Dwayne Loses a Bet
#1 of Dwayne...
"Ah, screw you guys!" Dwayne muttered as he entered his sister's room. With the door shut behind his back, he walked over and flopped over her bed with a disappointed sigh. 'I had him, too!' he thought, rubbing his paw over his forehead under his glasses. "Damnit," he muttered to himself before standing up and stripping naked.
You all may be wondering how he got into this position, and what his position exactly is. You see, Dwayne is currently living with his older sister as they go to college. His parents rented them the house so they wouldn't mix with the 'common folk.' His sister, however, was invited by her boyfriend to a weekend of snowboarding. That means this house is all his from Friday afternoon until Monday morning.
He invited two of his friends over for a night of debauchery. They weren't going to do much; stay in, get drunk, smoke some pot, and maybe watch a couple movies afterward. Though he and his sister do host parties, he wasn't in the mood to trash the house. Yet.
Kyle was the first one to show up. He was a feline, an orange housecat with darker tabby stripes and long orange hair tipped in blue. His tight shirt and pants showed off his slender, effeminate build, and Dwayne caught himself checking out the cat's ass as he walked by. "Lucky you, a whole house to yourself for a weekend," he said, pouring himself a drink. Along with beer, Dwayne bought ingredients for making Bloody Marys, which Kyle happily took to.
"I know you want me to, but I'm not having a massive party here," Dwayne murmured, crossing his arms. He was a bit shorter than his feline counterpart, but dressed more conservatively in baggy clothes that hid his own feminine build. The Papillon (Small Border Collie with big ears, for those of you who don't know) adjusted his rimless glasses that seemed to fall out of place as he checked out Kyle's ass. He was thankful the feline didn't catch him.
"Fine," he said dejectedly, foregoing the usual garnish that goes with the drink and taking a sip.
It didn't take long for the next guest to arrive, and Dwayne left to answer the door. Joaquin stood there, a six pack of beer in his paw. Joaquin was a white furred hare, and though taller than the other two, he followed the other two's pattern with a slender build. Of them, however, he had the most muscle.
Things started out how he planned. Everyone drank a bloody and a few bottles of beer, they sat around watching some anime and The IT crowd, ate some ordered pizza, passed around a bong, and washed it all down with another bottle of beer. It was around the time they finished the first season of IT crowd that a serious conversation was brought up.
"Of us men, I'd have to say that Kyle is the girliest," Joaquin stated.
"What? Have you never looked in a mirror, Jackie?" he retorted.
"Have you ever not had a sweet ass?" Dwayne said, quickly covering his mouth and blushing.
The two guests looked at the Papillon. Joaquin clapped and pointed with a smile. "Knew it! From the moment I saw you, I knew you had a thing for me!"
Kyle chuckled and said, "I wouldn't have guessed you... you know... swing that way."
"Yeah, I mean Kylie here, sure, but you always try to go out of your way to prove you're manly."
"Hey!" Kyle defended.
"That's not the only way I swing!" he defended.
"What?" Joaquin chuckled softly at his friend's claimed bisexuality.
"And besides! I don't have to make myself look more manly by calling others girly!"
"Are you trying to hide something else?" Kyle said with a chuckle. "Come to think of it, I've never seen you without loose, baggy clothes. Maybe 'you' are the girliest one!"
"Only one way to find out," Joaquin said, undoing the front of his pants. As usual, he wore no underwear, and his sheath was instantly exposed.
"...What?" the other two said with surprise.
"Why do you think it's called 'manhood'? If you really wanna do this game, we have to measure 'em."
"The fuck?" Dwayne stated. "I'm not doing that!"
"Tell you what," Joaquin stood and thought for a moment, his sheath slowly hardening. "We all measure, and the loser has to wear Jenny's clothes for the rest of the weekend."
Dwayne didn't like the thought of going through his sister's clothes while she was gone, but any wrath he receives from her would be worth seeing one of his friends in drag for a weekend. "Alright, I'm in."
"What?" Kyle asked. "Fuck the both of you."
"Oh, shut up," Dwayne muttered. "Unless you're afraid of losing."
Kyle sighed and nodded. "Fine, let's get it over with."
The hare was already at a disadvantage, since he was the only one with a sheath. "Hard, though," Joaquin said once the other two had their pants down.
They agreed and started pawing their cocks. The sight of the other two males pawing their cocks to life turned the Papillon on, and he reached full hardness before the others.
"A bit excited, are we?" Kyle teased with a wink.
"Fuck you," the canine retorted, still pawing his cock to keep it hard.
As soon as they were hard, they each took a ruler and measured their lengths. "Seven-and-a-half inches," Kyle said first.
"Seven," Dwayne said, believing he would be at least an inch larger than-
"Nine-and-three-fourths," Joaquin said triumphantly. The other two looked at him, then down at his ruler. The tip of his cock was just shy of ten inches. "Goddamnit," Dwayne said as the other two cheered and pulled their pants up.
"You know what that means!" Kyle said.
"Yeah, yeah," he said, pulling his pants up and making his way to his sister's room.
"March, woman!" Joaquin called after him.
"Aw, screw you guys!" this was where we started.
