Dress up can be fun.. and profitable?

Story by steampunkstallion on SoFurry

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Two guys go out, get a bit drunk and fail to pick up girls. They get back to the one guys place, and his friend finds some stuff his girlfriend left there and bribes him to dress up.


Alex: wolf Chris: tiger

Alexander laughed quietly, sitting at the bar with a good friend of his. Slowly, he glanced around the bar, noticing all the girls who wouldn't give his friend Chris, or himself the time of day. Both of the guys had tried speaking with a few of the girls, but none of them seemed terribly interested in them. Sighing, as they finished their beers, Alex glanced over at Chris.

"Damn. I doubt we're going to any tail from these women tonight... Well tail for you anyhow. My girlfriend hates when I play wingman for you." Pausing, the wolf glanced around the bar, noticing the proportions of guys to girls here. It was a very large female population, and besides Chris and himself, there were only two other guys in the bar. They made their way outside, hailing a cab. Once inside, Alex gave the driver directions to his apartment.

Getting back to his apartment, they went in and Chris slumped on the couch. "Want a beer?" Alex spoke up from the kitchen, tail wagging slightly behind him. Noticing the tiger nod, he grabbed one and sat down beside the Chris, and listened to him whine.

"Damn cold bitches." He laughed, watching the tiger reach down and adjusted the bulge in his pants. Alex blushed brightly, folding his ears back to hide the embarrassment, giving a little lick of his muzzle. Glancing at his cell phone, he paused for a moment and started to laugh. Chris glanced at him a bit funny.

"We went to a lesbian bar. That's why they didn't show any sort of interest in us." Showing him the reviews of the Beautiful Beagle. All the reviews that showed it was a lesbian bar for women to pick up other women. "Dude, didn't you bother to check out the bar before we wasted the time there?" The two of them looked at each for a moment, and then started to laugh.

The lounged around for a while, drinking several more beers each. Alex settled back, and had fun playing video games. Glancing at the table, he guessed that they each had four or five beers at this point. Lifting his head, he noticed the clock said it was just after two in the morning. Alex occasionally glanced over at Chris, noticing that the lump in his shorts still hadn't gone down at all. Chris paused the game, pointing over at a box on the floor.

"Hey, What's that stuff Alex?" Alex blushed brightly, not wanting to tell the tiger it was the stuff his girlfriend left. He watched Chris get up and head over to the box, lifting stuff out of it. He felt rather embarrassed.

"It's just some stuff my girlfriend left here. It's some clothes she leaves if she needs to get changed or items for spending the night." Watching as Chris lifted up a pair of light purple pair of panties. It's what the tiger said next that made the wolf blush almost visibly through his gray fur on the couch.

"Hmm. I bet that you could fit into some of this stuff she left. I'm curious if you'd actually try it on for me." Squirming in his seat, he could see the tiger's grin. Alex smirked slightly and replied.

"C'mon man, I'm not going to try on any of my girlfriend's stuff, she'd beat my ass." Sticking his tongue out, glancing over at what the tiger was holding up. He was a little curious if some of the stuff would actually fit. Thinking back to when his girlfriend has visited, she fit his clothes pretty well, so they were probably pretty close to being the same size.

"Hey, I won't tell anyone man. You can trust me." Watching Chris tug his phone out of his pocket, padding over and set it in his coat pocket. "There. Now I can't take any pictures, and no one would believe me if I told them without pictures." His long tail swayed as he made his way back to the box. He could tell that Chris noticed the blush in his ears as he spoke. "I'm just kind of curious, that's all."

Alex grinned widely, figuring his friend wasn't going to take his agreement for the cross dressing. "If I do it... You need to buy me a new iPod. Mine's getting old, not the cheap one either." His tail thumped against the couch. "I'd want one of the high end ones... with tons of memory." Knowing that his friend wasn't that dumb to agree to it, His tail wagged a bit faster now figuring he had won this contest.

He could see Chris thinking it over, and then he nodded slowly. "Sure. I've got a bunch of extra money lying around from my inheritance and it's burning a hole in my pocket." That grin faded nearly instantly from Alex's muzzle, his friend just called his bluff. Shrugging slowly, at least he was going to get a brand new mp3 player out of doing this. Standing up, he made his way over to the box, his foot paws in the soft carpet under him.

