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Sissy Taylor and the Undersissies: The Before Times
Any and all feedback is highly appreciated
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Taylor shifted a little as once more, the tip of his caged cock pinching against his underwear, sending a small shock of pain through him. His shift was unconscious, and the pain was more from surprise than actual pain. This wasn’t uncommon for him. He wished that his panties weren’t in the wash, but they were and now he had to suffer through the pinches on his poor caged dick. To counteract the pain, Taylor consciously clenched down on the butt plug in his ass, enjoying the sensation of fullness in him. A small smile gracing his face as he did this for a moment longer, enjoying how full his ass was. Taylor was glad his hood was up, he was sure that he had a nice red blush on his face as he made his way around the side of Winslow. It was a bit early but there were a few people already walking into the school.
Taylor came around to the side of Winslow where a supply shed was almost right next to the school, but there was a narrow little alleyway that was big enough for people to pass through it. It was a popular spot in the winter for people that actually went outside to stay at since it was out of the way. Drug addicts likely used the spot as well to make their deals with people but that was only during lunch or after school. Most kids didn’t want to get up early to do their drug deals.
Taylor entered the small alcove and could see that Mistress Madison was already there. With an unconscious clench down on his plug, Taylor smiled as he saw his Mistress. Madison smiled in return as she saw her cute sissy boi coming into the alley. As they continued to walk towards each other, Madison reached out and cupped Taylor’s crotch, causing him to gasp and start a bit. Madison giggled at his reaction.
“How’s my cute lil’ sissy boi today Hmm?” as she asked, she continued to fondle Taylor, feeling up his full and blue balls as she used her other hand to pull him into a kiss with her. Taylor of course obliged. Their tongue meeting in the middle as they had a little mock battle for dominance. Taylor may be taller than Madison and might have been considered a viable top for the cute girl, but Madison was quite able to control sissy bois like him, and quickly took advantage of his weaknesses to dominate their little tongue battle. The hand that had brought him in for a kiss slid down his back, reached into his jeans, his briefs, and found the plug that was lodged in his ass. Taylor let out a gasp, and Madison’s tongue quickly stormed her sissy boi’s mouth, conquering it for herself once more. Taylor giggled in return as they pulled away before answering in kind.
“Good Mistress.”
“That’s good,” Madison said in return. Then she made a face as she felt the material of Taylor’s underwear, pouting cutely as she felt it, and pulling it so that the underwear material teased at Taylor’s plug, shifting it, and sending wondrous tingles through him as the plug pushed on his prostate.
“You’re not wearing your panties,”
“I needed to wash them, they got dirty.” Taylor responded, shamefaced.
“Okay cutie,” Madison’s other hand reached into Taylor’s pants, and Taylor felt his Mistress’ finger flick across the small slit that was left at the front of the cage. The pad of Madison’s finger slid across Taylor’s dick’s slit, feeling good as Madison did so.
“I know how it pinches you so I won’t punish you later today.”
“Thank you Mistress,” It was friday that day. That was the day that Madison would have Taylor come over so they could play some more, as well as when Taylor would finally be able to cum. Madison would tie him up, and unlock his cock, teasing it and slowly bringing him near to orgasm, before stopping, then starting again. She would play with his ass the whole time, making him feel wonderous things as she played with him, fucking his ass while she slowly stroked him to completion. Lately she’d gotten very good at keeping him from cumming, teasing his dick for over an hour before she finally let him cum. After that it would be up to Taylor if he would be locked up in his cage once more for the weekend, or if he got it put back on him then and there. Lately he had asked that Madison would put it back on right away, and they would sometimes have a bit more fun, or they would just hang out a bit, talking before Taylor went home. Today though…
“Mistress?” Taylor asked.
“Hmm?” Madison looked at him as she continued to fondle his balls, made large by his week of chastity. It felt good but he couldn’t be distracted now.
“When… when you unlock me later… could you… could you… not let me cum?” Madison at first looked surprised, before a smile broke out on her face.
