Note to the reader: This is a fifth in my “Boy Alone in The Condo For The Weekend” series. It has a lot in common with its predecessors, World’s Record, Apparition, Power Failure, and Star Light, Star Bright, in that Henry is woefully inadequate as a boy, and wants to be a girl. Like all before him, he will get high and experience bizarre and frightening events in the condo.
As before, some readers may not like this story because of its borderline-gay protagonist. However, Henry is more schizophrenic than gay, struggling to accept who/what he is. There is no sex between guys, only between Henry and his imaginary twin Hailey, abetting his mental instability. Girls will probably like the story best.
Another note: The names Henry and Hailey Van Kuren were borrowed from a Law & Order SVU episode called Transitions. (Season 10, Episode 14.) To anyone that remembers the episode, this story will make more sense.
What Hailey was doing was stupid. Not only a school night, but Mom and Dad were still awake. So was Angie, she imagined, and maybe even Katie, her siblings, ages seventeen and eleven. Hailey was 14 years old. It was Thursday, October 23rd. She glanced at the bedside clock: 11:21 p.m.
Her “twin”, Henry was embarrassingly small for a boy. Angie had him by four inches and sixteen pounds. He was not a whole lot bigger than his 11-old sister, in fact. Blonde like Katie, Henry wore his hair buzzed right to the scalp. He was constantly picked on in school, worse now in ninth grade than ever before. At the same time, no one but Kevin Mallory ever menaced him seriously; there was just something about the boy. Girls lovingly teased him, and Henry had this grim blushing problem, making it even worse, egging them on. Girls were the worst. Henry wanted to be a girl.
Hailey lay in his bed, face down, smiling dreamily. She knew this was stupid, but still had Henry’s pajama bottoms and underwear pushed down below her cheeks. Up her rear end was a fairly large dildo. She gripped it tightly with her anus and rectal muscles, and then let them relax. Hailey enjoyed nothing more than a dildo up her behind.
The dildo was not hers. Henry had discovered it secreted in a green backpack tossed to the side of the road in July. In a separate pocket was a heavy-duty Ziploc bag containing two ounces of excellent weed, divided into smaller Ziploc bags of ten grams each. A third baggie contained a dozen packs of Zig-Zag rolling papers. So far, she and Henry had smoked a couple grams of the weed. It was extraordinarily potent stuff. Hailey loved it. So did Henry.
“We are so stupid, doing this,” Hailey murmured.
“We need our effing heads examined,” Henry agreed.
“Scratch my left butt cheek? It itches something awful.”
“No prob,” he said, patting her rear end.
“Stop that,” she grumbled, slapping at his hand. “I asked you to scratch, not cop a feel, pervert.”
Henry laughed, and then scratched her butt cheek as requested.
“Lower,” she directed. “More to the right. Oh, good ... you got it just right now. Don’t stop.” She sighed, and then lifted her head. “Leave the dildo alone, Henry Van Kuren.” She squirmed uncomfortably; Henry chuckled. “Do you want me to leave, Henry?”
“No,” he admitted sheepishly. He liked his sister in bed with him—it was so unbelievably sexy. No--she was so unbelievably sexy. For a girl with no hair, a flat chest, and no vagina, that is. Only...
“Don’t start that again,” she grumbled.
Henry shrugged tightly. “You could at least talk about it, sis.”
“I don’t want to talk about it, dammit. And don’t call me sis. You know I hate that crap.” She tucked herself in tightly. “Don’t ruin our night together, Henry.”
In the morning, Henry tossed aside the covers and sat up. His rear end hurt. He glanced at the closet door and shook his head, thinking what an idiotic move, putting that damned thing up his behind on a school night. He had a death wish on top of being schizophrenic?
He scratched his chest and yawned. He stretched, listening to joints in his shoulders and spine go snap, crackle, and pop. Henry liked a good stretch nearly as much as Hailey liked a stiff pecker up her behind. Too bad Hailey wasn’t here to offer him a nice blowjob now, he thought. He gazed down, imagining her sweet mouth wrapped around his knob, sliding her lips down his shaft, teasing him with her tongue. He got an immediate, dynamite erection.
Struggling to his feet, he went to the dresser, grabbed a pair of shorts from the top drawer, and yanked them on. He normally wore Jockey shorts to school, hating the way boxers left him feeling unsecured down there. Especially in gym.
