Connor Smith had just gotten back home after his first year at college. He had no particular love for his home, his father had passed years prior, so it was only him, his bitch of a step-mother and his step-sister living in his old childhood home. There was one thing he did love about the old house: his neighbour, Vanessa Jackson.
Vanessa had moved in to the house next door when Connor was a teenager and she soon became a major part of his, let's say, development. Vanessa lived alone in the house, supposedly after divorcing her husband and taking him for all he was worth. A 5'8 yoga bunny in her mid-thirties, always wearing a brightly colored yoga bra with matching yoga pants, contrasting with her dark coffee skin. Connor would watch, almost drooling, as she would jog around the block, heavy breasts heaving with each step, threatening to break free of her top, but never quite making the leap. Her solo yoga routines in her backyard were a favorite of Connor's, watching her toned body twist and contort in ways that didn't seem possible drove him up the wall. He was almost certain she was doing it for his own benefit.
His favorite place to watch her was somehting her was not proud of. There was an old oak tree that was in between his house and Vanessa's. If a person were to climb half way up this tree and inch forward on it's longest branch, then that person would have an unimpeded view into Vanessa Jackson's shower. And despite some inital moral qualms, Connor made this climb quite often in his high school days. He loved the way the water made her entire body glimmer and shine, as she would dance around the shower, rubbing all the intimate areas he constantly dreamed of touching. It had been almost a year since Connor had such a view, and it was certainly one of the things on his bucketlist for the summer.
Connor had gotten to know Vanessa's schedule very well, she would always start the morning with Yoga, then a run, and then it was showtime. Watching through his window he saw Vanessa end her run and enter her house. That was his cue. He scurried down the steps in his house, luckily his step mother and step sister were out for the day, probably on another expensive shopping trip using his father's money. He went out the back door and towards the side of his house where the giant tree still stood. He made the climb many times before and had become an expert at scurrying his scrawny 5'10 body up the tree. He had gotten to the familiar branch just in time to see Vanessa peel off her sweaty workout clothes and enter the shower.
Vanessa was pushing forty now, if not already there, but she still had it, the water came down, through her short, blown out afro, over those voluptious double Ds, then guttered in between her slight 6 pack. Connor observes that she might have even gotten more toned and muscular during his time at college. Probably just for me he thinks to himself, rubbing his thighs against the tree branch.
Vanessa stops her deep scrubbing for a moment to peer outside her window. Connor recedes a bit on the branch, putting his head down and eyes off the beautiful woman for the moment. "Did she see me?" he thinks to himself? He relaxes himself, he thinks it unlikely due to the leafy coverage which the branch provides. He lifts his head up to find that Vanessa is no longer in view of the window.
"Where did she go" Connor mumbles under his breath, as he scoots further up on the branch, hoping to get a better look. He still didn't see her, so her scooted up a bit more, knowing she couldn't have gone to far.
*SNAP*
Connor gasps as the branch detaches from the trunk and he falls. It seems like an eternity before he hits the ground, he thinks about how maybe the freshman 15 he gained at college was just too mutch for the old branch, and about how he's going to have to book it to get out of the yard before Vanessa catches him and how... Connor's head slams off the dirt and grass.
Connor's vision goes blurry, as he sees a figure appear out of the corner of his eye. He turns to see the almost ghostly image of Vanessa Jackson in nothing but blindingly white bathrobe, slowly strutting towards his limp body from her house.
"Well, well" smirks Vanessa, "What do we have here?"
It's the last thing Connor remembers until his vision fades to black.
Connor is woken by the spray of ice cold water on his back. He jerks to consciousness, vision still blurry, he tries to take in his surroundings. He appears to be staring at the wall of some sort of tiled room or stall. Wait, it's a shower, and he feels naked! He tries to move his hands but finds they're securely fastened above his head head. With sudden clarity everything rushes back.
"Wakey wakey!" a cheerful yet husky voice exclaims behind him.
A manicured ebony hand grasps his shoulder and gently turns around Connor's almost dangling body. He's met with a sight that should have been horrifying if it hadden't been so hot.
It was Vanessa, she was smiling too sweetly, holding the shower spray nozel stretched out from the stall. Still in her white bathrobe, it was loosely tied around her waist, allowing for a massive amount of cleavage, and thought he might even be able to see a nipple if he craned his neck. She blasts him again with the cold spray, this time directly in his face. This really wakes Connor up as he's able to fully assess his situation. He's standnig in Vanessa's shower, a location he knows all too well, arms stretched aboe his head, handcuffed to the shower head pipes and buck naked to boot.
"What the hell is going on?" he gets out groggily.
"I think I should be asking you that same question honey!" she tilts her head in mock interest, keeping her bright smile. "What were you doing in that tree?"
"Well, I mean I was..." Connor stammered.
"Picking leaves?"
"No, well..."
"Bird watching?"
"Well, kinda..."
"Or was your pervy ass trying to get a good view of me in the shower?" Her smile and bright demeanor fade in an instant, terrifying Connor.
"I saw an injured baby bird is all and..." Connor's lie is interrupted as Vanessa unleashes an extended water spray, this time in his private parts which are incredibly sensative to the freezing cold water.
"Ahh, stop, stop! Please! Fuck you!"
Vanessa cocks her hips, holding the spray nozzel like a cowgirl and her pistol.
"Watch your language young man, or we'll have to clean your mouth out." She responds almost mockingly. "So are we ready to tell the truth now?"
Connor hesttates for a second, "Yeah ok, I may have accidentally seen you in the shower when I was doing my every day, completely normal tree climbing! I'm an outdoorsy guy!
Vanessa looks his naked, skinny and pale body up and down unbelievingly.
"Sugar I don't think you've been outdoors or climbing anything anytime recently"
Connor, more than a little ticked off from this remark starts to get angry. "Ok so what I saw you in the shower? It's your own damned fault showering with the window open like that! Plus the way you're always doing yoga and running around, dressed like a fucking stripper! You know exactly what you're doing!"
Vanessa listens on to Connor's feudal tirade with disinterest, swinging the spray nozel in her hand. Seeing this course of action wasn't getting him anywhere, he tries to switch tactics.
"But hey, I mean you should be flattered, I basically risked my fucking life to see you naked. So really you should be grateful that I'd even do that for you! Please Vanessa, I'm sorry, it was a one time thing an it won't happen again, just let me go, I promise I won't tell anyone about this. Please."
Vanessa slowly and menacingly walks towards her strung up captive, her chest stops mere inches from his and she reaches past him to return the spray nozzel to it's rightful place on the side of the shower, her cotton wrapped breasts merely kissing his skinny hairless chest. Connor thought for a moment that his plan had worked. Then Vanessa shift her face to be right in front of his and cocks her head with a devious, yet serious grin.
"Three things baby. Number one: I don't dress the way I do, or do anything I do for the benefit of disgusting perverts like you. Number two: I know this wasn't a one time thing."
Connor looks up in surprise.
"You see me and your step mama have gotten real close since you left for college, and she told me all about how you sneak out of the house to watch me when you think no one else notices. Which is why we came up with a little plan, we weakened that branch we knew you perved on, so if you came back, up to your old habits, we'd be able to catch you in the act."
This got Connor pissed " You crazy bitch! You could have gotten me killed! Do you have any idea how..."
Connor's tirade is cut short as Vanessa shoves a bar of soap, retrieved from the shower, into Connor's screaming mouth.
"I told you to stop swearing!"
Vanessa keeps her hand clamped over Connor's mouth as she pushes the soap further back until it's wedged into his cheeks and muffled gagging sounds come from Connor's mouth.
"And number three: it's not Vanessa to you, it's Miss Jackson. Understood?"
Connor, tasting nothing but soap and smelling Miss Jackon's sweet aroma, hurridly nodded yes.
Miss Jackon backed up from the young adult, taking her hand from his mouth, but the soap stayed put.
She crosses her arms in front of her lossley held cleavage "I'm going to go make some preparations for your punishment"
"Mhmm, mummifment?" Connor gets out through his gag. Has he not been punished enough he thinks.
