Sweetness

I got to work before everyone else. I made the coffee, surprising myself by how simple an earlier nightmare had become. I no longer worried about shuffling my feet to the bathroom. The first few days of wearing my heels I'd hardly drank anything. Now my heels were second nature and after such a short amount of time. It amazes me what a person can get used to. Did wheelchair bound people feel the same way after enough time had passed. Did a wheelchair become as much a part of them that they don't think anything of it? I kinda hope so.

Peyton texted me, taunting me with a very dark picture of her crotch with her scrubs pulled away from her body. I couldn't see what panties she was wearing but I could imagine the view that wasn't quite revealed. Which ones did I wear?

You tell me.

A smiley face sticking out a tongue came back.

We sent a few more texts. Peyton ended it with a pair of big, red lips and a note telling me she'd see me after work.

Looking forward to it. And I was. Despite my fears and my consternation, I wanted to continue. I wanted to be led where Peyton wanted to lead. After all, she was doing the thinking for both of us. That thought made my trapped cock pulse.

I sent an email and a minute later I took the bull by the horns as the old saying goes. Clayton came into my office, "You wanted to see me boss?"

"Where's Amber?"

"Dealing with Blue Cross. I think our insurance rates will go down next year," he shrugged but flashed a warm smile, "I don't know how she does it but she's amazing."

I tilted my head. Clayton got it. "A good woman props you up, doesn't she?"

Clayton's grin got bigger. Whatever he was thinking it sure made him smile. "Yes." He considered me for a moment. "You met someone?"

My business isn't so big that I didn't know everyone and heading the HR department with his wife Clayton was just as informed. "You could say that."

"Is that why I'm here? Are you getting married?"

"Not yet," I said but that made me pause long enough to think that maybe I would one day. Probably to Peyton. After Linda I'd been content to not date, to just live my life alone. It was a good life and I'd been happy, but now, with Peyton I was happier. The great thing about life is it can always get worse, but it can always get better, too. Clayton waited until I caught up with my thoughts. "It's just," could I do this? Should I?

"What is it?"

I had been worried that Gayle knew about my heels but if things progressed, and I thought they would, then my heels were the least of my concerns. Was I doing more harm than good by attacking a problem before there even was an issue? I wasn't sure but now, with Clayton standing in front of me, I was committed. And that was fine. A sickness treated was better than a disease left to fester. I brought my feet up and put them on the desk. My pants rode up, revealing the jet-black stockings underneath. I'd been worried about Gayle seeing my heels and now I was showing them to Clayton. What would he think when I didn't exactly know what I was thinking?

He looked at my face, my heels, the stockings and my face again. "Nothing to worry about," he said.

"Really?"

He laughed, "you should see your face. I take it this is a big deal to you?"

Duh. "Duh."

Clayton laughed again. We chatted, Clayton pulling up a chair. When he left my office, I felt better about a lot of things. Maybe society wasn't ready for a full-on crossdressing epidemic, but it seems my office was. "I would recommend you, shall we say, come out to the staff. Maybe send an email. Facts are way better than gossip."

I thanked him and then called Gayle into my office. I'd been afraid of her seeing what I was about to show her. Was I crazy? Maybe. Was it the right thing to do? I didn't have an answer for that. Clayton convinced me that it was so I took that as a sign that I was on the right course.

"Oh, I saw them on Wednesday," Gayle said. "And again yesterday. I figured I'd see them again today. You shuffling around like a zombie in The Walking Dead was suspicious and with a quick glance at your feet I knew what you were doing. That and you couldn't really hide being suddenly taller." She giggled, "they're lovely," she added.

I explained my heels and what was probably coming. She seemed to take it all in the way a doctor takes in everything their patient is saying. She tried to be stoic, but she was smiling larger and larger as I went on. Finally, she said, "I can't wait."

By the time the day had ended I wondered if I'd done the right thing. That old saying that you can't unring a bell raced through my brain time and again. I was committed even if I didn't want to be. What would Peyton think and why hadn't I included her in my decision? I scolded myself for that. This concerned her, and she deserved to be involved. I berated myself as I drove to her place and I mentally spanked my own ass as I parked in her driveway. Of all the things I had done that day, coming out first to Clayton, then to Gayle and finally sending an email to my entire staff both reminding them of our discrimination policy and what changes they were likely to see in me, the fact that I'd omitted Peyton from any of it stung that most.