"Here we go." Alex took the stuff that Chris was handing to him, making him blush. "Now get changed... right here. No one is going to see you but me anyhow." Watching the tiger flop back on the couch after speaking. Alex nodded, reaching up he unbuttoned his shirt, taking his time. Sliding a paw down, he undid his shorts next, letting them fall down to the floor. Stepping out of them, he hooked his foot paw into it and tossed it over near the table. He was now standing there in his boxers, feeling quite nervous. Alex was grateful that he had more than just a few beers in him at this point.

"Are you sure man? I mean, that's expensive... like five hundred bucks." Blushing, Alex watched as Chris nodded slowly, a paw resting on his crotch at the moment.

"Oh I know. If I'm going to embarrass you, you might as well take advantage of it right?" The words seemed to make a bit of sense to his alcohol fueled brain. Nodding slowly, Alex bent over and pushed his boxers to the floor and stepped out of them as well. Turning around, still bent over, his tail flicking behind him as he picked up the panties. His ears perked slightly, he could have sworn he head Chris mutter something about a good view. The wolf knew the view the tiger was getting was a gray rump, a fluffy tail and his heavy balls hanging between his legs. Glancing back at Chris, the tiger waving his other paw gestured to continue.

"Fine. Fine." Stepping into the panties, he drew them up his legs. Alex gave a slight shiver, feeling the soft material covering his groin. Using his paw, he adjusting it and tucking his heavy balls into the front of the panties. Reaching back adjusted the back of the panties so they covered his rump fully. Admitting silently, it did feel kind of nice with the fabric hugging his body, making his sheath and balls stick out rather lewdly. Giving a little spin, he smirked. "Ta Da. Done." Glancing at Chris, a bit of smirk on the wolf's muzzle.

"Nope. All of It. Skirt, shirt and everything..." Alex's ears drooped and nodded slowly. He knew it couldn't be that easy, glancing at the other items on top of the box. Picking up the black mini skirt, he wrapped it around his waist and clipped the buttons on it. Alex glanced at the full length mirror on the wall, and the wolf couldn't help but blush. The skirt did an almost perfect job of hiding the bulge between his legs. If he hadn't known any better, there is a good chance he could be confused for a flat chested wolf girl.

Alex dug in the box a little, trying to find something to cover his upper body with, and noticing the French maid outfit he bit his lip. Stuffing that to the bottom of the box, he made sure to cover it with other items. He pulled out a thin strip of stretchy material, spandex or something similar. If he remembered right, it was his girlfriend's sports bra. He slid it down over his chest, and fixed it so it sat properly. The wolf squirmed, his nipples poking out against the material rather noticeably.

"Damn... that's not too bad looking actually."Alex watched as his friend Chris was now stroking the bulge in his shorts slowly. "Come on. I know I saw a pair of heels in that box, and we both know you and your girlfriend have the same size paws. She teased you about it the last time she was here." Alex shook his head slightly.

"Oh come on man, I don't want to wear some silly high heels... damn." Listening to Chris grunt slightly, the tiger was squeezing the bulge in his pants, the action making Alex blush. The wolf watched his friend close his eyes, panting softly for a minute before he spoke up.

"If you wear the heels too... I'll get you those nice Bluetooth headphones you've been wanting for a while. You can use them for both the mp3 player and your phone." Alex watched the tiger's tail thump against the couch; he weighed his options a bit. Sighing, it would allow him to save a bunch of money.

"Fine." Picking up a pair of black heels, he stepped into them carefully. It felt really odd, the backs of his paws lifted up, causing him to balance himself, chest sticking out slightly. Shaking his head, he didn't understand how girls could do anything wearing these. "Is this better?" Glancing at Chris, Alex watched him get up and approach him.

The tiger growled and Alex blushed. "Now that's what I'm talking about... you could pass for a girl pretty damn easily." Blushing, he bit back a giggle when his friend licked his nose. "Maybe brush that hair out a bit... or maybe even let it grow out." Alex panted softly, blushing as Chris' paw rested on his belly. "Though..." That paw slid slowly down, cupping the bulge in Alex's skirt. "This would be a dead giveaway you weren't a girl." Alex gave a soft moan, squirming.

