Kasey and Jack's Big Adventure

It had been three weeks since Jack and Kasey had met at a truck stop. Despite the manager's warning that "This kind's always trouble," Kasey seems to have been the answer to his prayers. A recent high school graduate, and half his age, Kasey was eager to escape a home life that included a mother that didn't too much care for her, and her mother's boyfriend who maybe did.

Once she and Jack hooked up, she ditched the baggy camouflage clothing she wore for safety and embraced the inner slut she always wanted to be. Now she dressed in a manner that showed off her assets either directly via short, cropped t-shirts, low cut blouses that let it all hang out if she bent over, or tank tops with large side openings that gave a clear view of everything that she had if the angle was right. She always made sure that at least half of her ass cheeks were hanging out the back of her shorts. Sometimes she'd just wear panties as outerwear.

Kasey wasn't just a slut on the outside, though. Jack found that what she lacked in experience, she more than made up for with imagination, enthusiasm, and a knack for looking up kinky stuff on the Internet. Hell, the first day he'd met her, she ended up getting them involved with a couple of cute bisexual waitresses they met when they dined at a steakhouse.

Kasey seemed to have no inhibitions where sex was concerned. She found out that Jack was into urolagnia and promptly pissed all over him right on the street, a block from their motel room. Since then, she'd pissed all over him, in his face, but mostly, in his mouth. She didn't judge. She'd even tried it herself. Piss, that is. It wasn't her cup of tea, pun intended, but she'd do it if Jack wanted her to.

She also found that she was attracted to women. She and Jack would discuss the things about women that turned them on. They both found asses extremely attractive. She was glad that Jack liked hers because she didn't have a whole lot in the tit department. But Jack said he liked her perky tits, small as they were. Kasey liked pussy, though, as much or maybe more than Jack if that was possible. She and Jack had discussed this at length and had agreed that anything they did while the other person was present was not cheating--the assumption being that they were both in agreement and that even the one not directly acting was still participating by watching.

Jack often benefitted from this arrangement when Kasey would find a girl willing to submit to cunnilingus as long as Jack could watch. What worried Jack, however, was that one day this arrangement would lead to Kasey getting drilled by some guy hung like a horse while he looked on helplessly. He knew that some guys were into that. He didn't think he was one of them, but he also knew that he wouldn't be able to tell Kasey 'No' if that's what she really wanted.

Jack hadn't really ever envisioned a scenario where that would take place. Kasey had said, again and again, that she was his girl, that she loved him and wanted to have all his babies. So far, they hadn't had any babies, nor any opportunities for Kasey to get boffed by some strange cock. But that was potentially about to change.

Jack had some time off coming and Kasey suggested that they spend it in Las Vegas. While enroute, Kasey had found a strip joint that featured transexuals. Jack had hinted that he might find such an experience to be "interesting." Kasey though so, too. So, after parking his rig at the casino where they were staying, he and Kasey hopped in a cab that took them to the club. It was a short drive outside the city and looked like a typical strip club dive from the outside. It looked like a dive on the inside, too, Jack thought. Despite his apprehension, he followed Kasey as she pulled him toward a table.

"Hi folks," their waitress said in a voice deeper than it should have been given her appearance. "Would you like something to drink? We have a special on Gin & Tonics. Only $4."

"Sure," Jack said. "That sounds great."

"I'll need to see some ID," she said.

Jack pulled his out, but Kasey admitted to being under 21.

"Sorry, sweetie," the waitress said to her. "I'll bring you a soft drink on the house. What would you like?"

"Coke is fine," Kasey answered. She hadn't really expected to be served. She wasn't big into alcohol anyhow. It wasn't the sort of thing that would ruin her evening. "My friend and I are looking to hook up with a couple of willing girls tonight. He's never dated a transexual before."

"First timers, eh" the waitress said smiling. "Well, I hope you guys have a good time. We've got a lot of girls working tonight. Maybe one or two will strike your fancy."

"Are you seriously planning on picking up a couple of these girls?" Jack asked with a bit of disbelief.

"Maybe," Kasey shrugged. "Maybe you just relax and take a walk on the wild side for once."

Jack watched the strippers in fascination. Granted the lighting was low and forgiving, but he was amazed at just how much these girls looked like real girls. The biggest tipoff that the stuff under the hood was not standard issue wasn't in their appearance, Jack realized, it was in their movements. He couldn't put his finger on just what it was, exactly, but they moved like men. He wasn't sure he could get over that. He had found some shemales, as he called them, attractive when he'd run across them in magazines or on the Internet, but those photo spreads were still images.

