By sub01

My sister obviously knew exactly what was expected of her.  She crawled forward on hands and knees to the punishment bench.  With obvious reluctance she draped herself over it lengthwise, face down, moving with an ease borne of familiarity as if she had lain over the punishment bench in just such a manner on previous occasions.  The padded bench was just long enough that it supported her from her belly up to just below her neck.  Now the purpose of the narrowed part of the bench became apparent.  The narrowing was positioned just perfectly to let Mary's breasts hang down on either side exposed and open to stimulation (or punishment?) from below.  With her head bowed Mary brought her knees forward until they were at the rear legs of the bench, a position which made her sweet bottom swell out even fuller than it already was and exposed the base of the plug in her bottom and her delicately shaven pussy below.  She brought her elbows back to the front legs of the bench and clasped her hands together in the middle.  Then she waited.

My heart was pounding.  Mary was a vision of perverse sexuality, presenting herself over the punishment bench like that.  If Carol wasn't there I would have dropped to my knees behind Mary and mounted her without hesitation.  But Carol was there, and now she turned to me with an amused smile.

"There are restraints in the nightstand, Brian.  Would you be a dear and use them to secure your sister to the bench?"

Carol didn't need to ask me twice.  I went to the nightstand and found inside a jumble of restraints: two pairs of wrist cuffs, several individual leather cuffs with clips attached, a solitary black leather strap... and a collar.  My cock stiffened at the sight of the collar.  Did Carol expect me to put THAT on my sister?  I knew Mary liked to be restrained, but a collar?

When I turned back around with the restraints in hand, I caught Mary staring longingly at my stiff erection.  She blushed and averted her eyes when she saw I was watching her.  It filled me with lust to know my sister wanted me as much as I wanted her.  I just hoped Carol would let us satisfy ourselves before the night was out.

I brought the restraints over and set them on the bed near where Mary lay draped over the punishment bench.  A quick glance at Carol told me she expected me to secure Mary myself, without any help from her.  I did the wrist cuffs first, since they were the most obvious.  I knelt beside my sister, feeling self conscious as my swollen erection dangled lewdly.  Mary wouldn't meet my eyes but I could tell she was aroused.  Her face was flushed, and there was excitement in her eyes.  I slipped the wrist cuffs around her wrists and tightened them securely.  As I did I caught a twitch of a happy smile on Mary's lips.  She was enjoying this.

There were four sets of individual cuffs with clips attached.  I gathered that these were for attaching Mary to the bench.  The bedroom was silent except for Mary's excited breathing and the soft clink of the clips as I secured the smaller two cuffs around my sister's arms just above her elbows, where they rested against the front legs of the punishment bench.  I saw now that there were rings there, set into the legs of the bench just above the floor.  I clipped Mary's elbow cuffs to the rings, securing her arms to the bench.  Almost immediately she tugged gently at her restraints, her breathing quickening as she confirmed she was secured and helpless.

The second pair of cuffs were bigger and fit snuggly around Mary's legs just above her knees.  Like her elbow cuffs, I clipped these to the rear legs of the punishment bench, securing her legs as well.  Finally I used the remaining pair of wrist cuffs to secure Mary's ankles together.

There were two items left, the collar and the solitary leather strap.  The collar I knew what to do with.  The strap was a mystery, but I had a feeling I would find out its purpose soon enough.  I moved to the front of the bench and coaxed Mary's head up.  As I gazed into her beautiful eyes and smiled at her reassuringly I held her short blonde hair out of the way and fastened the leather collar around her neck.  It was a snug fit, but not so snug that it would be uncomfortable for Mary.  In fact, she looked like she enjoyed it as the collar tightened around her neck.

There was the one strap left.  I turned and looked questioningly at Carol.  "What do I do with this?" I asked.

Carol took the strap from me.  "You do this..."  She gathered Mary's hair up in the back, looped the strap around her bunched up hair a couple times, then pulled her head up and tied the strap off to the back of her collar.  Mary whimpered.  With her hair tied off like that in back her head was forced up and she could only stare helplessly ahead.  Flushed with obvious excitement, Mary smiled at me.  I felt a pang of love and lust for her.  God she was so sexy!  Her adventurous acceptance of such a helpless position aroused me incredibly.  As if reading my mind, Carol spoke up.

"You may kiss your sister, Brian.  But mind you, make it a quick kiss... no tongues."

I leaned forward and kissed Mary gently on the lips... a quick kiss, no tongues, just like Carol said.  It was strangely exciting to perform even such a simple task at Carol's direction.  I wanted desperately to kiss Mary again, more passionately, but instead I rose and stared at my sister.  She looked so sexy, so inviting draped naked over the punishment bench like that, collared and bound and ready for her punishment.  I wanted to study her longer, to enjoy the sight of her, but Carol had other things in mind.

"Would you mind bringing that chair over here, Brian?"

The chair Carol referred to was a formal wooden one that sat at their desk.  I brought it over dutifully and set it a few feet away from Mary, facing her as Carol indicated.  "Have a seat," Carol told me simply.  I sat.  The seat was padded and comfortable, but the back was so straight that I felt like I was sitting at attention.  I put my hands in my laps and waited as Carol moved to the dresser and rummaged around.

When Carol turned back around, she carried in her hand several leather belts.  I watched with growing apprehension as she brought them over.  Without a word she coaxed my arms behind the chair back and started to loop one belt around my wrists.

"You don't need to do that," I told her.  "I won't be a bother."

Carol chuckled.  "It wouldn't matter if you were.  But I think I'll like you better this way."  She tightened the belt around my wrists, binding them tightly behind the chair.  I struggled gently and felt my cock swell.  The sensation of being suddenly helpless, just like my sister, was overwhelming.

As Carol knelt to secure my ankles she looked up at me and smiled.  "You'll have to forgive the use of the belts, Brian.  I simply haven't enough proper restraints.  Your sister and I don't usually entertain guests during our games."

Carol secured my ankles to the legs of the chair using the last two belts.  I expected her to rise and punish Mary now, but instead she remained kneeling in front of me and began slowly running her fingers up my legs.  She teased her way past my knees and then trailed her fingers up the insides of my thighs, tickling me lightly.  I sucked in my breath and tensed.  She was so close to my cock, her fingers so delightfully teasing.  And then before I knew it, her fingers were on my cock, encircling it lightly.  Carol smiled, her lips only inches from my erection.

