Sheltering My Runaway Sister

"Ok," she said and grabbed a few pairs like that with different sizes. "Cute and comfortable is good."

She bit her lip and glanced away from me and asked, "But what if I want to be more than cute? What would you think is sexy?"

I cleared my throat and looked around. The woman customer had paid and was leaving. The employee had picked up her phone and was very clearly ignoring us.

"Well," I said. "These can be sexy, if you have a good body. They should look good on you." I picked up a pair of boy shorts. Then I pointed at some thongs. "Those are more ...obviously sexy."

Bailey grabbed several of both styles. Then crossed to bras.

"I won't be much help here," I said. "You should make sure to get ones that fit you properly. I bet the chick who works here would be able to help with that."

"I don't want her help," Bailey said. "You can help. I'll try on a few and we can figure it out together. I think I'm a double D. I'll grab some around that size and we'll make do. I'll need to try on these panties too."

We headed towards the fitting room at the back of the store. It was around a bit of a corner and there were three empty booths. Bailey popped into one and I sat on the bench outside.

It was a few minutes later when she opened the door and stood there smiling at me.

"What do you think," she asked.

It was, honestly, difficult to think at all.

She had shed her shorts and t-shirt and was wearing one of the simpler sets of panties that I had pointed out first and a simple bra. The effect however was amazing. Her legs were long and smooth, her stomach soft but not flabby. The bra supported her full breasts, pushing them together. The dusting of freckles across the tops of them looked very cute.

"You look great," I managed to say. "How ...how do they fit?"

She slowly turned around in front of me. I saw how the panties cupped her ass. The smooth pale skin of her back. She did not seem to be awkward or self conscious at all, though there seemed to be a bit of a flush on her cheeks and upper chest.

"I think I got the panties size right," she said. "And I think the cup size is good. Not too tight, not loose. But I'm not sure about the strap. This is a 36 DD. Maybe a 34? Look."

She stepped towards me and I glanced into the store. There was no one and I could not even see the cashier. My eyes returned to my half-sister.

She leaned forward in front of me, and I saw how the cups fell away from her breasts a bit. Looking into that space between flesh and fabric I could just make out the edge of something pink. Her nipple.

I was becoming painfully aware of my cock swelling in my jeans and was happy that I was sitting down, able to hide my arousal.

"Yeah," I said, my voice a bit hoarse. "Maybe a bit loose."

"That's ok," she said. "I also grabbed some 34's. Ok. Next set!"

She went back into the room. And I took a deep breath. I needed to get ahold of myself. Having this 19 year old woman modeling for me was amazing, but she was my sister and I had promised to take care of her. I was not doing a good job of that at the moment.

The door opened again and it felt like my breath was taken away. She was wearing a white thong that was cut narrow in the front and high on the hips. Her untrimmed auburn pubic hair escaped the edges of the white panties. The bra was also white, but perfectly sheer. I could see her pink nipples through the fabric, and the wide areolas that surrounded them.

"Wow," was all I managed to say.

"Yeah. This bra fits better. 34 DD. Now I know."

She looked down at herself and ran her fingers over the escaped hair below.

"This doesn't look good though," she said, frowning. "Maybe these aren't a good style for me."

"You could always shave or wax," I managed to say.

She looked up at me and smiled.

"Yeah?" She asked. "When I watched those videos it looked like most of the girls did that. Is that what you like? Are the girls you go with shaved?"

I cleared my throat, a bit uncomfortable.

"Some," I said. "Some shave or wax. Some just trim. Some leave it natural. It's all ...fine. Whatever they feel good about."

"Some," she said laughing. "How many girls do you sleep with, Brent?"

I shrugged.

"I'm single, but there are a few. And I'm old so there have been plenty over the years."

"But what do you prefer?" She asked. "If you had it your way, how would women do it?"

I shrugged again.

"Shaved and waxed, I guess," I said. "I think I'm not alone in that."

She nodded to herself.

"Ok. Shaved it is," she said. "Thanks for the advice. I guess I'll google how to do it. I guess based on this I know what size I am. I'll just grab some stuff that fits and we can head home?"

I nodded and she went back into the booth. I adjusted my hard cock so it was trapped in the waistband of my boxer briefs and was standing when she emerged.

