster.”
“What, do you think I’m going to throw some ratchet-ass party or some shit?”
“Yes” Both parents deadpanned in unison.
“Dad, come on” Jeremy tried to persuade his father.
“Jeremy, it’s out of the question. And it’s not just to make sure you behave, she’s mostly going to be doing some of the chores and taking care of our plants. Jorge and Consuela are also taking their vacations this week.”
“You’ll hardly know she’s here” Elaine assured him. “You spend most of your time in your room anyway.”
“Whatever. This is such bullshit”
“Jeremy!” Elaine scolded.
“Fuck this!” Jeremy got off the couch and stomped off towards his room.
Gene rubbed his head. “See. I told you this is how he’d react.”
“Well we can’t cancel our trip, we’ll never get the deposit back. He’ll just have to deal.”
“You’re right, especially with all the time he spends with his video games and online chicaneries” Gene added.
“What do you suppose he does in there, anyhow?” Elaine asked.
“As long as it’s nothing illegal, it’s better off if we don’t know” Gene sighed.
While we take a minute to ponder Elaine and Gene’s suspect parenting techniques, we fade to outside the mansion later as a beat up Mitsubishi Lancer pulled into the driveway, nearly clipping a passing motorist on the dangerous winding deathtrap that is Mulholland Drive.
A woman stepped out of the car, dropping a roach on the driveway which she tamped out with her foot. She grabbed a perfume bottle from Ulta or Sephora, or wherever and spritzed herself down with it.
She was tall, about five foot nine, light brown complexion with long brown hair. She wore cute glasses covering her face. She had a nice and tight chest with D cup breasts covered in a striped tank top with skinny jeans jamming a beautiful ass inside of them. She was Jeremy’s twenty-four year old caretaker Carmen Rendon-Gould.
With her was a backpack, and large duffel bag. She took a gander around the houses along the star-studded hillside street. She snapped a few pictures with her phone before walking up to two large wooden front doors and making a knock. A few moments later, Elaine acıbadem escort answered the door.
“Oh hi, Carmen. Glad you’re here.”
“Glad to be here Mrs. Briarstein” she said in a sort of fake enthusiastic voice.
“Won’t you come in?” she offered.
“Yes of course.”
Elaine took a whiff of Carmen as she walked past and winced. It was a mix of cheap perfume with just a hint of weed. Fortunately the cheap perfume smell did a fairly decent job at masking the usually potent weed smell.
Gene, finagling some bags down the stairs stopped to greet his caretaker. “Oh Carmen, this is my husband, Eugene Briarstein.”
“Hi, I’m Gene. Thanks so much for doing this” he huffed, not used to this amount of physical activity.
“Oh of course, I’m always happy to help.”
“Okay so I don’t know how much Elaine explained to you but essentially we just want our house to be in one piece when we get back. We have some plants that need watering every day, and just in general do not make a mess. And don’t mind our son, he keeps to himself.”
“Just make sure he behaves and doesn’t throw any crazy parties” Elaine sternly warned Carmen.
“Sounds easy enough” Carmen nodded. “So, where’s like, Tarantino’s house?”
“Just down the road and up that hill, you can see it from the living room” Elaine explained.
Immediately, Carmen ran to the main window in the living room and looked out, like a puppy wagging its tail seeing its owner return home after work. Gene and Elaine moved their bags to their car outside while Carmen hadn’t noticed.
While she did this, she didn’t see Jeremy emerge from the nearby stairs and eye up Carmen while she tried to spot the famed movie director’s residence. Carmen then turned around assuming the parents were still there.
“Is it that giant stucco one over th—” she stopped as she got a glimpse of Jeremy. “Oh, you must be the son?”
“Jeremy, yeah.”
“Hi, I’m Carmen, I’m the house-sitter.”
“I was told the caretaker.”
“Meh, semantics” Carmen shrugged.
“Just letting you know, you ARE NOT my babysitter. Understand?” Jeremy asked sounding all tough and stuff.
Carmen was a bit taken aback, nobody talks to her that way, especially rich little snots like this kid. But, his parents were still around and her high was putting her in on a one-way trip to mellow-town; so cooler heads prevailed and she gave him a mental pass.
“S’all good, man. All I’m here to do is water some plants and shit. I’ll spend my time here, you’ll barely know I’m around.”
“I’d better not” Jeremy then marched up to his room just as his parents came back into the house.
“Jeremy, sweetie, give mommy and daddy a hug goodb—” this was interrupted by the loud slamming of a door, clearly being Jeremy’s bedroom door. Both parents rolled their eyes and took deep breaths. Elaine turned to Carmen. “I’ll give you a quick tour, then we have to go” she explained.
“I can find where things are” Carmen insisted.
“Well the watering can is in the kitchen, tap water is fine. Guest bedroom is down the hall, has its own bathroom, make yourself at home” she explained as Gene was tapping his watch signaling they would be late. “We have to go, I suppose—you have our number if you need to reach us, and if you need to find something, have Jeremy get out of his room and help you.”