"You have a nice cock, Brian.  I can see why your sister wants to fuck you."  Before I knew what she was doing, Carol leaned forward and took the head of my cock between her lips.  I gasped at the warm, sudden sensation.  Oh god, her lips felt so good!  I wished desperately for Carol to take more of my cock into her mouth but she seemed content to tease me with just her lips and fingers... and not for very long.  Before I could get anywhere close to cumming she pulled away and stood up, smiling with amusement.

"Tell me, Brian... if there was one part of my body that you would like to see more of, what would it be?"

I didn't answer.  I knew, of course, but I was too embarrassed to say.  Carol seemed to sense this and smiled.  "Come now, Brian, surely there's some part of me that you'd like to see more of."

"Your breasts," I answered softly.

Carol smiled with amusement at my answer.  Surely she knew perfectly well how her breasts affected me.  I Imagined she got more than her fair share of attention from men because of them.  They were so obviously gorgeous.  I knew they were gorgeous, even though I still hadn't seen them bared.  Now Carol moved closer to me, taking the zipper of her dress between thumb and forefinger and beginning to draw it slowly down from her neck.

"Would you like to see my breasts right now, Brian?"

"Yes!"  I was staring at Carol's chest now, well past the point of being ashamed at leering.  She urged her zipper down another inch, which only brought it to the bottom of her neck.  What a tease!  I was about to plead with Carol to please, please let me see more when she suddenly moved forward and without a word straddled my lap.

I felt a surge of lust as Carol settled down on my lap, her silky, stocking clad legs sliding so erotically against my freshly shaven legs.  As she settled down on me the hem of her dress rode up, leaving her sexy lace panties to press against my cock as it lay trapped between our bodies.

"Oh God," I groaned.  Carol's large, leather covered breasts were inches from my face.  Her face was close to mine too, her breath hot and sweet.  As I sat bound and helpless Carol slipped one arm around my neck and began toying with my hair as she eased the zipper on the front of her dress down another inch.

"What would you do, Brian?" she asked softly, her amusement at my plight obvious.  "What would you do to see my breasts?"

"Anything!"

Carol teased the zipper down another inch, to the top of her collar bone.  "What if I gave you a choice, Brian?  To see my breasts, or to fuck your sister?  Which would you choose?"

I hesitated.  As desperately as I wanted to see Carol's breasts, I even more wanted to be with my sister.  "I... I would want to fuck Mary," I said quietly.

Carol giggled and shifted on my lap, rubbing my cock between my belly and her lace panties.  I gasped at the almost overwhelming sensations.  "I'll tell you what, Brian.  I like you... you're cute and you have a nice cock.  So I think I'll give you a chance to do both," Carol said.  She leaned forward more, till her chest was nearly touching my face.  "Unzip me, Brian.  You can see as much as you can unzip."

It wasn't fair.  Carol knew perfectly well that I couldn't unzip her with my wrists bound behind the chair!  But I was desperate and horny.  I craned my neck forward and took the zipper of Carol's dress between my teeth, tugging down on it eagerly.  It was awkward, using only my teeth.  I managed to get the zipper down a few inches to the top of her breasts without much trouble, but after than it became more difficult.  I could only crane my neck down so far, and Carol was so close to me.  Grunting with frustration, I slowly coaxed the zipper down further.  My face soon pressed firmly between Carol's breasts.  They felt so soft and large beneath the supple leather dress, so deliciously exotic.  So different than Mary's smaller, shapelier breasts.  I coaxed the zipper down as far as I could, to a point nearly at the base of Carol's breasts.  The top of her dress sagged open slightly, not enough to bare her breasts but enough to show a tantalizing glimpse of her cleavage.  I felt a stab of arousal.  No tan lines there...

"Could you raise up?" I asked Carol hopefully.  If she would just raise up a little I thought I could get the zipper down far enough to bare her breasts.

"If I did that, how would I manage to tease your lovely cock?"  Carol rubbed her panty covered crotch against my erection in emphasis and I groaned.  A little more of that and I would spill my load all over her crotch.

Carol obviously wasn't going to help me at all.  I continued struggling with her zipper, only to get it down a couple more inches.  That was as far as I could get it.  Bound like I was, and without Carol's cooperation, I was helpless to expose any more than that teasing glimpse of her cleavage.

When it became obvious that I wasn't going to manage to unzip her any more, Carol laughed and rose from my lap.  I groaned as the pressure of her weight left my erection.  God, I'd been so close.

Carol stood smiling at me for a moment, teasing her finger up and down the sliver of bare skin between her breasts which I had managed to expose.  "It's a shame you couldn't unzip more, Brian," Carol said sweetly.  "I don't like to brag, but your sister tells me I have the most luscious breasts..."

I groaned inwardly.  Oh what I would give to see them, to lick them, to suck them!  But it wasn't to be.  With a smirk Carol turned away from me.  Leaving her dress unzipped to just below her breasts and a tantalizingly generous amount of her cleavage on display, Carol once more focused her attention on my sister.    From the look on her face, I knew it was punishment time.

*    *    *

Carol moved behind Mary, out of her sight, and opened up a cupboard beside the bed.  I felt a sudden flush of excitement.  The cupboard was lined with a tantalizing array of toys and devices.  Dildos, vibrators, plugs, even a couple strap-on cocks.  And there were punishment items too: paddles, crops and, dear god, even a whip.  The perverse collection was so much more than Mary or I ever could have dreamed of back so many years ago when all we had to play with were vegetables and other household items.  Obviously Mary's erotic interests had matured over the years.

One by one Carol selected items from the cupboard and lay them out on the foot of the bed.  The items for my sister's punishment, I deduced.  As tantalized as I was by Carol's teasing display of cleavage, I find myself unable to look away from the items she was laying out.  A black leather paddle, a narrow riding crop, nipple clamps, several weights with hooks attached, a pile of plastic clothespins, a vibrator... and last but not least, a large strap-on dildo that made me feel suddenly inadequate.  It wasn't much thicker than my own cock, but it looked to be two or three inches longer.  God, did Carol really use that on my sister!?

While I watched Carol, Mary twisted and turned trying to see what was going on.  But in her bound position and with her hair tied back to her collar she couldn't quite turn far enough to see was Carol was doing.  I could see the anxiousness in Mary's eyes.

