Sweetness

My phone chirped right as I finished eating the club sandwich Gayle had brought back from the deli across the street. Did she say anything?

No.

Too bad. Guess you're stuck wearing what you're wearing. She followed that with: How is it going?

I could almost hear the compassion in her query. How could I answer that question? It was going fine. I was getting away with it and that was exhilarating. It was scary for the exact same reason. I wanted to stop, and I wanted to keep going. I wanted to wear a blouse and a skirt, and I wanted to put on a t-shirt instead of my camisole. I wanted what I wanted, and I wanted what Peyton wanted. Work was easier, there was no getting around that fact and that seemed to be the biggest catalyst for why I wasn't fighting what Peyton had suggested. Work had been a slog and now it was once again easy, like it had been when I'd first started. Business was booming, and we'd have to hire more people. Decisions about how to improve print ads that had so flummoxed me when I'd first started now jumped out at me with the ease of cat catching a wounded mouse. When my employees came in with a small problem, I'd see the answer now instead of a thousand different scenarios playing across my brain. That background hum of excitement caused by Peyton and my escalating cross-dressing had somehow simplified work, resetting it to an easier, more productive time. Good. How's work?

Slow, which is good. Eating lunch. Come over after work?

I took a play out of Peyton's playbook and sent back and emoji of a thumb pointing skyward, the universal symbol for A-OK. Peyton sent back a smiley face.

The rest of the day went by just as easily as it had been since I'd started wearing my heels to work. Yes, it had only been a few days but the difference in my attitude and how simple my work days seemed to be, proved that first wearing my heels and now a full set of lingerie distracted me enough, pulled my attention away from what was making work so terrible, that it was once again easy. And Peyton was at the center of that. Every time I saw my heels or felt my cock lurch inside its new cage, I thought of her and her olive skin, her chocolate eyes. I could almost smell the scent of her floral perfume and wondered if I should be wearing it as well.

Gayle left, and I found myself surprised that I was ready to leave to. That toothache, that ringing in the ears, the distraction of my heels made it so that I wasn't behind when the clock hit five. I was ready to leave as Gayle was telling me she'd see me the next day, once again commenting on the warmth in my skin and the glow that I seemed to carry. "You never did tell me her name."

"Peyton."

"I can't wait to meet her."

I smiled, not yet ready to share but wanting to show her off just the same. "You will."

"Good. See you tomorrow Mister Sweet."

"You too, Gayle."

And just like that work was done. I waited a bit, both making sure I wasn't forgetting anything and letting my office building empty. I still wanted to hide my heels as much as possible. I wasn't ready to answer questions that I knew would be coming if my heels where discovered. I still held onto the assertion that they would be. I decided I needed to talk to Peyton. Maybe I should bring up the subject to my staff, let them know what was coming and I had no doubt that Peyton and I were working for a goal that I hadn't even realized I had. I wanted to wear a skirt to work. Or a dress. Definitely not pants. I'd somehow progressed from panties as a necessity to a full-on crossdresser. How I couldn't say. Yes, Peyton was the catalyst, but I don't think she was the source. Once you open a box you can't unsee what was lying inside.

I left the office and drove straight to Peyton's. She'd been disappointed that I was without my heels when we met the night before and I found that I didn't want to disappoint her. I wanted to make her happy. Seeing a smile lighting her face made my own mood elevate to something atmospheric. I made it to her house with ease and was delighted to find her car in the driveway.

At the door I rang the bell. Peyton opened the door, smiling, and let me in. She looked at my feet with the same intensity that Gayle had given the modesty panel of my desk. "You wore them for me."

I nodded and told her that that thought had entered my mind.

At that she gave me a deep kiss with lots of tongue and roaming hands. Her fingers slipped downward and undid the buckle to my pants. I felt her unfasten the latch at my waist. I felt her unzip the fly and a moment later my pants were at me knees. She took in my polka-dotted panties, she took in the white garter belt and the jet-black stockings. She toyed with the hem of my camisole. "I knew you were going to wear those."

"You did?" I wondered what that meant for our evening. Did she wear the same pair hoping to reward me or did she choose a different pair to amplify my frustration? Another question traipsed through my mind: which one did I want?