He has worn his sister's clothes before. He is not transsexual, but rather, he always liked the way her clothes looked on him. He especially liked the way her panties hugged around his cock. Every movement made his junk shift around within, and the lacy fabric rubbing his privates would send shocks through his nerves. Things go from there, and... well, she doesn't really question how she goes through tissues so fast.
He would have been lying if he said her clothes were the only things of her he likes to play with. He found that his sister is a collector of... adult paraphernalia, shall we say? Various toys can be found in her room, as much as she tries to hide them. Though he has yet to have someone on the giving end of such treatment, he would often fantasize about someone taking him. Sometimes a male, sometimes a herm, and sometimes a girl with a strap-on or a two-way dildo.
When he finally stepped out, the guests stopped and looked him over with wide eyes. Her clothes were a bit small for him, so her black micro miniskirt was even more 'mini,' enough so to show off his cock and balls bulging out of the bottom of lacy bright green panties. On top, he wore a bright green tubetop and a fishnet shirt held in place but bands around his middle fingers. Over his legs, he wore bright green stockings up his thighs and black, knee-high boots with high heels. He even took the time to throw on some bright green lipstick and eyeshadow. He did not have his glasses on either, which he usually did when wearing Jenny's clothes.
"Well?" he asked coldly, crossing his arms. "Is this good enough?"
"A bit more than we bargained for," Joaquin said softly, not hiding the fact that his eyes were wandering over his friend's body. "But it's good." Kyle just sat there staring at the Papillon.
"What?" Dwayne asked before his eyes went down and caught the growing bulges in their pants.
That was when Kyle finally spoke with a grin across his face. "You've done this before, haven't you?"
"W-What?! No!"
"Don't give me that," the feline said. "A skirt, a pair of her pants, or even just her underwear would have been fine. The bare minimum would have sufficed, and yet here you are, dressed like a girl out for a night on the town. Was the lipstick even necessary?"
Dwayne fumbled around before saying, "No. I-I guess not." He started blushing a bit until he noticed they had their eyes locked somewhere. He looked down, and thanks to the tight underwear and the micro-mini-miniskirt, they could plainly see his cock starting to stir underneath. "Hey!" he exclaimed, his blush intensifying as his paws covered his groin. "It's the panties! They just-"
"Hey, we won't say anything, right?" Joaquin said.
"My lips are sealed."
"Good." Dwayne sighed, then looked at the two. "I can take this off then, right?"
"Nope. A deal's a deal."
The canine sighed again. "Alright. What now?" The guests smiled, looked at each other, then back at their friend. "W-what..."
"Well, me and Jackie talked as you were in there. Let's just say, we've agreed that there's more that we can be doing right now."
Dwayne already wasn't sure if he would like this. "What, um... what was it you guys wanted?"
The two chuckled as Joaquin motioned him over with a finger, which the canine obeyed. "To your knees."
Dwayne already knew where this was going, but was not sure if he wanted it like this. Still, he could not stop his friends from undoing the fronts of their pants. He looked up at Kyle, who simply smiled and raised an eyebrow.
"But... but what about Gina?" he asked Joaquin about his girlfriend.
"We're open. We don't just go around yiffing everybody, but I bet she would approve."
It was not completely assuring, what the hare said, but it was enough to give him a go-ahead. He reached both paws up to each guest's crotch. After some soft rubbing over both, he pulled down Kyle's underwear just enough to expose his manhood. He gave the human looking member a slow stroking before going down and suckling on the tip. It wasn't long until Joaquin's cock was hard as well, and the canine moved his mouth to the next hard shaft.
He would switch back and forth between their cocks, alternating in depth and how hard he sucked. He found that he could take their members deeper than he previously thought, and within a few minutes he felt comfortable enough to deep throat all of Kyle's manhood, and could just about touch Joaquin's pubic fur with his painted lips. He drew it out, though, for a full ten minutes before Joaquin couldn't take it anymore.
"I'm gonna cum!" he murred as Dwayne was stroking his shaft. He wasn't sure if he could swallow the bunny's load, but also wasn't sure if he wanted it on his face. He tried to react fast enough as the bunny pawed himself, but as soon as he pulled away from Kyle's cock, the bunny fired off ropes of cum on the canine's face.
Dwayne simply gasped as the first rope landed on his cheek and over a closed eye, but couldn't help but sit there and let him finish. He just opened his maw and waited for him. Another rope shot over his muzzle, and another two went into his opened maw. The final shot just barely missed his maw, and instead traced over the side of his mouth. As his cock started dribbling, the canine went back in and started sucking his cock for more seed.
It was then Kyle muttered, "Oh-Dwayne! " This time, he reacted fast enough. His mouth opened wide and tongue went to the underside of the feline's tip. Kyle pawed himself to release, and most of his seed went into Dwayne's mouth. A stray rope missed, leaving a trail of pearly-white up his muzzle before landing just above the Papillion's closed eye. Again, he started sucking Kyle's tip to milk him dry. Joaquin moved closer, and soon both cocks were tip-deep in his mouth.
Once they were finished, their cocks were still rock hard. Not only that, but it seems their girly friend's own member managed to wrestle out of his panties and stick out from under his skirt. Better yet, the tip of his cock was dripping with seed that overfilled his shaft and begged for release.
"Heh, guess we better take care of that for, huh?" Kyle said with a wide grin.
To be continued... eventually.