Better as Riley Ch. 02

Riley's journey continues with the help of her sister and new girl friend.

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

*****

Ryan woke to a bright beam of sunlight sneaking through a crack in the curtains directly into his eyes. He groaned and rolled over, bumping into a warm body that snuggled against him, a warm ass pressing against his bare cock. Happily he reached down and adjusted his thong to a more comfortable position.

Wait thong? Ryan sat up opening his eyes. He was dressed in a tiny skirt pulled up around his waist revealing one of his sister's thongs failing to contain his morning wood. He looked over at the body next to him, finding Kate naked, her nipples hard in the cool morning air and her crotch covered with dried cum. The previous night flooded back and Ryan felt like vomiting.

He carefully stood and shrugged off the clothes and wig. He grabbed some of his own clothes and snuck into the bathroom. In the mirror he saw a face that belonged on a hot sorority girl after a night out. His makeup was ruined and he had dried cum on his face and neck.

"Fuck fuck fuck fuck," he whispered to himself as he scrubbed his face. The handle on the bathroom jiggled.

"Riley?" he heard Becky call softly from outside the door. "You okay?" Ryan stood silently until Becky called again. "Ryan?"

"Go away," he said, absolutely terrified and ashamed of her reaction. He quickly turned on the shower and jumped in, trying to wash away the previous night. He stayed in until the hot water ran out, no small feat in the dorm.

He could hear voices from his room as he dressed. He couldn't stay in here forever and sighed deeply, ready to face the scorn of his crush, roommate, and sister. Instead when he opened the door he found Chris there alone, talking on the phone. Chris quickly hung up, telling his mom he loved him.

"Dude, what'd you say to her?" Chris asked, a frown on his face. He was wearing only a pair of tight fitting briefs that showed off his firm ass and prominent bulge. Ryan swallowed deeply and tore his gaze away.

"To who?" he asked, confused.

"Becky! She burst into tears and was sobbing her eyes out. Kate had to take her back to their room to calm her down," Chris shook his head. "I thought we all had a great time last night and you were set with her man!"

"I-,I don't know..." Ryan said.

"Well you should figure it out, fuck dude. Becky is a dime! A chance with a piece of ass like that? I'd kill for that," Chris shook his head. Ryan thought about how his last memory was his roommate pounding his crush's pussy as his sister jerked him off. "Look you've still got a chance, send Kate a message and head over." He got up and started dressing. "Don't wait."

"I," Ryan began then sighed. "I'm not sure I can. Last night..."

"You didn't have fun? You looked like you were having the time of your life! Fucking Becky, eating your sister's sweet pussy!"

Ryan felt his resolve waver. "Yeah but I was dressed as a girl..."

"And? You had fun right, sure seemed to me that you were having more fun as Riley than Ryan. Hell I like hanging out with you, but even I have to admit you are better as Riley. You actually seemed to get out of your head for once," Chris said as he pulled a shirt on.

"Oh," Ryan said, surprised at his friend's candor.

"Look, at least talk with her," Chris said as he headed out the door.

Ryan sat and considered his options. He had had fun. Tons of fun. He had lost his virginity to his smoking hot crush! Although a lot more than that had gone on... His face flushed at the memory. How could Chris act so normal after what had happened? Maybe Chris was right he decided. Maybe he did just need to go with it.

Hey, can I come by. He messaged Kate.

Not sure that's a good idea. You really fucked her up. Kate replied.

I know... I want to talk with her.

After several minutes Kate replied. Okay, she wants to see you.

Ryan threw his shoes on and headed to their dorm. Kate met him outside. "Hey," Kate wrapped him in a hug. He was surprised by her friendliness.

"Oh, I thought you'd be pissed," Ryan said, taking in her scent. She clearly hadn't showered and smelled of sex. The scent and memory of how sexy she looked and how she tasted was too much and he quickly broke the hug as he felt his cock harden. She smirked knowingly but didn't mention it.

"No, just worried for my brother and my roommate," Kate said. "You okay?"

"I guess, not sure," Ryan said. He opened his mouth to explain more but Kate cut him off.

"Look last night was a shock for you. I get it. Personally I had a fucking awesome time. With Becky, with Chris, with Riley," she explained then sighed. "I know you've always been... jealous? Envious of me. I know you had a rough time in high school with me being the same grade..." Kate hesitated. "With me being the sexy, popular stereotype of the perfect little cheerleader. Of not living up to Zach's reputation," Kate continued, alluding to their older half-brother. "But last night was the first time I have ever actually seen you relax around me. You just seemed way more relaxed as Riley."