“Yes, and thank you so much again, Carmen, we appreciate it” Gene assured her before both of them found their way out the door. Carmen looked outside as their Porsche Cayenne rolled out of the driveway and sped down Mulholland.
“And they…are…gone!” Carmen cheered and happily ran to get her backpack, pulling out some cannabis gummies, popping two of them and jumping back onto the couch. “T-minus forty-five minutes to away we go” she swooned turning on the flat screen TV and activating Apple TV. She chose from the variety of streaming sites and decided to waste her precious time and brain cells on some mindless reality television drivel.
She saw on the coffee table a note containing the family’s wifi and the all-too-important password that went with it. Carmen quickly connected her phone to the internet, saving her from debilitating data overage charges.
Day turned into night as Carmen’s high intensified, popping a gummy or two as her lightheadedness was vastly turning into that rush of ‘oh, I’m high right now’ feeling. She was in the stage where everything seemed funny even when it wasn’t and your grin is: stupid, dopey, and creepy simultaneously.
Carmen was scrolling over her phone some nearly nude photos of dudes while shoving her hand into her shorts not really in the right head space to know if there was anybody watching her do this. She then toggled to a different website, a chatroom where dudes like to be dominated by chicks, as Carmen was into that very much.
Soon, Carmen stopped her mellow masturbation and put down her phone as she was slowly drifting off into sleep-land, she barely atalar escort noticed Jeremy walk down the stairs and catch a glimpse of her. She didn’t seem to move but her eyes shifted towards the shadowy blob of the eighteen year old.
The paranoia was kicking in. It was a feeling of perceived dread, like Jeremy was going to take advantage of her in this extremely stoned state. She figured given the look of him she could kick his ass but not in this condition and a part of her feared for the worst, but that was just the kush talking.
Her fears were placated almost immediately after Jeremy caught a glimpse of her, he walked back up the stairs and gently closed his door, albeit making it ajar this time, probably in an effort not to arouse suspicion from Carmen.
The Latina continued her cavalcade of phoned-in stupidity on the Netflix and her mind started to wander, because that was all she could do lest she lose more precious braincells, not from the weed, but from the terrible reality TV that lay in front of her.
She started to think about her own life. She came from relative hardscrabble in the dicey Los Angeles neighborhood of Van Nuys, located in the middle of the hot and sweaty San Fernando Valley on the other side of the lavish Hollywood Hills. She thought of Jeremy, this seemingly spoiled brat of an eighteen year old where everything seemed to have come easy to him and why he acted the way he did. The house was huge, he had a stable parental relationship with little in the way of financial woes, yet here he was being the world’s biggest jerk-off over not being able to be barely legal and in charge of his parent’s house while they went on a seemingly much needed vacation.
Now, not that Carmen was immune from teenage douchebag-ery, most millennials and zoomers aren’t, but Carmen never had it this bad when she was Jeremy’s age. Hell, she even had a part-time job by eighteen. She felt like Jeremy needed a swift kick in the ass, maybe that would teach him, but knowing Carmen’s luck he would call the police and she would go to jail and he could throw a rager uninhibited.
Carmen’s eyes started to shut as the Netflix menu of ‘still watching?’ appeared, waking Carmen up as she realized there was no TV streaming into her eyes. She got up and rubbed some drool from her face. She got up and grabbed her things, stumbling into the guest bedroom down the hall as was explained by Elaine. She walked in and noticed the room was Airbnb ready. Perfectly drawn sheets, king sized bed, two nightstands, decently sized closet with attached bathroom with glass shower and such.
“Yo, this is off the fucking chain” she mused like a 1980’s stoner. She dropped her things onto the floor and flopped down on the bed, admiring the sheets as she wrapped her inebriated body around them. After a few moments, her stomach rumbled, and the munchies were kicking in. She yawned and started to throw on her pajamas, getting slightly naked in the process, and we get to admire Carmen’s fit bod.
Her jammers consisted of a t-shirt with OCCIDENTAL COLLEGE emblazoned on the front, and some booty shorts. She walked out of the bedroom. “Jeremy! I’m ordering a pizza!” she called, almost not as if she was offering him any, though she wouldn’t mind, but more so that her stoned brain for whatever reason felt the need to shout what she was about to do.
“I don’t eat carbs!” Jeremy called from his room, opening his door before shutting it.
“Then go fuck yourself” Carmen muttered.
Carmen waltzed back to her bedroom and flopped on the bed again, twisting herself to get to the top of the bed by the pillows; a position where she could face the bedroom door, leaving it partially opened.
Stoned Carmen made the attempt to order Dominos but the munchies couldn’t decide which greasy mess she wanted more. After a few more moments of indecision, Carmen once again felt glassy eyed, dropping her phone to the bed and her eyes closed a little.
