When William becomes Billie, his wife’s femme servant, his world gets turned upside down — and all his dreams come true.

I smiled, enjoying the sound of my heels echoing off the walls as I walked across the terrazzo floor of the post office. I noticed a man weighing a package steal a glance my way as I clattered by. There was a look of disappointment on his face, and I knew that he had been expecting to see a pair of sexy legs balanced on stiletto fuck-me pumps. Instead, he saw a 50-ish man with steel heel plates on his shoes.

Aw, shucks. No fantasy fulfillment for him, but there was plenty going on for me. You see, the heel plates on my shoes and all the other adaptations I’ve made to my wardrobe are at the orders of Mistress Samantha, who also happens to be my wife. The clicking is a constant reminder of my total submission to my mistress. If the man had been really observant, he would have noticed I was wearing women’s loafers, with slightly elevated heels. My trousers hid the silky black thigh-highs covering my legs, and he couldn’t see that I was wearing nylon panties or that my toenails were painted bright red. All of these details are a result of orders that Mistress Samantha has given me.

The articles and letters in Penthouse Variations had always turned me on, and as I grew older my cross-dressing fantasies became more intense. I’d always been afraid to let Samantha know I wanted to try living out my fantasies with her, although I never hid the fact that the erotic subject fascinated me. Then one day the perfect opportunity finally arose.

Shortly after the new year, I was told by my company that they were downsizing. I could either take a severance package or keep my job, which they were relocating across the country. Getting that news was like being punched in the gut. I had been with them for a number of years and had even let them relocate me once before. When I got home that night and told Samantha, she was even angrier at the company than I was.

“Fuck ’em,” she said. “We’re not moving. Make me a drink, and we’ll talk about this. Those bastards!”

Strangely, I found myself sexually excited as I mixed martinis for both of us. Samantha’s take-charge attitude was turning me on. Sitting in a large leather chair, she took the drink without thanking me as she stared out into our peaceful backyard. I could tell she was thinking about the situation. Finally, she spoke.

“Moving is definitely out of the question. I’m not leaving my job behind.” Samantha is a successful real estate agent, and I agreed that she shouldn’t have to give up her thriving business. We discussed our other options.

“How much severance are you getting?” she asked. I explained that I would get two weeks’ pay for every year worked, plus another five weeks for vacation. I was sitting on the ottoman in front of Samantha’s chair, and as she nodded, she put her feet up in my lap. I took off her black leather pumps and massaged her stockinged feet.

Just touching my wife’s nylons made me feel more grounded and safe — and affectionate. Leaning over, I kissed her toes through her stockings, inhaling the sexy aroma of leather lingering from her shoes. I continued to rub her feet and calves as Samantha found my swollen penis with one of her silky feet. The nylon glided over my wool trousers, kneading my erection to fullness.

“Light a fire, draw the drapes and take off your clothes,” she suddenly commanded. In my mind I wanted to reply, “Yes, Mistress,” but instead I followed her directions in silence as she slipped out of her clothes.

She hadn’t adopted that title yet, though I longed to address her as such.

Samantha lay down in front of the fireplace, and I knelt down next to her. My left hand caressed her breasts as my right slid to her moist slit, working her clit. I lay down, our lips touching as our mouths opened. Her tongue pushed mine back into my mouth as she kissed me hard, the flames in the fireplace adding to the heat generated by our bodies. She cupped my balls in her hand, then her fingers glided over my penis. I positioned myself between her legs and guided my swollen cock into her. She sucked hard on my tongue as I slowly moved my dick in and out of her moist pussy. Wrapping her legs around me, she tightened and released them, setting the rhythm. I held back my orgasm as long as I could, but it wasn’t long before I was shooting my load into her, groaning with release. Spent, I slid to the side and put my hand back on Samantha’s slippery pussy to bring her to orgasm, like I often do.

