He stood in the expansive walk-in closet, surrounded by a dizzying array of clothing that belonged to his wealthy neighbor, Ms. Davenport. The house was quiet, save for the soft hum of the air conditioning and the distant sound of traffic outside. It was supposed to be empty for another week, but curiosity had gotten the better of him. He had never been in such a luxurious space before, and the sheer volume of clothes hanging neatly on racks and folded meticulously in drawers was overwhelming.His fingers traced over the fabric of different silky blouses and soft sweaters, then moved to a pair of sheer pantyhose. A mischievous smile spread across his lips as he considered trying them on. It wasn’t like anyone would know, right? With a nervous glance around, he began to undress, his heartbeat quickening with each item he removed.First, the pantyhose, sliding them up his legs, feeling the cool fabric against his skin. Next, a pair of lacy panties, followed by a padded bra that he stuffed with socks to give himself a more feminine shape. He selected a plaid skirt and a soft, fuzzy sweater, completing the ensemble. Turning to the full-length mirror, he admired his reflection, surprised at how natural he looked, how right it felt."Oh, my," came a voice from behind him, sharp and unmistakable. His heart stopped. Slowly, he turned to see Ms. Davenport standing in the doorway, her eyes wide with shock and something else—amusement perhaps? Disbelief definitely."I... I can explain," he stammered, his hands instinctively covering his chest, though the gesture only emphasized his predicament.Ms. Davenport stepped into the closet, closing the door behind her with a soft click. "Please, do explain. I'm all ears." Her tone was calm, almost playful, which only made him more uncomfortable."I was just... exploring. You have so many clothes, and I thought..." He trailed off, unable to finish his sentence. The silence stretched between them, heavy and awkward.She approached him slowly, circling like a predator eyeing its prey. "You thought you could just try on my things without permission?" She reached out, her fingertips lightly brushing against the fabric of his skirt. "These are very personal items, you know."He swallowed hard, feeling trapped. "I'm sorry, Ms. Davenport. I didn't mean any disrespect. It was just a silly impulse.""Hmm, a silly impulse," she repeated, her voice low and thoughtful. "And what exactly were you planning to do once you were satisfied with your little experiment?"He shook his head, not trusting himself to speak. The situation was spiraling out of control, and he had no idea how to fix it.Ms. Davenport leaned closer, her breath warm against his ear. "Maybe we should explore this impulse of yours further. What do you think?"He pulled back, shocked by the suggestion. "I... I don't know what you mean.""Oh, I think you do," she said, her voice now tinged with a hint of command. "But if you need a clearer picture, let me help you."Before he could react, she took his hand and led him deeper into the closet, where rows of shoes lined the floor. "Choose a pair," she instructed, nodding toward the selection.He hesitated, then picked a pair of high heels, mostly out of fear of what might happen if he refused. Sitting down, he awkwardly slipped them on, struggling to balance as he stood.Ms. Davenport watched him with a critical eye. "Not bad," she admitted. "But you need some practice. Let's start with something simple." She reached for a belt, tightening it around his waist. "Now, walk for me."He did as he was told, stumbling slightly at first, but gaining confidence as he went. Each step was a challenge, but also strangely liberating."Good boy," she praised, her approval fueling his determination. "Now, turn around."He spun slowly, the heels making a clicking sound against the hardwood floor. Stopping with he back to her, not able to see what she was up to when she suddenly grabbed his wrists."W-what are you doing?" he asked warily."A little something to enhance your experience," she replied enigmatically. Without warning, she started wrapping a long scarf she had grabbed around his wrists, binding them tightly behind his back.He gasped, realizing too late as he started to feel helpless. "Ms. Davenport, please!" he begged, his voice strained with a mix of pleasure and panic."Shh," she hushed him, "You need a little makeup and a nice wig to complete your sissy crossdresser look, and I won't have you squirming around!"He nodded weakly, still caught in disbelief that she had caught him and seemed to be okay with what he had done with her clothes. Hell, she even seemed to enjoy it herself!

A man explored his neighbor's luxurious walk-in closet while she was away. When he tried on her clothes, she caught him and instead of being angry, she suggested they further explore his crossdressing impulses. She tightened a belt around him and bound his wrists behind his back before adding makeup and a wig to complete his look.

