“My place isn’t far from here,” he said.
“Don’t you have a bunch of roommates?” she asked.
“Yeah, but they’re all out at parties. I guarantee you that the house is empty.”
She hesitated, but then she went along. Ray was going to get some action. He was going to lose his virginity. He just had to think of a way to document the milestone event. He carried the case of beer in one hand and he held Cass’s hand with the other. He dropped the beer by the front door as soon as they were home, and then they kept kissing. On their way towards Ray’s room, Ray tripped over a pair of shoes. He looked down and recognized Mason’s sneakers.
“What is it?” Cass asked.
“Nothing,” Ray said. Then he looked towards the kitchen and saw the cold medication that had been left on the counter. Mason must have stayed home with a cold. At first, Ray was worried. Then, he was thrilled. If he could make Cass have a loud orgasm, then he wouldn’t even need a picture! Mason could vouch for him—or maybe Mason would lie and say that he heard nothing.
They went to Ray’s room and continued their progressing romp. Ray got Cass’s top off and then he unclipped her bra with shaking hands. Her tits were perfect. He squeezed them, eliciting a moan from Cass’s soft lips. He realized his legs were trembling and probably close to giving out on him. So he lowered Cass down on his bed and then he climbed on top of her. He looked into her eyes and tried to figure out what she saw in him. Why wasn’t she rejecting him like every other beautiful woman? Why was she letting him crawl all over her and kiss her perfect lips? Did she have some serious self-confidence issues, or was Ray not as bad of a catch as he thought he was?
He heard a creak and looked over across the room. He could see the shadows of two feet standing on the other side of his closed door. Was Mason listening in? Was he about to try to ruin Ray’s night, or was he going to let Ray go on?
“What’s wrong?” Cass asked.
“Nothing. I just can’t believe how beautiful you are,” he said with a smile.
Her face turned red and they continued to kiss. With each passing minute, another piece of clothing hit the floor. Finally, Ray was in nothing but his boxers and Cass was in nothing but her panties. She looked down and saw his big erection trying to push out from its cotton prison. “You’re hard,” she said.
“I’ve pretty much been hard since we kissed on the pier,” Ray said, and then he realized how creepy that sounded. But she just laughed.
“Can I touch it?” she asked.
“Go for it,” he said, leaning back. Her fingers curled around his cock slowly. She didn’t go under the boxers—she was apparently saving that for later, letting the moment play out slowly with lots of anticipation. She got a firm grip and then she started to pull upwards.
“I can’t wait to get inside your pussy,” he said with a hot-faced grin. His heart was pounding.
Then she froze.
“What’s wrong?” he asked.
She looked into his eyes, and she looked worried, as if she just discovered something terrible—as if she just realized Ray’s dick was about to fall off, or that he had some sort of cancerous growth on his body. “Well? What is it?” he asked.
“I have to tell you something. I thought you knew—but now I’m starting to think that you don’t know.”
“What? What is it?” he asked, his heart pounding even faster. He couldn’t think of anything that would have put him off. She figured that she was about to tell him that she was lying about being a virgin, or that she was younger than she said she was originally.
“I wasn’t born like this,” she said. “I—I’m transgender. I thought you knew.” Ray’s ears started to buzz and his gut turned ferociously. “It says on my Facebook page. I assumed you read it.”
Ray didn’t read the information on her Facebook page. He was too enamoured by her pictures. It couldn’t have been true. She must have been fucking with him. “I—I don’t believe you,” he said, forcing out an awkward laugh.
“It’s true,” she said, pulling down her panties slightly, revealing the base of her shaft. She covered herself up quickly. “I’m so sorry. I thought you knew.”
And then he heard a door slam down the hall. “I’m not sucking your dick, you creep! You can go to hell!” A woman stormed from Mason’s bedroom down to the front door, and then she slammed that door too. For once in Mason’s life, he’d been rejected. And maybe that was his only prospect for the week. Maybe for once, Ray was going to beat Mason in Fuckeries—if he could go through with fucking Cass, despite her biological downstairs mix-up.
