The entire adventure began on a whim.

One day I said to my girlfriend, “I’ll be frank with you… ”

But before I could continue, she suggested, “Why don’t I be Frank?”

She gave me a look, then giggled, and whatever we had been talking about faded away. We lost ourselves in a fantasy of her wearing one of my suits and me trying to squeeze into one of her dresses. Truthfully, my clothes wouldn’t fit her right. I’m easily a foot taller than she is. But the fantasy still ignited powerful feelings I hadn’t expected.

Nothing else came of the idea for a few days, but then when I was taking laundry out of the dryer, I remembered our conversation. There I stood holding, Lola’s thong in my hand… and suddenly I had an erection worth writing about to Penthouse.

Without hesitation, I stripped off my clothes and stood there in our small laundry room wearing absolutely nothing. I paused for a moment, lost in a battle of “should I or shouldn’t I?” I’d never put on women’s underwear before, but what was the harm? Then I slipped on Lola’s thong. Of course, the flimsy thing didn’t fit. Not at all. The ribbon-like lace bisected my ass cheeks, digging deep into my crack, and the triangle of fabric could not even begin to cover my dick — especially with the hard-on I was sporting.

I pulled off the thong and rummaged through the warm laundry for something else of hers, wondering if anything she owned would fit me. I didn’t think so — until I found one of her nightshirts. Some of Lola’s nighties are formfitting, but the one I grabbed was made of satin and cut like a man’s pajama top. As soon as I held the slippery purple fabric to my body, I wanted to wear the thing. But once more I was foiled. The sleep shirt barely reached my waist, and my biceps seriously stressed the seams of the short sleeves. So I did what any man would. I wrapped that satin shirt around my cock and jerked myself off until I made a sticky mess.

Right then, I decided I’d have to go shopping for some feminine clothes. When Lola got home from work, I asked her if she wanted to join me.

“Who are you going to be?” she wanted to know.

“Who?”

“Do you have a name in mind?” she asked. “Are you someone cute, like a Traci? Or someone serious, like a Joan?”

“I have no clue,” I responded. “I don’t know what kind of girl I am yet.”

“I know,” Lola said, rubbing up against me. “You’re a slut.”

That’s how we ended up at our favorite sex-toy store, which sported a wide selection of exotic items. Their sizing went from petite to XXXL, so they had plenty for both of us to choose from. Together, we grabbed a variety of pieces — underwear, stockings and a stretchy rubber dress in vibrant blue for me. Then we barely made it back home before diving into our purchases.

Lola helped me prepare myself. She had me shave all of my body hair, and then she applied my makeup. When she was finished, I felt smooth and pretty, which is something I have to say I’d never felt before. Years before, I’d gone in drag for Halloween — like a lot of guys — but I hadn’t put much effort into my transformation. Back then, I hadn’t even shaved my five o’clock shadow.

But this time, things were different.

With my cheeks shorn and my legs soft and supple, I found myself really getting into the new me. When I spotted my reflection in the mirror, I saw that I was pretty. Not entirely female-looking but definitely eye-catching. I turned and looked at myself from all angles. She’d adorned my cheeks with a sparkling blush, added a red gloss to my lips and even glued false eyelashes in place.

“Damn, girl,” Lola said. As soon as I put on my pastel panties, she started to stroke my dick through the fabric.

“Don’t you want to see me all dolled up?” I asked, half-heartedly pushing her away.

“I can’t wait,” she told me — and I realized that I couldn’t either.

Then we were on our bed, rolling around together in the sheets. I knew my makeup was smearing when I kissed her, making all of her work for naught, but she didn’t seem to mind.

“Don’t take anything off,” she insisted, and then she was pulling the crotch of my panties to the side, exposing my hard-on. She blew me for several seconds, one hand stroking my balls through the satin. Her eyes were wild with lust.

“You’re just so fucking pretty,” she said, momentarily pulling her lips  from my rod. “I didn’t know you’d be so pretty.”

I loved the way she devoured me, as if she was impossibly hungry and couldn’t stop herself. When my shaft was glistening with her saliva, she yanked her own panties to the side and climbed aboard my cock. She bounced up and down, her hands on my smooth chest, as she confessed her fantasies.

“I want to dress you up, and then we’ll go out together. Girls’ night out, you know? Guys will send drinks our way and try to get our numbers.”

She was really grinding her hips on me, rotating to hit all those special places inside herself. I could feel her muscles tightening and releasing on my rod, as if her pussy had a will of its own.

“You’d like that?” I asked breathlessly. “The two of us pretending to be girlfriends?”

“Oh, yeah,” she said. “And afterward, you’ll fuck me out behind the club. In the alley. You’ll fuck me while we both look like ladies. And then… ”

She was on the verge. I could tell. Her cheeks were bright pink, and her breathing was erratic. “And then we’ll go home, and I’ll fuck your ass with my strap-on.”

Those words made me come as I jammed my erection inside her one last time. She groaned and climaxed with me, and then collapsed against my chest.

“Let’s try that again,” she said. “But this time, we’ll get the wig on you, too. I want the full experience.”

I sat up and let her help me put myself back in order.

This had all started with a simple joke, but there was no telling how far we’d go?

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