Dr. Kaufman, a dentist and Jack’s friend from college was intrigued by her patient’s presence.
Jack, a man who had come in for a routine dental visit, was dressed unusually. He wore a conservative button-down shirt, slacks, and a pair of women’s panties. The lace and delicate fabric of the undergarment were a stark contrast to the masculine clothing he wore on top.
Dr. Kaufman couldn’t help but wonder why her male patient would be wearing women’s panties. As she finished up with another patient, she called Jack into her office to discuss the matter further.
Jack’s fantasy: Being dressed like a woman
She gestured for him to sit down in the plush leather chair, and then took a seat herself across from him.
- “Jack, I’ve known you for years, and I’ve never seen you wear anything like this before. Can you tell me why you’re wearing these panties?”
Her voice was calm, yet curious.
Jack shifted uncomfortably in his seat.
- “I-I don’t know, Doctor. It’s just something I started doing recently… I don’t really know why.”
He averted his gaze, unable to meet her eyes.
Dr. Kaufman raised an eyebrow, clearly not buying his explanation.
- “Jack, I’m your friend, and I’m here to help. Why don’t you tell me the truth? Is there something going on in your life that you’re not comfortable sharing with me?”
She leaned in closer, studying his face for any sign of discomfort or guilt.
Jack took a deep breath and let it out slowly.
- “Well, you see… I’ve been having these fantasies. About being dressed up like a woman. I didn’t know why at first, but I’ve been enjoying them more and more. And I thought, maybe if I started wearing these panties, it would help me… you know, explore that side of myself.”
He looked at her pleadingly, hoping she wouldn’t judge him.
A dentist by day and Dominatrix at night
Dr. Kaufman considered his confession for a moment. She had known Jack as a strong, confident man. But hearing him admit to these desires made her heart race a little faster. She took a chance and decided to reveal a secret of her own.
- “Jack, I understand what you’re going through. You see, I’m not just a dentist by day. At night, I’m a dominatrix. I’ve always had a thing for sissy boys who want to explore their feminine side.”
Her words seemed to pierce through Jack’s defenses. He felt a mixture of shock and arousal
course through his veins.
- “You’re a dominatrix?” he managed to whisper. “And you’re into… this kind of thing?”
Dr. Kaufman smiled seductively.
- “Oh, yes, Jack. I’m very much into it. And I think I can help you explore your desires. Why don’t you let me take care of you tonight? I promise it’ll be an experience you’ll never forget.”
Jack’s heart raced in his chest as he considered her offer. He had never even considered being with a woman, much less a dominatrix. But something about the way this dominatrix was talking to him, the way she made him feel… it was intoxicating.
- “What do you mean, take care of me?” he asked, his voice barely above a whisper.
Naked in front of this gorgeous dominatrix
Dr. Kaufman stood up from her chair and walked around the desk, her heels clicking on the floor. She kneeled down in front of him, her eyes boring into his.
- “I mean, Jack, that I can help you explore your feminine side. I can teach you what it means to be a sissy slut. And tonight, I’m going to show you just how good it feels to be milked in chastity using my strap-on.”
Her words sent a shiver down Jack’s spine. He couldn’t believe he was even considering this.
But the thought of being with her, of giving in to these desires… it was too much to resist. He nodded slowly, his heart pounding in his chest.
- “Okay,” he managed to whisper. “I’m ready.”
Dr. Kaufman smiled, revealing a set of perfectly straight, pearly whites. She reached out and gently stroked his cheek before standing up and turning around. She unzipped her pants, revealing a black latex strap-on strapped tightly against her crotch.
- “Why don’t you undress for me, Jack? I want to see all of your pretty little secrets.”
Her voice was husky and commanding.
As Jack stripped out of his clothes, revealing his feminine undergarments beneath, he felt a sense of liberation wash over him. He had never been this vulnerable with anyone before. But with Dr. Judith, he felt safe. Safe and wanted.
A sense of release and freedom thanks to Dr. Kaufman
When he was finally naked, she walked up behind him and wrapped her arms around his waist, guiding him forward until he was kneeling on the examination table.
- “Now, Jack, I want you to spread your legs wide for me,” she purred, her breath hot against his ear.
He obeyed, feeling the cool air from the air conditioning brush against his exposed flesh. Ashe waited, anticipation building inside him, he couldn’t help but wonder what it would feel like to finally be touched by her.
Dr. Judith stepped between his legs, her hands gripping the edge of the table as she leaned in closer. She positioned the head of her strap-on at his entrance, taking a moment to coat the tip with lubricant.
Then, with a gentle push, she began to penetrate him. Jack arched his back, crying out in pleasure as she slowly but surely claimed him.
- “That’s it, Jack. Take it,” she urged, beginning to thrust deeper. “Give in to your desires. Let me show you what it means to be mine.”
With each thrust, she drove the strap-on deeper inside him, massaging his prostate with expert precision. Jack felt himself begin to lose control, his hips bucking wildly against her. He was close, so close…
She leaned forward, her breasts brushing against his back, and began to tease his nipples with her fingernails.
- “That’s it, sissy slut. Show me how much you want this.”
He cried out, arching his back as the sensation overtook him. He felt the first wave of release ripple through his body, and with it came a sense of release and freedom he had never experienced before.
Intense sensations for Jack
Dr. Judith picked up the pace, her thrusts growing more urgent as she sensed his impending climax. She reached around and stroked him, guiding him through the intense sensations.
- “That’s right, Jack. Let go. Give in to your desires.”
Her words were like a mantra, driving him closer and closer to the edge.
As he neared the brink, he felt a warmth spreading through his body. It began at his core and radiated outward, filling every inch of him. He gasped as the first wave of release coursed through him, his muscles tensing and his back arching off the table. He could feel himself spilling over the edge, and with each passing second, the sensation grew more intense.
Dr. Judith continued to thrust into him, her stride growing stronger as she sensed his climax approaching. She leaned forward, her breasts brushing against his back, and planted a kiss on his shoulder.
- “That’s it, Jack. Let go. Give it all to me.”
The words of this dominatrix sent a shiver down his spine, and with each thrust, he felt himself getting closer.
As the last threads of his control snapped, he felt himself spilling over the edge. His body tensed, and he arched his back off the table as wave after wave of pleasure coursed through him.
He could feel himself emptying himself into the cup that Dr. Judith held beneath him, and with each spurt, a new sense of release and freedom washed over him.
Dr. Judith continued to thrust into him, her pace unrelenting as she milked him of every last drop. Her hands gripped his hips tightly, guiding him through the intense sensations.
She leaned in closer, her breasts brushing against his back, and began to kiss and nip at his shoulder
blades.
- “That’s it, Jack. Give it all to me.”
