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Gambling was more about luck than anything. Even ‘systems’ still had chances for error. It still called to people; the adrenaline rush of the risk, the sudden endorphin release of the win, the reward from the gamble. There was a lot that was appealing about it. The downside was when the bet went south and had to be paid.
Rick was used to risks, gambling his life in various ways, living today with no thoughts of tomorrow. It suited him just fine. He even took the occasional wager when he knew that he’d come out on top.
Sometimes, all the smarts in the Multiverse was a match for sheer, dumb luck.
That's why Rick stood there, trying to look as annoyed and put upon as possible, as he upheld his end of losing the bet.
“S-so we done here or-or what? Some of us have m-more important things to do, Lee.”
Stan sat there, a smug look on his face as he enjoyed his winnings. “Don't try worming your way outta this, Sanchez. The bet stakes were, ‘Loser does what the winner wants for a day’ and I sure ain’t sick of this yet.”
Rick scoffed, adjusting his stance as he crossed his arms over his chest. He was decked out in full drag, even wearing makeup. His hair was somehow brushed down from his usual gravity-defying spikes to teased waves of blue locks. His makeup was simple but intense. Black eyeliner swept over his top lids to the side, tapering off close to his templog, enhancing the dark green eyeshadow. A light dusting of blush on his cheeks pulled together by the nude lipstick that covered his sneering lips. His long slender neck adorned with a simple studded collar.
The dark green halter dress hugged his wiry frame, the deep slit ran down to the cinched waist adorned with a black studded belt, the hem billowing out around his knees. Long legs smooth from shaving led down to black high heel feet, two straps just above the ankle and one thick strap across the toes. He was dolled up to the teeth and, despite making such a big stink about it, he looked good.
This dress Rick had liked the most out of the ones that flattered his frame. Green wasn't really his color but it suited him and complimented his skin tone.
-
Stan had made them go to the mall, starting off Rick's end of the bet bright and early. Usually the only people there were around their age, for mall crawl exercises. It made them share a pointed look, a silent promise to end the other if they ever did this.
Stan dragged Rick through a few stores, nothing of note really catching Rick's eye until Stan had pulled them into a posh dress and lingerie shop. Rick gave him a quizzical look, the reality of the situation already dawning on him as Stan tugged him further into the floral scented hell.
“Jus’ pick some stuff out, babe. It won’t kill ya,” Stan said, pointedly ignoring the odd looks they were getting from the two workers behind the counter, whispering to each other.
Rick rolled his eyes but did as he was told. Not much standing out to him at first. A nice skirt and halter top combo, a red cocktail dress, a powder blue summer dress, and a few other outfits. He grabbed them and headed to the fitting rooms. Stan followed, handing him a green dress and giving him a kiss on the cheek - ignoring the lip curl that the fitting room lady gave them - before sitting down in the chair facing the changing rooms.
Rick came out, modeling the skirt and halter top combo, giving Stan a little twirl so the skirt lifted and fluttered around his thighs. Stan nodded approvingly but it wasn't something he'd like to Rick to wear for him. Rick back into the room to try on the next outfit.
Outfits came and went, some put in the ‘maybe’ pile and others handed over to the barely concealed disgusted fitting room attendant. There was flirting and jibes thrown, the occasional brush of a hand over Rick's ass. Surprisingly Rick was having more fun than his original sour attitude would have eluded to.
Rick had shown off this pretty red cocktail dress that Stan liked a lot, sliding his hands over Rick's hips copping a feel before Rick pulled away, smirking.
“I-I-I’ll take this as one to-to put in the ‘yes’ pile,” Rick chuckled as he head back into the fitting room, ready to try on the last dress.
“Ugh, so gross.” It was quiet, an under-the-breath mumble. It was obviously a comment meant for no one to hear, just a way to voice an opinion quietly.
Stan had dealt with a lot of people that said worse louder than that. Did worse than just mumble a comment. It wasn't anything new, especially when he is with Rick. The man always had a tendency to draw attention, be it good or bad, it usually was on him. Yet, here they were, where they shouldn't have to be dealing with this homophobic bullshit.
