Better as Riley Ch. 02

Riley sat back stunned, her cock hard in her panties and shorts. "Y-you're welcome." She was crazy aroused. "Um, I can help you out you know. If Kate's okay with it."

Kate laughed loudly. "Aww, look my little sister is cock hungry! Shouldn't you be asking your girlfriend?"

"Oh. Shit, I should," Riley said.

"Feel free to use Riley whenever you need," Becky's muffled voice said, startling Chris and Riley.

"Hey, don't talk with your mouth full," Kate said, pointing the camera down so Chris could see Becky licking her pussy. Chris turned the screen so Riley could see, winking at her. "Ummm, yeessssss," Kate hissed. "Well I gotta go! Cya Thursday Riley!"

Chris tossed the phone on his bed and headed back to the room leaving Riley on her knees, the taste of cum in her mouth. She stumbled to her feet, stripping the outfit off and hopped into the shower, quickly rubbing her cock to an orgasm.

When Ryan re-entered the room, a towel around his waist Chris never mentioned the blowjob, instead laughing with him about some stupid internet video as Ryan got dressed. He hesitated, but dropped the towel revealing he had the panties on still. Chris watched but never commented as Ryan got dressed.

Thursday came quickly with no further encounters with Chris. Ryan had been willing, even hoping for Chris to initiate something, but he hadn't brought it up. It was mid-afternoon and Ryan was headed to Kate's dorm. Inside she greeted him with a warm hug.

"You excited?" Kate asked, full of energy.

"I guess? More worried about what you're gonna do to me," Ryan admitted.

"Oh! Don't be worried! I haven't led you wrong yet have I?" Kate said with a wink. "Here let's check out those photos Chris sent," Kate said pulling out her phone. They went through the photos and then Kate pulled out some pictures of her in the same outfit. "Okay, so what do you like about yours picture and what do you wish you had?"

Ryan studied the pictures. "Um I like my ass," he said blushing. "And my waist, it's so flat and skinny looking. And my legs! Looks how long they are..."

"Mmmmm, yeah I'd love to have them wrapped around me," Kate said happy Ryan was getting into it.

Ryan blushed at his sister's obvious sexual interest, still not used to a beautiful woman expressing interest, much less his own sister. "I wish my makeup was better," Ryan said studying his pictures.

"Pah, don't we all," Kate agreed. "That'll get better with practice. What else?"

He turned and looked at Kate's pictures. "Um, I like your belly button piercing. And jewelry too. The clip-ons are so meh. Oh and your hair! Mine looks like a stupid emo teenager's. And I wish I had boobs like you!"

"Hahaha, well you kinda were a stupid emo teenager," Kate agreed. "Well thankfully we can address some of that, just not the boobs. So let's get ready!"

"Um, I am ready?"

"No silly, you want to go to a women's hair salon as a boy?"

"Oh, I guess not," he answered. Plus he could use this as a chance to get some makeup training from Kate! Kate pointed at an outfit on her dresser and Ryan quickly stripped his clothes off.

"I see you've been keeping up with your shaving," Kate said, stroking his smooth legs and fondling his balls.

"It gets itchy!" Ryan insisted.

"Hm, and I think you like it," Kate said, stroking his cock slowly and staring into his eyes. "You like your slutty sister playing with your cute dick?"

"Oh yes!" Ryan cried, before Kate backed away laughing.

Ryan pouted, then turned to the outfit. It was a small pair of leggings and a soft looking scoop neck t-shirt just like Kate was wearing. "No panties?" Ryan asked.

"Oh, pick whatever you want," Kate said gesturing at her dresser, curious to see what he would choose. Ryan made his way over and began digging through the dresser, eventually pulling out a dark red high waisted thong and slipping it on.

"This okay?" he asked Kate, turning his ass to her. Kate promptly spanked him a few times, laughing as he shook his butt at her.

"Hey, can I ask you a question?" Kate said seriously as Ryan got dressed.

"Yeah? That is a question?" Ryan replied.

"Oh shut it!" Kate said laughing. "Do you like dressing up as Riley?"

"Oh, um, yes..." Ryan admitted. "It's... hard to explain, but it feels liberating. I feel nervous beforehand, but once I am in the clothes I feel... at home?"

"Ah good! One more. Do you think of yourself as a boy still? Just in girls clothes?"

Ryan blushed at this. "Um, no... When I dress up I think of myself as Riley. Girl pronouns and all..."

"Oh, okay. Just wondering. I met one of Chris's friends and she and I had a good talk. Do you think you might want to be a girl? Like full time?" Kate asked, trying to sound casual.

