Bad Halloween HabitsbyFflow©
I had worked on my costume for weeks, carefully planning every part of it. I had shaved exactly three days before to insure that I had just the right amount of stubble on my face. I'd unearthed my old work boots, purchased a rosary and cross, and had constructed an almost perfect replica of a nun's habit. I had even borrowed one of my mother's D-Cup bra's to 'round out' the whole look. My philosophy has always been that, if you're going to dress in drag on Halloween, you might as well dress as a nun.
As I was putting the finishing touches on my costume, Cindy, my kid sister came into my room.
"I don't know if you heard, but Julie got busted with some hash, so her parents cancelled her party... I've got nowhere to go", she said, coming up behind me as I struggled to shove the last few tissues into my bra. She smoothed the heavy black cloth so it lay nicely across my broad shoulders.
"Gosh, Greg... That outfit looks pretty good on you," she sighed.
"Cindy, thanks for the complement, but I've got to get going," I muttered, pushing her aside as I moved around my room looking for my wooden ruler.
"Are you looking for this," she asked playfully, holding the ruler out so I could take it from her.
"Yes! That's exactly it! Thanks!" I grabbed it from her, and brushed past her, heading for the door.
"Hey, bro! If you wait just a few moments I think I have the perfect costume to complement yours... Maybe we can go to your party together...." I looked at my watch and, realizing that I was already late, said, "Sure... Just hurry up, ok?"
Since my sister had turned 18 she had really changed, and for the better. She wasn't such a pain in the ass, like she used to be when she was a bratty kid. I actually enjoyed spending time with her. Also, as she had grown, she really developed into a complete babe, and I was constantly chasing my horny friends away from her.
"Ok! I'm ready," she yelled as she waltzed into the room. I nearly fell over when I saw her... First, she had put her thick black hair into two fat ponytails, one on either side of her head. She'd found some goofy black plastic glasses that gave her almond-shaped brown eyes a nerd look. She wore a white cotton short sleeve button down collared shirt that was tucked neatly into a knee high pleated plaid skirt and, to complete the uniform, white ankle socks and penny loafers. She was dressed like a Catholic schoolgirl... A really hot, well-developed, and sexy schoolgirl. She did a quick spin and, as she did, her skirt flipped up, revealing sexy red satin panties.
"What do you think, Sister?" she asked, smiling. I tried to assume an authoritative air, circling her slowly and adjusting her shirt collar. I moved behind her and she stood very still, waiting for my approval.
"What kind of panties are you wearing, little girl?"
"Red satin panties, Sister," she replied, sweetly.
"You know only white cotton panties are allowed in school, don't you?"
"Yes, Sister, but all my other panties were dirty!"
"Well, you can't wear these," I shouted. "Take them off!"
You have to understand that, up until this point, I was just goofing with my kid sister. I didn't have a sexual thought in my head... Sure... She's a total fox and all but she's my kid sister! Anyway, when I told her to take them off I was sure she'd just laugh and we'd go to the party, but she surprised me...
"Ok," she said softly. Right then and there, without hesitation, she slipped her hands under her skirt and slid her panties right down and stepped out of them. Standing up again, she held them out to me. I took them and could still feel her warmth in the material. She was still facing away from me so I held them up to my nose and took a deep whiff. Wow! I could smell the sweet, delicate scent of her pussy on the satin.
"I've been bad," she said, almost in a whisper. "I've worn naughty panties and thought naughty thoughts. I should be punished." I looked down and saw that I had her warm panties in one hand and the heavy wooden ruler in the other.
"Bend over," I ordered harshly, "and hold your skirt up! You're really going to get it now!" She complied, revealing the smooth, pale cheeks of her muscular, teen-age ass. As she bent even further, I could see the outer lips of her pussy and a trim black bush above it. "You've been very bad," I screamed, "and now you have to take your punishment!" I pulled back and swung the ruler down hard on her upturned ass cheeks. The smack was so loud that I think it surprised us both. She let out a scream, but didn't move one inch.
