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Proposal for Pussy – Session 20 – Jerking on Panty

Pete knew he was in trouble. Though he really did not know Samantha all that well, what he did know of her left no doubt being caught jerking off in her panties would entail some kind of punishment. His past indiscretion against her brought on a stormy night visit filled with humiliation, spanking, and a thrashing hand job. He knew enough of her to know she was capable of just about anything.

“I – I – I’m so sorry Samantha. I thought you were…”

“Rebecca?” Samantha interrupted him. “Looking at you now I can only assume you two have made up and made out, am I right?” she asked with a cheshire grin as she watched Pete fumble taking off her underwear.

“Um, y-yes, please, I really am sorry for this,” Pete replied blushing heavily, covering himself, and unsure whether to hand Samantha back her underwear or return it to the drawer he snatched it from.

Samantha grabbed her panties and returned them to the drawer herself. Pete just stood there anxious and naked wondering what she was going to do to him. There was a sudden coolness to her demeanor and yet that grin lie beneath the surface leading Pete to imagine some wicked concoction brewing in her head. She asked him to dress if he liked, but to have a seat in the small lounge area of the dorm room. Pete scrambled to put on his blue boxer briefs, sat on the love seat sweating in anticipation, and stared blankly at the saturday morning cartoons on the television.

Samantha sauntered over joining Pete, as ever the curvaceous sexy beast he thought her to be. He still marvelled at how much she resembled Tiffany Amber Thiesen. “Uncanny!” he thought to himself. Her black bob style haircut had grown a little longer and now had a few red streaks in it. Otherwise, she hadn’t changed much since he saw her last. He thought her dress very cosmopolitan consisting of a black blouse, red scarf, wool skirt, and knee high black leather boots. Her baby powder and roses smelling perfume helped settle Pete’s nerves a little, but not nearly as much as her hand gently stroking his thigh, her head propped up on her elbow, and a sudden warmness to her demeanor.

“Aren’t situations best when they’re win – win, Pete?” Samantha asked in a soft voice. Pete hesitated a nod, still ill at ease, feeling like he was in some kind of lion’s den. “I want to proposition you,” Samantha continued, her hand crawling further up his thigh. “You see, ever since that day you walked in on Rebecca and myself and we had our little exchange we’ve been talking about you. Rebecca felt like she needed to have a personal one-on-one confessional with you and, believe it or not, I was the one who suggested she ask you to make her the woman she felt she needed to be. She no doubt told you we’re both bisexual. We also both find you terribly cute, not to mention well endowed,” she said with a mischievous giggle bringing her hand up to within inches of Pete’s hard on.

“I know you have a girlfriend, Katrina, and from what I’ve heard of her I think you ought to feel very lucky to be with her. However,” Samantha interposed herself, shifting in her seat, and coquettishly staring up towards the ceiling, “here’s the always sticky – ethical part of the deal, if you’d like to be our little boy toy, you know, a little swingin’ something on the side for kicks, a secret tryst maybe, hmmm?

Rebecca and I have just been talking about adding a little spice to the bedroom and your name always seems to surface. At first as a joke, but then ever more seriously,” Samantha continued staring Pete in the eye, her hand now firmly grasping his cock. Pete started to form an answer, but Samantha cut him short. “You needn’t worry about saying no. There will be no hard feelings. The option is yours,” she reassured him.

“A boy toy?” Pete asked not ready to say yes, unsure about what he might be getting himself into, and removing Samantha’s hand from his penis.

“Hold the phone! Didn’t you put my step-mom’s panties on my head and make sure the picture of my girlfriend was staring back at me that night to teach me a lesson about taking responsibility for my actions. A responsibility that I have towards others that care for me and that I care for, showing me that my actions are never really wholly my own and have unforeseen consequences that can never be predicted?” Pete asked now confused.

Samantha did not respond right away. “Oh gosh no, I was just fucking with your head. Though I must say that’s a very mature conclusion, I’m impressed. Like I said, there’s always an ethical side to these sorts of affairs. Remember, this is a proposition for physical love and not romantic love. I’m sure you understand the difference between the two. So do you wanna be our little boy toy or what?” she asked with her eyebrows raised and her nose in the air.

Pete thought he understood the difference between physical and romantic love. He understood what he and his step-sister experienced the night before extended beyond mere physical love. He had undoubtedly found himself in a sticky situation. His brain told him to decline, but his hormones screamed to go for it. He knew he would never have another opportunity like the one being offered. He knew it was doing wrong by Katrina, but right by Rebecca.

“Well? I’m waiting,” Samantha reminded him. “Are you in?”

“Fuck yes!” growled Pete lunging in at her ample bosom, but Samantha pushed him away.

“Oh no, don’t think I’ve forgotten about your punishment,” chided Samantha. “Mens rea, that’s Latin for criminal intent and is meant to measure blame. Actus reus is Latin for the physical component of the crime. Together they form the indictable offence I’m charging you with.”

