Sweetness - Chapter 8

Sweetness

By Mike

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.

Work progressed and was still much easier than it used to be. Gayle commented on my shoes and took an interested delight when Peyton and I would go shopping and I’d buy some different heels. Where once I had two pairs, I was now up to six. The first time I came to work in a new pair of heels Gayle wasn’t shy about letting me know what she thought of them. And that she’d seen them right away. It was true, I never did hide them from her. “Oh, Mason, those are adorable.”

And they were. They were red, with a taller, three-inch heel. A single strap ran over the arch of my foot with another thin strap running from the cross-strap down to the center of the red velvet heel. Shopping for shoes was much more fun when you weren’t worried about hiding them. At the onset I’d only worn my black heels. Now I could wear reds or whites, blacks or my newest golden colored ones. The colors were amazing and far less drab than any pair of men’s shoes that I owned.

I had three purses and two wigs and a huge collection of makeup. Peyton and I were working towards a goal and there wasn’t any rush. My office knew what was coming, as did I. The only variable was the when. Since I had come out to both the HR department and my staff as a whole, I was no longer safe from anyone commenting on my heels. Since I had revealed them there wasn’t any fear of them being discovered. 

“Tomorrow,” Peyton said. 

We were lying on my couch, watching Netflix. Peyton was snuggled into me. I could smell the sweet coconut scent of her shampoo. I could feel the heat of her body next to mine. She fit against me like two Lego blocks snapping together. When she spoke, I could hear a bit of playfulness.  I knew the answer but I had to ask the question anyway. “What about tomorrow?”

“Tomorrow you’ll be dressed fully as a woman. Are you ready?”

I didn’t have an answer for that. Intellectually I was. It was what we were both working towards. Peyton and I had discussed it at length. We had talked about the risks; we’d spoken on the pure enjoyment she would get out of knowing that I was her woman and I’d be dressed as she wanted. Peyton took great delight in leading our relationship. She usually chose where we ate dinner or what we watched on TV. Even now, watching Netflix, Peyton held the remote control in her hand. And I liked it when she led. Running my own company, having to keep so many people employed, where I had the ultimate authority in everything, sometimes felt taxing. It felt good to let Peyton lead. For her it was the opposite. The doctors had the final say in anything; she enjoyed being the one in charge. I think she needed it.

Most of our discussions were serious. Most but not all. The ones that weren’t serious were far more fun and were my favorite. Peyton would taunt me, call me her sissy, her girl, her Barbie. She’d make teasing comments, “Oh, Sweetness, you’re going to be the prettiest girl at the office.” Or, “You’ll make all the boys hot. Do you think they’d like to get into your panties?” Or, “Maybe you should be the secretary.” Sometimes she was vulgar, sometimes she was sweet, but when she teased me, called me her girl or her sissy, my cock would lurch in its tight confines. I loved it when she teased me, and she knew it.

“Maybe,” I finally answered.

“Well, you don’t have any say so you might as well get used to the idea. Just think, tomorrow when you go to work, you’ll be wearing a pretty pair of panties, a sexy little garter belt, stockings, a bra, a blouse and a skirt as well as your heels.” She sat up and climbed from the couch, “I bought you something. Well, a few things?”

“Oh?” I wasn’t worried and even if I were it wouldn’t matter. Peyton was leading the show.

“Come on, we have some things to do.”

She climbed from the couch and pulled me after here. She led me into the bathroom and helped me undress. I quivered in anticipation when she unlocked my cage even though I knew I’d be left wanting as our panties that day hadn’t matched. Smiling and whistling a little song I knew but couldn’t name, Peyton ushered me into the shower. “Shave everything,” she said.

She watched as I turned on the water, laughing when I jumped out of the way of the stream until if got hot.  “Start with your legs,” she said and proceeded to give me instructions. She watched as I set one leg up on the edge of the tub and lathered it with shaving cream. She nodded as I slid the pink razor she’d bought me up from my ankle to my knee. I watched as my leg hair came with it. It was like mowing the grass, taking one long stripe away at a time.

