Housesitting for the Boss

by Gloria Marshall

 

When my boss Barbara asked me if I could housesit for her the upcoming week I couldn't believe my good luck. I agreed, trying to act nonchalant, but inside I was doing cartwheels. For I am a closet transvestite, and my boss has an especially luscious wardrobe…and I was guessing we were the same dress size. I would soon find out!

The week dragged by. I was reminded of the last few days before Christmas when I was a boy. But as I counted down the days I was busily preparing for my week of bliss. I bought myself a set of new lingerie, made sure my favorite wig was clean and styled, and, the last day, spent the evening at home carefully giving my entire body a fresh shave. When Saturday arrived I packed my bag and drove to her house, my heart racing.

Barbara met me at the door of her nicely appointed home and gave me the tour, showing me the fuse box, the gas cutoff switch, the main water valve, and the like. Finally she led me upstairs to show me the guest room where I would be staying. It was conveniently located next to her bedroom, I noted.

Finally it was time for her to go catch her plane. "Thank you so much for doing this," she said. "I hope you will enjoy your stay." She had no idea.

Her car was barely out of the driveway before I raced up the stairs, then found myself standing in her bedroom doorway, reverently taking in the surroundings.

Barbara is a very proper woman with precise habits, so I expected a conservatively furnished bedroom. Instead, I found myself in a den of ultra-femininity. She actually had a canopy bed, done up with ivory satin bedding,. The matching curtains were trimmed in lace, and the carpet looked soft enough to sleep on. There was a large vanity in the corner, a full-length antique standing mirror, and matching chest-of-drawers, lingerie chest, and jewelry armoire.

Heart racing, I stepped over to the walk-in closet and opened the door. The contents literally took my breath away. I had seen many of the outfits hanging there—the skirt suits, the conservative but fashionable dresses—but I was delighted to also find an extensive selection of cocktail gowns and furs. A soft moan escaped my lips. I hurried to the guest room and got out my things.

Wanting to prolong the anticipation, I decided to take a shower, then ran myself a bubble bath. Lying in the warm scented tub, my mind was filled with images from that forbidden room. A shudder ran up my back again and again. Finally I could stand it no longer, so got out, drained the tub, and put on my dressing gown and slippers. I wrapped a towel around my hair turban-style, retrieved my bag from the guest room, and padded back into her room.

I spent a long delicious moment considering the gowns in the closet before finally choosing one and taking it down. I laid it on the bed, then took out a fur cape and laid it next to it. Next I explored her armoire, carefully selecting jewelry to go with the outfit.

Taking off my robe, I took out my newly purchased lingerie. First I dressed in a tight gaff, to protect my new undies, then sat on the edge of the bed. As always, sliding sheer stockings up my freshly shaved legs made me shiver with delight. I attached them to my new black satin-and-lace garter belt, then pulled on the matching panties. Next was my bra and silicon breastforms, and finally my favorite item, a long black silk satin slip. Oh! The way it slithered down my slim, feminized body!

Finally I slipped on my black patent high-heeled ankle-strap sandals and stood in front of the mirror. I looked a bit silly—with my buzz cut and no makeup—but that would soon change. I sashayed in front of the mirror, loving the way my slip felt against my silky legs.

Then I happened to look at her nightstand, and my heart leaped into my throat. For lying there was Barbara's dressy bracelet watch. Certain types of ladies' bracelet watches are an especial fetish of mine, and I had lusted after Barbara's from the moment I saw it, at an office party nearly a year ago. I walked across the room and, as if in a dream, picked it up. I returned to the mirror, and watched my reflection as I slipped the heavy brushed gold item over my frail, trembling wrist. I clasped it shut and lowered my hand, and as it slipped slightly down my wrist I moaned aloud.

"What on earth are you doing?" Barbara said from the doorway.

I whirled around, almost stumbling in my 4-inch heels. She was standing with her hands on her hips, looking none too pleased. I could feel myself blushing hotly as she surveyed the scene, taking in both my appearance and the careful arrangement of her formalwear on the bed. It was a little difficult to explain.

"I—ah—I was just…" I began, but really, what could I say?

"My flight was cancelled," she said, visibly trying to control her temper. "And I realized I'd forgotten my dress watch, so I came back here to get it. I see you found it for me." She stared at my wrist. "Take that off at once."

I fumbled with the clasp and took it off. She took off her "office" watch, then held out her hand, palm down, and raised her eyebrows. I nervously tottered to her and clasped the watch around her wrist.

"And my lingerie—" she began, but then she took a closer look and, to my surprise, laughed. "Oh!" she said, "I see! You brought your own…"

She shook her head, laughing even more. "You own your own lingerie…why, what a little sissy you are." I hung my head, mortified.