“Mea culpa,” Pete replied with a smirk and shrug of his shoulders.

“Clever boy, now get down on your hands and knees and crawl over to my bed. I will be acting as your judge, jury, and executioner.”

Pete did as ordered more than willing to play along. As he crawled over to her side of the dorm room Samantha followed behind him, digging her heels in the crack of his ass, pushing him forward. She demanded he stand, remove his underwear, and not move an inch. She removed her own clothing revealing a sheer black mesh bustier with gartered black stockings and black silk bikini style panties. She kept her black leather boots on, but removed the panties by detaching the hip straps. Pete peered at the sublime figure before him. His cock throbbed and ached as his eyes traced Samantha’s curves.

There again were the large conical breasts, the flaring feminine hips, and the bubble butt he remembered so well. And all of it on the creamiest skin he’d ever seen. There too was the “V” of pubic hair pointing down to pouty pussy lips and a pierced clitoris. He had forgotten about the phoenix tattoo below her navel and the rose on the small of her back. He licked his lips watching her fetch something from a drawer. She took out a pair of black satin gloves that made there way up to her elbows.

Pete began stroking himself and told Samantha she looked delicious. Samantha turned on her heels, furious.

“How dare you speak without permission!” she chastised him.

“We’ll fix that right away,” she continued and made her way to the bathroom. She returned holding a pair of white cotton panties in her hands. Sniffing the panties she confirmed they were Rebecca’s.

“Now open wide,” Samantha commanded, gagging Pete with his step-sister’s underwear. She picked up the pair of black bikinis she had just removed and stuffed them in Pete’s mouth as well. Samantha chuckled as she looked onto Pete with his cheeks puffed up full of panties and eyes wide open.

She immediately corrected her break of character scolding her captive saying how naughty boys like him ought to be seen and not heard. Samantha then rummaged through her bottom drawer and pulled out a ping pong paddle. She slapped her gloved hand with the paddle and nodded, mischief on her face. Pete instantly understood what was coming to him and gave her a look of playful dread.

Samantha sat on her bed gesturing Pete to assume the position over her lap. With his head hung, Pete bent himself over his captor’s lap making sure to stick his butt up in the air. He deliberately slipped his penis in between her thighs. He knew it was going to sting, but he wanted to get kinky and play the game as much as he wanted to please Samantha. His rock hard erection leaking precum did nothing to betray the sentiment.

Before Samantha began administering the punishment she paused and gently rubbed Pete’s ass cheeks pronouncing, “You are my captive and I your captor. It is my duty to deliver your punishment. There will be three punishments in store for your sorry ass this morning since, I believe, you committed three separate crimes.

I will not tell you what three punishments lie in store for you though I can see you’ve obviously figured out what the first will be. As for the crimes themselves you’re first charged with the invasion my personnel property. Secondly, you’re charged with the theft from the personnel property you invaded, namely, my panties. Finally, the last transgression you’re charged with this morning has to do with violating the panties you defiled as you masturbated in them. Also, it should be noted, you took my red ruffles. Nobody touches my red ruffles – NOBODY!” Samantha yelled with austere severity as she gave Pete his first wallop.

Pete jerked forward from the pain, his cry muffled by the panties, his cock thrusting between Samantha’s thighs. “Daaaaamn!” He shouted in his head with the sheets clutched in his hands. The sound of rubber slapping flesh reverberated throughout the room. Pete’s ass began glowing red and his body began to sweat. His captor ceaselessly scolded what a bad bad boy he was.

Once in a while Samantha would gently rub his buttocks with her satin gloves relieving him of the agony only to continue smacking him harder than before. Several minutes into the punishment he perked his ass up even higher in the air as if to ask for more. Samantha looked over at her captive to see him looking back with defiance in his eyes. She resumed her ministrations with renewed fervour, beating Pete’s bottom mercilessly. Deciding it was time to take the punishment up a notch, Samantha grabbed Pete’s nutsack from between his legs, tugging it, making his balls balloon in her hand. Now every time Pete lunged forward his balls stretched abnormally causing him to wince and whimper.

Pete knew he had had enough. “O.k., she’s got the bull by the horns, don’t she?” he thought to himself. He shook his head and tapped the mattress trying to yell through the panties and make his captor stop. Samantha ceased her spanking and released his scrotum.

Pulling the soggy underwear from Pete’s mouth Samantha simply asked, “Enough?” Pete slowly nodded, panting, wiping the sweat from his brow, and rubbing his swollen ass. She tossed his hand out of the way and gave him four final and brutal butt-busting blows. Without the panty gag Pete hollered out loud. The television had never been shut off and as Pete stood he heard a mutant turtle exclaim, “Cowabunga Dude!”

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