Ryan chewed his lip. So far everyone seemed to like Riley better, and he had to admit he could see Kate's side. In high school he had been jealous. She had boyfriends, was popular. He was the small little brother that got invited as an afterthought.

"Just think on it," Kate said then grinned. "Besides, I have always thought I was sexy. With Riley their I can get off to myself without a mirror and feeling like a total narcissist," Kate laughed as Ryan's jaw dropped. "Well come on, I'll let you in."

When Ryan entered and saw Becky he was immediately ashamed. Her makeup was ruined from crying and she was unable to meet his eyes. Kate glanced at both of them. "I'll go get some coffees? Be back in twenty," she said as she slipped out.

"I'm so-," Ryan started when Becky interrupted him.

"No, I'm sorry! I got too wrapped up and pushed you too far," Becky said. "I know I am... Kinky? I guess that'll work for lack of a better word. I just, I know you've had a crush on me. Kate would always tease me when we were... together. At first I wasn't interested. No offense, but I date girls and the guys I like to fuck are-," she hesitated.

"Manly?" Ryan offered, his heart deflating.

"Yeah exactly! Big muscles and big cocks," Becky said then realized how it hurt Ryan. "Sorry... It's not that I don't like you..."

"You just like Riley better?" Ryan offered, remembering his sister's and roommate's words.

"Yeah exactly! I mean I like you too! A lot actually," Becky blushed at this.

"Oh you do?" Ryan said surprised.

"Yeah... Kate kept bringing you around, making sure we were hanging out, and then when she brought up helping you dress up for the party I realized I was into you. That you would make an amazingly cute girl!" Becky seemed excited now. "Fuck, just thinking about you as Riley turns me on."

Ryan laughed nervously, but felt his cock twitch. "Thanks? I was pretty hot..."

"Hell yeah you were!" Becky giggled. Ryan was glad she was smiling. "What about you, are you okay? Last night was a lot..."

"It was," Ryan agreed. "I honestly don't know. I thought for sure everyone would be teasing me, calling me gay. That I would be a laughing stock..."

"Well, eating out another girl is pretty gay. I should know," Becky said with a grin causing Ryan to roll his eyes. "I know what you mean though! I still haven't come out to most of my family," Becky said seriously. "Trust me though, you were popular! Here look at this."

Becky opened up various messages. One was from Will asking to give him a heads up if Becky and Riley were ever headed out together again. There were several screenshots from Kate of guys asking if her "hot sister was single."

Ryan giggled to himself, oddly proud of the attention. "Wow! It's kinda nice to be wanted like that..."

"Yeah it is!" Becky laughed and snuggled against Ryan. He glanced down and his widened as he saw right down her low cut shirt and took in her hard nipples.

Ryan decided to take a risk and leaned over and kissed her. She eagerly kissed him back and soon the two were rolling around on her bed making out. Suddenly she pulled away.

"Um, can I dress you up a bit?" Becky asked, her eyes wide and innocent looking.

Ryan felt his twitch at the request. "I guess," he said trying not to sound too eager.

Becky yipped with joy and before Ryan could move she was applying mascara and lipstick. "Okay, maybe just panties this time, I don't want more in the way. Help me pick out a pair," she led Ryan over to his sister's clothes and began rummaging through her panty drawer.

Ryan's eyes found the thong his sister had been wearing last night. The crotch was stained with what was clearly cum, and a lot of it. Becky followed his gaze and grinned. "Oh, those would be perfect!" Ryan blushed as Becky helped him into the thong and he sighed as it nestled between his cheeks.

"How do I look?" Ryan asked nervously. Becky was staring at him in a predator manner that excited and frightened him. She advanced and he felt himself backing away.

"Where do you think you're going slut?" Becky said grabbing him by his hair. She pulled him to over to the her bed and laid back, spreading her legs. "I hope you like the taste of cum, I haven't showered and Chris fucked me twice after you passed out last night."

Ryan felt his mouth water a little bit and pushed her thong to the side, lower his face to her pussy. Becky moaned as he went to work, sliding her labia between his lips and running his tongue along the length of her pussy. "MMMmmm," he moaned as he savored the taste and feel of her pussy.

"Oh god Riley, so good," Becky moaned, raising one hand to play with a nipple. "Oh fuck, you're gonna make me cum!"