The fitting room attendant was middle aged, blonde hair pulled up into a bun, face foundation heavy to hide her still visible age and wrinkles. She was fairly average now but you can see that she was once a beauty in her youth. Stan could probably have hit on her if it weren't for how she held herself. Posture straight, nose pointed up, mouth twisted like she smelled something foul, the air of unfounded superiority. She was the type of woman that wouldn't give Stan the time of day and it ticked him off.
He got up to his feet, casually walking over to the little podium near the changing rooms, leaning on top of it with one arm, giving her a large smile. “Ya say somethin' sweetheart? I couldn't hear ya too well - these ears aren't what they used to be,” Stan let out a small, good natured chuckle.
The lady's lips curled even more in disdain before she cleared her throat in such a prissy way that Stan was impressed it could be done. “No sir, I'm sure you just heard things.”
Stan chuckled again, shifting so his body was completely facing the podium, bringing up his other hand, brass knuckles on. “That musta been it. ‘Cause I know ya didn't say nothin’ about us - and especially not him - being ‘so gross’,” Stan paused to look at her, his easy going attitude and smile gone, expression hard and intimidating, “or we would have a problem. We don't gotta problem, do we?” Stan flexed the fingers covered in the solid brass weapon, curling them around it tight.
The woman’s face dropped, looking nervous and scared. It was a better look for her than the one she had before. She swallowed thickly, “N-no sir, not at all. No problem here.” She even tried to force a smile, it looked painful.
“That's what I thought. Now, when he gets out with a new dress on yer gonna compliment him, got it?”
“Y-yes sir,” She whimpered out.
Stan smiled and went back to his chair. A moment later Rick came out in the green dress, looking stunning. Stan got up from his chair with a grunt - getting too old for this up and down crap - and walked over to Rick, grabbing his hand to twirl him around.
Rick rolled eyes and snorted but there was a smile on his face. “L-like this one, huuurrrph?”
“Mm… Love it,” Stan said as he pulled Rick close, mumbling into his neck.
“Uh, that looks lovely on you, um, sir.” The fitting room attendant stammered out, adding a questioning lit to ‘sir’ like she was unsure if that would offend him.
Rick broke the hug to look at her, giving her his own look of disdain before flipping her off, “Yeah, I can pull it off b-better than you eeeever could, wrinkly old bag.”
Stan gave a deep laugh, pulling in Rick for a deep kiss before letting him go to change. He enjoyed the affronted look on her face as he waited.
Rick came out with the outfits that had fallen into the ‘yes’ pile over one arm and the rejects bunched up in the other. He tossed the rejects at the fitting room attendant, laughing as she scrambled to catch them and failing. Stan slid his arm around Rick's waist as the inventor opened a portal and they both stepped through, a Stanbuck fluttering to the floor as the portal closed.
-
“Out of, out of everything y-you could make me do, you get me in-in drag? I build robots for fun. I can create a-and destroy entire univeerrruprses. Y-you could have me create nearly anything you can think of. B-but you choose drag?” Rick scoffed, incredulous.
Stan shrugged, wearing a shit-eating grin. “What can I say? I'm a simple man with simple needs. Plus, I can get crazy science junk from Sixer.”
Rick narrowed his gaze, hands going to his hips. “A-and just what is that supposed to mean, Lee?”
“Nothin', nothin'. Jus’ saying I can't get this from Sixer. Well, I could, probably, but wouldn't like it nearly as much,” Stan held up his hands in mock surrender.
“Pffffbt, whatever gets you o-off.”
“Speaking of what gets me off… why don’t ya come over here and do it?” Stan leaned back, patting his leg, his grin widening.
Rick rolled his eyes, scoffing as he made his way over to Stan, the dress swishing as he walked. “Y-you're just a dirty, old man, h-huh Lee? Wanting your dick in a, in a guy in drag? W-well, where do you want to stick your dick, Lee, my mouth or a-ass?” Rick stood in front of Stan a few inches away, his annoyance from earlier melted into lewd interest.
“There's my favorite deviant. Since ya got such a mouth on ya, why not put it to better use?”
