I handed my new iPhone to Peyton. “When I tell you to, hit play.”
Peyton was sitting in my leather recliner, one leg crossed over the other. She had one shoe dangling freely; she could wiggle her toes and the sneaker would fall to the ground. She glanced at the phone. “What are you up to?”
“You’ll see. Hit play when I tell you.”
I walked through the kitchen, turned left and dashed into my bedroom. I kicked off my shoes, doffed my pants and took off my tie. I had a simple beef roast simmering in the crock pot, but before we ate it was time for some fun. I’d had an idea on how to satisfy Peyton’s request to see my panties and it was time to put that plan into motion.
The yellows ones were first because, of course, they had to be. They were the ones that started it all. Peyton was sitting in my favorite recliner, the one I used to sit in every night after my ex-wife had moved out. The one I’d sit in and ponder exactly how I wound up sitting alone, with my marriage not just falling apart but crumbling. The one that would support my weight but couldn’t exactly support the weight of my thoughts.
“Hit play,” I called from the kitchen, just out of view.
The music started. Bob Segar started to wail about taking old records off the shelf.
I darted into the living room and slid across the floor, miming Tom Cruise from one of his earlier movies, the one where he dated a prostitute. I was wearing a white, button down dress shirt and the same yellow panties Peyton had already seen. The ones that had made her say, “Yellow. Nice.” The one that had started it all. They were soft and lacy, the back a thin, sheer material almost like an overused coffee filter. Peyton made an amused snort, set her wine glass on the coffee table, and then began to applaud. “Shake it, mister. Shake it!”
And I shook it. I waggled my pantied ass towards her, shaking my hips. It wasn’t exactly twerking, I didn’t have the coordination for that, but it was close. Peyton was laughing and hooting while I sashayed from one side of the living room to the other. “Here we have Mason wearing a saucy yellow number,” I said, unbuttoning my shirt before tossing it aside, “straight out of a Lane Bryant catalogue. Notice the wide hips and the full seat. The perfect accent for a warm spring day.”
Peyton snorted. In all the years I’ve been on this earth I had never in my life seen a woman having so much fun. Hell, I didn’t know it was possible for anyone to feel as much joy as she seemed to portray and seeing it made me feel the most masculine I’d ever felt. And I was wearing panties. I found that fascinating.
Peyton was still laughing as I left the living room. Bob Segar quit wailing about that old-time rock and roll. Once out of view I dashed to the bedroom and quickly pulled off the yellow panties that Peyton had first seen and donned a new pair. They were a pale purple, solid in the front with thin strips of lace across my behind. A darker purple band encircled my waist and three thin strands of purple ribbon made a lattice across my upper butt. I slipped the purple panties on and rushed back into the living room.
“Now Mason is wearing a delicate purple number. Notice how the stands of ribbon in the back seems to accentuate our model’s butt crack. The little bow on the front emphasizes just how feminine these panties are.”
Peyton laughed again, leaning forward in the recliner to get a better look. I marched back and forth in front of her. A panty model on an imaginary runway. “Very nice,” she applauded. That was followed up by a loud cheer. Another song started, and Peyton turned it off. My silly introduction no longer needing a running music track.
Smiling, I left the room and returned a moment later in the next pair. They were soft and pink with dozens of little white polka dots. I described them in that same faux announcer voice as I traipsed back and forth in front of Peyton. She was laughing and smiling and hooting and hollering, having more fun that I’d ever imagined anyone ever having.
The pink polka-dotted pair was replaced by a light gray pair with black lace trim. Those were followed by a pair of red panties that had purple flowers tatted into the lace. The pastels came next. The aquamarine followed by the teal, the pink followed another light-colored pair that wasn’t quite orange but was close to it. I paraded myself in front of her in every pair of panties I owned. Solid black with lace trim gave way to another black pair of panties that were decorated with light pink hearts sewn in the lace across the back. Green ones trimmed with a florescent orange waistband came next followed by a pair of light blue boy short panties with a neon green bow sewn into the front.
I kept going, swapping out one pair after the other. More pinks came, one light pink with a white bow on each hip that led to another pink pair with purple orchids printed on the lace. A neon pink pair with purple bows followed two pairs, both black, one with gray trim and the other with a silver lightning bolt stitched onto the front. “Mason is now wearing his Super Heroine panties,” I joked in that same announcer voice, standing in front of Peyton with my hands on my hips, my crotch and its silver lightning bolt thrust forward, and my head turned to the side. It was the classic super hero pose made ridiculous by what I was wearing.