"I'm sorry," I said the moment Peyton answered the door.

She saw something on my face, "What's wrong? Sweetness, what's wrong?"

I felt a wave of sadness wash over me, like a heavy morning fog obscuring a tall skyscraper. I suddenly felt horrible, like I'd done something terribly wrong. At the time I had merely been solving a problem now it felt like I had somehow hurt the woman I was growing attached to.

She led me into the dining room, took a seat next to me and then clasped my hands in hers. "Mason, what's wrong?"

I felt tears in my eyes. Had I hurt her? Had I hurt us? It took about ten minutes for me to get it all out. At the beginning of my story her eyes showed concern, by the end she was smiling. "Oh, you gorgeous, silly man." She stood up and threw her arms around me. She kissed my forehead, my nose and both my damp eyes. "You," a kiss on one eye, "silly," the other eye, "silly," the first eye again, "man," and back to the other. "You had me so worried."

"I'm sorry," I said. I followed that with a sniffle.

"Don't be. You had no idea how much this means to me?"

I didn't understand, and I told her that.

"You're crying because you thought you hurt me. That..." Peyton kissed me again, "that means everything. You have no idea."

I thought I understood what she meant, and I felt the two of us growing even closer. If I hurt that much just imagining how much I hurt her, then the two of us were connected in a far deeper way than I had realized. Maybe Peyton didn't quite feel about me the way I felt about her, but the sadness on my face and the way my lips quavered, told Peyton how far we'd come in just over a week.

She kissed me again and then pulled me to my feet. "Go wash your face. We're going shopping," she said. "I'm going to change."

"Need any help?"

She flashed a radiant smile. "Nope. I'm not ready for you to see my panties." She mouthed the last in a breathy whisper that made my captured cock take notice.

I smiled back, wiping my eyes with my jacket sleeve. The time for unexpected tears had passed. It was time for fun.

(2)

It was Friday night and the mall was packed. Countless people milled through the concourse, passing stores filled with toys and clothes, jewelry and vapes, electronics and books. Peyton was wearing a simple white skirt that ended just below her knees. She was wearing a tan blouse with a single, large button at the base of her skull. Her hair was pulled into a pony tail that bounced from side to side as she walked. She was wearing a simple pair of tan flats.

I was wearing the same suit I'd worn to work and of course the heels were still on my feet. They weren't locked on, but they might as well had been. Peyton hadn't let me change, smiling devilishly as I protested. "Don't worry about it Mason. I'll keep you safe."

We walked into the mall. Peyton had a goal and after my work day it seemed I now shared it. I still couldn't understand what had prompted me to take the steps I'd taken. Had it simply been a problem that needed to be solved or was there something else, some underlying need to dress more outwardly as a woman. Was I a full-on crossdresser? If so, why had I been content to wear panties almost exclusively for as long as I could remember?

We walked through the concourse, Peyton's arm draped in mine. We were two lovers out for a bit of fun. My heels were making that lovely clicking sound but in the din of the mall it was barely noticeable. I was hidden amongst the throng of people going about their evening, oblivious to anything that didn't concern them. It was at that moment that I truly understood the adage of hiding in plain sight. My shoes were visible as was the color on my cheeks, but nobody paid me any attention. I might as well of been invisible. Would that change when I wore something else, like a skirt or a dress, I couldn't say but somehow, I was certain that I wouldn't be invisible after that.

Peyton led us into an Anne Taylor Loft. Skirts and dresses and blouses and slacks hung from circular racks. The clothing was stylish and professional. It was a store where professional women bought professional clothes to fit in at the board room or amongst high-powered CEO's. Nothing trashy jumped out at me. A young woman approached Peyton, mostly ignoring the invisible me. "Hi. I'm Mona. Can I help you find anything, miss?"

Peyton, eyes wide and sporting a huge grin on her lovely face, said, "We're looking to expand Sweetness's wardrobe." She nodded at me.

Mona's smile faltered but came right back. I guess she worked on commission. "Of course. What are you ladies looking for?"

I didn't know it was possible, but my blush grew even darker. I swallowed, afraid to speak. But, down below, it was obvious I enjoyed the shame I was feeling. Peyton did the talking, explaining how I owned my company and I needed to wear a certain style. Mona was nodding, her eyes scanning me from head to toe. "That won't be a problem. Do you know your size, miss?"

