Blackmailing My Sis

Blackmailing My Sis

By unknown

Jeff sat on the floor at the end of Amy’s bed, resting against the footboard. Amy had her legs slung over his shoulders with her feet resting on his knees. Jeff was intent on his mission of painting each one of her toenails a bright red.

“Heh, baby brother, anytime I can give you a ride to the mall, you just let me know. You’re getting awfully good with these pedicures while I can’t remember the last time I had to give one to myself or pay for one.”

Jeff smiled inwardly at his sister’s observation. Their relationship was certainly unique for most siblings. As Jeff was two years younger than Amy, he was constantly asking her for favors - heck he thought it started out with his GI Joe wanting to play with her Barbie. Amy had learned very early to take advantage of Jeff and had him in servitude from a very young age. Anytime Jeff wanted anything, Amy was quick to comply, provided that the price was right. Whether it was taking out the garbage, washing the dishes, or giving pedicures, Jeff readily complied with Amy’s demands.

As Jeff concentrated on keeping the red nail polish smooth on her left big toe, he began to wonder if all this subservience had lead him to develop a particular fondness for Amy’s feet. Somehow it felt like the chicken and the egg question. Did he fantasize about her feet because he spent so much time making them look good, or was he always drawn to such fantasy which led him to pursue any opportunity to hold, touch and smell them?

Jeff was turning 15 on Friday and was contemplating his largest request yet from Amy. He had been strategizing for quite some time in how to get what he wanted without tipping his hand. What he really wanted was to feel what it would be like to be dominated by the very feet he had come to adore. What he didn’t want was to endanger his special relationship with Amy and have his sister label him as a pervert. Jeff figured that today was as good a time to give his plan a shot as any. Mom and dad were gone for the day and they had the house all to themselves. Plus he planned to use his upcoming birthday as a smoke screen for the true purpose. Swallowing hard, he began to execute his plan.

“Amy, you know how Friday’s my birthday and all, well I was wondering if I could get a big birthday wish granted before the big day.”

“Jeff, you used two bigs in one sentence. Something tells me you’re trying to use your birthday to avoid our normal exchange policy.” Amy always referred to their relationship as the exchange policy or the tribute clause. Jeff felt that tribute was more descriptive of the lopsided relationship they shared.

“Amy, you know I always pay my dues. It’s just that I want to ask you for a big favor before I turn 15.”

“OK, Jeffy, what’s the favor? We can negotiate terms after you’ve come clean.”

“Amy, I’d really like to see a girl naked before I turn 15.”

“What! Are you asking me to strip for my little brother? That’s kind of gross!”

“Come on, Amy, I’ve seen you in bikini’s and less, plus I just want to look. And you know I’m willing to pay the price.” Jeff knew this request would shock his sister. He also knew she’d be feverishly calculating the worth of this request which went far beyond a routine footrub and pedicure. He could tell Amy was struggling with this bombshell. So far the plan was working pretty well.

He planned to add a little enticement just to ensure she didn’t turn him down flat. “How about a weekly pedicure for a whole year?”

“Jeff, nice try, bucko, but I think this is a once in a lifetime shot. You need to show me how much this great honor means to you. I need something that demonstrates how important it is for you and also keeps you silent for the rest of time. This is a serious pact that can’t be broken by some cheap beer and some quick guy talk.”

“OK, Amy, I’ll tell you how much this means to me - I’ll let you kick me in the balls for the honor of seeing you naked.” This plan had worked out great. Jeff felt that he had let Amy believe that the object of his desire was to see her naked while all along he really wanted to feel helplessly in pain as a result of her kick to his balls. His so-called tribute was really his reward and he got the ultimate insurance of Amy’s silence by her nakedness - something she would never admit to a soul.

Just as Jeff was counting his good fortune, Amy cleared her throat signaling the beginning of her negotiation.

“Jeff, as much as I’m impressed by this display of your desire to see me, I’d add a little twist to the whole nature of your goal. Have you ever heard the expression, ‘I want it so bad it hurts’? Well, Jeff, I’ll accept your gracious offer of allowing me to kick your balls into next week, but I want to kick them for every piece of clothing I take off. And to show me how much this means to you, I want you to jump up after each kick and offer me yourself for more abuse. Any hesitation on your part will be construed by me as a lack of desire. What I mean is that whenever you don’t get up fast enough, the game is over, and whatever clothes remain on me will stay on me - how’s that for a sporting chance?”

