Open on Literotica

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."
"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.
"MMMmm," Will moaned into Riley's mouth. "Shit you give great head!"

Riley looked down to find her crush happily sucking on a cock that put her own to shame. "MMmmm, I love your huge dick," Becky moaned around Will, tugging on Riley's hand until she knelt as well. Riley found the site captivating. She'd heard about the rumors of Will and Becky hooking up and clearly they were true. Riley felt a small tug of jealousy, wishing Becky was sucking her cock, but this was quickly overwhelmed by an arousal so deep and primal she could think of nothing else. Becky was an amazingly beautiful girl, and the site of a fat dick sliding in her mouth only Riley want her more.

"Come on Riley, help her out," Will said pushing Riley's head towards his cock. Riley's mouth went dry at the thought of touching someone else's penis. Rather than being disgusted, RIley felt a certain amount of unease at how people would think of her. Was this really a line she was going to cross? She hesitated, and looked at Becky, who was happily sucking about half of Will. Becky raised an eyebrow at her in obvious invitation.

"Okay," Riley whispered sticking out her tongue and leaning forward. She licked the exposed side of Will's dick, finding the firm yet soft texture and heat from his erection pleasant. Up close his cock was even more impressive. Riley knew her cock wasn't small, but this was definitely bigger and more masculine and she could understand why Becky was worshipping it. She wondered how it could fit inside anyone.

"Shit yeah!" Will said as he felt Riley tongue play along the underside of his cock. "God damn do I love freshmen sluts!" He put a hand on the back of each girl's head, gently encouraging their actions.

Riley broke her gaze from Becky and glanced up, Will catching and holding her gaze. The look of pleasure and need on his face made Riley feel powerful, like she controlled his whole world in this moment. She wrapped her lips around the edge of his cock and smiled to herself as Will moaned and twitched.

"I need some dick," Becky said popping his cock out of her mouth. She stood and pulled her dress over her hips and dropped her panties. Riley stared in awe as the lithe redhead revealed her pussy, the scent filling the air. Distracted, she didn't notice Will until his cock slipped into her mouth. Reflexively she moaned and swirled her tongue around him.

"Hell yes," Will said, "She's a god damned natural!"

"Hey! I need some cock over here!" Becky giggled, pulling Riley's head off of Will then leaning over the sink with her legs bent.

Will grinned and winked at Riley. "Your girlfriend is one horny slut," he told Riley as he stepped up behind Becky. Riley reached down and began stroking her cock, fascinated as he watched Will's massive organ slide into Becky's tight pussy.

"Oh god," Becky moaned. "Something about a live cock that a strap-on just can't match!"

"Ugh," Will grunted as he fucked her. "You still doing the whole lesbo thing with Kate?"

"Oh god yes, have you seen her? She's so hot. We'd date if she was more into girls, but I have my eye on Riley now," Becky reached down and began playing with her clit. "She's good with her tongue too! What I wouldn't do to have her on my clit now!" Riley's head swam as she realized his sister and crush had been sleeping together.

"Fuck just use Riley, she's game," Will said, reaching over and pulling Riley closer. "Still can't believe a girl that likes cock as much as you doesn't date guys."

"Oh please, Riley?" Becky said turning back and giving her best puppy dog eyes to Riley. Riley bit her lip and nodded, eager to taste Becky's pussy for the first time, and to get her mouth back on Will's dick. Becky spread her legs further and Riley slipped underneath the couple. Will's fat cock glistened with Becky's juices as he pounded into her.

Riley eagerly began licking, not caring who her tongue and lips made contact with. Becky and Will moaned in pleasure at the added sensation. "Oh fuck, that's too good," Will moaned. Riley could see his ball and cock spasming and smiled to herself.

"Fuck! Don't come yet!" Becky yelled, grabbing Riley and repositioning her tongue on her clit. "Me first!" Riley complied and began sucking on her clit. Soon Becky was rocking her hips and screamed as she came, far harder than any orgasm she'd had before. Riley struggled to maintain contact with her, eventually succeeding only when Will held her hips tight and began to cum inside of her.

