“Hey, what does your shirt say?” I called out.
The dark haired man turned to gaze my way. “Excuse me?” he asked.
“Your shirt,” I leaned over the counter to get a better look. On his t shirt was my last name written in decorated letters. I always knew I had a familiar surname if you live in the U.K. There it was on his shirt, advertising a pub.
“Can I buy it off you?” I asked him. “That’s my last name.”
He looked me over, more interested than he’d appeared before. “You want to buy the shirt off my back?”
Oh, his accent was so sexy. I hadn’t noticed at first because I’d been too involved in the t shirt. The way he said the words put sex in my head, but not words in my mouth. I started stammering, especially when he pulled his shirt over his head and tossed the tee to me. I caught the soft cotton and almost brought the shirt to my face to breathe in his scent, but I remembered where I was: standing behind the counter at the store I own. I needed to look professional, didn’t I? Or at least, pretend to be. I went to the register to get him some cash.
“I can’t wear cash,” he said.
“That’s right,” I nodded, admiring his broad chest, his flat belly. “What about a trade? You could choose any shirt off the racks.” I motioned to the array of colorful clothing around the store.
“How about the shirt off your back?” he asked.
“This one?” I didn’t understand. I was wearing my favorite silk blouse, the color of the sky at sunset, that pink that streaks the clouds. The man in front of me had to be six foot four with wide shoulders and muscles that told a story of hitting the gym daily. I had known his shirt would fit me like a nightgown. My shirt would fit him like a hand puppet.
He came behind the counter. “Do you have to stay open?” he asked. “It’s pretty close to six.”
That accent. He could have said anything, and I would have swooned. “Turn the sign,” he said, and I rushed to obey, then locked the door and shut the window blinds before I returned to him.
“Why do you want my shirt?” I teased. “Do you simply want to see me naked?”
“Yes,” he said matter of factly, “but drop the ‘simply.’ I want to see you naked, spread out on the counter, and I want you to see me all dolled up in something pretty.”
The way his eyes lit up at the end of that sentence startled me. This was definitely a first for me. The studly looking, sweet talking, fairly burly guy in front of me wanted to dress in pretty clothes. I could barely believe it.
“Are you serious?”
“I took my shirt off for you, didn’t I? It doesn’t get much more serious than that, does it?”
“All right,” I said gamely. This was the most exciting thing to happen to me in months. Maybe even years. I moved around him and into the main part of the store. What on earth would I have that might fit him? I thought for a moment, and then headed to a rack of long, flowing skirts with elastic waistbands. His problem would be the height. Would I have any shirts that would fit him? Aha. I had a whole row of beautifully printed artist smock type shirts, long tunics that ran to XXL. I snagged one that looked like a Matisse print and then went to find stockings. We cater to men and women, and we have a little of everything in the store. My assistant had purchased thigh highs that stayed on without garters. One size fits most, the package said. I’d been wary of these when she’d placed the order, but now I was infinitely grateful. Finally, I needed shoes. “What size shoe do you wear?” I asked. He answered with the UK size, which I translated easily to the US.
I sprinted up the stairs to the stockroom. No way would he fit in any of the ladies shoes I had, so I chose the most unisex looking pair of riding boots I could find in his size.
When I came back down, he was nude. What a delicious sight. He had taken off his shoes and Levis, and now he was standing in the middle of my store entirely naked. I had a difficult time not asking if we could forget the whole playing dress up thing and get right to the fucking. Let’s say it had been awhile.
“I don’t sell underwear,” I told him, happily eyeing his semi erect cock. The size of it made me smile. The girth made my pussy clench in anticipation. He would definitely be able to please with a tool like that.
“I don’t wear any,” he said with a grin, stating the obvious.
I handed him the thigh highs. As he opened the package, I asked, “Have you had much experience wearing ladies’ clothing?”
He looked so cute unrolling the stockings that I could barely utter any words, but I managed.
“Much. I don’t know. Plenty. A lot. More than your average sailor on leave.”
