Better as Riley Ch. 01

"Ha, you should listen to Kate, she knows her cum," Becky teased as Kate slapped her. The girls giggled as Ryan laid back stunned then helped him stand. His head spun in confusion, the wet and vodka along were enough to have him disoriented, but the quickly evolving situation had him dazed and simply stumbling along as his crush and sister led him down a new sexual path.

"Let's get dressed!" Kate said pointing at her bed. She had laid out the skirts and top as well as a few options for panties. "You can choose the colors you want, but I recommend the red and grey for you," Kate explained. "No bra for this top, and I would probably choose a thong to avoid panty lines, but up to you."

Ryan approached the bed and looked at the clothes. He picked out the red and grey combo as suggested by Kate then inspected the panties. Kate had laid out every conceivable type, from boyshorts to g-strings. Ryan picked up one of the thongs, a cute black and red striped number. It seemed way too small and he moved to set it back.

"OOoo, one of my favorites! I have another just like it!" Kate bent to dig through her undies, treating Ryan and Becky to an unobstructed view of her wet pussy. She stood triumphantly holding a matching pair. "Let's try them on!"

Ryan was eager to see his sister in the thong so went along with sliding the tiny pair of panties up his legs. In his post blowjob state, his cock had shrunk considerably and he was surprised to find that he could tuck himself away in the small pouch. The back of the thong snuggled into his ass and he sighed at the feeling.

"Fuck so sexy," Becky said admiring him. He checked himself out in the mirror and gasped.

"Wow, I look like a girl," Ryan said. Becky laughingly agreed and snuggled against him.

"Yeah you do, I fucking love it," she said, spanking his ass. "Remember though, when you're dressed like this don't think 'I look like a girl.' Think 'I AM a girl.'"

Ryan's cock twitched at the words. "Okay, yeah. I AM Riley after all."

"That a girl!" Becky said kissing him. "Alright, let's get you two in some pantyhose while I get dressed." Kate pulled out three pairs of very sheer pantyhose, and helped Riley into them.

"Oh wow," Riley moaned at the feeling of the slick tights sliding against her hairless skin. "That feels amazing!"

Kate giggled. "Yeah I love pantyhose too!" Kate helped her into the skirt and top as well before getting dressed. Riley admired herself in the mirror.

"Fuck you two! Look at me!" She twisted around, checking out her ass in the clingy skirt. Her legs looked a mile long in the short skirt and for once Riley was thankful for her slim, girlish waist. She frowned as Kate joined her wearing the matching outfit. Her top clung to her small breasts in a pleasing manner and Riley felt a small jolt of jealousy. She shook her head, realizing she was wishing she had breasts! "Wow, I actually look like a hot girl!"

"You really do," Becky said, her voice full of lust. She walked up behind the siblings and groped their asses. "Fuck you two even have the same cute little butts!" She kissed Riley hard. "You are so getting laid later," she promised looking deep into Riley's pretty green eyes. Riley felt her cock harden and was glad for the extra support from the pantyhose.

Kate giggled and pulled Riley away from Becky. "Later though! Shoes!" The two quickly spilled out dozens of pairs of shoes startling Riley. Kate dug through them then tossed a pair of small wedge-heel boots to Riley.

"Those should be easy enough for you," Kate said. "Plus more comfortable to dance in!" She picked out her own pair as Riley slipped them on and zipped them up.

"You know you're lucky Riley," Kate said as she walked Riley test out the heels. "It's tough figuring out all this girl stuff growing up so you're lucky you have Becky and I to help you out."

"I know, thanks!" Riley said cheerily. The heels were not as tricky as she expected and she loved the way they made her legs look longer and her ass perkier. "Holy shit, I am actually going to do this," Riley said realizing she could absolutely pass as a girl.

"Yeah, you feeling okay?" Kate asked.

"Nervous but like also excited?" Riley said. "I don't know... I feel like, curious maybe? It's hard to explain."

"Well don't worry, Kate and I will watch over you," Becky said holding up some earrings. "You aren't pierced yet, but I picked up some clips ons for tonight."

Riley briefly wondered about the 'yet,' but was soon distracted as Becky added the jewelry to her ears. Once Becky and Kate were similarly adorned Becky insisted on selfies and the three girls giggled as they snapped pictures until Kate's phone buzzed.

"That's Chris, let's go!" she said excitedly. She grabbed a small purse and tossed it to Riley. "Put your things in there."

The girls left the dorm and Chris greeted them with a whistle. "Fucking hell! Is that really you Ryan?"

Kate laughed, "It's Riley!"

