He lost the bet and became my Summer Vacation Sissy!

Dear FemdomU,

I really enjoyed reading your stories about summer femdom experiences and saw your request for more, I felt inspired to recount my unforgettable summer vacation with my boyfriend, Jake. It was a summer unlike any other, filled with the kind of intense, humiliating, and exhilarating experiences that forever changed our relationship.

It all started with a simple bet. Jake was so confident he would win, imagining how he’d have me prancing around in skimpy clothes all vacation. But, to his surprise, I won. The terms of our bet allowed the winner to choose the loser’s wardrobe for the entire summer vacation at a rented cabin on the lake. And I knew exactly how I wanted to dress him: as a sexy female.

When I revealed my plan to Jake, his face turned crimson with embarrassment, but a bet was a bet, and he reluctantly agreed. The sight of his sexy, toned, muscular body in skimpy women’s clothing was something I had fantasized about for a long time. Watching him squirm in those outfits gave me immense pleasure. I didn’t just stop at the clothing, though. I spent hours painting his nails and doing his makeup, transforming him into the prettiest little sissy.

Our first day at the cabin set the tone for the entire vacation. I dressed him in a tiny pink bikini that barely contained his well-endowed cock. The sight of him struggling to keep it tucked away was both amusing and arousing. We headed down to the lake, where families and other couples were enjoying the sun. I made sure to parade him around, letting everyone get a good look at my sexy “girlfriend.”

As we walked along the shore, I noticed the stares and whispers. Some were shocked, others amused, and a few seemed genuinely interested. Jake’s face was a deep shade of red, his embarrassment palpable. I couldn’t resist teasing him as we swam, making sure his bikini top was always slightly askew, revealing his muscular chest. His cock would often peek out from the bottom, causing even more humiliation.

One day, I dressed him in a flirty sundress with a short hem that barely covered his panties. The thin fabric clung to his body, showing off every curve and muscle. We spent the afternoon shopping in the nearby town. With each step, the dress would ride up, exposing his panties and the outline of his cock. The shopkeepers and customers couldn’t help but stare, some with open mouths, others with sly smiles.

The most thrilling part of our vacation was when I invited the couple renting the cabin next door over for a nightcap. Jake was dressed in a sexy, sheer nighty that left little to the imagination. When they arrived, their eyes widened at the sight of him. We chatted and drank, the tension in the air thick with anticipation.

After a few drinks, I couldn’t resist pushing things further. I commanded Jake to kneel before our guests and please them. The man, a ruggedly handsome guy named Mark, looked at me with surprise and excitement. His wife, Linda, was equally intrigued. Jake hesitated, but a stern look from me made him comply.

I watched with delight as Jake’s lips wrapped around Mark’s cock, taking it deep into his mouth. Mark got a bit aggressive, grabbing Jake’s head and thrusting hard, making Jake gag and bringing tears to his eyes. Seeing my boyfriend’s face covered in Mark’s cum, his makeup running from his tears, was even more arousing than I anticipated. Jake’s humiliation and my power over him made the moment perfect.

After Mark finished, it was Linda’s turn. Jake licked and sucked her with fervor, his cock straining against the sheer fabric of his nighty. She moaned and writhed, clearly enjoying the attention. I couldn’t help but join in, making sure Jake knew he was my little sissy slut, here to please everyone.

The vacation continued in a similar vein, with Jake enduring endless humiliation and arousal. Each day, I chose a different outfit, each more revealing than the last. One evening, I dressed him in a tight, skimpy lingerie set and made him cook dinner for us while I lounged and watched. The sight of him bending over, his ass barely covered by the lacy panties, was a delicious treat.

By the end of the vacation, Jake had fully embraced his role as my sissy. He learned to enjoy the humiliation, the thrill of being exposed and objectified. And I reveled in the power and control, knowing I had transformed him into my perfect little plaything.

Thank you for giving me a platform to share my story. I hope it inspires others to explore their desires and embrace their fantasies, no matter how unconventional they may be.

Sincerely,
Roxanne