I used to spend a lot of time away from home for my job. It had its downsides, but it gave me a chance to do my favourite thing: show off. My toolbox had a locked compartment containing a small selection of cam-suitable wardrobe items: a single camisole, a few panties, and two pairs of nylons - one thigh-high and the other to the waist.

I travelled a mostly predictable route, so I was a regular at several hotels around the region. Along with racking up enough points to take my wife on a nice holiday every year, I enjoyed frequent free room upgrades when the hotel business was slow. Having a couch or a sitting room with another TV were nice additions, but the wall-length mirror I often found was a favourite bonus.

On one particular evening such as this, I'd eaten my supper, finished my work for the evening, and called home. Finally, I could open my travel kit. I selected a reliable pair of pink satin panties - nothing fancy, but I liked the way they cupped my bulge and restrained my cock as I got harder. I tucked myself in and then put on the thigh high hose - black with a lacey little cuff along the top. I examined myself in the mirror. No one was at risk of mistaking me for a woman, but I knew where I could find others spending their evening as I was, and an audience for it.

I opened a crossdressing chatroom, started my camera, and waited to be noticed.

Things were quiet, a little boring. I had one brief chat with someone who wanted to know where I was and wasn't satisfied with me refusing to be more specific than the state. I'm suspicious of people who are too nosy about my details - I don't come to this place to meet people in real life - so I let the conversation drop. Suddenly, I was distracted by an unexpected knock at the door. I quickly threw on my sweats and a t-shirt, closed my laptop, and answered.

It was a hotel maid with her cart. She appeared forty-ish and fit, though it was tough to tell too much about her body from the shapeless tan shirt and pants of her hotel uniform. She looked down at my nylon-covered feet, sticking out the bottom of my pants. "Did I interrupt something, sir?" she asked with a wink. I started to stammer out some sort of answer, but she stopped me with a slightly raised hand. "It's all right, sir. I know what you were doing. It's what brought me to your door."

I was stunned to silence. "Would you like to talk about this more out here, sir?" God, no - I panicked and stepped out of her way. She pulled an overnight bag out from her cart, hung the Do Not Disturb sign on the door handle, and stepped inside the room with me, shutting the door behind her.

"I know what you're up to. I've got a friend in IT here. He keeps an eye out for an unencrypted chat over the wi-fi. Most of the time, it's just guests skyping with their families. Occasionally, it's dirty vanilla chat. Sometimes, he finds someone like you, and he lets me know. You'd be surprised how often."

"Why would you do that?"

"I'm genuinely interested in people like you, sir. I'm not here to cause you any problems. If you tell me to leave, I'll turn right around. But I'd like to show you what's in the bag, first."

She unzipped the top and held it open for me to see inside. Inside were neatly folded clothes that caught my interest. White lace, bright pinks, and pastels, frilly intriguing blacks, lots of cloth shining with its sheerness.

"My friend noticed you weren't completely dressed up - just a little underwear. Don't you ever ache to experience more? Today's your day if you want it to be."

I closed my eyes for a moment. I'd wondered about my dressing up, if there was anything more to it. Was this the day? I'm shy and suspicious, I certainly don't seek out adventures. If I had found a random posting on a website offering this opportunity, I would have never answered. But here it was, arriving unasked directly to my door. How does anyone say no to an opportunity like this? I opened my eyes, smiled, and told her "Yes. I'd like that."

"You may as well drop the cover-up, then. Let me see what I'm working with." I turned my back to her as I removed the shirt and sweats. I was still tucked into the panties, but my cock was straining against them. I was unexpectedly aroused, considering how nervous I also was. On top of all the other confusing emotions I was experiencing, I was embarrassed by my erection. She seemed perfectly satisfied to examine me from behind instead.

"Well, the thigh high stockings you're wearing are fine, but those pink panties look like Target bargain bin." She wasn't wrong. "Let's find something a little more alluring. I'm glad you like pink." She rustled in the bag, then She guided my shoulder to turn toward her. She looked me only in the eyes as she handed me a pair of bright pink satin panties with a little bow at the front and a peek-a-boo opening down the back. I held them, uncertain. "Go ahead. What more do you have to be shy about now?" She was right. I dropped my panties to my ankles and stepped out from them, letting my erect member spring loose.

I closed my eyes and sighed a little as she took my cock in her hand, but instead of stroking as I'd hoped, she held my shaft still, pinching the vein closed gently but tightly while my erection faded. "What's your name? I'm not going to call you "sir" while I'm standing here with your cock in my hand." She hadn't checked the hotel registry! I realised that I'd feared some sort of blackmail, but she really did seem to be as she said: here to help, not to take advantage. Still, caution guided me, and I gave a name I used online. "Don," I said.