When all the items were laid out Carol came back in front of Mary carrying a deck of playing cards.  Mary and I both watched apprehensively as Carol made a show of shuffling the cards.  When she was done, Carol set the deck of cards down on the floor in front of Mary where she would just barely be able to reach them with her bounds hands.  Then Carol stepped back and smiled.  "Now then, would you like to hear how this game is going to work, Mary?"

My sister hesitated, then nodded as best she could in her bound position.  "Yes, please."

"I've laid out several items on the bed behind you," Carol explained sweetly.  "They are the instruments of your punishment.  We will play until your punishment points are exhausted.  At the beginning of each round you will chose a number between one and six which will determine which instrument is to be used on you.  We'll consider number one to be the left most item on the bed, and six to be the right most item.  Understand?"

My sister nodded awkwardly.

"You will then draw a card from the deck in front of you.  The number you draw, multiplied by ten, will be the number of punishment points you will receive from the particular item chosen.  I've taken all the face cards out, so the cards range from one to ten... a possible range of ten to one hundred punishment points possible each time."  Carol paused for a moment and smiled.  "I've left the jokers in, though.  Do you know what they do, Mary?"

Mary shook her head.

Carol smiled.  "If you draw a joker, your next card will determine points added to your remaining total, instead of subtracted."

My sister looked dismayed at the thought that her already large amount of punishments points might grow even larger by the time the game was over.

"Now remind me, Mary... how many punishment point have you earned?"

"Two hundred," my sister said softly.

"That's a lot of points," Carol whistled softly.  "I'll bet we go through all the items before we're done."  Carol was smiling, as if she relished just such a thought.  "Well, Mary, tell me when you're ready to begin."

My sister was quiet for a long moment.  When she finally spoke, her voice was barely a whisper.  "I'm ready."

"Okay, pick an instrument," Carol told her sweetly.  "One through six..."

Mary instinctively tried to turn her head to see the items, but her bindings kept her securely in place and staring forward.  She hesitated and then whispered softly, "One, I guess."

My eyes immediately went to the bed.  Item one, the left most, was the paddle.

"And how many points should I give you with item number one?"

Mary turned the top card over.  It was the three of spades.  Multiplied by ten, that meant thirty strokes of the paddle.

"You got lucky," teased Carol.  "I was hoping for a nine or a ten."  She moved behind my sister and picked up the paddle, holding it out of Mary's sight.  "Beg me to punish you, Mary."

Mary glanced at me and I could see the apprehension in her eyes, the anxiety she must feel at not knowing what instrument she was to receive punishment from, yet having to beg for it.  And yet there was arousal there, an unmistakable excitement gleaming in her eyes.  "Please Carol... please punish me?  I... I deserve it.  I--"

Carol brought the paddle down hard on my sister's bottom, cutting her off in mid sentence.  The resounding crack was surprisingly loud in the quiet bedroom.  Mary jerked forward, wincing.

"Ow!"

"That's one," Carol announced.  "Brian, I want you to keep track.  I'll expect you to know at all times how many punishment points your sister has satisfied.  Understand?"

"Yes," I said softly.  I couldn't take my eyes off Mary's bottom.  A red blush was appearing where the paddle had struck, an intoxicating mark on the smooth, pale skin of my sister's bottom.  It was so much more vivid than the marks that my hand, or even the hairbrush, had left when we'd played during our youth.

Smack!  Carol swung the paddle again, this time striking Mary's right buttock.  Again my sister jerked forward in her bonds, but this time she didn't make a sound.  I guessed that she was ready for it this time, knowing now what to expect.  She still winced, though.  I could tell the paddle hurt.

*    *    *

I tried to keep count, I really did.  But Carol swung so fast, without letup, and I was so aroused by watching her paddle my sister that when she stopped suddenly and asked me how many points Mary had satisfied, I couldn't remember for sure.  "Twenty?" I guessed.

"Actually, it was twenty three," Carol said.  I was momentarily relieved.  At least I had guessed low.  I imagined there might be some additional punishment if I guessed high.  My relief was short lived, however.  "We'll have to begin again," Carol announced.  "This time, Brian, I suggest you keep better count."

Mary's eyes were wide with dismay at the prospect of beginning again.  Her bottom was already flushed bright red.  This time I kept better count, repeating to myself over and over what number we were on even as I watched Carol paddle my sister again and again.  By the tenth blow of the paddle Mary was yelping at every strike, and by the twentieth there were tears in her eyes.  But, dear god, she was smiling!

When Carol stopped suddenly and asked once more what the count was, I was ready.  "Twenty five," I declared.

"That's right, Brian, very good.  I'm sure your sister thanks you for your accuracy."  In fact, the relief was obvious in Mary's eyes.  She smiled at me during this brief pause, and I smiled back.  I was hornier than ever watching her be paddled like this.  Mary seemed about to say something, but just then Carol struck again with the paddle.

"Owww!"

Carol landed the last few strokes of the paddle quickly and harshly all over Mary's bottom, each blow making a resounding smack.  By the time Carol set the paddle aside my sister was panting heavily and grimacing.  The pale, smooth skin of her bottom was flushed bright red.  It was an intoxicating, unbelievably arousing sight, and I could tell that despite her discomfort Mary was as turned on from receiving the paddling as I was from watching it.

"How many punishment points does you sister have left, Brian?"

"A hundred and seventy," I answered.

"Still a long way to go," Carol said with a smile.  "So many exquisite possibilities.  Okay Mary, which item should we use next?"

*    *    *

"Item four," Mary decided softly.  I glanced to the bed and felt my heart leap.  The nipple clamps and weights...

"Splendid!" Carol said.  "Don't bother drawing a card, Mary.  For this one I'm going to let you choose how many points you earn.  Now then, there are two parts to this punishment..." Carol picked up the nipple clamps, smiling wickedly.  "Here's the first part..."

My sister's eyes widened and she let out a surprised gasp as Carol let the first clamp ease shut on her nipple.  Mary obviously hadn't been expecting it, and by the look in her eyes it obviously wasn't a soft, gentle clamp.  Carol quickly let the second clamp ease shut on Mary's other nipple.

"Owww!  Jesus, that hurts!"

"Now for the second part," declared Carol.  "The weights."  Mary groaned at this and Carol smiled.  "I'll give you five points a weight.  How many do you want, Mary?"

Mary hesitated.  "Are they the small weights, or the big ones?"

Carol chuckled.  "You'll just have to guess."

