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Keith's Transformation Ch 3 [M30s/F30s][Femdom][Pegging][Crossdressing][Chastity]
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HayzWrites is in chastity
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A few more weeks had passed since the start of their exploration, and Keith was enjoying himself more each scene. Outside of the scenes, their lives continued normally, but when Jasmine came to collect him in her black leather and heels, his mind melted. She had a way of sending him fully into submission with just her appearance and first commands. She would come fetch him with her realistic dick bobbing in front of her, a leash in her hand, and use him like a toy until he was begging to cum for her.

He was expecting more of the same when she left a few minutes ago to prepare for him. She came to collect him in her normal manner, though he was surprised to see she wasn’t wearing her strap-on this time. She led him by the leash to the bedroom, happy she no longer even had to command him to dress in the outfit she left for him on the bed.

His outfit this time was simple. A sheer black teddy and matching frilly panties. He quickly stripped out of his clothes and pulled on the lingerie, his dick twitching and starting to come to attention at the caress of the silk panties. Once dressed, Jasmine laid him on his back on the bed and slowly circled the bed, stopping at each corner to fasten a cuff around his wrists and ankles. His cock was now straining against the front of the panties, a small wet spot already beginning to form.

Jasmine chuckled as she ran her fingers lightly over the panty clad hard-on. “This wont do at all.” He shuddered at her touch. “Girls like you aren’t supposed to have big cocks like this, are they? Wait here.” She turned and strode from the room, leaving him laying on the bed, her words tumbling in his head.

She returned holding something, but he couldn’t raise his head enough to see what it was, all he could see was her wicked grin as she approached the bed. Without warning, she pressed a piece of ice against his dick. He thrashed against the cold, pulling ineffectively against his bonds. Soon his hard throbbing dick was soft and small again, bits of water from the melting ice running down his crotch.

He felt her pull the panties to the side, then felt hard plastic being worked around his balls and the base of his dick. With that piece in place, she fed his soft dick into a hard plastic tube, pushing it down until it connected into the base. With a click, she fastened a small padlock. She had put him in a chastity cage he didn’t even know she bought. “Now we don’t have to worry about you being a bad girl and getting hard.” She taunted merrily. “Isn’t that better?” he groaned, her words making his cock fight against the hard plastic, stopping him from growing. She held up a hand mirror so he could see the hot pink plastic encasing his cock before pulling the panties back into place, now barely disturbed by his small bulge.

She rummaged through their toys for a minute before returning holding a gag. One side had a short but thick, realistically molded dick, the other sporting a much larger dildo. As she lowered the gag towards his face, he dutifully opened his mouth without thinking. The dildo filled his mouth to the point just before being uncomfortable, and his tongue absent-mindedly swirled around the dick head. Finally, she slid a fluffy pink blindfold over his eyes, leaving him gagged and in darkness. There was a pause as she stripped, then he felt her climb onto the bed near his head.

She straddled his face and he felt the gag push in deeper as she lined up the tip of the external dildo and lowered herself onto it. She moaned softly as it slid into her, the dildo in his mouth pushing against the back of his throat as she pushed down on the gag. Slowly she started to ride his face, moaning softly as she bounced on the toy. Her thrusts making the dildo in his mouth thrust back and forth as well.

As she rode his face, Keith was struggling against his bonds. He wanted to grab her ass, her tits, play with clit, but his arms were firmly trapped by the cuffs. Blindfolded and bound, all he could do was lay beneath her. Her increasing moans were driving him wild. He could smell her arousal this close to his face, knowing her juices were covering the dildo she rode. His cock twitched and strained against the chastity cage. He was completely helpless as she used him like he was a toy.

It only took a few minutes of riding before she was moaning uncontrollably and he felt her legs starting to tense and grip the sides of his head. She slammed down on the dildo and held herself there, her moan trailing off into a gasp as her body shook. He laid underneath hear, the dildo pressed into the back of his throat, nearly making him gag as she rode out her orgasm on his face. Panting, she raised herself off the dildo and sat on the bed next to him.

“Good girl, for that I think you deserve a reward don’t you?” She taunted. He nodded, raising his head to try and look down at his locked dick. She noticed his gaze and laughed “Ohhh no sweety, we’re going to teach you to cum like a good girl.”

He wasn’t left wondering what she meant for long as she got up to grab their magic wand. He felt her sit back on the bed next to him and heard the powerful vibrator spring to life. He gasped into the gag and his body jump when she placed the head of the vibrator against his caged cock head. She held it firmly against the underside of his cock head, the vibrations making him struggle harder against the plastic cage. He was surprised to feel the pleasure starting to build, even as his cock was forced to stay soft in its prison.

Jasmine snaked a hand under his lingerie, fingers finding his nipple and giving it a firm pinch, making his back arch off the bed. She giggled and kept up her assault pinching, teasing, and flicking. Keith squirmed under her touch, fighting against his bonds as the assault pushed him closer to the edge. His final moan was muffled by the gag as his caged cock twitched and pumped his cum into the panties. Jasmine left the vibrator on his head for a few more torturous seconds before leaving him to sag back onto the bed, coming down from his orgasm.

She quickly undid the bonds on his wrists and ankles and removed the gag and blindfold, cradling him gently as he came back to himself from subspace and whispering praise. “You’re such a good girl for me. I’m so proud of you.”

As he came back to himself, he sat up and looked down at his crotch, cock still contained by the bright pink plastic. She followed his gaze, then looked at him with an evil smile.

“I know our games usually don’t go outside of the bedroom, but…” She started. “It’s really hot thinking of you being my good girl under your clothes. Would you wear it longer for me? Just until your surprise next weekend? Please?”

His mind started racing with a thousand thoughts, but as soon as he looked into her pleading eyes, he knew his decision was already made.

He nodded.

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7 months ago