Note to the reader: Hi, my name is Angie, and I authored this story. As with my other short stories dealing with this subject matter, it will not be universally liked. To say the least, LOL. It is another in my series of gayish teen boys (interacting with teens girls, whether imagined, or real) left alone at home for the weekend, and their resulting misadventures. My earlier stories in this series are Power Failure, Apparition, and World’s Record. In all of these stories, the boy ends up a girl, or saves the life of one. Here, he does both.
I like to believe this is the best of the four stories, but readers may have other opinions about that. (Again, LOL.) As usual, some will flame it with a 1 or a 2, hating anything to do with gayish boys, or just my stories in general. This one may engender more rage than normal, as Henry performs an activity that none of the other boys engaged in, namely sucking his own penis. I lost a lot of readers right there, I suspect.
I planned to write out that activity in the rewrites. However, it went such a long way toward explaining Henry’s fractured psyche, and his heartbreaking desire to be a girl, that I left it in. My guess is a lot of boys actually have tried it in the privacy of their bedrooms after school.
Anyway, for those of you that enjoyed my three earlier Home Alone-style stories, may I introduce Henry Howard Calder, and his counterpart in another universe, Hailey Marie.
Henry was unfortunately slight for a boy. He stood only 5’2” tall and weighed 105 lbs. He’d inherited his mother’s bright blue eyes and blond hair, also her flawless complexion. In his opinion, no 10th-grader at Bethesda-Chevy Chase High School stood a better chance of being a closet queen than Henry Calder. Henry thought he was hopelessly gay. What he was, in fact, was infinitely more complex.
He’d sucked only one cock, that of his friend Charles. He’d been cockless since July, when Charles had moved to a suburb of Pittsburgh. Charles had not returned his last two texts, so it looked like that part of his life was over now. It left a huge hole in Henry’s life. It left a hole in his heart.
Henry was surprisingly nimble. Amazingly nimble, really. Two weeks into the new school year, he’d discovered it was possible to suck his own cock. He’d watched a handful of boys doing it on the porn site xHamster. It flat out amazed him that a boy would--could--suck his own cock, but the ones he’d watched on xHamster did it three different ways. He’d watched the videos Saturday and Sunday night, and then rushed home Monday afternoon after school to give it a try. He’d failed, miserably, but that didn’t stop him from trying again.
Tuesday afternoon, following an hour’s ordeal inching his cock ever nearer his mouth, he’d finally flicked the tip with his tongue, and coaxed it between his lips. He’d laughed so hard in relief and excitement that he’d spasmodically unfolded and flopped flat on his bed.
“Fuck!” he protested, laughing even harder. “You suck, dude!” Truth was, sucking his own cock for even that few seconds was a real mind fuck. God ... he had actually done it!
His next attempt, toes locked to the raised edge of his headboard, folded over like a gymnast, cock directly over his mouth and ready, he’d closed his eyes and slowly coaxed the head to his lips again. Closing around it, he’d sucked gently and fingered the shaft with his right hand, using the other arm to help stay folded. Though awkward and uncomfortable at first, the effort proved worthy, and eventually he managed to suck more than half his length. He didn’t come ... it was too mind blowing a development his first time.
Wednesday afternoon, before taking off his clothing, Henry disabled the cellular and wifi functions on his iPhone to record himself. He had to know what he looked like, sucking his own cock. (4-1/2” long, on a really exceptional day.) Capturing the phone between two books standing upright, plugged in, ready to record every moment of this, his second, momentous suck-a-thon, he stripped naked. Rock hard, though stiff and sore from his workout Tuesday afternoon, Henry was ready.
Getting the head between his lips took five minutes longer than expected. He worried suddenly just how much video his 16 gig iPhone could record. No way to know, without looking, he realized. Unfolding, he went to check the phone. It had already shut off. “Fuck,” he muttered, angrily.