"C... Chris what are you doing? I've got a girlfriend." He didn't make any real effort to remove the paw from his crotch. "A... and I'm sure your girlfriend will come back." Blushing, Alex admitted it did feel kind of nice, both his girlfriend and him had been busy with finals for the last few weeks lately. Due to that, neither of them had much time for each other, and he didn't enjoy masturbating too often. He moaned softly, feeling Chris' paw stroking him slowly, making him lean into it slightly. "I... I'm not gay Chris."

"Neither am I, I'm just teasing a cute girl I met at a club." Alex whimpered softly as the tiger squeezed his bulge firmly, making him stand up a bit taller in the heels. Closing his eyes, he whimpered and gripped Chris' shoulders, fingers gripping tightly. The tiger was doing a really good job at getting him aroused. That paw slid under the skirt, and Alex didn't say anything, feeling this fingers caressing and coaxing his sheath under the panties now, making him whimper. Ears perking up, listening as Chris teased him. "Mmm seems a bitch wolf pussy is all swollen... maybe I should eat you out."

Alex groaned, shaking his head as he thought to himself. "There is no way Chris is going to do what I think he's going to do." He felt the skirt lifted, and his paws left Chris' shoulders as he felt him moving down. Giving a soft moan, he felt Chris' breath blowing over the thin material, realizing that the tiger was actually kneeling in front of him! A rough feeling made him glance down, the tiger's head under the skirt now, and he could tell Chris was licking his sheath through the panties. Moaning very quietly, he stroked his paws over his friend's head, closing his eyes once more.

"Oh fuck, that feels really good actually." When Alex felt Chris' paws trying to tug the panties down, he blushed and whispered. "L... Leave them on." Squirming, he stood there, dressed like a girl as his friend lapped at him through a pair of panties. It had been nearly a month of no sex for the wolf, and no release either as his girlfriend and he hadn't had much alone time lately. Groaning, he allowed Chris to keep licking and teasing his sheath and balls through the material. His cock tip peeked free, staining the panties a little with precum as the licking suddenly stopped. "Y... you stopped?" Whimpering, Alex slowly opened his eyes.

Chris was standing up, grinning widely at him. "Yep. Come on... let's sit on the couch and watch a bit of TV." Nodding slowly, he blushed and followed the tiger over to the couch. He was fairly unsteady on the heels, but found out if he swung his hips slightly side to side, it made walking a bit easier. Settling down on the couch, he cuddled up against Chris gently. The tiger's arm slid around the wolf drawing him close. "See... That's a good girl. Cuddle up with a big male." Alex nodded, blushing as his paw rested on Chris' stomach. His eyes were drawn that bulge, the shorts hugging it tightly. Blinking, he was a bit confused when Chris turned off the lights and picked one of the movie channels to watch.

They were settled in and watching the movie, at least one of them was. Alex was blushing and couldn't believe that he was here, on the couch dressed like a girl and cuddled up against his best friend. "Wonder what would Jenna say?" Alex thought to himself, betting his girlfriend would think it was funny. The wolf's eyes ignored the movie, glancing at the lewd bulge in the tiger's shorts, and he could smell his arousal quite easily this close. Alex wondered slightly what it'd feel like to touch it, if it'd feel any different than touching himself. Sliding his paw down, his fingers brushed over the bulge very gently, almost delicately. His ears perked when Chris started to purr a bit deeper, and that paw that rested on his shoulder gave him a squeeze. Feeling a little encouraged, the wolf had always been a bit curious what it'd be like to play with another guy. He knew that he'd never admit it to anyone, but if anything happened, he could blame the beer.

Gently, he wrapped his fingers around the bulge and began to stroke it slowly. "Oh that feels really good babe. Keep it up..." Blushing, Alex nodded slowly and ignored his own swollen sheath, toying with his friend's bulge. It felt quite warm, and that sheath twitched under the material. He could tell by the way it felt, that his friend wasn't wearing any sort of underwear. That bulge was growing, thicker and longer feeling, causing the wolf to blush. Alex had to admit, Chris felt really big and thick. Closing his eyes, he nuzzled into Chris' chest, breathing in his scent, the tiger did smell kind of good if not a little musky. Alex kept his ears perked, listening to his friend's growing purr, and that breathing as it got heavier. His paw was now roaming up and down the entire length of that bulge, and he heard Chris growl out softly. "Now be a good girl... unbutton my shorts, help your boyfriend out."