"Well fuck Riley, you look amazing!" Chris approached her and spun her around. "Dat ass!" He said, spanking her and winning a yelp from her. To her horror Riley realized the attention turned her on and she felt her cock start to grow as Chris fondled her ass despite her recent blow job.

Kate and Becky came to her rescue, pulling Chris off of her. Kate pouted, "No love for me?"

"Aw you know I can't get enough of you," Chris said, pulling her to him by her rear. "Just wanted to see how your sister's ass compared." Riley watched as her roommate felt up her sister, wishing she was involved somehow.

"Well?" Kate asked waiting for an answer. Riley held her breath, ashamed that she cared what Chris thought.

"Honestly can't tell the difference! You two have amazingly tight booties," Chris said happily snaking a hand under Kate's skirt. "Fuck, I am going to be a hero showing up with you three," Chris said pulling Becky and Riley towards him. He bent down and kissed Kate then Becky. Riley felt jealous, then surprised as Chris pushed his tongue into her mouth, causing her to moan and Becky and Kate to giggle.

Chris finally pulled away and Becky kissed Riley hard. "Fuck that was hot," Becky whispered into her ear. "First time kissing a man?" Riley shyly nodded, then gasped as Becky's fingers danced over her cock. "Ooooo, someone liked it," she said leaning into her ear. "That's so hot Riley! You and I are going to have so much fun together. Just remember, have fun and don't overthink it!"

"All right, let's go!" Chris said, herding the girls towards the party. The closer they got, the more nervous Riley was. It didn't help that the alcohol and Wet were starting to wear off. Kate picked up on her sister's anxiety and begged Chris for more of the party drug.

Chris shook his head. "Look I only a few left and I am trying to get lucky tonight," he explained.

"What, you can't get lucky with me?" Kate asked, sliding her hand down to grip his cock through his pants. Riley's eyes widened at the considerable size of the bulge that her sister's fingers played over.

"You're nice, but I'm trying to pull more than one tonight," Chris said enjoying the attention from his roommate's sister. He'd had his eye on her for a while, but had been respectful of Ryan. He was deeply tempted though.

Kate bit her lip considering. "I can promise you me and Becky. No guarantee on Riley, but we can work on her," Kate said seductively, rubbing herself against Chris. "How about it? You finally get me and maybe my sister at the same time!"

Chris groaned then fished the last of his Wet out of his pocket. Kate eagerly grabbed three and Chris popped the last one in his mouth. Riley opened her mouth to protest, telling herself she didn't want any of them hooking up with Chris. Hell, he was really a boy and why would he be okay with his crush and sister having a threesome with his roommate?! He opened his mouth to put a stop to this, but all that came out was a moan as Becky pressed her lips to his, giving him a stern glance as she pulled away.

"Just go with it! Trust me, I will make it worth it," Becky hissed. Riley swallowed her protest.

"We're in luck girls!" Kate said passing the tabs out to Becky and Riley. Riley eagerly placed the tab in her mouth, happy anything to help her relax.

"Yay, thank you Chris!" Becky said pulling him in for a kiss. Riley watched and felt a tinge of jealousy, unsure if it was because she wanted to kiss Becky or be in Becky's place.

Get yourself together Riley! She thought to herself. You're not a girl! You don't like guys! Despite repeating this in her head, she found herself pressing herself against Chris.

"Yeah, thanks!" Riley pressed her lips against Chris who eagerly kissed her back. His hand dropped down and gripped her ass, sinking into her tiny butt.

"God damn Riley," Becky giggled. "First night out and already a slut!"

Riley stuck her tongue out at Becky. "I am just learning from the best!"

Chris laughed then pulled Kate to the side. "Make sure you two keep an eye on her," Chris said. "She's had two hits of wet and I don't want things getting too out of hand."

Kate smiled at Chris. "Aww, don't worry, we will keep her safe!"

Chris escorted the girls to the front of the line and was greeted like a legend by his friends at the door. "Damn dude, we know you're popular, but three girls? And are those two twins?" one of them said, checking out Kate and Riley.

"Just sisters," Kate said laughing and hugging Riley.

"Well fuck dude, save some for the rest of us," another said as he motioned Chris and the girls inside. They were greeted by thumping bass and bodies pressed together in a writhing mass. Some of the drunken mass were hopeful frat brothers dressed in awkward looking skirts and dresses. Riley silently thanked Kate and Becky for making sure she looked good.