Peyton had tears in her eyes from laughing so hard. Still I kept going. I went through a few more pairs of panties, finally ending on a pair of simple black panties. They were bikini panties with a full back. They were solid black with a light tatting of lace around the waist. A simple black bow decorated the front. “Finally, Mason is modeling the first pair of panties he ever bought.”
“Oh,” she said. “Are those special?”
I paced back and forth, finally ending my panty parade by sitting on the arm of the recliner next to her. “They were the first ones I ever bought myself and I still have them, so I guess they are.”
“Where’d you get them?”
“Walmart. The one by the house has these self-checkout lanes. I was there getting some supplies to change the oil in my car. I’m walking out of the automotive section and I’m drawn to the panty section. I wasn’t there to buy any; I hadn’t planned on it at all. Still, I found myself walking past bras and panties and without really thinking I grab these and put them in the cart. They were in my size; the tag had shown me that. I remember shaking like I was doing something illegal. I moved those plastic jars of oil around to kind of squash the panties. To hide them. I looked around, that same guilty behavior I couldn’t hide if I wanted to. Still, I made it to the check out lines and rang up these panties. I finished with the oil and filter, putting them on top of my panties.
“I was surprised that nobody stopped me as I was leaving the store. I shouldn’t have been, but I just felt so guilty.”
Peyton put her hand on my arm. She moved upward and kissed my cheek.
I smiled. “I made it home and left a trail of clothes from the front door to my bathroom. I put the panties on and stood in front of the mirror, turning from side to side. I spun around and stared at my reflection. They were boring, but they were new. I’d kept a few pairs of Linda’s, so that was about the extent of my collection so having some new ones that were exclusively mine made them, I don’t know, more exciting maybe.”
She made a cooing sort of noise that was half understanding and half amusement. She had this look on her face that I had not seen in a long time. It was one of longing and need tinged with excitement. Her brown eyes were wide and looking up at me, her head tilted, her mouth slightly parted. I leaned into her and she inched towards me. I paused, my mouth nearly meeting hers, and held there, the time dragging on into forever. I felt her hands sitting on my thigh. I felt my mouth curve up into a smile. I felt her fingers digging into my skin.
I moved that last tiny bit.
My mouth met hers. We’d had chaste kisses and little nips on the cheek and nose but that kiss, that first real kiss that was far greater than the good night kiss after our first real date, released an eruption of emotion. It made up for the loss of Linda; it made the last two dates with Peyton a promise of what was to come. Our tongues met, darting and dancing, both playful and needy. Her hands rose higher, sliding across my panties. They moved higher still, along my stomach and then higher still. Her fingers slid along my throat, running through my hair. She pulled me towards her, falling backwards, that one shoe finally falling free.
I fell forward, shifting my own hands under her scrubs. Her back arched, telling me without words, that it was okay to continue. I felt the heat of her skin in my palms. My fingers reached her bra and the hidden swell of her breasts. She kissed me harder, her hands pulling my hair hard enough to sting. She kissed me, and I kissed her back with that same molten ferocity. My hands slipped under her bra. I felt the hardened nubs of her nipples grow even harder. She moaned into my mouth. Her hands sidled lower, sliding along my naked chest. I felt her hips shake as she pushed her scrubs lower, revealing her own panties. I glanced downward. I couldn’t help myself. She was wearing a simple thong. “Blue. Nice.”
She giggled before working her panties off her hips. Her hands rose then, returning to my hair. She pushed me lower, indication her desires and I went where she directed. In all the many years we’ve been together, Peyton had never once been shy about defining her needs and that first time was no different. She pushed my head lower, past her chin, over her breast. She pushed me lower still, her legs flailing to work her scrubs and panties free. One leg fell to the ground to land next to her shoe. I went where she led, my kisses following where her determined hands commanded my head to go. My tongue trailed where she directed. She gave a little gasp, her fingers digging into my scalp, when I reached her destination.
Later, both of us sated, and our breathing finally back to normal, Peyton sat up and said, “Now, you said something about heels?”
