This was it. My big week. My wife and kids were out of town for a week. I had the house all to myself. Most guys would use the time to drink and watch football. Call me weird, but I had different plans entirely. I took off work early on that Friday to take them to the airport, and by now it was about three o'clock in the afternoon and I was alone. I'm not a big guy. I'm only 5'8" and a slight build. I'd actually been eating really healthy lately and exercising to tone up. My wife thought I looked great. I wasn't really doing it for her, though. I was down to about 135 lbs and toned all over, but not chiseled. I had also been tanning. I really did look pretty good. So why all the effort? I'm not trying to attract women. My wife and I are very happy. I have a couple fetishes. The first one relates to hair. Ever since I can remember I've been attracted to short hair and shaved heads on women. I've always been afraid to tell my wife. I've casually mentioned to her that I thought a shorter style would look good on her, but she says she'll never cut her hair. I also enjoy the look of a bald pussy. She won't do that either. The other major fetish I have is related to clothing. Hair is only part of the package. A great looking woman needs to dress well, too. I love trendy fashion and sexy clothes, and especially high heels. Heels make every outfit. A casual pair of jeans or shorts looks better with heels than a skirt with flats. I can never seem to get my wife to dress how I want her to either.
Which brings me to the purpose of my week alone. I've discovered the joys of cross-dressing. This does not make me homosexual or transsexual. I am very much heterosexual. What I like are the look and feel of women's clothes. All the styles and textures that men can't wear: skirts and dresses, leggings and pantyhose, silk and satin, nylon and spandex, rayon and taffeta, lace and ruffles, and of course, high heels. I've also envied the hairless nature of women. So my first task being alone was to shave everything. I stripped and stood at the bathroom mirror. I took my clippers and ran them all over my entire body. Arms, armpits, chest, butt, legs and pubes. I bought a fresh stock of brand new razors and proceded to lather and shave everything I had just buzzed. After about an hour I was smooth below the neck. I shaved my face again to be rid of the five o'clock shadow. Next I massaged a sweet smelling moisturizing cream all over my entire body. Being smooth felt so good. I wished I had done this years ago and was seriously considering making it permanent.
I put on a thong and a pair of black sheer pantyhose. Oh, that feeling! Women don't know how good they have it. I put on a bra and stuffed it with a pair of fake breasts that I had picked up online. Next I pulled on a tan colored satin pencil skirt and and tight black sweater. I fit nicely into a size 4 skirt and small top. I then carefully applied my makeup. I had never really done it before, but I was pretty pleased with the results. I used just enough foundation to cover my beard shadow and lipstick, eyeliner, mascara and eye shadow to finish up. I had pierced my ears several months earlier, to the initial objections of my wife (she got used to them), and now put on some long dangly earrings. Finally I topped it off with a long, straight, brown wig with eyebrow length bangs (I love bangs), and stepped into my heels. I spent the next hour staring at myself in the mirror and practicing walking in heels. I felt really sexy and I thought I looked pretty sexy, too. I've always been kind of a pretty guy, and now I think I would fool most people.
I sat down on the couch and started to watch a movie. I wasn't quite prepared to venture outside yet. About halfway through the movie I heard something vague, but ignored it. But then I heard the sound of high heels approaching. I froze. Who could this be? I didn't want anyone to know my dark secret. The lights were off, but in the glow of the TV I could be seen.
"Oh my god!" said a voice.
I looked. It was Angela from the office. This is a disaster, I thought. I could see my world crumbling around me. My breath was stuck in my throat. I was mortified. What an hour ago had been so much fun now seemed like the dumbest idea in the world.
"Drake?" she said.
Nothing. She moved toward the wall and turned on the light. I had nothing to hide behind. I was completely exposed.
"W... What are you doing here?" my voice quivered. Angela was a notorious flirt. She had had a known crush on me for some time now. I had occasionally flirted back, but for the most part I'd done my best to avoid difficult situations with her. She was very attractive, with long brown hair to her waist and a great body. She always dressed well and I found it really hard not to think about her some times. Today she was wearing a grey skirt suit that hugged all her curves beautifully.
It was clear that she was taken aback by the drag queen that now stood before her. "I found out that you were alone for the week and I thought I might get a chance for some alone time. And you left you front door unlocked. But I have to admit that this is a bit of a surprise."
"Shit!" I said. "I guess now you know my secret."
"I know more about you than you realize," she said. "I hacked into your internet records at work. It seams you have some unusual tastes."
