Sweetness - Chapter 7 – Part 2

Sweetness

By Mike

Chapter 7 – Part 2

(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?