"Uh, I don't know," Ryan said, sitting next to Kate.

"It's okay! I know this is probably all confusing."

"I've thought about it. Maybe? I'm just trying to live more in the moment, not think or plan the future too much for once," Ryan said.

"Oh that sounds like a good outlook!" Kate said. "Well Riley, let's go get some girly moments!"

*****

Riley turned to her sister, concerned. "Are you sure you want to cut your hair too?"

"Yeah, I've been wanting a pixie for a while and now we can be twins!" Kate said excitedly. "Oh how about this one?!" she pointed at a front, side, and back view in the style guide. The model had similar black hair and also looked half-asian. Her hair was just at ear length, and styled into a very trendy and cute style with texture.

"We can do something similar," the stylist said. "I think it will look good on both of you, but Riley's hair is a bit too short for the full style. We can get close though!"

Two hours later the girls left the salon, with matching haircuts. The stylist had been so pleased she had posted their before and after pictures to social media and Riley had never felt sexier. Kate checked her watch. "Only five! Want to get some piercings? There's a good place right up the street," Kate said hopefully.

"Oh, I don't know," Riley said. This would be a more permanent change. "Maybe we could just take a look?"

"Okay!" Kate said leading the way. They entered the piercing and tattoo parlor. Riley had never been in here and was curious to see all the designs. On the wall were photos of clients. His eyes were drawn to a woman, naked but with her privates covered sporting a colorful phoenix on her hip, abdomen, and side.

"You like that one?" a man asked stepping up beside her. "I did that, took three sessions. I can do a similar one if you want."

"Oh, I don't know," Riley said. "Maybe someday."

"Sorry, she's really shy," Kate said joining them. "We'll be back for tattoos, but today we're here for piercings."

The guy smiled at Kate, noticing her already pierced ears and figuring he was in for a treat. "Body...?"

"Ears and belly. For her," Kate said pointing at her sister. "Can you match mine?" Kate had two piercing in each ear and the belly button. The man inspected her then shrugged.

"Easy! Forty bucks per hole plus jewelry. I'll go get the gun ready while you pick out some pieces."

Riley's eyes widened. "What, That's gonna be over two hundred! I can't afford that!"

Kate rolled her eyes. "You've got a lot to learn about being a girl," she advised. "Let's just pick out the jewelry."

Riley lost herself in the selection, eventually picking out some studs and small rings adorned with blue glue gemstones. For the belly button piercing she found the exact one Kate was wearing, a dangly bit flashing with gems. The guy soon came back and rang up the total. "That'll be three twenty two," he said.

Kate leaned forward to read his nametag. "Well Trevor, we were hoping we could work out a discount," she said smiling at him.

"I can give you the employee discount for tits," he said quickly grinning. "Fifteen percent."

"Hrm, what about a blowjob from sisters?" Kate countered with a grin, her fingers trailing up and down Riley's arm.

"What?" Riley asked at the same time Trevor said "Really?"

Kate nodded and nudged Riley who quickly nodded along.

"Fuck me," Trevor said sitting back on a stool.

"Maybe for the tattoo," Kate giggled.

"Alright, blowjob first, piercings for free. You have to pay for the jewelry, they inventory it, but I can give you the employee discount," Trevor said scarcely believing his luck. Kate smiled and nodded, handing over some cash.

Twenty minutes later Kate and Riley left the store giggling, the taste of cum in their mouths and Riley sporting some new piercings. "That was kinda disappointing," Riley confessed to her sister.

"Ha! You probably thought everyone was going to be hung like Chris and Will, right?" Kate asked laughing at Riley's blush and innocence.

"He also came like immediately!" Riley said.

"Well you would too with two hot sisters sucking your cock," Kate said tickling Riley.

The girls laughed as they headed back to campus. Kate hugged Riley outside her dorm. "I had fun today. Like a lot of fun! We should do this again sometime," Kate told her sister.

"Yes please!" Riley agreed.

"Enjoy your date tomorrow," Kate said. "Six right?"

Riley nodded then her eyes widened. "Oh no, what am I going to do about these piercing? I can't take them out! Gonna look like a weirdo."

Kate smiled. "Or you could just dress as a girl. There's a bag in your room. Just give it a thought." Kate kissed Riley on the lips, "Love you sis, have fun!"

Riley watched as she walked away then headed up to her dorm room. Chris was out, but there was a large duffel bag on her bed with a short note from Becky.