Miss Jackon ignores the remark. "You will stay here, you will not try and escape, you will not make a sound and most importantly you will keep that soap in your mouth. Is that understood?"
Connor nods and muffles a yes.
Miss Jackons steps closer, pressing her breasts fully against Connor's chest which pushes him back, he looks down into the depth of her squished cleavage.
Miss Jackson takes his chin and lifts his eyes to meet hers. "If I find that soap on the floor when I get back I'm shoving it back in, but up the other end."
Connor's fear must have been well written on his face as she gives a light chuckle at his reaction and gives him a almost motherly like pat on his cheek as she turns around. She struts away, still chuckling, not turning around to see the scared college kid hanging in her shower like a piece of meat.
I'm Sorry Miss Jackson (F/M, F+/M)
I'm Sorry Miss Jackson (F/M, F+/M)
Last edited by bw7098 3 weeks ago, edited 1 time in total.
Welcome to the League of TuGs Writers.
They all say boxer shorts are cool,
but little Speedos always rule.
but little Speedos always rule.
-
charliesmith
- Centennial Club
- Posts: 332
- Joined: 6 years ago
That was a hot start and I loved reading it. Hope to read more of your work 
Please feel free to read and comment your thoughts.
My ongoing stories:
Roadtrip of Dreams (M/F) Chapter 14 Added.
My ongoing stories:
Roadtrip of Dreams (M/F) Chapter 14 Added.
She should tie him up and gag him with her dirty panties! 
-
milagros317
- Centennial Club
- Posts: 209
- Joined: 5 years ago
- Location: New York City
I hope that Miss Jackson gets his stepmother and stepsister to join in punishing him.
Thats a nice start, cant wait for the next chapter
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Escapee4520
- Forum Contributer
- Posts: 27
- Joined: 3 years ago
That is awesome! Cannot wait for the continuation!
Great start looking forward to more punishment! 
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dillonmichael080
- Forum Contributer
- Posts: 16
- Joined: 1 year ago
Love this set up! Can't wait to read more!
Pt II
Connor lost track of how long he was left handcuffed, hangning in the shower, but he reckons it was close to an hour by the time Miss Jackson finally returned. No longer wearing her bathrobe, she was now clad in a aqua blue low-cut sports bra with matching biker shorts. Connor's mouth would have dropped if it wasnt for the bar of soap still jammed in his mouth. The soap had gotten ever so smaller over its time in his mouth as more and more of it was washed away by his saliva either out of his mouth onto his chin, or directly down his throat. Connor's eyes scanned his captor's body, gliding over her perfectly round breasts, ever so slightly compressed and lifted by her top, down to her toned abs and her cocked hips and her...
"I just know you're not oggling me again after the conversation we just had." Miss Jackson scolds, crossing her arms.
Connor snaps out of his trance. "Mhhhm, mhhm!" her denies wide eyed, shaking his panicked.
"That's what I thought" she says strutting forward slowly until she's within arms reach of her captive. Connor ever so slightly flinches back as the handcuffs slightly clinked along the shower head, preventing him from retreating any further. She glances into his mouth.
"So have you learned your lesson about swearing?"
Connor nods his head slowly in fear and defeat, "Mmmhm".
"Good boy" She coos and light taps his cheek. "I'm going to remove the soap now and if I hear you cuss again then I'm shoving two bars in, is that understood?"
Connor nods meekly again. Miss Jackson smiles almost sweetly as she reaches two fingers in and slides the soap out of Connor's mouth. The once pristine bar now had teeth marks all over it.
"Oof, you really went to town on this one didn't you?" She holds the bar with just two fingers, in disgust as she tosses it into the trash. "Did you like the taste? A mix of soap and my post workout pit sweat?" She laughs as the disgust dawns on Connors face and he tries to spit out the checmical taste of the soap.
"Please Miss Jackon, I'm so sorry, it won't happen again, you'll never see me anymore and I won't tell anyone this happened and..."
Connor's desparate pleas are sushed by Miss Jackon's index finger going to his lips.
"Shh, shh, shh, honey, honey. It's ok, don't waste your breath. Just relaaaax, relax" Miss Jackson puts on a mask of sympathy. "The only thing talking can do is make it worse for you."
"But..."
Miss Jackson pushes her finger harder against Connor's lips as he face grows hard again. "No buts. You are mine now. Everything that happens to you from this day forward happens because I allow it. Miss Jackson removes her finger from Connor's lips, reaches both hands over shoulders almost as a lover would seeking a kiss. "Do you know how many ways I can kill you right now?"
Connor's eyes widen and Miss Jackson smirks and looks deeply, unfeelingly into his eyes.
"I could just leave you up here forever, no food, no water, I wonder how long you'd last? A week? A month? No, you don't look like you're in good enough shape to last that long" Miss Jackson drops her arms from the man's shoulders, steps into the shower and starts slowly circling him like prey, her eyes never unlocking with his. "Or maybe I draw us up a nice bath, I tie you hand and foot, and I hold you under for as long as it takes. Hell, I probably won't even need to restrain you, I doubt you'll be able to overpower me and save yourself." Miss Jackson flexes with one arm while squeezing her captive's boney bicep with her other. Miss Jackson makes it to Connor's backside and suddenly put him in a chokehold. "Or maybe I just choke you out? Simple and effective. I have a black belt in jiu-jitsu you know, don't think it would be my first time choking someone out"
She then releases the hold and steps out of the shower as Connor gasps for air. "Do you understand now?" she asks, cocking her head to the side. Connor nods frantically with tears in his eyes.
"Good! Lucky for you I'm not the type of woman to actually do any of those things. You see I'm more of the thought that humiliation is a much more fitting punishment for men like you. Would you agree?"
Connor nods his head again frantically, just thankful to be escaping death.
"Oh, so happy you feel that way!" She says with mocked excitemet, Miss Jackson's constant mood swings between a peppy cheerleader and a cold assassin only made her that much more terrifying. "Let's hope you don't change your mind when you find out what I have planned for you."
"What do you have planned for me?" Connor asks timidly.
"So eager! You'll know soon enough, but first we need to get you dressed!"
Connor was somewhat relieved to hear this as he hated being nude in front of people for a variety of reasons.
"Unfortunately your clothes are still pretty dirty after that fall you took, so I'll have to grab you something from my wardrobe."
"From your wardrobe?" Connor says confused.
"Yeah! Don't worry you're going to love it!" Miss Jackson turns to leave. "Don't go anywhere!" she says with a smile and a wink.
She obviously already had an outfit picked out as she was back in less than a minute, holding out the outfit she picked out for Connor.
"So what do you think!" She beams with a giggle.
Connor was horrified as he stared at the tiny bright pink sports bra and volleyball shorts which she held out in front of her.
Miss Jackon smiles at his horror "I remember I wore these once to a barbecue at your house and you kept staring and staring so I figured you must really like the outfit!"
"No, that's not why I..., that's not what..." Connor tries to explain.
Miss Jackson tilts her head in mock confusion. "Well, why weere you staring then if you didn't love the outfit?" Her face hardness again, sending a clear threat to Connor to be careful of what he says next.
"It's because..." Connor sighs in defeat. "No you're right, I love the outfit."
Miss Jackson beams again. "Oh wonderful! I knew you'd love it! Let's get you dressed then." The captor approaches her captive.
"I don't think it'll even fit on me though" says Connor, desperately trying to get out of his punishment.
"Don't worry hun, it's a stretchy fabric." Says Miss Jackson, kneeling down start on the booty shorts.
With a couple of heaves, she was able to get the tiny pink shorts up over the man's thighs, and with a couple more, up around his waist. She was right that the pants were stretchy, but were still pretty painful as they cut into his waist and things to the point where Connor was worried for his own blood flow. The worst was how they ran up between his butcheek and compressed his dick to a painful degree.
"You're lucky you're not packing more down here," she laughs as she lightly taps with crotch. "Or else it might be unformfotable for you."
Connor groans in humiliation.
Miss Jackson stand back up to full height. "Ok, so I'm going to uncuff you for the top. No funny business ok? Remember the jiu-jitsu thing."
