Better as Riley Ch. 01

This is a multipart story featuring a male to female transition along with incest content. As it progresses there will also be themes of cheating.

Themes: Feminization, trap, anal, incest, promiscuity, free use, exhibitionism, creampie, lesbian, cheating

*****

"I can't do it! You don't understand," Ryan whined to his sister Kate.

"What, that you have a crush on Becky?" Kate answered gently, trying to contain her frustration at her younger brother's reluctance.

"What? I don't-" Ryan started but stopped as Kate rolled her eyes.

"She's right dude," Chris, Ryan's roommate, said from his chair. "Everyone knows you like her."

"Yeah, it's super obvious!" Kate exclaimed. "And why the heck do you think I'm trying to help you?"

"Help me? How does dressing me up like a girl help me get a girl?!" Ryan said practically in tears. He had been nervous about the annual Fresh Freshman party, a required event for rushing a frat that involved freshmen cross-dressing.

"Well, it depends on the girl," Kate said patiently. Ryan had always been a bit of a brat if he had to do something he didn't want to.

"What the hell does that mean?" Ryan spit back at her.

Kate sighed. "Well, it helps if the girl likes girls..."

"What?!" Ryan and Chris said at the same time.

"No way," Chris said, "I know she's not full lez, Will told me she-" Kate interrupted him with a jab to the ribs and a sharp glance at her brother.

"Just trust me okay? I know from experience..." Kate blushed as Chris's eyebrow raised, but was happy to see Ryan staring at the ground lost in his own world.

"You okay?" Kate asked, wrapping her arm around her brother.

"So I really have no chance with her?" Ryan said, tears in his eyes.

"Ryan, listen to me," she turned her brother's face to hers. "She asked me to bring you over. She asked to help get you ready for tonight. It's practically all she has talked about for the past two weeks! If you come over and do this right I promise you'll hook up with her tonight."

"Oh," Ryan said his heart soaring a bit. "Sorry, it's just I am nervous about it."

"Ryan, it'll be fun!" Chris said from his chair. "I did it last year and had to get drunk to go, but it turned out to be a ton of fun. The girls fucking eat it up man. They like turning the table, so prepare to get groped! Oh, and make sure you go with the panties, the girls seem to find it hilarious to try and get you to pop a boner if you're wearing them, so you'll get some action that way too."

Kate rolled her eyes, but saw that Ryan was taking the advice serious and joined in. "Yeah that's what I've heard too!" She glanced at Chris. "Chris, do you have any wet? I think that would help."

"Aw, I don't have much left..." Chris said.

"OOhhh, please? I'll make it worth your while," Kate promised with a wink. Luckily Ryan was too absorbed in his own woe to notice the exchange. Chris sighed and handed her a small tab. "Here Ryan, take this."

"What is it?" he asked looking at the small pink tablet.

"It's amazing! It's called wet and it's great! You get super friendly and everything feels and tastes amazing! It always make me so freaking horny too," Kate said before realizing who she was talking too.

Ryan just rolled his eyes. "Swallow it?"

"Nah, let it dissolve under your tongue," Chris told him. Ryan had enjoyed his times with pot and alcohol and knew he needed some help to go through with this. After it dissolved he stood.

"Well, let's go I guess," Ryan said. "Do I need to bring anything?"

"Nope!" Kate said happily, grabbing her brother's hand and waving to Chris. "See you there!"

The two walked to Kate and Becky's dorm as Kate advised Ryan. "Look, just don't sulk when we get there. If you're acting like a brat she won't be into it."

"Okay, I'll try," Ryan said, his body starting to hum as the wet took effect. Soon Kate led him into her dorm room.

"Hey Becky," Kate said as she entered. Kate smiled at the sight of her cute ass wrapped in the striped panties facing her. Becky finished stripping her shorts off then stood.

"You're back!" Becky said turning then waving at Ryan as he entered as well. "Ryan, you made it!"

"Shit, sorry!" Ryan said as his face flushed when he saw her panties.

"Oh don't worry!" Becky said, cocking her hip to the side. "We've all got to get ready together! We girls have nothing to hide right?" She winked and smiled at Ryan, and he felt his cock stiffen a bit at her flirtatious behavior. Normally she was friendly to him, but nothing like this.

"Yeah, I guess," Ryan agreed.

"Did Chris have any wet?" Becky asked Kate eagerly.

"Just gave me one and I gave it to Ryan," Kate said sadly. "We'll have to stick with vodka."

Ryan's eyes widened as Becky bent over to rummage through a dresser, her panties tight against her firm butt. He realized he was staring and tore his gaze away hoping his sister didn't notice, but she was biting her lip and staring with what Ryan realized was her own lusty interest.

