Pansy Boy

Pansy Boy: About Me

My name is Thomas, but my stage name is Pansy, or Pansy Boy. I’m the lead singer-entertainer for my musical group called Pansy Craze. More on how that came about later.

While I’m biologically male, I possess feminine qualities. Depending on my mood or circumstance. I can look, dress, and act masculine, or be totally feminine. I possess the androgynous qualities that allow me to blend well with the gender I’m feeling at that moment.

In addition, I have been blessed with my mother’s “beauty genes:” high cheekbones, full lips, softer, more petite jawline, radiant, mirror-like gloss and supple hair, smooth, firm, and healthy-looking skin, and a lean, tall, and highly proportional figure. Forget the humbleness - I’m fucking gorgeous. Lucky me: I won the beauty lottery.

As a nightclub performer, I’m rare in that I don’t drink alcohol and I don’t do drugs. I don’t like to alter my mind. I like to be in full control and be aware of my surroundings.

I do like to have sex and I have a lot of it. I feel sorry for the folks who are on “hook-up” websites looking for action. Because of my fame and attractive features, the sex comes to me. Lydia, my live-in assistant, manager, agent, caretaker, bodyguard, psychologist, sex partner, and lover, chooses who we have sex with.

One evening, after a sold-out performance at a private event, I returned to my dressing room. My sequined bodysuit clung to my skin, sweating from the hot staged lights and the heat and humidity from the large crowd cheering, singing along with me, and dancing. I was still riding the high from the success of the show, but the adrenaline was fading, leaving my body sticky and my throat raw.

Then the door creaked open. Lydia slipped in first, her sharp heels clicking against the tiled floor, her lips painted the same shade of red as the dress hugging her curves. Behind her loomed a strikingly handsome, tall, muscular, broad shouldered young man, with shiny and satin ebony skin, dark piercing eyes, sensuous and lush lips, and a bright white smile. I thought to myself – OMG!!!!!!. Who is this treasure before me? My pulse jumped.

"You were fucking great tonight Pansy!," Lydia erupted, stepping close enough that I could smell the tequila on her breath. She traced a finger down my silicon breasts, over the damp sequins, before hooking it under my chin and tilting my face up. "But I think someone here has an admirer."

His gaze overwhelmed me, slow and deliberate, like he was hypnotizing me. "Hello Pansy, I’m Armari. You were fabulous this evening," he said, voice low, accent curling around the words. “I’m so excited to be finally meeting you. I’ve been waiting a long time for this.” I was in a daze for a moment - being in front of this magnificent being, as if I had never seen someone like this before. Quickly collecting myself, I grinned, my heart pounding, the heat within me building. I said, "Well darling……… what the hell took you so long?"

Lydia laughed, sharp and knowing, before turning to press herself against Armari’s chest. Her fingers tangled in his shirt, pulling him down into a kiss that was fierce - all tongue and teeth. I watched, breath hitching, as his hands slid down to grip her ass, hauling her flush against him. When they broke apart, Lydia’s lips were swollen, her eyes dark with want. Glancing at me over her shoulder, she murmured, "Armari’s got something to show you baby. Something really big." I raised an eyebrow and said, "Oh?" Armari smirked, reaching down to adjust himself through his jeans.

She didn’t waste time. Lydia dropped to her knees in front of him, fingers working at his belt with practiced ease. The buckle opened, the zipper went down, and then – HOLY FUCK!!!! - his cock sprang free - long, thick, heavy, and glistening at the tip. Leave it to Lydia – always auditioning the talent before bringing it to me.

I stared in disbelief. He was massive. The kind of dick that made you believe it was fantasy and not reality. His pubes, cock, and balls were smooth, shaved clean, the skin dark and taut over his heavy sac.

Lydia wrapping her lips around the head, tongue swirling over the slit before taking him deeper, her throat fluttering around the girth. I couldn’t look away. "Oh fuck………. that’s so good," Armari groaned, one hand tangling in Lydia’s hair, the other reaching for me. "Come to me Pansy," he said. Coming out of my daze, I sank to my knees beside Lydia, my own fingers trembling as I reached out, tracing the vein pulsing along the underside of his shaft. He was warm to the touch, the skin like silk over steel, and when I leaned in to press my lips to the head, the taste of him - salt and musk, it made me so aroused.

I followed her lead, my own mouth stretching around the width, tongue swirling as I hollowed my cheeks. Armari’s fingers tangled in my wig, holding me steady as he thrust up, fucking my mouth in slow, deep strokes. "Fuck…. so good,” he said, his voice was rough, his hips stuttering. "You two are gonna make me cum."

Lydia took over again and started to stroke him hard and fast. "Do it!," she panted. "Cum for us!" Armari’s breath hitched, and then – fuck - he shot his load - thick ropes of cum into Lydia’s mouth, dripping down her chin.

Armari watched us, his chest heaving, his cock still half-hard between his legs. "You two are insatiable," he rumbled. Lydia grinned, then leaned over to me for a kiss, sharing Armari’s cum.