Hey Riiiiiiley ;),

Looking forward to seeing your new haircut! I guess Kate will give me a preview, but I can still act surprised! Here's some clothes for you. It's all my and Kate's stuff so it should fit nicely!

-Becky

Riley read the note again and looked through the clothes. There were probably two dozen outfits! She quickly texted Kate. Um wow! This is a lot!

We gotta make sure our favorite girl is looking good ;p she replied. You probably can't fit it all in your dresser and closet so I recommend putting your boy clothes in the bag.

I'm not gonna do that Riley replied blushing. What would Chris think when he noticed!?

One week. One week no boys clothes and I'll suck your cock. Kate attached a picture of her lips and tongue sucking one of her fingers.

Riley paused considering. On the one hand this was her sister! Who wanted a blowjob from their sister!? There was also the minor bit about having to dress like a girl for a week. This actually didn't seem that scary. Her classes were huge so no one would notice and her only friends already knew and seemed cool with it.

On the plus side, a blowjob from Kate!? Who the fuck would turn that down? The fact Kate was her sister only added to her arousal. Besides, she had already eaten Kate... Is Becky okay with that? Riley sent back after ten minutes of agonizing. Becky not being on board was her easy out.

It was her idea! She wants to watch ;P Kate replied.

Riley sighed. Okay...

Great! Swap out your wardrobe so there's no cheating!

It took Riley about half an hour to swap the clothes and she was thankful Chris was out. She got ready for bed, pulling on a comfy pair of sleep shorts and an oversized t-shirt that Riley recognized as one of Will's. Slipping into bed, Riley soon fell asleep, her mind surprisingly at ease about the coming week.

*****

Riley stood at the bathroom mirror putting the finishing touches on her makeup and hair, pleased with the results. She was starting to get a hang of the everyday look. Suddenly there was a pounding on the door.

"Ryan dude, you've been in there forever, I have to shower before class," Chris called. Without thinking Riley opened the door.

"Sure, I'm done," she said as Chris's jaw drop. Riley realized she was standing there in only the tiny pair of boyshorts she had picked out for the day. "Ack!" She cried, trying to cover herself.

Chris just grinned at her, his dick starting to rise. "Cute panties Riley!" Riley blushed and walked past him, doing her best to act normal but aware of his eyes following her tight butt as she entered the room, pulling on a short green dress and thin tights. She completed the outfit with a pair of ankle-high boots with a small heel.

In typical fashion, Chris's shower was short and he strode back into the room towling himself off and not bothering to hide his erection. He winked as he caught Riley staring. "Wish we had time for you to take care of this before class," he casually said as he slipped on some jeans and a t-shirt.

"Y-yeah," Riley stammered, realizing she was eager as well. "Maybe this afternoon after classes?"

"Maybe. What time is your date? I'm meeting up to play some soccer, probably won't be back until seven or so," he said grabbing his bag.

"Damn, six..." Riley said feeling disappointed. Chris's bulge was prominent in the tight jeans and she couldn't seem to drag her eyes away.

"Ha well maybe later then if I strike out," Chris laughed, taking in Riley's clear admiration. He reached out and helped her off her bed. "Ready?" The two headed off to their classes. They walked across campus, Chris being sure to maintain some physical contact with Riley, even cupping her ass on occasion.

As they neared Chris's building he pulled her to the side of the path under a tree, placing her hand on his still hard cock. "Fuck Riley, see what you do to me?" Riley shyly nodded, softly stroking him. "Answer me," he commanded tilting her chin up to look at him.

"Yes, I see," Riley whispered, worried her own erection was going to show as well.

"Hmmm, so your sister calls me daddy, your girlfriend calls me daddy. Let's try that again," Chris instructed, sliding a hand down to gently grasp her neck.

"Oh god! Yes daddy! I see what you need from me," Riley panted. She realized if Chris forced her to her knees right here in the quad she would eagerly suck his cock.

"Good girl," Chris said leaning into kiss her. "See you after your date," he said with a wink as he strode off. Riley leaned back against the tree and breathed deeply, wondering how the hell Chris had turned into a simmering needy slut so easily. After several minutes she gathered herself and scurried off to class.

The day passed easily, with nobody noticing that one of their classmates had changed from a boy to a girl. Riley was surprised when people, guys and girls, started up conversations with her and seemed interested in actually talking with her.

In an afternoon class several boys had gathered around her flirting, one even asking her out. She had played it off laughingly revealing she was interested in someone else. Everything seemed cool until it came out it was another girl and suddenly every guy was insisting on getting her number. Overwhelmed, she didn't know how to say no and ended up giving her number out to the three friends, planning to just ghost them.