Mary obviously wasn't thrilled about that.  "Forty, I guess."

"Forty points, or forty weights?" teased Carol.

"Points!" Mary quickly exclaimed.  Forty punishment points.  At five points a weight that meant eight weights...

"Forty points it is," Carol chuckled.  "And just for your reference, they're the big weights."

Mary groaned with dismay.  But before she could protest or beg out of her punishment, Carol leaned down and hung the first weight from her right nipple clamp.  Mary gasped and grimaced.

"There now, that's not so bad is it?" cooed Carol.  "Only seven more to go."  She quickly followed her words with the next weight, this time hanging it from my sister's left nipple clamp.  Mary winced.  Six more to go...

I winced in sympathy as Carol hung a second weight from Mary's right nipple, and this time her nipple stretched downward obscenely.  Mary's eyes widened and she grimaced.

"Oh God!"

"Nice, huh?" teased Carol.  My sister didn't answer.  She bit her lip and grimaced as Carol set the two weights on her right nipple swinging gently.  As sympathetic as I was to my sister's discomfort, I was also aroused.  Mary's nipple was distended downward by the two weights.  It was an intoxicating sight.

When Carol hung the next weight from Mary's left nipple, my sister gasped.  "Ow!  Oh Carol, please, no more!  They're too heavy!"

"We still have four more to go..."

"Please, I can't take them!"

"If you give up now, you forfeit the forty points."

Mary looked dismayed.  "I'm sorry Carol, I... I just can't take any more."

"So you forfeit the points?"

Mary hesitated, then shook her head.  "No, please Carol, don't make me."

Carol considered my sister for a moment, then reached down and slipped her hand between Mary's legs.  I couldn't see very well from my vantage point, but by the look on my sister's face I could tell Carol had slipped a finger or two into her pussy.  "I'll tell you what, Mary.  I'll give you a choice.  Better yet, I'll give your brother a choice."  Carol turned to me and smiled.  "What do you think, Brian?  We can hang the final four from your sister's nipples, or from her pussy lips.  Your choice..."

Mary's eyes widened and she gasped, but she said nothing.  Obviously neither choice appealed to her.  I sat frozen, aroused by the choices and prospect of seeing my sister's nipples tortured more, or even better her pussy lips, but I couldn't bring myself to choose.  When I didn't answer, Carol began to hang the next weight from Mary's right nipple.  Mary's look of dismay became one of pain.

"Her pussy!" I exclaimed as the weight began to settle on those already hanging from my sister's nipple.  "Please, put them on her pussy!"  I wasn't sure if it was a better choice or not, but I could tell Mary really didn't want any more hanging from her nipples.

"An excellent choice, Brian," Carol told me with a smile as she lifted the weight free.  "I'm sure your sister appreciates it."

As Carol turned to retrieve another pair of clamps from the cupboard, Mary caught my eye.  With a meek smile she mouthed the words "thank you".  I smiled back at her and started to say something, but Carol came back with a tiny pair of spring loaded butterfly clamps.  She knelt and stroked Mary's pussy lips for a moment, coaxing them apart, and then one by one she eased the clamps shut on them.

Mary winced and gasped.  "Oh God!"

"There now, that wasn't so bad, was it?"  Carol stroked my sister's pussy lips gently, easing the discomfort she obviously felt from the clamps.  When Mary relaxed Carol brought one of the weights up and hung it from the clamp on her right pussy lip.

"Ohhh..."

"Three more to go," Carol told her softly.  She hung the last three in quick succession, not giving Mary time to complain.  When she was done my sister had two weights hanging from each nipple and two from each pussy lip, and her face was contorted in a mixture of pleasure and pain.

"Don't pay her any attention," Carol chuckled, seeing my expression.  "You might not be able to tell by her face, but your sister just loves being clamped and teased."

I didn't doubt that for a second.  Mary had always liked having me pinch and bite her nipples, and now I could see that even with as much discomfort as she was in there was excitement and arousal in her eyes.  And oh how erotic those weights looked hanging from her most sensitive parts.

"How... how long do I have to wear these?" Mary asked quietly.

Carol smiled.  "Why, for the duration of your punishment, of course.  I wouldn't think of short changing you."

Mary was wide eyed at this.  I got the distinct impression that Carol hadn't punished her quite so deviously before.  Maybe Carol was even doing it for my benefit.

"How many points left, Brian?"

"A hundred and thirty," I answered.

"Oooh, almost halfway.  Well Mary, chose your next weapon..."

*    *    *

My sister was quiet for a long moment.  "Three," she finally whispered.  The pile of clothespins.  I winced at Mary's unknowing choice.  As if the nipple clamps and weights weren't enough...

Carol seemed delighted by Mary's choice.  "I wouldn't have thought you'd want the clothespins so soon after the clamps," she teased.  A strange look registered on Mary's face at the mention of clothespins... a mixture of apprehension and, I thought, excitement.  "I'll let you off easy this time," Carol said as she picked up the first clothespin.  "No multiplier.  The card you draw is how many clothespins you get."

Mary hesitated, then turned the top card over.  I felt a surge of excitement.  Ten.  My sister gasped, her eyes wide.  "Oh God!"

"Oooh, you must really be a glutton for punishment," Carol giggled.  "Well, ten it is.  And I want you to count them out, Mary."  Without even giving Mary a moment to prepare for what was coming Carol reached out and let the first clothespin ease shut on the back part of Mary's right leg, just below the swell of her buttock.

Mary jerked forward against the punishment bench, her eyes wide.  "Ow!  Jesus!"

"Does it hurt?" teased Carol.

"Yes!"

"Good hurt, or bad?"

"It's... it's good hurt," Mary admitted with a grimace.

"Don't forget to count," Carol reminded as she selected the next clothespin.

"Oh.  That... that was one."

"And this is two..."  Carol let the second clothespin ease shut, this time on Mary's left side just below her breast.

"Ow!  Ohhh, fuck!  That's... that's two."

Carol took her sweet time affixing the clothespins all over my sister's body.  She seemed to make a point to not follow any pattern.  She placed the third and fourth clothespins on the lower swell of Mary's right breast, then the fifth on her tummy and the sixth and seventh on the delicate skin of Mary's left rear thigh.  Mary grimaced, seeming to dislike the ones on her thighs the most.  "Seven!" she gasped.

