Coin Toss

by Matt2670

Copyright© 2019 by Matt2670

Erotica Sex Story: 16 year old Brandon loses a coin toss and discovers that losing isn't always for the worst. (This short story chronicles Andrew and Brandon's questionable get-rich-quick scheme, and how money isn't everything in the end. It contains a detailed, if not too graphic, scene with a sex toy, and a short sex scene between two boys. It is not for the homophobic reader.)

Caution: This Erotica Sex Story contains strong sexual content, including mt/mt   Consensual   Reluctant   Gay   Heterosexual   Humor   Anal Sex   First   Masturbation   Oral Sex   Sex Toys   .

Saturday, February 9, 2019, 10:16 pm

“Fuck!” Brandon complained bitterly. “I feel so fucking queer! This is so fucking queer, Andrew!”

Andrew shook his head and pinched his fingertips to zoom in on Brandon’s face. Brandon glared at him and raised a middle finger in protest. Andrew zoomed out again to include the obscene gesture.

“This doesn’t make us queer,” Andrew argued patiently. “All we’re doing is experimenting to see if this works. We haven’t touched each other, and we won’t undress at the same time. We only want to know if this part is doable for us, and if it’s sellable.”

Brandon blurted: “I’m the one experimenting, dammit! I’m the one naked with a—” He choked, unable to mouth the words. “And you’re fucking videotaping me!”

Andrew was stung. “The whole point, Brandon! What good is the whole business if I don’t tape you? We might as well be queer, just doing it to know how it feels! And we flipped a coin! It could’ve come up tails, Brandon! Do you want to stop?”

Brandon mouthed blistering curses and looked away.

Deciding that discretion was the better part of valor in this case, Andrew stopped recording and pocketed his cell phone. He was glad that Brandon had lost the coin toss, and not him. He also felt guilty about it.

The experiment hailed back to an incident 2 Saturday’s ago. Brandon has spent the night, and sometime after midnight, Andrew stumbled upon a video on PornHub that neither boy would expect to watch. A video no heterosexual boy would watch.

“Is that... ?” Blinking, Brandon leaned closer to the iPad and studied the girl on her knees, riding a tall white dildo. They’d been on PornHub since 11 pm, and had watched girls fucking, sucking, jacking, masturbating, getting butt-fucked, riding dildos, and eating other girls. Andrew chose the current video from a selection of similar offerings under the main screen. The previous video had 2 girls sharing a dildo. This girl was solo, only...

“Jesus!” Brandon spat. “That’s a guy!”

He looked like a girl, with long blond hair back in a ponytail, a delicate body with small round breasts and a narrow waist, shapely legs and a perfectly flat belly. It struck neither boy as particularly odd that she wore panties. She’d pushed them down in the back in order to ride the tall white dildo with her asshole. Only, it was HIS asshole riding the shaft.

“Fuck!” Brandon hissed disgustedly. “You gotta be kidding me! What’s a queer doing on the straight side of the site?”

Andrew shared his sentiment, if not his belief that PornHub religiously segregated straight videos from queer. Honestly, the tranny kinda intrigued him. Especially her nearly flat chest. Female hormones hadn’t done a lot for her in the breast’s department, although she looked quite feminine, otherwise. “He’s a tranny,” he said. “She’s a tranny. He just hasn’t had surgery yet.”

Brandon glanced at him disgustedly. “Who cares—it’s fucking gross! Get him outa here, dude!!”

Shrugging, Andrew did as his friend asked.

Unlike the vast majority of 16-year-old boys, Andrew and Brandon privately admitted to masturbation. This became necessary 4 months ago, a week following Brandon’s 16th birthday. Andrew had turned 16 the week before, and it was another overnight stay at Andrew’s house. Watching porn was always difficult when you couldn’t acknowledge how badly you wanted to pull out your pecker and beat the living crap out of it—or even admit such a possibility existed. Boys just didn’t admit to wanking their wieners.

“Fuck!” Brandon hissed as he and Andrew watched a cute mom getting boned in her ass by a huge BBC. He shifted angrily. “This is so fucking frustrating!”

Andrew gazed at him mutely. He knew exactly what Brandon was angry about, but wouldn’t open his mouth.

“Can I just come out and say it?” Brandon blurted.

Andrew feigned ignorance and shrugged.

Frustrated, Brandon just put it out there: “It drives me crazy to watch porn videos and pretend I don’t want to beat off! Why can’t guys just admit they beat off? Why is it so fucking taboo to admit beating off? Don’t you dare fucking deny you beat off, or I am outa here right now, Andrew!”

Fiercely daring Andrew to deny it, but giving him no time to answer, Brandon blundered on.

“I beat off! I beat off every fucking time I’m alone and watching videos or looking at pics. I beat off Thursday night watching a girl get her mouth fucked, and then put up her ass, doggie. I beat off after school Wednesday looking at hacked pictures from The Fappening. I dare you to tell me you don’t beat off, Andrew! Admit it!”

Andrew gulped. Faced with Brandon’s rage, frustration and self-righteous outrage, he still couldn’t admit to beating his meat. It was too humiliating.

“You fucking asshole!” Brandon shot to his feet and bent to grab his shoes. “If you so much as open your mouth about what I said tonight, I’ll beat your ass in front of the whole school, Andrew!”

Tongue-tied, he let Brandon get to the bedroom door before blurting: “OK! I do! Not very often,” he lied, “but I do it sometimes.”

“Fuck you!” Brandon said hotly. “Lying sack of shit!” He yanked open the bedroom door.

“OK! OK! I do!” he whispered harshly. “Shut the fucking door, will ya!”

Brandon did. “I do it all the time. It humiliates me to say it, but I’m sick of this shit. I want to beat off when I watch a porno video. Can we just agree to do that from now on?”

