So he started stroking her. And it worked for a moment, taking him out of his horny sex daze, slapping him back into reality. But once he started stroking, that horniness came back. He kind of liked the way her cock felt, throbbing in his hand. He liked how hard she was—it was nice to know that he was the one who made her that hard. And he liked how she was suddenly squirming and moaning, as if she was about to come. If she came first, then he didn’t have to be embarrassed about ejaculating too quickly.
So he tightened his grip and started pumping fast. “Oh God. Oh fuck. Shit!” Cass said, planting her face into his pillow. Ray reached up to massage her tip, but it was already enough. She exploded warm cum into his hand and onto his bed sheets. “Fuck! Oh God!” she cried. He let a few blasts pool up in the palm of his hand, and then he smeared her warm goo down the length of her shaft. She looked over her shoulder at him and smiled—and that smile was all he needed.
His cock twitched and his body shuddered, and then he started to fill her tight hole with his hot substance. He dug his nails into her skin, but she didn’t mind. He came down hard, shoving his entire shaft into her body. She screamed, but she liked it. He didn’t pull out until every last drop was deposited inside of her, and then he watched as her gaping hole slowly pushed out his creampie. It billowed out in globs and disappeared between her thighs, to roll down her swollen ball sack.
Ray stumbled back, onto his feet. His head was spinning. Reality slapped him hard: he just lost his virginity to a biological male. He just came in a matter of minutes inside of a boy’s asshole. And worse: he just jerked a tranny off, and that cum was currently all over his bed sheets. And was it worth it? Was a single week of pride worth that dirty secret he would now be carrying around with him for the rest of his life?
“So can I sleep over?” she asked.
Ray hesitated. He tried to think of a way to kick her out, but he didn’t want to be rude. He bit down on his tongue and just tried to say ‘no’, even without a good reason, but he just couldn’t bring himself to do it. “Sure,” he said, forcing a smile.
Cass smiled. She stood up and kissed him on the cheek. And then she reached down and pulled up her panties, but Ray had already seen everything out of the corner of his eye: her slumped cock with a drop of cum hanging off of her tip. He’d jerked that dick off. He still had her cum smeared on the palm of his hand. “I just need to take a quick shower. You don’t mind, do you?” he asked.
“Mind if I shower with you?” she said with her cute smile. And again, Ray didn’t have the heart to say no.
It was awkward, standing in the shower with her, trying to keep his gaze up and away from her dangling cock. She was big—not quite as big as he was, but bigger than any woman should be. When she bent over to scrub her legs, he caved to the urge to take a peek at that cock, just to make sure it was really real and not just some kind of joke. But it was real, and he really had jerked the cum out of it.
She spun around and looked him in the eyes. She had a bit cute smile. “I can’t believe I’m not a virgin anymore,” she said.
Ray forced a smile. “Me neither,” he said. At least her smile was cute. At least she was beautiful. Hopefully that was a piece of information he would remember. Hopefully that cock wouldn’t be the only thing that stayed in his mind after the night was through.
She leaned forward and kissed him on the lips. He kissed back after a moment of reluctant hesitation. He didn’t want to hurt her feelings. He knew that this moment was special for her, the way it should have been special for Ray. He could wait until the morning to figure out a way to let her down easy—hopefully without breaking her heart.
He didn’t get a lot of sleep that night, constantly replaying that terrible moment when he realized he was about to have intercourse with a man. Cass, on the other hand, slept like a newborn baby. After cozying up against Ray’s body, she was asleep within minutes, her naked bum nestled against his naked pelvis. He tried to not enjoy it, but he couldn’t help but succumb to the soft, warm comfort of her perky ass a few times throughout the night. But that comfort would only last a couple of minutes before he remembered reality. And then he would have to will his erection away, which kept finding itself nestled between her plump butt cheeks. The last thing he wanted was to wake her up with her boner and make her think he wanted a second round. If he fucked her again, then he knew there would really be something terribly wrong with him. Once was more than enough. He had the points he needed—now he just had to figure out a way to clean up the mess.
