Sweetness - Chapte 6

Sweetness

By Mike

Chapter 6

Like me

I woke up groggy. I woke up about a dozen times throughout the night as my cock tried and failed to become erect.  I had read about this nocturnal discomfort, but I’d never thought I would experience it. I must admit that I found the situation arousing which didn’t help. I was living an erotic catch-22. The chastity cage excited me, frustrating me and causing my body to wince as the cage was pulled away from my body as my captured erection succomed to the hard exterior of the cage, which aroused me. It was an interesting, exciting, frustrating, intense, and electrifying experience. That Peyton was in charge of it made it even more so. If I had known how much fun the cage could be, I might have ordered one years ago.

I got out of bed and found a picture on my phone. It was from Peyton. There, spread out on her bed, was a cornucopia of pretty panties. Every pair we’d purchased the day before was lying on her bed like soldiers on parade. The caption she’d included read: decisions, decisions.  She followed it up with a little yellow face winking one eye.

I smiled. I couldn’t help myself. She was toying with me, taunting me, tantalizing me. I could feel the cage become tighter as I imagined Peyton slipping a fresh pair of panties up her long, toned legs. I could see her adjusting them against the clean-shaven flesh between her thighs. I felt my imprisonment becoming tighter as I thought of each pair of panties that picture portrayed and how I owned an identical pair.

I took a shower, thinking of Peyton and what panties she was wearing. I shaved my face and brushed my teeth wondering what pair I would wear. It was a fun distraction that kept me from other, scarier thoughts, but it couldn’t banish them completely.

Leaving the shower, with a towel wrapped around my waist, I went to the dryer and pulled out my own collection of panties. Hidden in that pile was the same pair that Peyton was wearing and my reward for matching whatever pair Peyton chose was a reward worth winning. I pawed through the panties, imagining each of them on Peyton’s lovely body, how they would cup her ass or caress that smooth, warm cleft between her legs. Which pair was she wearing? Did she send me those two pictures last night, the one with the red thong and the one with in the lovely peach color, as a clue or were the pictures a way to confuse me and hinder my decision. Whatever, my decision wasn’t coming easily. I picked up one pair, looked at them, set them aside and picked them up again. I didn’t have any idea what pair Peyton was wearing so I would have to go on blind luck alone.

I picked up the pink pair with little white polka dots. Of all the ones we bought they were my favorite. The color was decidedly feminine and that appealed to me; the polka dots made them fun. Had Peyton picked the same panties? I’d find out later and be either rewarded or frustrated. No, I’d get a reward. Peyton promised me that we’d still have fun only I wouldn’t be allowed to come and why the hell did that thought arouse me even more than the panties I was now wearing?

I went to my bras next. My little 38A’s.  We’d only bought four and looking at them I couldn’t imagine wearing one to work but that was what I was going to do. I grabbed the simple white one. I figured I would start slow and pick the least conspicuous one. I fastened the trio of latches in the back of the bra at my nipples and then spun the bra around so that the clasp was centered in my back. I worked my arms through the straps and settled my bra into place. There I stood, a submissive man wearing a locked chastity device, a pretty pair of pink polka dot panties and a simple white bra. At that moment there wasn’t anything masculine about me. My trapped cock lurched at the thought. It was like I had been somehow cheating myself by only wearing panties. There was a whole world of feminine clothing that I seemed to enjoy. Why hadn’t I noticed that before?

I pondered that last question and came up with an answer. My failed marriage. If Linda had been supportive of who I was, or maybe who I was hiding from myself, then maybe I’d have discovered what I should have known was there. Peyton not only accepted me and my growing fetishes, but she seemed to not only enjoy them but complimented them as well. She liked what I liked, and she was willing to lead me when I wanted to be led.  

The camisoles came next. Like the bra I chose a simple white one. I pulled it on, liking how it felt on my skin and how it seemed to hang on me. I looked at myself in the mirror. A man clad exclusively in women’s underwear. Somehow, I wanted to keep going. I gathered up a pair of stockings and a garter belt. The garter belt, like the bra and cami, was white though it was more lace than anything else. Four little streamers hung low, waiting to clasp my stockings.

I opened the package marked Jet. I typically wore black socks to work so I reasoned that black stockings would blend into my heels and pants and wouldn’t draw the eye like a pair of white stockings would. Sitting on the bed I gathered one stocking into a ball and worked it up my leg. Little hairs stuck through the fine netting, looking out of place, but the electric tingle I got sliding the stockings into place reminded me again of the cage Peyton had locked into place. Everything I put on sent a tug of arousal at that captured part of me. There was no denying how excited I got with each additional piece of women’s clothing.

With both stockings in place I affixed the garter tabs to the lacy tops of the stockings. The tabs were simple round pips that slid downward from a wide gap lower into a snug loop. I did the two below my ass and then the two in front. Standing up I felt the taut pull of the garter suspenders. I couldn’t help myself. The feeling was so delightfully enticing that I had to shorten the suspenders to maximize that electrifying taut pull. I paced my bedroom loving how the garter belt felt tugging on the stockings.