He watched the video, fingering his diminutive head as he did, heart rate increasing to match his arousal. Dropping the phone, he raced back to the bed and got himself back into position. A minute later he started to suck the head. Contorting his spine impossibly, allowed the entire length to go into his mouth, and no way did he believe he was giving himself a blowjob. He came in his mouth this time and swallowed every drop.
Panting, he wiped his mouth with the back of his hand and shivered disgustedly. This wasn’t his first time, swallowing cum. He’d swallowed Charles’ more times than he could count. Charles had counted, though, unbeknownst to Henry, and the total was forty-seven times. It always grossed him out, but Charles just loved it.
“I wish you had fucked me,” Henry muttered. Charles never had, although Henry had asked him numerous times. Instead, Henry boned himself with his mom’s dildo after school. He’d discovered it two years ago, hidden away in her walk-in closet. He’d also found Big Brother, a monster cock 9” long and 2” thick that he’d used only once. He jumped up and scurried to his mom’s bedroom to get the small one.
Saturday night. Dad was out of town until Wednesday, and Mom had the overnight shift at Suburban Hospital Trauma Center. Henry ate a frozen pizza for dinner and battled the Xbox until she left at 11 o’clock. This was a special occasion for Henry; once Mom left, it was him and Edward until Mom came home in the morning. He could fall asleep with Edward up his behind, whatever he wanted. Not the first time; but the first time it could be done safely.
He suppressed his excitement, anxiety eating away at his stomach lining. Once she left, he waited an obligatory ten minutes for safety and then dashed straight to her bedroom. The dildo waited in her closet.
He’d used her lubricant only once. The dildo was one thing; wash it good and clean and put it back in the shoe box and no one would ever know. Replacing her bottle of KY Personal Lubricant was not an option. He used butter, instead, or margarine if the real thing wasn’t available. Sometimes he used vegetable oil; anything to lube his rear and let Edward have its way with him. He seriously loved Edward’s 6” of cock.
Since Wednesday afternoon, he’d sucked himself twice more: once Thursday afternoon, and again on Friday. It tickled him, having his nose tickled by pubic hair. Oh, how he wished he could suck his cock while Edward enjoyed his bottom. He could, he supposed, do both at once, but that was a lot of work. Probably, he would not enjoy it, though it would definitely be unique. He wished Edward were a vibrator, in addition to being a dildo.
By 11:15 pm, Henry was naked on his bed, hips elevated atop a thick corduroy bed rest; Edward fit snugly up his ass. So happy, he was, so contented. Nothing pleased him like Edward up his behind. Nothing could, short of being a girl.
Wanting to be girl was nothing new. He’d wanted that since the age of five when he’d played dress up with his six year old cousin, Sofia. He was smaller than she, but not so much that her size 4 dresses and tights, jeans and shirts wouldn’t fit. It was a magical weekend away, and left him broken-hearted when Mom said he couldn’t dress like Sofia at home.
Relaxed and happy, fantasizing a vagina to offer Edward instead of his rectum, imagining small but desirable breasts flattened against the comforter, Henry drifted off. The time was 11:35 p.m.
He awoke at 1:12 am, laughed amusedly, and fell immediately back asleep. He awoke a second time at 3:17 am. Edward had nested inside him over four hours now. It was not the longest his rectum had played host to Edward, but he needed to go pee. Badly.
“Eff,” he sighed. “I don’t want to take you out.” He had an idea. “That’s just plain stupid,” he told himself. “The stupidest thing you ever thought about.” It didn’t stop him from hobbling into his mom’s bedroom, though, holding the dildo in place, first with his right hand, and then the left. Picking a pair at random, he struggled into Mom’s purple lace panties and got them snugged around his hips. His hard-on was a killer, nearly impossible to contain in Mom’s thin panties.
“This is so stupid,” he muttered, searching out the matching lace bra and struggling into it experimentally. It was his first time in his mother’s underthings. The bra and panties were Victoria’s Secret brand.
.... There is more of this story ...