I laughed. I looked into her eyes, at her smudged make-up and disheveled hair. I looked at the faint smile toying with the corners of her mouth. There was a playfulness on her face and something more. Something primal. Had the thought of my heels led to what we’d just done or was that just a continuation of the fashion parade I’d started an hour earlier. And what did it matter. I was smitten, as was Peyton, and we both knew it.
“I wanna see.”
I stood up, fishing myself back into my small, black panties. That first pair I’d ever bought on my own. Earlier pairs were stolen from my mother and from my best friends’ sister when I’d discovered them in a dirty clothes hamper. They’d been forbidden so they’d been exciting but not as exciting as the first pair I’d bought on my own. I made my way into the kitchen, grabbed a glass of water for both Peyton and I, before returning to her side. I gave her a glass. “Be right back.”
“Yeah!” She took a long pull of water. “Thanks.”
I smiled and left the room.
I owned two pairs of heels. One black and one red. Like most of the things I owned I bought them online. Lane Bryant, Victoria’s Secret, Fredricks of Hollywood. Panties were easy. Once I knew my size I could order with ease. My heels were different. I’d never bought them in person and a man’s shoe is sized different than a woman’s. Online research told me to order them about two sizes bigger and that was a good rule-of-thumb. Both pairs I owned with a size twelve; my own shoes a ten.
I had owned about six pairs of heels in my life. The first two didn’t fit. Online ordering was a crapshoot at best, but they did help me focus in on a size that does work. The next two did fit but of course guilt and denial and anger and too many other emotions to catalogue caused me to throw them away no matter how much I liked them. I’d been younger and maybe that was partly to blame for purging my desires. Linda didn’t help. The first time she had found my heels she’d been livid. “Seriously, Mason!” I heard her shout from the garage. “Are you kidding me?”
I recognized the tone in her voice. The anger, rage, hatred and disgust rolled into one vitriolic screech. I went to see what the commotion was, but I knew before reaching her side. In the beginning of our end only one thing brought that acerbic tone. At the end I heard that same tone in every spoken sentence. “What?”
“Heels. What are you? Some sort of sissy?” She followed that with a burst of disgust. The first heel hit my chest, the second landed just an inch shy of my feet. She had thrown them at me and that fight led me to throw them away. Once Linda left I’d ordered the two pair of heels I still had. The black ones were made of a shiny patent leather with a small two-inch block heel. They were a little plain, but they were comfortable and steady. The red ones were sluttier by far with three thin straps that snaked over my foot to attack to three golden buckles on the side. The red ones had a four-inch heel. I used to wear them a lot. The day they had arrived I’d almost broken my ankle when my foot slid into the groove of my kitchen tiles. I’ve had plenty of practice since. I get an elicit thrill whenever I wear them. More so than the panties. My panties calm me; my heels excite me.
I put the red ones on first. They were the sluttiest ones. They’d likely impress Peyton the most and I fond I wanted to impress her. I wanted to make her happy. I wanted to give her joy I’d seen during the panty parade. Somehow, seeing how happy she’d been had put a smile on my face bigger than I could recall ever wearing. Her happiness somehow magnified my own. Had that ever happened with Linda? Maybe at the beginning but I was younger then and the past has a way of being overwritten by the present. Maybe I’d felt happiness making Linda happy. Maybe. But I know for sure that it had been that way with Peyton and I wanted to do it again. And again. And again. Was I already planning on a future? As I strapped the heels to my feet it felt that I was.
I came into the living room. Peyton was sitting naked on the couch now, craning her neck towards the clip-clopping sounds of my heels. I walked with ease into the living room, my eyes glued to hers. I was looking for a smile and I wasn’t disappointed. It felt amazing sharing my fetishes with someone who wanted to experience them. With someone who wasn’t revolted by them. Maybe that was why I wanted to make Peyton happy. I’m sure it was more than that. Acceptance trumping fear and loneliness was part of it but there was more.
Peyton applauded, leaning forward. “Oh my God, Sweetness,” she said, “I can’t believe you can walk in those things. I love them.”
And her smile grew bigger and that supportive affirmation caused my own face to brighten in a smile. It felt good to be applauded and accepted and that fueled a confidence that I’d been lacking. With Linda I had had to hide a part of who I was. With Peyton I could truly be me. Maybe that was what made me want to please her most of all.
