The Boifriend Ch. 01

[pre-story]Content Warning: SUPER gay. Crossdressing. Sissy self-deprecation. There's going to be some unrealistic anatomy later on, huge cock, huge balls, and huge loads.

Disclaimer: All characters are 18+[/pre-story]

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The Boifriend, Chapter 1

"Whelp!" Leo exclaimed as he stood up and gave an exaggerated stretch, feigning a yawn. "Looks like it's time for me to hit the sack."

Ann smirked playfully at her father, the dark-haired teen adjusting her glasses, the light from the tv screen glaring off the lenses for a moment. It was remarkable how much she looked like her mother in that moment, she had the same look on her face he'd seen her mother wear so often, the kind of amused, knowing, too-smart-for-her-own-good look. "So soon, daddy? The movie's just starting. I guess age really does take it out of you..."

Leo smirked back and shook his head. "Ah, I've seen it before." He replied with a dismissive wave, then leaned down, quickly kissing his daughter on the top of the head before straightening up. "Besides, you 'hep cats' don't need an old man 'harshing your groove'." He added, making liberal use of air quotes.

Ann laughed, shaking her head. "Oh my god, even YOU aren't old enough to have used 'hep cats'."

"Um, goodnight, Sir." Ben managed to speak up, though he couldn't quite make the eye contact to go with it.

Leo gave a soft smile and turned on his heel. "You kids have fun." He added, heading for the stairs. He hesitated a moment as he gripped the railing and mounted the first step, glancing back to the pair on the couch, already wrapped up in a hushed conversation, then shook his head and started to climb.

All Leo could think about as he headed for his room was that blue hair.

Who dyes their hair blue? Maybe Leo was just getting old, but when Ann first brought Ben over to the house, he couldn't help but think the kid looked like a wimp with that hair. It wasn't even a deep blue, it was a sort of light blue-green. Aqua, Ben had later clarified, before elaborating that he'd chosen it because he thought it would compliment his blue eyes. He wasn't wrong, the kid had big, bright blue eyes, and he was also pale-skinned, short, and skinny, too, with no facial hair and almost no muscle to speak of, a real pretty boy type. He could imagine the kid might be popular with the ladies, if it weren't for his almost painful shyness. Ann assured him Ben was really a lot more talkative when Leo wasn't around, and she definitely would know, considering they'd been best friends for years. When he'd asked if Ben was afraid of him or something, she'd just smirked and replied 'something like that'.

Leo had to admit, he felt bad for the kid. Back when he was in school, looking like that would have gotten your ass kicked daily. Back when he first started coming over, it wasn't too far from the reality of the situation, either, judging by the bruises Ben so often had. It got so bad that Leo even gave the kid a free membership to his gym, to try and toughen him up a bit. But the whole time he was there, he'd just seemed painfully uncomfortable, and when he stopped coming after a couple weeks, Leo hadn't pushed the issue.

It was understandable. Leo was pretty much the kid's polar opposite in a lot of ways. For one thing, be was black- technically more like a warm terracotta brown, if Ann's fashion assessment was to be believed, with short, curly, black hair and a short beard he kept neatly trimmed. Leo had always been a big guy, but it was mostly fat, at least until high school, when he started lifting. Now, he was 6'4" and 300 pounds. Now, he wasn't exactly ripped and bulging like a bodybuilder, but nobody would dare call him fat. There was no denying the layers upon layers of steely muscle he'd been training for the last twenty years, the arms thick as a man's thigh, the barrel chest with great, slab-like pecs and a thick layer of dark, curly hair. He'd been a professional powerlifter for a while, before... before he'd had to settle down and take care of Ann.

It had taken Leo by surprise when Ann announced she and Ben were officially dating. Maybe he just didn't want to believe his little girl was growing up and liking boys, but Ben didn't exactly seem to be her 'type', if the action hero posters on her walls were any indication. Still, they seemed pretty happy together, Ben especially, and they hung out all the time, both before and after the announcement. According to Ann, at least, the bullying had eased off. Perhaps it was because dating Ann provided evidence of his straightness, or perhaps it was just because Ann had broken one that one linebacker's jaw when she found out he'd shoved Ben into a locker. Leo had had to work real hard to talk the principal down to a suspension after that incident...