Jeff couldn’t believe this. While he wanted to be kicked, he wasn’t sure how much he could take and, if he didn’t get Amy completely naked, he wasn’t so sure she wouldn’t blab this adventure to her friends or, worse yet, to mom.

“Close your mouth, Jeff; it’s impolite to go into shock in front of me.” Jeff was brought back to reality by his sister’s cold tone. What had he missed? This was a side to Amy that Jeff hadn’t seen. She accepted his outrageous offer without blinking and had turned the tables on him by upping the ante.

Jeff responded in an unsure voice, “OK, Amy it’s a deal.” He really had no choice; to back down now would accomplish nothing and just open himself up for harassment and teasing beyond compare. Now he had to get psyched because he had to get Amy naked.

“OK, Jeff, it’s a deal! No go down to the living room while I get dressed for the occasion.”

Jeff stammered quickly, “Come on Amy, you’re already dressed. Let’s go downstairs while mom and dad are still gone and get this over with.”

“Jeff, Jeff, Jeff, always in a rush. Now you know that I can’t be granting my baby brother his ultimate fantasy just dressed in shorts and a t-shirt. Besides, buddy boy, that would limit me to three kicks – not a very convincing display of desire on your part.”

Jeff’s heart sunk. Amy was fully in charge and dictating demands that he couldn’t fight. He shrugged his shoulders and headed for the living room.

“Oh, Jeff, you might as well change into those bicycle shorts of yours too. While I don’t want to see your equipment, I’ll need to know where both of them are, if you get my meaning.”

Jeff began to worry as he headed to his room. Now she wants to be able to see the outline of my balls, and who knows how many clothes she’s putting on now, he thought as he changed and headed for the living room. Pretty soon he was standing in the middle of the room, in bicycle shorts and a t-shirt waiting for Amy to show up. The heavy steps coming from the stairway confirmed his worst fear. Amy was wearing her candies. As she appeared, Jeff knew he had made a slight miscalculation. Amy was decked out in a sundress, stockings and those darned hard Candies.

“OK, Jeff, time to meet your fantasy. Did I dress up enough for you? I want to make this experience as memorable as possible for you, Baby Bro!” Her laughter sent chills through his body and he was transfixed by those staggering sandals that forecasted pain.

“Well, since the cat’s got your tongue, let’s get started, Jeff. You don’t mind if I’m kinda specific about which kicks I use, are you? I figure I might as well get some practice besides, if I don’t have variety, I’ll get bored. First, given that I’m limited by these Candies, I’ll need you to kneel down for the first kick.”

“Wait...”

“Jeff, no playey, no showey. On your knees, big boy.” Caught with nowhere to go, Jeff kneeled at Amy’s feet.

“Now lean back, Jeff, spread your legs, and keep your hands on the ground.” Thus positioned, Amy focused on her target. She noticed the big lump in his shorts, “Hmm, having some trouble distinguishing the more tender parts of your lump here, Bro. Let me help you out a little.” With that comment, Amy removed her right shoe and began to rub Jeff’s crotch with the toe of her candies. Jeff was helpless as his hardness grew. Once his manhood was erect, his twin orbs stood out clearly in his shorts.

“There they are. Such shy little balls you have. Aren’t you glad they decided to come out and play?” Jeff shivered in anticipation of what was to come. Amy was taking her time lining her first kick up.

“And here’s the windup, score!” She buried her Candie deep between Jeff’s legs. Jeff curled up in agony from her direct hit.

“Jeff, the timer’s running, stud. Take up the same position, and I’ll try it with my left shoe this time.” Amy dramatically removed her right shoe as the striptease began in earnest. Jeff slowly took his position, but his arms were shaking as he leaned back and Amy stepped between his legs.

“She’s going for the extra point, sports fans. Boom, another score!” Jeff slumped in slow motion as his body contorted in pain. Who knew something could feel so bad? Thank god the Candies were finally gone.