First 'ladies' and now 'miss.' Did it help her to serve a man by using those words? Maybe it did and what did it matter? I would be dressing as a lady or a miss, so I guess the words Mona used worked just fine. I shook my head. My mouth was far too dry to speak.

"That's okay," she was smiling, and it appeared genuine. I guess she was over the initial shock and a sale is a sale. I'd learned that simple lesson when I started my business, taking on every job I could get. Now that I'm more established I can afford to be a little pickier in the jobs we accepted but at the onset I would try to sell shoes to a double amputee if it put food on my plate. "We'll get you set up in a dressing room."

She led us through the brightly lit store. A few women were shopping but they paid no attention to me and the lovely woman at my side. Why would they? A woman was shopping with her spouse in tow.

Mona escorted me into a dressing room. Peyton, all smiles, told me to get comfortable. "We'll be back soon. Why don't you get that suit off?"

It was an order and the downstairs tightening let me know I enjoyed her bossing me around. But I knew that already. I didn't really need the reminder.

Mona and Peyton left me alone. I stripped out of my suit and stood there, bouncing from foot to foot, wearing nothing buy my lingerie. I was a man, I could feel the proof of that struggling to grow inside the confines of its cage but at that moment I was also a lady shopping for a nice, new wardrobe. Well, Peyton was shopping, I was just waiting around to be her living mannequin. And it was exciting. I winced as the reality washed over me, my knees coming together as that tiny cage grew tighter as I swelled against its unforgiving embrace.

Peyton returned with Mona in tow. Both women had their hands full. They were carrying dark suit skirts and crisp white blouses. They hung the clothes on a pair of hooks. Mona left, after giving me a knowing smile at what I was still wearing, leaving Peyton behind to help me get dressed.

I can't explain the excitement I felt. Peyton and I played dress-up and I felt an electric current racing down my spine as I stepped into my first skirt. Goosepimples broke out on my arms and the little hairs at the base of my skull stood up straight. The chastity cage grew so tight that I was certain it was leaving permanent marks in the skin. Peyton, still smiling, took it all in. Grinning evilly, she pulled up her skirt, showing me her panties. We didn't match, but just seeing them and realizing their implication made that chastity cage distract me even more. I was horny, fueling some long-dismissed fantasies, and now, at that moment, Peyton let me know that I was in for a long, frustrating night. I moaned causing Peyton to laugh.

I tried on the skirts and the blouses. They were stylish and neat and fully appropriate for the boardroom. I looked like an executive secretary and that thought had me doubling over in unquenched arousal. Gayle never dressed as I was at that moment and it was arousing as hell. My face needed work, as did my hair, but from the neck down I was all business and pretty damned sexy.

Peyton couldn't keep her hands off me. Did she know what she was doing? That she was fueling my desire and increasing the pain in my cock? By the look on her face and the smile toying with the corners of her mouth I thought that maybe she did. But she was doing it for her and not for me. There was a longing need in her eyes and she wasn't about to be denied. I watched as she slid her fingers under her skirt. I watched, my own eyes glued to the performance before me, as Peyton slipped her thin, blue panties down her legs. She stepped out of them, ran then up my skirt, trailed them over my blouse, before dropping them onto my shoulder. Her hands moved higher, grabbing my hair. She pushed me to my knees, stepping forward and flipping her skirt over my head.

I did what she desired, enjoying the scent of her, the taste of her and wincing in discomfort as my entrapped cock struggled against its cage. I savored the illicitness of what we were doing and where we were doing it. The thought that only a simple curtain was keeping our naughtiness from being discovered made it somehow even hotter.

We finished what Peyton started and the blissful look on her face was quite the opposite of the burning frustration etched on mine. I felt the cage pulling away from my body. I felt the rising pressure of need sending shivers along my heated skin. The dressing room felt hot and cold, loud and silent. It was everything and nothing and I was loving every second of it. Normally, in those post-Linda years, I'd take care of myself and it would be done. Now, with Peyton and her locking toy, my sex life, while different thanks to the chastity device, was somehow even greater. The stories I read had told me about this, but feeling it made it so much more powerful. I was nuclear with need and grateful that Peyton was in charge.