Tonight was a big night for the young couple. After much begging and bugging from Ann, Leo had finally given in and agreed to let Ben spend the night. He'd been more than a little apprehensive about the prospect, but in the end, he knew he could either let it happen and make sure they were being safe, or they'd just sneak off and do it somewhere else. Ann was already on birth control for cramps, but he'd left a box of condoms on her bed yesterday, just to be safe. As he climbed into bed and peeled off his shirt, he couldn't help but feel... bitter. Some primitive part of his mind felt like he was surrendering, giving his little girl over to be devoured by some weakling who wasn't man enough to deserve her. But no, he reminded himself as he rolled over to his side and closed his eyes, Ben was a pussycat compared to Ann. If anything, it was Ben who was gonna be devoured...

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Leo was in a hot tub that was also the ocean, with a pair of voluptuous mermaids swimming toward him, when he heard a soft, disembodied voice ring out. "Sir?" It asked, and he grunted dismissively, rolling a shoulder to shake off the weight that had settled there, gripping his sheet- Wait, where'd the sheet come from? It was too late- the emerald-skinned mer-babes were already getting hazy, the hot tub falling apart around him, water draining into nothingness. "Are you awake?" The voice asked, and the dream collapsed entirely, leaving Leo lying there in his bed.

"Mmmh, 'M up-" Leo muttered, rolling onto his back, blinking blearily to try and clear his vision, only to realize there was nothing to see- the room was completely dark, the only light the faint, silvery moonlight coming through his blinds. How long had he been asleep? "Wha's-?"

"I- I need to talk to you, Sir." The voice said, and Leo realized it belonged to Ben. His tone was serious, too...

"...Arright." Leo mumbled his reply as he sat up on the edge of the bed and reached for the lamp on his nightstand. "What's the-" He began, only to stop abruptly as he felt a hand close around his wrist.

"Just- please, just wait a second before you turn on the light." Ben urged.

Leo's brow furrowed with confusion, both because of the odd request and the fact that Ben had actually physically stopped him from doing something, which was... uncharacteristically assertive. The boy always seemed to be walking on eggshells around him... So if this was serious enough to warrant that, he might as well hear it out. "...Alright, then. What's this about?" Leo finally asked, letting his hand come down to rest beside him.

It was far too dark to make out any sort of detail, butLeo could at least make out Ben's presence beside the bed as he shuffled awkwardly for a moment, before taking a deep breath and letting it out with a sigh. "Ann- Your daughter and I, Sir- we're not really... dating." He eventually managed. "It's more like she's... covering for me... If you get what I mean." He elaborated, voice strained.

Leo's brow furrowed, the gears in his mind grinding to a halt as this new information fell into the machinery like a stray wrench. The stray thought rattled around in his skull for a moment before he recognized it as not a wrench, but a cog! "Oh. OH!" Leo muttered as the new cog clicked into place, sliding perfectly into the clockwork, the missing piece that fit into the mechanism related to the ongoing question of Ben. The gears chugged into motion once more, and finally, the Ben mechanism turned smoothly, no strain, no hitching, no grinding...

"So... You're- it's 'gay', right? That's the right word?" Leo asked. His eyes were beginning to adjust to the darkness, at least, enough to see the boy nod. He caught a glimpse of something shiny at the boy's ear... and he thought he saw a gleam at his chest, too. "Good to know. So, uh... Well, I want you to know I support you. I don't think it's wrong or immoral or anything, or that you're going to hell, it's just part of who you are, and you're a good kid. Your secret's safe with me. And if you ever, like, help with something, or to talk about it, I'm here." He offered, trying to sound more prepared for this than he actually was, then paused, blinking. "Wait, then, is Ann..."

Ben shook his head. "No, Sir. She's definitely straight. It's, um, kind of a- a 'common interest' for us, you know?"

Leo nodded. "Okay. Good. I mean- not that there'd be anything bad if she was, just..." He rambled on for a moment. It all made so much sense now. This was why he'd never seen the two kiss, the reason their dates didn't seem exactly romantic... Who goes to see 'Dance of Death 3' on a date? "...Wait a minute. Have you two been just hanging out and calling them 'dates' to get around her curfew?" Leo asked, narrowing his eyes at the darkness.

The shape in the darkness shifted, uncomfortably. "There's- There's one more thing, Sir." Ben said, abruptly changing the subject. "O-or maybe... show you?" He added, his voice trembling for a moment. There was a moment's pause, then Ben spoke again, his voice a little more resolute. "You- you can turn on the light, now, Sir. If- if you want."