Ryan grinned and backed off, deciding to tease her. Becky moaned in frustration, but let him guide the pace. He worked lower until his mouth covered the entrance to her vagina, his tongue slipping into to taste her and Chris. He swirled his tongue around, and Becky moaned as it brushed against her asshole.

"Oh I can't take it anymore," Becky grabbed his head and held his face in place as she began grinding against him. "Oh FUCK!" Becky yelled as she came, releasing a torrent of juices down his face. He continued to softly lick her until she pushed him away.

"Well I see you two made up," Kate said, causing them both to jump. She was standing by the door coffees in hand with a big grin on her face. Ryan jumped and tried to cover himself, but Kate just rolled her eyes. "Really? Remember, just us girls here," she said with a wink.

Ryan laughed and relaxed. "Sorry, we got carried away."

"Oh don't apologize, that was hot," Kate said, setting the coffees down. "Hate to be the spoiler, but Becky we have to meet for that psychology study group in 10 minutes."

"Shit!" Becky jumped up and began gathering things for a quick shower. "Sorry Ryan! Um, call me? Please? I'd love to go out... Sorry to leave you hanging." She kissed him and slipped into the bathroom.

"Nice work!" Kate said, giving Ryan a hug and sliding her hand across the front of his thong.

"Thanks?" He shivered at her touch. "I should probably go."

"Yeah! You'd better call her," Kate said doing her best to sound threatening.

"I will!" Ryan promised, grabbing his boxers. Kate stopped him.

"You look better in mine," she said as she grabbed his boxers and tossed them in the trash. "Just try it?"

"...okay," Ryan finally agreed, pulling his shorts on over the thong.

*****

"Dude heard it went well!" Chris said as he entered their dorm that afternoon. Ryan looked up from his textbook. "Huh," Chris grunted out as he noticed the makeup on Ryan.

"Yeah, you okay?" Ryan asked, confused.

"The makeup is cute," Chris said shaking his head. "It's a bit confusing, the boys clothes and the makeup."

"Oh no!" Ryan said, horrified. He had completely forgotten about the makeup! He blushed and moved towards the restroom. As he tried to hurry he tripped, sprawling to the ground. Chris's eyebrows rose as the thong peeked out from under the shorts.

"Here let me help you," Chris said, pulling him to his feet. Ryan felt his heart skip a bit.

"Sorry... I didn't mean for you to see this," Ryan said.

"No worries! Besides, like I said, I prefer Riley," Chris said with a wink.

Ryan scurried off to the bathroom, washing of the makeup before returning. The two hung out and played video games for a few hours, Chris occasionally texting. As they shut down the system to finish their homework Chris turned to Ryan.

"Hey dude, so I just wanted to run something by you," Chris said seriously. "I had a great time last night with Kate. She did too. I was thinking of asking her on a date, but you're my friend so I wanted to see how you felt about that."

Ryan's first reaction was remembering the arousing sight of Chris fucking his sister. He pressed that down and tried to act cool. "Just treat her okay? You're a good guy, so I don't have any problem with it."

"Awesome!" Chris said and wrapped Ryan in a hug. "She's an amazing girl, so I am lucky she's interested!"

"Yeah," Ryan agreed, trying to push away the feeling of arousal coursing through his body at the close proximity of his roommate's body. The two were soon focused on their work, Ryan struggling to write an English essay while Chris seemed to breeze through a chemistry problem set.

*******

Ryan looked at the box sitting on his bed and reread the short letter for the third time.

Hey Ryan!

I picked out some things for you to help with the date this weekend! I know these are some of Becky's favorite looks and because she likes them on me, she will love them on you! I recommend practicing your makeup skills, but I can come help too. Oh, I scheduled you a haircut on Thursday too. I'll meet you.

Love,

Kate!

PS Get Chris's opinion on the outfits!

PPS Bonus points if you only wear panties this week.

Kate had dropped the package off with Chris while Ryan was away. He nervously opened it and was shocked to see three complete outfits, shoes included. There was also makeup and some clip-on jewelry.

Ryan quickly closed the package as a key jiggled in the door. Chris entered, sweaty from the gym.

"Oh, those the clothes?" he asked as he tugged his gym shirt off, revealing his muscular torso.

"Um, yeah? You know about them?" Ryan asked, surprised.

"Yeah! Kate was deciding between a few outfits so I gave my input," he said. "Personally I like the thigh-highs and plaid skirt, but Kate says that's too much for a first date." Chris had a big grin on his face. "Well, just let me know if you want any help," he said as he stripping the rest of the way naked and walking past Ryan to the shower with his cock swinging freely.