“Whoa, sports fans, I think that last play was a two point conversion. Well, was it Jeff, did I get both with one kick?” How could he tell? His whole lower body ached and the spasms were hell.

“A little silence from the football? Quite some progress there, Bro. Heck, I’m losing my second shoe!” With great flair, Amy swooped gracefully as she removed her left Candie and tossed it casually over her shoulder. “Come on, Jeff, the clock’s ticking, and we have so much more football to play!” Did she have to enjoy it this much?

Jeff staggered to his feet. Amy turned her back on him and began issuing new instructions. “Now, Jeff, grab me from behind like you were going to mug me or something.” As soon as his hands touched Amy’s shoulders, she yelled out a, “HIAA!” and swung her right heel viciously up between his legs. Jeff could feel the bile rise up in his throat as he slumped to the floor for the third time in as many minutes. How could he survive this when Amy was so darned motivated to flatten his nuts?

“That was great, Jeff! I could really feel your nut between my heel and your pubic bone. Man, that’s gotta hurt! Tell you what - I’ll let you pick the next article of clothing to come off.”

Jeff looked up in wonderment at his sister. His honor was to pick a piece of clothing that would only lead to his next opportunity to be blasted in the balls by his own sister.

“How about those pantyhose?” Jeff squeaked from the floor.

“Good choice, little brother. For you it will buy some time as I get them off, and, for me, it will avoid that nagging slippery feeling when I kick your nads!” Amy removed her pantyhose as Jeff tried to catch his breath and his courage.

Jeff was in a sitting position trying to get his balls to come down from his abdomen when Amy called sweetly from the couch. “Let’s try that attack from the rear one more time, Jeff. I think with a little more effort I could change your gender.” Her laughter only made Jeff more nervous. Somehow he had envisioned one lovely graceful kick and a sweet mixture of pain and pleasure as her well- manicured foot searched for his precious family jewels. The reality of her lightening quick kicks and her casual attitude removed much of the seduction he had envisioned.

“I’m ready, Jeff, no more stalling.” Jeff couldn’t help but admire her tanned legs as she stood poised and ready, so willing, so capable, so deadly. Jeff approached cautiously from behind his willing victim. As his hands again touched her shoulders, Amy elbowed Jeff lightly in the gut. As he reacted in surprise to this unexpected move, she bent forward and trapped his left leg between her hands and leaned back on the captured leg which caused him to fall on his back. Jeff was still stunned as he looked up at Amy as she held onto his ankle while looking back over her shoulder. Jeff’s eyes widened as Amy raised her right leg and flexed her foot. Jeff admired the curve of her arch as her foot accelerated into his groin. Amy kept her foot buried in Jeff’s balls as she twisted her foot back and forth. Jeff screamed in agony as she kept him impaled on her foot, twisting roughly as she searched for his tender balls. His balls slipped left and right trying to escape her onslaught.

As suddenly as it began, Amy removed her foot and gazed down at her brother. “What’s the matter, bro, foot got your balls? Don’t worry, I just thought it was appropriate that before I take off my dress, I should make this moment as memorable as possible.”

Jeff was in no position to answer. Amy’s kicks had turned his balls into black and blue piñatas, and he felt she was trying to break them open to get the candy inside. He didn’t know how could readily offer himself for more punishment. While initially exciting, he didn’t want to risk his future sex life, and yet he had to get her silence – which means he had to get her naked. Amy was in the corner taking her dress off. Her shapely form was highlighted when she pulled the sundress over her head. Clad only in bra and panties, Amy began stretching, limbering up for her next exercise.

“Oh, Jeff, it’s time old boy. Time to pay tribute to my talented toes. Tell ya what, I’ll let you pick the foot that punts your nads next. Which one, Einstein, lovely left foot or rockin’ right? What could be fairer than that?”

Hmm, maybe this is the break I’m looking for, he thought. Her left foot couldn’t be as dangerous as her right foot. Maybe I can make it after all! “OK, Amy, just for a change of pace, I’ll try the left foot this time.”

“How about a little more action, bro? Tell ya what, I’ll kick you with my left foot, and, if you can catch my foot before I kick you again, I’ll take it all off. Kind of a double or nothing bet to add some excitement to our action. Of course, if I can kick you twice before you catch my foot, the party’s over. What do you say, Jeffy?”

