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.

Suddenly paranoid, he crept to the window overlooking the rear lot and Building 6400, and raised a slat. A plane in the distance caught his eye, low enough to show the green light at the end of the wing and the flashing strobes. Movement below caught his eye and Henry looked down. Traversing the rear lot of his building, and entering the adjacent lot was a yellow Hummer H3. It moved unnaturally slow, leading Henry to wonder about the driver’s state of sobriety. Taking forever, the Hummer finally found a space at the end of a row and parked. Was that a Lincoln Towncar beside it, he wondered? He hated those ugly, pretentious gas-guzzlers. His favorite vice principal, that fat cow Mrs. Jorgensen drove a Lincoln. The thought of her fat ass behind the wheel made him grimace. He dropped the slat and turned away, unaware he’d just missed a treat. Exiting the Hummer, a pretty young blonde yanked up the front of her sweater and flashed her boobs at the driver, and then at anyone watching in the two hi-rise condos. A terrible injustice, I know, but Henry would get another chance.

He returned to his mom’s dresser and began to rummage through her drawers. Finding a pair of purple thigh-hi’s, he shook them in preparation of slipping them on when his cell phone rang across the condo. Panicked, he dropped the stockings and dashed awkwardly back to his bedroom.

“Nothing’s wrong,” Mom said. “Sorry to wake you, but they asked me to work a second shift, and I didn’t want you worryingly about me in the morning, when you woke up.”

“Thanks,” he said gratefully. He could do what he wanted with Edward now, and not worry about being caught. Mom wouldn’t get home until 5 p.m. Plenty enough time to play.

“How ‘bout a beer,” he mused. In bra and panties, he moved through darkness to the kitchen and opened the refrigerator door. The bright light illuminated Mom’s cute little outfit. Embarrassed, he glanced at the big window over the stove, wondering if anyone in the opposite condo would see the light, and check him out with binoculars. It was a danger, he knew; the world was full of perverts. A moment later, he wondered if that voyeur might also discover Edward up his behind. It would be perfectly obvious from the correct angle, he thought. Blushing, he forced himself not to look down. He could do nothing about his ferocious little hard-on.

His mom didn’t drink. Dad loved Heineken and always kept a pair of sixes on the shelf. He removed a bottle and spun off the cap. He loved Heineken almost as much as his dad did. Taking a long swig, he leaned back against the counter, knowing his mom wouldn’t care. She allowed him a beer once in a while. He gazed at the kitchen window again.

“Edward’s fucking me,” he said to his possible voyeurs. He turned and pulled aside his purple panties to reveal the end of Henry’s cock. The flat base, front sculpted in the shape of a scrotum, was quite large. He envied the faux testicles, twice the size of his own. The base rested uncomfortably inside Mom’s panties.

“Want to see my hard-on?” he asked the wide window. Turning, he pulled aside the front of Mom’s panties and exposed his scrotum and 4-1/2” long erection. His pecker thumped so hard it ached. He gave the shaft half a dozen good strokes with his fingertips, and then fondled his balls. How more queer could he get, he wondered. Pink Panties queer? Baby-doll Nighty queer? How about Training Bra Queer, he thought, laughing harshly. He wished he had a training bra to wear.

He downed the beer with his package exposed, opened the refrigerator door and removed a 2nd beer. What he really wanted--aside from sucking his cock and having his bottom lovingly fucked (or magically becoming a girl)--was some good weed. He went to his Mom’s room to remedy that.

His mom was slender, a size 6. In her closet was a sleeveless black dress that Henry eyed longingly. Before slipping it on, he retrieved and donned the pair of purple thigh-hi’s he’d dropped on the floor earlier. Since he knew from numerous explorations where to look, he retrieved the box containing her silicone breast shapers from the bottom right drawer of her dresser and slipped two each into her bra cups. (Mom was ridiculously small-breasted.) Then he chose a black wig from her selection of three on an upper shelf, slipped it on carefully, and examined himself in the full length mirror on her door.

I make a convincingly cute girl, he thought, wistfully. Except for the hard-on, of course. He slipped on her pair of black stiletto heels--her Fuck-Me heels, he called them-and then slipped into her dress. Zipping the darned thing left him giggling hysterically. And finally, he was done.

“Jesus, Henry...” The girl facing him in the mirror sent a shiver of longing down his spine and squeezed his insides in untellable ways. With no affectation, he said in a clear girl’s voice, two octaves higher than his own, “Hi. I’m Hailey, Henry’s little sister. Actually, I’m twelve minutes younger, because Henry muscled me out of the way, right at the last moment, the little shit.” He grinned shyly, showing his small white teeth. “I’m a virgin, because I haven’t met the right boy yet.” He hesitated. “Actually, I have, but he doesn’t know I exist.” Which was true, but only in the abstract. Dennis Chance knew Henry only too well: as Henry’s classmate since 4th grade. He was Henry’s mental tormentor-in-chief.