Connor nods solemnly. "I understand"
"Good boy" Miss Jackson then reaches into her bra and pulls out a small key that must have been stuffed between the meat of her bosom and the tight aqua blue fabric. She then gets on her tip toes to reach one of the cuffs around Connors wrist. Her breasts press against Connor's upper chest as he stares deeply into her cleavage as it shifts and jiggles with her attempts to unlock the cuff. Connor is so entranced he doesn't even notice that his right wrist has been freed.
Miss Jackson steps back. "Ok, arms forward"
Connor complies and she slides the pink sports bra over his arms, maneuvering a bit to get past the dangling handcuffs still attached to his left wrist. She then pulls the top down hard over his shoulders, stretching it as fae as it can go which wasn't too far, just barely past his own breasts. What's worse was that the bra was pushing his pecs up into cleavage which was greatly uncomfortable and humiliating.
"Looking good babe!" Miss Jackson laughs as she reclamps the handcuff on his right wrist, rendering his hand bound behind his back.
All Connor can do was look down at his feet, trying to avoid looking into the mirror and catching a glimpse of his muiliated form. Miss Jackson notices this and grabs his chin and lifts his head to look into the mirror.
"OMG you look so good!" She continues to hold his head steady as he tries to pull his head away. "Aww, don't be shy, your tits and ass look great! Not as great as mine," she laughs, posing in the mirror. "But hey, not everyone is as naturally gifted as I am" She laughs and lets his head drop. "You know what, since we both look so hot, let's go show ourselves off, let's go for a run around the town!"
Connor's eyes shoot up to meet hers. He whines, "No please, Miss Jackson! No one can see me like this."
"Oh nonsense! What's the point of look this good if we don't show it off! After all that's why we dress like this right? To show it off and flaunt our goods to the people of this town?"
Connor looks down at the ground in defeat, knowing now that he can't refuse his captor.
Suddenly the door bell rings.
"That must be our running partners!" Miss Jackson beams.
"Running partners?" Asks Connor confused as he is hastily pushed out of the room and is led down the stairs to the foyer of Miss Jackson's house. Through the translucent glass of the front door Connor could make out the silhouette of two women waiting at the door. Miss Jackson leaves her new wrokout buddy at the stairs as she goes and answers the door.
Connor's heart drops as he hears a familiar voice. "Heyyy girl! So what's this surprise you told me about?"
"Come on in girlie! You're going to love this!
Miss Jackson steps out of the way to reveal the last two people Conner wants to see right now. His face turns a bright red as his step-mom and step-sister both enter the house and burst out laughing.
Top
Connor lost track of how long he was left handcuffed, hangning in the shower, but he reckons it was close to an hour by the time Miss Jackson finally returned. No longer wearing her bathrobe, she was now clad in a aqua blue low-cut sports bra with matching biker shorts. Connor's mouth would have dropped if it wasnt for the bar of soap still jammed in his mouth. The soap had gotten ever so smaller over its time in his mouth as more and more of it was washed away by his saliva either out of his mouth onto his chin, or directly down his throat. Connor's eyes scanned his captor's body, gliding over her perfectly round breasts, ever so slightly compressed and lifted by her top, down to her toned abs and her cocked hips and her...
"I just know you're not oggling me again after the conversation we just had." Miss Jackson scolds, crossing her arms.
Connor snaps out of his trance. "Mhhhm, mhhm!" her denies wide eyed, shaking his panicked.
"That's what I thought" she says strutting forward slowly until she's within arms reach of her captive. Connor ever so slightly flinches back as the handcuffs slightly clinked along the shower head, preventing him from retreating any further. She glances into his mouth.
"So have you learned your lesson about swearing?"
Connor nods his head slowly in fear and defeat, "Mmmhm".
"Good boy" She coos and light taps his cheek. "I'm going to remove the soap now and if I hear you cuss again then I'm shoving two bars in, is that understood?"
Connor nods meekly again. Miss Jackson smiles almost sweetly as she reaches two fingers in and slides the soap out of Connor's mouth. The once pristine bar now had teeth marks all over it.
"Oof, you really went to town on this one didn't you?" She holds the bar with just two fingers, in disgust as she tosses it into the trash. "Did you like the taste? A mix of soap and my post workout pit sweat?" She laughs as the disgust dawns on Connors face and he tries to spit out the checmical taste of the soap.
"Please Miss Jackon, I'm so sorry, it won't happen again, you'll never see me anymore and I won't tell anyone this happened and..."
Connor's desparate pleas are sushed by Miss Jackon's index finger going to his lips.
"Shh, shh, shh, honey, honey. It's ok, don't waste your breath. Just relaaaax, relax" Miss Jackson puts on a mask of sympathy. "The only thing talking can do is make it worse for you."
"But..."
Miss Jackson pushes her finger harder against Connor's lips as he face grows hard again. "No buts. You are mine now. Everything that happens to you from this day forward happens because I allow it. Miss Jackson removes her finger from Connor's lips, reaches both hands over shoulders almost as a lover would seeking a kiss. "Do you know how many ways I can kill you right now?"
Connor's eyes widen and Miss Jackson smirks and looks deeply, unfeelingly into his eyes.
"I could just leave you up here forever, no food, no water, I wonder how long you'd last? A week? A month? No, you don't look like you're in good enough shape to last that long" Miss Jackson drops her arms from the man's shoulders, steps into the shower and starts slowly circling him like prey, her eyes never unlocking with his. "Or maybe I draw us up a nice bath, I tie you hand and foot, and I hold you under for as long as it takes. Hell, I probably won't even need to restrain you, I doubt you'll be able to overpower me and save yourself." Miss Jackson flexes with one arm while squeezing her captive's boney bicep with her other. Miss Jackson makes it to Connor's backside and suddenly put him in a chokehold. "Or maybe I just choke you out? Simple and effective. I have a black belt in jiu-jitsu you know, don't think it would be my first time choking someone out"
She then releases the hold and steps out of the shower as Connor gasps for air. "Do you understand now?" she asks, cocking her head to the side. Connor nods frantically with tears in his eyes.
"Good! Lucky for you I'm not the type of woman to actually do any of those things. You see I'm more of the thought that humiliation is a much more fitting punishment for men like you. Would you agree?"
Connor nods his head again frantically, just thankful to be escaping death.
"Oh, so happy you feel that way!" She says with mocked excitemet, Miss Jackson's constant mood swings between a peppy cheerleader and a cold assassin only made her that much more terrifying. "Let's hope you don't change your mind when you find out what I have planned for you."
"What do you have planned for me?" Connor asks timidly.
"So eager! You'll know soon enough, but first we need to get you dressed!"
Connor was somewhat relieved to hear this as he hated being nude in front of people for a variety of reasons.
"Unfortunately your clothes are still pretty dirty after that fall you took, so I'll have to grab you something from my wardrobe."
"From your wardrobe?" Connor says confused.
"Yeah! Don't worry you're going to love it!" Miss Jackson turns to leave. "Don't go anywhere!" she says with a smile and a wink.
She obviously already had an outfit picked out as she was back in less than a minute, holding out the outfit she picked out for Connor.
"So what do you think!" She beams with a giggle.
Connor was horrified as he stared at the tiny bright pink sports bra and volleyball shorts which she held out in front of her.
Miss Jackon smiles at his horror "I remember I wore these once to a barbecue at your house and you kept staring and staring so I figured you must really like the outfit!"
"No, that's not why I..., that's not what..." Connor tries to explain.
Miss Jackson tilts her head in mock confusion. "Well, why weere you staring then if you didn't love the outfit?" Her face hardness again, sending a clear threat to Connor to be careful of what he says next.
"It's because..." Connor sighs in defeat. "No you're right, I love the outfit."
Miss Jackson beams again. "Oh wonderful! I knew you'd love it! Let's get you dressed then." The captor approaches her captive.
"I don't think it'll even fit on me though" says Connor, desperately trying to get out of his punishment.
"Don't worry hun, it's a stretchy fabric." Says Miss Jackson, kneeling down start on the booty shorts.