Sometime later, the paranoia was back and Carmen heard the creaky sounds of a door open, her blurry eyes saw the blob of creepster Jeremy once again. He peaked his head in and saw that Carmen seemed to have been asleep. Had he been closer he could have seen her super squinted eyes. Carmen was about to move to show she was aware of his presence as his behavior was starting to disturb her but Jeremy then sneaked out, slowly closing the door completely.
Now a bit perturbed as this had happened twice, Carmen shook her head, trying to get her wits about her. She fell off the bed and grunted, before getting up. She grabbed her phone, gently opened her door and sneaked outside, wondering what it was Jeremy was up to, because unless he was trying to do something sexually illegal and evil, then he was clearly trying to see if Carmen would be out of commission for any extended period of time, allowing him to do something at the very least embarrassing up in his room without interference. Carmen smirked as she tiptoed towards the house and to aydınlı escort the stairs, while the eerie musical score from the ending of the tense Breaking Bad episode: Half Measures, echoed in her head as she moved about the nearly empty house. Except this didn’t end with Walter White killing two drug dealers in a twist ending; a series defining move saving the life of his partner: Jesse Pinkman; this probably ended with Carmen catching Jeremy masturbating to hentai or something like that.
Well, we transition into Jeremy’s room as we count down our proverbial ticking clock and get some insight into just what the ‘something like that’ actually was. We’re in Jeremy’s room, which looks just the way you are probably describing it given his character up until this point.
He had a few movie posters adorning his walls, most of them being of the Dodgers and Los Angeles Rams. Some free weights that seemed barely used were sitting on his floor off in a corner of the room collecting dust. His unkempt bed with sheets drenched in old flop sweat were also Dodgers themed. He of course had a giant TV with every video game console and electronic device under the sun. Dirty clothes were strewn about his room. His computer desk, also bedecked in clothing had a massive monitor with built-in webcam and surround sound system, perfect for gaming and such.
But what was on the computer, coupled with Jeremy’s appearance is what separated this from a typical eighteen year old boy’s room. On the monitor was a website, complete with a webcam feature. The website was called: SISSY CAM, and while completely unimaginative it certainly had a fan following.
For Jeremy’s part, he wasn’t perusing the site, so much as he was a “model” on the site. The site itself was dedicated to sissy dudes typically dressing in drag and playing with themselves for a perspective audience where they could make requests, send tips, and communicate.
Jeremy really got into the part. He was wearing a red wig with some makeup most likely pilfered from his mother. He was also in a tight black sheer nightie with matching thong, and silk stockings. The site was populated by largely by a trans women audience usually making lewd suggestions for the models. Jeremy was reading a few in the comments thread of his live feed.
“Can you jerk yourself off and finger your hole?” he read one of them. “I can do more than that.”
Jeremy situated himself in his swivel chair, spreading his legs out. He grabbed a small pink vibrator on his desk, and lubed it up in a tub of petroleum jelly he had on the desk. He lubed up his fingers and started to insert them into his perfectly shaven hole.
Jeremy started to moan lightly while his fingers stretched him out. He spread his legs out a bit more so the camera could capture the scene from the best possible angle. He got his middle and index finger nearly knuckles deep before pulling out.
Quickly these were replaced with the vibrator. Jeremy grunted but slipped the dick past his sphincter and up inside of him, gently pushing in and out while he received online praise and a few tips.
Using his free hand, still covered in the lube, Jeremy started to jerk himself off. His cock was not that impressive to say the least, but he didn’t seem to mind as his level of sexual fortitude was on a different aspect of his body.
“You like that?” Jeremy moaned while receiving more comments of praise.
He continued to jerk his small dick while the vibrator got nearly all the way inside of him. Jeremy relished in every moment of his moderate online fame, hoping no one he knew would see such debauchery…but then again, they would have to admit to watching the content in the first place.
Jeremy read a few comments—
AsS_cOck: nice dildo.”
Charmer5890: love the makeup.”
xXxSissyButtBoyPounderxXx: $20 if we get to see some ass, tho.”
Jeremy liked the sound of ass. It was the best of both worlds, he can show himself off and make a little money while doing it. He got up and moved his body so it was on the other side of the chair, and knelt on the seat, bending his midsection over the chair.
He had the vibrator wedged inside his hole while his dude booty was in perfect view of the camera, he could literally feel the likes, comments, and subscribes pouring in as he showed off his ass.
He reached back his hand and pushed the vibrator in and out to get additional reactions from his fans. Little did young Jeremy know he had an admirer of the off-screen kind watching him from a very close distance.
Carmen made it to the outside of Jeremy’s bedroom door, the hallway was dark but the ajar door provided the perfect amount of light for her to sneak forward. Carmen rested her head against the crack and peaked one eye inside.
Her eyes went wide when they got a gander of the compromising position Jeremy had put himself in. Wow, the spoiled bratty child who never had a problem in his life was into dressing up in a wig and stockings and dildoing his ass, who knew?
She had to bite her lip in order not to give herself away. Not able to resist, Carmen put her camera lens against the door and took a brief movie, perfectly incriminating. She chuckled to herself and turned away but then she stopped.