He managed to force a surprisingly genuine smile, and then he said, “I don’t care.” His voice was quiet as he was praying Mason wouldn’t overhear any part of the conversation. Surely the points wouldn’t count if Mason found out she were biologically male.
His heart was pounding harder than ever before.
“Really?” Cass said with apprehensive eyes.
Ray tried to swallow the thick lump in his throat, but it wouldn’t go down. “Really,” he said. He tried to force that smile again, showing lots of teeth. “I still like you.” A cold chill ran down his spine. He was going to go through with it, just so he could collect those sweet Fuckeries points.
CHAPTER VI
He climbed back on top of her and looked down into her eyes. Now, he could spot that slight bulge on the centre of her throat, and her shoulders did look a little bit broader than the average woman’s. And that slight rasp in her voice suddenly didn’t seem so sexy. But he managed to hold that smile anyway. “You really don’t care?” she asked again, as if his face was filled with reluctance.
“I really don’t,” he said. And then he leaned forward, closed his eyes, and pressed his lips against hers. His heart skipped a beat. He was kissing the lips of a man. It didn’t matter how many hormone pills she swallowed in her lifetime, or many surgeries she had—those lips were still the lips she was born with, and she was born a man.
Ray tried not to think about it but he could think of nothing else. At least she was a good kisser. At least those lips were soft and warm and comfortable against his—but in a way, that only made them more repulsive. He didn’t want to enjoy that kiss. He didn’t want to think that he could enjoy making out with a man. But he had to string her along if he was going to get those much-needed points. So he gently opened his mouth and accepted her tongue inside. He tried not to gag at the thought of that tongue belonging to a man—even a super-feminine man. His tongue was stiff as it touched hers. Now, in his head, he was counting down the seconds until this was all over.
He reluctantly put his hands on her naked body. At least her tits felt like tits. The implants were good—or maybe they weren’t implants at all. He squeezed them and found sweet refuge in her perky nipples. Though that thought still crossed his mind: those nipples belonged to a man.
She reached down and slipped her fingers under the waistband of his boxer shorts. Then, her fingers curled around his shaft. She started to massage and stroke. It felt good and horrible at the same time. Ray kept his eyes closed. He tried to imagine a woman, even though there was a perfectly convincing woman in front of him. Her hands felt small and fragile like a woman’s, but that wasn’t enough. It didn’t matter how small or soft or fragile or manicured those fingers were—he knew the truth.
“You’re big,” she said gently into his ear. And then Ray wondered how big she was. He only saw the base of her shaft and the bulge in her panties. What if she was bigger than him? And what exactly was she expecting him to do? If she sucked his dick, was she expecting him to suck hers? And if she let him into her tight asshole, was she hoping to get into his? He tried once again to push those thoughts away, focussing his attention on the pulsing euphoria growing between his thighs. He took a deep breath. His hands started drifting down her body, but he wasn’t sure how far to let them drift.
But he had to admit: her skin was soft—softer than a man’s skin should be. And the moa
n that escaped her plump lips as she squeezed his erection sounded feminine—no man should be able to produce that sound. Maybe she was hardly a man to begin with, even before the surgeries and the hormone pills. Maybe even before her transition she had been full of estrogen. Maybe she was one of those rare people who was born with both sex organs, and they just called her a boy for the sake of logistics… Or maybe Ray was just being optimistic.
She started to sink down beneath him. He held himself up on his elbows and knees, watching her go low. He watched as she pulled down his boxers, revealing his throbbing erection. He hated how hard he was—harder than he’d ever been in his life. But it wasn’t fair: she knew how to massage his shaft. Her hands felt too good.
She gently licked the length of his shaft and then she plunged his cock into her mouth. She closed her eyes and moaned gently as she bobbed her head up and down, pleasuring his whole length. “Shit,” her muttered. And again, he hated how good it felt.