With a couple of heaves, she was able to get the tiny pink shorts up over the man's thighs, and with a couple more, up around his waist. She was right that the pants were stretchy, but were still pretty painful as they cut into his waist and things to the point where Connor was worried for his own blood flow. The worst was how they ran up between his butcheek and compressed his dick to a painful degree.
"You're lucky you're not packing more down here," she laughs as she lightly taps with crotch. "Or else it might be unformfotable for you."
Connor groans in humiliation.
Miss Jackson stand back up to full height. "Ok, so I'm going to uncuff you for the top. No funny business ok? Remember the jiu-jitsu thing."
Connor nods solemnly. "I understand"
"Good boy" Miss Jackson then reaches into her bra and pulls out a small key that must have been stuffed between the meat of her bosom and the tight aqua blue fabric. She then gets on her tip toes to reach one of the cuffs around Connors wrist. Her breasts press against Connor's upper chest as he stares deeply into her cleavage as it shifts and jiggles with her attempts to unlock the cuff. Connor is so entranced he doesn't even notice that his right wrist has been freed.
Miss Jackson steps back. "Ok, arms forward"
Connor complies and she slides the pink sports bra over his arms, maneuvering a bit to get past the dangling handcuffs still attached to his left wrist. She then pulls the top down hard over his shoulders, stretching it as fae as it can go which wasn't too far, just barely past his own breasts. What's worse was that the bra was pushing his pecs up into cleavage which was greatly uncomfortable and humiliating.
"Looking good babe!" Miss Jackson laughs as she reclamps the handcuff on his right wrist, rendering his hand bound behind his back.
All Connor can do was look down at his feet, trying to avoid looking into the mirror and catching a glimpse of his muiliated form. Miss Jackson notices this and grabs his chin and lifts his head to look into the mirror.
"OMG you look so good!" She continues to hold his head steady as he tries to pull his head away. "Aww, don't be shy, your tits and ass look great! Not as great as mine," she laughs, posing in the mirror. "But hey, not everyone is as naturally gifted as I am" She laughs and lets his head drop. "You know what, since we both look so hot, let's go show ourselves off, let's go for a run around the town!"
Connor's eyes shoot up to meet hers. He whines, "No please, Miss Jackson! No one can see me like this."
"Oh nonsense! What's the point of look this good if we don't show it off! After all that's why we dress like this right? To show it off and flaunt our goods to the people of this town?"
Connor looks down at the ground in defeat, knowing now that he can't refuse his captor.
Suddenly the door bell rings.
"That must be our running partners!" Miss Jackson beams.
"Running partners?" Asks Connor confused as he is hastily pushed out of the room and is led down the stairs to the foyer of Miss Jackson's house. Through the translucent glass of the front door Connor could make out the silhouette of two women waiting at the door. Miss Jackson leaves her new wrokout buddy at the stairs as she goes and answers the door.
Connor's heart drops as he hears a familiar voice. "Heyyy girl! So what's this surprise you told me about?"
"Come on in girlie! You're going to love this!
Miss Jackson steps out of the way to reveal the last two people Conner wants to see right now. His face turns a bright red as his step-mom and step-sister both enter the house and burst out laughing.
Top
Pt. III
Miss Jackson's house was filled with laughter. Not Connor's of course, instead it was the mocking laughter of his step-mother Sharon, his step-sister Kaylee and of course that of his sadistic captor and neighbor Miss Vanessa Jackson.
"OMG! Look at him!" Cried Kaylee in utter disbelief, running up to the handcuffed Connor, bright blonde ponytail bouncing behind her. "Eww, I think I can almost see his shrimp dick!" She giggles as she flicks the mound in his pink volleyball shorts. She was a tiny thing, barely standing five feet tall, but what she lacked in height she more than made up for in muscle. She had a clearly defined six pack which was framed perfectly by her electric blue sports bra and matching yoga pants.
"Hey back off!" Connor tries to shuffle away only collide into the rock hard body of Miss Jackson who holds him steady in place by his arm.
"Easy baby, be polite to my guest," she whispers in his ear. Leaving unspoken that if he didn't behave himself he would regret it dearly.
Sharon closes the front door and makes her way towards her handcuffed and humilated step-son, a sinister grin on her face as she flips her blonde pixie cut. She's wearing a tight grey sports bra under an unzipped matching grey tracksuit with tight grey trackpants covering the rest of her 5'4" frame. While her body definitely wasn't as toned as Miss Jackson's, but she was definitely in good shape for a woman in her late 40s. Her outfit revealed pale white, vein streaked cleavage which Connor couldn't help but stare into as they approached his restrained form.
"My, my." she smiles, assessing Connor's situation. "Looks like someone got themselves in a bit of trouble."
The three women laugh while Connor keeps his head bowed in shame.
"Let me guess Vanessa" Sharon says already knowing that her guess was correct. "The pervert tried to spy on you on the old branch again, and he fell into our little trap?"
Vanessa opens her mouth in mock surprise. "How did you figure it out?!"
"Men are just so predictable!" says Sharon shaking her head in mock dissapointment.
"Mhmm, sing it sister"
"Well looks like someone's grounded for the rest of the summer" says Sharon stearnly.
"Oooh, that sucks bro" says Kaylee in mock sympathy placing her hand on Connor's shoulder. He shakes it off as she giggles.
Connor and Kaylee had never gotten along despite being the same age. She and the rest of the cheerleading team would constantly tease and bully him at school, one time even leaving him tied up with duct tape in a locker over night. When his principal Ms. Kim found him she laughed uncontrollably and took pictures to send to Sharon who she's pickleball partners with. And of course Kaylee got no punishment because she claimed it was just a senior prank, plus she was the golden girl so she could do no wrong.
Conner was so angry thinking about that memory that he barely noticed Miss Jackson tying a length of rope around his exposed midriff.
"What's this for?" Connor asks confused.
"Why it's your leash of course!" Says Miss Jackson matter of factly. "Can't have you taking off in the middle of our run can you?"
"Even if he did I'd be able to catch him for you Miss Jackson" Points out Kaylee. "He really isn't the fastest runner"
"Hell I'm probably faster than him." Says Sharon as the three girls laugh at his unathleticism.
"Even better, we can use it to pull him along so her doesn't slow us down!" Offers up Miss Jackson. "Well let's get running ladies, we're losing daylight"
"Wait, first let's take a selfie!" suggests Kaylee pulling out her phone which was tucked away in her yoga pants waitband. The three women sandwich Connor between the three of them as Kaylee forces Connor's head up to meet the camera, she sticks her tongue out as Sharon smiles and Miss Jackson flexes.
"Off we are ladies!" says Sharon as the women make their way towards the door.
Connor tries to remain planted but is pulled forward as Miss Jackson tugs on the rope tied around his waist.
"Let's go honey, you don't want to hold us up!"
"Please Miss Jackson" Connor begs as he's pulled through the door. "I'll do anything you want, just don't make me run in this, I'm not even wearing shoes!"
"Hush hush, honey. Look the faster you run, the quicker it'll go right?"
Connor drops his head and nods in defeat.
"I just love how well you've trained him Vanessa" Comments Sharon, ruffling Connor's hair. "He's like a little puppy. Maybe after this we'll keep him in a crate in the basement."
"Wait, what!" Connor's eyes widen in shock.
"Ooh, does that mean I can take his room mom?" Asks Kaylee excitedly.
"Sure you can! But first you have to beat your dear old mom in a race" At that Sharon starts running down the road.
"Hey" Kaylee follows in a hurry. "No fair, you got head start!"
"Looks like we're off baby" says Vanessa, starting to jog down the road. "Do try to keep up" She laughs as she winks to Connor who begins his barefoot jog after her.
Connor's was hurting all over. His bare feet were cut up by the sidewalk, his shoulders hurt from being kept wrenched back due to the handcuffs, his midriff had rope burn from the "leash" Miss Jackson had tied around it and both his legs were on fire from the seemingly never ending run he's on. What hurt worst of all was the humiliation. Being paraded around the town in a tight pink workout bra and panties was tantamount to hell for Connor. His smushed together breasts jiggled with every step the way a man's weren't supposed to, and his package was packed much to tightly into the volleyball shorts to the point he was worried his balls would recede into his body. And the citizens of the town only made it worse. The men all looked in in pity and horror, while the women would laugh, catcall and take pictures and videos.