Chris turned and grinned, "Anyone want to dance?" Kate and Becky immediately grabbed Riley's hands and pulled her along after Chris into the press of bodies. In Riley's drug addled state the music and lights seemed to burrow into her core, and with Becky's help she was soon gyrating to the music. Becky danced backwards until her ass made contact with Riley, pleased when Riley eagerly joined in. The sensation of being pressed tight against her crush and the second hit of drugs had her cock throbbing and leaking in pleasure.

Across from them Kate similarly pressed her ass against Chris, enjoying the feel of his semi-hard cock. He dropped one hand to her hips, forcing her against him while the two watched Becky and Riley.

"MMmmmm, you like watching them?" Kate asked as she pulled Chris's head close to be heard.

"Fuck yes I do," Chris grunted. "Fuck I know that's really Ryan over there, but honestly I just want to fuck him. Her? I don't care I just know she is hot and that my cock is gonna be buried in her later."

Kate giggled in response, feeling Chris's cock reach full mast. She slipped a hand backwards and gasped. Chris was huge! "Well, I think I can help with that. The idea of you fucking her is exciting and I know Becky is down too. Just not tonight, I think you might damage her with this thing!"

Chris groaned as Kate squeezed him briefly. "Fuck! You think she'll go for it?"

"Just leave it to us," Kate promised. "You just have to swear that you'll still be cool with Ryan. Oh and let me watch!"

"Oh yeah no problem on either front! Ryan's a cool dude," Chris said honestly. "I was a bit worried when we got matched, but he's a great friend."

"Hhhmm, we'll make sure Riley is an even better friend!" Kate laughed. She glanced back at Becky and Riley, and saw Riley shooting her a worried glance. Two upper class men had moved in to dance with them. Becky, with her back to Riley, was enjoying the tall man's attention without seeing Riley's panic. "Uh oh, I think she needs a bit before that! Let's help her out!"

Chris quickly moved over and whispered into the guy's ear. He shrugged and moved off, Kate sliding in behind her sister. "Aww, he was hot!" Kate said into Riley ear. "Not your type?"

Riley's head spun from the dancing and the drugs and the feel of his sister's body pressed against him. Truthfully, Becky's ass and the aggressive attention of the stranger had caused her cock to fully harden inside of her panties and pantyhose. "Um, I don't know..." Riley eventually admitted.

Becky spun around, her ass now grinding against the man still dancing with her and kissed Riley hard. "I think she liked it," she practically yelled to Kate. She grabbed Kate's hand and pulled it down to Riley's hard cock.

"Oh wow!" Kate hissed into Riley's ear. "Fuck that's hot!"

Riley moaned as her sister's and Becky's fingers played over her cock, sighing in frustration when they pulled away.

"Chris wants me on his team for beer pong," Kate said. "You two keep dancing and we'll find you in a little bit!"

Shortly after Kate left, the man dancing behind Becky slid over behind Riley, pressing himself against her ass. "Fuck you have a great ass," he said as he pulled her hips against him. "Too bad your sister had to leave, I would love to have you both."

Becky saw Riley's panicked look and kissed her hard on the lips. "Just relax, I'm here. We're just dancing! Plus you're making me so fucking horny!"

Riley could feel Becky's erect nipples pressing against her and bit her lip as she thought. "Okay, just dancing!" she agreed, wiggling her butt against the guy behind her.

Becky smiled and leaned in and began making out with Riley, much to the delight of the stranger behind Riley. "Fuck you two are killing me here!"

Riley and Becky giggled at his frustration. "Hey, really work him up! It'll be fun!" Becky said into Riley's ear. Riley eagerly responded by sliding her ass up and down the guy's crotch. Her tiny cheeks wrapped around the thick erection the guy was sporting, her thin skirt doing little to blunt the sensation. This went on for several minutes when suddenly the guy reached up and pulled her face to his. Caught up in the moment Riley returned his kiss, his tongue dueling against hers.

When they pulled apart Riley felt overwhelmed by doubt. What the hell I am doing making out with another dude! Becky saw her fear and quickly began making out with Riley to distract her.

"Hey, just let go Riley! I'm here and won't let anything happen to you," Becky said. Riley melted against her. "You doing okay? Having fun?"

"I am... Just not sure..." Riley responded as the man rubbed against her.

"Not sure about liking that big dick rubbing against you?" Becky giggled, her hand reaching under Riley's skirt to tease her cock. Riley moaned, her hips involuntarily twitching against the man behind her. "Fuck that's so hot, feel my pussy!" Becky guided Riley's hand to her panties, which were soaked. "Riley, you are making me so wet! Fucking work that ass!"

Riley gasped as her fingers touched a pussy for the first time, easily entering the hot, slick tunnel. "Wow," she whispered lamely.