I strutted in front of her with an exaggerated sway to my hips. Another stroll down an imagined runway.
Peyton stopped me as I stooled by and pulled me on top of her again. Her hands went to places that for far too long only my hands had been. She guided me where she wanted me to go. We kissed and caressed. Peyton giggled, “just like a porn star keeping her heels on.” Her giggling escalated to full blown laughter but that didn’t stop either of us from stopping what she had started.
Winded and sated, I sat next to her on the couch. She was naked; I was in my heels. “I love them,” she repeated. “Now, go show me the other pair.”
I wasn’t sure if she meant it as an order. Was she in control of this night, or was I? I had planned the fashion show but since then she had been directing the evening. I found that I wanted her to be. I stood up and she playfully swatted my behind.
I made my way to the bedroom, my heels tapping out a rhythm on the tile floor. I’ve always liked that sound. In the bedroom I swapped the red heels for the lower, simpler black ones. They fit well, even better than the red ones. I returned to Peyton’s side. The smile on her face grew impossibly huge as she saw them. “Oh, they’re perfect.”
She was thinking about something. I could almost see the gears turning. “You like?”
She nodded, her eyes glued to my feet. My eyes were glued on hers. “You have got to wear them to work.”
“Uh, no.” Yet why did the idea excite me? Terrify me, but excite me, too.
“You have to. They’re perfect,” she repeated. “They’re definitely women’s shoes but the heel isn’t that big, and I bet you can get away with it.”
I shook my head. “I don’t think it’s a good…”
She stopped me almost as soon as I started. “Right. I do the thinking, remember,” she giggled. “Come on, Mason, it’ll be great. I bet,” she paused, “yes, let’s make it a bet.” She liked her wagers. I’d already paid off the massage. What would I have to pay this time?
Her eyes were wide and bright and full of mischief. I should have said no but I didn’t want to. I wanted to wear them to work. For me or because Peyton wanted me to - I couldn’t say. “What’s the bet?” I must admit I’ve thought of doing it before. Almost did once or twice but I’ve always chickened out. Maybe I was the sissy Linda thought I was.
She considered my question. “For every day you wear them to work and don’t get caught, I get to decide what you wear to work the next day. Oh, how long until you’re wearing a blouse.” She giggled at the thought. “Or a skirt.”
“I don’t own any blouses,” I said. I ignored the skirt comment. That thought was far too frightening. And exciting.
Just the thought of it gave me chills. “And when I’m caught.” And why wasn’t I trying to dissuade her?
“We’ll go panty shopping and buy enough pairs for the both of us. We can wear matching panties every single day.”
“We should do that anyway.”
I should have said no. I wanted to say no. But the smile on her face and the mischievous glean in her eyes convinced me otherwise. “Oh, hell. Why not. It’s a bet.”
She was on top of me a second later. I was far to tired to respond but even when the down below wasn’t working there were other parts that were. Hands and fingers, lips and tongue. Afterwards, lying on the couch with Peyton lying on top of me, her head resting against my shoulder she whispered, “I’m glad I met you.”
I kissed the top of her head in response.
“Can I use your toothbrush?”
With that simple question I knew that Peyton was going to spend the night. I kissed the top of her head again.
She pushed off me. “Come on. Let’s go to bed.”
I went to bed with Peyton lying naked next to me. It didn’t take her long to fall asleep. I was too wound up worrying about our bet and somehow looking forward to the challenge. Work had become something of an obstacle lately. It was challenging, and I was very well off, but it seemed I was paying for my success by not really living my life. I typically rose early, went to work, and left long after everyone else. I let work consume me during my divorce, distracting me from that failure, and somehow, I hadn’t tried to let work go after Linda was no more. It would be a challenge getting through the day in my simple two-inch heels, but it would be a fun challenge. Maybe it would make work seem a little less intrusive. And I was the boss, would anyone call me out on what I was wearing anyway?
I thought of that movie with Tim Robbins and Morgan Freeman. The Shawshank Redemption. Tim Robbins wore the wardens’ shoes back to his cell after cooking the books late one night. “I mean, seriously,” Red, the character played by Morgan Freeman, narrated, “how often do you really look at another man’s shoes?”
That was the final thought I took to bed that night.