"You're going to go viral bro!" Commented Kaylee with a laugh when they ran through the town center.
He lost track of how far and for how long they've been jogging but however long it was, it was too long for him. The opposite seemed to be true for his captors who were still chugging along with glee, seemingly unimpacted by the long run. The only hint that they've been running for so long was the slight glean of sweat which shined off of their skin.
Connor is suddenly tugged forward by the rope tied around his stomache.
"Hurry it up buttercup!" Calls Miss Jackson back to Connor, running backwards to look at her captive at the end of the 6 foot rope. "We're almost done!"
Connor, who was momentarily entranced by the woman's breasts which launched a few beads of sweat as they heaved with each step, gasps."Really?"
"Maybe!" Miss Jackson laughs and the 2 other women follow suit.
"I haven't been very impressed with your speed Connor" scolds Sharon. "We might need to shorten your leash."
It's true that Connot had not been able to keep up with the much more fit women. His view the entire run had been of three fit bodies consitently ahead of him. Their behinds were striding and jiggling in almost perfect unison which had a near hypnotic affect on the man who would just stare as if in a trance, his legs moving on auto pilot.
His trance was broken by a "Yoo hoo!"
Connor turns to see his old principal, Ms. Kim, who was sunbathing on her front yard in nothing but a red and white striped bikini. She waved down Sharon who waved back and and lead the group towards Ms. Kim including Connor who was mercilessly tugged along by Miss Jackson.
"Sharon, hello, out for a run?" asks Ms. Kim with a slight Chinese accent.
"You can say that" Sharon smirks back.
"And what do we have here?" says Ms. Kim, tilting her reflective sunglasses.
Connor, who was trying his best to remain hidden behind Miss Jackson's muscular form was pulled front and center right in front of the high school prinipal. Connor briefly glanced at her bikini which had small layers of fat spilling out grom the top and thong. No one ever knew her age because it seemed like she has been in her early 50s for decades. One kid in high school tried find out by snatching her wallet to get a look at her driver's license. Unfortunately for him she caught him and he wasn't in school for a whole week. When he finally returned, he was a shell of a man who didn't speak to anyone for the rest of the year.
"What did you do to deserve this punishment?" She asks sitting up in her lawn chair.
"I.." Connor starts before he was interrupted by Sharon.
"This little pervert was caught peeking into to Vanessa's shower. Isn't that right perv?"
Connor can only look down in shame.
"Tsk, tsk naughty boy" Ms. Kim shakes her head. "They used to let us punish students like this but then the government stepped in. I still have my paddle if you need it."
"Thanks for the offer Tiffany, but we should be heading back home, sun's about to go down." Says Sharon. "By the way good luck in the state finals tomorrow!"
"Luck!" Ms. Kim scoffs. "We don't need luck while I've got the other team's quarterback chained in my basement."
The women laugh as all Connor can do it think of what that poor quarterback is enduring.
"Well if you ever need any help with the peeper let me know. I'm very expereinced in curbing bad behavior" She lowers her sunglasses and winks at Connor who cringes at the thought.
"Will do! Have fun with your quarterback." Says Sharon as she turns around and starts back on the road.
Connor is yanked back on the road again, still horrified. He wasn't sure how much longer he could run, luckily he started recognizing familiar houses, meaning they were close to home.
"Almost there ladies! Push! Push!" Motivated Vanessa as they three women broke out into almost a full sprint.
Connor did all he can to match their pace, but with his hand locked behind his back he was mostly pulled the rest of the way to his house by Vanessa. Once they reached Connor and his step-family's house he collapsed on to his knees breathing heavily as the women high five each other in celebration of their run.
"Good run ladies!" Cheered Vanessa.
"I can keep going!" Says Kaylee bouncing on her toes.
"I don't think he can" Laughs Sharon, gesturing to Connor's prostrate form.
"Ugh, boys ruin everything" Groans Kaylee, giving Connor a swift kick in the ribs which drops him flat on the pavement.
The women laugh as Sharon passes around a towel which the women use to wipe off their sweat, along with a water bottle which they all drink from.
"You want some water baby?" Asks Vanessa, lifting Connor back on his knees by his handcuffs.
All Connor manage is a faint nod.
"Oh no!" says Sharon in mock surprise as Kaylee dumps the rest of the water on the ground.
"Ooops!" mocks Kaylee with a chuckle.
"No worries hon! We have more" says Miss Jackson, grabbing the sweat towel from Sharon.
Connor already knew where this was going. He watched helplessly on his knees as Miss Jackson wiped off the sweat off every inch of her body, including her slightly hairy armpit, her underboobs, and worsed of all between her butcheeks.
"Ahh, open wide" instructs Miss Jackson as Sharon holds Connor's head up.
Connor couldn't even struggle he was so drained, plus in all honestly he really needed the moisture. The stinky, sweaty, damp towel was shoved into his mouth mercilessly, filling up his cheeks. It tasted of three distinct women's sweats merged into one terrifying cocktail, but Connor was forced to suck it all down and the women laughed in disgust to see him swallow as tears welled in his eyes.
"You're so disgusting!" Laughed Kaylee filming a video to be posted on her tiktok.
"Well I think we all need a shower" Suggested Miss Jackson. "Hopefully this time mine won't be interrupted" She says accusingly at the humiliated form kneeling in front of her.
"Trust me Vanessa" assures Sharon. "He won't be bothering anyone for a long time. In fact..." Sharon kneels down and lifts Connor's head up to look at Miss Jackson. "Take one last look big boy, because you won't be seeing her or anyone else for a long time."
"Ooooh, so you are locking him in the crate in the basement!" Exclaims Kaylee excitedly.
"That's where all animals belong until they can behave themselves." Smiles Sharon.
"I think that is a wonderful idea!" Affirms Miss Jackson. "Might just be what he needs to start acting right."
Connor's eyes are welling with tears as he's hoisted up by his step-mom and step-sister who each grab one of his arms. Sharon rips the towel out of Connor's mouth.
"What do you have to say to Miss Jackson" scolds Sharon.
Colin mumbles something.
Sharon slaps the back of his head. "Louder"
"I'm sorry Miss Jackson"
"Not as sorry as you're going to be pig" Says Sharon, shoving the towel back in his mouth. She goes to turn around "Oh wait Vanessa, your cuffs and clothes."
Miss Jackson waves it off. "You can give me the cuffs next time you see me. As for the clothes, I think he should keep them." She smirks at Connor. "They make you feel sexy, don't they baby."
Connor doesn't answer as his sister starts pulling his rope towards the house. He turns around to get one last look at Miss Jackson who is waving him goodbye.
"Bye bye baby. Have a great summer!" She laughs mockingly as she shimmies her chest at him, one last torment to sear the image of her blazing hot body into his mind. A few tears run down Connor's face as he is lead inside the house and into what will be the worst summer of his life.
Miss Jackson's house was filled with laughter. Not Connor's of course, instead it was the mocking laughter of his step-mother Sharon, his step-sister Kaylee and of course that of his sadistic captor and neighbor Miss Vanessa Jackson.
"OMG! Look at him!" Cried Kaylee in utter disbelief, running up to the handcuffed Connor, bright blonde ponytail bouncing behind her. "Eww, I think I can almost see his shrimp dick!" She giggles as she flicks the mound in his pink volleyball shorts. She was a tiny thing, barely standing five feet tall, but what she lacked in height she more than made up for in muscle. She had a clearly defined six pack which was framed perfectly by her electric blue sports bra and matching yoga pants.
"Hey back off!" Connor tries to shuffle away only collide into the rock hard body of Miss Jackson who holds him steady in place by his arm.
"Easy baby, be polite to my guest," she whispers in his ear. Leaving unspoken that if he didn't behave himself he would regret it dearly.