I took another, more measured, swing and the tight skin began to turn pink. My strokes became more frequent, more even, and her once pale ass turned bright red. All at once I realized that my cock was rock hard and throbbing under my Nun's robes. All of a sudden I realized that this was my sister whose ass I was tanning, and not some college co-ed. I stopped and backed away, somewhat mortified. Cindy, though, wasn't finished with our little game.
"Sister, can we sit a moment and talk about my sin?" Before I could answer, she pushed me back toward a simple dining room chair with no arms. I sat suddenly. Cindy straddled me, facing me as she pressed her hot, naked ass into my still throbbing crotch.
"I've had naughty thoughts, Sister," she said, rubbing her bare pussy against the tented material of my habit. "I've had thoughts about my brother, Greg. I've dreamed of doing things to him... with him. Things that a brother and sister should never do!" As she spoke, she was pulling my frock up, exposing first my legs, then my briefs. She worked the material up and reached into my shorts and pulled my cock free. Cindy continued with her sinful litany, "I dream of taking his big, thick, 9 inch cock into my tender, young pussy. I imagine him opening me up, his thickness stretching me, his cock sliding deep into my tight channel." As she spoke, she rubbed my cock head up and down her moist, hot pussy lips. I could feel her juices flowing out of her and down my cock, onto the mat of curly hair at its base.
I pulled the cowl off my head and then held her face in my hands. "Cindy, its me, Greg! We shouldn't be doing this!"
She looked right into my eyes and said, "I know," as she slid her pussy down over my throbbing cock, forever sealing our fate as siblings, and as lovers. Her eyelids fluttered as she pressed down against my pubic bone and ground her slick cunt against it. She tilted her head back and moaned. I began unbuttoning her shirt and, exposing her tender breasts, tonguing them. All of a sudden her whole body went stiff and a loud cry flew from her throat. "Oh MY GOD I'M CUMMING!!!" She shook, quivered, and quaked from head to toe, her whole body clenched in the throws of a powerful orgasm. I held her tight, waiting for her to ride that crest to its finish. Eventually, she opened her eyes and gazed at me with a wild mixture of love, lust, and something else that almost looked like greed. "I've got another fantasy," she said, still somewhat breathless. She lifted herself off of me, turned facing away from me, and sat down on my lap again. My cock, still hard, ached for release. She slid it, slippery from her juices, along her ass crack. She looked over her shoulder and asked, "Hey bro, have you ever thought about fucking your sister's virgin ass hole?" Before I could answer, she rose up and pressed the head of my cock against her tight sphincter.
I thought, for sure, that there was no way my thick cock would make it into that tiny opening, but she didn't give up. She pressed down, forcing my cock head to open her anal pathway. I ran my fingers up her back to her shoulders, and helped by pulling down on them, working myself deeper into her anus. When she couldn't take any more, she rested, breathing heavily.
I could feel her rapid pulse in her ass, the muscles throbbing with each beat of her heart. I reached around and began to caress her breasts, grasping her tender nipples in my fingers and squeezing them. One hand slid down further and found her pussy lips gaping open, wet and engorged. I gently stroked her clit and, for some reason, this roused her into action once again.
Her ass did not slacken its fist-like grip on my cock as she eased herself higher, or when she plunged down again. My breath came in short gasps as I was overcome with the feelings she was giving me. I tried to let her control her movements but, in short order, I knew I was going to cum like a banshee. At that moment I grabbed her hips and began to thrust her up and down over my exploding cock.
"OOOOOOH FUCK, CINDY, OH SIS, I'M CUMMING IN YOUR ASS!!! AAAARGH!" It felt like her ass was pulling a long rope of cum from the depth of my balls. Jolt after jolt shot up into her twitching ass, some spilling back out onto my matted pubic hair. Eventually, my cock softened and slipped out of her sore butt.
"Oh, wow, Greg, that was really hot!"
"Yeah, Cindy! You're not a kid anymore, I guess..."
"Greg... I have other fantasies too. We're going to be doing a lot more of this from now on. I just want you to know that."
"Ok, Cindy... But can I rest first?" We both fell laughing to the floor, holding each other close, and savoring the afterglow of a very special Halloween night.