She tugged her scrubs down to reveal that she was wearing the exact same pair as me. I cheered. I hadn't meant to, but I did. Peyton burst out laughing, bringing one hand up to her mouth as if to stifle her merriment. She stepped backward, nearly tripping on the scrubs at her ankles. She wobbled, bent over and fell to the floor, no longer covering her mouth but now clutching her stomach as huge guffaws escaped her lips. She mocked me, making that same raucous cheering sound I made. Her mirth was contagious, and I found myself laughing right along with her.

It took a moment, but she finally stopped laughing long enough to wipe her damp eyes. Peyton giggled, cheered like I had, giggled some more, but it was a lot less explosive. She was laughing and smiling and taking me in. Breathing heavily, Peyton climbed to her feet, "dinner can wait," she said, kicking her scrubs to the side. She reached out and pulled me after her.

She led me to her bedroom and had me lie on her bed. She helped me take off my pants, working the hem past my heels. She unbuttoned my shirt and helped me throw it aside. With my male clothes on the floor, Peyton pulled off her top, standing above me in her bra and the panties that matched my own. I saw the key to my cage hanging from a gold chain around her neck. My eyes were glued to her fingers as she unfastened her necklace. She climbed into bed with me and unlocked what had been trapped all day. I responded to her touch in a way I couldn't help to do.

Lying next to me, Peyton said, "do what I do."

Her hands caressed her breasts through her bra. I parroted her movements, caressing the lacy cups of my bra. Peyton nodded and when her hands slid down her body to dip into her panties, I did the same, reaching my hand lower to caress my turgid cock. Peyton let out a little moan as her fingers reached that sensitive part of her. I grabbed my cock, feeling the hard heat of it. Peyton pulled her hands from her panties and slapped my errant hand. "No. Like I do." Her hands slipped back into her panties and I followed suit. She rubbed herself in fat, slow circles. I tried to do the same, but my anatomy was different. I rubbed my hand against the base of my cock, trying to copy Peyton's movements.

Peyton's hand moved faster against her pussy and my hand came up to once again grab my cock. I had not planned on it, but I simply did what came naturally. Peyton stopped me in a flash, her hand once again slapping mine. "No, like a woman. Only like a woman from now on."

And that's what happened. I masturbated like Peyton, my hand making rapid circles on the hard flesh where the underside of my cock met my balls. Peyton kept an eye on me and I kept my eye on her, savoring the languid, steady build up. "Yes," Peyton moaned, her back arched, as her fingers pleasured her body and my overly excited mind. I rubbed my cock like a woman rubbing her own wetness. My fingers made strong, quick circles. My cock twitched and throbbed and begged for more but every time my hand came close to encircling my shaft Peyton was there to correct me. "Like this," she moaned, rubbing herself again. "Like me." Her breathing was coming faster now as her fingers became a blur. She flailed about, kicking the comforter off the bed. My hand matched hers, rubbing with a furious intensity. I could feel my pleasure mounting in a way that was both erotic and unfamiliar. My cock twitched and lurched and my fingers moving in a rapid-fire circle against the base of my erection. My panties seemed to stick to the back of my hand.

Next to me Peyton was gasping for air. She lurched and gasped and screamed my name. I kept going, rubbing as fast as my tired fingers would allow. I wanted to grab my cock; I wanted to stroke myself like I'd done so many times, but I didn't. Peyton wouldn't allow it, that much I knew but it was more than that. "Like me," she'd said. "Like a woman." That was such an erotic thought that I wanted to keeping going as Peyton had commanded. I wanted to know how it felt.

Peyton, panting and trembling next to me, watched as I continued to rotate my fingers against my erection. I felt the pleasure climbing at a glacial pace, rising and rising. I thought I was going to come but instead my body jerked and the pleasure waned a pace, forcing me to keep going. Slowly, oh so slowly, I felt the pressure build until finally, with Peyton watching in rapt attention, I came, a thick, mess shooting from my cock to splash my belly and a bit higher to stain my new bra. I reached up to stroke my cock, but Peyton was there to slap my hand away. Tingling with need my hand went into my panties and down to the base of my shaft again to keep rubbing, my hand sliding up and down now instead of making rapid, needy circles. A bit more leaked from me until I was lying sated next to Peyton, my eyes closed, my chest rising and falling as my rapid breathing slowly returned to normal.

