I never expected to tell anyone this, but the night everything changed started with a simple dare in our bedroom. My girlfriend, Lena, had that wicked smile she gets when she knows she's about to push me somewhere new. "Take off your clothes," she said, her voice low and teasing. "Tonight I'm dressing you like a girl."
My heart hammered as I stripped down, already half-hard from the command alone. She pulled out a black lace thong first, sliding it up my legs with deliberate slowness. The fabric cupped my balls and pressed against my cock, making it twitch visibly. "Look at that," she murmured, tracing the outline with one finger. "Already getting excited for me."
Next came the matching bra, padded and soft, hugging my chest. She fastened it behind me and stepped back to admire her work. Stockings followed—silky thigh-highs that she rolled on inch by inch, her nails grazing my skin until I shivered. A short pleated skirt came after, barely covering the tops of the stockings, and a tight crop top that showed off the bra straps. She added heels, lipstick, and a wig of long dark hair. When she spun me toward the mirror, I barely recognized the person staring back: smooth legs, painted lips, the bulge in the thong obvious under the skirt.
"Perfect," Lena whispered, pressing against my back. Her hands slid under the skirt, squeezing my ass through the lace. "You're my pretty girl tonight."
I moaned as she bent me over the bed. She lifted the skirt, tugged the thong aside, and slicked my hole with lube. One finger pushed in slowly, then two, stretching me while she whispered how cute I looked getting fingered in panties. My cock strained against the lace, leaking steadily.
When she replaced her fingers with her strap-on, I gasped at the thick stretch. She fucked me in steady thrusts, the skirt bouncing with each movement, the thong rubbing my shaft. "Say it," she demanded. "Tell me you love being dressed like a girl."
"I love it," I panted, pushing back onto her. "Dress me like a girl… fuck me like this."
She reached around, stroking me through the thong until I came hard, soaking the lace. Afterward she kept me in the outfit, letting me eat her out while she called me her good girl. The night stretched on with more dressing, more fucking, more confessions whispered against silk and skin. By morning I knew this was only the beginning.
