Mistress Kristy and Jack, her sissy slave (2)

Mistress Kristy and Jack, her new sissy (1)

The moon cast a pale glow over the soft sand, illuminating the gentle ripples as they caressed the shore. A cool breeze danced across the beach, teasing the fine strands of hair that clung to Mistress Kristy’s body. She stood there, tall and elegant, her emerald eyes sparkling in the dim light.

Beside her, Jack knelt on the sand, his small frame trembling with anticipation and fear. He was dressed in nothing but a tiny button chastity, lace panties, and a pair of black leather boots that clicked against the sand with each anxious step he took.

The air was thick with their shared desire, the tension between them palpable as they prepared for what was to come.

Lost of Jack’s virginity tonight

Kristy reached down, her long, pale fingers curling around the hard length that strained against the confines of Jack’s chastity.

• “Are you ready for me, Jack?” she purred, her voice a low, sultry murmur in his ear.

He moaned, his body shuddering in response.

• “Please, Mistress,” he begged, his voice barely more than a whisper. “Take it off. Please.”

But Mistress Kristy only smiled, her emerald eyes sparkling with mischief. She pulled his chastity just hard enough to send a sharp stab of pain through his groin, making him whimper in agony and pleasure.

• “Not yet,” she teased, “I want you to feel every inch of me inside you.”

And with that, she guided his head back, exposing his throat, her other hand reaching down between their
bodies.

She positioned herself, the head of her strap-on pressing against his opening, and then, with a firm, steady pressure, she began to push inside. Jack arched his back, crying out in pain and desire as she forced her way past the barrier of his virginity.

Inch by agonizing inch, she drove herself deeper, until finally, with a sharp thrust, she was buried to the hilt.

• “There,” she breathed, her body trembling against his. “That’s how you take it.”

Kristy leaned forward, her breasts pressing against Jack’s chest, her lips finding his’ in a deep, passionate kiss. His body adjusted to the foreign intrusion, the stretching pain giving way to a strange, intoxicating fullness.

Just all about Mistress Kristy’s pleasure tonight

He wrapped his arms around her, clinging to her as she began to move, her hips undulating in a sensuous rhythm that drove the strap-on deep within him. Each thrust sent waves of pleasure coursing through his body, and each time she withdrew, the loss was almost unbearable.

• “You’re so tight,” she murmured against his ear. “It’s all about my pleasure tonight, Jack. My getting off with these thrusts that rub my clit against you.”

She increased the pace, her movements growing more urgent. The sound of their breath mingling, the slapping of flesh against flesh filled the night air. Jack’s head fell back, his eyes closed, his mouth open in a silent scream of ecstasy as the sensations overwhelmed him.

But even as he lost himself in the throes of passion, he couldn’t help but feel a twinge of jealousy. It wasn’t fair that she got to enjoy this pleasure while he was left out, trapped inside his own body. He longed to be the one giving her this release, to feel her body pressed against his, her cries of pleasure filling the air. But for now, he would have to content himself with being her willing and eager slave, taking her pleasure as she saw fit.

Kristy’s thrusts became more frenzied, her movements jerking him back and forth like a ragdoll.
The friction against his prostate sent waves of pleasure coursing through his body, making it impossible to think of anything but the overwhelming sensations. He could feel her orgasm building, her muscles tensing around him, and with a final, forceful thrust, she cried out in ecstasy, her body shuddering against his.

The arrival of Chloé, a good friend of Mistress Kristy

As she came down from her peak, she leaned forward, her breath hot against his ear.

• “That was for you, Jack,” she whispered, her voice hoarse with desire. “That was for being such a good
  boy, taking my rubber cock like a champ.”

She pulled out of him, withdrawing the strap-on with a wet, sucking sound. Jack collapsed onto the sand, panting heavily, his entire body trembling from the release.

Kristy knelt beside him, gently running her fingers through his hair.

• “Are you okay?” she asked, her voice soft and concerned.

He looked up at her, his emerald eyes shining in the moonlight.

• “I just wish I could give you that,” he whispered. “I wish I could make you feel that way.”

She smiled, leaning forward to press her lips against his.

• “Don’t worry, Jack. There will be other times. And until then, you’re all mine.”

She nodded towards the woman who had joined them.

• “This is Chloe. She’s a good friend of mine, and she’s going to help us make sure you’re taken care of.”

Chloe knelt beside them, her eyes fixed on Jack’s exposed crotch.

• “So, Jack,” she purred, her voice low and sultry. “You’re really committed to this, huh?”

She reached out and gently caressed his exposed button, her fingertips grazing over the sensitive skin.

• “It’s so hard and firm. I bet it feels good to have it out like this.”

Jack felt a shiver run down his spine as Chloe’s touch sent waves of pleasure coursing through his body. He nodded, unable to speak past the lump in his throat.

• “It’s… it’s been like this for a long time,” he managed to croak out.

Touched and caressed by Chloe

Mistress Kristy smiled, her expression both amused and slightly wistful.