CHAPTER VII
Before Cass left in the morning, she said, “When do you want to meet up again?”
Ray forced the biggest smile he could and said, “Soon. I’m pretty busy this week, but I’ll let you know as soon as I’m free.” But he had no intentions of reaching out to her ever again. His plan, unless he came up with some perfect split-up message to send to her, was to cut off contact and hope that she never came around the house. It was unfortunate that she knew where he lived. It was easy enough to ghost her on Facebook and ignore her messages on Tinder, but if she came to the house, ignoring her wouldn’t be so easy.
So when she was walking away from his house, he hoped it would be the last time he ever saw her. Though as soon as she was gone, he felt an empty feeling, as if something was suddenly missing. It was too bad that she wasn’t really a woman. It was too bad that she didn’t have a pussy or the ability to have a child. It was too bad that the first beautiful woman to be attracted to Ray wasn’t a woman at all.
He knew he would probably never get with a girl as pretty as Cass ever again. In a way, he knew it was downhill from here—but at least the next girl would be a real girl.
He still had a day before the awards ceremony for the week of Fuckeries, so he still had time to rack up some points. That night, there was a big party just down the street. Ray thought about going, maybe just to kiss a girl to add another point to his tally, to ensure his victory, but he decided to stay home when he saw that Mason wasn’t going out. He was still sick with his cold, which had worsened throughout the day. Ray was fairly confident that he had the week won, for once in his life.
When he went to sleep that night, that strange empty feeling returned. His bed felt cold and he kind of missed the feeling of Cass’s warm bum pressed up against his pelvis. She may have technically been a man, but she sure felt like a woman. And she smelled like a woman too—she smelled better than all of the girls Ray had ever kissed. But what difference did that make? Anyone could go out and buy some fancy perfume and women’s deodorant. Hell, even Ray could go out and spray himself with perfume if he wanted to—it didn’t magically turn him into a woman. Getting breast implants and an Adam’s apple reduction also wouldn’t turn him into a woman—and neither would some pills designed to alter which hormones came out from which organs. It was all just a disguise. Cass was just a man in disguise, and no matter how Ray tried to rationalize it, he knew that was the truth.
It was the next morning, shortly before the Fuckeries awards ceremony, when Cass sent Ray a Facebook message. “How was your Saturday? End up doing anything fun?” she asked. Ray made a point of leaving the message marked as unread. He clicked the little X in the corner of the chat window and decided he could live with the red dot in the corner of his browser screen, reminding him that he was ghosting the most beautiful woman he’d ever kissed, and the only woman he’d ever fucked.
Though while he waited for Mason, Aaron, and Paul, he couldn’t help but consider the possibility of replying to her. Maybe he could just find a way to wean her off gradually. Maybe he could chat with her a bit—less and less everyday, until she lost interest and moved on to another guy. Maybe he could cut her off without hurting her. Hell, maybe they could even be friends. He looked at that message again, but decided to leave it alone. He figured it was best to stick to his original plan: cut her off cold turkey. That empty feeling inside of him would go away eventually.
Paul came downstairs looking tired, a
nd then Aaron came down with a big pair of sunglasses on. “What’s with the shades?” Paul asked. Aaron lifted them up, revealing a big black eye.
“I was fucking a girl from behind and then she looked back and saw that I was filming her. She turned around and socked me in the face. Bitch hit hard too. I had to go to the doctor and everything.”
Paul laughed, and then Aaron couldn’t help but laugh with him. But Ray couldn’t figure out what they both thought was so funny. That poor girl, obliviously being filmed for some stupid juvenile game. Aaron’s date probably thought that there was a connection between Aaron and her. She definitely didn’t know she was being used, with no regards for her feelings whatsoever.
“Well at least you got some proof. I tried to open up my camera while this chick was sucking my cock, and then she immediately stopped—left me with blue balls. I got a picture of her storming out the room with her saliva hanging off my dick, but I have a feeling Mason won’t count it.” He laughed, as if he’d said some sort of joke—and Aaron laughed with him. And maybe the joke just flew over Ray’s head. Was that all this game was? Taking advantage of girls for some imaginary points?