We went to the counter and paid the bored girl working there and headed back to my truck. The purchases at the lingerie store, ironically enough, were the most expensive of the day, but I did not mind. Bailey seemed to be in a good mood.

We were driving back home when my phone rang. It was from Ash, my assistant at work. She knew I was off today so thought that something important might have come up. I pressed the button on the steering wheel to answer and said hello.

Ash had been my assistant and functional office manager for a couple of years. She was incredibly organized, efficient and pleasant to have around the office. I had no idea if I could run my business without her.

We had also been having casual sex for over a year. She was engaged and loved her partner but the chemistry between us was too strong to deny, and we managed to keep things fun, and not serious. I was enjoying the situation while it lasted.

"Hey babe," Ash said. "How's your day off? Are we still on for tomorrow night?"

I quickly realized that her voice was filling the cab of the truck and cut in.

"Good," I said. "The day is good. I just took my sister shopping at the mall. She's here with me in the truck right now. Sa hi, Bailey. Meet Ash."

"Hi Ash," Bailey said. "Nice to meet you."

"Nice to meet you too," Ash said, her tone switching from flirty to more professional.

"Brent," she said. "Did you ever tell me that I had a sister? I think I would have remembered that."

"Probably not," I admitted. "Our situation is ...complicated. She's from my dad's second marriage so she's a fair bit younger and I haven't known her well. She's staying with me for a bit while she figures some stuff out."

"Oh," Ash said. "That's nice for you guys. It's good to catch up."

"In fact," I added, "I know you've been looking for help around the office since Stacy left us. I was going to start Bailey on Monday. You think that would work?"

"Don't worry," Bailey cut in. "I won't be some nepotism loser! I'll work really hard and do a good job!"

Ash laughed.

"Ok," she said. "I can make that work and I do need the help. Welcome to the team, Bailey."

I smiled over at my sister and she smiled back.

"So Brent," Ash said. "About our ...meeting tomorrow night. Are we going to have to reschedule?"

The next night was a Friday and Ash's fiancé was out of town. We had planned on going out for dinner and then going back to my place after.

I looked over at Bailey.

"I don't know," I admitted. "This has all been a bit of a whirlwind."

"You don't have to worry about me. I can take care of myself tomorrow night," Bailey said.

"Ok," I said. "Then we are still on, Ash. I'll see you at work tomorrow and we can nail down the details."

"Sounds good," Ash said. "I'll see you tomorrow. Nice to meet you, Bailey."

"You too," Bailey said and I hung up the phone.

+++++

We stopped at a grocery store and picked up some food so that we didn't have to order in every night, then arrived home.

Ash insisted on cooking and made pasta and a salad while I sat in the living room and watched some tv. The food was good and hanging out with Bailey was pleasant. After we cleaned up she headed to her room and I relaxed with a book for a while.

It was later that night, around 11 when I was thinking of getting ready for bed when she came into the living room. She was wearing my flannel shirt again, and did not seem to be wearing any shorts as I could see almost the full length of her legs before they disappeared under the shirt.

"Hey Brent," she said, stepping in front of me. "I wanted to get your opinion on something."

"Sure," I said, dropping my bookmark into the book and closing it.

Baile gripped the hem of the button up shirt and lifted. She was wearing one of the thongs that she had picked out, this pair made of sheer black fabric. She had clearly shaved, since the hair that peeked out the other pair earlier was not there. I could see her puffy pussy lips through the fabric, a bare slit.

"Does this look better," she asked, looking at me biting her lower lip. "I did my best."

My hands were clammy with sweat, as I looked at my sister. I had to clear my throat before I could speak.

"It looks ...great," I said.

"Does it look ...sexy?" she asked.

"Yes," I admitted.

"I'm worried I missed some. You didn't have a good mirror to check," she said and stepped closer. She hooked her finger into the side of the panties and pulled it, revealing her bare pussy to me. She leaned back a bit, pushing her hips forward. Her voice was hoarse when she asked, "Can you check?"

It was wrong. So very wrong on every level. I should have stood up and left the room but I did not. The sight of my sister, presenting herself to me, the rush of blood to my cock, all prevented me from making the correct decision.

I leaned forward, moving my face closer to her bare pussy. It was red, from the shaving, and smelled fresh and clean. I could catch the scent of a woman's shaving cream, floral, but under that, the unmistakable smell of a woman's sex.