"That's a perfect name - genderless. You can be Don with an O or an A-W fluidly; however, you want to hear it moment-to-moment. You should call me Miss Lisa". She let go of my now-flaccid dick. "That should help," she said as she let go. I put on the panties she'd supplied and tucked myself right back in the way I had been in my own pair. I looked at her, seeking approval. She looked me over and smiled, which was enough to start my erection again. Only the panties restrained me as the others had before.

She gently laid her fingertips on my waist and allowed them to trail behind her as she walked a circle around me, looking me up and down from all angles. Nearing the end of her first trip around, her fingers reached the small of my back while she stood at my side. She stopped and traced one finger down past the waistband and into the peek-a-boo gap of the panties. She traced further southward along the meeting point of my asscheeks, without forcing them to part for her, to the bottom of the peek-a-boo opening. She traced back upward, this time letting her finger part the cheeks. Once she reached the waistband again, she resumed her walk around me.

She took a second lap before she stopped and stepped away. She went back into her bag and pulled out a sports bra. It was bright pastel yellow, slightly padded. It seemed an unusual choice for a feminising effort, and I said so.

"Put it on. A regular bra looks silly on a flat-chested man without a lot of padding and careful work. But a slightly padded sports bra like this creates an effect that you don't need breasts to pull off." I put it on and faced the mirror. She was right. I owned a couple of bras, and I liked the idea of them. I liked the frilly girly look of them while they were sitting loose in my secret stash back home. But when I wore them, I never felt like they were working the way I'd hoped. With the sports bra, I was more believable as having the chest of a small-chested but fully-grown woman. I cupped the breasts and closed my eyes. Lisa stepped behind me, wrapped her arms around to cover my hands with hers. She whispered in my ear, "Here's your first lesson. How you look can completely change how you feel."

She took a step back while I admired myself in the mirror. "Take that off. There's something else we're going to try." She pulled a corset out of her bag, white and lacey. "There are other ways to produce an effect."

I removed the sports bra and pulled the corset over my head. Lisa turned me to cinch it tight. "It's going to feel restraining, but it's important you can breathe. It's less important that you can breathe deeply, however," she said with a smile. As she tightened the laces, I could feel it squeezing me just above my hipbone. She tightened it as much as she could, then tied it off in a bow. She spun me back toward the mirror. I'm a skinny guy, so it was a surprise to see my shape bent into an hourglass. But dressed in this, with hips and chest wider than the midsection between, my body suggested a womanly lushness to it. My breath caught, and I discovered Lisa wasn't entirely joking - I could only inhale so deeply while my body was squeezed this way.

"I was ready to dress you up more, but just look at you! You can barely restrain yourself, and I'm not prepared to do it for you today." Not prepared to...? I had no time to explore the thought. "Are you enjoying yourself?" I nodded, but she was looking in the mirror at the bulge in the panties, straining to burst out. "I can see you are."

She turned me to face the mirror fully, then stepped right behind me again. She brought her hands to where my hands were, along my side, and lifted them up to the cups of the corset. "Press and fondle your breasts, Dawn, like you did in the sports bra."

"Yes, Miss Lisa." She squeezed along with me for a few moments, until I was kneading my chest like there were breasts to fondle, as I'd often seen my wife, sitting above me and riding my cock, do to herself.

Lisa's hands dropped to my hips. Her body pressed into my back. I could feel her breasts squished up against me. I could feel her thigh pressing against my bare ass where the peek-a-boo panties left me exposed. There was a lump in her pocket, smaller than an egg, pressing into my crack. I froze for a moment. Her hand reached down to my knee, then traced the side of my nyloned thigh. She reached around me, rubbing the silky lump at the front of the panties, before diving in past the waistband and adjusting my cock to spring upward from where it had been tucked. She held it gently and began slowly stroking. I found myself moving with her, pressing back against the lump behind me.

"This is probably a good time to talk about what happens next."

Next? My head was spinning.

"You need to know, I'm not a Domme, but I am going to direct what happens in this room when we're together. Think of me as a teacher. That's why I want you to call me 'Miss' Lisa. I want to help you find out who and what you can be." She continued to slowly rub and gently knead my cock.

"Because I'm not a Domme, anything I suggest is open to negotiation. There won't be any need for a safeword - your safeword will be "no," and I'll respect it. But be aware that if, as we're discussing those suggestions, I tell you I require something, and you say no, that's the end of what we're doing here. I pack my things, I leave here, you never see me again, and anything I had left to teach you will go unlearned. Do you understand this rule?"

