Sweetness

"Now," she said, turning serious, "I'm curious."

"About."

She led me to her couch and sat next to me. The television stared back at me and I could see our reflection in its dark face. She tilted her head and regarded me for a moment. From the kitchen I could hear the soft clicking of a clock. I heard the refrigerator kick on and outside I heard some kids screaming though I couldn't make out what they were saying. I could see Peyton considering something as if she was struggling with a decision. "Toys," she finally said.

I nodded. "Okay."

"I told you I have some, right?"

I nodded again and then smiled remembering her story of wearing a vibrator to work, stuck into the warm recess I'd been in not thirty minutes before. "I remember."

"Wait here," she said. She got up and came back a few moments later. She held in her hand something I'd recognized. I had the internet and I was an adult and I was kinky. When you have a panty fetish and you like how you look wearing women's heels, wouldn't it stand to reason that you knew about other, kinkier things? Well I did, and I knew exactly what Peyton was holding out to me. It was hard and plastic and pink and the shape of a flaccid cock. A small golden key jutted out of a round cylindrical lock built into the device. I wasn't sure of the brand, but I was certain I'd seen a picture of it before. "I want you to wear this for me."

I looked at the chastity cage. I'd seen them and thought about them, but I'd never considered owning one. I'd read stories and found them fascinating. Hell, I've masturbated to stories of men and women and even couples in chastity, but did I want to wear one? The look Peyton was given me told me that not only did she want me to wear it, but the idea excited her almost as much as our shopping trip had. There was this needy anticipating in her almond eyes. I could see her trembling slightly.

"You're shaking? Are you okay?"

"I'm scared."

The tone in her voice at those two words stung, "About what?"

"That I'll scare you away." Her voice cracked, and I melted. How could I not? I was already smitten and if she could accept my fetishes how could I not accept hers? I told her as much and she leapt at me, pushing me backwards. The chastity cage tumbled to the carpet. "Oh, you wonderful man," she said, kissing me passionately. Her hands slid along my stomach, traced along my stomach and came up to wrap around my neck. She kissed me, and I kissed back. It didn't lead anywhere, I was spent already, but it was fun and passionate, and I loved every second of it.

"This is going to be fun," she said.

I still wasn't sure if I wanted to wear it, but I kept quiet. This was now Peyton's show. I'd been leading the parade during my panty fashion show. It was Peyton's turn to lead now. She climbed off me and pulled me to my feet. She picked up the chastity cage and unlocked the lock. The cage separated from an oddly formed ring, almost like a Mobius strip I made when I was in fifth grade so long ago. Peyton instructed me how to put on the ring. I fished one testicle through the loop, winced when I worked the second one through and felt my pulse in my cock when I worked it into the same tiny circle.

Peyton seemed to be trembling again but this time it was for an obviously different reason. "Why do you have this?"

She paused and gave me a serious look. "My last boyfriend cheated on me," she said, and I could hear the hurt in her voice. "I promised to give him a second chance if he wore this. He agreed but when it arrived, he broke up with me instead. I'd already bought it. I don't know why I didn't throw it away." She shrugged. "The idea of it though was something I couldn't shake. I'm glad..." she stopped speaking and stood to kiss me instead. "Thank you."

I gave her a smile and watched as she continued applying the rigid pink cage to my suddenly attentive dick. She sat on the couch, with me standing in front of her and waited until my interest waned enough for her to continue. She placed the cage onto me, working the tapered end into a matching grove. I could feel how tight the cage was, how the hard plastic was holding me in a snug embrace. With the cage fully seated in place, she stuck the cylindrical post into the ring that encircled my captured balls and turned the key. The key pulled free, but the cylinder stayed in place as did the cage. It was locked on. Peyton, her eyes wide, was absorbed in the look of my locked-up cock. "This is fucking awesome!" She had the wide-eyed look of a child entering Disney World for the first time and the exuberance of a boy about to lose his virginity. She was enraptured, enthralled and entertained.

I dropped one hand to tug on the cage. My balls pulled away from my body, but the cage stayed in place with my spent penis fully trapped inside its pink plastic prison. "How long will I wear this?"

She smiled at me, rose to her feet, and kissed me full on the lips. Hard.

I felt my cock twitch, but it couldn't do anything else. I moaned a bit causing Peyton to laugh. "That's up to you?"

"Oh?"

"We'll make a game out of it." She giggled. "Every day you'll wear one of your new panties to work. Tomorrow," she added, "I want you to wear a bra and a cami, too."

I had expected that, so I gave her a nod.

"And your heels. Of course."

Another nod.

"After work we'll have dinner. I'll be wearing a new pair of panties, too. If we're wearing the same ones, we'll fuck like rabbits."

"And if we're not."

"Then you'll make me cum with that talented mouth of yours."

I thought of all the panties we'd bought a few hours earlier. What was it? A dozen pairs each? That gave me a one in twelve chance of picking right. My odds would get easier each day as I would know which pair, she was wearing but then it dawned on me that she would know which pair I'd worn as well.

Peyton laughed, "It's not as easy as you thought is it? I wonder," she was teasing me now, "how often should I wash my panties? Maybe every day?" She laughed at that. "I promise I won't wear the same pair two days in a row."

"Doesn't seem fair," I said but my voice was playful and light. I wasn't being harsh or pouting, I was simply absorbing the fix I found myself in and finding that the game, while lopsided, was exciting and I was looking forward to playing. I didn't know why or maybe I did, and I just didn't want to admit it.

"And guess what else?"

"What?"

Peyton left my side and came back with a new pair of panties. They were light green, the color of antifreeze. Their size told me that they were one of hers. She pulled them up my legs and settled them against my trapped cock. "See how my panties fit now. You won't fall out of them. Just like I said." She laughed at that, a victorious sound, like she'd solved a particularly fiendish brain teaser. The panties seemed to hold the cage snugly against my body. I thought that the panties helped the cage feel more comfortable.

"Much better," I agreed.

She kissed me again. "Thank you, Mason. I had the best time."

I admitted I had as well. We said our goodnights and I went home, the key to my cock staying with Peyton. It was her game and I was enjoying the rules. I knew why. I was submissive. It was one of the reasons I wore panties and heels, and it was the main reason why I let Peyton lock me up and lead our relationships. I didn't need to apologize for it; it's who I was, and Peyton accepted me. How could I not go along when her leading me was exactly what I needed most?

At home I put my panties in the washing machine and got ready for bed. As I was brushing my teeth my phone chirped. It was a picture of Peyton's panty covered crotch. Should I wear these tomorrow? Another picture came in. This one of her ass adorned with a thin red swath of color from her newest thong. Or these?

Let me know and I'll wear the same ones, I texted back.

She sent an emoji of a pair of red lips. Not gonna happen, mister. Then, good night.

Night.

With the day behind me, I put my panties into the dryer and went to bed, worried about what the next day would bring.

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.