"Oh well," Becky said before taking a swig from a bottle of vodka. "Here," she said handing the bottle to Ryan. He took a swig, fighting to swallow the strong alcohol then handed the bottle to Kate.

"So... How does this work?" Ryan asked after each had taken a few sips. Becky and Kate's faces were flush from the alcohol, and Ryan was sure his was too.

Both Kate and Becky started talking excitedly at the same time and Ryan was immediately lost and overwhelmed, his drugged mind unable to follow. He was startled when they each started pulling the rest of their clothes off.

"Hey, weren't you listening, we need to shower!" Becky said as she tugged her panties down, revealing a shaved pussy and trimmed red bush. "Our shower is a no pants zone!" Becky reached out and started tugging on his shorts. In a daze Ryan began to undress, his eyes wide as Becky pulled her shirt off, revealing her small pale breasts.

Ryan pulled his own shirt over his head, and gasped as he caught sight of his sister, completely naked watching him. "Kate, why are you naked?"

Kate laughed and took another sip of vodka, cringing at the taste. "Well I can't shower in my clothes? What's wrong, it's just us girls here. Sisters change in front of each other all the time!"

"Okay, I guess," Ryan said remembering his sister's advice to embrace it. He pulled his shorts off and stood in his boxers unsure if he should continue. Becky made the choice for him, pulling his boxers down, revealing his barely trimmed pubes and a cute dick.

"Oh wow!" Becky exclaimed, reaching out to feel his erection. Ryan gasped at the sensation.

"Shit Ryan!" Kate said laughing.

"What?" he managed to get out, sighing at the sensation of Becky's talented hand.

"Your dick is kinda big," Kate said giggling and moving closer. "I mean, not huge or anything, but on you it looks big!"

Ryan was too busy enjoying the handjob to get upset at Kate mentioning his 5'6" height and sleight build. He had always been small and short. Kate was average for a girl and their older half-brother Zach was over six feet tall, so Ryan's parents had been worried. All the doctor trips had found nothing though, just an unfortunate roll of the dice for Ryan .

"Yeah, it's so cute," Becky said, deflating Ryan's ego. Girls always described him as 'pretty' or 'cute,' leaving him feeling like less than a man.

"You can play with it later!" Kate said, dragging Becky and Ryan towards their bathroom. "Okay, we've only got 4 hours, so we need to be on task," she said sternly to Becky and Ryan, Becky's hand already rubbing him again.

Kate and Becky stepped into the shower. "You coming Ryan?" Becky asked sweetly.

"Um," Ryan said, glancing at his sister again.

"Oh come on, it's not like we're fucking," Kate said dragging him in ten closing the curtain. "You have to forget the whole brother-sister thing. Now it's just girls here." Becky nodded along at Kate's words. "Oh, I know! We need to choose your name! That should help get you in girl mode too. Any ideas?"

"No?" Ryan said, unable to think of any girl names.

"I've got one," Becky said, her head leaned back as she wet her hair. "I think she should go by Riley! Similar enough to Ryan so she won't get confused."

Kate rolled her eyes. "Yeah, and your favorite porn star."

Becky blushed deeply, "Kate!"

"Hey, it's true!" Kate said sticking her tongue out.

"I think Riley is nice," Ryan said, winning him a smile from Becky.

"Alright then, Riley hold tight while Becky and I wash up real fast," Kate said.

Ryan watched as the two girls washed themselves, his erection still at full mast. "Here, wash your hair," Kate held out a fruity smelling shampoo, clearly meant for women. Ryan began soaping his hair and found he liked the smell.

By the time he was done with his hair the girls had their razors out and were grinning at him. "Um, what are those for?" he asked.

"See how smooth we are?" Kate asked, pushing a leg out towards him. "You have pretty sparse leg hair already, but we need you smooth!"

"Okay, sure," Ryan said barely paying attention to Kate since Becky had resumed teasing him. Becky turned and grinned happily at Kate.

The girls soaped up his legs and began shaving, soon leaving his legs silky smooth. "Oh armpits too!" Becky said, standing and raising Ryan's arms, deftly removing the hair. The girls circled him critically. "Whew, thank god you are already so hairless," Becky said.

"Almost done," Kate said, dropping to her knees. Ryan gasped as Kate began soaping up his balls and dick. Kate smirked, "Feel good, Riley?"

"Yes!" he hissed, as his sister's hand stroked him. Kate laughed then moved the razor up and began shaving his balls. "Oh careful," Ryan responded, nervous.