I could see no stubble or stray hairs.

"I think you did a good job," I said.

"Good," she said, sounding relieved. Her fingers parted the lips, revealing the pink inner lips and her clit. I could see a string of wetness connecting one side of her lips with the other. "I thought I felt some stubble when I touched there. Can you check? Feel for some?"

As if of its own accord my hand raised. I could see a tremor in my fingers and they led the way. Bailey gasped and jumped when my fingertips brushed the outer lips of her pussy.

The smooth skin gave a bit under my fingertips. I ran them along the edge of her pussy lips and glanced up at Bailey's face. Her lips were slightly parted, and she was looking back at me with half closed eyes. She pushed her hips forward, pressing harder against my hand.

"Seems pretty smooth to me," I said, my voice almost a whisper.

I ran my fingertips back along the edge of her lips, and heard her moan above me.

"Did you get the inner edge," I asked.

"Can you check," she asked,her own voice breathless. "Please?"

My fingers pushed between the lips and Bailey moaned above me. I ran them lightly along the inner lip on the left side from back to front. Slowly gliding them along, moving easily due to her wetness. When I reached the front I slid my fingertips to the other side, grazing her clit. She moaned again.

I slid them back on the other side. She was so wet it would have been easy to push my fingers into her. I knew that she would not stop me. I wanted to but refrained myself.

"Seems like you did a good job," I said and was about to take my hand away when her own clamped down on it, keeping it in place. Pressing it against her.

Her hips bucked and she groaned, before crying out. I felt a flood of wetness drip down my hand as she came on it. She froze in place, gasping, legs locked for a few moments before she released my hand.

"Thank you for your help," she said, stepping away quickly. "I'm going to bed."

She spun and hurried up the stairs. I let myself sink back into my chair. Amazed by what had just happened.

I knew that it was insane. That I should not have done that just then. That I was not doing a good job of protecting her like I had promised to do.

My thoughts however focused on how she had just cum from that light touch. What would have happened if I had pushed my fingers into her? If I had pulled her down and fucked her? How hard would she have cum then?

I shook my head and went up to my room, jerking off to images of my sister once more.

+++++

Bailey was still in bed when I left for work the next day. I left her a note saying I would be back late and a hundred dollars in cash if she wanted to go out while I was gone.

I had mixed feelings about the night before. My sister obviously had some fucked up issues, but I seemed to be no better. It had been like I had no control over myself. I resolved not to confront her about it, but also to behave myself better in the future.

It was a busy day but it passed quickly. I received a text in the early afternoon from Bailey.

what am I supposed to do with this much cash lol have fun on your date tonight

I smiled and texted back.

whatever you want as long as it's legal or you won't get caught at least. See you late or tomorrow.

Ash and I had reservations at a decent Italian restaurant and we showed up separately at around 7pm. It was a place we had eaten at together often.

Ash arrived a bit after me, seeing me sitting at the bar sipping a beer. I had to smile, seeing her. She was 27 years old, still young and beautiful. She had curly dark hair that fell past her shoulders and mocha skin, the result of a black father and white mother. She was wearing a black dress with thin straps that showed off her figure.Her breasts were larger than Bailey's I judged, but Ash had a fuller figure, all curves. Her ass was full and her hips wide.

We had been fuck buddies for a while now. She loved her fiancé but told me I gave her something she couldn't get from him. He sounded like a really nice guy but very vanilla and boring in bed.

I had felt bad at first, but Ash had no regrets so I followed her lead. It seemed like she was able to keep this going with no one getting hurt and it suited my lifestyle. I had never wanted to settle down, but I loved sex.

Ash walked up and kissed me, our tongues dancing together briefly.

"Hey you," I said.

"Hey yourself."

We got a table and ordered food and chatted. We talked about work for a bit, getting a few things out of the way that we could deal with on Monday then she asked me about Bailey.

I gave her the rundown about my dad and his new family and Bailey running away. I skipped all of the inappropriate bits, the spanking, the shaving and inspection. How my sister had cum against my fingers twice in three days.

"You are doing a good thing, Brent," Ash said when I had finished.

"I hope so," I said. "I don't know what I'm doing. I just want her to have a chance, you know?"