“I know what the word means.” He laughed. “I mean, what would you think much experience was? Six times? A hundred? Daily? Twice?”
“You tell me.”
He sat on a chair outside of the dressing rooms and pointed one of his feet. He had pretty feet, I noticed. Well pedicured, not rough. When I looked more intently, I saw that his toenails were painted a color I recognized as Polished Oyster. Revlon. I had a bottle of it at home.
Gently, he pulled on the thigh highs, answering my questions with the gracefulness of his gestures. Oh, hell, yes he had experience wearing stockings. That was for sure. I tend to rip them right out of the package and run them before I even slip on a shoe. My assistant jokes that I should take out stock in Hanes. But not this man. He worked with finesse, and I noticed as he pulled on the pair that his legs were shaved smooth. I hoped I’d remembered to shave mine!
I reached for the skirt and handed over the delicate, flowery material. He slid it on and then looked at me, waiting. I was the stylist. He was the star. I handed him the tunic. To my elation, relief and delight, the smock top worked. He didn’t look entirely female, but he looked surprisingly feminine. Something seemed to change in his face when he admired his sweet reflection in the wall of mirrors. His eyes narrowed, his lips pursed. I handed over the riding boots.
Can I say that I’ve always had a thing for a girl in riding boots? No, I’m not gay or even bi, but women who can pull off the look win a special place of honor in my heart. When he put on the boots, I felt my chest tighten. He looked so fucking sexy. I crawled closer toward him, and stroked the leather boots with my hands.
“What do you think?” he asked, his voice soft and hinting at his nervousness.
“I think I need . . . ” I started, and then he was pulling me up to standing, wrapping me in his arms.
“What do you need?”
My mind was spinning wildly. The way he asked the question was so erotic, as if he would be able to fulfill any wish that I might state. If I said, “I need you to tie me to the staircase railing and fuck me while you wear your skirt,” he would do it. If I said, “I need you to dress me up as a man and let me fuck you with a strap on,” he would do it. I didn’t know this for a fact that was only the sensation I had upon hearing his words: What do you need?
“I need . . . ” I said, and then I twisted out of his arms and sank to my knees. He looked down at me. I thought he could tell what I wanted from my expression he must have been able to because he started to hike up his skirt. I have to say, “started to hike up his skirt” is in an expression that had never described any action I’d experienced previously. I’d never been with a cross dresser, and I’d never been with a lover who wore a skirt. All my romantic experience to this point had been strictly hetero and fairly vanilla. Maybe this is why I was so fucking wet when I burrowed under his skirt in search of his cock. I was charting new sexual territory, and I loved it.
The light filtered through the skirt, making pretty patterns on the floor around me, as if I was basking beneath a stained glass window. I admired the colors for a second before being nudged by something long, hard and demanding.
I opened my lips.
Then I heard his sigh as I closed my lips around the head of his sturdy rod. He stroked my head through the delicate fabric of his skirt, and I began to pump my mouth up and down his unit. I loved that he was wearing those tall riding boots, that he had on no underwear, that he was fully clad in feminine clothes I had chosen. How much fun we might have in the future, I thought. I buy most of the clothes for the store. I’d be able to order the perfect sizes. I could even find wonderful panties for him, I realized, soft satin beauties that would hug his firm ass.
I had to slip a hand between my legs as I sucked him. My pussy was getting so wet that I could feel the juices through two layers jeans and bikinis. His cock seemed to let me know how to work him. He butted against me, and then pulled back. I found a rhythm and maintained the speed and suction, matching the pattern with the way I twirled circles over my own clit through my clothes.
But when I heard him say, “I’m getting closer,” I pulled back.
“I want you inside me,” I announced breathlessly.
I re emerged from beneath his skirt. His cock was tenting the gauzy fabric. He looked pitiful standing there, with no release, a hard on like a tent pole waiting for what was next. I stripped out of my shirt and jeans, then bra and panties. A shiver of delight ran through me. I liked the fact that he was dressed and I was nude. That he oh, wow. I realized in a flash that I didn’t even know his name.