Finally she looked at the bed again and got over her amusement. "You're like a naughty little boy, sneaking into Mommy's closet," she said. "Well. I know how to deal with that."

With that she grabbed me by the arm and half-dragged me to her vanity. She sat on the bench and threw me over her knee, then picked up a silver-plated hairbrush and without another word began to spank me. She spanked me with gusto, and after a few swats I was reduced to whimpers and small cries of pain. But it didn't slow her down…if anything it made her intensify her efforts.

After several minutes she got up, causing me to stumble backward. I almost fell, but I caught myself. She raised her eyebrows. "I see you are accustomed to wearing heels," she said. "That's not surprising, I suppose. You've probably been wearing them for years."

She seemed to be over her initial anger, and now looked at me thoughtfully. "The next flight isn't for several hours," she said. "And I do need something to amuse myself. I have to admit, I'm rather curious to see what you'd look like…"

She looked back at the vanity. "Oh, of course. A priss like you would have his own makeup kit. That's just too precious. And a wig! I hadn't even noticed that! Oh my word."

She took my hand then, and had me sit at the vanity. She sat beside me. "Well," she said, "let's just see."

She opened my makeup case and surveyed the contents, then took out my foundation. As I watched in growing wonder, she began to do my makeup.

It was a very odd sensation. On the one hand, I was wearing satin lingerie and having my makeup done by a beautiful woman, so a part of me was pleased and excited. On the other hand, this was my boss, who had just given me a rousing spanking—it still hurt!—and I was terrified at what she might do next.

Barbara took her time. Her own makeup is always flawless, so she obviously knew what she was doing. She was certainly much better at it than I was. First she plucked a few stray eyebrow hairs as I nervously watched. I hope she doesn't pluck too many! I thought, but she kept right on, plucking "just one more" until they looked, I thought, decidedly feminine. Oh dear, what would the girls at work think?

As she proceeded with foundation, blush, and eyeshadow, Barbara kept making little comments that made me blush: "My, I can't see any facial hair at all!" and "You know, you have lovely eyelashes, just like a girl," and "Oh, you're going to be so pretty," and "I'll bet you have lots of boyfriends, don't you?"

The last comment finally made me speak. "Oh, I'm not gay," I said.

"No, of course not," she said, her voice thick with sarcasm. "Why would I think a thing like that? Oh wait, I know, it's because you're such an obvious fairy." That caused me to blush even more.

"Or maybe it's because you have these," she said, taking out my false eyelashes. She lined one with a thin bead of glue and settled it in place. "I mean, my goodness, these are something a drag queen would wear." She was right, of course…the eyelashes I had brought were rather dramatic. She applied the second eyelash and said, "That is what you are, isn't it? A little queen?"

"No," I said, "I—I like girls…" but it came out as more of a whimper.

"Mm-hmm, yes, of course you do, dear," she said, picking up a lipliner. "Hold still, now." She carefully lined my lips, then picked up a fullsize lipstick. She cradled my head with one hand as she gave me a lavish lipsticking.

"Now, this should make a big difference," Barbara said with relish, taking my long red wig off its stand. She stretched it over my head, and as the familiar feel of the long wavy locks cascaded onto my bare shoulders I couldn't help myself. "Mmm," I sighed. Barbara noticed, of course. "Why, I think you enjoyed that," she said with amusement. She looked at me in the mirror then, and raised an eyebrow. "Oh yes. You're even prettier than I thought you'd be. Maybe we should take you into work like this? Hmm?"

I gave her a panicked look, which made her grin. "Oh, would that embarrass you? Yes? Would you be afraid the women at work would think you were some sort of pansy? But that's exactly what you are, isn't it?"

She stood up then and strode to the bed. "Come on, princess, let's get you dressed. You obviously spent some time picking out an outfit."

I was still gazing at my reflection—she had done a wonderful job—but then recalled the outfit on the bed. I really did want to wear it. I got up and minced over to her.

She picked up the gown and held it up for me to step into. "Careful with those heels, missy," she said sternly. "If you rip my gown I'll be very unhappy."

I stepped into the gown very, very carefully. The long black satin dress felt incredible as she pulled it up and had me snake my arms into the cap sleeves. As she zipped me up I saw that, indeed, we were very nearly the same size.

"You need gloves with this outfit, of course," Barbara said, going to a drawer. She took out long black satin gloves and handed them to me. "Put these on," she said.

I did so, then held my breath as she picked up the rhinestone bracelet I had selected. "This jewelry belonged to my mother," Barbara said. "You have rather old-fashioned taste…but then drag queens like vintage glamour, don't they?"