"Hehehehe, wow is right! I've never been this wet before!" Becky removed Riley's hand and pressed herself against her. "Let go and enjoy the attention! Dance!"

Riley surrendered to the experience, letting the music and bodies take over her senses. With Becky's helping presence she let herself just enjoy the attention. It was so different than going to parties as a boy. No need to take the lead or deal with the fear of rejection. The freedom from being the actor was amazing and Riley realized she was far more comfortable in this role. It helped that her crush was kissing and rubbing against herself

"That's a good girl," Becky hissed into Riley's ear when it was apparent she was fully invested. "Tease that cock like the little slut you are!"

Riley moaned, "Oh god!" She started sliding her ass up and down, and found she enjoyed the feeling of the stranger's erection between her tight cheeks.

"Yes! Work that cock Riley," Becky instructed staring deeply into her eyes. Riley enthusiastically obeyed, lost in his crush's beautiful blue eyes. Becky moved in closer, pressing her forehead against Riley's. "If you make him cum right here I'll fuck you tonight. I bet you'd like that, wouldn't you? Sliding your hard, girly cock into my hot, wet pussy?"

Riley moaned at the dirty words coming from such an innocent looking mouth. "Oh please, Becky," she begged. Becky smirked as Riley began humping back against the guy even harder. Quickly he tensed and Riley could feel him twitching in his pants. Becky moaned and quickly began kissing Riley when she saw his face tense up. Embarrassed at losing his load while dancing, he quickly slunk away as soon as he was finished. Riley and Becky giggled.

"Wow, why did I find that so hot?" Riley asked after Becky had led her off the dance floor.

Becky shrugged. "I love acting slutty and so does your sister. Considering how similar you two are I'm not surprised you love it as well." Becky leaned in and kissed her again. "I fucking love you acting so slutty too by the way. I really like you as Riley, like a lot!"

Riley stunned and happy let Becky lead her further into the party. They entered a back room to find Chris and Kate laughing as they lost their match. Kate's face was flushed and it was clear she had been having fun.

They made their way to Kate and Chris, Becky giggling and whispering to his sister. Chris pulled Riley to his side, his hand dropping down to her ass. "Having fun?"

"Yeah," Riley squeaked, suddenly feeling shy around Chris. The clear sexual interest from him was confusing but intoxicating after years of being in the background at social gatherings. Riley wiggled against his hand, deciding at least for tonight to go with it. "It's fun going out like this," Riley admitted. "Somehow easier for me?"

"Well you do make a fucking sexy girl," Chris said, slapping her ass. Riley surprised everyone by moaning loudly, drawing the attention of Kate and Becky, as well as Chris's friend Will.

"Oh shit, Kate, I didn't know you had a sister!" Will said walking over to join the group. Will was shorter than Chris and not a pretty man, but fun to hang out with. Will liked crude jokes which Ryan had always found hilarious, especially the reaction he got from girls. Riley shook her head when she realized she was checking him out.

"She's just visiting for the night," Kate said laughing. "Do you like her?"

Chris pushed Riley out into the middle of the group and spun her around for Will's benefit. "Check out her ass, just like Kate's!" he said.

"Damn, what I wouldn't do to get the two of you together," Will said with a lecherous grin on his face. He reached out and groped the proffered ass, whistling. "Ryan puss out? I was hoping to tease him a bit! I owe that bastard fifty bucks after the game last week!"

Kate and Becky giggled and glanced at each other before whispering into Will's ear. His eyes widened in disbelief, shaking his head. "It's true!" Becky laughed, pulling Riley's skirt up and revealing her panty-covered cock.

"Fuck me," Will said in shock. He took a large swig of his drink. "Fucking hell Ryan, you are smokin like that!" Riley blushed at the compliment.

"Th-thanks," she managed to get out, unused to anyone being interested.

"Yeah she is," Beck said sliding her hand around Riley's waist. "You'd still fuck her right?"

"Oh no doubt!" Will said enthusiastically. "Can't turn down an ass like that. Or those fucking lips, just like Kate's!" Will shook his head as if the answer was obvious. "Fuck, with a body like that you should be Riley all the time!" Will accentuated the point with a spank, which caused Riley to stick her ass out even further.

"Oh fuck, I can't wait anymore," Becky groaned grabbing Will and Riley by the hand. "We'll catch you two in a few," she said winking at a grinning Kate and Chris. Becky pulled the two upstairs and into an empty bathroom. She turned around to find Will and Riley making out. Smiling she dropped to her knees, pulling out Will's cock and wrapping her lips around it.