Peyton cleaned my face with her panties and then stuck her panties in the pocket of my pants sitting on a little bench next to us. "That was wonderful, Sweetness," she purred, rubbing her hand along my spine. "Thank you."

"You're welcome."

We went back to shopping and by the time we were done I had a full two weeks' worth of office wear, all skirts and blouses. Peyton knew, or maybe I had let it slip, that I didn't want slacks. The more feminine the better was the motto that we seemed to follow.

Mona was satisfied with our purchase; we'd spent over fifteen hundred dollars. She gave us her card and Peyton put it in her purse.

Leaving the mall, me once again wearing my suit, Peyton led me back to Victoria's secret. Another three hundred dollars and I had a few more bras, a few more camisoles, a dozen new pairs of stockings, and three more garter belts. The panties we had covered, and our game was fully in effect.

We left Victoria's secret and returned to my SUV to unload our bags. Sitting in the car, Peyton gave me a lingering look. "Are you ready for what's next?"

"What is next?" She waited until I caught up. Finally, "I don't know."

"That means no." She did not seem to be disappointed, and I loved how she took my feelings into consideration. "We'll go slow, then. When you do this, I mean really do this, and I can't wait," she was giddy as she said that last part, "you'll have to have your hair and makeup done. We won't make a mockery out of you, Mason. We won't."

It had never once crossed my mind that we would. I told her that and she nodded, with a lovely smile on her pretty face.

"Good."

We left the mall and I took her home. She invited me in and led me to her bedroom. I undressed her, and she undressed me and after satisfying her with my mouth and my fingers, Peyton unlocked the cage and took me into her mouth. I trembled beneath her ministrations and groaned in frustration as she stopped short of my own anticipated release.

Peyton was all smiles as she reached for the cage again. "You guessed wrong, Sweetness. You know the game."

I was both speechless and enticed. The game, already frustratingly fun, had grown into something electric. I waited, my hands balled into fists as my erection waned enough for Peyton to put her lock in place anew. I was needy and achy and while my body longed for more my mind was satisfied. It would be enough.

We said goodnight and I drove home to put my new clothes away. I meant to, but I couldn't help myself. I tried on all the skirts and blouses again. My hair and face were what Peyton had meant when she asked if I knew what was next. If I was to go to work fully dressed as a woman then my hair and makeup would have to match. I wouldn't go as a parody of a woman, I'd go as presentable as I could. Staring at myself in the bathroom mirror, I thought it wouldn't take much. At just over five foot nine inches, I wasn't the tallest of men which helped mask my true gender. My eyes were soft and round and with my cheekbones, I thought that a bit of color could enhance them enough to get the job done. My hair was short; we would need a wig.

I put my clothes away, brushed my teeth and got into bed. The day had started strong and ended stronger. My hand slipped into my panties to toy with the cage that kept me captured. Only Peyton had the key. I somehow enjoyed that idea. It would be interesting to see where Peyton led me next.

I thought of her and how our brief relationship was progressing. I had truly felt sad, so much so that tears had come unbridled, just thinking that I'd hurt her somehow. I was smitten, there was no denying that. Would love come next?

Chapter 8

A First

Five weeks passed in a rush. Each day I would choose my panties and each night Peyton and I would get together to see if I was to be teased and locked up anew or rewarded for guessing correctly. With the number of panties we had, I lost more than I won, but to be honest I didn't know which was better. Either way I was rewarded with only the reward being different. Sometimes Peyton would tease me, sometimes she would have me tease myself, only allowing me female masturbation, slapping my hand if I even attempted to grip my heated arousal. Either way, every time I guessed wrong, I would wind up locked again after coming dangerously close to the precipice of release. Even if the rules were against me, I must admit I loved the game.

During those delightful weeks Peyton and I grew closer. We spent more and more time together. I introduced her to my friends where she fit right in, being as crass as my male friends and as sophisticated as their significant others. I met her friends, finally crashing one of her biweekly dinner parties. She told me the next day that I was "perfect", and I beamed at the praise. It pleased me that I pleased her. "Charlene told me that you're a keeper, which is high praise from her. And Janey gave me her blessing." With that she had given me a little peck on the cheek, then the nose, the lips, and that led to something far more exciting for Peyton. I had not chosen the correct panties that day so our love making, while a tad one-sided, still satisfied us both.