Chapter 7 – Part 1
Head to Toe
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. I’d stolen my mothers’, my sisters’, and once when I was about twelve or thirteen, I’d even jumped a fence to steal a sexy pair of lime green panties from some stranger’s clothes line. The way I felt wearing panties, how it both calmed me and aroused me at once, had led to me trying on other things. When I was sixteen 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. It turned out to be the best vacation of my young 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. 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.
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?”
“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.
He laughed, “you should see your face. I take it this is a big deal to you?”
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.