Peyton snuggled into me, not caring about the mess I'd made. She kissed my naked shoulder. "Always like that," she said authoritatively, "like a woman. You're my girl now."

I liked the way that sounded or maybe I liked the way Peyton said it and maybe those two things were the same. I nodded in agreement.

"Good."

We took a shower. Drying off, Peyton locked my cock away again, putting the key back on her necklace. I liked the way it looked resting between her lovely breasts. Dressed again, me in everything I'd wore to work but my bra that was hanging in Peyton's shower to dry, and Peyton wearing panties and a sweatshirt from her alma mater, LSU, we finally had dinner. I told Peyton about my day, regurgitating how I was certain that Gayle had seen my heels.

"Well, did she say anything?"

"No."

Peyton giggled, "Poor Sweetness. I guess you're stuck wearing your heels."

"I guess so." I admitted my fears, not afraid to be honest with her. Maybe I'd grown since Linda and I divorced or maybe it was my growing affection for Peyton, but I wanted to be honest with her. I wanted her to know exactly what I was thinking and feeling and how one affected the other. She listened and smiled, touched me both appropriately and inappropriately and when we finally said good night, we'd made plans to kick things up again.

Tomorrow after work we were going shopping.

Chapter 7

Head to Toe

(1)

Once again, I didn't get much in the way of sleep. The cage locked on my body had an odd way of making itself known at the most inappropriate times and I'd been woken up by the cage letting me know it was still there about half a dozen times during those long, lazy hours I should have been sleeping. I had had a hard time falling asleep remembering Peyton's assertion that after work we'd be going shopping and this time for more outer wear.

I sat up, leaning against my headboard and pondered the implications of where Peyton was leading me. She was clearly interested in my crossdressing, maybe as much as I was. She seemed to take great delight in what I wore, and it was obvious she enjoyed choosing my wardrobe. I had to admit that I enjoyed it too. Maybe it released me from the responsibility of my actions. If I didn't pick what I wore than I couldn't be responsible for getting caught wearing my lingerie or my heels. Maybe that was childish, of course the overarching responsibility was my own, but if Peyton choosing my outfits allowed me to justify doing what I had long ago wanted to do, then what was wrong with that?

That led to longer, deeper thoughts. I had loved panties for as long as I could remember. When I was eighteen my family went on vacation and I was left alone for the whole week they were gone. Our house had a sump pump that had yet to be replaced even though it was badly in need of repair, and so when it rained someone had to go outside, life up a plastic garden gnome to reveal a single rusty valve that needed to be turned. My father hadn't wanted to leave the house unattended, and I was old enough to stay home alone, at eighteen I was technically an adult, even if school wasn't quite finished. At that point, it turned out to be the best vacation of my life. The day after my family had left, I'd gone into my parent's bedroom and tried on every dress my mother owned. Nothing I wore calmed me as much as panties did, but the elicit thrill I got told me that I enjoyed wearing women's clothes much more than I enjoyed my own.

I hid that side of me as best I could, settling for panties alone, but over time what I owned and what I wore had escalated. Once when I was about nineteen, I'd jumped a fence to steal a sexy pair of lime green panties from some stranger's clothesline. The way I felt wearing panties, how it both calmed me and aroused me at once, had led to me trying on other things. I bought panties, of course, and my heels. Once I bought a dress but had to get rid of it the same day it arrived for fear that Linda would find it. I bought skirts and stockings, bras that didn't fit around the chest and one with empty cups so big that only cantaloupes would fill the void. Over time I'd purged it all. Everything but my panties. And for the longest time that was enough. My panties relaxed me and calmed me and just hiding them from the world, spotting attractive women and smiling at the thought that my underwear was prettier than theirs, kept my spirits high enough that I didn't really need to purchase anything more.

So why was the idea so enticing that I wore even more to work? Wasn't a properly fitted bra, stocking attached to the delicious straps of a garter belt, a simple silky camisole and heels enough? Normally, during the Linda years, it would be far too much. Linda barely tolerated my panties, everything else would send her into apocalyptic rage. So why wasn't it enough now? Why did I want more?