“Aww, is my cute slutty little sissy wanting to be teased a bunch more hmm?” Madison started teasing the plug in Taylor’s ass some more, drawing out a small gasp from him as she did so, making sure to push the plug in him towards her so that it rubbed harder against his prostate, sending sparks of delight through him, all the while he held onto his mistress Madison a bit harder as his breath became ragged.
“Yes mistress,” Madison giggled again at how well trained her sissy was. Not that he would go against her, they both got too much out of this arrangement. Not just that but Madison knew that Taylor loved this, loved how his ass made him feel. Madison got to finally have her own cute sissy to have fun with, and be pervy with. She’d never had a friend like this before.
“I’ve got a surprise for you,” Madison told Taylor gleefully as she pulled her hand from toying with his butt plug to reach into the side pocket of her bag. She pulled away from him, giving his balls one more playful grope before she pulled a largish box.
“Is that?” Taylor asked, his eyes wide.
“It is.” Madison answered, stroking the side of the non descript box. It looked like something a watch would come in, Madison fingered at the small indent on the side of the thing, Taylor wanted to see inside of the box but he waited.
“Do you want it? If I give it to you now you’ll have to wear it the rest of the day.” Madison warned her sissy boi. Taylor thought it over a moment. He knew what was in there. It was a bigger version of his plug. He had a somewhat large metal plug in, designed specifically for long term wear. Rather than a round bottom it was more like an oval, and it bent in such a way that it rubbed against his prostate when he clenched down. The box was certainly bigger than the last one the plug in him was.
As the days in his chastity had gone on, his thinking have been changing, becoming more and more fueled by lust, with his rational mind slowly being obscured by a lustful fog that altered his actions and lowered his inhibitions. Rather than seriously consider how it would affect his learning in Winslow, Taylor could only think about the pleasure of having a bigger plug in his ass. He wanted it, no… he needed that plug.
“Yes, mistress, I… I want that plug.”
“That’s my cute little sissy,” then Madison opened up the box, and Taylor smiled. It looked just like the one that he had in his ass right now, but he could see it was larger. He reached out, and when Madison didn’t stop him, he picked it up. It was heavy, being made out of solid stainless steel. It was even heavier than the one in him, which made sense since it was larger. Taylor looked back up at his mistress and saw her pulling from her bag, a small bottle of lube.
“Wait we’re not doing it here… are we?”
“I don’t see why not.”
“But someone might see,” Madison waves her hand dismissively at that.
“No one will, no one comes back here. Besides, It should be a quick swap for your slutty ass. I bet you warmed it all up with your toys,” Taylor blushed, remembering how he spent a bit of time this morning, despite Dad being up and about, to play with his ass a bit. Dad never bothered him in his room, and he had an alarm for when he needed to get going, so he thought he might as well have some fun.
“Which one did you use this time?” Madison asked while gesturing for him to give her the butt plug. Taylor looked around once more, but saw no one. He passed her the metal plug.
“The vibrator, mistress.”
“Oh, you’ve been liking that one lately. Buzzing your little bitch button. I think one day we’re going to have to find a nice vibrating plug for you hmm?” Taylor could imagine it. A nice thick plug, sitting in his ass, pressed against his prostate. It would be large, but not enough to affect how he walked, much… Then suddenly, while in class, mistress Madison would hit a button, then suddenly it would begin to vibrate. Taylor would let out a sudden gasp as he tried his best to ignore the plug to the best of his abilities, and would begin to fail. He would be a hot mess in class as his caged cocklet leaked, powerful vibrations buzzing through him, driving him up the wall as he chewed on his pencil, something he hadn’t done since elementary, just to keep himself from moaning. He wouldn’t be able to concentrate on anything other than the vibrations buzzing his prostate.
Taylor shuddered in need and desire. God that would be amazing.