“Well, you know how to kill a mood,” he muttered, suddenly depressed. Mumbling, he broke into Mom’s stash.

In addition to a dozen rolled joints, a baggie was stuffed with lush green leaves. Medical marijuana, he thought ... what a joke. Taking a pair of joints and the Bic lighter, he set the box aside, and returned to the kitchen for his beer.

The condo had balconies front and rear, but his only choice right now was the back. The front overlooked the parking lot, and even at 3:45 am, he might be seen. Not that smoking pot on the front balcony worried him so much. It was Mom’s black dress, obviously.

It was colder than he expected. Huddled in the corner until his eyes adjusted, he skirted the balcony table and moved to the railing, enjoying every movement of Edward as he walked. He was dangerously unstable in Mom’s heels; he was dangerously unstable in general, he thought amusedly. Looking up, enjoying the fantasy of being a woman, he immediately spotted the North Star.

“‘Star light, star bright,” he recited, “ ‘the first star I see tonight. I wish I may, I wish I might, have the wish I wish tonight.’”

Be careful what you wish for, Henry Howard.

Sitting down took effort. And coordination. And patience. His first attempt left him feeling impaled on a spike. Googling the average length of the teenage male rectum, he discovered it was 4.7” long. No wonder sitting on the dildo hurt. The shaft was 5-3/4” long. Still, he managed at sit without extreme discomfort because his rectum stretched, exactly like a woman’s vagina. Slouching was out of the question though, for the time being, anyway. He lit up the first joint.

It was excellent weed, filling his lungs with silky smooth smoke. He held his breath, letting THC absorb through his alveoli. It rushed to his brain and migrated across the blood-brain barrier, initiating a marvelous high. It also initiated the most achingly stiff hard-on he’d ever experienced. It was chrome steel, polished and pointing.

“Jesus God,” he moaned, writhing on his spike. “Please let someone fuck me tonight.” By someone, of course, he meant Charles, standing in for Dennis, who Henry had offered himself to countless times in his dreams. Charles, though ... who in his right mind would pass up fucking a tight rear end offered free of charge, he wondered. Boy’s, or no. Henry just couldn’t fathom that.

He took a second hit, and then a third. This was some exceptionally smooth weed, as well as incredibly potent. Henry wondered if hallucinations were in the offing. Powerful weed could do that, he knew, especially stuff laced with a hallucinogenic like PCP, mescaline, or acid. He eyed the joint, already bleary-eyed and loosing focus--mentally as well as optically. “Fuck...” he growled hoarsely. And then coughed. And then laughed.

Henry lived in a three-bedroom, luxury condo in Bethesda, MD. Mom worked because she chose to, coming from old money, which alone would support their lifestyle without either having to work a day. But Mom lived for her career as a registered nurse at the Suburban Hospital Trauma Center, while Dad pulled down 500 g’s a year with his consulting business. Not the richest family at Briarcliff, but certainly not paupers. The condo occupied the northeast corner of the 6th floor. The condos grew more expensive as the floors ascended, of course, culminating in the penthouse suite.

Henry was ensconced in the smallest bedroom, up front. Mom and Dad split the second bedroom evenly down the middle, Mom using her half as a home office/craft center, while Dad had converted his half into a man-cave, complete with 84” wide HDTV, and a fully-stocked fridge. Henry overlooked the main parking lot, and small in this case was a relative term: Henry’s bedroom measured 15’ x 18’, with its own bathroom and walk-in closet.

The rear balcony was the larger of the two, accessible from his parent’s bedroom and the shared 2nd bedroom. The main entry was via an enormous sliding glass door, situated between the two bedrooms for privacy. It overlooked a huge expanse of grounds, the connector road, and faced 6400 Briarcliff on a slant, affording more privacy. Four big condos made up the development, his and two others twenty stories tall, the smaller building, 6200 Briarcliff, only fifteen. The wealthiest residents resided at 6200.

He thumbed his phone and read 4:18 a.m. on the lock screen. The screen illuminated the front of Mom’s hiked up dress, his face, he assumed, and probably her wig. He pointed the screen downward to illuminate the tent in his purple panties; they barely hid his cock at all. His testicles and pubic hair were plainly visible below the hem, ditto the base of Mom’s dildo. He scootched on the tall shaft, grinning blithely. That felt so effing good. “I wish you had fucked me,” he muttered, meaning, of course, Charles. He would, had Henry been named Hailey.