He smirked as he lowered himself to his knees, sliding in between Stan's spread thighs, hands rubbed against the seam of his slacks. “My mouth is al-always put to good use, Lee, yooughu just can’t appreciate it all the time.”
“I ‘preciate it more when it’s wrapped around my cock, darlin’.”
Rick snorted and shook his head as he opened up Stan’s slacks, the other lifting his hips a bit so Rick could slide them down his legs to his ankles, boxers as well. He slid his hands along Stan’s inner thighs, stopping where thighs met pelvis, not yet touching where the other wants his hands to be. His lips pressed against the side of Stan's knee, laying a trail of kisses closer and closer to the semi hard member before skipping over it and kissing down the other thigh.
“Tease,” Stan mumbled, not hating it but getting worked up just the way Rick knew it would. Rick grinned up as he finally came close to the destination, breath ghosting over the heated flesh.
“A-and you love it.” Rick said simply before licking a long, slow stripe across the head.
Stan groaned softly, a large hand went to rest on Rick’s shoulder, thumb brushing against the strip of leather clasped around his neck. Rick gave the head another slow lick, tongue flicking across the tiny slit at the tip. One hand wrapping around the base of the cock to hold it upright as he licked up the shaft, feeling the thick vein throb lightly against the flat of his tongue. His tongue tip pressed against the underside, drawing little swirls and zigzags all the way up to the head, pausing to lap at the glands for a moment before going back down. His free hand stroked Stan’s inner thigh, inching closer before his hand cupped the low hanging sack. Who said foreplay was dead?
“Such a talented cocksucker I have,” Stan had lifted his hand up so his thumb could brush across Rick’s cheek before threading his fingers in the tussled blue hair.
Rick gave him a smirk, leaning in more to press a kiss to tip of Stan’s cock before engulfing the head and most of the shaft in one go. Stan groaned deeply, gripping strands of Rick’s hair tight between his fingers as he felt his cock harden quickly in the wet heat. Rick’s tongue wiggled against the underside before he pulled back to the head, sucking lightly before pushing back down again, further this time. He repeated this until he almost had the entire length in his mouth when Stan pushed down on the back of Rick's head with a pleased moan, feeling his head push into Rick's throat. He held Rick there for a few moments, feeling the throat muscles constrict around his length before relaxing his grip, allowing Rick to pull back with a ragged gasp.
Drool was dripping from Rick's chin, lips slick and swollen and lipstick smeared. Stan smiled down at the other man, eyes half-lidded and pupils blown wide, cock hard and standing at attention.
“Ya look good on your knees, sweetheart. Now get on the bed and gimme a show,” Stan smirked, helping Rick up and giving his ass a swat as he walked towards the bed.
“Y-yes, sir,” Rick emphasized the title as he dug in their bedside table before getting onto the bed, keeping his heels on.
He sat against the headboard, using the pillows to prop himself up as he slumped down, heels pressed flat on the bed with his legs spread wide. He wasn't wearing any underwear. Rick pulled up the dress more, exposing his lower half fully, cock already hard and laying against his stomach.
He made eye contact with Stan as he dragged his hand down his chest, stopping to play with a covered nipple, letting out a lewd, keening gasp before his hand continued downwards. His fingers skimmed along the dip of his hip, just barely missing contact with his cock, as he trailed them over his spread thighs and back up again. His mouth stayed parted, tongue peeking out as moaned and gasped, overemphasizing vocally for his lover's benefit. Once he had finished a third trip down to his thighs his teasing hand wrapped around his swollen cock, giving it a few languid strokes accompanied by a self indulgent moan. Rick's other hand had uncapped the tube of lube, letting some drizzle out onto the tip of his dick, making his hand glide up and down his shaft with ease.
He heard Stan mutter out a swear, his eyes having closed at some point now opened again, seeing his lover palm himself as he watched Rick please himself. It was the best high Rick could ever get; making someone want him so much, to be so turned on by him. The sensation of power and being the object of desire made him lightheaded.