“Bend over and show me that cutie butt,” Taylor’s mistress asked, and hesitantly, Taylor complied. He didn’t see anyone else around, so it should be fine. Bending over, Taylor lowered his pants, and planted his hands on the side of the alleyway, his ass exposed to Madison. In his but, an oval shaped steel plug base was shining brightly. Taylor felt Madison start to touch the plug, but she didn’t remove it immediately. Instead, Taylor felt her being to shift it back and forth, pushing on his prostate more and more as she continued to tease his hole. He let out a small moan.
“P-please, mistress, someone will see.”
“Okay my cute lil’ sissy, just a moment,” Taylor felt Madison grip the oval shape of the curved butt plug and pull it out gently. The whole time it was coming out it was pressing against Taylor’s bitch button until it finally started to come out, causing Taylor to tremble. When it finally came out, Taylor felt his hole close immediately, and spasmed a bit, looking for something.
Then, suddenly, Taylor felt something big and cold touch his hole, and he gasped at the sensation of the cold plug. His hole closed up at that, making it feel bigger than it actually was. Madison rubbed his but and said it in a soft voice.
“Relax...” before she began to apply a bit of pressure. Taylor took a deep breath, then let it out, feeling the plug start to enter into him as he breathed out, and tried to relax his ass. The curved butt plug kept expanding his hole, bit by bit, until finally it reached it’s widest point. Taylor could feel himself getting stretched out by the massive plug. This was going to be in him the whole day. Taylor shivered at that. God that’s going to be so hot. Taylor bit his lip as it went in a bit more, then his ass was sucking it in. After it’s largest point the rest entered in rapidly, and Taylor could feel it rubbing into his prostate as it shifted into place. Taylor let out a little gasp as it went in, and his legs started to shake and quiver unconsciously. Madison giggled, and Taylor felt a finger swipe across the slit of his cage, before her hand came up to his mouth. Instantly he began to lick her fingers, tasting the somewhat sweet taste of lube mixed with pre cum on her fingers. He suckled on her fingers a moment more as she played with his ass using the plug, pushing it further into his prostate and making him feel amazing before she stopped and pulled his pants up for him. He stayed there a moment longer as he got used to the size.
“See you inside,” Mistress Madison said, and Taylor nodded as she left.
God it was big...
Any and all feedback is highly appreciated
<><><><><><><><><><><><><><><><>
Taylor shifted a little as once more, the tip of his caged cock pinching against his underwear, sending a small shock of pain through him. His shift was unconscious, and the pain was more from surprise than actual pain. This wasn’t uncommon for him. He wished that his panties weren’t in the wash, but they were and now he had to suffer through the pinches on his poor caged dick. To counteract the pain, Taylor consciously clenched down on the butt plug in his ass, enjoying the sensation of fullness in him. A small smile gracing his face as he did this for a moment longer, enjoying how full his ass was. Taylor was glad his hood was up, he was sure that he had a nice red blush on his face as he made his way around the side of Winslow. It was a bit early but there were a few people already walking into the school.
Taylor came around to the side of Winslow where a supply shed was almost right next to the school, but there was a narrow little alleyway that was big enough for people to pass through it. It was a popular spot in the winter for people that actually went outside to stay at since it was out of the way. Drug addicts likely used the spot as well to make their deals with people but that was only during lunch or after school. Most kids didn’t want to get up early to do their drug deals.
Taylor entered the small alcove and could see that Mistress Madison was already there. With an unconscious clench down on his plug, Taylor smiled as he saw his Mistress. Madison smiled in return as she saw her cute sissy boi coming into the alley. As they continued to walk towards each other, Madison reached out and cupped Taylor’s crotch, causing him to gasp and start a bit. Madison giggled at his reaction.
“How’s my cute lil’ sissy boi today Hmm?” as she asked, she continued to fondle Taylor, feeling up his full and blue balls as she used her other hand to pull him into a kiss with her. Taylor of course obliged. Their tongue meeting in the middle as they had a little mock battle for dominance. Taylor may be taller than Madison and might have been considered a viable top for the cute girl, but Madison was quite able to control sissy bois like him, and quickly took advantage of his weaknesses to dominate their little tongue battle. The hand that had brought him in for a kiss slid down his back, reached into his jeans, his briefs, and found the plug that was lodged in his ass. Taylor let out a gasp, and Madison’s tongue quickly stormed her sissy boi’s mouth, conquering it for herself once more. Taylor giggled in return as they pulled away before answering in kind.