Thank God Kevin Mallory was in a different gym class this year. Too bad the asshole didn’t attend an entirely different high school, preferably one out of state. A bona-fide asshole, he relentlessly gave Henry a hard time, yet was the only boy Henry’d ever considered wrapping his lips around--if the opportunity ever presented itself, which Henry fervently prayed wouldn’t. Hailey hated the asshole.
He crossed the hall and pushed open the bathroom door, shutting it just as Katie opened her bedroom door and peaked out. “What?” he demanded, opening the door again. She was in her Katy Perry pajamas, the ones Hailey coveted. She blinked, offering up a lopsided grin.
“Don’t use all the hot water, Henry.”
Henry gave her the finger, which made Katie’s grin stretch out full width. “Eff you too,” she mouthed, raising a middle finger of her own. Unlike Angie, this one he got along with fine.
“You still a virgin?” he whispered.
“Like you?” she shot back.
Henry reddened. Being only 11, Katie had justification for her purity status; Henry did not. He had never even kissed a girl, while by her own boastful admissions, Katie had kissed half a dozen boys so far, including one that had taught her to French kiss. Henry kissed only his pillow.
“Hands off,” he warned. Katie’s grin widened even farther. She made a cutting gesture with her right hand. The same boy that taught her how to French kiss also wanted to teach her how to give a blow job and take a fat cock. Henry wanted to punch his lights out. The boy was thirteen, and had no business messing with a girl in 6th grade. Luckily, she had cut him off with a good wrist slapping and that was that. She twiddled her fingers at Henry and closed her bedroom door.
Angie and Katie had bathrooms of their own, which Henry always complained was unfair; given the effing condo had five bathrooms, including the powder room by the front door. Stripping off his T-shirt and tossing it on the floor, he reconsidered: a dedicated bathroom would mean he’d have to clean the effing thing, instead of that being the maid’s responsibility. He’d bet Hailey would have her own bathroom, though. So unfair.
“Do not use all the hot water,” Angie warned through the door with a thump. He jumped, reflexively lofting a finger in response to her admonition. Effing bitch.
Angie harassed him mercilessly. She loved making him panic, doing shit like opening the door while he sat on the pot or went pee. He looked down, wishing the bowl was her effing mouth. A mouth he wouldn’t mind fucking, actually. Hands behind her back, tied at the wrists with her own brassiere. On her knees in her underwear and bra, like the boy he’d watched having his mouth fucked over the weekend. No way did he believe that boy was eighteen, by the way; he looked no older than Henry. In fact, he looked a lot like Henry, right down to his pitiful cock and minuscule balls.
Henry locked the door, stripped off his shorts, and tossed them atop his T-shirt. He had the smallest cock in the school, he thought, barely 4” long with a Guinness-sized hard-on. It agonized him, imagining himself with a girl: she’d laugh, even worse, giggle her head off while she tried to apologize. Of course, she’d tell all her friends.
Truth was, Henry imagined his future lay with boys instead of girls: it didn’t matter how effing big your cock was if you never had to use it. Like the boy in the video, Henry would get his mouth fucked good and hard by big thick cocks. His little mouse would just flap uselessly as a guy rode Henry like a bitch. It made his asshole ache, imagining a cock the size of Hailey’s dildo plumbing his rectum until it came. He squirmed, imagining a cum-gush filling him to bursting while he squealed effeminately. He farted in response, making himself grimace.
He showered quickly, donned his shorts, and brushed his teeth, put on deodorant in the mirror. He was so abysmally skinny, ribs jutting through his skin, arms barely thicker than his minuscule pecker. For God’s sake, look at the thigh-gap he had! Angie would kill for that thigh gap, Katie had told him enviously. He disgustedly wrapped the towel around his middle. Maybe Tim Malone would finally shag his skinny ass, put him out of his misery. Let it be soon, he thought.
In his bedroom, Henry dressed, then went downstairs to say goodbye to his mom. He was always first out the door, his bus arriving earlier than either of his siblings. Most days, he wouldn’t even see them before school, unless Katie stuck her head outside her bedroom door to say hi, like this morning. Henry wished she were old enough to share his secrets. He liked sharing with Katie; she was just too young.
“Hi, Mom.” He buzzed her on the cheek going by.
.... There is more of this story ...