Red-faced, Andrew nodded. It would be fucking humiliating to pull out his cock in front of his best friend, but God, what a relief it’d be too. He hated this macho-manic denial of facts. Every boy beat off. Every boy lied about it, too. It wouldn’t stop him from feeling like a faggot, baring his cock in front of another boy and beating off, but how fucking liberating!

He cleared his throat. “What do we do about ... coming?” He couldn’t believe he got the word out without choking on it. Even Brandon looked cowed.

“I don’t know. I guess we either agree to do it... ?” He phrased it as a question, to which Andrew eventually nodded agreement. “It doesn’t mean we have to do it, though.”

Andrew shook his head.

Removing your cock and beating off in front of your buddy is torture the first time, for both involved, but 4 months later, Brandon and Andrew barely broke a sweat unzipping and pulling out. Repetition—and an avowed agreement that masturbating didn’t make you queer, and nothing queer would ever come of the act—put them at ease, making them unique among 16-year-old boys. Neither believed other friends at school had made such a breakthrough. One reason, I guess, that Brandon ended up nude on Andrew’s bed that Saturday evening in February. But that’s getting ahead of ourselves.

Andrew found a young blonde giving her boyfriend an arousing, if inexperienced blow-job in the front seat of the car while he drove the streets of a residential neighborhood. Brandon and Andrew gingerly beat off to her oral effort, careful to keep arousal in check. Practicing restraint turned out to be an unexpected side-effect of masturbating together. You needed stress relief, not an excuse to cum. Restraint proved more difficult than expected for both.

“Jesus, she is so fucking cute!” Brandon gushed. “I love her mouth. Give me that fucking mouth.” Over the course of 4 months, they’d also overcome most restrictions on saying what they wanted to about guys, and their anatomy. “Think he ever had a guy suck his cock?”

“I’d suck it if I were gay,” Andrew deadpanned. “Watching her suck makes me super fucking horny, Brandon.”

Brandon guffawed. Then glanced at Andrew curiously. “The guy on the dildo... ? The tranny blonde. What do you think that felt like up his ass?”

4 months ago, neither boy could possibly ask such a question.

Andrew shrugged. “Don’t know. Rhetorically, I’ve always wondered if I would like it, or not. You?”

Brandon slowly stroked his cock. Finally, he nodded. “I’ve never done it, though. You?”

He and Brandon no longer dodged embarrassing questions, or lied. A month ago, both admitted a profound curiosity about each other’s cocks, if they’d enjoy sucking them. Remaining honest, both admitted they probably would. It went without saying, however, in the interest of remaining good to their word, and preserving their friendship, neither would consider such a thing.

Andrew said: “Doing that would be so queer. I don’t do queer. Neither do you,” he added. “But what if doing that—” He back-arrowed to the video of the blonde tranny. “What if doing that wasn’t to have fun, but to make money?”

Brandon blinked and cocked his head. “What do you mean, make money?”

“That guy—” He pointed at the screen. “—is obviously 18+.” Also seriously cute, he didn’t say. “You have to be 18 to post a video on this website. Any commercial site, you know? It’s the law.”

Brandon nodded slowly. “There’s other places to post a video if you want to break the rules, though.”

“And make big money,” Andrew added.

Brandon nodded slowly again. Experimenting with a big dildo wouldn’t be queer if done solely in the interest of money. End justified the means where getting rich was concerned, he thought. No stigma involved; you did whatever necessary in pursuit of the endeavor.

“We could live stream ... there’s guys out there willing to pay big bucks to watch young boys riding a pony,” he said. He made sure Andrew understood the plural nature of ‘boys’. “We could do other things for them, too, if they paid for that.”

Andrew smiled wryly at his friend’s cautious words. “Let’s concentrate on baby steps first. Riding a pony, and work up from there.”

Securing a pony was difficult in concept, remarkably easy in practice. Online, Andrew & Brandon scoured the offerings, were dumbfounded at the immense variety of ponies offered: all sizes, shapes, and colors. Confused and frustrated, in the end they chose a dildo most like what the tall blonde tranny rode in her video: white, 9” overall height, with a 7-1/4” insertable shaft. The head measured 1-1/4” across, as did the shaft at the base. It stood upright, tall and proud, ready for mounting.

“Buy two,” Brandon said meaningfully. Andrew blushed at the suggestion, understanding Brandon’s implication: this wouldn’t be a one-boy pony-show if it sold. He battled the image of he and Brandon riding their mounts, side by side for the camera.

The site accepted Visa, Mastercard, American Express, and Discovery. It surprised Andrew that they also accepted PayPal. Entering his number to complete the transaction, he ordered the twin dildos and 4 tubes of KY lubricant. Brandon snickered and shook his head. Fucking Andrew was brilliant: 16 years old with an illegal PayPal account.

“Where do we deliver it, though?” he asked.

Andrew shrugged. “It’s 2 days free shipping, so it’ll come sometime Monday. Wanna come here after school?”

Brandon nodded slowly. “Jesus. I can’t believe we’re actually doing this.” From hesitant talk, to buying 2 embarrassingly huge dildos, in less than two hours, he thought. He glanced away, imagining doing what the blonde tranny had done. Could he actually do that? Could Andrew?

“I feel so fucking queer!” he repeated hotly. “This is so fucking queer, Andrew!”

Andrew winced and shook his head. “You should stop, then, Brandon.”

Brandon bared his teeth and cursed in furious embarrassment. 2 weeks of discussion and research and it came down to him sitting naked on Andrew’s bed, astride a 9” tall dildo. The head was inside him, clenched tightly by his protesting asshole. He refused to settle farther onto the shaft and have it penetrate into his rectum. The whole point of the exercise, or fucking not—fuck if he’d do that!

“How’s it feel?” Andrew asked softly.

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