Sharon closes the front door and makes her way towards her handcuffed and humilated step-son, a sinister grin on her face as she flips her blonde pixie cut. She's wearing a tight grey sports bra under an unzipped matching grey tracksuit with tight grey trackpants covering the rest of her 5'4" frame. While her body definitely wasn't as toned as Miss Jackson's, but she was definitely in good shape for a woman in her late 40s. Her outfit revealed pale white, vein streaked cleavage which Connor couldn't help but stare into as they approached his restrained form.
"My, my." she smiles, assessing Connor's situation. "Looks like someone got themselves in a bit of trouble."
The three women laugh while Connor keeps his head bowed in shame.
"Let me guess Vanessa" Sharon says already knowing that her guess was correct. "The pervert tried to spy on you on the old branch again, and he fell into our little trap?"
Vanessa opens her mouth in mock surprise. "How did you figure it out?!"
"Men are just so predictable!" says Sharon shaking her head in mock dissapointment.
"Mhmm, sing it sister"
"Well looks like someone's grounded for the rest of the summer" says Sharon stearnly.
"Oooh, that sucks bro" says Kaylee in mock sympathy placing her hand on Connor's shoulder. He shakes it off as she giggles.
Connor and Kaylee had never gotten along despite being the same age. She and the rest of the cheerleading team would constantly tease and bully him at school, one time even leaving him tied up with duct tape in a locker over night. When his principal Ms. Kim found him she laughed uncontrollably and took pictures to send to Sharon who she's pickleball partners with. And of course Kaylee got no punishment because she claimed it was just a senior prank, plus she was the golden girl so she could do no wrong.
Conner was so angry thinking about that memory that he barely noticed Miss Jackson tying a length of rope around his exposed midriff.
"What's this for?" Connor asks confused.
"Why it's your leash of course!" Says Miss Jackson matter of factly. "Can't have you taking off in the middle of our run can you?"
"Even if he did I'd be able to catch him for you Miss Jackson" Points out Kaylee. "He really isn't the fastest runner"
"Hell I'm probably faster than him." Says Sharon as the three girls laugh at his unathleticism.
"Even better, we can use it to pull him along so her doesn't slow us down!" Offers up Miss Jackson. "Well let's get running ladies, we're losing daylight"
"Wait, first let's take a selfie!" suggests Kaylee pulling out her phone which was tucked away in her yoga pants waitband. The three women sandwich Connor between the three of them as Kaylee forces Connor's head up to meet the camera, she sticks her tongue out as Sharon smiles and Miss Jackson flexes.
"Off we are ladies!" says Sharon as the women make their way towards the door.
Connor tries to remain planted but is pulled forward as Miss Jackson tugs on the rope tied around his waist.
"Let's go honey, you don't want to hold us up!"
"Please Miss Jackson" Connor begs as he's pulled through the door. "I'll do anything you want, just don't make me run in this, I'm not even wearing shoes!"
"Hush hush, honey. Look the faster you run, the quicker it'll go right?"
Connor drops his head and nods in defeat.
"I just love how well you've trained him Vanessa" Comments Sharon, ruffling Connor's hair. "He's like a little puppy. Maybe after this we'll keep him in a crate in the basement."
"Wait, what!" Connor's eyes widen in shock.
"Ooh, does that mean I can take his room mom?" Asks Kaylee excitedly.
"Sure you can! But first you have to beat your dear old mom in a race" At that Sharon starts running down the road.
"Hey" Kaylee follows in a hurry. "No fair, you got head start!"
"Looks like we're off baby" says Vanessa, starting to jog down the road. "Do try to keep up" She laughs as she winks to Connor who begins his barefoot jog after her.
Connor's was hurting all over. His bare feet were cut up by the sidewalk, his shoulders hurt from being kept wrenched back due to the handcuffs, his midriff had rope burn from the "leash" Miss Jackson had tied around it and both his legs were on fire from the seemingly never ending run he's on. What hurt worst of all was the humiliation. Being paraded around the town in a tight pink workout bra and panties was tantamount to hell for Connor. His smushed together breasts jiggled with every step the way a man's weren't supposed to, and his package was packed much to tightly into the volleyball shorts to the point he was worried his balls would recede into his body. And the citizens of the town only made it worse. The men all looked in in pity and horror, while the women would laugh, catcall and take pictures and videos.
"You're going to go viral bro!" Commented Kaylee with a laugh when they ran through the town center.
He lost track of how far and for how long they've been jogging but however long it was, it was too long for him. The opposite seemed to be true for his captors who were still chugging along with glee, seemingly unimpacted by the long run. The only hint that they've been running for so long was the slight glean of sweat which shined off of their skin.
Connor is suddenly tugged forward by the rope tied around his stomache.
"Hurry it up buttercup!" Calls Miss Jackson back to Connor, running backwards to look at her captive at the end of the 6 foot rope. "We're almost done!"
Connor, who was momentarily entranced by the woman's breasts which launched a few beads of sweat as they heaved with each step, gasps."Really?"
"Maybe!" Miss Jackson laughs and the 2 other women follow suit.
"I haven't been very impressed with your speed Connor" scolds Sharon. "We might need to shorten your leash."
It's true that Connot had not been able to keep up with the much more fit women. His view the entire run had been of three fit bodies consitently ahead of him. Their behinds were striding and jiggling in almost perfect unison which had a near hypnotic affect on the man who would just stare as if in a trance, his legs moving on auto pilot.
His trance was broken by a "Yoo hoo!"
Connor turns to see his old principal, Ms. Kim, who was sunbathing on her front yard in nothing but a red and white striped bikini. She waved down Sharon who waved back and and lead the group towards Ms. Kim including Connor who was mercilessly tugged along by Miss Jackson.
"Sharon, hello, out for a run?" asks Ms. Kim with a slight Chinese accent.
"You can say that" Sharon smirks back.
"And what do we have here?" says Ms. Kim, tilting her reflective sunglasses.
Connor, who was trying his best to remain hidden behind Miss Jackson's muscular form was pulled front and center right in front of the high school prinipal. Connor briefly glanced at her bikini which had small layers of fat spilling out grom the top and thong. No one ever knew her age because it seemed like she has been in her early 50s for decades. One kid in high school tried find out by snatching her wallet to get a look at her driver's license. Unfortunately for him she caught him and he wasn't in school for a whole week. When he finally returned, he was a shell of a man who didn't speak to anyone for the rest of the year.
"What did you do to deserve this punishment?" She asks sitting up in her lawn chair.
"I.." Connor starts before he was interrupted by Sharon.
"This little pervert was caught peeking into to Vanessa's shower. Isn't that right perv?"
Connor can only look down in shame.
"Tsk, tsk naughty boy" Ms. Kim shakes her head. "They used to let us punish students like this but then the government stepped in. I still have my paddle if you need it."
"Thanks for the offer Tiffany, but we should be heading back home, sun's about to go down." Says Sharon. "By the way good luck in the state finals tomorrow!"
"Luck!" Ms. Kim scoffs. "We don't need luck while I've got the other team's quarterback chained in my basement."
The women laugh as all Connor can do it think of what that poor quarterback is enduring.
"Well if you ever need any help with the peeper let me know. I'm very expereinced in curbing bad behavior" She lowers her sunglasses and winks at Connor who cringes at the thought.
"Will do! Have fun with your quarterback." Says Sharon as she turns around and starts back on the road.
Connor is yanked back on the road again, still horrified. He wasn't sure how much longer he could run, luckily he started recognizing familiar houses, meaning they were close to home.
"Almost there ladies! Push! Push!" Motivated Vanessa as they three women broke out into almost a full sprint.
Connor did all he can to match their pace, but with his hand locked behind his back he was mostly pulled the rest of the way to his house by Vanessa. Once they reached Connor and his step-family's house he collapsed on to his knees breathing heavily as the women high five each other in celebration of their run.
"Good run ladies!" Cheered Vanessa.
"I can keep going!" Says Kaylee bouncing on her toes.
"I don't think he can" Laughs Sharon, gesturing to Connor's prostrate form.
"Ugh, boys ruin everything" Groans Kaylee, giving Connor a swift kick in the ribs which drops him flat on the pavement.
The women laugh as Sharon passes around a towel which the women use to wipe off their sweat, along with a water bottle which they all drink from.
