This one's the first in a series of stories about Simon and his naughty sister Kelly. See, she thinks anal sex is gross. Butt stuff in general, who needs it? Simon on the other hand, he's a genuine ass man. Does it make him a little uncomfortable when he sees his sis in her yoga pants? Sure, but he's a gentleman. Things get a little more uncomfortable when Kelly brings up the topic of anal play. Her boyfriend wants them to go for it but she doesn't think she's ready. She wants Simon to explain it to her. And then...she wants him to show her! Kelly won't stop teasing Simon until she gets her way, and when she does, it changes their relationship forever.
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It was almost an hour before Kelly texted me. She wanted to shower after she did her business in the bathroom, and shave, and then she wanted to inspect every crevice and cranny and ensure her downstairs was trim and tidy and smelling like flowers.
Not that I didn't appreciate it, but while Kelly was primping I was downstairs watching the minutes tick by in slow motion. I almost had a heart attack when my phone buzzed. A single word appeared on my screen, "Ready," with a smiley face beside it.
She was waiting for me by her bed. The room was still humid from her shower and fragrant as a jungle garden. Maybe that's why the air around her body seemed to sparkle. Gone was the hoodie and the yoga pants, replaced by a half-naked angel. Her skin was freshly exfoliated, her hair slightly damp and curling down her shoulders. Her skimpy undershirt cut off just above her bellybutton and her wet nipples blazed through the cotton. The lips of her shaved pussy were visible through her lacy hipster panties.
"Hey," she said.
"Hey," I said.
She tugged at a lock of hair. "Still drunk?"
"...sure," I breathed.
"Yeah," she said. "Me too."
Three colorful condom packets were piled at the edge of the bed. They clashed with her smooth white comforter just like her coral nipples clashed with the t-shirt. My eyes trailed from their stiff tips to the line of her panties. She chose them for a reason. The form-fitting cut of the legs complemented the swell of her luscious buttocks.
The door to my sister's closet was a sliding mirror (my reason for choosing her room over mine), which put us face to face with our reflections. There we were, brother and sister, standing by her bed. "Sh-should we face the other way?" she asked.
"Bend over," I said.
She jumped at the command. "Wow, so we're just--"
"Bend over," I repeated. That's right, I thought, big brother's in control.
Kelly complied immediately. The soft sound of her nails sliding over her comforter filled my ears as I stepped behind her. "I'm going to pull your panties down," I said. "Is that okay?"
Her butt shivered at my touch. "N-no, go ahead," she whispered.
"Don't look down," I said. "I want you to watch me."
"Okay..." She rested her elbows on the mattress as I went to work.
I could feel her anxiety beneath her skin, raw and electric. I rubbed my palms down the backs of her thighs and watched her expression shift in the mirror. It was weird that her brother was touching her this way...but it felt good to be touched. I slid the panties down her shapely thighs and guided them to her ankles. She giggled as I caressed her toes. "Up," I commanded, and she obeyed. The panties skated over one foot, then the other, and then my sister was truly naked--for everything south of the bellybutton.
On my knees, I regarded my sister's juicy butt. Each cheek was so round and full that I had the compulsive urge to spank her. I also had the urge to spread her open and admire the pink of her freshly shaved pussy. "Stay focused," I muttered.
"What?" she said.
"If we were doing this the right way we'd introduce a little anal play every night," I said. "Your butt isn't used to being touched and it's going to be super sensitive."
"Oh," she said. It was awkward for her to talk to me over her shoulder so instead she faced the mirror. As our eyes locked we were once again confronted with the weird intimacy of this moment. Her wet hair framed her giddy face. "How's the view from back there?" she asked.
"Good," I murmured. "You have a great ass."
She blushed. "Thank you."
I squirted a quarter-sized dollop of KY into my palm. "This is going to feel really weird."
"Ew," she said. Her eyes followed my glistening palm as it slid into the crack of her ass. She squeaked when I slathered the stuff against her puckered anus. It was tiny and pink and tight as a drum. I had my doubts that anything would fit in there today. Still, Kelly needed an anal lesson and I promised to teach one. I began to gently massage the KY around her tense asshole.
Kelly bit her lip. "Mmm. That's...not so bad."