Leo wasn't sure what he was expecting when he reached over to the bedside lamp and flicked the switch, but it certainly wasn't what he saw when the lamp lit up the room. Ben stood there, a few feet back from the edge of the bed. His aqua-blue hair, jaw-length on top and shaved close on the sides, was swept to one side, falling down over his face like a waterfall, half-covering one of the boy's big, bright blue eyes. His eye makeup was expertly applied, dark blue at the outer corners, then fading toward the center to electric blue, then finally a pale, almost-white-blue at the inner corner, sparkling glitter spread all throughout. His cheeks were contoured and dusted with blush, silver stud earrings gleamed in his earlobes, and his lips were painted the same aqua as his hair, the color rich, smooth, and glossy. His front teeth sank into the lower lip slightly as he nervously stared at Leo, trying to gauge his reaction.

Leo's gaze roamed down from ben's face. He was barely dressed, the a cropped tank top of transparent turquoise mesh leaving nothing to the imagination. His chest was slender and smooth, either shaven or hairless, he couldn't tell, but his dime-sized nipples were pierced through with a pair of gleaming silver barbells. The short top left his stomach exposed, slim and supple, only a hint of muscle underneath the soft, smooth skin. His nails were painted to match the rest of his theme, aqua blue. Leo's eyes went further down, and found the teenage boy's lower half clothed in a pair of long, aqua-blue thigh-high stockings, trimmed in white, lacy frills and connected to a matching garter belt. His modesty was preserved, though barely, by a pair of lacy, blue-green panties, an obvious bulge in the material as they tried to contain what they were never meant to. Looking even further down, Leo could see he tottered on a pair of tall stiletto heels, to complete the look.

"I'm a- a perverted, crossdressing sissy, Sir." Ben announced, drawing Leo's gaze back up to his face. "And I... I want to be... your bitch. I want you to- to MAKE me your bitch. P-please, Sir, you don't have to worry about my- my penis, you don't have to- to touch it, or anything, it doesn't matter, I just- I just want to- to worship your cock... a REAL man's cock. It would be so hot... you're so- so strong, and- and manly and... BIG... Oh, god, I haven't been able to forget your cock since I saw it in the showers... I just-" Ben rambled, his expression pleading, rapidly growing desperate. "Please, Sir, I- I don't even know if- if you LIKE guys, but I- I promise I'll do good, I'll do- do anything you want, ANYTHING, I swear, I- I can just- just suck you while you watch porn, you can even- even sell me, Sir, I- I'll make sure they wear condoms and- and bring you all the money, just- just let me- Oh god, this- this was a huge m- mistake..." He whimpered, his voice faltering as he began to tremble. "Of- of COURSE this wouldn't work, I'm so STUPID, I just- I wanted it for so long, I thought if- if I showed up like this, you might- you might... use me..." He hastily tried to explain, knees turning in as his hands moved to cover himself, tears beading at the corners of his eyes. "I'm so sorry, please, please don't hate me, Sir-"

Ben went abruptly silent as Leo suddenly rose to his feet, his massive, muscular frame looming over the younger boy, a wall of earthy brown muscle, arms like tree trunks reaching toward him with rough, calloused hands that looked like they could snap his neck without even trying... He flinched in fear, squeezing his eyes shut, only to feel those massive, rough hands land on his shoulders, gripping firmly. He froze for a moment, before cracking his eyelids open, those big blue eyes slowly following Leo's thickly muscled arms up toward Leo's, his expression uncertain and afraid, only growing more so as they found Leo's chiseled face unreadable.

Leo leaned down until his lips were at the boy's ear. "We are going to have a long talk about this, boy." He half-whispered, his voice deep and rumbling, his tone leaving no question in Ben's mind that this was not a suggestion. "But in the meantime... I think I can put that mouth to a better use." He added, and suddenly, Ben felt the hands on his shoulders push, hard. His legs buckled in an instant, and he fell, landing heavily on his stocking-clad knees. The carpet softened the impact somewhat, but it still hurt. The pain was swiftly forgotten, though, as the sheets that had still clung to Leo's hips fell away, revealing the tight black boxer-briefs he wore, and the truly massive bulge contained within.

Ben swallowed, nervously, as his eyes locked on Leo's bulge. "...Yes, Sir." He muttered. The shape twitched under the fabric.