Slowly I start to wake up, my eyes opening to small slits, breaking the darkness but also partially blinding me as I adjust to the brightly lit room. My head still spinning and foggy as I try to recall the most recent events, my brain desperately trying to figure out whether what happened was a dream or a reality. My question was quickly answered when I noticed the arm draped over my belly, the breath on my neck of someone behind me, and then I felt something sitting between my ass cheeks. The arm around my belly tightened pulling me closer to the body behind me and settling the intruder between my cheeks. I slowly turn my head and see the face of a very beautiful woman smiling down at me. My memory coming back to me in fragmented pieces like putting together a jigsaw puzzle. The woman’s name was Kendra and she was nice enough to help me last night after our adventurous night of unbridled passion.

“You seemed to have slept pretty good last night,” she said as she kisses my forehead, “but after everything you went through that can be understandable.” She giggled as she started to get out of bed, her blonde hair glistening in the sun as it swayed and tumbled. Her hips swished back and forth under her red satin teddy, the fabric flowing over her like water. She turned her head and winked before going into the bathroom and closing the door. “You had better get up,” she cried from the other side of the door, “we’ve got a long day a head of us.” I gathered myself out of the bed and then realized that I was still in the pink women’s t-shirt, pink panties, and white frilly socks. I quickly made my way over to the pile of my clothes over on the chair. As I picked up the pants I noticed the huge rips in the waistline and all over the back. As I picked up my other items I noticed they were in very similar, tattered remains. I sighed, not knowing what to do but knowing I couldn’t go out dressed as I was right now.

I heard Kendra chuckle behind me as her hands slipped around my waist, clasping together over my belly. Her body pressed against my back and I felt a slight pressure between my cheeks again. Her hot breath on my ear made me shiver as she whispered in my ear. “Don’t worry baby,” she said softly, “there’s a clothes shop right downstairs that I work at and it’s still early so there won’t be anyone there.” I nodded, letting the tattered remnants of my clothing fall to the floor. She uncurled herself from me, grabbing a hold of my hand she led me out the door and down the steps to the store below.

Rushing through the store I didn’t really have a good chance to see what all was available as Kendra led me to the back where the changing rooms were, pushed me in , and quickly closed the curtain telling me to sit tight while she grabbed a few things for me. I took the liberty of stripping out of the clothes I had slept in last night and piled them neatly on the bench. Taking a step back I looked at myself in the mirror and started to take note of myself. I was a rather small man with almost no chest hair, or hair anywhere on my body except on top of my head, that hair I had let grow out a little. I was so lost in thought that I didn’t even notice the bag Kendra had tossed into the stall with me until I heard her tell me to hurry up and get dressed. I opened the bag and dumped the contents, confused at what laid out before me. There was a slender white girls T-shirt, some rather high cut shorts, some white knee high socks, and, to top it all off, a pair of pink boy shorts. I think Kendra heard me sigh because she told me that those were the only clothes in the store that would probably fit me.

Resigning that it was either wear the clothes or walk around naked I decided to put on the garments. First, I slipped the shirt over my head, the fit of it hugging against my waist as it broadened at the chest. Next I picked up the knee-high socks and slipped them on. Then I picked up the pink boy shorts and looked at them, a debate still going on in my head. I let out my breath and slid in one leg and then the other, pulling them up to settle against my hips, my small cock and balls tucked snuggly inside. As I bent over to reach the shorts I heard the curtain of the dressing room rustle but before I could get a word out the curtain flew open revealing a smiling Kendra standing there looking me up and down. My cheeks turned red with blush as I watched her hungry eyes crawling all over my body. “Oh god, baby,” she said, her breathing becoming more heavy, “you got me so hot with your sexy ass in those things.” Looking down I noticed the growing bulge in her panties and the expanding wet spot on the fabric.

I felt her hands on my shoulders and without any resistance I sank to the floor, her hard cock straining at the fabric of her panties.