I moaned a "yes, Miss Lisa," and pressed my ass into her leg. She responded by exploring my groin further with her hand, pushing the panties further down as her fingers rubbed a path down my shaft and ballsack to my taint, then left the panties tucked behind my balls as she caressed back upward, cupped my balls slightly, and then held my cock to resume stroking.

I could hardly catch my breath in the corset. I panted shallow breaths. She gripped my shaft more firmly, pulling me back into her with each backstroke, the little lump behind me gently parting my asscheeks.

"Also, I'm no homewrecker. Your relationship with your family is more important than what we do here. You've been keeping your cam play a secret from your wife all along, I suspect?" I hoped she took my grunt of "mmm" as affirmative. "Then this will be no different. Do you still fuck your wife? Have you slipped into a routine?"

"Miss Lisa, I'm going to cummmmm...." .. my words trailed into a moan.

"That's what I want for you, Dawn," she said, as she pushed me forward gently. I was momentarily unbalanced, took a step forward and began to topple, then caught myself with my hands on the wall on either side of the mirror. Lisa angled my cock slightly upward and stroked rapidly, and the first streams of creamy white spunk landed against the mirror's image of me, hitting my reflected breasts. I watched it drip slowly downward, a line down the corset and toward my cock and balls, sticking out above panties tucked underneath.

She held me like that as my orgasm subsided, then let go of me and backed away, while I continued to lean against the wall, trying to catch my breath, taking only the shallow breaths the corset allowed. I was slightly dizzy from the effort and could feel my knees start to give way, but managed to get myself to the couch to sit before I landed on the floor. Lisa sat beside me, passing me a washcloth to mop up my dripping junk before I got anything more on the lovely clothes she'd lent me.

"Let's return to my question, Don. Do you still have regular sex at home?"

"Yes, Miss Lisa," I confirmed.

"Are you in a routine? When do you fuck?"

"Once a week - usually every Saturday night," I admitted. Between my being away, and my wife's demanding work schedule, we'd fallen into a predictable Saturday night lovemaking. It was still often tender and intimate, but certainly predictable.

"Do you come to this hotel regularly? When are you scheduled to come to town next?"

"I'm generally here every three weeks, on Wednesday night."

"Okay. I'll be looking for you three weeks tonight. Your homework until then is to avoid sex with your wife on the last Saturday before you return. Get too drunk, go to bed early, have people over, I don't care. Find an excuse, but not one that suggests there's anything wrong with your desire for her. I want you to avoid cumming for the week and a half before I next see you. It's important to our next lesson. Can you do that?"

"Yes, Miss Lisa. I can do that."

"Good. As far as I'm concerned, what we're doing here should be a secret from your wife, the same as the dressing up on camera has been for you. This is not an affair, it's a journey. This will never be about us, this is about you. There's a reason I like helping people like you, Don."

"Why is that, Miss Lisa?"

"That's none of your business," she sternly replied. "Just be glad that I do.

"Finally, I want you to reflect on today's lesson. I'm an average middle-aged woman. You wouldn't notice me twice if you passed me on the street. I haven't removed a single stitch of my clothing." She stood, then took my hand to stand me up again, guiding me back to the mirror. "You came while viewing this image of you. You saw yourself bent into this feminine shape and you couldn't control yourself."

She came around behind me to unlace the corset and help guide it over my head. "Before I go, do you have any questions?"

I was terrified to ask, but my curiosity demanded it. "Miss Lisa, I felt something pressing into me from behind. Miss Lisa, do you have a penis?"

"I'm not going to answer that today, Dawn, but you'll find out soon enough. In the meantime, I'd like you to think about what we're doing here, and consider a question in return. If I do have a penis, will it make any difference?"

I handed the corset back to her, which she tucked back in her bag of tricks, along with the sports bra. "You keep the panties, but wash them before next time. They should smell like fresh laundry, and you should be wearing only them and fresh nylons when next I arrive. I'll be at your door at 8:30 sharp. Here's a number for you to text your room number after you check in.

"Before you leave here, clean the mirror - my coworkers shouldn't have to deal with that. Now, thank me for today's lesson."

"Thank you, Miss Lisa." She nodded and swung the door wide as she left for anyone in the hall to see my nearly naked self still stunned by the events of the preceding half-hour. She walked away, pushing her cart, as the door swung closed.

I started counting the minutes toward a Wednesday, three weeks away.