After my calves I did my knees and then my thighs. Under Peyton’s guidance I shaved my crotch anew. Thanks to the chastity device I wore I’d been keeping my pubic hair absent so that area was decidedly less difficult.

“Keep going.”

I shaved my stomach and my chest. My armpits went next under Peyton’s lead. She had me do my arms and helped me shave my back. My skin felt weird and a bit unpleasant. The water felt hotter and when I shut off the heated stream, the room felt much colder. Drying my body every bit of skin felt different and eerily strange. I wasn’t sure I liked it but I did enjoy the way Peyton ran her hand over my legs and made a soft, cooing sound. “Very nice,” she said. She grabbed my hand and pulled me into the bedroom. “Lie down.”

I did.

The first thing she did was lock me up anew, smiling as she pulled the key free of the lock. I could only watch as she put the slipped the key back onto her necklace.

Still grinning, Peyton opened the nightstand on her side of the bed. Two weeks earlier, I’d cleared a dresser drawer for her, opened a stretch of my closet and gave her her own nightstand. I let her know she was welcome and giving her a key solidified the idea that she was welcome in my house anytime she wanted. She pulled out a rather large box and a small bottle that held some thick, viscous fluid. Peyton climbed onto the bed and then straddled my thighs.

Smiling, Peyton pulled the box to her side. She opened it and pulled out a tan colored blob that looked like a chicken breast about to be thrown on the grill. I knew what it was the minute I saw it. Peyton had never mentioned getting me breast forms; I guess it was meant to be a secret. Smiling even larger Peyton pressed the breast form against my right nipple. I shifted slightly at the cold.

“Look how big they are, Sweetness. Oh, you’re going to be stacked.”

And they were big. They weren’t huge but seeing the artificial breast sitting on my chest I had no doubt that they would be noticeable.  She pulled out the twin to the first one and placed it on my opposite nipple. I looked first to Peyton’s smiling face and then down to the breast forms that Peyton was holding against my chest. The thought that they weren’t huge disappeared. Seeing them side by side made them seem outrageous. “How big?”

She giggled, “you men and size.” Her giggling became a laugh which became a full-on guffaw. Somehow, I had cracked her up. “They’re a D cup,” she informed me when she got her laughter under control.  “For your shape they’re the best fit. You’re a little taller than most women and a little more stout.” She laughed at the frown on my face, “You’re not fat and you know it but you’re a man so you’re a bit bigger. This size is proportional.”

I doubted her assessment, but I trusted her. “What’s that other thing?” I knew the answer; I read the internet.

“Glue, silly.”

With that she opened the bottle. She coated the back of my left breast form and did the same to my chest. She waited, rubbing her thighs against my freshly shaved ones. My cock in its tight cage responded and I felt the cloying tightness. Peyton purred at that, enjoying the affect she was having on me almost as much as I was enjoying her affecting me.

She waited about five minutes, just rubbing against me and running a finger over my balls and tapping on the hard cage. She was toying with me, taunting me, teasing me. Distracting me. With both the back of the breast form and my own chest tacky to the touch, Peyton deliberately placed the form on my chest, taking her time, positioning it just right. She repeated the process with my right hand side, smiling the whole time.

“Don’t move,” she said, climbing off me. “Let the glue set.”

“How do I remove them,” I asked, cupping my suddenly heavy breasts.

“You? You don’t. Only I can, got it?”

I knew it was another game and they way she said that proved it. I felt the fire below pulse in response, “yes, ma’am.”

“Good.”

Peyton left the room and came back about forty-five seconds later. In her hands was a fresh Victoria’s Secret bag. She placed it on the bed next to me. I watched, mesmerized, as she pulled out another ten pairs of delicious panties. They were soft and silky, and I wanted to touch them. “Five more for each of us,” she said, grinning playfully. “You were guessing right far too often.”

“About once a week isn’t too often,” I protested, still staring at those new panties.

“My game. My rules.”