And so goes our almost nightly post-performance activity. The three of us made our way back to our place where the sex continued until sunrise.

But you’re probably wondering how this all started. How did I get here? I guess I should start from the beginning.

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Pansy Boy: How It All Started

I was born and raised into a very privileged lifestyle in the West Village of Manhattan. My parents own a three-story brownstone building where I lived with them, my older sister by five years, Gia, and our live-in housekeeper, Alvita. My mom, a stunningly beautiful woman, came here from Italy as a young teenager, and was discovered by a talent scout, becoming one of the world’s most successful and sought-after fashion model. That’s where I got my beauty from.

My dad is a famous fashion photographer. They met during a photo-shoot. That’s how their romance and marriage started. My mom, in addition to being beautiful, is also creative and smart. She soon went from front-of-camera to behind, working at one of the most famous Parisian haute couture houses, eventually to become their creative director. Their fame and demand for their services had them traveling constantly, meeting and working with the wealthy, successful, and famous. That meant Alvita and Gia were in charge of my child rearing.

My mom told me that Gia cried when she found out she had a baby brother. She was so disappointed – wanting to have a sister instead. That didn’t stop her from treating me like one. Growing-up, I remember her having me play with dolls and dressing-up in little girls clothing. I wasn’t interested in sports or activities that boys liked to do.

By the time Gia was 18 and I was 13, I’ve grown quickly to where I was almost the same height and size as my sister. Gia had me grow my hair to where it was below shoulder length, started dressing me in her clothes while she and her friends would be practicing their make-up and beauty techniques on me. She would take me out in public with her friends, dressed as a girl, to go shopping, eating, or hanging out. I started to feel comfortable with this lifestyle and take-on a more effeminate persona. The clothes and make-up made me look much older than 13, and we lived in New York City, where diversity and self-expression was not only tolerated, but welcomed. I attended private school, dressed in mostly gender-neutral clothes with some light make-up, which I was now wearing daily. The teachers and kids either ignored or were accepting of my appearance. I was never bullied for my feminine appearance which was a relief. I know many kids like me were not so lucky,

You’re probably wondering what my parents were thinking about my gender transformation. Not much actually. My sister and Alvita were taking care of me, I was a happy child, and not getting into trouble. Mom and Dad were constantly busy with their own careers, so they were hands-off for the most part.

I loved to sing – especially Broadway show music and was very talented. I excelled academically to where I was able to graduate high school at 16. My parents arranged for my audition and enrollment into New York University, Steinhardt, which is the school for singers studying for careers in musical theater and contemporary commercial music.

During this time, Gia’s best friend Shelly attended the Arrojo Academy for high-fashion hair and cosmetology. I was her student – a.k.a. guinea pig - for her hair, make-up, skin, nails, and body treatments. I would go to her classes on late Friday afternoons to get “beautiful” for events later that evening.

By this time, I was dressing mostly as a woman, proficient at hair, skin, nails, and make-up – thanks to Shelly. My mother had the most beautiful haute couture dresses that I fit into and would borrow – without asking first. I looked much older than 18 and was able to go to bars and nightclubs without getting carded. Shelly was now working as a cosmetologist for the Broadway show talent, which meant I would tag along to see the shows and party with the cast in clubs after their performances.

During one such outing, I stunned the audience while singing “The Wizard” from Wicked at an open mike. It resulted in a two-minute standing ovation and two encores. That was the night I met Mortimer, or Morty as he likes to be called. Not only was he thrilled and awed with the control, power, and delivery of my signing voice, but that I was a man, unnoticeably dressed as a woman. He made me a proposition that would change my life.

Morty is a successful promoter of Broadway talent and creator of themed shows and events. He wanted to start a musical group, with a crossdresser/drag queen as the lead singer. The name of the band would be “Pansy Craze” and the lead would be named “Pansy Boy” or “Pansy.” The “Pansy Craze” was a period of increased LGBTQ visibility in American popular culture from the late 1920s until the mid-1930s. During the "craze," drag queens - known as "pansy performers" - experienced a surge in underground popularity, especially in New York City, Chicago, Los Angeles, and San Francisco. Morty wanted to bring back the Pansy Craze in a big way, and he felt I could deliver on his vision.

I should have consulted with my parents first, but being 18 and an impulsive, impetuous, inexperienced, and naive adult, I committed to Morty and jumped in with both feet. It was months of hiring musical talent, rehearsing, promoting, traveling, and performing, but things started to move fast and success and fame came quick. Morty introduced me to Lydia, his personal assistant. She’s 8 years older than me, stunningly beautiful, with an insatiable, wild, and reckless bisexual appetite. She’s my manager, agent, assistant, caretaker, bodyguard, constant companion, live-in lover, and therapist, providing me with a constant flow of beautiful people for our own erotic pleasure.

I open my story to the community to tell stories of our wild sexual escapades. All contributions will be moderated.