My first experience as a sissy. Part 1 👗
As a young high schooler, I found myself in a rather unique and thrilling situation. It all began when I tried on my girlfriend’s cheerleading uniform. The fabric was so soft and the colors so vibrant, it was like stepping into a whole new world. Little did I know, my girlfriend’s mother had suggested this very idea to her. We had a blast, just the two of us, exploring this new side of me. I was nervous at first, but she guided me through some cheer moves and cheers, and before I knew it, I was having the time of my life. The excitement was palpable, and I must admit, it was quite the exhilarating experience.
Fast forward a few months, and I was off to college, a fresh 18-year-old ready to take on the world. My ex, still in high school, was a senior at 18. I decided to stop by her house one day, and her mother answered the door. She invited me in to wait for my ex, and we chatted about college courses and life in general. She poured me a glass of wine, and we sat in her office, her in her business attire, looking every bit the successful professor she once was. She offered to tutor me, and though I was a bit hesitant at first, her confidence and charm were hard to resist.
As we talked, the time flew by. I looked at the clock and realized an hour had passed. I always showed respect to my girlfriends’ mothers, but there was something about her that was both intimidating and alluring. She had this air of authority that was strangely captivating.
When the conversation ended, she asked if I could help her carry some files to the basement. I obliged, and as I finished, she called me upstairs. She was dressed in a tight, business-like outfit that screamed sophistication and power. She asked me to help her button up her pencil skirt, and as I did, she turned to me and said, “Ah, you listen very well, just like my daughter told me. And by the way, I’m your new tutor, and you will obey that as well.”
I was taken aback but intrigued. Her bedroom was a vision of gothic Victorian elegance, and she sat on what looked like a throne, commanding my attention. She asked me to fetch her heels and help her put them on. I knelt down, my heart racing, and did as she asked. She smiled, her eyes gleaming with satisfaction, and told me to tell her how pretty she looked. I complimented her, and she, in turn, praised her heels, asking me to kiss the tips and thank her. It was a moment of pure submission, and I found myself both nervous and excited.
As I finished planting tender kisses on each stiletto, about 8 to 10 times each, I whispered a heartfelt “thank you.” She gently placed her hand on my chin, guiding my eyes to meet hers. With a soft yet firm tone, she asked, “Tell me the truth, darling. I heard you and my daughter had a fantastic time the other night while I was at my seminar?” My heart raced, and with a shaky voice, I replied, “Yes.” She smiled and corrected me, “No, yes ma’am.” I nodded, “Yes, ma’am.” She praised, “You’re doing very well,” and I responded again, “Yes, ma’am.”
With a playful twinkle in her eye, she instructed me to stand and led me to her master bathroom. Hanging there was a charming schoolgirl outfit from the local school where she used to teach. “You’re going to put this on,” she said with a warm smile, “and I’ll be your tutor. Don’t worry, I’ll help you put each item on properly.”
She playfully told me to undress and stepped out, leaving me with a new set of underwear. “Panties,” she corrected herself with a laugh. Seeing me tremble, she offered, “I thought I gave you enough wine to relax. Here, have another glass,” and filled it to the brim. “Drink some and relax. My daughter’s vanity is over there. Please have your panties on when I return in 15 minutes.”
Fifteen minutes passed, and I found myself sipping the wine, trying to calm my nerves. The vanity was a beautiful silver and pink chair, adorned with pink bows, and a stunning backlit mirror. The bathroom was a luxurious haven.
I heard her heels clicking as she returned. “I just spoke to my daughter,” she said with a devious smile, “told her I’m tutoring you for some classes.” She leaned in, her voice low and sultry. “I’m a dominant and superior woman, always wanting my daughter to bring someone home for us to doll up.”
“Really?” I asked, my eyes wide. “Oh, yes,” she replied, her voice filled with conviction. “The future is female, and I want to make sure my daughter runs the roost when she’s older. You’re perfect so far, so let’s continue with the training, darling. If you ever marry my daughter, I want to make sure you’ll be an obedient husband and son-in-law.”
She pulled out a bag filled with makeup, all freshly purchased from the mall that morning. “I’ve been planning this all week,” she said, her eyes sparkling with mischief. “My daughter is out with her girlfriends this evening and won’t be back till late to finish off the rest of the training.”
Let me paint you a picture of that delightful hour or so. It was all about transforming me into a vision of elegance for school, with her gentle guidance and a touch of her unique charm. She made it clear that she was the one in charge, and her daughter, well, she was the boss of all things relationship-related.
When she finished my makeover, she directed me to stand and slip into a pair of 3-inch Mary Jane heels with stiletto tips, sitting pretty by the bathtub. I obediently complied, feeling a flutter of excitement as I slipped them on. She then led me to the full-length mirror, her eyes sparkling with pride. “You look so lovely and studious, don’t we, Missy?” she cooed, using the nickname she had given me. “Missy, short for Michelle,” she added with a playful wink. I gazed at my reflection, barely recognizing the tall, elegant girl staring back at me.
She then turned me around and taught me how to curtsy, explaining that it was a sign of gratitude whenever I received an order. “Do you understand, Missy?” she asked, her voice soft yet commanding. “Yes, ma’am,” I replied, feeling a rush of admiration for her.
As we made our way to her office, she guided me on how to walk gracefully in heels and down the stairs. The office was a vision in pink, with a matching desk and chair that seemed to promise endless fun. “Isn’t this lovely, ma’am?” I asked, my voice filled with wonder. “Don’t forget to be polite, Missy,” she reminded me, and I quickly curtsied, the pleats of my blue and yellow skirt swishing gently.
She then showed me how a young lady should sit, legs together and to the side, with no slouching. “A young woman must always have proper feminine posture,” she instructed, and I made sure to follow her guidance to the letter.
The next few hours were spent reviewing my college homework, with a special focus on the essays she had chosen. We discussed books like “The Handmaid’s Tale” and delved into the history of women’s suffrage. She was so knowledgeable, and I hung on her every word.
Finally, she gave me my first assignment: a letter expressing my gratitude for her time and suggesting ideas for another feminist training session. I was filled with a sense of purpose and admiration as I began to write, eager to impress her with my dedication and creativity.
This experience was a whirlwind of emotions, but it was one that I’ll never forget. The blend of respect, submission, and feminine allure made it a truly unique and memorable encounter.
To be continued 🥰