“Good Mistress.”
“That’s good,” Madison said in return. Then she made a face as she felt the material of Taylor’s underwear, pouting cutely as she felt it, and pulling it so that the underwear material teased at Taylor’s plug, shifting it, and sending wondrous tingles through him as the plug pushed on his prostate.
“You’re not wearing your panties,”
“I needed to wash them, they got dirty.” Taylor responded, shamefaced.
“Okay cutie,” Madison’s other hand reached into Taylor’s pants, and Taylor felt his Mistress’ finger flick across the small slit that was left at the front of the cage. The pad of Madison’s finger slid across Taylor’s dick’s slit, feeling good as Madison did so.
“I know how it pinches you so I won’t punish you later today.”
“Thank you Mistress,” It was friday that day. That was the day that Madison would have Taylor come over so they could play some more, as well as when Taylor would finally be able to cum. Madison would tie him up, and unlock his cock, teasing it and slowly bringing him near to orgasm, before stopping, then starting again. She would play with his ass the whole time, making him feel wonderous things as she played with him, fucking his ass while she slowly stroked him to completion. Lately she’d gotten very good at keeping him from cumming, teasing his dick for over an hour before she finally let him cum. After that it would be up to Taylor if he would be locked up in his cage once more for the weekend, or if he got it put back on him then and there. Lately he had asked that Madison would put it back on right away, and they would sometimes have a bit more fun, or they would just hang out a bit, talking before Taylor went home. Today though…
“Mistress?” Taylor asked.
“Hmm?” Madison looked at him as she continued to fondle his balls, made large by his week of chastity. It felt good but he couldn’t be distracted now.
“When… when you unlock me later… could you… could you… not let me cum?” Madison at first looked surprised, before a smile broke out on her face.
“Aww, is my cute slutty little sissy wanting to be teased a bunch more hmm?” Madison started teasing the plug in Taylor’s ass some more, drawing out a small gasp from him as she did so, making sure to push the plug in him towards her so that it rubbed harder against his prostate, sending sparks of delight through him, all the while he held onto his mistress Madison a bit harder as his breath became ragged.
“Yes mistress,” Madison giggled again at how well trained her sissy was. Not that he would go against her, they both got too much out of this arrangement. Not just that but Madison knew that Taylor loved this, loved how his ass made him feel. Madison got to finally have her own cute sissy to have fun with, and be pervy with. She’d never had a friend like this before.
“I’ve got a surprise for you,” Madison told Taylor gleefully as she pulled her hand from toying with his butt plug to reach into the side pocket of her bag. She pulled away from him, giving his balls one more playful grope before she pulled a largish box.
“Is that?” Taylor asked, his eyes wide.
“It is.” Madison answered, stroking the side of the non descript box. It looked like something a watch would come in, Madison fingered at the small indent on the side of the thing, Taylor wanted to see inside of the box but he waited.
“Do you want it? If I give it to you now you’ll have to wear it the rest of the day.” Madison warned her sissy boi. Taylor thought it over a moment. He knew what was in there. It was a bigger version of his plug. He had a somewhat large metal plug in, designed specifically for long term wear. Rather than a round bottom it was more like an oval, and it bent in such a way that it rubbed against his prostate when he clenched down. The box was certainly bigger than the last one the plug in him was.
As the days in his chastity had gone on, his thinking have been changing, becoming more and more fueled by lust, with his rational mind slowly being obscured by a lustful fog that altered his actions and lowered his inhibitions. Rather than seriously consider how it would affect his learning in Winslow, Taylor could only think about the pleasure of having a bigger plug in his ass. He wanted it, no… he needed that plug.
“Yes, mistress, I… I want that plug.”