And then it dawned on him that he was about to lose his virginity to a biological male. Was it worth it? They say that you never forget your first time. Did Ray want to remember fucking a man for the rest of his life? And when his future wife asks him: ‘What was your first time like?’ Was he prepared to lie to her? For the rest of his life he would have to live a lie: telling all of his serious partners that he’d never had sex with a man before. It would be a dirty secret, always lingering in the back of his mind. And would Cass’s face always be there in the back of his mind, teasing him?
He looked down and watched as she impressively sucked his swollen length while on her back. She was smiling, enjoying every second of it. She was losing her virginity too—unless she was lying. What if she told all of her partners the same thing? What if she’d slept with dozens of guys? What if she’d slept with traditionally gay men? What if she had a disease? Ray tried to push those thoughts out from his mind.
He looked over at his closet mirror. He could see her lower half. He could see that bulge in her panties: her erection trying to push out from between her thighs. She did a good job of holding it back with her legs, but it was still obviously there. Could she keep it hidden for the rest of the romp? Was she really not expecting anything from Ray?
Her eyes were closed while she was sucking. And Ray realized it was the perfect opportunity to get the proof he needed for Mason and the other guys. His phone was on his nightstand, just within arm’s reach. He made the move slowly, reaching out, gently pinching his phone between his thumb and pointer finger. He slipped it towards himself, using his thumb to hold down the ‘lower volume’ button, so that it wouldn’t make a noise when he snapped that necessary photo.
He didn’t look at his screen while he pulled open his camera—he did it by memory, swiping up and then tapping on that bottom left corner, where he knew the camera icon was. Then he gently tilted the phone down, pointing the lens at the beautiful blonde sucking his cock, and he snapped a photo. And the camera made a snapping shutter sound, making Ray’s heart skip a beat. He must not have held the lower volume button down for long enough—or maybe he missed. He became tense, with a lump as thick as a dinner roll lodged in his throat. He waited for Cass to look up with a face of disgust, but she wasn’t moving. She was still sucking as if she hadn’t heard a thing. Maybe one of her little slurps overlapped the noise. Maybe she just thought it was the floor creaking. Beads of cold swear trickled down the back of Ray’s neck, and he knew that he’d dodged a bullet.
He put his phone back down on the nightstand with a long, careful reach. And then he nestled his hands behind his head, so he could relax and enjoy Cass’s blowjob. It was only thirty seconds later when that swirling euphoria started to become overwhelming, making his legs tremble and his body squirm. “Wait,” he said. She looked up at him with big eyes, without taking his cock out from her mouth. “If you aren’t careful, you’re going to make me come.”
She giggled and then slipped his cock out, letting his bulbous tip rest on her chin. “I don’t mind if you come,” she said.
“Well don’t you want to—you know?”
She gently bit her bottom lip. “You want to fuck me in the ass?” she asked with a strangely shy voice.
Ray shrugged his shoulders. He didn’t want to fuck her in the ass because he knew that ass was no different than his ass. He knew that it would be hairy if it weren’t for the hormone pills she took. He knew that there was a ball sack just a couple of inches away from where he would be sticking his cock. But he also knew that anal was worth some extra points for the weekly game of Fuckeries.
Cass crawled out from underneath Ray. She rolled onto her stomach and then she carefully tugged her panties down over her butt, so they were resting on her thighs. She made another move with her hands between her legs, repositioning her male parts so that they were out of sight: a little courtesy for Ray, which he appreciated. But he still knew that cock and ball sack were hiding there.
He cautiously mounted her, planting his knees firmly on the mattress. He looked down at her soft ass, which was perky and smooth and soft and a little big jiggly. He carefully grabbed both of her cheeks and pulled them apart, exposing her puckering hole. His cock was already lubricated with Cass’s spit, so he was already ready for entry, but he hesitated, not sure if he really wanted to go through with it. Was it worth some free beer and a week of not having to wash dishes or do the laundry? Was it worth sacrificing his virginity? Her hole constricted and then opened again, as if she was inviting him in.