"You want some water baby?" Asks Vanessa, lifting Connor back on his knees by his handcuffs.
All Connor manage is a faint nod.
"Oh no!" says Sharon in mock surprise as Kaylee dumps the rest of the water on the ground.
"Ooops!" mocks Kaylee with a chuckle.
"No worries hon! We have more" says Miss Jackson, grabbing the sweat towel from Sharon.
Connor already knew where this was going. He watched helplessly on his knees as Miss Jackson wiped off the sweat off every inch of her body, including her slightly hairy armpit, her underboobs, and worsed of all between her butcheeks.
"Ahh, open wide" instructs Miss Jackson as Sharon holds Connor's head up.
Connor couldn't even struggle he was so drained, plus in all honestly he really needed the moisture. The stinky, sweaty, damp towel was shoved into his mouth mercilessly, filling up his cheeks. It tasted of three distinct women's sweats merged into one terrifying cocktail, but Connor was forced to suck it all down and the women laughed in disgust to see him swallow as tears welled in his eyes.
"You're so disgusting!" Laughed Kaylee filming a video to be posted on her tiktok.
"Well I think we all need a shower" Suggested Miss Jackson. "Hopefully this time mine won't be interrupted" She says accusingly at the humiliated form kneeling in front of her.
"Trust me Vanessa" assures Sharon. "He won't be bothering anyone for a long time. In fact..." Sharon kneels down and lifts Connor's head up to look at Miss Jackson. "Take one last look big boy, because you won't be seeing her or anyone else for a long time."
"Ooooh, so you are locking him in the crate in the basement!" Exclaims Kaylee excitedly.
"That's where all animals belong until they can behave themselves." Smiles Sharon.
"I think that is a wonderful idea!" Affirms Miss Jackson. "Might just be what he needs to start acting right."
Connor's eyes are welling with tears as he's hoisted up by his step-mom and step-sister who each grab one of his arms. Sharon rips the towel out of Connor's mouth.
"What do you have to say to Miss Jackson" scolds Sharon.
Colin mumbles something.
Sharon slaps the back of his head. "Louder"
"I'm sorry Miss Jackson"
"Not as sorry as you're going to be pig" Says Sharon, shoving the towel back in his mouth. She goes to turn around "Oh wait Vanessa, your cuffs and clothes."
Miss Jackson waves it off. "You can give me the cuffs next time you see me. As for the clothes, I think he should keep them." She smirks at Connor. "They make you feel sexy, don't they baby."
Connor doesn't answer as his sister starts pulling his rope towards the house. He turns around to get one last look at Miss Jackson who is waving him goodbye.
"Bye bye baby. Have a great summer!" She laughs mockingly as she shimmies her chest at him, one last torment to sear the image of her blazing hot body into his mind. A few tears run down Connor's face as he is lead inside the house and into what will be the worst summer of his life.
-
milagros317
- Centennial Club
- Posts: 209
- Joined: 5 years ago
- Location: New York City
Pt. IV
Alone in dank, lightless and unfinished basement, underneath a beautiful suburban house in a beautiful suburban neighborhood, sat a simple dog crate and inside this crate laid a broken man. Four black grated walls, covered by a black grated top, with a slightly padded bottom, it was obviously meant for a larger dog, but still not big enough for Connor to fully lay down, instead he could only fit comfortably on his knees or laying down in a fetal position. Connor had lost track of how long it had been since he had been lead down into the basement by his step-mother and step-sister who proceeded to pull out the dusty crate from the corner of the basement and shove him inside. He had been stripped naked and his hands had thankfully been released from the handcuffs and the sweat rag removed from his mouth, but all Connor could do was beg, plead and even cry for mercy as his step-mother Sharon locked the cage door with a padlock and his step-sister Kaylee took pictures and videos to send to her friends. Sharon's only response to her new prisoner's tears were a devilish smirk and "You deserve this" as she turned off the lights and ascended the stairs.
Connor had been going crazy ever since that moment. The basement had no windows so it was impossible to tell how many days were passing. The only clue to the passage of time was Sharon's daily visits, although Connor doubted they were actually daily at all, as he was sure she was skipping days to further mess with his sense of reality. Most of the time these visits consisted of Sharon, typically always dressed in a skimpy outfit of some sort, delivering some meager form of food to Connor. On good days it would be leftover scraps from the dinner table, and on bad days it would be wet dog food mixed with Sharon's own spit. Sometimes Kaylee would come down with her so they could torment him together. The sight of the bubbly blonde pissed Connor off to no end, making the torment that much worse. One time the two came down in tight sweats with a paper shredder and Connor's entire comic book collection. They proceeded to drink wine all night and laugh with each other as they fed Connor's collection straight into the shredder as he watched in horror. He screamed and shook the cage, but his malnourished body had no strength left to make a difference. The women only laughed at his anguished and clinked their wine glasses together.
Connor was reminiscing on the pain of this moment and many other like it when suddenly the door to the basement swings open and Connor can make out footsteps descending the steps. Connor hopes to himself that this will be a quick visit. His hopes are dashed when Sharon flicks on the damp lighting consisting of two dim light bulbs hanging from the ceiling. Connor's eyes take a few seconds to adjust to the light and then he gasps and retreats to as far back in his cage as he can go, which wasn't too far at all.
Before him were two figures, one was his step-mother Sharon, clad in a bright white one-piece swimsuit which looked like it was struggling to contain her breasts. Since Connor's incarceration she always had on what could only be described as an evil grin which deeply unsettled Connor. What was more unsettling in that moment was her companion. A body he knew unfortunatley well. Although she was only 5'8", from this angle she seemed a giantess to the laid low man. Her coffee colored breasts were wrapped in a gold string bikini with black accents. Each cup covering maybe half of each breast with the rest spilling out in voloptous cleavage. Connor's eyes followed down her defined abs to her pelvis which was wrapped in a short sarong coverup.
"Hi baby" drawls Miss Jackson with a bright and wide grin as the two women peer through the top of the crate directly at Connor.
Connor can only manage a whimper in response as he gazes up towards his cruel godesses in abject horror.
Miss Jackson chuckles. "You really did a number on him Sharon"
"Well there was a lot of work to be done."
"Preach, sister." responds Miss Jackson looking Connor right in the eye. "Has he seen the sun since our run?"
Sharon thinks for a second "Oh, come to think of it no." This draws a laugh from both of the women.
"How has his behavior been?"
"Definitely improved" notes Sharon. "As you can see he is pretty well domesticated and rarely makes a fuss anymore."
"Do you think he'll be ready before he has to go back to college?"
"It doesn't matter, I contacted my old sorority and they ensured me they would be taking over for his training while he's off at college."
This was devastating news to Connor who had hoped leaving for college would allow him to escape this hell. He was familiar with his step-mother's old sorority, Beta Delta Sigma Mu was the terror of his campus. If you were a man walking on campus too long after dark, it wouldn't be uncommon to be snatched up a couple of co-eds looking for fun. It was an incredibly exclusive sorority which required each new member to kidnap a member of the faculty and present them to the sorority. The rumor was that Sharon kidnapped the president of the entire university as part of her initiation and the blackmail they got on him and the school kept the sorority well funded and immune from any legal actions for as long they pleased.
*Ding dong*
"Excuse me Vanessa, I have to get the door" Says Sharon making her way to and up the steps. "Remember to turn off the lights when you come back up."
"I'll be up in a second" says Miss Jackson grinning deviously at Connor and crouching down on her toes to get to Connor's level, this pushed her breasts together which Connor couldn't help but stare at.
"Tsk, tsk" scolds Miss Jackson. "You have 5 seconds to stop staring at my tits or else I'll have to call your step-momma back down and find out how she punishes you."
Connor's eyes snap up to meet Miss Jackson's almost immediately.
"That's better. I know baby, it's hard when I'm wearing this" She presses her breasts together and gives them a slight shake as Connor does everything in his power not to look down. "I didn't wear this just to tempt you by the way. Your mom is having a pool party upstairs with some of the local ladies."
Connor's eyes ever so slightly tilt up to look at the ceiling.