“I want you to fuck me,” I said softly, “with you all dressed up like that. I want your cock inside me, while I’m naked. And I want to know your name.”
He cracked a smile and put out his hand. “Evan,” he said.
“I’m Deirdre,” I told him, looking at his cock rather than his face.
“Pleased to meet you.” I had to laugh as he grabbed me and bent me over the padded maroon chair in front of the dressing room mirror.
“You like to watch, Deirdre?” he asked.
He pulled the skirt up to his waist and then pressed the head of his cock between my legs. I was so wet that he slipped in easily. The sensation made both of us groan with pure pleasure.
“Do you usually get this wet?”
I shook my head I was telling the truth. I like sex, but this was different. This was unusual. I’d never been this aroused before. I felt as if my juices had coated the insides of my thighs.
“What’s the difference this time?” he asked as he thrust inside me. Oh, so he was a talker. I tried to respond intelligently, but I have to say, the way he was fucking me made most thoughtful dialogue evaporate from my brain.
“You,” I started, “in that skirt.”
That’s what it was, wasn’t it? The peacock like presentation of this handsome man in colorful, silky fabrics, so different from all the tough guys I’d been with before. Not that Evan didn’t look tough. But the plume of colors around his waist and the impressionist printed smock tempered the testosterone.
“I like me in this skirt, too,” he confessed, “and you naked, and the way the thigh highs feel on my skin. I’ve always thought women were the luckier of the sexes. You get to wear such pretty clothes. Why can’t men ever have a chance? Outside of the occasional Halloween costume, we’re pretty much relegated to denim or khakis and cotton.”
Yes, he was a talker. But at least he could fuck while he talked. The whole time he spoke, he rode me, his hands on my hips, pulling me forward and back, slamming his cock so deep inside me I thought I’d see stars.
“You like the feel of the skirt on your skin?” he asked, and I nodded. “Tell me.”
I understood what he wanted in a flash. “You’re so pretty,” I said, meeting his eyes in the mirror. “I love the way you looked in men’s clothes. But you dressed as a girl is far sexier. I want to dress you up in so many different things.”
“I want to make you beautiful, the prettiest boy at the ball.” On a whim, for no reason at all, I said, “And all the girls will want to fuck you.” And that’s what took him to the edge, and took me over it. We came almost simultaneously I don’t know whose orgasm triggered whose. But that’s how it worked wham, bam, thank you, ma’am we were coming. His hands held me tighter, his cock thrust faster, and then we slowed down and settled back on planet Earth.
I felt as if I’d run a race, felt as if I’d won the race. He pulled out of me and readjusted his clothes. I stifled a giggle, but then I had an idea.
Before round two, I moved around him and headed back to the counter.
“Where are you going? You’re not going to ring me up, are you?”
“Is that what they’re calling it these days?” I smirked and came back with my little striped cosmetic bag. “I want to see you in lipstick.”
He pouted for me. Perfectly. Clearly, the boy knew his way around a tube and I don’t only mean the subway. I had two different hues, a dark cherry and a paler pink. I went with the cherry and felt elated when I saw that the color suited his skin tone perfectly.
“What else do you have in there?” He took the bag from me, manhandled my blush brush, and then did up his cheekbones with my favorite bronzer. The clothes were all askew now, so when he gazed at his reflection, he looked debauched and used, but with a sparkle.
“You look so fucking sexy,” I told him. “I want you to kiss me. All over.”
I didn’t have to ask twice. He spread me out on the floor and started, his lips on my lips for only a moment still, I relished the sensation. I’d never kissed a man wearing lipstick before. I savored the silkiness of the gloss on his lips. Even the scent of the lipstick turned me on. I wondered if men felt the same way when they’d kissed me. I couldn’t imagine how they wouldn’t find this alluring. Then he moved down, along my neck, my chest, the curve of my belly. He was leaving imprints from my own favorite lipstick. That thought tied me up inside. I crossed my legs, feeling the wetness between them, but he uncrossed them quickly and began to kiss the very insides of my thighs. I wanted him to have the easiest access possible.