Kate proved to be skilled with the razor and Ryan admired his now almost completely hairless body. His sister had left a trimmed landing strip that matched hers. Ryan ran his hand over his skin, loving the feel of his body.

"That's hot," Becky said, slipping a hand down to play with his butt. "Almost done," Becky said, pushing him over until he was bent at the waist. A few swipes of the razor and Ryan's ass was as hairless as his legs. Becky washed the soap away and leaned in and licked his ass.

"Oh fuck, that's amazing," Ryan said, pushing his ass back against her. Ryan had heard that analingus felt good, but the reality was better than he had imagined. He felt his cock twitch as Becky's tongue slid into his outer ring then drew away.

"MMmm, I love you're cute booty," Becky said spanking him. "Looks just like your sisters."

"It does?" Kate asked. "Here let's see!" She pulled Ryan next to her turned her butt to Becky as well. "Well?"

"Holy shit, you two could really be sisters," Becky said, feeling both their asses. The two siblings had remarkably similar builds and heights. "Twins even!" Ryan and Kate moaned as Becky slipped a finger into each of there asses.

"Oh god, Becky," Ryan moaned.

"Hehehehe, I think Riley likes it in the ass, doesn't she?" Becky asked as she fingered them both.

"Yes, it feels good!" Ryan moaned.

"Fuck I do too," Kate moaned. Becky laughed then pulled away, shutting the water off. "Teasing slut," Kate muttered as she toweled off, causing Becky to laugh.

Ryan towelled off as well, enjoying the sensation of the soft fabric on his smooth legs. The girls led him back to their room and pulled out nail polishes. Soon they each had sky blue toenails and fingernails. Ryan had to admit they looked pretty against his tanned skin.

"Okay, makeup and hair!" Becky said excitedly, placing Ryan in a chair in the center of the room. Ryan watched as Becky pulled out a dark-haired wig that seemed to match Kate's hair. The two girls giggled as they pinned the wig into place. "Sorry Riley, have to go this route until yours gets longer," Becky pouted then kissed his cheek. "Here, scoot over so I can do Kate and you at the same time."

Ryan dutifully moved over as Kate pressed her naked hip against his own, wondering about Becky's comment about his hair growing out. The makeup took longer, Becky carefully applying the same style to the siblings. When she pulled the two in front of the floor length mirror.

"Fuck Riley! You're hot!" Kate exclaimed as Ryan gasped. With the hair and makeup done the same they looked like twins. Well, except for Ryan's cock and Kate's small breasts.

"Oh I am hot," Ryan said fascinated with his transformation and realizing he might actually pass as a girl and escape embarrassment at the party.

Becky grinned proudly then grabbed her phone, "Oh please let me get some pictures?" she begged.

"What, no way!" Ryan said panicking.

"AAwww, please?" Becky begged. "I'll let you take some of me and Kate?"

Kate rolled her eyes, but didn't protest. Ryan hesitated. The thought of having nudes of Becky was enticing, and he had to admit that after seeing his sister naked she was attractive. "I guess it's okay then," Ryan finally said to Becky's delight. She quickly started snapping photos.

"Come on Riley, pose with me," Kate said, turning and pushing her ass towards the camera. Evidently his sister was experienced at this sort of thing, so Ryan decided to follow her lead, pushing his ass out and looking back at the camera.

"Fuck you two," Becky said. "Unbelievable..."

Kate giggled, her own arousal building at showing off for Becky. She grabbed her brother and pressed their fronts together. She could feel his hard cock leaking precum against her and knew her own nipples were hard. The two turned to the camera and smiled as Becky took pictures.

"Having fun?" Kate asked, turning to stare into her brother's eyes.

"Yeah..." Ryan admitted, savoring the feel of his sisters firm body against his.

"Good!" Kate leaned in and kissed him, her tongue briefly darting out to lick his lips. Laughing, she pulled away. Becky captured all of this on her phone, including the string of precum connecting Ryan's throbbing dick to his sister's abdomen.

"Okay, time to do my makeup!" Becky said happily taking a seat. "Kate, show Riley how this is done."

Ryan watched with rapt attention as his sister instructed him on the finer points of mascara, eyeliner, eye shadow, foundation, and other forms of makeup he never even knew existed. His head spun and he struggled to follow along. "Wow, never realized how much effort this all is," he said as Kate finished up.

"Oh, it's not normally this much," Kate laughed. "We're just going all out for the party!" Kate pulled Becky over to the mirror, "What do you think?"

"I love it!" Becky said wrapping Kate in a hug. Ryan quickly grabbed his phone and started snapping pictures. Becky stared into Kate's eyes then leaned in and kissed her on the lips, Kate parting her lips in desire.