"But I'm not—" I squeaked, but my voice caught as she laid the heavy cuff bracelet over my wrist and closed the double clasp closure. It felt heavenly. She followed with the oversized rhinestone clip-on earrings, then gave me a smile as she picked up the necklace.

"This really is made for a queen," she said. I didn't argue this time, but simply held back my hair and arched my neck slightly. She paused, and gave me a level look. "Do you want to wear this?" she asked.

"Y-yes, I do," I whispered.

"Then ask for it," she said.

I gulped. "Please…oh, please put the necklace on me," I said earnestly.

"My, I didn't say you had to beg!" she exclaimed, amused. "You're such a little priss," she continued, draping the necklace around my throat. "I've always known you were…well, less than manly…we've talked about it at work, you know. About how girlish you are."

Was that true? I blushed hotly as she fastened the necklace in place around my neck. As the multiple rows of rhinestones settled around my throat and bare chest I thought I might faint.

"Look in the mirror now," she said. I did as I was told, and my eyes widened at the sight. She stepped behind me and draped the full mink cape around my shoulders, and then my knees turned to jelly and I almost stumbled. She grabbed my arm and helped me stand. She was laughing again.

"Why dear, I think you almost swooned," she said teasingly. "Now just stand there, and look at yourself," she said, stepping back, "and tell me you're not a teensy bit gay."

I stared at my reflection. I had never looked so feminine. I knew it wasn't true—I really did like girls—but maybe…

Barbara glanced at her watch. "Hmm. Yes, we have time," she said. "I have a surprise for you. I'd ask you not to tell anyone about this, but I don't think I have to, do I?"

She walked across to her chest-of-drawers and pulled open the bottom drawer. I was still gazing appreciatively at my new look, but glanced at her and did a double-take. For she was taking out a realistic dildo, attached to what looked like a harness—

She attached the strap-on around her waist and smiled sweetly. "Now," she said, "to show your appreciation for your little dressing, I want you to do something for me. Will you?" I gulped and nodded tentatively.

"Get on your knees," she said softly. I awkwardly complied, then found her in front of me, the large rubbery penis in my face. "Pretend I'm one of your boyfriends," she said, "and give me a nice blowjob."

"I—I'm not—" I said, but to my surprise found myself enveloping the dildo with my creamy red lips.

"Yes, that's nice, dear," Barbara murmured, stroking my hair. "That's a good little priss…hmm, yes, you like that, don't you?"

And I did. I was amazed at how much I liked it. And I—I seemed to be good at it.

"That's right…get it nice and moist…we'll use more lube, of course, but this is a good start…" Barbara said.

After a few moments I found myself being lifted and settled down on the bed, then felt Barbara pull up my gown and slip, and slide a pillow under my ass. She yanked down my panties, and I saw that she had a bottle of lubricant in her hand. She was dribbling it all over the tip of the dildo.

"Oh!" I said, but then she was lying on top of me, sliding the dildo home.

"Don't worry, princess," she said, "I won't go in too far."

My eyes opened wide as I felt her enter me, but true to her word she only pushed it in an inch or two. She fucked me gently, in and out, as the room went in and out of focus.

"Um," I said weakly. And then, finally, I really did swoon.

---

I awoke on the bed, still clothed in Barbara's finery. She was standing over me looking concerned, but smiled as I came to.

"There you are," she said. "My, you enjoyed that, didn't you?"

I had to admit that I did.

"So did my ex," she said with a sigh. "I have missed that…and I have to say, it was even more delicious doing it to someone all dolled up like you are. Quite exhilarating, really."

"Now, I have to leave to catch the next flight," she said. "But when I get back from vacation we'll begin proper strap-on training. After a few weeks you'll be taking all of it—in fact, I'm certain you'll be begging me for all of it. You will come here every Sunday afternoon, we'll dress you up, and I'll have my way with you. Understood?"

"Yes, Ma'am," I said, still shaken.

"Very good," she said. "Now, for this week, all I ask is that you don't soil anything, and put everything back where you found it. Oh, and one other thing."

She handed me a small bulbous rubber item. "This is a butt plug. You will wear it whenever you wear any of my things—with lubricant, of course. Wear something stretchy over it, to hold it in place. I want you to promise that you will do that."

"I promise," I said. What else could I do?

"Good girl," she said. She leaned down, gave me a sloppy kiss, and with that she left the room.

---

I am still all dressed up as I sit at Barbara's computer, as I wanted to write all this down while it was fresh in my mind. My week of housesitting has only just begun, and has already been the experience of a lifetime. And I'm sure Barbara has more surprises in store when she returns.

I'm a bit nervous…and I can't wait!

 

fin

  

  

  

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