After a few minutes, Samantha moved my hand away and got up, pushing me onto my back and easing her juicy cunt over my face. As she ground her pussy into my face, my tongue found her clit. Samantha had never taken this position before, and it excited me tremendously. I licked, sucked and nibbled with abandon, swallowing her flowing juices, mixed with my own cream. I felt her leg muscles tense as she let out a cry of pleasure then collapsed beside me. Content, we lay quietly together, gently caressing each other for a good, long while.

“That was wonderful,” I said as I got our drinks. Then I decided to take a chance. “I got really turned on by your stockings and how aggressive you were.”

Samantha just smiled and kissed me as I sat back down beside her in front of the fire.

Finally, she spoke. “I’ve got some ideas about our situation,” she said, somewhat mysteriously. “Do you want to hear them?” I nodded, happily. She explained that she wanted me to become her assistant in her real estate business. I would handle all the administrative details at home while she worked with the clients. “So you’d be my boss?” I asked, instantly intrigued.

“Yes,” she replied. “But not just at work.”

A sexy thrill shot through my body that was hard to explain. It was a combination of having a secret found out and a weight I had been carrying lifted. I felt both nervousness and relief as I urged her to explain.

“Now, look. I know you’ve been skirting around cross-dressing for a long time, right? I see what pages of Variations get dog-eared. You know this crossroads in your life could really be a wonderful opportunity for us to work out a lifestyle that makes sense to both of us and is particularly fulfilling for you. Wouldn’t that be nice?”

My head was spinning. “Well, yes,” I answered, grinning.

“You meant to say, ‘Yes, Mistress.’ Right?”

“Yes, Mistress,” I replied, a feeling of excitement washing over me.

“That’s better. From now on, I’d like to be addressed as Mistress Samantha. You know, I can see from those magazines of yours that not all transvestites are dressed up in ruffled maid’s uniforms. We can create our own world of fantasy clothes for you that makes sense for us and keeps you hard and ready to service me. Now wouldn’t you like that?”

“Yes, ma’am.”

“There was a loud crack as the first blow struck, and my ass was on fire.”

“You know, you look so pretty when you talk like that. So you see, I think we can figure out a way for you to live out your cross-dressing fantasies, and at the same time, I can get relief from housework to get more of my business work done. That’s what I’ve been mulling over. Freshen our drinks and get some cheese and crackers, and I’ll explain further.”

“Yes, ma’am,” I responded, still feeling kind of light-headed.

I had gone from family breadwinner to Mistress Samantha’s personal assistant with sexy wardrobe possibilities in only a few short hours.

Mistress Samantha already had detailed plans for me.

“From now on, you will do all the cooking, laundry, marketing and cleaning. Our roles will totally reverse — well, not totally. You will still do the yardwork and repairs as you have in the past,” she said with a smile. “You can start tomorrow as my assistant or, I should say, secretary. One other thing: I also get to decide how you dress. Does that fit with your fantasies?”

“Oh, yes, ma’am, it does,” I replied.

“Yes, we’ll have fun with this!” Mistress exclaimed. “Why don’t we get started by seeing how you look in my panties.”

We went to our bedroom, and I had an erection even before I had the black nylon lace-trimmed panties pulled up past my knees.

“Yes, I was right. This is the real you,” Mistress stated as she felt my erection through the silky fabric, making me even more excited. The snug-fitting panties strained against my cock as it grew larger under her touch. I could see the damp spot where my pre-come had seeped through the delicate material. I was aching to come and, in the spirit of our former lovemaking, told her so. Abruptly, Samantha stopped.

“If we’re going to do this, you must remember the rules,” she admonished me. “I get to call all the shots. This time, however, I’ll let it slide. Just don’t do it again.”

“Yes, Mistress,” I hung my head and waited for her next move. Once again, Samantha stroked my rigid cock through the silky fabric. She teased me for a while, running one fingertip over the dripping head, then eased the panties down, freeing my cock and balls. Reaching for the lotion she keeps on her dressing table, she squeezed some on my cock. I shivered as the cool cream hit my skin, then relaxed as she grasped me firmly, rubbing the lotion over my shaft. With her other hand, she cupped my balls, and as she pumped my slippery prick, all I could think about was the feeling of the tight elastic waistband wrapped around my thighs. The realization that my fantasy of having sex with my wife while wearing her underwear was finally about to come true sent me over the edge. I came harder than I’d ever come before, covering Samantha’s hands and chest with my sticky semen.