I felt a little disappointed when I donned my work pants and buttoned on a shirt. I didn’t want to wear a blouse and a skirt, well maybe I did but I couldn’t, but I did feel a pang of sadness when I had to hide my lingerie from the world. I couldn’t face my office in my underwear, my visible heels were bad enough, but covering my bra and panties, garter belt and stockings made me feel just a tinge of sadness. Still, putting my low heels on erased that feeling and replaced it with one of terror again.

It was amazing how quickly I went from an amazing high to a different, agonizing low. What was going to happen when someone at my office found out about my heels? I had focused on that question for far too many hours and just slipping them onto my feet, while arousing if my chastity cage was any indication, was also frightening. Those heels, the only part of my feminine outfit that wasn’t hidden, once again raced to the forefront of my thoughts. Who would notice them first and what would I say when I was called out on my choice of footwear?

My mouth went dry and I could feel my pulse against the ring that encircled my trapped cock. I walked into the bathroom and looked at myself in the mirror. Besides the blush on my face I didn’t look any different than normal. I couldn’t see my camisole, my bra or panties. My garter belt or stockings were hidden from view. Only my heels looked remotely out of place. Still, a small smile did flash across my face. I was wearing more women’s clothing than men’s.  That thought astounded me. I knew that one day soon I’d be clad in women’s clothing exclusively. Peyton had hinted at that and I found the idea both scary and enticing. I wanted it to happen while at the same time I wanted to avoid it altogether. That internal battle was both overwhelming and impossible to ignore. Suddenly I wanted to be wearing a blouse and a skirt. Peyton had somehow ignited what Linda had doused. Just as quickly I wanted to run from the idea, my own fear extinguishing the idea.

I combed my hair and left the bedroom. I gathered my keys and wallet and cell phone, putting them in the same pockets I always did. The thought that I’d need a purse flashed across my brain, causing me to shake my head at the idea and smile at the same time. It was a silly idea and one that seemed to fit.

I walked out to my SUV, enjoying the clip-clop-clip sound my heels made against the concrete. As usual, I was the first in the office and I was happy about that. No matter how excited what I was wearing made me, the idea of being discovered scared me even more. Not that my captive cock understood that concept. The way my cock pushed against my pink, feminine panties, you would think that I was anxiously anticipating the day I got caught so I could escalate my eventual descent into wearing more outwardly apparent women’s clothing. Like skirts and dresses. I wanted to wear them, not pants - no, skirts and dresses. Blatantly feminine attire. I’d not realized it until now, sitting at my desk, feeling the uncomfortable tightness of my cock cage and savoring the delicious tug of my garter belt. Feeling those things, feeling distracted by those things, made work somehow less daunting, less oppressive. It was like work became something I could endure if I was wearing armor and my armor of choice was bras and stockings, panties and camis, skirts and dresses. Somehow, I’d become more of a man by wearing women’s clothing.

Gayle came in, gave me a smile, and asked me about my night. Polite office small talk.

“Great. How was yours?”

“Who is she?”

That took me aback. “I’m sorry.”

“You’re smiling. You never smile. Well, not for a while. So, who is she.” I stammered out something but Gayle just grinned. “Uh huh. Well, that answers one question.” She looked down as if she could see through my desk. “And I guess that explains other things, too.”

Did she know about my heels? It seemed to me that she did but she didn’t comment on them. She just said, “Well, I can’t wait to meet her.”

I mumbled a response, but I couldn’t focus on what she was saying. They way she had peered at my desk, like she was seeing what the heavy wood hid, had me distracted. Did she know? Would she say something? Anything? I felt my balls twitch inside their rigid prison, trying to protect themselves from what I couldn’t say. I just felt the twinge and felt a knot of pain halfway up my spine. My office suddenly felt cloying and far too hot. Had I been discovered? I thought I had but since Gayle had left, saying something but for the life of me I couldn’t remember what it was, I had no way of knowing. 

I picked up my phone and sent Peyton a text: I think my secretary knows about my heels. I brought one foot up to my lap and unbuckled my left heel. I stopped myself before I removed my shoe and sent Peyton another short message. Does that mean I can take them off?

I waited for an answer but didn’t receive one. Peyton had told me that she kept her phone tucked into her purse during her work shift. Something about hospital policy that those involved in patient care weren’t allowed to carry their phones. It meant I had to wait. Well, I didn’t have to, but I had to just the same. It was still Peyton’s game and even if I thought I was losing I had to play to the end.

I got to work, and my work day flew by. Problems that seemed insurmountable before I met Peyton were so much easier now that I had the terrifying distraction of my heels and everything else I was wearing. I liken it to tinnitus, the incessant droning in your ears that you can’t shake or hide from. Or maybe it was like a toothache, a throbbing pain that wouldn’t go away and kept you distracted from so many other, smaller things. My lingerie and heels were exactly like that. A background concern that seemed to mask the problems that had made me loathe coming to work. There was a sexual component to be sure; it was sexy as hell to be a man wearing women’s clothing and I found myself enjoying the thought of wearing even more even if the only thing left was the outer layer, but it was more than that. It was Peyton deciding the rules of the game, it was the delicious naughtiness of wearing not just panties but so much more and wearing them to work made it even scarier and somehow more fun, too.

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.