He opened the weather app, checking on sunrise: 6:53 a.m. Approximately two hours of darkness remaining ... not so good. Not so good at all. Why the hell did he go back to sleep at one o’clock, anyway? How stupid.

He finished the joint and popped the roach in his mouth. He ground on the shaft, wriggling, shifting side-to-side, front-to-back, riding the intense discomfort and intensely powerful arousal it caused. He laughed hoarsely and then giggled, feeling all three types of queer. Training Bra queer, especially.

“I love sucking cock and fucking my ass,” he whispered loudly. “I’ll suck the first boy that rings my cell phone.” He lofted the iPhone with the screen displayed. He offered his cell phone number loudly, including the leading 1. No one called, though he waited patiently while smoking the second joint. He was so fucked up.

At 5:19 a.m., he snapped awake in the kitchen. His empty Heineken bottle sat on the counter next to the first; a fresh bottle was clenched in his fist, already open.

Blinking, he looked all around, wondering how he’d gotten there. The light was on, his boner had escaped his panties, the dress was hiked to his waist, and the thigh-hi’s were almost down to his knees. He felt behind him to make sure Edward was still there ... just barely, the head and maybe an inch of shaft still inside. He leaned and slid it back in to the base. That was too close, he thought irritably. Six effing hours, almost blown, just like that!

He turned sideways to the window to show his rigid little prick, still only 4-1/2” long and the thickness of his middle finger. God, how could it be so stiff and ache so hard? Please, he thought, let some guy with an 8” cock see me and want to fuck my tight little ass. Well ... semi-tight, he thought with a giggle.

He went to his room and lay over the bed rest again. He squeezed the shaft lovingly with his asshole, then with his rectum, moaning pleasurably. Why had he wasted so much of the night on sleep? Why hadn’t he done something sensible, like snap a selfie of himself in Mom’s full-length closet mirror and text it off to Dennis Chance.

Hi, Dennis, this is my twin sister, Hailey, who has a massive crush on you. We have no parents at home, and a refrigerator full of beer. I’ll drink myself drunk on the balcony, while you and Hailey get wasted on Mom’s excellent weed, and acquaint yourselves in her bedroom. Just ignore the decor. It doesn’t reflect who she is at all.

Chuckling darkly, he drained the rest of the beer, and then drifted off to sleep again.

He started awake. Why were the blinds open? Squinting, he looked at the bedside clock. Why did it read 1:12 a.m.? Grunting, he lifted up on an elbow and gazed around the room. He was no longer high as a kite, but still had Edward up his ass. He was no longer clothed in his mom’s underwear and dress, but completely naked. “Wha... ?” he grunted querulously. “What happened?”

He grabbed his iPhone and read the same time, tipping over to 1:13 a.m. as he watched. The date was Sunday, the 20th, so that was right. Why did the time read 1:13 a.m., though? Shouldn’t it be sometime around 6:00 a.m.? And why were the effing blinds wide open? Thank God the light was out, or everyone across the way would see him laying there naked, with a dildo up his ass. He reached around to make sure it was.

Struggling off the bed, he hobbled to the window and closed the slats. Turning on the bedside lamp, he scouted the floor and the furniture for his mom’s lingerie and dress; they were not in sight. When had he taken them off, he wondered? Where had he left them? Why did the clock insist it was effing 1:15 a.m. when he knew it wasn’t?

Also missing was the bottle of Heineken from his bedside table. Grabbing his cell phone, Henry shuffled from his bedroom down the hall to the kitchen. Everything looked in order. He opened the cabinet door beneath the sink and looked in the trashcan. The empty beer bottles weren’t there. Had he stashed them away in his room? Glancing at the window, he suddenly remembered he was bare-ass-naked with a cock up his ass and scuttled for the light switch. Many lights were visible in the building across the way, certainly more than would be lit at 6:00 a.m. on a Sunday morning. The kitchen clock insisted it was 1:19 a.m.

“What the fuck is going on?” he demanded of the room. “Did I dream all that?” Flummoxed, he returned to his bedroom and checked the trashcan there. Then he checked every other trashcan in the condo, determined to find where he’d stashed the bottles. There were none, anywhere. He’d blacked out, stashed the bottles away where no one would find them, not even himself? How stupid could he get?

“Asshole,” he muttered darkly.

As a last resort, he shambled angrily to the balcony door and peeked outside. The table was bare. He’d not left them outside, then. So where were they? And where were Mom’s clothes, her bra and panties, her cute little dress, her Fuck-me heels and her black wig? They had to be effing somewhere!

As it turned out, he found them exactly where he’d found them 2-1/2 hours before, in his mom’s dresser and closet.