After I had caught my breath, Samantha ordered me to clean up the mess that I’d made. I eagerly obeyed, wiping her off with a moist washcloth as she commented, “Well, well, there’s a fine start for us. But now it’s time for you to make us supper. Would you like to do that while wearing my panties?”

“Yes, ma’am. This is all too wonderful,” I replied softly.

“One more thing. Anytime you want to stop being my cross-dressed assistant, just let me know. We can always take a break from this, even temporarily. Otherwise, be prepared to do as I say.”

In the next few days, my life completely changed. Not only did I embark on my new job responsibilities assisting Samantha in every way, but she also gave me a new name. I was to be called Billie when I was serving her, dressed up. It was all very neat and very discreet. At the same time, Samantha took every opportunity to open me up to new vistas of female dressing. Sometimes I even thought that feminine clothes for me were becoming as much her fantasy as mine.

One of the first things she did was have me replace all of my underwear, socks and pajamas with nylon panties, thigh-high stockings and satin nighties. When I went to buy these, the checkout woman said that she wished her husband bought her such pretty things. I could feel my face flush as I muttered something about it being my wife’s birthday. Though deep down, I think she realized they were for me.

Samantha then noticed that my shoes fit loosely when I was wearing the thin stockings, so she took me to a warehouse shoe outlet and bought me several pairs of women’s shoes. Black patent Mary Janes are for my housemaid tasks at home. Brown leather loafers with a decorative metal ornament across the vamp and black leather lace-up oxfords with a slight heel are for street wear, such as when I go grocery shopping. Except for the Mary Janes, all could be mistaken for men’s shoes, but of course I know that they are not and am always very conscious of that. To further heighten my awareness of my position in relation to Mistress Samantha, she had metal heel plates put on my shoes so that their tapping will be a constant reminder to me of my sexual purpose in life. Finally, she presented me with a bottle of bright red nail polish with orders to keep my toenails painted at all times.

“Her legs held my face against her pussy until she came down from her high.”

So each day when I go to the post office to pick up our business mail, I clatter across the floor. Mistress has also found another use for the post office box. Often when I pick up the mail, I find that she has ordered a surprise for us. One time it was a large-size satin bustier. Last week, it was a harness with a butt plug and a cockring, which she required me to wear while I cut the grass. Needless to say, I love how Samantha has taken to dominating me, and our sex couldn’t be better.

The other night she gave me the greatest surprise and thrill so far. After I had cleaned up the kitchen, she came in and found that the floor had some spills dried on it. Further, she said that she had inspected the house and that my cleaning wasn’t meeting her standards. Obviously, I needed to be punished. But before she could even think about that, she said, she needed for me to do something else. She ordered me to go to the pharmacy and buy a couple bottles of hair removal cream. By the time I returned home I was trembling with excitement.

As soon as I opened the door, Mistress ordered, “Go up to the bathroom, strip and take that into the shower and apply it over your entire body, except for your head. I want your entire body silky-smooth.”

“Yes, Mistress,” I replied, my voice quivering with excitement. I spread the cream on and stood in the shower stall with a raging erection, waiting for it to do its work.

“If there’s still some hair left when you rinse it off, then repeat the process or shave it,” Mistress yelled from the bedroom. “There’s a bottle of perfume on my vanity. Use it when you have all the hair off.”  

The hair magically came off my body in clumps. When I stepped from the shower, I was hairless except for a few stray wisps that I removed with shaving cream and a razor. I slid my hands down my legs, marveling at how soft and smooth they were. 

On the counter I found a brand-new pair of pink high-cut nylon thong panties trimmed in white lace that Mistress had left for me. I blow-dried my hair and then sprayed the sweet, stinging cologne all over my body before sliding on the panties. She’d also left me a short apron. With both of these on, my ass felt particularly naked and vulnerable.