I felt almost ashamed for being so aroused at watching my sister's plight.  But I could tell that despite her discomfort, she was enjoying what her lover was doing to her.  Carol let clothespin number eight ease shut on Mary's left outer labia, a couple inches down from the clamp that was already there.  Number nine went on Mary's right labia.

"Nine!" gasped Mary, grimacing.  One more to go.  Carol took her time with this one, trailing it all over Mary's backside and over her bottom, teasing her.  She stroked the clothespin up and down Mary's already tortured slit, then teased the clothespin over her clit.  Mary's eyes widened at this, and I felt dreadfully sure that Carol was going to place the clothespin there.  But to my relief – and obviously Mary's relief – Carol moved a little higher and eased the clothespin shut on the lower swell of my sister's belly.

"Oww!  That's ten," Mary gasped.

That was the last of the clothespins, but Carol wasn't quite finished.  Now she went around my sister's body twisting and tugging on the clothespins, checking that they were fastened securely.  Not satisfied with just one testing, Carol made the circuit of the clothespins two or three times, each time in a different order.  The entire time Mary gasped and winced, but not once did she complain.

"Okay, I think we're ready to continue," Carol finally declared.  "How many points does your sister have left, Brian?"

"A hundred and twenty."  Still so many points, and only three items left.  I wondered what would happen when we exhausted all of the items.

"Now Brian, I don't want you to feel left out so why don't you choose the next item..."

*    *    *

I scanned the items on the bed.  There were three left: the riding crop, the vibrator and the strap-on dildo.  As eager as I was to see Carol use the strap-on on my sister, there was one other item that aroused me even more.  "The vibrator," I said.

Mary smiled at my choice.  Finally she would get a little pleasure.

"Okay Mary, draw a card.  That, multiplied by ten, will be how many seconds you get the vibrator for."

Mary drew a four and smiled.  Forty seconds of pleasure...

"Oooh, nice.  Now Mary, I'm going to give you a choice."  Carol turned the vibrator on and teased it over my sister's bare bottom, letting her feel the vibrations.  "For the full forty points you can have the vibrator in your pussy, or for half that – twenty – you can have it on your clit.  Which would you prefer?"

"On my clit!" Mary exclaimed eagerly.  "Oh please, Carol, on my clit!"

Carol chuckled.  "Okay, clit it is for twenty seconds.  Brian, watch the clock and tell me when to stop."  And with that Carol reached between Mary's legs and pressed the humming vibrator to her clit.

My sister jumped as if she'd been shocked.  "Oh, God!"  She immediately began squirming in her bonds, rocking against the padded punishment bench.  Her desperate need was obvious.  As Carol teased her clit with the vibrator, Mary grimaced and began moaning softly.  I glanced at the clock.  Already we'd used five seconds.

"Ohhh... ohhh, just like that Carol!" Mary gasped.  I felt aroused and surprisingly jealous watching my sister squirm in pleasure.  I wanted to be the one to give her that pleasure.  I wanted to give her an orgasm, or two or three.  But instead Carol was going to.  Mary's face was flushed now, her eyes drooping shut dreamily.  I could tell she was already close to orgasm, even so soon after the one she'd had in the shower.    I glanced at the clock and felt my heart sink.  Fifteen seconds.  Only five more.  I didn't want to have to tell Carol to stop, but it was almost time.  Just a couple more seconds.  Oh God, Mary was so close.  I just couldn't bear to stop things when she was so close.  But what would Carol say if I cheated and let the time run long?

"Time," I said reluctantly when twenty seconds were up.  Carol immediately took the vibrator away from my sister's clit.

"No!" cried Mary.  She opened her eyes and tried to twist in her bonds.  "Oh, please Carol, just a little more!  I'm so close!"

"But that was twenty," chuckled Carol.

"Please!?"

"Okay, I'll tell you what.  I'll put the vibrator back on your clit until you cum..."

Mary looked absolutely relieved.  "Oh, thank you!"

"...but it'll cost you.  You earn one additional punishment point for every second the vibrator is on your clit.  So Mary... is that orgasm worth it?"

Mary didn't even hesitate.  "Yes!" she exclaimed.

"Okay.  Keep track, Brian."

With that Carol pressed the vibrator against Mary's clit again.  This time Mary was wide eyed with delight.  Smiling happily, she began humping her hips up and down, moving against the vibrator.  I watched breathlessly, feeling flushed myself, counting the seconds.  Five seconds, ten seconds, fifteen.  At twenty seconds it was obvious that Mary was on the brink of orgasm.  Smiling wickedly, Carol reached underneath her with her free hand and began pulling on the weights that hung from her nipples.

"Oh God!"  Mary bucked hard against the punishment bench as she came.  I knew she was cumming.  She had that unmistakable, exquisitely delightful, breathless look on her face, her eyes fluttering shut dreamily as her orgasm washed over her.  Carol kept the vibrator on her clit throughout her orgasm, even when Mary's look of delight began to turn to that of discomfort.  I knew how sensitive Mary's clit became after her orgasm, and now I knew the moment was past and the vibrations had to be hurting.

"Please, that's enough," Mary gasped.

But Carol kept the vibrator on her clit.  My sister began squirming again, this time in discomfort.

"Carol, please!  That's enough!"

"How many points does your sister have remaining?" Carol asked me casually.  I did the math quickly in my head.  We'd started at one twenty, minus twenty for the vibrator on Mary's clit but then plus thirty or so till orgasm...

"A hundred and thirty," I said.  Mary had gotten an orgasm out of the vibrator, but she'd earned more points in the process.

"I'll tell you what, Mary," Carol told my squirming sister.  "I'll take off five points for every second you can take this vibrator on your clit without making a sound.  Want to try?"

My sister hesitated, her face scrunched up in discomfort, then nodded.

"Okay, start counting Brian."

I counted.  One second, two seconds, three.  By five seconds Mary's face was bright red and she was biting her lip to keep from making noise, and by seven seconds tears were beginning to form around her tightly closed eyes.  She was grimacing and squirming in discomfort.  God, the vibrator must be pure torture now on her obviously sensitive clit.  At ten seconds Mary bared her teeth in agony, and at fourteen seconds she just couldn't hold out any longer.

"No more!" Mary sobbed.  "Please Carol, it hurts!  No more!"

Carol took the vibrator away and turned it off.  Mary sagged weakly against the punishment bench, trembling and whimpering.

"How long was that, Brian?" Carol asked me.