"I'm Jenny," said a diminutive girl who suddenly appeared beside him. "Mind if I join you?"

"Not at all," Jack said. "I'm Jack and this is my girlfriend, Kasey."

"Pleased to meet you both," Jenny said, while giving Kasey the once-over. She slid into the curved booth next to Jack. "I'll get right to the point. Alexis told me that you two were interested in getting better acquainted with some girls. We have a VIP room that might meet your needs. For only $100 you get the meet all the girls on staff, check 'em out, see if you hit it off, that sort of thing, for thirty minutes. In that time, you can do whatever you like to whomever you like as long as it's mutually agreeable. I'm not gonna lie, there's a suggested tipping amount for mutually agreeable things beyond talking. But, if you find someone that you really like, you can make arrangements to meet that person in private and develop a relationship."

"If you're interested, just see that gentleman over there by the sign." She stood up to leave. "By the way, do you know what sort of qualities you're looking for in a woman? Big tits? Big dick? I can make some recommendations."

"Big dick," Kasey blurted out. "For one of them, at least." Jack shot her a look but said nothing.

"Pretty face. Feminine. Nice ass. Small tits. I'm not as concerned about the size of her dick, but big isn't a bad thing."

"Melody sounds just like your type," Jenny said to Jack. "I've always been a bit jealous of her ass, and her equipment is pretty nice, too." Shifting her attention to Kasey, she said, "Shania's probably the one you're looking for. She's got the biggest wanker I've ever seen and her tits are all natural--as natural as they come on us, anyway" she said with a wink.

Jenny leaned over conspiratorially, "If you want to tip me $20, you can save the $100 for the VIP room and I'll send them both to your table."

"That'd be great," Jack said, pulling a twenty out of his pocket and handing it to her. He really didn't want to have to speed date in the VIP room. There was a risk she wouldn't come through on the deal, he'd been stiffed in strip clubs before, but Jenny seemed on the level. She wasn't even bad looking, he thought, but still looked too masculine for his tastes.

"Big dick?" he asked Kasey when Jenny had gone.

"For both of us," she said. "This may be our only chance to experience this. I'm just looking out for you," Kasey said with an impish smile.

Jack was beginning to have second thoughts about this. He wasn't gay. He really loved women. Yet ever since the first time he'd seen pictures of shemales, he'd been fascinated by them. Some were better looking than most women. And yet, they had that something extra in the form of a penis, that added an extra dimension to their allure.

He and Kasey watched the girl dancing on stage. She had large, perfect tits on a frame that was still somewhat masculine, and a bigger booty than he preferred, but she was stroking a semi-hard penis that was larger than average. He hoped she wasn't the one Jenny intended to hook them up with. To Jack, she just looked like a man with a boob job wearing makeup. He had hoped for better.

"Good evening, folks," said a voice belonging to a girl about 5'7" with curves in the right places and a dark, should-length, wavy bob. The voice was sultry and not too deep. "I'm Melody. Jenny said you were looking for some company."

Jack looked her up and down. She was actually pretty, he thought. She didn't have big tits, but she didn't appear to be flat chested either. In fact, he mused, she might even have bigger tits than Kasey. He stood up and offered to let her scoot in.

"I'm going to be up on stage in a few minutes," she said, "so you'll have to let me out in a bit." She looked at Kasey. "You're pretty," she told her.

"I'm Kasey," she said, "and you've met Jack."

"Well, it's a pleasure to meet both of you. Have you ever walked on the wild side before?" Jack and Kasey shook their heads. "Great!" she said. "I enjoy first-timers. I assume you'll both be participating. I know Shania will be stopping by in a moment."

"Yes," Kasey said. "This is mostly Jack's thing. I'm just along for the ride, filling in where necessary."

"Or maybe getting filled?" Melody winked.

"Maybe," Kasey grinned sheepishly.

"So, what's your thing, Jack? How can I fulfill you fantasy?"

"I really like the rear view," Jack said. He had never really verbalized this fantasy before, so it was difficult for him to say, "I want to suck your cock and then have you fuck me in the ass."

"That's pretty basic," Melody said.

"He left out the part about wanting you to hose him down with your piss," Kasey added mischievously.

"Ah! The truth comes out!" Melody laughed. "That sounds exciting to me. I'm looking forward to it. I saw you checking out my ass, Jack. Does it meet your approval?"