“Oh, one more thing, Billie. Freshen the polish on your toenails before you come into the bedroom. I’ll let you know when I’m ready for you.”

“Yes, Mistress,” I replied. My hands shook as I carefully applied the scarlet polish to my toenails. Mistress let me sit in the bathroom for at least 30 minutes while it dried, and I was going crazy with anticipation. When she finally beckoned to me, I was not disappointed.

Our bedroom was illuminated by a dozen candles of all shapes and sizes. Mistress was sitting at her vanity in her satin bathrobe, which had fallen open to reveal her majestic nudity underneath. She still had her heels on, though, and was impatiently tapping her foot on the floor. In her right hand was a black riding crop about two feet long which she held across her body, with the tip resting against her left palm.

“It’s time for your first punishment session. I know you’ve been looking forward to this as much as I have. You do know what you’ve done to displease me, don’t you?”

“I think so, ma’am,’ I replied. “My housekeeping has not been satisfactory.”

“That’s correct. You are a marvelous secretary, but you need to pay more attention to your cleaning. Now come over here so I may examine you.”

I walked over to Mistress with my eyes submissively downcast, marveling at how wonderful she looked. She had evidently trimmed her pussy, a task I had been hoping she would eventually assign to me. She used the crop to poke at my erection, which was swelling in my pink panties, and a chill ran through my body. She tapped the crop against my thigh, demanding I spread my legs so she could continue her inspection. My panties were pulled down so she could examine my hairless cock and balls, then she picked up a black leather collar from the bed and fastened it around my neck.

“You will wear this whenever I command it. I will simply say ‘collar’ and you will go and put it on.”

She took a step back for a final look at me.

“Very good. You’ll remain hairless from now on. Now bend over and put your hands on the bed.”

“Yes, Mistress.” I did what I was told, with my panties still banded around my thighs.

“I think two strokes to each ass cheek will suffice for your offense. Are you ready?”

“Yes, ma’am.”

There was a loud crack as the first blow struck, and my ass was instantly on fire. The rest of the blows were delivered in short order.

“Now, stand up and touch your naughty ass!” Mistress ordered. I could feel the heat rising from my flesh, and I found it exciting that she had marked me. It must have excited her as well, for she then commanded me to lick her pussy.

I eagerly buried my face between her legs and lapped up her musk, turned on as never before. She wrapped her legs around me and drew me into her, her hands gliding over my smooth arms as my hands played with her hard nipples. She made new marks on my ass with her stiletto heels, adding to those left by the riding crop.

While I was licking, she kept taunting me with comments such as, “Oh, Billie, I know you can do better than that.”

I wanted desperately to please her, to give her pleasure for all the pleasure she had given me, so I increased my efforts on her pussy. Running my tongue over her hard clitoris, I heard her gasp as I connected with that sensitive nub. Her body began to shake as she gripped my shoulders tightly, balancing herself on the edge of the bed.

Sensing her impeding orgasm, I slid my tongue down to her tight hole, lapping up the sweet nectar that had been welling there. When she cried out for more, I returned my attention to her clit, furiously flicking my tongue over it until she could hold back no longer. When she came, it was with almost a shriek, and she drove her heels into my thighs. Her legs held my face against her pussy until she came down from her high.

When she released me, I remained on my knees until I was given permission to stand before her in my dainty apron and pre-come soaked panties, the collar still around my neck. She positioned herself against the mound of pillows on the bed and commanded, “Get me a glass of chardonnay, and don’t you dare touch your penis while you’re out of this room.”

When I returned, she had me stand before her for about five minutes as she sipped her wine before finally saying, “Carefully untie your apron. It would amuse me to watch you masturbate in your panties. Would you like that?”

“Oh yes, Mistress. Thank you,” I replied, thinking that I was the luckiest man in the world.

“She teased me for a while, then eased the panties down, freeing my cock.”

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