Ever since my teenage years in the small town of Burlington, Vermont, I’ve had a secret fascination with women’s lingerie. It started innocently enough during a walk through City Hall Park when I caught a fleeting glimpse of lace panties under a woman’s skirt, lifted by a gust of wind. The smooth fabric, clinging softly to her curves, captivated me. I wondered how that silky material would feel against my skin, how it might caress my body.
The First Opportunity
One afternoon, at 19, I was visiting my then-girlfriend Emily in her apartment in downtown Burlington. While we sipped coffee, my eyes wandered to a laundry basket in the corner of her bathroom. Nestled inside was a pair of ivory silk panties with delicate lace trim. My pulse quickened. When Emily stepped into the kitchen for a refill, I impulsively grabbed the panties and slipped them into my jacket pocket. Mumbling an excuse about needing to study for college, I left her place, adrenaline coursing through me.
Back at my tiny student apartment in the Old North End, I locked the door and drew the curtains. I laid the panties on my bed, studying them like a priceless artifact. Slowly, I shed my jeans and boxers, my body already tingling with anticipation. Sliding the silk up my legs was overwhelming—soft, cool, like a gentle embrace. I pulled the panties up until they hugged my groin tightly. My hands roamed over my hips, feeling the sleek surface, and I could barely resist touching myself right then. But I paused, savoring the moment.
A Growing Obsession
Over the next few weeks, my curiosity turned into an obsession. I started sneaking into Emily’s laundry basket whenever I visited, collecting a few more pieces: a black satin thong, a red pair with a bow detail. The secrecy gnawed at me, though, and I knew I needed to build my own collection. After Emily and I broke up—she never suspected anything—I took the next step.
On a rainy Saturday, I drove to Albany, New York, to stay anonymous. In a sprawling department store, I nervously wandered through the women’s lingerie section. A middle-aged saleswoman with a kind smile asked if I was shopping for my girlfriend. I nodded, stammering, and grabbed a set of garter belt, black silk stockings, and matching panties. Her glance as she rang up the items made my cheeks burn, but it also thrilled me.
At home, I tried everything on. Standing before the mirror, I admired how the garter belt accentuated my waist, how the stockings caressed my legs. I twirled, feeling the cool air against my skin, and knew I wanted to dive deeper into this world.
The Transformation
A year later, now living in a new apartment in Portland, Maine, I decided to fully embrace my passion. I’d read online forums where men described the sensation of smooth skin under nylon. So, I bought a high-end shaving kit and spent an evening in the bathtub. The warm water relaxed me as I carefully shaved my legs. As the hair fell away, I felt reborn. I went further, shaving my pubic hair, chest, and even my arms. After toweling off, I rubbed my skin with a lavender-scented lotion.
Then came the moment I’d been craving. I slipped on a pair of nude support pantyhose. The sensation was electric—the fabric glided over my legs like a second skin, massaging them with every move. My body responded instantly, but I held back, wanting to relish the feeling. I paced my apartment, noticing how the cool air seeped through the pantyhose, and suddenly understood why some people wore dresses to feel this freedom.
A New Chapter
In the following months, I let my hair grow past my shoulders. I ordered my first dress online—a simple, navy-blue sundress with flowing fabric. When it arrived, I prepared meticulously. After a long bath and another shave, I fastened a black garter belt around my waist, pulled on black silk stockings, and stepped into matching panties. I stuffed a bra with silicone pads for a more feminine silhouette.
Before slipping on the dress, I wanted to try something new. I’d read about anal plugs online and ordered a small, glistening glass one. With plenty of lube, I eased it in, feeling the unfamiliar but exhilarating sensation. My body trembled with arousal as I pulled the panties back up, securing the plug. Then I slid into the dress, smoothing the fabric and spinning in front of the mirror. The hem fell just above my knees, revealing enough to spark my imagination.
I sat at my vanity, which I’d set up for this purpose, and started applying makeup. After weeks of practice, I managed a natural look with foundation, eyeshadow, and eyeliner. I finished with a deep red lipstick that matched my long, wavy hair perfectly.
The Night That Changed Everything
It was a warm summer evening, and I’d decided to visit a club in Boston known for its open-minded vibe. The “Velvet Haven” was a hotspot for people with unique tastes, and I felt ready to show my new self there. I slipped on black high heels (size 10, men’s equivalent), packed a small purse with essentials, and left my apartment. My heart pounded as I crossed the parking lot to my car, but my neighbors seemed to be indoors.
Just as I reached my car, one heel snapped, and I twisted my ankle. A sharp pain shot through me, and I let out a quiet yelp. As I bent to fix my shoe, I heard footsteps. Looking up, I saw my neighbors, Ryan and Claire, a couple in their thirties who lived two units down. Concerned, they hurried over.
“You okay?” Claire asked, kneeling beside me. I tried to hide my face, muttering it was just a sprain, but it was too late. “Liam?” she whispered in disbelief. My heart sank. Ryan looked puzzled until Claire murmured, “It’s Liam.”
I wanted to bolt, but my ankle throbbed. Ryan grabbed my arm to steady me, and despite my feeble protests, they led me to their apartment. Ryan, a physical therapist, insisted on checking my ankle. In their cozy kitchen, I sat on a chair, unable to meet their eyes. Claire handed me a glass of red wine, which I downed gratefully.
An Unexpected Confession
As Ryan gently examined my ankle, Claire started talking to me. “Liam, there’s no reason to feel ashamed,” she said softly. “Everyone has their secrets.” Hesitantly, I opened up about my passion—how it started, how it fulfilled me. She listened without judgment. Then she asked quietly, “Have you ever thought about sharing this side of yourself with someone?”
Before I could answer, Ryan returned—and I couldn’t believe my eyes. He was wearing a stunning red corset, sheer stockings, and high boots (size 11, men’s equivalent). His face was made up, framed by a long blonde wig. He looked breathtaking. Claire smiled and said, “Liam, meet Riley—Ryan’s other side.” My jaw dropped.
Claire explained that she and Ryan had an open relationship for years, both embracing their love for crossdressing and more. They invited me to open up to them. After another glass of wine and their encouraging words, I let my guard down. Ryan—or Riley—sat beside me, and we started chatting. The atmosphere grew relaxed, intimate.
The Fulfillment
Claire slipped away briefly and returned in a silky robe. She carried a tray with toys, including a shiny dildo (about 7 inches long). “Liam, we want to show you how beautiful it can be to fully let go,” she said. My heart raced, but I was ready. I knelt as Riley stood before me. Carefully, I slid down their stockings, revealing their aroused body. With Claire’s gentle guidance, I began to please Riley, feeling the unfamiliar but intoxicating warmth.
The night became a whirlwind of sensations. Claire and Riley guided me through new experiences, always respectful and caring. We laughed, loved, and shared moments of complete surrender. As dawn broke, we lay exhausted on their king-sized bed, surrounded by tangled sheets and the scent of perfume.
A New Beginning
I never made it to the “Velvet Haven,” but I found something far more precious: acceptance and connection. Claire and Ryan became close friends, and we met regularly to share our passions. My journey was just beginning, but I knew I’d found my path.
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