Riley watched as Will's cock swelled and pulsed. Overcome by the beautiful site, she shitted her lips to his cock and balls, bringing him to new heights of pleasure. She eagerly licked at their union and was rewarded as cum began to leak from around Will's thick shaft. Riley eagerly lapped up the sticky cum.

"Well fuck," Will said as he slumped against Becky. "You two have ruined me. I am going to be chasing this for the rest of my life!" There was a pounding on the door.

"Yo Will, finish up in there, we're up!" someone called.

"Gotta go!" Will said with a laugh, pulling his softening cock out. Neither girl paid attention to his exit.

Becky grabbed Riley's head, quickly flipping around and grinding her messy pussy against her mouth. "Oh fuck, clean me up slut!" Riley moaned in pleasure, eagerly sucking and licking the cum out of her. Becky shuddered in pleasure, a smaller orgasm washing over her. Finally she pushed Riley away.

"Thank you," Riley said shyly.

"What!? I should be thanking you!" Becky said smiling down at Riley. "You are amazing! So fucking beautiful just like your sister, but with a nice cock for me to play with too!"

"Th-thanks," Riley said smiling.

"Oh hold that smile!" Becky fumbled for her phone and snapped a picture of Riley. Her face had cum dripping down her chin and smeared over her lips. "Fuck you look hot like that!" She showed Riley the picture.

"Wow... I actually look like a teenage slut," Riley admitted. She studied the photo, proud of the way she looked for once in her life.

"Hell yeah you do! Gonna see this picture everytime you text me!"

Becky helped her clean up and fix her makeup and the two girls left the bathroom, Riley feeling overwhelmingly horny.

"So, are you and Kate," Riley started. "You know together?"

"Oh, that?" Becky said laughing. "We take care of each other sometimes. Look I would absolutely date your sister. She is amazing, but she's only interested in fucking girls, not dating them," Becky said with a shrug.

"Oh, I had no idea," Riley said. "And you...? Will said you don't date guys."

"Yeah... I'm kinda the opposite of Kate. I love to get fucked, but I'm done trying to make relationships beyond fucking work with guys," Becky said with a shrug. "I really can't explain it. I like attention from guys and I like hooking up, but outside of that I just don't feel the spark. Doesn't mean I can't have fun though!"

"What about us though?" Riley asked, knowing she was a really a he.

"I'm having fun with us. I don't know. I try to live in the moment and I like you better as Riley!" Becky replied, swatting Riley's ass before she could respond.

Becky pulled Riley back to the party. Riley wondered what this latest revelation meant. It seemed like Becky was interested in her. In him? She was confused, but soon distracted as Becky pulled her into the press of bodies and the party atmosphere swept over them.


"You like watching her, don't you?" Becky whispered into her ear. The two were snuggled on to Riley's bed, watching Chris and Riley hookup. They had moved the futon mattress to the floor, and Chris was currently pounding Kate's small body from behind. Kate was skinny, just like Riley, but despite her slight frame the force of Chris's thrusts caused the flesh of her ass to ripple and her small tits to bounce.

"Oh fuck me Chris! Fuck me Daddy..." Kate moaned. Chris moaned and began spanking her. Kate wiggled her ass in response.

"Yes," Riley finally admitted. It was honestly one of the hottest things she had ever seen.

"Do you think Kate is hot?" Becky asked, pulling Riley's pantyhose down and off. Her fingers teased Riley's hard panty covered cock.

"Yeah..." Riley moaned.

"What about Chris?" Becky teased.

"What? I am not into guys," Riley insisted, although her eyes strayed to Chris's thick cock.

"HHmmmm, not even that dick? It's so big," Becky teased. She gripped Riley and stroked her a few times and nibbled her ear. "I bet you wish that was you getting fucked."

"Oh god yes," Riley hissed. Becky giggled and pulled her off the bed and towards the couple.

"Can we play?" Becky asked in a girlish voice. Chris grinned happily and Kate turned, her face filled with lust.

Chris reached out and grabbed Riley, pulling her in for a kiss. Despite her earlier protestations to Becky, Riley melted into the kiss, eagerly sucking on Chris's tongue. Becky giggled and popped her cock out of the thong and into her mouth.