• “I know what you mean, Jack. I remember when I was first locked up.”

She reached over and traced a finger along the length of his shaft, eliciting a gasp from him.

• “It’s amazing how much power they have over us, isn’t it? How they can make us feel so helpless and yet so desired at the same time.”

Chloe leaned forward, her breath hot against his ear.

• “You’re doing so well, Jack. I bet you’re just aching to feel that sweet release, aren’t you?”

She slipped her hand between his legs, rubbing his button in slow, circular motions.

• “Tell me how badly you want it.”

Jack closed his eyes, the sensations too intense to bear.

• “God, I… I need it,” he groaned. “I just need… to cum.”

His hips bucked involuntarily against Chloe’s hand, seeking release.

• “Please, just let me…”

Kristy chuckled, her fingers dancing across his chest.

• “But you’re not supposed to cum, Jack. Remember?”

She leaned forward, her lips brushing against his ear.

• “You’re a sissy, and sissies don’t cum unless they’re given permission. Unless they’re lucky enough to be with someone who cares about them enough to give them that release.”

She paused, her voice dropping to a husky whisper.

• “And you are so lucky, Jack. You have me, and Chloe, and all the other girls here who want to take care of you.”

Now, the new little pet of Mistress Kristy and her friend

Chloe moved closer, her body pressed against his.

• “That’s right, Jack. You’re our little pet now, and we’re going to make sure you’re always taken care of. Always satisfied.”

She traced a finger along his aching shaft, teasing him mercilessly.

• “But you have to be a good boy, Jack. You have to listen to Mistress Kristy and do what she says.”

Kristy smiled down at him, her expression both stern and loving.

• “Now, Jack. Do you want me to help you cum?”

She reached into her pocket and produced a small, silver vibrator.

• “Or would you rather just watch Chloe have some fun?”

Chloe blushed, but she didn’t object. Instead, she knelt between Jack’s legs, her body grinding against his chastity device. She moaned as she felt his hardness pressed against her, and she could see the desire in his eyes as he watched her.

As Chloe ground against him, Mistress Kristy positioned the vibrator at the juncture of her thighs. She turned it on, and it buzzed to life, the vibrations sending waves of pleasure through her body.

Then, with a sultry smile, she placed the vibrator against Chloe’s pussy, making their skin touch.

• “There we go, Chloe. We’re sharing this together. Just like we share Jack.”

Just a sex toy for these two friends

Jack’s head was spinning. The sensations were overwhelming. He could feel the vibrations against his skin, and the wet heat of Chloe’s body against his chest. So, he tried to focus on what was happening, but all he could think about was how much he wanted to cum. He wanted to feel that release, wanted to feel like a man again.

• “Please,” he managed to gasp out. “Please let me cum.”

Then, he felt a surge of wetness against his lips as Chloe’s hips bucked against him, and he knew she was close. He moved his head, trying to lick her, to taste her, but she was just out of reach.

• “Let me taste you,” he begged. “Please, Chloe.”

Chloe paused, her breath coming in ragged gasps. She looked down at Jack, her eyes filled
with desire and something else – something almost like pity.

“Oh, Jack,” she whispered. “You’re so beautiful when you beg.”

Then, with one swift movement, she lowered herself onto his face, taking his mouth in a deep, passionate kiss as her orgasm washed over them both.

Kristy watched them, a small smile playing at the corners of her lips. She knew Jack was close. So close. And she wanted to see him lose control, wanted to see him surrender to his desires.

With a gentle push, she guided Chloe’s hips, forcing her to grind harder against Jack’s chest. The friction against Jack’s trapped cock was almost unbearable, and with a groan of surrender, he erupted, spraying his cum across Chloe’s hairy shaved pussy.

Feeling a growing sense of excitement and anticipation

As he came, Chloe collapsed onto his chest, her breath coming in ragged gasps.

• “Oh, Jack,” she murmured, her fingers tangled in his hair. “You did so well.”

Kristy leaned forward, her lips brushing against his ear.

• “Now,” she whispered, “you’re going to make sure Chloe is nice and clean for me, aren’t you?”

She felt the shiver that ran through Jack’s body at her words.

Jack didn’t need to be told twice. He lapped at Chloe’s juices, tasting the mix of their bodies and his own cum. He felt Chloe’s fingers gently stroking his hair, guiding him as he licked and sucked.

As he worked, he glanced up at Kristy, who was watching them with a satisfied smile.

• “That’s it, Jack,” she purred. “Make sure she’s nice and clean for me. I’ve been looking forward
  to this all day.”

She reached down and fondled his hair, then traced a finger along his chin, collecting the last of his cum. With a wicked grin, she brought the finger to his lips and forced her fingers into Jack’s mouth.
Jack opened his mouth, letting out a small moan as he tasted his own cum mixed with Chloe’s juices. He felt Kristy’s other hand gently stroke his cheek, guiding him as he licked and sucked on her finger. His body was still trembling from the release, but he couldn’t help but feel a growing sense of excitement and anticipation.