Jeff knew this was the break he wanted. If he could just get the “balls” for one more kick, he could have it all, the fantasy and the silence. “It’s a deal, Amy. I’ll take your best shot and catch your foot before you get that two point conversion you want so bad.”

Amy almost had to snicker out loud. What a moron, she thought. First, he thinks he can trick me into believing he really wants to see me naked and second, he thinks he can get me to actually strip for him. Amy was well aware of Jeff’s foot fetish. His attention was just too passionate whenever he gave her pedicures and footrubs. She figured this treatment was the best gift she had ever given her brother. It would be a long time before he could look at her toes and not feel some sympathy pain between his legs. She was surprised that he actually wanted to be kicked - how did these guys get so fucked up about sex? If she hadn’t read that book about fetishes, she would have had a hard time making the connection between a foot fetish and a desire to be kicked. Knowledge is power. Jeff would be quite satisfied for some time after today. How in the world will he bring up this subject in the future? She couldn’t wait to see his creativity in revisiting this issue, and how long would it take him to recover? She knew that her future of satisfying pedicures and footrubs was secure. Now, just how difficult should she make it for this wimp? Hmm, something memorable.

“OK, Jeff, for the big Kahuna, go ahead and get on your hands and knees like the dog you are!” Amy laughed and teased with some practice kicks. Jeff reacted with shock again. Damn, how did she come up with these unexpected twists at every turn? Just when he felt confident, now he was hampered by this strange position from which to defend himself. He’d have to take her first kick and then cover his nads before she could reload. Damn.

“Quit stalling, stud. Let’s rock... or rack, as the case may be. Get on down, Jeff. Time to watch the master.” As Jeff took his position on his hands and knees, Amy waited patiently and then stepped up behind him. “Lean forward a little more, Jeff. I want to give myself a sporting chance for two points. In fact you can lower your head and watch my foot say hello to your nuts.”

Jeff did as he was told. Maybe if he watched, he could anticipate her kick and catch her foot before it made contact. Yeah, this might work. He could catch her next kick without even having to get up. Amy couldn’t believe this setup. Her brother was on his hands and knees in front of her - doggie style - and waiting to be kicked. She could see the outline of his nads trapped within those bicycle shorts. How could he know they made her job so easy? Easy to see, easy to bust. Plus they held his balls within their nylon grip. No escape, no challenge. She toyed with the idea of grouping his balls closer together, heck why not?

“Wait right there, Jeff, let me arrange things for the big event.” Amy walked over to retrieve one of her sandals. As gently as a feather, she used the toe of her shoe to move his balls around. She noticed there was no hard-on resulting from this gentle touch. How long would it be before he experienced that feeling again? She might never know. Amy surveyed her work. What a masterpiece! Balls tucked together, snug as a fly within her web. Now was the time for the piece de resistance.

She backed up and measured the distance for her kick. She pointed her toes and admired her instep. What an appropriate ending to Jeff’s birthday surprise. How many hours had he spent admiring the top of her foot? Now that very object of his desire was to be the method of his destruction, or at least the means to his permanent enslavement. She took her leg back slowly and grunted with the effort of her kick. The loud slap almost echoed in the room as her foot lifted Jeff from the ground. Jeff watched the kick in exquisite detail. Amy’s instep caught his balls full-force. His soundless intake of breath testified to her effectiveness.

Before he even could return to his original position, she was cocked and ready to fire. Her second kick caught Jeff just as his knees touched the ground. The timing was perfect. The combination of his weight going down and her foot rising up sealed his doom. Her instep compressed his trapped balls and sent him flying forward to where he was face down and trying to breathe. His mumbling was incoherent and pained. He twitched in agony. He couldn’t even attempt to cover up. His brain was short circuited in pain.

By the time he regained his senses, he heard Amy walking back up the stairs, dressed and laughing. “Better luck next time, Jeff. Better get upstairs before mom and dad come home and tend to your swollen puppies. Who knows, I may want nieces and nephews some day!” Her receding laughter left Jeff alone in misery. How could he ever face her again?