Shivering, Alex nodded and slowly undid the buttons on the tiger's shorts, tugging them open. Alex glanced down and his eyes went wide. Chris loved to brag about being a bit on the large size, and it seemed that bragging was justified. Suddenly Alex felt really small, his friend's sheath easily topped out at six or seven inches long and almost as thick as soda can. Biting his lip, he reached down and wrapped his fingers around that sheath, a bit of black tiger flesh oozing free. He was suddenly glad that his girlfriend had never seen Chris naked, wondering what she'd think of a male whose sheath was almost as big as her boyfriend's cock. His fingers wrapped around that furry tube, sliding it up and down gently over the emerging shaft, before sliding down and cupping the tiger's balls. They weren't very dangly, but they were very heavy feeling and easily the size of a pair of jumbo eggs. Teasingly, Alex spoke in the best imitation of a girl's voice he could do. "Awww. Seems like a kitty is all pent up."

Alex's ears folded back, Chris growling out slightly. "Don't tease a tiger, trust me, It'd be very easy to bend you over that table in front of us and fuck you. So be a good girl, stroke my cock till I cum and then tomorrow we can get your silly little toys." Nodding slowly, Alex kept his ears folded back a bit submissively, not wanting to upset his drunk horny friend. His fingers gently stroked that sheath, giving it light squeezes as he listened to Chris whimper slightly. After a moment, he pushed that sheath back, exposing his friend's aroused length fully. Shivering slightly, he watched as it kept growing, his paw was wrapped around it and he could get his middle finger and thumb around that thick flesh. Alex had always thought that felines tended to be on the small side, but this was definite proof that not all of them were. His tail started to wag a little when Chris praised him. "Mmm that's better. Such a good wolf bitch."

Giving a very soft giggle, Alex's paw slowly slid up and down that shaft, coaxing soft moans from his friend's muzzle. He used the same technique that he used on himself, the rare times that he did masturbate. Squeezing the base, he lightened his grip as his paw slid upwards to just under the head of the cock. A rather copious amount of precum dripped from the head of the cock and onto Chris' shirt, but the tiger didn't seem to care much about that. Giving it a soft squeeze, he gauged his friend to be easily ten or eleven inches of big thick tiger cock. Glancing up, Alex noticed that Chris was staring at the ceiling and panting heavily. Reaching over with a free paw, he tapped the remote and plunged him and his friend into almost total darkness. There was a little bit of light from outside streaming through the blinds. When Chris didn't react, Alex smiled and started to stroke his friend's cock a bit faster.

"Mmm fuck, come on Jenna... suck my cock." Alex's ears perked up, for some reason Chris was moaning his girlfriend's name. Alex gave Chris' cock a firm squeeze and whispered.

"Oh I couldn't do that... I'm Alex's girlfriend." Alex kept stroking the shaft, caressing it slowly as he felt that paw slide from his shoulder to stroke the back of his head. It was softly and slowly pushing him towards the tiger's cock. The wolf blew softly against his friend's shaft, watching as those barbs stiffened on the shaft.

"Just a little lick wouldn't hurt... just give it a kiss sunnflower." Alex blushed, ears perking up as that name left his friend's muzzle. That was Jenna's secret nickname for him; he was a bit lost as to how Chris would know that. He was lost in his thoughts and confusion; he didn't realize exactly how close Chris had gotten his muzzle to that cock. Alex felt it brush against his lips, and not thinking he parted his muzzle slightly. "Mmm that's it..." Folding his ears back, the tiger's paw gently pushing his muzzle a few inches down on to the maleness. "Now take more of it into that sweet little muzzle..." Not wanting to upset his friend, and figuring this was going to be a onetime occurrence, Alex closed his eyes and started to bob his muzzle. He had good six or so inches in his muzzle, his paw stroking the rest of that thick flesh. It didn't taste as bad as he thought it would, the wolf's broad tongue curling around that cockhead, coaxing more precum to drool.

Bobbing his muzzle, Alex listened to the moans coming from his friend as he sucked on his cock. It felt terribly dirty doing this, in the dark of his apartment, cross dressing in his girlfriend's clothes, and a big tiger cock filling his muzzle. Alex gagged slightly; Chris bucked his hips slightly stroking his head fur. "Fuck... doing such a good job, going to reward you girl." Alex tried to pull his muzzle up, realizing what his friend meant, the words coming a moment later. "Going to cum... better get ready to swallow." Chris' paw held his head firmly in place, hearing a loud growl that flesh in his muzzle started to pulse against his tongue. A moment later, his muzzle was flooded with thick cum. Alex swallowed all of it, shuddering slightly at a combination of the taste, and the scent. There was the thick smell of male, heady and intoxicating, and the taste was potent if not a little bitter. Alex was thankful it was only a muzzle full, and not the huge amount he produced normally himself. After the flow ebbed off, he kept licking that cock in his muzzle, Chris' paw tugging his head off as he snarled. "Fuck. Stop that's too much..."