"Fourteen  seconds."

Carol nodded approvingly.  "Seventy points.  I'd say that last fourteen seconds was well worth it.  Now thank your brother, Mary.  After all, he chose this punishment."

Mary opened her eyes and smiled up at me dreamily.  "Thank you, Brian."

I felt particularly pleased with myself.  I'd already given Mary two orgasm's this evening, albeit one via Carol's hands.

"Okay, sixty points left," Carol reminded Mary as she set the vibrator aside.  "And only two items remaining.  Which will it be next, Mary?  Item six or item two?"

I waited breathlessly.  Would it be the strap-on, or the riding crop?  Mary seemed indecisive for a moment, as if hesitating would somehow help her make a better choice.  "Six," she finally decided.

My cock stiffened.  The strap-on dildo...

*    *    *

Carol moved behind Mary and without a word picked up the strap-on dildo.  I expected her to tease Mary with it, to make Mary draw a card, but instead she casually pulled her dress up around her waist and stepped into the harness.  She pulled the strap-on dildo into place over her black lace panties and then tightened the straps securely.  As she did this my sister twisted and turned in her bonds, trying desperately to see what was going on.

"Are you ready to see what number six is?" Carol teased my sister.

"I... I think so," Mary said quietly.  She didn't sound too sure, as if she expected some devious surprise.  As Carol came around in front of her Mary smiled.

"Oooh..."

"I'd hoped to use this before the vibrator, but I guess we'll just have to make do," Carol said.  "Okay Mary, draw a card.  It's a stroke with the dildo for every point."

Looking delighted at that thought, Mary drew a card.

"Oooh, twenty points," cooed Carol.  "Nice..."

Mary seemed to think so too.  She was eyeing the dildo hungrily, as if her recent orgasm hadn't sated her in the least.

"Now, you have a choice Mary: which hole would you like this in?  I'll give you straight points for your cunt, half for your mouth, double for your ass."

Mary hesitated, obviously unsure.  Double the points would nearly finish her punishment and probably save her from a lot of strokes from the crop (which she still hadn't seen yet).  But I knew how much Mary disliked having anything in her bottom.  Her reaction earlier to the anal plug was testament to that.

"Maybe if I show you the last item it'll help you make up your mind?" offered Carol.  Mary nodded.  The rubber cock bobbing, Carol moved behind Mary and picked up the riding crop.  When she brought it back around, Mary's eyes widened and her smile faded.

"Oh my God, what's that!?"

"A riding crop," Carol chuckled, swishing the crop through the air wickedly.  "I just picked it up last week.  It's quite painful.  You'll love it!"

The look on my sister's face made it clear that Carol hadn't used a crop on her before, and that she in fact would NOT love it.

"Well Mary, which will it be?  Cunt or ass?"

"My... my ass," Mary decided quietly, her eyes flicking between the dildo and the crop.  Obviously she wasn't thrilled about either prospect, but even more she clearly wanted to minimize the punishment she would receive from the wicked looking crop.

"Are you sure?  This cock is pretty big."

Mary hesitated, her indecision obvious.  "Yes, I'm sure," she said softly.

"Okay, ass it is.  Maybe you'd like to get it lubed up first?"

"Yes, please!"

Carol chuckled at my sister's eagerness and moved close, till the tip of the strap-on dildo was at Mary's lips.  I thought I detected a blush in Mary's cheeks as she opened her mouth and took the head of the dildo in.  She sucked it eagerly, wrapping her lips tightly around the shaft and licking and lapping with her tongue, smearing her saliva up and down the dildo... preparing it for her tight bottom.  I felt my cock swell just watching my sister perform so lewdly.  She had obviously become a very talented fellatrix in the years since we'd last been together.

Soon all but the last couple inches of the shaft glistened with my sister's saliva.  Carol put her hands on the back of Mary's head and coaxed the dildo deeper, speaking to her softly as she did.  "Take it deeper, Mary.  All the way.  Show your brother what a good cock sucker you've become.  Imagine it's that nice man's cock that I let you suck last week... remember how good you said he tasted when he came in your mouth.?  That's it, take it all the way into your throat you little slut..."

As Carol "sweet talked" my sister, she eased the shaft – dear god – all the way into Mary's throat until her lips were pressed around the base of the cock.  I could see Mary's wide eyes, hear her muffled gagging.  Carol pumped her cock in and out of Mary's throat a few times, making my sister squirm and gag.  Tears formed in the corners of Mary's eyes and I knew she was struggling with the dildo's length. 

When Carol finally pulled the dildo out of my sister's mouth the entire shaft glistened with saliva.  Mary was red faced from her effort.  While she breathed heavily, catching her breath, Carol moved behind her and positioned the strap-on at Mary's pussy.

"Remember, Mary, this is punishment..."

"Yes, I--"  Mary grunted as Carol swiftly thrust the dildo deep into her pussy with no pretense.  If it was punishment, it wasn't obvious by the look on Mary's face.  She look absolutely ecstatic as Carol slowly pumped the dildo in and out of her pussy.  The wet, lewd sucking was clearly audible in the bedroom.  Mary was obviously wet and ready.

I thought Carol might have forgotten that Mary had asked for it in her ass, but soon Carol began twisting and pulling on the base of the anal plug that was nestled so snugly between my sister's bottom cheeks.  As she slowly fucked my sister with the strap-on Carol begin tugging on the anal plug rhythmically, easing it closer and closer to pulling out of Mary's bottom.

I wished I had a better vantage point, that I could see the actual withdrawal and penetration.  But from where I sat I had to be satisfied with seeing Carol's movements and reading the reactions on my sister's face.  I saw Mary flinch as the thickest part of the plug pulled through her sphincter, and then she groaned softly as Carol eased the plug out.  Her relief was short lived, though.  Almost immediately Carol slid the strap-on out of my sister's pussy and moved it higher, guiding it to her asshole.

"Please Carol... go slow?"

"Of course, my love," Carol cooed softly.  "I wouldn't do it any other way."

Carol did do it slowly... almost too slowly.  In my eagerness I wanted to see her thrust it home, to take my sister's ass swiftly like she did her pussy.  But instead she eased it into Mary's bottom slowly, pushing in and then retreating, going a little further each time while stroking Mary's back and bottom.  Caressing her, loving her.  Obviously Mary wasn't quite as experienced with her bottom as she was with her mouth and pussy.  But then, the dildo was awfully big.

