Betting Your AssbyOneSilky©
A Silky Adventure
This is a stand alone story, but makes more sense if you start with Adventures of Silky #1
My name is Silky, I'm almost 21, and I live with my owner/lover/Daddy George and my sister/lover Jessica in Alabama. We all sleep together in one big bed, and life is generally sweet. We are college students. Jess is tall and blonde with blue eyes. I'm shorter, with flaming red hair (and pussy) and green eyes that match my emerald ear studs.
George loves to get professorial with us. We tolerate it because he's really smart and a good teacher, and most of the stuff he wants us to learn has value. One of those is poker. George thinks everybody should know how to play, so they can understand what calculating the odds means.
Part of that includes betting 'for real.' We never play pretend bets. George has lots more money than us, so we do hold to a limit we can afford. However, the concept of strip poker blends right on in at home, so if I'm out of money I can bet my bra, panties, etc. Jess and I usually dress like Eskimos for poker games, to fudge as far as possible on the ability to keep playing.
As everybody knows, in strip poker, somebody winds up naked. In every fantasy I've ever read about it, the naked person offers a blow job or something else when they're out of clothing. We kind of do that; if I'm naked, I can bet whatever someone else will buy
"Jessie, I'll lick your pussy for $20."
"Nah, I'll give you $10."
"Ten dollars! For cunnilingus of my quality? Any guy on the street would pay $100!"
"No guy would pay anything, it's pussy licking!"
"I gave you $30 last week!"
"Yeah, but I had two aces, and you don't."
"You don't know that!"
"Yes I do, when you've got a good hand your nipples get hard."
That's an example of how we do it; also of how Jessie can be cold and mean. Then there are the hands where you have such good cards that you know you're going to win, so you risk a lot.
"Silky, I'll lick your pussy for $50," offered Jess.
"No way! You thought my skills were only worth $10!"
"Yeah, but you know my tongue is magic."
That almost got me. She's really able to do amazing things with her nubbin. But I held firm. (George was obviously firm as well.)
"Nope. Will you bet your ass?"
"Ok, but I get $100 for it."
"Deal!" Which didn't mean the cards, it meant I agreed. When we bet our ass, we are offering ourselves up for whippings. We play high stakes poker. We can offer even higher bets.
"Jess, I'll give you $150 for anal sex," George offered quietly.
We all know that we'll give him anal, but we always treat it as a serious subject. Not a casual thing.
"Done." Jessica stared straight into his eyes for about a minute, trying to read his mind. George can keep such a flat affect that no one can read him. So Jess put the $150 in and he called her. I had long since folded.
Jess smiled as she lay out her three Aces, but her face quietly melted as George slowly laid down his three Jacks, and then an eight, and then another eight. So vanished her dreams, so melted her wealth, so toppled her airy castle and left her stricken and forlorn;
Jess just lost the IOU for anal.
"Let's play one more hand!" She begged.
"You got something to bet?"
"Silky, what will you give me for two orgasms?"
"I'm very relaxed at the moment, don't need any." (That was a lie, but we were being business like.)
"I think you have to pay up Jess," said George, never taking his eyes off hers.
A few years ago I didn't even think anal sex was real; it seemed so obvious that a penis wouldn't fit in there without lots of pain and suffering. I've learned a lot since then.
Our usual way of butt fucking is to do it after a long bout of love-making, so that we're all relaxed and ready. George didn't seem to be offering that tonight.
"So can I masturbate a few times first?" Jess asked.
"That wasn't part of the bet," he replied.
"Silky, you don't mind licking me to help me cum first, do you?" Jess's voice was a little anxious.
"Ha! I was told I had poor skills in the oral area. I wouldn't want to subject you to inadequate help."
"I want it on the log." George was cranking up the fear in Jessie's countenance; the log is a padded tree trunk we keep in the back room for serious whippings and bondage. The rules say the winner can claim his or her prize where ever s/he wants it. Even in the Park or in Church.
Jessie hung her head and walked to the back room. I had to admire her legs and derrière. Even in defeat she walked proudly and provocatively.
Since we planned to use the log, I already knew I had to assist. That's how we played every time. Jessie calmly lifted one of her immensely long legs over the log, and settled herself onto it. It is mounted on legs, so that its top is about the height of George's crotch. The leather straps have padding inside them, and buckle down to the legs.