"And you still like me?" I replied.
"Let me tell you something," she answered. "I'm a very open minded woman. But I also know when I have the upper hand in a situation."
I started to get nervous again. "I'm going to change out of this outfit," I said as I started to walk away.
She stopped me. "No," she said. "I kinda like it. You look really good."
No it was my turn for shock. "My purpose here was to seduce you, to put it bluntly," she stated. "I didn't know if you would cave, but now I feel like I can make a stronger case."
"What are you saying?" I questioned.
"I hate to use the word blackmail," she went on, "but if you were to accomodate my desires, I might be persuaded to keep your little secret."
How did I get myself into this situation? It was obvious that she could see my unease.
"What if I were to sweeten the deal a little?" she asked.
"Come again."
"I know about your hair fetish," she said, "and I don't mind. Actually it kinda turns me on."
"Okay," I said. I could feel a little stirring between my legs.
"This is the deal I propose. I keep your secret and you make love to me. And you can do whatever you want with my hair. The truth is that I have wanted you so badly for so long."
My fetish was getting the best of me. This was too exciting to turn down. Besides, the alternative wasn't so pretty either. My wife would probably leave me anyway if she knew about my cross-dressing.
"Okay," I said at last. "You win."
I led her through the house to the master bedroom and into the bathroom. I pulled up a barstool and motioned for her to sit. After she did, I undid her jacket and removed it leaving a lovely white silk blouse. I took a brush and began to slowly brush her long gorgeous hair. She made occasional moaning noises which turned me on even more. Finally I stopped and faced her.
"This is the first night of a long weekend," I said. "Why not drag this out a bit?"
She stood up and kissed me firmly on the lips. I kissed back. We engaged in the most intense kiss I'd ever experienced, arms caressing each other madly.
"That's not the first time I've kissed a woman," she said. "But definitely the best."
I blushed. I had almost forgotten I was still in drag.
I picked up the brush again and began to play her hair some more. Finally I pulled her hair straight forward until it completely covered her face. I divided a wedge in front from the rest of her hair which I pinned back. It went halfway back to her crown. I grabbed my scissors and slowly, carefully snipped the entire section away at the level of her eyebrows. I spent the next few minutes shaping and tidying it up, until finally I stepped out of the way and revealed to her her new haircut. She had thick, brow-length bangs. The rest of her waist length hair I didn't touch. She looked stunning. She smiled, and our lips locked again for several minutes. We made our way into the bedroom and tore each other's clothes off. I was pleased to see that she, too, had no pubic hair. We rolled around naked for awhile investingating each others bodies. I still had my wig and earrings on. Eventually she took my cock deep in her mouth and gave me the most heavenly blow job I'd ever imagined. I came with full force and she swallowed and licked her lips. I promptly returned the favor with my fingers and tongue deep in her sex. She screamed as she came. I was inside her before I could think about it. We made love until 3 in the morning and slept in til noon.
We showered together and as I was reaching for my boxers, she said, "Uh-uh. Wear what you were going to wear if I wasn't here."
That meant that she actually wanted to me to dress in drag. So I started to apply my makeup as I had the night before. I slipped into a pair of shiny black leggings and a drapy tunic and finished it off with hair, earrings and heels.
She wistled me a cat call. "Let's go out," she said.
"I can't go out like this," I countered.
"Nonsense," she said. "You look great. I bet you'll get hit on by guys all day long."
I conceded and she was right. I didn't stand out, and I actually did have guys checking me out. Not that that mattered. I just didn't want to look like a freak. We had a great day. We spent all day shopping and trying on outfits for each other. She was really hot. We went out for a nice dinner and then back to the house. I told her that I had another hairstyle in mind for her. Her response was much more enthusiastic than I expected. I took her to the bathroom and draped a hairstyling gown that I had bought around her neck. I started again by brushing her hair methodically. She again made those moaning noises that drove me crazy. My tunic hid my erection much better than the skirt I had on the night before. At last I picked up the scissors.
"Are you ready?" I asked.
"Do it," she said.
I picked up her hair in my left hand and severed it at the top of her neck. She squealed a little and then giggled as she flung her freshly shorn bob around. I proceded to even up the lengths. It came to chin level in the front and stopped at her hairline in the back. I cut progressively shorter layers in it and used a pair of thinning shears that I had bought earlier that day to shape the bob. Lastly I took her bangs and cut them to an inch above her eyebrows in a straight line across her forehead. I then used a razor to shave her nape clean. She reached up and touched it after I removed the gown and smiled and giggled. She stood and planted a kiss on my lips and we made love again until late into the night.