When Mary groaned and her eyes fluttered closed I knew Carol had seated the dildo all the way into her bottom.  Carol stroked her backside for a moment and then smiled at me.

"Count out the strokes, Brian.  Every time my hips touch your sister's bottom is one."  She eased the dildo almost all the way out of my sister's asshole, then slowly pressed back in until her hips were against Mary's bottom.

"Uhhh," my sister grunted.

I felt my cock swell to see such an odd expression on Mary's face, as if she didn't know whether the sensations felt good or bad.  "One," I counted.

"One, ma'am," Carol corrected me.  "It's time you started addressing me properly, Brian."

"One, ma'am," I said quietly.  It felt exquisite to play submissive to Carol like this.  She smiled and thrust again slowly in Mary's bottom.

"Uhhh!"

"Two, ma'am," I counted, properly this time.  Carol seemed pleased with this and thrust twice into Mary's bottom in quick succession, pressing deep each time.

"Uhhh!  Oh, Carol!"

"Four, ma'am."

Carol took her time sodomizing my sister with the strap-on dildo.  With every stroke she pulled nearly all the way out, then pressed back in until her hips were tight against Mary's bottom.  She made sure my sister took the entire length of the dildo on every stroke.  In true, devious fashion Carol varied the tempo of her thrusts, at one moment giving Mary several seconds pause between impalements and at the next delivering two or three thrust in quick succession.  We were quickly at ten thrusts, and then fifteen.  Mary's face was red and her eyes wide, but I could tell she was opening up to the cock.  Carol's thrusts were becoming easier, and the smile forming on Mary's lips was no longer just a fleeting hint.  My god, she was actually enjoying having her bottom fucked...

As we neared the end of Mary's "punishment" with the strap-on, Carol gave her the last few thrusts in quick, steady succession, fucking her deeply and without pause.  Mary grunted with each impalement, gasped each time the cock withdrew.  I tried to imagine how she must feel each time the thick shaft pulled her insides out, how it must feel forcing back inside.  Seventeen strokes, eighteen, nineteen.  Finally I counted "Twenty, ma'am," and Mary groaned.  I couldn't tell if she was happy or disappointed that her "punishment" with the strap-on was at an end.

But it wasn't at an end... at least not quite yet.  With the strap-on cock still buried in my sister's bottom, Carol leaned forward over Mary's back and kissed the back of her neck.  "Twenty points left, Mary, and there's only the riding crop left."  Mary groaned at the mention of the crop and Carol chuckled.  "Draw a card, Mary.  How many points with the crop?"

With the dildo still buried in her bottom, Mary groaned and drew a card.  Her eyes widened, and when I looked to see what card she'd dawn I saw why.  It was a joker...

"Oh no!" Mary exclaimed.  She stared with dismay at the joker and I knew exactly what she was thinking: that with the next card she drew she'd be adding punishment points instead of subtracting, and all under the punishment of the crop.

Carol seemed delighted at my sister's luck.  "Oh my, you must really be looking forward to the crop," she chuckled.  "Okay, draw another card."

Mary drew reluctantly and sighed with relief.  A one.  Ten strokes of the crop.  But she'd end up with thirty punishment points left.

"Oooh, you get the crop and thirty points left to boot," Carol observed.  She began unfastening the strap-on dildo even as it remained buried deep in my sister's bottom.  "I'll tell you what, Mary.  If you can hold this dildo in your bottom for the duration of the ten crops, I'll consider your punishment over.  Otherwise I double the points remaining to sixty and we keep going.  What do you think... want to try?"

Mary hesitated.  "Yes... thank you Carol."

Carol chuckled.  "Don't thank me yet... you still have ten crops coming."

*    *    *

While Mary remained kneeling over the punishment bench with the strap-on cock still stuffed deep in her bottom, Carol rose and picked up the crop.  She swished it through the air a couple times, smiling as it whistled ominously.  My poor sister flinched each time the crop sliced through the air, no doubt expecting it to land on her bottom.  Finally Carol placed the tip of the crop against Mary's naked, exposed bottom and held it there.

"Tell me when you're ready, Mary."

My sister was quiet for the longest time, the apprehension clear on her face.  Finally she breathed deeply.  "Okay, I'm ready Carol," she said softly.

Carol lifted the crop and swung it through the air once, twice, three times.  Mary jumped each time.  The fourth time, when Mary obviously was expecting another tease, Carol landed the crop sharply on her bare bottom.  Mary lunged forward on the punishment bench, arching her back.

"Oww!  Fuck!  Oh Jesus Carol, that hurts!"

Carol chuckled.  "It's supposed to."

I was fixated by the sight of my sister's bottom.  A red welt had appeared where Carol struck her with the crop, vivid against the pale flush that the paddle had left earlier.  I met Mary's eyes.  She looked flushed and worried.  Nine more to go...

When Carol struck Mary's bottom a second time with the crop, I saw the strap-on dildo slip out an inch.  Mary's desperate, defensive movements under the pain of the crop were forcing the dildo out of her bottom.

Crack!

"OWW!  Carol, please!"  Mary was trembling against the punishment bench now, three welts clearly visible on her bottom.  And the dildo had slipped out further.

Carol lay stroke number four on Mary's other buttock, surprising her.  My sister leapt forward in her bonds, sobbing as she dildo slipped out further still.

"Carol, wait!  Oh please, wait!  It's slipping out!"

Carol didn't wait.  In fact she seemed to enjoy the fact that Mary was about to fail in her attempt to retain the dildo.  She delivered the next two crops in quick succession, striking Mary hard on her left buttock.  Mary arched her back and cried out as welts flared.  The dildo slipped out a little more, threatening to unseat all the way.  Then with the next blow, which Carol laid quickly on Mary's right buttock without warning, the dildo did slip out of Mary's bottom, falling to the carpeted floor with a soft thud.

"Nooo!" my sister cried with dismay.

Carol smiled but said nothing.  She delivered the three remaining strikes of the crop leisurely now, taking her time and teasing Mary between strikes.  When she was finally finished she set the crop aside and knelt to soothe my sobbing sister.  "There now, that wasn't so bad was it?"

"Yes, it was," sobbed Mary.  "Please Carol, don't ever use that on me again!"

"We'll see," Carol said softly.  "Now then, you still have sixty punishment points and we're all out of items, so I'll let you choose how you want to receive them."