"You are. I was lucky that my mom was great but there were times when I wished I had a man to take care of me and guide me when I was younger. My dad wasn't around much."

She ate some ravioli.

"What does she look like? You?" Ash asked.

"I don't know," I said. "I guess not. Her hair is like, red? Brown? Auburn I guess?"

"Is she pretty?"

I shrugged.

"I guess so?"

Ash laughed.

"So she's pretty. It's fine. You can say it. It would be surprising if you didn't notice. Unlikely."

"Ok," I admitted. "She is quite pretty. Very young though."

"Must be hard having a pretty young thing in your house, after living alone for so long," she said, an edge of flirt entering her voice.

I almost jumped when I felt something move up the inside of my thigh. I looked into my lap and saw Ash's bare foot. She had slipped off her heels it seemed.

"She is my sister," I said.

Ash's foot pressed against my cock which was coming to life there in the restaurant. I scooted my chair forward so my stomach hit the edge of the table, letting it and the tablecloth hide what she was doing.

"So?" Ash said. "That doesn't mean that she isn't a woman. And that you aren't a man. I know you are a man. Very well."

As she spoke she rubbed her foot against my cock, pressing it against my leg and slowly gliding along it with her foot. Generally, I was not a foot person but this, in this setting, was undeniably hot.

"Still," I said. "There are lines not to cross, right?"

Ash smiled.

"Well," she said, "as a woman who loves to call you daddy as you fuck the shit out of me, maybe my lines are a bit different. Nothing wrong with a bit of fantasy, is there?"

My cock was throbbing and after being around Bailey for a few days I needed to be inside someone.

"Are you ready to go?" I asked. "Still want to come over?"

"Baby," Ash said, "I'm fucking dripping over here. Yes I want to come over."

I paid the bill and we both drove to my place in seperate cars.

We were barely in the door before Ash's arms were around my neck, kissing me. I held her tight to me, enjoying the feeling of her pressed against my chest. My hands drifted down to her full ass and squeezed the cheeks.

"Let's get up to my room," I said, taking her by the hand and leading her upstairs. I saw that the door to Bailey's room was closed and was happy to see that.

Once in my bedroom I swung the door shut behind me. I noticed that it had not quite latched, staying open a few inches but was distracted from fixing that by Ash dropping to her knees in front of me. She shrugged the straps off of her shoulders and the top of her dress fell down, revealing her large, full l, light brown breasts. Her nipples were a darker shade and stood out, lick thick bullets.

She reached forward and grabbed my belt, undoing it, then opening my jeans and pushing those off my hips. My cock made a tent in my black boxer briefs right in front of her face. She had a hungry look on her pretty face as she yanked those down as well.

My cock sprang free. It was about 7.5 inches long and quite thick. It had a twisty purple vein along the top and was uncut. The swollen head was half out of the sheath of skin, glistening at the end with precum.

"Fuck this is a good cock," Ash said, gripping the shaft in her hand. "Will you fuck my face, daddy?" She asked, then placed the head in her mouth.

"Yes, baby," I said and thrust, shoving my cock deep, hitting her throat.

I knew what she liked and obliged, burying my hands in her hair and thrusting my hips. I fucked her face hard and fast, while she had her own hands up her skirt, rubbing herself.

The glug glug sounds of her face fucking filled the room. Occasionally I'd shove deep into her throat and hold her there cock cutting off her air while her eyes watered looking up at me. When she tapped my hips with her hands I'd pull back giving her a short gasp of breath before starting again.

I was very worked up and had to stop after a few minutes, not wanting to cum too soon. I pulled out of her mouth and stepped back.

"Get on the bed," I demanded. "I want to taste you."

Ash quickly did as she was told and flopped onto her back on my bed, legs splayed open. I moved and kneeled at the edge of the bed and reached under her dress, feeling a flimsy pair of panties. I gripped them and yanked, tearing them off of her.

She yelped but laughed then moaned as I shoved her legs apart and drove my mouth to her pussy.

Ashe always tasted amazing. Sweet and salty with a hint of spice. I licked along her slinken canal between her shaved pussy lips, from her opening to her clit which I sucked into my mouth.

I pushed two fingers into her and used them to fuck her as I alternated between licking and sucking, focusing on her clit.

Ash moaned and writhed under my mouth. I grabbed her thigh with my free hand and held her in place.