Was it Peyton? She was enjoying having me be her crossdressing Ken doll, but was it more than that? She helped, there was no denying that. It's what I wanted as well. Maybe the two mixed together become something far stronger than either of us separately. We were like a two-part epoxy that needed to be intermixed to become something powerful. It was fun, scary, exciting, arousing, kinky and so many other things rolled into one and we both wanted it. It was like some fruity concoction, a Cosmopolitan ordered at a restaurant perhaps. Mix well and enjoy.

"Fuck it," I said.

I got out of bed, took a shower and stood in front of my panty drawer. It was full of the panties Peyton and I had purchased. I pondered the blob of colors. Which ones would Peyton choose? Did she go through this same consternation, this hemming and hawing, trying to decide which ones were best or did she just grab a pair and move one. Panties for me were a delicious novelty. For Peyton they were the norm. Adding in our game made my choice even more impossibly fun. I'd be rewarded if I chose the same pair she did. Yesterday she had picked the most feminine pair, thinking I would. Or maybe she knew I would; she was learning all about me. Which pair would she pick today?

I grabbed the peach colored pair. I liked them. They were soft and silky with a sheer backside. The little bow in the front and the lace around the waist added to their appeal. Peyton had sent two pictures the day before, the peach pair and the red thong, so I thought maybe those would be on top. With nothing else to go on I could only use what little information I had.

I pulled the panties up my legs, smiling as I did. Was Peyton wearing the same ones? I'd find out after work and was looking forward to the discovery. I donned the same simple white bra from the day before. After washing it yesterday I knew it was okay to wear again. I chose a different camisole, a simple black one with thin spaghetti straps and a ribbon of satin decorating the bottom hem. The camisole was shorter than my t-shirts, ending about three inches above my panties. A black garter belt and jet stockings completed my underwear.

I got dressed in a dark suit with a black buttoned shirt. A white shirt wouldn't conceal the dark camisole underneath. My pants and jacket followed and then it was time for my heels. The chastity cage seemed to shrink as I donned my heels as my mind took in the implications of what I was wearing and how arousing I found it to be. If I got such a thrill over Peyton choosing my lingerie, wouldn't it follow that I'd like her choosing my outwear as well? I wasn't sure, but I wanted to find out.

I was playing a treacherous game. It was only a matter of time until I was discovered and then what? I was the boss so nothing could be done to me but what would happen to my business? My excited mind latched onto that thought and refused to let go. Business was booming, rising farther than I'd ever imagined, so was I taking a risk by playing these games with Peyton? I doubted I would lose any customers; my staff dealt with them more than I did now. I was the CEO, I had salesmen and women that handled garnering new customers and I had advertising executives that did the bulk of the true writing. But, would my employees leave because they didn't want to work for a sissy or a faggot or whatever other derogatory name filled with misunderstanding or derision was thrown about these days? Most crossdressers weren't homosexuals and who cares if they were? Still, somehow there was this stigma, and would that cause my employees to leave? I didn't want to think so, but I couldn't be sure.

Right now, it was a game and only my heels were noticeable. I could easily play it off as a lark, a playful game between two new lovers. But if this escalated could that excuse fly? Heels were one thing. A skirt or a dress was something else entirely. I scolded myself for sabotaging a game Peyton and I hadn't yet played but I couldn't shake my racing thoughts. I knew the company policy concerning discrimination. When I'd hired Amber and Clayton it was one of the first things they did. "You don't want to get sued, Mason. Discrimination is big," Amber had started.

"Probably the biggest issue that an HR department deals with," Clayton finished her thought. When we'd wrote the policy, using the federal regulations as the guidelines, I hadn't imagined that I'd been writing them to protect me. The irony of it made me chuckle but there was no merriment in it. It was a nervous laugh and nothing more.

Fully dressed, I left the house, my thoughts tossing and tripping through my mind as fast as a rocket leaving the earth. I had a problem that needed to be addressed. Funny, every solution I came up with avoided the simplest. Stop playing the game Peyton and I were playing and return to normal, with only my panties hidden from view. The thing is, I didn't want to stop. I wanted to see where things were leading. Maybe rolling the car had done more damage to my brain than I thought. No, I knew that wasn't true. Peyton was enjoying the game and I was enjoying her. It was more than that. Maybe I was tired of hiding my true self. Whatever it was, I had a problem that needed to be addressed.