Next, she pulled out a trio of bras. She handed me one. It was black and decorated with purple and white orchids. “Put that on. It will help.”

I sat up and felt the pull of those breast forms on my skin. They were heavy and awkward. They seemed to move where they wanted and each time they did they tugged uncomfortably on my skin. I brought my hands up to hold them aloft, taking the pressure off my chest. It dawned on me then, cupping my breasts, that I now needed a bra. A bra would help the forms feel more comfortable.

Peyton was watching me from the side of the bed. Smiling, taking in the way I held my breasts, seeing the way I moved and how my face twisted as a pang of discomfort raced along my skin.

I glanced at the tag – A 38D. I put on the bra, fastening the clasp below my artificial breasts, spinning the bra around so that the claps were behind me, before working my arms through the straps. I adjusted my breasts into the cups before pulling my hands away. The bra held the breast forms, taking pressure off my skin, while propping them up as if offering them to the world. Peyton was right – I was stacked.

“Very nice,” Peyton said.  “We’ll have to get you some more bras, but it’ll be much more enjoyable with you there to try them on. Maybe we can have Carla measure you again. Won’t that be fun?” I thought it sounded humiliating and when I told that to Peyton she said, “Then that’s what we’ll do.” That was followed with another one of her adorable giggles.

We spent the rest of the evening getting me ready for work the next day, going over my wardrobe and playing with makeup. Peyton grew more and more aroused and twice before we went to bed, I satisfied her with my fingers and mouth and tongue.

As was the normal now, Peyton stayed the night with me. Sometimes I slept at her place and once we spent the weekend together in a hotel just to put our normal routine on hold. Peyton fell asleep with the speed of a cheetah while I lay there, my eyes closed, contemplating the following morning. I was going to go to work dressed as a woman, head to toe. It would be a first. A big first. Maybe the biggest.

And I was scared.

I felt my pulse in my temples. My mouth was dry. My breasts felt heavy and I was still wearing my new bra because it helped take the weight of my breast forms off my skin. Every physical discomfort paled to the thoughts that were keeping me awake. I would be going to work in a skirt. Sure, it was a well-made skirt, black with thin silver pinstripes. I had a matching woman’s blazer and a white blouse with lace piping at the collar and cuffs. It was a beautiful suit. A beautiful woman’s suit, and I’d be wearing it to work.

My staff was ready. They had all seen my heels and the few people that commented where mostly supportive. Maybe society was changing and a man in a skirt wasn’t that far from mainstream or maybe my staff just wanted to eat, and they were happy enough with their jobs to keep their mouths shut. Did it matter? Did they talk about me behind my back? Maybe. Probably.

Gayle was looking forward to it. I can’t count how many times she had said that she couldn’t wait to see me in a skirt and then followed that up by asking if I wanted to trade jobs with her. “Maybe you can be the pretty secretary fetching coffee for me, Ms. Sweet.” She had laughed at that while all I felt was a tightening in my cock cage. The idea was deliciously demeaning and seemed to somehow fuel my submissive fantasies. Just that thought was exciting. I didn’t admit it to Gayle and I kept it from Peyton. I just knew if I mentioned it to Peyton, she would find a way to make it happen. No, some fantasies are best kept secret.

When the alarm clock woke me, I was surprised to learn I had slept at all.

Peyton stirred, opened her eyes and then leapt from bed. It had dawned on her what was happening and that had pulled her from her slumber with all the zeal of a child racing downstairs to see what Santa brought the night before. She reached for me, touched the breast forms still captured in my lacy, flowery bra and let out a soft little moan of excitement.

That lead to her unlocking me and satisfying both of us. After she said, “I know what panties you’re wearing and in celebration I’m going to wear the exact same pair.” So at least that game was still going, and the rules not violated. Not that it mattered; I enjoyed my reward.

Peyton helped me shower, washing me all over. She took out my pink razor and shaved my face. It was very sensual and erotic. She was all smiles as she ran the razor along my skin. She shaved my armpits and touched up a few stray hairs at my knees. My breasts, supported only by my skin, felt heavy, but I was mostly unaware of that feeling. I was too caught up on what Peyton was doing and the giddiness she revealed. She was having a blast.