The next day we hit another mall and spent some more money on clothes. I was again dressed in women's clothes. We got our nails done and eyebrows waxed. I was having a lot of fun. After another dinner out we returned to the house and she made a B-line for the bathroom and fastened the gown around her own neck. This aroused me even more. I pulled out my scissors and got to work. I started on the top cutting her hair to no more that two and a half inches all over. I tapered it to a half inch on the back and sides and used the clipper to trim around her ears and hairline. I left her with an angled sideburn and parted her hair on the side. She was thrilled with her new cut, and again the lovemaking stretched on and on.
The next morning I had to shave my legs again. I put on patterned tights and a silk dress and presented myself to my lady. She was all smiles. We mostly lounged around and went on a walk. I was waiting for the haircut. So was she. When the time came I draped her and reached for the clippers. There was no guard. I brought the machine to her forehead and pushed back. Again and again I did this. Each time she moaned. She was really enjoying this. I tried to make it last as long as I could, but at last I stopped. I placed a hot moist towel on her scalp and then lathered her with shaving cream. With long even strokes I removed the cream and all traces of underlying hair. Finally I massaged a moisturizer into her skin and took a step back. She was beautiful. More beautiful than I'd seen her yet. I kissed her head and moved my fingers all over it. We made love again. And again. And again.
"I want you to leave with me," she said. "I can get us transferred to San Fransisco. You can make a clean break. But I want you to keep dressing like a woman. You'll fit in just fine there."
"Okay," I said. "If you can pull it off, I'll do it."
The next morning I called in sick with a hangover. She wore my wig to work. I went to a dermatologist to get laser hair removal. Everywhere. Including my face. It was painful and I knew I'd have to come back for multiple treatments, but this was worth it.
She came home and tore off the wig. I picked it up and put it on to complete my feminine look for the day.
"I've gotten us transferred," she said. "We fly out tomorrow and start work on Monday."
I packed only my female clothes and accessories. I had to wear men's clothes to board the plane, but changed en route. Upon arrival to San Fran I petitioned to legally change my name to Darcy. I withdrew only enough money to get going and removed myself from the bank accounts and bills. I had left my wife a note to find when she arrived home. I didn't mention Angela. I only said that I had a crisis of identity and believed that I was meant to be a woman. She could keep the house and have full custody of the kids, and I offered to pay alimony and child support. She refused. She said hated the very thought of me and wanted nothing to remind her of me except the kids. The kids were too young to even remember me, but perhaps that's for the best. She burned my stuff and sold the house. Overall I'd say the divorce went relatively smoothly. Like Angela said, it was a clean break. My parents were dead and I was an only child. So there were no attachments. My wife had a good job and I knew she'd find someone. Later I heard that she had remarried.
Angela had insisted that I grow my hair long. After two years it looked alot like the wig I used to wear. She grew her's as well and it was quite long by then. She and I decided to get married. I had to wear men's clothes one last time and tucked my hair up under a wig. We did it in the courthouse. After it was over I changed in the bathroom and threw the clothes out. For my wedding present she let me shave her head again. It was wonderful, and definitely worth the wait.
For her present I told her that I was thinking about having surgery. I wanted to be able to wear a bikini and go swimming with her. I had been taking female hormones for about six months without her knowledge. I had noticed some subtile changes in my voice and my body shape and was ready to take the plunge. She was happy, but told me that I had to keep my penis. I told her that I never had any intention of getting rid of it. So I booked a surgery vacation. I took four weeks off and travelled alone to undergo my transformation. I had several operations: breast implants, butt implants, and reshaping of my facial bones, knees, and larynx to soften my features. Lastly they removed my scrotum and testicles. That felt really weird at first. My penis was the last relic of my manhood. I was black and blue all over, but over the course of the four weeks my incisions all healed and bruising disappeared. I was ready for the reveal to my Angela.
As I walked through the doors at the airport she didn't recognize me at first and then hugged and kissed me and pulled her body into mine. Her hair had grown to about an inch in my absence. We walked through the threshold at our condo and she led me through the halls to the bathroom. There was a stool sitting in front of the mirror. She motioned me to sit. I was initially puzzled but complied. She then draped the gown over my shoulders and snapped it around my neck. I looked up at her and smiled and she smiled back. I heard the pop of the clippers and melted away to bliss.
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