He looked up her body. At least she didn’t look like a man—especially from behind. She took care of herself. There wasn’t a single body hair to be seen, and her hair was soft and cared for. And even her face was cute—she had a lot going for her. So how bad could it be? Would the lifelong memory really be so haunting?
He grabbed his cock and pushed it down between her plump butt cheeks. He nestled his tip up against her tight hole and then he paused. He could still turn back. He didn’t have to fuck the pretty biological man that was lying on his bed.
He looked over and made sure his phone was within reach, and it was. Then he looked back at that puckering asshole. He took a deep breath and he pushed his cock down. It wasn’t as easy to penetrate as he thought it would be, but after ten seconds of squishing his cock downwards, it pushed through. She gasped and her hole tightened around his tip. He froze, realizing he was no longer a virgin. He was officially having sex for the first time—and he was ticking anal sex off the bucket list while he was at it.
“Oh God,” she groaned, squirming slightly. He used both of his hands to hold her firmly in place. He gently pushed in further, feeling his cock slipping deeper and deeper into her body. Her tight anal walls clenched his rod for a moment and then they relaxed. He watched as his cock disappeared between those plump cheeks.
“Does it hurt?” he asked.
“A bit,” she said. “But it’s okay. I can handle it.” Her voice was strained and focussed. It sounded painful, but he kept going anyway, determined to get his whole shaft inside of her—and determined to get the act over with. He sunk deeper and deeper and deeper as she groaned louder and louder and louder. Finally, Ray’s pelvis was pressed against her soft tush. He waited a moment for her body to relax before pulling back so he could do it all over again. This time he went faster—just a little bit, still being careful not to hurt her anymore than she already was.
Her fingernails dug into the bed sheets and she scrunched them hard. She had her face firmly planted into the pillow, and Ray realized this was probably going to be his best chance. So he reached carefully for his phone. This time, he opened up his camera and set it to video. He framed up her penetrated ass and he pressed record. Then he held his phone as steady as possible as he slowly pushed his cock deep and carefully pulled it out. He used his free hand to reach down and spread her cheeks, in case there was any confusion as to which hole he was fucking.
“Oh God, your cock feels so good inside of my little asshole,” she moan
ed. He was happy to get that line on his video. He kept recording his oblivious subject. Finally, he was going to win Fuckeries. No one would beat him. He had anal sex on camera, which had only been achieved once in Fuckeries history, by Mason of course. Maybe it would be Mason buying the beer. Maybe it would be Mason cleaning the dishes and washing Ray’s undies. How sweet would redemption taste?
Cass looked back suddenly. Ray tossed his phone aside as quickly as he could, and by some miracle, Cass didn’t notice. “Your cock feels so good in my ass,” she said again with a big grin on her face. “Fuck my little asshole. I want to feel your cum inside of me.”
He came down harder, his body suddenly pulsing with warm euphoria. He knew he wouldn’t last long in that tight hole. No man could possibly last long in that tiny hole—not even the most seasoned porn stars. It just felt too good, even when he was thrusting slowly, trying to make the moment last.
“Fuck me harder,” she said. So he held her tight and started to pound down harder. “Harder,” she said again, so he came down even harder and faster. He closed his eyes and bit down on his tongue in an attempt to suppress his orgasm. He knew it wouldn’t be long, but he also knew he’d only been inside of her for about two minutes. He didn’t want to prematurely ejaculate during his first time.
“Shit,” he muttered under his breath. He tried to think of something to delay his orgasm, but nothing came to mind—until he remembered that Cass was actually a biological male. That little fact had slipped away from him for a couple of minutes. But now, as he thought about it, it wasn’t helping to hold back his cumshot. He was still approaching his finale at a mile a minute. But he had an idea.
He reached a hand underneath Cass’s pelvis and her slipped his fingers around her erection, hoping it would take him out of the moment, so he could last longer. He felt Cass’s body tense up as if she wasn’t expecting the grab. And then he felt her relax. “Stroke me,” she said.
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