"So how was your first day!?" Kate asked excitedly as her sister walked up. Riley grinned happily in answer and Kate wrapped her in a hug.

"Thank you so much Kate!" Riley said as they started walking to her dorm. "Honestly one of the best and easiest days of my life!"

"Did anyone hit on you?" Kate asked eagerly.

"Um, kinda?" Riley said. "Some boys kept asking me for my number! I kept trying to play them off, but after they found out I was dating another girl they just wouldn't stop! I ended up giving in just to get them to shut up so I could hear the professor!"

"Ha! Welcome to a girl's life," Kate said. "You should be careful with that. I can give you some fake numbers that you should memorize. What about Chris though? He texted saying you were looking hot!" Kate pulled out his phone and showed a picture Chris had snuck in class of his hard dick sticking out of his open jeans.

"Oh yeah!" Riley blushed. "Uh, I may have promised him a blow job tonight after my date with Becky... I hope you're not mad." Riley was nervous how her sister would react since she and Chris were going to date as well.

Kate giggled happily though and bumped their hips together. "OOooo, I'm so proud of you Riley! Just so you know Becky and I are cool with sharing. We've talked and at this stage being open and experiencing new things is more important than finding 'the one,' right?"

"Yeah, I think so," Riley agreed, happy Becky and Kate were okay with her fooling around some. Thinking about it she wasn't surprised given the activities of this past weekend.

"Good! Now be sure you follow up on that promise to Chris, he's not the kind of man you can cock tease and expect to go unpunished!" Kate advised her younger sister. "Any thought on the outfit for tonight?"

"Um, I'm not sure," Riley said. "It's getting a bit chilly so I was thinking maybe jeans?"

"Screw that!" Kate said. "You're gonna have to learn how to sacrifice comfort for beauty as a girl. On a night like this I'd maybe aim for a dress, pantyhose, and a cardigan."

"Oh, okay," Riley agreed, deciding she should follow her sister's advice.

In her dorm, Riley showered while Kate got an outfit together. The two happily talked and joked as Riley applied makeup with guidance from Kate. Having her there to provide real time feedback was so much more helpful than videos online and Riley felt like her eyeliner came out looking okay for the first time doing it herself.

As six approached Riley got dressed, slipping on a small pair of bikini panties that rode into her crack, pantyhose, and a small dress that fell to just below her crotch and had a keyhole cutout revealing her abdomen. The bottom was loose and as she walked or turned the hem shook revealing her bright pink panties. On top she had threw a small cardigan for warmth.

"Fuck you look good," Kate said as Riley modelled the outfit. "Honestly you're kinda lucky to be starting out life as a girl now and not having to go through growing up as one."

"Huh, not like my life was great," Riley said as she looked down at her chest and frowned. "This would look better with boobs," she complained.

"Ha! True, but nothing we can do now," Kate said. "Come on, let's walk over to my place. Becky is probably ready." As Riley gathered up her purse and slid on some some small heels, Kate hefted up the duffle bag containing her boy clothes.

"Uh, what are you doing with that?" Riley asked concerned.

"Look, I really really want to suck your cock next weekend. Like I've already had Becky eat me out several times thinking about that. So I just want to make sure you make it a week," Kate explained.

"Oh, well I guess that's okay then! Thanks sis!" Riley hugged Kate, nearly toppling the tiny girl holding a heavy bag over.

"Hey watch it! Hard to suck dick well if you break me," Kate said laughing as she caught her balance.

"Sorry sorry!" Riley said, brushing her off. The two headed to Kate's dorm. When they entered Becky was putting her shoes on.

"Oh my god Riley!" Becky dropped the remaining shoe and awkwardly ran to hug Riley. "You look incredible! Wow!"

"Thanks! Kate helped!" Riley said her heart and head spinning with happiness.

"Oh don't listen to her, I picked out the outfit, but she did one hundred percent of the hair and makeup!" Kate said as she tossed the giant clothing bag into the corner.

"Well I'm honestly impressed, you look so good," Becky said staring into Riley's eyes. Riley felt so warm and the old Ryan would have squirmed away from the attention. Instead she decided to embrace it.

"Glad you like it! Do you like the piercings?" Riley pointed at her ears and belly.

"MMMmm, so sexy, just like that tasty sister of yours," Becky said, her voice filled with lust. Riley looked at Becky, impressed with her outfit. She had on a body hugging bodycon dress that fell to her ankles. A slit up one leg revealed bare skin all the way to the top of her hip, and cleavage was clearly enhanced by a push up bra.