The guys looked at Ray, as if they were waiting for his story. Ray forced a smile—his story wasn’t so much different than theirs. He wasn’t any better than Aaron with his black eye or Paul with his blue balls. He’d used a woman in an attempt to win Fuckeries. The only difference was that Ray wasn’t laughing. Though maybe he should have been. Maybe laughing would have made the harsh reality easier to handle.
Mason came down before Ray had to go into any details. “Let’s get this over with,” Mason said with a grunt as he sat down on the couch and pulled out his phone. He quickly pulled up a picture of him getting his cock sucked. “I fucked a girl too, but my phone was dead so I couldn’t get a picture.”
Ray looked closely at the photo. When was it taken? The girl from the other night stormed out, refusing to suck his dick, and he’d been home sick since then. So was the photo from earlier in the week? The floor in the picture was definitely his bedroom floor, but Ray didn’t remember any girls coming by—unless she came by while he was at work.
But it didn’t matter. Ray had him beat for once. But he wasn’t ready to prove it just yet.
Aaron showed the picture of the girl sucking his cock. “I guess we tie this week,” he said with a laugh. “I would have gotten more had I been a little bit more careful—but what can you do?”
Then Paul shook his head. “I got nothing this week. I guess I’m tied for the lose.” He looked over at Ray while shrugging his shoulders. And why would he assume that Ray had nothing? Ray had kissed a handful of girls before—just the last week, Ray had proof that he kissed a girl. So was it really so hard to believe that he could have kissed a girl for a second week in a row.
He pulled out his phone with a big grin on his face. He opened up that video, of his cock buried deep in Cass’s asshole. And then he hesitated. He knew it was enough to win—he didn’t even have to show the picture of her sucking his cock. But did he want to show that video to these cavemen? Was it really worth a week of no dishes and no laundry, and some free beer?
He bit down on his tongue and flipped his screen around, pressing play for his roommates to see. He felt his cheeks turning red while the guys ogled his video. “No way,” said Mason. “I don’t believe it. That girl’s actually hot. There’s no way you got with an actually hot girl.”
“Well, I did,” Ray said.
“How do we know that isn’t some video you downloaded off of a porno site?” Aaron asked.
Ray looked at the video and then back at the guys. “It’s clearly my bedroom,” he said.
The guys watched the rest of the video with apprehensive looks on their faces. Then, after a long moment of silence, Mason said, “Well shit. I guess Ray wins this week. Paul—you’re buying the beer and doing Ray’s chores.” He looked at Ray with a half-grin, as if he really didn’t believe the video was real, as if Ray was pulling some sort of prank.
Ray did enjoy the moment Paul took off to buy beer for the guys. He even enjoyed making a big list of chores he needed done: dishes, laundry, bed sheets, vacuuming, mopping, dusting, toilet cleaning, and so on. And for the first couple of days it was fun, bossing him around, watching him drag his feet through the house as he completed one tedious task at a time. But the novelty quickly wore off, and it wasn’t long before Ray started to worry that he was just making Paul angrier and more determined to win the next week so he could boss Ray around twice as badly.
It was Wednesday when Cass sent another message. “Everything okay?” she asked simply. Ray ignored the message, though it wasn’t easy to do so. There had been a few times that he’d thought about reaching out to her. And there were a few times he thought that maybe he could get over her downstairs mix-up. Maybe he could be with a girl like her, despite her cock. She was beautiful and soft and warm and they had everything in common. But sooner or later, his friends and family would learn her secret—it was inevitable. Secrets that big don’t stay secrets forever. And what would his family think about the fact he was involved with a biological male? What would Mason think? Mason would probably die of laughter. Maybe it was just better to leave that message unread. Maybe it was just best to leave Cass alone.
So he didn’t answer the message. And Cass got the message loud and clear. She didn’t send another message. Ray got exactly what he wanted: a tick in the Fuckeries win column, and Cass off of his back.