When he tongued my pussy, I sighed and wrapped my legs around his back.
“You taste so sweet,” he said, and I sighed. “I knew you would. I can always tell.”
He shook his head. His soft hair tickled the insides of my thighs. “There’s a look some women have, a look that lets me know they like sex, that they’ll be good, that they’ll taste sweet.”
I didn’t believe him, not really, but my body responded to his words. Everything he said was dipped in that accent. I wanted him to talk to me forever. I say that now, but truthfully, I also wanted him to keep eating me. The two desires warred for domination. He ultimately made the decision for me talking while he nibbled and licked, his voice slightly muffled by my wet flesh. “So sweet,” he continued, his tongue cresting over my clit, “like apples and cinnamon. Like honeydew melon.”
I was right on the verge when he moved once more. I watched as he stood and let the skirt fall to the floor. Now he was in the smock and the boots and stockings. He pulled off the top and I sucked in my breath. I have stood in an outfit so similar to his before many of my lovers. Girls in riding boots do the trick for many men. But this was unique. Evan in those stockings and boots looked like an Amazon from another time. A blend of the masculine and feminine that was sexier than almost anything I’d ever seen.
“I want to fuck you against the stairs,” he said, almost as if he’d read my thoughts from earlier. Or maybe anyone with a hard on would see what a good location my stairs are.
I stood up and walked to the stairway. He pressed me up against the wall, brought my hands over my head, and positioned me so I knew exactly what to do. I held on to the rails and felt him grip me from behind. For a moment, just a fleeting moment, he pressed against my ass. The feel of his stockings on my legs, the feel of his boots against my skin oh, I can hardly describe what a turn on that was. Then he was parting the cheeks of my ass to hold me open and sliding his cock into my pussy. From that very first thrust, I was gone. I could not remember ever being this aroused with a man before. Why hadn’t I ever considered asking one of my men to dress in drag? I’d done many things in the past but never this. And this was what turned out to be my biggest aphrodisiac ever.
“Keep holding on,” Evan whispered. “Don’t you let go.”
I gripped the rails tightly in both of my fists.
“I want you to come with me,” he said next, “at the same time I do. Will you?”
I felt like saying, “I’ll try.” But I knew he wanted more confidence than that. So I said, “Yes, Evan. Yes, I promise.”
He rode me hard, and I groaned and lowered my head, but kept my arms up, holding the wooden railings. How many years had I owned the shop? Ten. How many times had I been fucked in it? None. Thank God for Evan. I think I needed to play catch up and quick.
I could feel when the tempo changed, when he got into a groove that let me know he was getting close. Then he slid one hand in front of my body and started to stroke and pinch my clit in rhythm with his thrusts. He was going to make damn sure we climaxed together. I wanted to kiss him for that except kissing him would mean turning around, and I wouldn’t have let go of his cock for anything.
“Are you close?” he murmured.
“Right with you,” I said breathlessly.
We came like clockwork, like ringing bells, like two strangers who have found out they fit each other like velvet gloves. We came hard, and my fingers, sweaty and stressed from clenching the rails, finally slipped free. Evan held me tight in his arms, and then set me back down. I turned to look at him. His face was flushed, but the makeup was mostly still there smeared lipstick, but rosy lips. He was handsome yet beautiful at the same time. His stockings were slipping, and I loved that look. I wanted him to wear the nylon stockings under his jeans, so I’d know they were there. I wanted to take him home and dress him up in scarves and slips, satin and velvet. I wanted . . .
I looked down at his cock. He was hard again. Suddenly, I wanted something completely different. I pushed him down, so he was on his back on the floor once more.
“You aren’t planning on leaving any time soon, are you?” I asked as I climbed on for another ride.