This made no sense. The crotch of Mom’s panties should be badly soiled by the margarine he’d used to lube the shaft. Also pretty badly out of shape by the push/pull of his 2-1/2 hour love fest. Yet the pair in his hand was perfectly clean, smelling fresh out of the dryer. Also her bra, although he’d done little to affect the fit other than just by putting it on. The dress hung pristinely in the closet, and her stiletto heels sat neatly side-by-side on the floor. He eyed her wig atop the plastic head on her top shelf. It was perfectly coifed, exactly as before.

Completely bamboozled, Henry yanked out Mom’s stash box and stared at the dozen rolled joints sitting beside the unopened bag of weed. He counted to make sure: an even dozen joints.

Had that all been a dream then? Queering around in Mom’s clothes nothing but smoke and mirrors, the product of a diseased mind? He laughed, thinking how audacious this was.

One last place to check, he thought: Heading to the kitchen again, he opened the refrigerator door, found himself greeted by two full six packs of beer. That sealed it, then; he’d dreamed it all ... and he could do it again, for real.

He sat down carefully at the edge of his mother’s bed. It hurt just as badly as it had in the dream, working himself onto the dildo in Mom’s dress. He settled, shifting repeatedly, allowing his rectum to stretch as the head gouged his rectal/sigmoid elbow. Curious, he raised his cell phone and checked the Google app: no record of any search on rectum depth. Typing in the remembered search phrase, he was directed to exactly the same page he’d visited in the dream. It triggered the most intense feeling of déjà vu he’d ever experienced. He’d done this before. Just like he’d sat on the dildo earlier.

“Am I fucking crazy?” he asked the room.

This time he chose a pair of navy blue, satin panties and their matching bra. Mom’s breast shapers were back in the box in her bottom drawer, and again experiencing déjà vu, Henry removed them and reinstalled his baby breasts. Matching blue thigh-hi’s, and Mom’s auburn wig completed his accessories. The hair fluttering along his jaw line was pleasing. It reminded him of Scarlett Johansson in Lucy, though he wasn’t sure her character had red hair. Maybe the Avengers? He looked nothing like Scarlett Johansson, though. He struck a suggestive pose. “I’m yours. Come and take me,” he offered.

Mom normally wore pajamas to bed. She wore negligees for special occasions, he suspected, and that’s what he planned to wear, rather than her little black dress and stiletto heels. Returning to the dresser, he removed a shear blue number from the middle right-hand drawer and slipped it on over his head. He touched his thumping, aching cock through the sheer material; his scrotum felt shriveled like a prune. He so wanted to be the girl in the mirror instead of the unsuccessful boy he was.

In the closet, he grabbed the same two joints and Bic lighter from the stash, and beelined to the kitchen. It was 2:25 a.m. At the refrigerator, he grabbed a bottle of Heineken and spun off the lid. Distracted by the open window, it occurred to him that he’d spent a considerable time searching the apartment naked with a cock up his ass, earlier, including here in the kitchen. At the balcony door, too, before the open blinds in the living room, and the den. Now, he was parading around in Mom’s negligée, underwear, and thigh-hi’s.

In the dream, at least, he’d had sense enough to turn out the lights or close the effing blinds. He thought of the open blinds in his bedroom. Had they been open or closed in his dream? He would swear on a stack of bibles that he’d fallen asleep with the blinds closed. He shook his head, unsure.

He drank the beer in less than a minute and opened a second bottle, carrying it with him back to his bedroom. He wanted to suck his cock and wanted to see if that was possible with Edward up his ass. It turned out the answer was yes, the royal blue panties keeping it snugly in place while worked his erection ever closer to his mouth. He extended his tongue and flicked the tip, glancing at the clock for the time: First contact, 2:46 a.m. Thirty seconds later, he was eagerly sucking the head.

At 2:56 a.m., he glanced at the clock again for Milestone Number Two; his lips tightly wrapping the base of his cock. He laughed mutedly, lips and nose buried in his pubic hair. He closed his eyes, thinking, I am such a fucking pervert. No boy should do this. He should be sucking another boy, not himself. On his knees where he belonged, with Dennis’s fat cock in his mouth.

He unfurled, disgruntled. He had to go off card like that and think about Dennis Chance? Of all the boys in his 10th grade class, Dennis would be the last to unzip his fly for Henry. It wasn’t so much disgust that he felt toward his ex-friend, as consternation. He and Henry had been friends from 4th grade through the beginning of high school. During their first year, Henry had befriended and then gravitated toward Charles Groton, a student from another middle school with a taste for having his cock sucked. His friendship with Dennis slowly disintegrated over the next four months, until one afternoon after school, at Henry’s bus stop, a shouting match had occurred. Thankfully, the bus had gone on, and only a couple fellow students witnessed the verbal slugfest.