Ryan stood stunned, videoing his crush and sister making out and loving every minute of it. The two girls kissed and groped one another for several minutes before breaking apart, their nipples standing proudly at attention as they caught their breath. Becky giggled. "We even now?"

"Oh god yes," Ryan gasped as he lowered the camera.

"Good!" Becky said, slapping Kate's ass. "Let's pick out our outfits!" She walked and opened up her and Kate's closets. "Lucky you gets to choose from any of our stuff!"

Ryan walked over and started looking through their closets. There was a truly stunning amount of clothes and Ryan wondered how his sister afforded everything considering his own money troubles. He looked through the clothes but was overwhelmed. "I don't really know what I'm doing," Ryan said. "Any advice?"

"Hrm," Becky said thinking. "We should definitely go with a cute dress or skirt, that's pretty much a requirement at this sort of event. Oh! And I am thinking some panty hose, help contain this beast," she reached out and gripped his cock.

"I think it would be cute if we matched," Kate said, blushing some.

"OOooo, yes!" Becky agreed happily. "Okay, that narrows it down a bit I think. Let's show you some examples and see what you like." Becky pushed Ryan into a chair then sat on his lap.

"Oh fuck!" Ryan said as her wet pussy enveloped him. Becky giggled and wiggled as she brought up Kate's feed. Ryan sat in disbelief at the suddenness of his first time inside of a woman. The heat and wetness felt better than he could ever imagine and he struggled to breath and not cum as she wiggled on him.

"Jesus Becky, you slut!" Kate said laughing. "How does she feel?"

"Amazing," Ryan and Becky said together then giggled.

"Fuck her cock is actually really nice," Becky sighed as she rocked her hips. Ryan was in heaven and took the feminine pronoun in stride. She could call him whatever she wanted as long as she kept this up.

"Well, stay on task! We don't have much time left," Kate said pointing at the screen. Becky sighed and started scrolling through the pictures.

"Okay, so I think we have three options," Becky said as she pulled up pictures. "First we have this sundress. Kate and I both have one." Ryan took in the photo of Becky and Kate wearing the same flirty sundress, which fell to mid thigh and was strapless. "I think this would be easy for Riley, but also the most boring."

"Yeah, that's not really my style for a party either," Kate agreed.

"Okay then, we have the party dress and the skirt then," Becky said bringing them both up.

"Wow!" Ryan felt his cock twitch inside of Becky as he took in Kate wearing an extremely revealing club dress. It was clear she had on no bra, and the hem fell to just below her ass. The shiny gold material glittered under the lights. The dress was cut deep on the front and sides, revealing substantial cleavage. "I don't know... I don't really have the, uh, form for that," Ryan said pointing at the cleavage.

"That's fair," Becky said, what about the skirt and top then? In this picture Kate was wearing a curve hugging high-rise skirt. While short, it wasn't quite as short as the dress and the top was a more modest halter top that left a slim sliver of skin exposed between her skirt and top.

"Oh, I like this," Ryan said wondering if he could pull off the look.

"Yay me too! Sexy but still comfy," Kate said. "I have the skirt in black and grey and the top in burgundy and purple. Let me find them!" Kate turned and begun digging through her dresser.

"While she does that, we need to take care of this," Becky said sliding off his cock to her knees. "Don't mess up my hair or makeup!"

Ryan gasped as Becky took his cock into her mouth. "Oh Becky!" Ryan gasped. She was obviously experienced as she had no trouble taking his six inches down her throat. Her fingers brushed his balls, then began teasing his rosebud, causing his hips to jerk in pleasure.

"Okay now that is hot!" Kate said when she turned around. Ryan turned to see her snapping a picture. "First time?" she asked as she moved closer. Ryan could only nod in response. "Don't worry about lasting, just enjoy it," she whispered to him. Kate knelt behind him, resting her head against his. Her hands slid across his chest until her fingers found his nipples. "That's it, cum for us Riley, let her taste you," Kate hissed as Ryan exploded into Becky's mouth.

Becky captured what she could in her mouth, but was quickly overwhelmed, cum dripping down her chin. Ryan collapsed backwards, panting as Becky moved up him. She pressed her mouth against his and Ryan was surprised as she fed his own cum to him. The taste was not as bad as he had expected and he was disappointed when Becky pulled away until she started kissing a very willing Kate.

"Whoa," Ryan said as he saw Kate swallowing his cum and eagerly lick Becky's face clean.

"Riley your cum tastes amazing!" Becky said finally after Kate had cleaned her.

"Yeah, wow! A bit of fruity sweetness to it," Kate said looking pleased. "Honestly probably the best I've ever tasted."