"Seems to," he answered.

"Is it good enough to eat?" Melody asked. "Because I just love getting my ass licked."

Jack gulped. His fantasy was transitioning into reality and suddenly getting scary. "I guess I'll find out."

"Sorry I'm late to the party," said a tall girl standing next to Kasey who introduced herself as Shania. "I can already see that I'm going to like you two."

"You will, Shania! They're first-timers and Jack wants to eat ass, suck cock and get pissed on," Melody said, filling her in.

"Wow! What about you, sweet thing?" she asked Kasey. "I heard you're looking for some serious cock." Jack had never seen Kasey blush before, but it was evident even in the dim light of the club that she had. "I will be happy to take care of that for you."

"Just so you know," Shania added, "we're all going on a date. We do not engage in prostitution, so don't offer to pay us. Melody and I have one more dance. Our shift is over at eight. We will go with you to your room and enjoy some great sex together. We do this because we are horny sluts who just can't get enough."

Shania and Melody both left to finish their shift. Melody danced next and Jack found that she was quite attractive. She had perky natural tits that were a bit larger than Kasey's, a slim, shapely waist, and a sweet ass that he couldn't wait to put his tongue into--and then, of course, his cock.

"Holy shit!" Kasey exclaimed during Shania's dance when she stroked herself to at least 10" of thick meaty erection. "That is one big cock!"

"Don't get too excited," Jack said. "You might give me an inferiority complex."

"Oh, baby, you know I'll always love you and your cock. You've got nothing to be ashamed of. It's just that... damn!" Jack was only slightly consoled. Secretly, he wondered what it must be like to have something that huge shoved up your ass and shuddered.

The girls arrived at their table when their shift had ended, dressed in normal street clothes. When they got back out into the daylight, it was only just after eight, Jack was pleased to see that the light didn't hurt Melody's appearance at all. She was still pretty, and her ass looked great in the designer jeans she was wearing. Kasey took Shania's hand as they walked to the cab. Jack followed suit by putting his arm around Melody. After they got into the cab, Kasey started fondling Shania's member, which, predictably, started to grow.

"Easy, girl," Shania said. "I don't want to have to get out of this cab with this. At least let me get to your room before this happens."

"Are you nervous, or are you always this quiet?" Melody asked Jack.

"Nervous," he acknowledged. "I can't believe I'm doing this." It struck him then, that what he said could be construed in a negative light. "You're very pretty," he said. "I'm looking forward to doing it with you."

"That's sweet, baby," Melody said. "Thank you for saying that."

They went up to the room and Shania took charge.

"Here's what we're gonna do. Everybody has to get naked. Then we're all going to do a wagon train. We all get down on all fours, stick our noses up the ass in front of us and lick. After a few, we'll switch until everyone gets to taste everyone else's ass. No cock sucking or pussy licking allowed at this stage.

Kasey had never been much into asslicking. Not like Jack, who loved licking her ass for hours. Still, she played along, knowing that, at some point, she would experience Shania's huge dick filling her like she'd never been before.

Jack loved licking ass. He loved licking Kasey's ass. He enjoyed Shania's ass, though it wasn't as prime as Melody's. Melody had a wonderful ass. The kind he'd always imagined a shemale might have. He drove his tongue as far down as he could get it. He got hard licking Melody's asshole.

Melody had misgivings. Jack was a newbie. He could have turned out to be a complete downer. All those misgivings disappeared when she felt his tongue pressing into her anus. The boy could toss some salad.

Shania was used to folks being in awe of her huge cock. She knew that 11" penis with a 6 1/2" circumference was well above average and stood in the way of her being the woman she so longed to be. Still, she loved the men who loved her cock. It wasn't ideal, but it was good enough. Probably as good as she would ever get. She didn't as often run across a woman who was as enamored with her cock as Kasey was, probably just do to the circles she moved in. And because women who saw her as a woman wouldn't be interested in her anyway--unless they were lesbians. Then they'd be disappointed that she had a cock. Even though she was looking forward to sex with Jack, she would be happy to ram her giant cock up Kasey's willing wet pussy.

"Okay, listen up, peeps," Shania said once everyone had licked everyone else's asses. It's time for us to give special attention to the one's we're here for. Jack and Melody need to spend some quality time together. And Kasey and I need to become better acquainted. In a little while, we'll regroup and see what else needs to be done."

