I didn’t tell my girlfriend, Shelley, that I liked to wear her clothes when she wasn’t around because I never thought she’d be into cross-dressing.

I also didn’t want to scare her away. I’d always kept my cross-dressing a secret. This wasn’t difficult. I simply indulged in my private fetish on nights when I was alone.

She is the first girl I’ve ever lived with, and I found staying out of her closet to be almost impossible. All those fancy outfits, pretty sweaters and dresses made of stretchy jersey. I’d never believed all that would be so close to my fingers — or body. So whenever Shelley went out on the weekend with her girlfriends, or if she was late at the office, I’d slide on one outfit or another from her extensive wardrobe.

We weren’t exactly the same size, of course. But we’re tall — she’s five-foot-nine and I’m nearly six feet — and we’re both slim with long legs. Anything that had a little spandex worked for me. I soon discovered favorites: one black dress that hit her at the knees and me at the mid-thighs, a few ethereal blouses with billowy sleeves and low-cut necklines, flowing skirts with elastic waistbands. I indulged in her scarves, her stockings, even her underwear. I loved the way the fabrics felt against my body. I would walk around in her satin tap pants or lacy boy shorts, appreciating the subtle caress of beautiful material against my skin.

Some nights, I applied makeup, too: eye shadow, lipstick, blush. Shelley had quite the collection, and I would open up a fashion magazine and do my best to emulate the pictures I saw there. A little highlighter on my cheekbones, a sparkle of glittery dust on my collarbone. Then I’d admire myself in the mirror before jacking off to my own reflection.

But during one of my dress-up nights, Shelley came home early.

I heard her key in the lock and froze. Strip! My brain demanded. Take it all off! Jump in the shower! Quick! Run!

But there was no way for me to hide what I’d been doing. Every so often, she’d come home while I had on a pair of her underwear beneath my jeans. But this was different. I was wearing her leopard-print formfitting cocktail dress. My hair was teased into spikes so different from my normal style. And I’d applied a full face of makeup. I even had on one of her favorite perfumes, a subtle orange-blossom fragrance — perfect for spring.

Shelley looked… well, surprised. She opened her mouth, and then shut it again. It was as if she’d been completely robbed of her voice. I winced. What was she going to say? Perhaps: Get out of my dress! Get out of my life!

“Get over here,” she said instead. Not what I’d expected at all.

“What?”

“I thought you were wearing my clothes, Ricky. But I had no idea that you’d look so… so good in them.”

“Why are you home early?” I managed to stammer. She was gazing at me with her big brown eyes. Her hair was loose and wild. When she goes to work, she pins back those unruly curls. But for nights out with friends, she lets her corkscrews free.

“It was a dull night. I decided I’d rather spend it with you than listen to Josie complain about her boyfriend.”

I was happy to hear that, but then I had to ask: “What do you mean that you thought I was wearing your clothes? How could you tell?”

The evening was progressing way too fast for me to keep up.

“You don’t hang things back the way I do,” she explained matter-of-factly as she stroked my body. “You try. It’s obvious. You try to put things back the way they were. But I have a special way of organizing my clothes.”

My cock had been semi-hard throughout the evening as I’d paraded in one outfit after another. But now, with Shelley’s obvious admiration and approval, my dick was at full mast.

“You’re so sexy,” she said. “I just hadn’t… I don’t know. I hadn’t imagined the full effect.” She stopped touching me for a moment and stepped back, as if she wanted to take in the whole of me. I posed automatically, the way I often did in front of the mirror on the back of the closet door. I cocked a hip like a model. Shelley giggled.

“Why didn’t you say?” I asked her. “Why didn’t you tell me you knew what I’ve been doing all this time?””

“Well, why didn’t you tell me?”

“I wasn’t sure how you’d react.”

She came into my arms. I held her tight. She wriggled her body against mine, and I knew she was feeling my erection through my dress and hers. My cock had been paying attention to the conversation as carefully as the rest of me had.

“How’s this for reacting?” she queried as she made the most of the connection between the two of us. I swallowed hard. She was going to make me shoot off in her panties if she kept wriggling against me like that, and I told her so.

She got me on the bed and took off her own clothes, then curled up next to me and began to stroke me through the dress and the panties. My cock was trapped in the finery, pressed up against my belly. She manhandled me through both layers of fabric until I was on the very verge of exploding.

“She began to blow me. I was close to the finish line, and I told her.”

“Baby,” I said, “I’m going to make a mess… ”

To my relief, she shoved the dress up past my waist, and we both watched as my trapped cock did its best to burst out of the undergarments.

“Take them off,” I begged her.

“In a moment,” she promised me. But first, she kissed me through the sheer underwear. My hips pounded against the mattress. She laughed again, a pretty tinkling sound, and then slid the knickers down and off. “We’ll have to get you shoes,” she said, noting my bare feet. “I know we’re not the same size. I want to see you dressed as a woman from head to toe.”

I nodded, thinking how great it would be to go shopping with her. To have her help me with my look.

But she was helping me in an even better way at that moment, wrapping her fist around my rod and closing her soft lips over the tip as she began to blow me. I was close to the finish line, and I told her. Usually, I’d never stop one of her world-class blowjobs. But I wanted my cock buried in her pussy, and I feared that I didn’t have long before I came.

She understood and straddled me, her hands stroking my chest through the dress as her pussy enveloped my rigid dick. Then she squeezed where my tits should be and said, “You’re not wearing the matching bra.”

I shook my head.

“We’ll take you lingerie shopping,” she promised. “We’ll go together, pick out the best bras, the ones with extra padding.”

I bucked into her, bouncing her into the air.

“Then we’ll do your makeup and get you a wig.” She was almost panting. I wanted her to continue. I was captivated by the story she was spinning for the two of us. “Just imagine if we went out together to the bar. I think you might be able to pass as a lady. With a little work, you know. With a little effort.”

I thought of the nights I’d been by myself, struggling to recreate the images I saw in the fashion magazines. I remembered rushing to wipe off the makeup before Shelley got home, using her cotton balls and makeup remover and hiding the color-saturated cotton in the trash beneath discarded tissues. I didn’t have to hide any longer. She and I would be open with each other. And that was going to mean pleasure in a way I’d never even allowed myself to imagine before.

“There’s this two-piece outfit in my closet,” she said, rocking her hips and grinding against me. “It’s black and stretchy. I know it will fit you. In fact, I kind of thought about you when I bought it.”

I knew exactly which outfit she was talking about. I hadn’t tried it because the tags were still on. But I’d admired it longingly.

“How did you learn how to do your makeup so well?” she asked, running one finger along my bottom lip. She was surely smearing my lipstick, but I didn’t care. I wanted her to smear me. I wanted her to kiss me so that I was wearing her lipstick and she was wearing mine.

“Your magazines,” I sighed, “and videos online.”

As she described the way we’d go out together on dates, as two girlfriends having a night on the town, I reached the end of my control. I told her I was coming as the first blast of cream jetted out of my dick. She shuddered and stroked her clit, climaxing along with me.

“It’s going to be so sexy,” she sighed as she fell into my arms. “The two of us.”

She ran her hand over my leopard-clad figure, and I felt grateful that my love of her clothes and her love for me fit so neatly together. Like a foot in a shoe, a hand in a glove, a pair of panties and the matching top.

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