Peyton turned off the water and dried us both. She used to towel to blot my skin, “like a woman,” she instructed me. I simply nodded.

Peyton pulled me to the mirror and used the same towel I’d blotted dry with to dry my hair. She gave me a little frown, shook her head, and then smiled. The master bathroom had twin sinks and between the sinks were four little drawers. I had given two of them to Peyton and she raced to open the bottom most drawer. Smiling even larger now, her face glowing with it, Peyton pulled out a pair of tweezers. “This might sting,” she said. With that she proceeded to pluck my eyebrows. It did sting both physically and emotionally. Peyton was sitting on the vanity, plucking my eyebrows and I could see them in my reflection getting thinner and thinner. It was something I would not be able to hide even if I were wearing jeans and a t-shirt. How could I revert to Mason mode with my eyebrows so thin? Peyton kept plucking, thinning them more and more. She shaped them as well. Where once they’d been quite full and maybe a bit bushy, they were now thin and slightly arched. I’d never be able to hide them. Peyton must have sensed my trepidation. “Don’t worry,” she said, still smiling, “we can use a pencil to fill them in. Nobody will know.” She leaned forward and gave me a quick kiss. “Well, I’ll know.”

I looked at myself in the mirror, unable to take my eyes away. With my eyebrows shaped my face looked much more feminine. It was a tad scary knowing that this new, more delicate face was my own. My cheeks were awash with a crimson hue as the thoughts of my upcoming humiliation seemed to brighten not only my cheeks but my neck and forehead as well. The bathroom felt hot, my skin felt even hotter.

Peyton hopped off the vanity and ran from the bathroom. I called after her. She chided me to “not move.” I felt compelled to obey. I wanted to, of course, but it went deeper than that. The bathroom had only one exit that led to the master bedroom. The master bedroom led to a short hallway that opened into my laundry room and the interconnecting walkway between the kitchen and the formal dining room before spilling out into the large family room. The bathroom was a lot further away from the terror that was work. The nightmare that was outside. No, the bathroom felt safe. That was why I wanted to stay put.

Peyton returned with the makeup we had been playing with the night before. She hopped back on the counter and proceeded to add a splash of blue to my eyelids. She blended the eyeshadow with her finger. Smiling and humming a Lady Gaga song we both liked, Peyton pulled out a mascara brush and did my eyelashes. She put lipstick on my face and added a bit of concealer to my neck and cheeks before adding a splash of artificial color about half as bright as my own embarrassment had caused them to glow. She finished by adding some black eyeliner to my eyelids, pulling the black color into a point a tiny bit away from my eyes. My face, already looking effeminate by my plucked eyebrows now screamed something much louder. I looked almost like a woman and while not exactly pretty I wasn’t homely either. I’d rate me a bit above average and being a man, I really couldn’t ask for more than that.

Once again Peyton jumped off the vanity. Lady Gaga disappeared as Peyton started singing an Elton John song. I didn’t know the words, but I recognized the song just the same. Peyton darted into the walk-in closet and returned with a wig. “Your hair is getting longer,” she said, “but it’s not long enough yet.”

It was why we had purchased the wigs. I was growing my hair out; Peyton had forbidden me from getting it cut. “If you get a haircut, Sweetness,” she had said after a panty check that I’d not won, “I’m going to buy each of us a hundred pairs of panties. You’ll never match me then.” If it was a threat it was a damned effective one. I had agreed and why wouldn’t I? It was her show after all.

Peyton put the wig on my head. In the mirror behind Peyton a comely woman wearing a towel wrapped around her fake breasts stared back at me. The makeup Peyton had done was about as good as it could be. I tasted the lipstick, the artificial thickness of it feeling heavy on my lips. I felt the wig on my head and the hair as it rested on my shoulders. My hair was a light brown tinged with auburn. It was long and straight and parted just a little off center. It reminded me a little bit of the way Jennifer Aniston wore it on that old TV show Friends. My hair curled slightly at the end.