Kasey didn't mind that Shania's tits were bigger than hers. She didn't even care that they were fake. Kasey, liked women, after all. Shania's biggest attraction for her was that enormous cock. She wasted no time wrapping her lips around it.

Shania had had her share of blowjobs. But Kasey's talent blew her away. (No pun intended.) Kasey seemed to know exactly what to do to derive the maximum penile pleasure--rare for a girl with no penis, Shania thought. Kasey's small tits were cute, the way a lot of her friends who were trans were cute. All-in-all, Shania got as hard as she'd ever been.

"Baby, if you want this inside you, now's the time."

Kasey had waited for this moment since she'd heard they were going to Vegas. She gasped as Shania slipped the head of her huge cock into the entrance of her vagina. She tried to relax. She was determined to take it all. Shania, very gently, pressed a little more cock into her, waiting at each step of the way for Kasey to acclimatize to its massive girth. Soon, Shania had gotten her cock all the way in and Kasey begged for it all. Shania gave it to her. All eleven inches.

Jack was a natural cocksucker. He loved the sight of Melody's luscious ass and sucking her cock from back there made his cock as hard as a rock. He kept doing to her what he thought would be good if someone did it to him. It wasn't long until Melody shot a load of hot white cum into his mouth. Jack swallowed without hesitation. He pulled his mouth off Melody's cock and looked up to see Shania driving her eleven-inch dick balls deep into Kasey's cunt. He watched in fascination as Shania emptied her balls deep into Kasey's pussy, moaning as she did. It only made him want to fuck Melody all the more. He drove his stiff cock into Melody's already lubed up ass and she moaned in response. Jack didn't hold back. He hammered his cock into her ass as hard as he could.

Melody loved every minute of it. Not only could this guy suck cock but could deliver it up her ass as good as anyone. It was a shame Jack was already taken, she thought. The good ones always are. She would have liked to make a play for him otherwise.

Jack came hard. It was an orgasm that went deep into his core. It released not only sperm, but all the pent-up anxiety he had been feeling. He wondered why it didn't bother him more that Shania just emptied cum into his girlfriend. He didn't have time to think about it, because Shania was waving her softening cock in front of his face telling him to lick his girlfriend's pussy juice off it.

He did. It was as though he could do nothing else. Shania's cock was huge. It was one thing to say, even to see, but something else when it was in your mouth. He let his tongue travel around its head, tasting the sex on it. Kasey's sex. Shania's cum. Jack didn't understand how it could be that Shania could cum in Kasey and still be hard and grow even harder as he used his mouth to pleasure her cock.

He couldn't think while Melody was lubing up his asshole with three fingers. When she put her sizeable cock in his ass, he lost his mind. It didn't hurt. Melody knew what she was doing. She'd gotten him ready before she plunged her cock in his ass. It felt... different. Like he was filling up and emptying at the same time. With a cock in his mouth and another in his ass he felt... used. Just as he realized this, Shania came in his mouth. Not just a little. The girl was not only hung like a horse, but also came like one. Jack couldn't even keep it all contained in his mouth. He had cum dripping down his chin like a broken-down ghetto whore.

Melody really liked Jack's ass. It was tight and he was a good-looking guy. She didn't want to cum in his ass, though. She wanted to watch him swallow her jizz. She saw that Shania had just finished, so she picked this moment to pull her cock out of Jack's ass and press it to his lips.

What the hell, Jack thought, but he suppressed his exasperation because he genuinely liked Melody and the cock that went with her. Dutifully, he took it in his mouth--never mind that it had just come out of his own ass. He let his tongue caress the head of her penis.

Melody was already close to coming, and when she saw the expression of submission wash over Jack's face it pushed her over the edge. She had been saving this load up all day and Jack got all of it.

"I got to pee, Shania said. Who wants it?" She expected Jack to answer and was surprised when Kasey said, "I do."

Jack was too overwhelmed to object. He might normally have been the one to answer the question but had just swallowed two loads of cum--something he never thought he'd ever do. So he just watched as Shania positioned her still-imposing-when-soft cock over Kasey's waiting open mouth. Apparently, anything Shania did, she did big, because she must've pissed a gallon. Jack watched Kasey's throat as she swallowed gulp after gulp of hot yellow piss straight out of Shania's penis. He didn't realize that Kasey liked drinking piss as much as he did. She'd done it for him once or twice, but seemingly out of obligation, not because she genuinely liked it. Maybe she just didn't like his piss.