"Oh!" Riley gasped. She was already on the edge of cumming, having endured hours of teasing. Becky sucked greedily, but pulled away before she could finish. "Oh please, I need to cum," she begged.

"Oh, so you don't want to fuck me?" Becky asked pulling her clothes off. She laid on her back, positioning herself so she could kiss Kate while spreading her legs.

Riley quickly slipped between her legs. Becky pulled her down into missionary, alternating between kissing Riley and Kate. Riley fed her dick into Becky, savoring the feeling of finally being inside a woman.

"Fuck that feels good," Becky moaned, rocking her hips. Riley could only nod in agreement, focusing on not cumming too quickly. Becky quickly picked up on her hesitation and pulled her down. "Hey, don't worry about not cumming. Just enjoy yourself!"

"But I want you to have fun to!" Riley insisted, eager to please her.

"I'm having fun! Plus Chris and Kate can help finish me off," Becky said with a lusty grin as Riley's cock twitched. She knew that shouldn't turn her on, that she should want Becky all for herself, but after watching Will use Becky she was eager for another show. Becky began sliding her hips up and down and dropped a finger to her clit. "Fuck Riley, so good..."

"Wow, that's hot," Chris said, his fucking slowing as he watched Becky and Riley. Kate turned her head and took in the sight.

"Wow, yeah," she said, reaching out to stroke Riley's butt.

"Uunnnh," Riley moaned, as Kate's fingers trailed down her crack and began teasing his ass. The sensation was amazing! "Oh god Kate, oh fuck!" Riley grunted as she came, her asshole twitching as Kate rubbed the tight ring and giggled. Riley joined in the giggling as her orgasm ended. "Wow!"

"Good first time?" Becky smiled as she pecked Riley's lips and cheek.

"Yes! So good!" Riley said, wiggling her butt. Kate was still playing with her asshole and it felt good! An involuntary moan escaped her lips as the tip of her finger worked itself in. "Oh that feels good!"

"Keep it up Kate! She's getting hard again!" Becky cried, clenching her pussy and helping Riley maintain an erection. Several minutes later Kate was working the first two knuckles of her finger in and out of her sister's ass and Riley was fully erect again. Becky pushed her off, "My turn now," she said, mounting her.

Becky rode her aggressively, playing with her clit. "Fuck, that's it!"

Kate watched, aroused at her friend and sibling fucking. Chris suddenly withdrew and picked Kate up, setting her down on Riley's face.

Riley watched in awe as her sister's pussy lowered onto her face. She eagerly started licking and sucking it. The drugs and alcohol and hours of being teased while watching her sister flaunt her body drove her past any concerns of incest. The taste was different than Becky's, but no less tasty.

"Oh god, we shouldn't-" Kate started to protest before Riley found her clit. "Fuck, she's good..." Kate rocked her hips then leaned forward to kiss her roommate.

Spying his opportunity, Chris knelt over Riley's head and slid his cock back into Kate from behind. "Fucking sluts," Chris grunted. Chris began roughly fucking Kate, spanking her ass hard and causing Riley to struggle to keep her lips and tongue working. Becky grinned and began roughly tweaking Kate's nipples.

The sensation was too much for Kate, and she came immediately, her pussy tightening around Chris. Chris bellowed as he began pumping his cum into her bare pussy. Beneath them Riley happily sucked their combined juices, swallowing what she could. Riley found that Chris's cum tasted much better than Will's, although still not as good as her own.

Eventually Kate's legs gave out and she collapsed weakly to the side. Chris's cock stood hard, still in need of more attention. He grunted and pulled Becky off of Riley, mounting her roughly.

"Oh! Yes, fuck me Daddy!" Becky cried, causing Kate to giggle. Riley mewled in frustration, causing Kate to giggle and slide closer. She wrapped a hand around Riley's erection, causing her to gasp.

"They're hot aren't they?" Kate whispered into Riley's ear. "Just enjoy the show. When she gets like this she just needs a good hard fucking from a thick dick. If you're going to date her you'll need to get used to sharing. Don't worry though, she's not jealous either."

Kate's words drove her sister over the edge, and Riley came helplessly over the futon as she watched her crush get the fucking of her life. Exhausted Riley collapsed and fell into a deep sleep.
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