My sister was quiet for a moment, and then she looked up and smiled at me.  "I'd like my brother to spank me with the paddle..."

*    *    *

I was flush with excitement as Carol unbound me from the chair.  The prospect of paddling my sister, and at her request no less, was exquisitely arousing.  I liked the idea almost as much as Carol seemed to.

"Make it hurt," Carol told me with a smile as I rose and retrieved the paddle.  "I want to hear it in your sister's voice.  If I'm not satisfied, I'll put her in a chastity belt until you go home."

The leather paddle was heavier than I expected, a far cry from the hairbrushes my sister and I had used in our youth.  I moved behind Mary and stared down at her wonderful, shapely bottom.  Her pale skin was flushed and marred from the paddling and cropping, and now I was to give her more.  I teased the paddle gently over Mary's bottom, as much to calm myself as her.  She looked so lovely kneeling there submissively over the punishment bench.  The position made her bottom cheeks swell out, and between them I could see the tight pink pucker of her anus, still slick with her saliva from the fucking.

Carol was impatient.  "Hurry up Brian, I'm waiting.  And remember, I want to hear it in her voice."

I nodded uneasily.  As aroused as I was, I wasn't entirely sure I could bring myself to make it really hurt.  I loved Mary, after all.  I wanted to please her, not hurt her.  Even if she wanted it, which obviously she did.  I lifted the paddle and swung it hard, aiming at her left buttock.  It landed with a surprisingly sharp crack! and I nearly jumped.

"Ohh!" Mary exclaimed.  I couldn't see my sister's face, but I could hear the discomfort in her voice.  I glanced to Carol.  She didn't look displeased, but I could tell she expected me to strike Mary harder.  I swung again.

Crack!

This time Mary jumped.  "Ow!"

"Count them out," Carol instructed Mary.  "And thank your brother each time."

"Two," Mary gasped.  "Thank you, Brian!"

I felt a surge of arousal at hearing my sister thank me.  I swung the paddle again, this time landing it on her shapely right buttock.

"Ow!  Three, thank you Brian!"

"Harder," Carol demanded.  "I want to really hear it."

Tightening my grip on the paddle I swung again, hard.

CRACK!

"OWW!  Jesus!  Four!  Th... thank you, Brian!"

Mary was squirming against the punishment bench now, wriggling her bottom as it began to flush a brighter red than before.  I began paddling her firmly and rhythmically, delighting in how she counted and thanked me each time.  I alternated between her bottom cheeks, reddening one for a bit before switching to the other.  By the time we reached twenty Mary was squirming uncontrollably and flinching each time I started to swing the paddle.

"OWW!  Shit!  Twenty five!  Oh fuck, thank you Brian!"

When we reached forty, Carol told me to make the last twenty really hurt.  "I want to hear her scream," she demanded.

I paddled Mary as hard as I could bring myself to.  She yelped and writhed with each strike, her bottom obviously very sensitive now after so much punishment.

"FUCK!  Oh shit!  Fifty, thank you Brian!" I could tell she was sobbing now.  "Please Brian, hurry and finish!"

By the time I landed the last blow of the paddle my sister's bottom was bright red and her cheeks were wet with her tears.  But she was smiling.  It was as if satisfying her punishment, and satisfying Carol, meant more to her than the discomfort she endured.  Obviously Mary had enjoyed her punishment.

"Sixty!" Mary sobbed.  "Oh fuck, oh thank you Brian!"

Now Carol knelt beside Mary and began freeing her.  One by one she removed the clothespins from my sister's pale skin, and with each one Mary winced anew.  Then Carol moved to the weights, lifting them gently and unhooking them from the clamps on my sister's nipples and pussy lips.  When she last of the weights was off Mary smiled with relief.  But soon she winced and gasped as Carol eased the clamps off her nipples and pussy lips.  Taking them off seemed to be more painful for Mary than having them put on in the first place.  Finally Carol released my sister's bonds and un-strapped her hair from her collar.

Mary eased off the punishment bench slowly, her movements careful as if her whole body ached.  I imagined she would be stiff after so long over the bench.  But she was smiling.  Naked, her breasts swaying gently, she crawled over to me and waited on hands and knees, looking up at me with a hopeful smile.  She looked so lovely, so unbelievably submissive kneeling there at my feet.

"She wants to kiss the paddle," Carol told me with amusement.

I was stunned.  I held the paddle out and sure enough my sister pressed her lips to the stiff leather, kissing it gently.  "Thank you, Brian," she told me softly.

"You're welcome," I said, not sure what else to say.  Even after having seen her punished so thoroughly, my sister's obedient show of submission surprised and aroused me.  My cock was standing out stiffly.  Before I knew what was happening, Carol moved close to me and took my erection in her hand, stroking gently.

"Mmm, it looks like watching your sister's punishment aroused you, Brian."  It was true, watching Mary's plight had been extremely arousing.  Paddling her myself had just made me that much more horny.  I started to say something, then gasped as Carol tightened her grip on my erection.  "I bet you'd like to fuck her now, wouldn't you, Brian?"

"Yes, ma'am!" I gasped.  She was squeezing my cock rhythmically, not strong enough to bring me off but enough to tease me.

"She's told me all about you, Brian," Carol told me with a smile.  "About how you corrupted her..."

I didn't say anything.  That wasn't entirely true.  Mary had helped corrupt me as much as I had her, maybe even more.  Besides, it seemed like Carol had corrupted my sister far more since then than I ever had.

"I'll bet you'd like to do all sorts of nasty things to her with this lovely cock, wouldn't you?"

I nodded.

"And to me?"

"Oh, yes ma'am!"

Carol laughed sweetly.  "So eager!"  She squeezed my erection one last time and then let go, leaving me standing in frustration as she moved to where my sister now knelt waiting patiently.  "Rise, Mary."

Mary rose and stood obediently.  Her cheeks were flushed, but with excitement now.  Carol stroked her hair lovingly and kissed her gently on the lips, then on her cheeks, and then lower, at the base of her neck.  "Go straighten yourself," Carol told my sister softly.  Mary's modest makeup had smeared from the tears she'd shed during her punishment, and her hair was in disarray.  "And put on something sexy," Carol added with a smile.  "Something your brother will like."

Mary nodded and went into the bathroom.  When she was gone, Carol turned to me with a sly smile.  "Well Brian, we've taken care of you sister's punishment... now it's time for yours."