"Oooh, does that get you excited honey? A bunch of middle aged lounging women in bikinis? Perhaps I should tell Sharon her training isn't working like she thought."
Connor quickly shakes his head in denial as he relocks his dread filled eyes with her.
Miss Jackson just laughs and stands up. "That's what I thought. Well I'm going to go back to the party. Just wanted to say goodbye since you'll be going back to college next week."
Connor looks up in surprise.
"Oops, spoilers. I know Sharon doesn't want you to know what day it is. But I'm nicer than her aren't I?"
Connor instinctively agrees even though in his head he couldn't decide who was worse.
"Aww, you're so sweet" Miss Jackson puffs her bottom lip in faint humility. "Speaking of, I talked to Sharon and we both agreed that it would be fun if you stayed at my place when you come back for Winter break. My cage is so much nicer than hers, it's actuall built for a human! Plus I'll even let you go upstairs! How does that sound?"
It actually sounded pretty good to Connor who gave a gracious head nod.
"I mean, don't get me wrong you will be my slave, but I think you'll like it better, don't you?"
Connor wasn't sure and didn't respond, keeping his head down.
"Well later baby cakes" says Miss Jackson blowing a kiss to Connor. She then turns off the lights. "See you soon!" This was both a promise and a threat which lingered with Connor as she ascended the stairs and shut the door behind her, once again plunging the broken man into inescapable darkness and defeat.
Alone in dank, lightless and unfinished basement, underneath a beautiful suburban house in a beautiful suburban neighborhood, sat a simple dog crate and inside this crate laid a broken man. Four black grated walls, covered by a black grated top, with a slightly padded bottom, it was obviously meant for a larger dog, but still not big enough for Connor to fully lay down, instead he could only fit comfortably on his knees or laying down in a fetal position. Connor had lost track of how long it had been since he had been lead down into the basement by his step-mother and step-sister who proceeded to pull out the dusty crate from the corner of the basement and shove him inside. He had been stripped naked and his hands had thankfully been released from the handcuffs and the sweat rag removed from his mouth, but all Connor could do was beg, plead and even cry for mercy as his step-mother Sharon locked the cage door with a padlock and his step-sister Kaylee took pictures and videos to send to her friends. Sharon's only response to her new prisoner's tears were a devilish smirk and "You deserve this" as she turned off the lights and ascended the stairs.
Connor had been going crazy ever since that moment. The basement had no windows so it was impossible to tell how many days were passing. The only clue to the passage of time was Sharon's daily visits, although Connor doubted they were actually daily at all, as he was sure she was skipping days to further mess with his sense of reality. Most of the time these visits consisted of Sharon, typically always dressed in a skimpy outfit of some sort, delivering some meager form of food to Connor. On good days it would be leftover scraps from the dinner table, and on bad days it would be wet dog food mixed with Sharon's own spit. Sometimes Kaylee would come down with her so they could torment him together. The sight of the bubbly blonde pissed Connor off to no end, making the torment that much worse. One time the two came down in tight sweats with a paper shredder and Connor's entire comic book collection. They proceeded to drink wine all night and laugh with each other as they fed Connor's collection straight into the shredder as he watched in horror. He screamed and shook the cage, but his malnourished body had no strength left to make a difference. The women only laughed at his anguished and clinked their wine glasses together.
Connor was reminiscing on the pain of this moment and many other like it when suddenly the door to the basement swings open and Connor can make out footsteps descending the steps. Connor hopes to himself that this will be a quick visit. His hopes are dashed when Sharon flicks on the damp lighting consisting of two dim light bulbs hanging from the ceiling. Connor's eyes take a few seconds to adjust to the light and then he gasps and retreats to as far back in his cage as he can go, which wasn't too far at all.
Before him were two figures, one was his step-mother Sharon, clad in a bright white one-piece swimsuit which looked like it was struggling to contain her breasts. Since Connor's incarceration she always had on what could only be described as an evil grin which deeply unsettled Connor. What was more unsettling in that moment was her companion. A body he knew unfortunatley well. Although she was only 5'8", from this angle she seemed a giantess to the laid low man. Her coffee colored breasts were wrapped in a gold string bikini with black accents. Each cup covering maybe half of each breast with the rest spilling out in voloptous cleavage. Connor's eyes followed down her defined abs to her pelvis which was wrapped in a short sarong coverup.
"Hi baby" drawls Miss Jackson with a bright and wide grin as the two women peer through the top of the crate directly at Connor.
Connor can only manage a whimper in response as he gazes up towards his cruel godesses in abject horror.
Miss Jackson chuckles. "You really did a number on him Sharon"
"Well there was a lot of work to be done."
"Preach, sister." responds Miss Jackson looking Connor right in the eye. "Has he seen the sun since our run?"
Sharon thinks for a second "Oh, come to think of it no." This draws a laugh from both of the women.
"How has his behavior been?"
"Definitely improved" notes Sharon. "As you can see he is pretty well domesticated and rarely makes a fuss anymore."
"Do you think he'll be ready before he has to go back to college?"
"It doesn't matter, I contacted my old sorority and they ensured me they would be taking over for his training while he's off at college."
This was devastating news to Connor who had hoped leaving for college would allow him to escape this hell. He was familiar with his step-mother's old sorority, Beta Delta Sigma Mu was the terror of his campus. If you were a man walking on campus too long after dark, it wouldn't be uncommon to be snatched up a couple of co-eds looking for fun. It was an incredibly exclusive sorority which required each new member to kidnap a member of the faculty and present them to the sorority. The rumor was that Sharon kidnapped the president of the entire university as part of her initiation and the blackmail they got on him and the school kept the sorority well funded and immune from any legal actions for as long they pleased.
*Ding dong*
"Excuse me Vanessa, I have to get the door" Says Sharon making her way to and up the steps. "Remember to turn off the lights when you come back up."
"I'll be up in a second" says Miss Jackson grinning deviously at Connor and crouching down on her toes to get to Connor's level, this pushed her breasts together which Connor couldn't help but stare at.
"Tsk, tsk" scolds Miss Jackson. "You have 5 seconds to stop staring at my tits or else I'll have to call your step-momma back down and find out how she punishes you."
Connor's eyes snap up to meet Miss Jackson's almost immediately.
"That's better. I know baby, it's hard when I'm wearing this" She presses her breasts together and gives them a slight shake as Connor does everything in his power not to look down. "I didn't wear this just to tempt you by the way. Your mom is having a pool party upstairs with some of the local ladies."
Connor's eyes ever so slightly tilt up to look at the ceiling.
"Oooh, does that get you excited honey? A bunch of middle aged lounging women in bikinis? Perhaps I should tell Sharon her training isn't working like she thought."
Connor quickly shakes his head in denial as he relocks his dread filled eyes with her.
Miss Jackson just laughs and stands up. "That's what I thought. Well I'm going to go back to the party. Just wanted to say goodbye since you'll be going back to college next week."
Connor looks up in surprise.
"Oops, spoilers. I know Sharon doesn't want you to know what day it is. But I'm nicer than her aren't I?"
Connor instinctively agrees even though in his head he couldn't decide who was worse.
"Aww, you're so sweet" Miss Jackson puffs her bottom lip in faint humility. "Speaking of, I talked to Sharon and we both agreed that it would be fun if you stayed at my place when you come back for Winter break. My cage is so much nicer than hers, it's actuall built for a human! Plus I'll even let you go upstairs! How does that sound?"
It actually sounded pretty good to Connor who gave a gracious head nod.
"I mean, don't get me wrong you will be my slave, but I think you'll like it better, don't you?"
Connor wasn't sure and didn't respond, keeping his head down.
"Well later baby cakes" says Miss Jackson blowing a kiss to Connor. She then turns off the lights. "See you soon!" This was both a promise and a threat which lingered with Connor as she ascended the stairs and shut the door behind her, once again plunging the broken man into inescapable darkness and defeat.
great chapters
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Scottstud94
- Centennial Club
- Posts: 187
- Joined: 6 years ago
- Location: Michigan
I’m excited to see Connor in his place. The basement must be pretty quiet since they didn’t gag him, but curious how he’ll fare at college as a sorority slave?