“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.
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