Ryan bit his lip and peeked at the other outfits, oddly excited. He saw the school girl like outfit and quickly agreed with Kate. There was one dress, a small summer dress that Ryan liked. The last outfit was one Ryan was familiar with, often seeing it on Kate. He liked this one, and decided he wanted to try it on.

The shower had just turned on, so Ryan figured he had time, quickly stripping naked. He grabbed a cute pair of blue panties and slid them on. These weren't a thong, but still revealed about half of his ass and felt nice against his shaved skin. He picked up the shorts and slid them up his legs. These were high-waisted with a very short inseam. The crease where his butt and legs met was exposed, but that was how they fit his sister as well. The top was a loose, off the shoulder crop top that revealed his belly button.

Lacking a good mirror, Ryan decided to take a few selfies, very pleased with the results. He decided to send one to Kate to get her opinion.

HOT! That's the one right? She replied within minutes. What did Chris think?

I didn't show him Ryan replied.

Well you should ;p she replied.

Ryan wasn't sure he was ready for that yet. The shower shut off and he scrambled to change, dropping his shorts as he moved back to his bed only to trip and crash against his bed, slamming the frame against the wall.

The bathroom door flew open, "Everything okay?" Chris called concerned before spotting his roommate's predicament. Ryan was leaned over the bed, his feet tangled in shorts, his girly ass and panties on display. "Oh shit!"

"Ugh," Ryan said pushing himself up enough to turn. Chris was approaching, dripping wet and naked. His cock hardening. "Yeah, I'm okay." Ryan blushed and tried to avoid checking out his attractive roommate.

Chris was now standing right in front of Ryan, and his cock was fully erect. "Alright cool. The noise startled me is all. I should go dry off." Ryan watched his muscular ass as he walked away and decided to ask for his opinion.

"Wait, maybe you could give an opinion? Kate said you would..." Ryan said. Chris stopped and turned, his cock waving around.

"Yeah sure!" Chris said with an eager grin. Ryan quickly pulled on the shorts and posed, turning to show his ass. "Damn, what a booty!" Chris said, closing the gap to slap his ass. Ryan laughed and turned to look back at him. "Hey, you should toss on some of the makeup too," Chris said gesturing at the box.

"Okay sure," Ryan grabbed the kit and headed to the bathroom mirror. He decided to stick with mascara and lipstick for now, and carefully applied it. Not as good as Becky or Kate's work, but still cute he though. In the mirror he saw Chris taking photos and turned and gave a few poses. "Send one of those to Kate please."

Nice work on the eyes! She replied. Ask Riley to take care of boner before you hurt yourself!

Chris laughed at the reply and showed it to Ryan. "Shit your sister is something," he said shaking his head. His erection throbbed though and Ryan licked his lips as a huge drop of precum leaked out.

"Um, you sure you don't want Riley to help?" Ryan felt himself slipping back into girl mode. She looked up at Chris and batted her eyes at him. "I could try..."

"On your knees slut," Chris said eagerly. Riley obeyed, her eyes widening in shock. She opened her mouth to offer a handjob when Chris shoved his cock in. "Oh fuck yes," Chris moaned. "I've always wanted a live in slut!"

Riley moaned around his cock, surprised both by his aggressiveness and her own eager reaction. She swirled her tongue around the head of his cock, looking up into his eyes like the girls from pornos. He had his camera up, taking a picture. Riley tried to pull off, not sure she wanted pictures out there, but Chris kept her mouth in place.

"Don't worry, just sending it to Kate," he said, tapping away with one hand. Suddenly his phone started buzzing. "Hey Kate," Chris said as he answered it. "Like the view?" It was clear she was on video chat.

"Yeah so hot," Kate said breathlessly. "Riley, make sure you swallow and don't spill on that top, it's one of my favorites."

Riley just moaned in response. Chris had worked about half his cock into her mouth, and was slowly thrusting. She could feel an inch or two enter her throat with each thrust, surprised at her lack of gag reflex.

"OOOooo, looks like we have that talent in common too," her sister moaned as Chris forced the rest of his cock down her throat. He moaned at the sight and his cock swelled as he came directly down his roommate's throat.

"Ah fuck, I needed that!" Chris said as he pulled his cock out.

"What it's been like three days since we fucked!" Kate said laughing.

"Hey, I like to cum daily and I don't jerk off," Chris said shrugging. "Thanks Riley! I think that's the outfit!"