“Wow,” Peyton said.

I nodded, staring at my reflection. I dropped the towel. I wasn’t exactly thin, but I wasn’t fat either. My stomach protruded slightly, like a woman just beginning to show that she was pregnant. With my breast forms hanging from my chest I thought I looked like a woman, at least from the waist up. Women didn’t sport what I did down below. Still, it was a damned good illusion.

We crossed into the bedroom where I got dressed as Peyton looked on. After donning my bra, I put on the white blouse with the lace piping. I slipped black stockings up my denuded legs getting a soft erotic chill. I stepped into a black garter belt and attached the straps, enjoying the taut pull every bit as much as I had the first time I wore that particularly feminine piece of lingerie. I stepped into my skirt, trembling both in fear and excitement. I slipped on my blazer and slid my feet into a new pair of heels. They were black but with a three-and-a-half-inch heel that was quite a bit narrower than the first pair of heels I wore to work.

“Oh my God, Mason, you look…”

“What?” I asked, suddenly afraid. Did I look ridiculous? Scary? I wanted to see but I was afraid to look. The bathroom was a single door away. I glanced at the open door, at Peyton who was eyeing me with a huge grin on her face. Her mouth was hanging open and her eyes were wide. It was a good sign or at least I took it as one.

I had to see. I marched into the bathroom and stared at a lovely, professional woman in the mirror. I turned and the woman in the mirror matched my every motion. I raised my hand and my feminine doppelganger did the same. It was uncanny. I looked like an average woman wearing an expensive suit about to leave for her high-powered executive job. I could have been a fancy lawyer or a high-end account executive for a Fortune 500 company and I looked the part. I looked like a woman. It was uncanny and scary and exciting and so many other things that I had to grab the vanity to keep from falling to the ground.

Peyton stood in the doorway, watching me in the mirror. She still wore that playful smile but there was something else on her face. Pride, I think. I could almost see her revealing in what she created, and I was here creation. Never in a billion years would I have the courage to do what I not only wanted to now do but was I was racing towards. I was going to work fully dressed as a woman. Just the thought of it buckled my knees.

Peyton got dressed in her simple green scrubs. I felt a petty sense of amused superiority like I was the pretty girl at school that got a car for her birthday while my best friend only received a cell phone or something much smaller. It was petty, and it made me tingle. Peyton was and always would be prettier but at that moment, standing next to her in my expensive suit, I was the important one. Maybe petty is too small a word.

Peyton was all smiles as we walked to the door. “You can do this,” she said, holding my hand and giving me a kiss. “And I can’t wait to hear all about it.” She handed me my purse and picked up her own. Mine was a simple black clutch while Peyton’s was white with dark brown piping that she hung on her shoulder.

“Thanks,” I said, taking my clutch in my clammy hands. I smiled nervously. It was time and I was ready, but I was terrified too. I’d felt so many emotions since I’d climbed out of bed, both high and low and I knew I’d be feeling even more as the day progressed. Standing at my front door, with Peyton offering her indefatigable support, I knew I’d make it through the day. I wanted to. She wanted me to and as we left my house and locked the door behind me, I could think of nothing else but making sure I earned the wanton look that Peyton was giving me. She was excited and that was because of me. As a man I can’t think of anything more arousing that being given the look that Peyton was giving me. It was a look of wanting, a look of overwhelming need, a predatory look of carnal lust.

“I’ve got to run by my place,” she said. “Our panties don’t match yet, and we haven’t washed the new ones.” She smiled, looking up at me with that same needy gaze, “but they will.”

She kissed me goodbye and left me standing alone at my SUV. I was ready, and I wasn’t, and it didn’t really matter. I was committed. Or maybe I should be. Was what I as doing crazy? Maybe. Was it exciting? Oh, my God, yes! 

I opened the door to my SUV and drove to work. It was time. I was ready.

Or so I thought.