Rick couldn’t wait anymore. He coated two long fingers in the viscous liquid before spreading his legs even more, slumping down a bit more to expose his puckered entrance to his fingers and Stan’s hungry eyes. One finger stroked across the outer ring, making Rick shiver and groan in need, spreading the lube across the wrinkled skin. His other hand grabbed one of his pert cheeks, pulling it to the side to expose himself even more, fingertips digging into graying skin. He licked his dry lips, tasting the waxy substance of the lipstick before he slid one finger deep inside him, a low, keening noise escaping him at the sudden, wanted intrusion.
There was a moment of pause as his muscles twitched around the digit, trying to force it out, before Rick was able to relax, so keyed up from the kinky outfit and the lewd show he was the star of. Rick pumped his finger in and out slowly, building a rhythm before pushing a second finger in, stretching himself out more. At some point, Stan had abandoned his chair (and clothes) to stand at the edge of the bed, getting a better, closer look at his wanton lover. Finally a third finger was added and Rick felt full in such a wonderful way but he needed more, needed to be filled to the brim that his fingers could never accomplish.
He pulled his fingers out slowly, wiping them on the bed, keeping his legs spread wide shamelessly. “W-was that a gouuughod enough show for you, s-sir?”
“The best, babe, as always,” Stan smiled, crawling up the bed to settle between Rick’s spread legs, leaning down to press a kiss against his inner thigh. “Ya really know how to fulfill an order, my obedient little slut.”
“N-now why don’t you fuuuck me, sir, I’m all ready a-and waiting for you.”
Stan ran his hands from the tip of Rick's heeled feet to the crease where pelvis met thigh and back again. “Hmm, I dunno, sweetheart, the show was nice but ya ain't askin' so nice, now, are ya?”
Rick's brow furrowed as he glared at Stan, watching the other smirk with such smug confidence, knowing Rick would give him what he wanted. He huffed before laying back against the pillows more, looking at Stan through his dark lashes.
“Pl-please, siiir, fu-fuck me. I need y-your big, fat cock in my ass so bad. J-just look at it, so lonely with-without something filling it up. I c-can't stand it any longer, please, f-fuck me Lee-- Sir!” Rick said, the pleading dotted with needy whimpers and wanton moans, his hands straying to rub over his body, rumpling his dress.
“How can I deny such a request?” Stan chuckled, his large hands pushing Rick’s thighs open more as he pressed in closer, his hard cock sliding against Rick’s, making him groan low at the contact.
“J-just do me already, mierda!” Rick had lost whatever little patience he had, one long leg hooking onto Stan’s hip, the heel of his foot pressing hard against his ass.
Stan leaned down, kissing Rick deeply, the hint of an amused smile still tugging at his lips. He positioned himself at Rick’s ready entrance, rocking his hips slowly forward, pressing the head in at an agonizingly slow crawl. Rick whined into the kiss, his heel kicking Stan’s ass lightly to get him to move faster, deeper, anything but this teasing gentleness. Hands gripped Rick’s hips tightly, blunt fingertips digging into smooth flesh, before Stan pulled back until just the tip was in and slammed into the hilt. Rick broke the kiss with a strangled cry, his eyes flying open and rolling back as his head flew back against the pillows. He wasn’t granted more than a moment to get used to the sudden stretch, Stan was already pulling back and slamming forward again, keeping a punishing, deep pace.
“Heh, like that, my drag doll? Me fuckin’ ya like the cock slut ya are?” Stan asked, panting out into Rick’s ear before nipping at the lobe, biting his way down his neck, all teeth and tongue.
The rhythm of the thrusting changed from deep, hard strokes to quicker, shallow ones. Stan changed his angle, rolling his hips in different ways until Rick dug his nails into his shoulders hard enough to break skin, his body tensing against him and around him before he cried out, body suddenly jerking as Stan had hit his sweet spot. It was Stan’s aim to hit that spot on every few strokes, making Rick come undone under him, a mess of trembling limbs and incoherent pleas and demands.
Stan grunted as he shifted, the rhythm faltering for a moment, one hand sliding between their bodies under Rick’s dress to wrap around the weeping cock of his lover. He gripped the base tight, making Rick whine in frustration as his building orgasm was denied, hips bucking up and heels digging into back of Stan’s leg and his ass.