He stood in the expansive walk-in closet, surrounded by a dizzying array of clothing that belonged to his wealthy neighbor, Ms. Davenport. The house was quiet, save for the soft hum of the air conditioning and the distant sound of traffic outside. It was supposed to be empty for another week, but curiosity had gotten the better of him. He had never been in such a luxurious space before, and the sheer volume of clothes hanging neatly on racks and folded meticulously in drawers was overwhelming.

His fingers traced over the fabric of different silky blouses and soft sweaters, then moved to a pair of sheer pantyhose. A mischievous smile spread across his lips as he considered trying them on. It wasn’t like anyone would know, right? With a nervous glance around, he began to undress, his heartbeat quickening with each item he removed.

First, the pantyhose, sliding them up his legs, feeling the cool fabric against his skin. Next, a pair of lacy panties, followed by a padded bra that he stuffed with socks to give himself a more feminine shape. He selected a plaid skirt and a soft, fuzzy sweater, completing the ensemble. Turning to the full-length mirror, he admired his reflection, surprised at how natural he looked, how right it felt.

"Oh, my," came a voice from behind him, sharp and unmistakable. His heart stopped. Slowly, he turned to see Ms. Davenport standing in the doorway, her eyes wide with shock and something else—amusement perhaps? Disbelief definitely.

"I... I can explain," he stammered, his hands instinctively covering his chest, though the gesture only emphasized his predicament.

Ms. Davenport stepped into the closet, closing the door behind her with a soft click. "Please, do explain. I'm all ears." Her tone was calm, almost playful, which only made him more uncomfortable.

"I was just... exploring. You have so many clothes, and I thought..." He trailed off, unable to finish his sentence. The silence stretched between them, heavy and awkward.

She approached him slowly, circling like a predator eyeing its prey. "You thought you could just try on my things without permission?" She reached out, her fingertips lightly brushing against the fabric of his skirt. "These are very personal items, you know."

He swallowed hard, feeling trapped. "I'm sorry, Ms. Davenport. I didn't mean any disrespect. It was just a silly impulse."

"Hmm, a silly impulse," she repeated, her voice low and thoughtful. "And what exactly were you planning to do once you were satisfied with your little experiment?"

He shook his head, not trusting himself to speak. The situation was spiraling out of control, and he had no idea how to fix it.

Ms. Davenport leaned closer, her breath warm against his ear. "Maybe we should explore this impulse of yours further. What do you think?"

He pulled back, shocked by the suggestion. "I... I don't know what you mean."

"Oh, I think you do," she said, her voice now tinged with a hint of command. "But if you need a clearer picture, let me help you."

Before he could react, she took his hand and led him deeper into the closet, where rows of shoes lined the floor. "Choose a pair," she instructed, nodding toward the selection.

He hesitated, then picked a pair of high heels, mostly out of fear of what might happen if he refused. Sitting down, he awkwardly slipped them on, struggling to balance as he stood.

Ms. Davenport watched him with a critical eye. "Not bad," she admitted. "But you need some practice. Let's start with something simple." She reached for a belt, tightening it around his waist. "Now, walk for me."

He did as he was told, stumbling slightly at first, but gaining confidence as he went. Each step was a challenge, but also strangely liberating.

"Good boy," she praised, her approval fueling his determination. "Now, turn around."

He spun slowly, the heels making a clicking sound against the hardwood floor. Stopping with he back to her, not able to see what she was up to when she suddenly grabbed his wrists.

"W-what are you doing?" he asked warily.

"A little something to enhance your experience," she replied enigmatically. Without warning, she started wrapping a long scarf she had grabbed around his wrists, binding them tightly behind his back.

He gasped, realizing too late as he started to feel helpless. "Ms. Davenport, please!" he begged, his voice strained with a mix of pleasure and panic.

"Shh," she hushed him, "You need a little makeup and a nice wig to complete your sissy crossdresser look, and I won't have you squirming around!"

He nodded weakly, still caught in disbelief that she had caught him and seemed to be okay with what he had done with her clothes. Hell, she even seemed to enjoy it herself!

A guy is hired to housesit for a wealthy neighbor women for a couple weeks. He stays at her expensive house and curiously snoops around. He finds her massive walk-in closet, and since he has a thing for crossdress, decides to try on some of her clothes. He puts on pantyhose, panties, a stuffed padded bra, skirt, and soft fuzzy sweater. While enjoying how he looks in the mirror suddenly she comes home early and catches him, then spends time dominating him.

Caught Crossdressing

0 words