“That’s my cute little sissy,” then Madison opened up the box, and Taylor smiled. It looked just like the one that he had in his ass right now, but he could see it was larger. He reached out, and when Madison didn’t stop him, he picked it up. It was heavy, being made out of solid stainless steel. It was even heavier than the one in him, which made sense since it was larger. Taylor looked back up at his mistress and saw her pulling from her bag, a small bottle of lube.
“Wait we’re not doing it here… are we?”
“I don’t see why not.”
“But someone might see,” Madison waves her hand dismissively at that.
“No one will, no one comes back here. Besides, It should be a quick swap for your slutty ass. I bet you warmed it all up with your toys,” Taylor blushed, remembering how he spent a bit of time this morning, despite Dad being up and about, to play with his ass a bit. Dad never bothered him in his room, and he had an alarm for when he needed to get going, so he thought he might as well have some fun.
“Which one did you use this time?” Madison asked while gesturing for him to give her the butt plug. Taylor looked around once more, but saw no one. He passed her the metal plug.
“The vibrator, mistress.”
“Oh, you’ve been liking that one lately. Buzzing your little bitch button. I think one day we’re going to have to find a nice vibrating plug for you hmm?” Taylor could imagine it. A nice thick plug, sitting in his ass, pressed against his prostate. It would be large, but not enough to affect how he walked, much… Then suddenly, while in class, mistress Madison would hit a button, then suddenly it would begin to vibrate. Taylor would let out a sudden gasp as he tried his best to ignore the plug to the best of his abilities, and would begin to fail. He would be a hot mess in class as his caged cocklet leaked, powerful vibrations buzzing through him, driving him up the wall as he chewed on his pencil, something he hadn’t done since elementary, just to keep himself from moaning. He wouldn’t be able to concentrate on anything other than the vibrations buzzing his prostate.
Taylor shuddered in need and desire. God that would be amazing.
“Bend over and show me that cutie butt,” Taylor’s mistress asked, and hesitantly, Taylor complied. He didn’t see anyone else around, so it should be fine. Bending over, Taylor lowered his pants, and planted his hands on the side of the alleyway, his ass exposed to Madison. In his but, an oval shaped steel plug base was shining brightly. Taylor felt Madison start to touch the plug, but she didn’t remove it immediately. Instead, Taylor felt her being to shift it back and forth, pushing on his prostate more and more as she continued to tease his hole. He let out a small moan.
“P-please, mistress, someone will see.”
“Okay my cute lil’ sissy, just a moment,” Taylor felt Madison grip the oval shape of the curved butt plug and pull it out gently. The whole time it was coming out it was pressing against Taylor’s bitch button until it finally started to come out, causing Taylor to tremble. When it finally came out, Taylor felt his hole close immediately, and spasmed a bit, looking for something.
Then, suddenly, Taylor felt something big and cold touch his hole, and he gasped at the sensation of the cold plug. His hole closed up at that, making it feel bigger than it actually was. Madison rubbed his but and said it in a soft voice.
“Relax...” before she began to apply a bit of pressure. Taylor took a deep breath, then let it out, feeling the plug start to enter into him as he breathed out, and tried to relax his ass. The curved butt plug kept expanding his hole, bit by bit, until finally it reached it’s widest point. Taylor could feel himself getting stretched out by the massive plug. This was going to be in him the whole day. Taylor shivered at that. God that’s going to be so hot. Taylor bit his lip as it went in a bit more, then his ass was sucking it in. After it’s largest point the rest entered in rapidly, and Taylor could feel it rubbing into his prostate as it shifted into place. Taylor let out a little gasp as it went in, and his legs started to shake and quiver unconsciously. Madison giggled, and Taylor felt a finger swipe across the slit of his cage, before her hand came up to his mouth. Instantly he began to lick her fingers, tasting the somewhat sweet taste of lube mixed with pre cum on her fingers. He suckled on her fingers a moment more as she played with his ass using the plug, pushing it further into his prostate and making him feel amazing before she stopped and pulled his pants up for him. He stayed there a moment longer as he got used to the size.
“See you inside,” Mistress Madison said, and Taylor nodded as she left.
God it was big...