Alex pulled up and looked over at Chris, his fingers gently wrapped around the cock stroking it. "I'm curious... how did you know Jenna's nickname for me?" he watched the tiger's ears blush in the pale lightly.

"Well last time you two came over to my place and were drunk... you remember that night?" Nodding slowly, Alex blushed himself remembering how Jenna and he had fooled around. Both of them assumed Chris was asleep at the time. "Well I wasn't sleeping, and I just watched the two of you go at it. I figured if I was able to confuse ya, might be able to distract ya long enough to get you to suck my cock."

Shaking his head slightly, Alex stuck his tongue out at the tiger. "That's playing dirty you bastard." They both laughed slightly, the wolf leaning in and kissing the tiger. He felt Chris resist for a moment and then start to return the kiss. Alex closed his eyes, enjoying the feeling of sharing the taste on his tongue with the tiger, their tongues wrestling in each other's muzzles. Moving forward, he pressed his bulge against Chris' leg, breaking the kiss he whispered. "I've got an aching pussy that's in heat... think my boyfriend needs to lick it." Alex was starting to get into the mood; it wasn't so bad pretending to be the girl for his friend. Glancing into his friend's eyes, they were wide, but after a moment he nodded slowly.

Alex leaned back against the other end of the couch, lifting the skirt up and showing off the panties he was wearing. Sliding a paw down, he hooked the material and pushed it so it was resting under his heavy balls. At least he had that to be proud of, his seven inches of hard wolf cock wasn't as big as the tiger's, but his balls were bigger and they hung down between his legs. Gripping his shaft by the knot, he shook it at his friend. "Come on kitty... give my pussy a kiss." Shivering, he watched as Chris leaned in and ran that tongue of his along the underside of his shaft. That tongue was rather rough feeling as he squirmed in place, his precum started to drool making that tongue feel a little smoother. Alex gently stroked Chris' ears, guiding his friend's muzzle over his cock, letting him suck softly. "Oh that's better..."Rolling his hips slowly, his cock was aching for release alreadly and he knew that he wasn't going to last very long. Closing his eyes, he whined slightly when the tiger's paw wrapped around his knot and squeezed it hard over and over, milking it. "F... fuck I'm going to cum already." Shivering a bit, he kept bucking his hips as Chris eagerly sucking on his length, not stopped when Alex climaxed. Moaning out, the wolf felt his balls drawing tight against his body, flooding his friend's muzzle with his seed. Chris didn't try and pull his head away, Alex held him there regardless. His shaft pulsed for almost a full thirty seconds or so, and he could tell that it was a fairly large load, even compared to normally. It seemed that Chris was able to easily handle it somehow, not letting a single drop drool free.

Blushing brightly, Alex laid there on the couch panting softly. He didn't resist when Chris tugged the panties up over his balls and sheath being very gentle about it. "Don't get changed yet Alex... let's sleep like this okay?" Nodding slowly, Alex was really light headed and not thinking clearly. He scooted on the couch a bit, letting Chris slid up behind him, wrapping an arm protectively around it. Alex sighed softly; it was oddly comforting to have his friend do that, even if he was spooning against him. Softly he panted, Chris' paw was rubbing his tummy and it felt really nice. Alex perked his ears up, Chris whispered slightly in his ear, words slurred slightly. "Go out like this with me tomorrow... stay dressed like a girl. I'll buy you that fancy laptop you've been drooling over for the last month." Blushing, Allowing Chris to nuzzle the side of his neck, licking the fur there.

Shivering, Alex whispered back. "I... I'll need to think about it okay?" He knew that his ears had to be bright red right now, and it was a lot to think about. Alex felt Chris' hips press against his rear slightly, blushing he lifted his tail out of the way, giving an almost silent moan when the tiger grinded that bulge against his rear. Alex closed his eyes, and tried to relax, both of the males drifting off to sleep.

-=The End?=-

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