Genre:pwp - Tumblr Posts

Something About the South

Relationship: Bill x Richie (Bichie)

Tags: Crossdressing, slight feminization, bottom bill, smut, dirty talk

Summary: When the others are away, Bill and Richie will play.

Read on AO3

    “Come on Billiam. Now you’re just teasing me at this point!”

Richie could hear Bill chuckle through the doorframe.

Bastard.

Bill had shut himself in his room over ten minutes ago (though Richie would argue it was hundreds of years ago) to get ready. He knew it was worth the wait, but Bill was already amazingly beautiful so why did he have to take so freakin long.

“A-alright R-r-richie, I’m r-r-ready,” Bill finally called out through the door.

“Fucking finally.” Richie turned and swung the door open. He meant to strut in in his usual ‘I’m-the-greatest’ fashion, and throw in one of his famous crude remarks, but all thoughts escaped him once he took in the site of the other boy on the bed. He knew ahead time what Bill was planning on wearing (considering he was the one who’d bought it), but damn if Bill didn’t always manage to take his breath away.

“H-howdy thhh-” Bill paused taking a shaky breath before trying again. “Howdy thhh-there P-p-partner.”

Bill was sitting on his bed wearing a pair high-rise faded-blue daisy dukes, a long-sleeved plaid button up tied at his upper waist, a pair of brown cowboy boots, and a slightly ripped straw hat on his head. His short hair was pulled into two very tiny pigtails with bright pink bands, and his face was painted up with just the right touches. He was even wearing Richie’s favorite ruby red lipstick that always left the prettiest little lip stains on the collars of his shirts (The first time Eddie had seen one of those marks he’d freaked out thinking Richie was cheating on Bill. The conversation that followed had been one of the greatest conversations Richie had ever had in his life. Poor Eddie had never quite looked at Bill the same since).

Damn did he love that ruby red lipstick.  

“Why hello there Little Lady.” Bill giggled at Richie’s attempt of a southern accent, his red cheeks flushing darker and spreading to color his neck and disappear under his shirt collar. “What’s a pretty little thing like yourself doing in a place like this?”

“W-ww-w.” Bill snapped his mouth shut. He took a deep breath, opened his mouth to try again, and again snapped it shut after a few tries. He nibbled his lip in frustration, smearing the red off his lips, and turned pleading eyes to Richie. Bill’s stuttered had gotten better over the years, but whenever he got super nervous, or felt too much of an emotion it came back with a vengeance. It also always got worse during their sexy times. No matter how vanilla, or kinky they got Bill typically got so overwhelmed that he’d lose the ability to speak, because his stutter got so bad. This is also why Richie made it so important to focus on Bill during their special times together. He’d written his own little mental dictionary of the noises Bill made and the movements he made, and what each of these special things meant. If Bill bucked his hips a bit and squeezed his thighs that meant he was ready for Richie to move. If, like right now, he bit at his lip and held himself far too tense than he was uncomfortable and embarrassed. Richie needed to make things better. He put on his best cocky grin, and swaggered over to Bill obnoxiously and as ridiculously as he possibly could. This earned him a slight smile. A step in the right direction.

“Don’t you worry Little Lady. I’ve been known to take people’s breaths away.” He stepped in front of Bill and did an over-the-top bow. “It’s a curse you see. I’m just too charming.” This got him a laugh. Almost there. “But you Little Lady, I don’t think I’ve ever seen someone as fine as you. Come on let me see ya.” He reached over and took one of the hands Bill was holding to his chest, and pulled the boy off the bed. He spun him around, making sure to get a peek at the other boy’s ass, and ended his little routine by tugging Bill close and dipping him low. Bill was laughing loudly by this point, arms coming up around Richie’s neck to help keep his balance.

Back on track. Happy Bill accomplished.

“R-r-ri-ichie!”

“Yes, Sweet Thang?”

Bill snorted as he laughed. Richie smiled wide and pulled them both back into a standing position. He tugged Bill close by the waist, and pressed the giggling male flush against his chest.

“You know Sweet Thang you, you never told me what you were doing in a place like this.”

“W-w-well I … I was lo-looking for a r-r-ride.”

“A ride?”

“Yea. I w-was wondering if… if you h-had s-s-someth-thing large and f-f-fun I c-could r-r-ride on?”

“Something large and fun, huh?” Richie smirked tugging Bill closer, so the other male could feel the bulge pressing against the seam of his jeans. “I think I got something in mind perfect for the job.” Bill let out a soft gasp in mock surprise before giggling again, and rubbing up against him.

“I-is that ssso? Y-you think I c-could t-t-take a p-p-peak at it? S-ssee if its t-to my liking?”

“Honey, a sweet sexy thang such as yourself can do whatever you want. I’ll even let you touch it.”

And then they were kissing. Tongues dancing as they pressed and rubbed at each other. Hands wandering and squeezing. Things escalated so quickly that one moment Richie was massaging Bill’s lovely checks through his shorts, and the next he found himself laid out on the bed pantsless with Bill hovering by the bed side with no idea how he’d gotten there. Bill was panting loudly, the red on his lips almost completely smeared off. Richie was pretty sure his own mouth was probably smeared ruby red. He watched as Bill popped the button of his shorts and let the daisy dukes slide to the floor. Richie felt his mouth go dry as he took in the other boy’s weeping erection straining against the tight pair of bright pink panties.  It was the same pair Bill had worn last night when they’d tried out a different scene with the other outfit Richie had bought. A pale pink oversized sweater and a white skirt with long white thigh high stockings. The sex had been slow and drawn out. Bill had been a shy little stuttering mess, acting like a cute little innocent virgin that they both knew he wasn’t.

Now though, now that Bill seemed to be over the nervousness of trying out a new scene Richie could see a fire burning in his boyfriend’s eyes. Things were about to get very juicy.

“So, what do you think Sweet Heart,” Richie gestured to his crotch and gave Bill a little wink. “Does my rig look up to your standards?”

Bill gave him a dirty little grin and climbed on top of him still wearing his boots and panties.

“I don’t know. I thhhink-,” Bill paused and reached into his shirt to pull out a small bottle of lube. Richie watched as his boyfriend poured a generous amount onto his shaft and then tossed the bottle off to the side. “I think I’ll h-have t-to try it out ffffirst.”

And then Bill was shifting forward, reaching around to tug the band of his panties out of the way, and plopping himself down on Richie’s dick with little resistant. Both boys moaned loudly in response.

“Fuck Big Bill, you….fuck!” Richie groaned and reached out to grip at Bill’s thighs. Bill giggled.

“Wh-what? Y-you think I didn’t p-p-prepare myself ahead of t-t-time?”

“Fuck. That’s why you were taking so damn long.” Bill giggled and gave an experimental rock of his hips that sent a wave of pleasure straight through Richie’s body.

“I th-think I’m g-gonna like this r-r-ride.”

“Glad to know my rides to your stands Sweet Heart. I guess as they say I the south, Ride’em Cowgirl!” He followed this with a hard slap to Bill’s ass, that made the other boy squeak and laugh at the same time.

"Whatever you sssay Cowboy.”

And Bill began to move.