I slid the right arm band around her wrist, and clinched it. Then I walked around to repeat the action on her left. I noted her tears and how she bit her lower lip. Jess feared the actions.
With legs as long as hers, I have to strap both her knee forward and her ankle back, to hold her unable to move. I did this slowly as I felt her fear, for I love my sister dearly.
When I finished with the other leg, she lay spread and exposed with her pelvis over the end, where George had full access to everything. Well I knew how vulnerable she felt, as I had been there my fair share of times. I piddled around checking the straps, pulling her breasts out a little here, pushing in a little there. I stalled as long as I could, until George insisted that I finish.
I took the Crisco off the shelf, as he pointed, and began to ream her anus with the slippery semi-solid. I pushed as much as I could into her ass, and spread it thoroughly around her entrance. Then I turned and knelt before George, taking his erection in my little hand. I layered the grease on his turgid manliness, thinking of my sister's pain if I failed. During all this time, none of us spoke. George even gave commands with a look or a nod.
He is not circumcised, which I see as a good thing. He is more sensitive, so rubbing dry skin is not pleasant to him, either. His impatience won the day, and I put the can away. I asked with an eyebrow if I should assist, and he nodded curtly. I had very mixed feelings; if I helped Jess I would like it, but if she got hurt, it would be partly my fault. Why did she have to make the stupid bet, anyway?
He stepped up to her rear end, with no foreplay, no teasing, no effort to get her ready beyond the lube.
"Wait!" I said. "George, you may really hurt her. She doesn't deserve pain. It was just a stupid poker bet!"
"Do you question my right to fuck her?" His voice resonated in the quiet room.
"No...sir." I added the 'sir' for effect. "It's just that I'm afraid you'll hurt her."
"Didn't you refer to her as having a 'big old loose butt hole' not so long ago?"
"But she's not loose now, she's frightened."
"And what alternative do you propose? She made the bet of her own free will."
"You can fuck my ass instead." How that slipped out, I don't know. I'm much smaller than Jess, and less experienced. Anal sex scares me, and is a rare event. Jess has even done double penetration, which is like 'no way' for me.
George stared at me for long seconds, while I about peed on myself, mentally hitting myself on the head for making such a stupid and potentially agonizing suggestion.
"Jess. Would you agree to let Silky take your place?"
She looked at me with the strangest expression, one I couldn't read. But tears ran down her face.
"No," she said.
"Let me get her relaxed, first, then." I begged.
George glanced from me to her and back again.
"Jessica, do you fear this?" he asked.
'Yes, sir, I do."
"You don't think that being much lubricated, and knowing I would not choose to hurt you -- too much -- protects you?"
"It protects me from being ripped apart, I'm sure. But I haven't cum since yesterday and the longer I wait the tighter I get."
"So what would you propose?"
"Fuck me vaginally first, just to give me a little time."
"But I'm really hard and don't want to be in there."
"The let Silky lick me, or do something to get me going."
I had a flash then, and knew what I could do. I ran across the room and grabbed the short whip. I held it up to George's view, and he smiled and nodded approval. I stood behind her, and brought the scourge across her pink flesh with a loud snap. Her head jerked up off the log, and the tendons of her neck stood out. She screamed an incoherent noise. A bright red line crossed her buttock from the flail.
Repeatedly I flagellated her flesh, until her cheeks became a highway map in blood on ivory parchment. Her screams did not diminish with the blows; if anything they rose in volume, and she strained against her bindings with all her might, but she was secure. She began to curse God, and Jesus, and Mary, in English, Italian, and a few other assorted languages, and I dropped the lash. My work was done.
The only final move I made was to guide George's bulging cock into her orifice. He pushed slowly and steadily, and I watched as she stretched around his shaft. I stepped back and observed that he was so aroused that he could not last long. His thrusting got so fast he was a blur, and then he froze and emptied his scrotum into Jessie's bowels. It took him several moments he was so full, but finally he dropped away, completed.
I stepped to Jess's head and kissed her long and full, a kiss she returned with vigor.
"That looked like fun." I whispered.
"Oh God, Silky, you know me so well. Nothing makes me cum like a whipping."