“Beg for it, baby, beg for me to let ya cum,” Stan growled out, his pace getting sporadic and choppy as his own orgasm approached.
Rick cursed in a slur of incomprehensible English and Spanish, trying to get Stan to let go, to let him cum. He growled out in exasperation, unable to get what he wanted by his own way, knowing he’d have to do as Stan wanted. “M-mierda, L-L-Lee, let me c-cuuuum! Pl-ple-Ahh!-please!” Rick managed, his stuttering worse with how worked up he was, hoping that it was good enough for Stan because he didn’t think he could make it any clearer than that.
“Mmm.. good, baby, real good. Cum for me,” Stan released his tight grip on Rick’s cock, stroking him quickly as he focused back on thrusting, fast and hard, into the trembling body beneath him.
A few more thrusts and Rick was able to find his release, a choked cry clawing its way out of his throat as he came, spurting his load over their stomachs, soiling his green dress milky white. The sudden tightening, the sounds of Rick spilling over the edge, was enough for Stan to reach his climax as well, giving a few more thrusts before pressing in deep, filling the cross dressing inventor with his seed.
They panted, breathing coming back to normal slow, skin slick with sweat and hair matted down. Stan pulled out carefully before laying next to Rick, head propped up on one hand while the other brushed a few locks of hair away from Rick’s forehead. He leaned down to place a kiss next to Rick’s temple before getting up, groaning, and grabbing a washcloth from the connected en suite. Stan brought the cool cloth to Rick’s face, cleaning off the smeared makeup and sweat, moving the cloth to wipe down the mess between his legs as well.
“S-so have I fulfilled my end of the-the thing?” Rick asked lazily, stretching slightly as he watched Stan tossed the soiled cloth in the bathroom.
“Hmm… Not jus' yet,” Stan said, distracted as he pulled on his clothes.
Rick sat up with a groan that was part irritation and part effort, a hand threading through damp hair. “W-w-what do you mean ‘not jus’ yet’?” Rick poorly mimicked Stan. “What else do you want me to do -uuurp - do?”
“I was thinking we could go to Space Vegas, pull a couple of cons, then get some ice cream at that one place ya like so much,” Stan said, shrugging. He was sitting in his chair putting on his shoes. “Why don’cha change into that pretty little red number? It looked great on ya, babe.”
He stared at Stan for a moment before getting off the bed, brushing down his dress absentmindedly as he walked over to him. Rick bent down to give Stan a chaste kiss, lingering for a moment longer, before heading to the bathroom. “I-I’m gonna shower first, Lee, then we can leave.”
It didn't take long for Rick to shower. He had dried off and tried to brush his hair to something less like his natural spikes, eventually settling on a parted wavy style that still stuck up. A quick application of makeup, dark matte red lipstick and eyeliner. He slipped on a pair of silky red panties and the same heels as before.
Stan had started playing a game of solitaire while he waited. When Rick came out in only panties and heels, he gave a wolf whistle that was returned with getting flipped the bird. Rick rummaged through their closet to pull out the new dress they had ‘bought’ - a simple red cocktail dress the hugged Rick's frame well and flared out at the top of his knees. He looked at himself in the closet's full length mirror, turning this way and that.
“Ya look gorgeous, sweetheart. Ready to go?” Arms slipped around Rick’s waist, pulling him back gently against Stan's broad chest, Stan's head pressed against the side of Rick's arm.
Rick made a low hum in the back of his throat before nodding, grabbing the red clutch that was hanging from a hook inside the closet and turning around in Stan's arms. “I-I always look good. Let’s go, motherfuuuurrpker!” He laughed loudly, giving Stan a kiss on the cheek before he grabbed his portal gun, flicking through the locations before firing out a swirling green opening to their destination.
Maybe they'd get lucky and strike it big. Maybe they would have to flee from casino security. That was the beauty of it, you never knew for certain that the bet will go off without a hitch. Just hope that losing isn't so bad and that the winnings are worth the gamble.