Though the satisfaction was short-lived. Sunday came up quickly, and Ray had nothing for the awards ceremony. He found himself marching right back across that street to that liquor store, ready to spend another forty bucks on beer he wouldn’t even get to drink. “Lose again?” the store clerk asked.
Ray didn’t answer. He went straight to the wall of beer and he got what he needed.
“Was it at least close?” the store clerk asked. “It wasn’t you last week—so things must be looking up, right? Did you watch that video I told you to watch?” And Ray continued to ignore the man. He paid the bill and then he hauled the beer over to the house. And now he was ready to start his chores.
And when he went to bed that night, that empty feeling was still teasing away at him. He missed the warm comfort of Cass’s body. He missed the sex too—but he wasn’t proud of that fact. He kept telling himself that the sex would have been better if Cass was actually a girl. It probably felt better in the pussy—though Ray could only speculate; his only experience was inside of Cass’s butthole.
CHAPTER VIII
After two straight days of swiping on Tinder, Ray found a match. She was cute enough, with freckles and bangs cut into her brunette hair. She was a big fan of music, though she seemed to like country more than the kind of music Ray preferred. Still, Ray set up a time and place to meet up, and she agreed—so Ray had one point on the board for the week.
He went to the bathroom to shave up before his date, but Mason was already in the bathroom, having a long, steamy shower. “Mind if I shave while you do that?” Ray asked.
“Why? Do you have a date or something?” Mason asked with a snicker.
“Actually yeah, I do—a hot date, as a matter of fact.”
He laughed again. “Well that makes two of us. I’m seeing this blonde chick and I’m pretty sure she’s looking for a good fucking. Don’t worry, I already jerked off before you came in here.” And then he snickered one more time.
“That’s nice,” Ray said, not fully paying attention. He knew that Mason would try to get him off of his game. But he was determined to stay in a good headspace, so that he could potentially win another week of Fuckeries.
“Yeah, man. You should see this girl. You would die—way out of your league. Hell, she might even be out of my league, but I don’t think she knows that. I called her this morning and she got all flustered. God, shy girls are just too easy. Do you want to know the trick with shy girls?”
Ray quickly finished shavi
ng and then he got out of the bathroom before Mason could go on with his silly rant. But Mason chased him down in the hallway, wrapping a towel around his dripping wet body. “Hey man, what gives? Now that you’ve won a week, we finally have something in common. Don’t you want to tell me more about your girl?”
Ray turned around and forced a smile. He hated hearing that he had something in common with Mason, the king of the douchebags. “I’m okay. I’m just going to see where it goes,” he said, straining to keep that smile on his face.
“Well, at least let me show you this girl. I feel like she would be your type. She’s blonde, just like that girl you fucked in the ass last week.” He grabbed his phone and then flipped it around. Ray’s heart stopped momentarily. He was looking at a picture of Cass. Mason was going on a date with Cass. “We matched on Tinder. I think she might be a bit tough to crack, but I’ll get to her.” He licked his lips, making Ray feel even more uncomfortable.
At least Ray wasn’t the only one who thought she was a beautiful woman. Though if Mason actually got close to sleeping with her, he would discover her secret, and then he would mock Ray endlessly.
But what if Mason went through with it? What if he slept with her? What if he filmed her while she wasn’t looking and then humiliated her later by showing the footage to Ray and the other guys? Ray couldn’t let that happen to her. She was too sweet for that kind of punishment. Or could he let it happen to her? He didn’t own her. He hadn’t even talked to her since she left the house. He wanted to cut off contact, so he couldn’t be upset with what happened to her now…
“Good for you,” Ray said, forcing another smile. “I’m going to be late, so I need to get going.”
Mason went into his room, looking at Cass’s picture while snickering and probably imagining himself fucking her in the pussy she didn’t even have. And Cass was all Ray could think about as he made his way down to the pier where he planned on meeting his freckled brunette date. He arrived an hour early, but instead of feeling nervous, he felt worried, still thinking about Cass, unable to even muster up the mental image of the girl he was due to meet.
Big Hard Girls Page 49