Last winter I moved back in with my parents after a bitter divorce and losing my job. My step-father and sister were not all that pleased with the situation but I had little choice and little money. For the first few weeks I regularly went out job hunting but as the results were a constant stream of noes and the weather grew inclement I began to stay home. Wandering around the place where I had grown up brought back floods of memories, behaviors and feelings. Recollections of the fantasies that I had designed resurfaced and day dreams wandered daintily along suppressed ways. The finished basement where I was living also stored all old the family belongings. One day, having received to rejections on early job interviews, I began to browse through the boxes in the basement. The pain of having been turned down brought back the memories of the times I had been rejected in high school. Back then my solace was to change reality and to become someone whom everyone desired to be around. Shaking with excitement I stripped down and began to decide what I was going to wear. The lime green French cut panties went on first and within moments I was fully excited. I began to ooze and knew that unless I addressed this quickly there would be a mess. With rapid strokes I climaxed and then wiped myself clean, every so often squeezing out a lingering droplet until I was flaccid again. This time I slipped myself between my legs and snuggled into the panties. White opaque pantyhose rolled down and onto my slender legs. The tight material wrapping around my calves and thighs, further hiding and securing me. A white bra with lace scallops along the tops of the cups gathered in my meager chest but gave me no cleavage. Two rolled up panties fitted into the cups gave the illusion of a bust line. This was enhanced when I pulled on a clingy black jersey top. The cool fabric molded itself around my bust and waist. The sleeves did little to hide my thin arms though the open neckline gave a hint of cleavage. Next I shook out the black sateen hot pants before drawing them over my legs and around my hips. Compact and smooth the zipper hid any lingering trace of who I was and showed instead who I dreamed of being. Finally I sat on the edge of the bed and unzipped the side of the boots. The vinyl crinkled as I pointed my toe and arched my foot inside. Delightfully tight the boot painted itself over my foot. The long zipper pulled the vinyl to my leg and quickly I stepped into the other boot. As I stood and swayed for an instant over come by the sensation I felt the exquisite tension inside my hot pants. Looking down at my long booted legs I wanted to see how good I looked but the only full length mirror was in the upstairs bathroom. A quick look at the alarm clock told me that I had plenty of time before anyone came home from work. So I strutted upstairs and posed for myself in the mirror. From the neck down the illusion was passable but as I looked at my face I felt let down. So I went into my sister’s bedroom and found a chintzy blue-black page boy wig. The cap was so cheap that it took forever to get the wig to stay in place. The face in the small mirror as closer to fitting the clothes on my body. Then I began to dabble with her make-up. Blush, mascara, eye shadow and liner and lip gloss. In expert my face looked uneven but that did not stop me from going back into the bathroom.
Again I posed and smiled and felt myself ready to burst through the sateen hot pants. The last time I’d done this I had fantasized that Mike who lived down the block would find me dressed like this and that we would neck and he would treat me like a real girl. I gave one last look at myself and started down the stairs to relieve myself. At the bottom of the steps as I turned to go into the basement the front door opened. Cold air swept in with my step-father. For a long instant he simply stood there as if trying to recognize who was standing in the hallway. With no place to hide I merely stood there and waited for the reprimand. Slowly and silently he closed the door. "Don’t move," he said softly and shuffled into the living room. His anger trailed him. A moment later I heard a muffled voice and then the phone being replaced. Shaking with fear and anxiety I remained in place for long minutes. Then the doorbell rang. My fear escalated and my heart was about to rip through my blouse and I felt sweat trickle down my back to the top of my pantyhose. What was my step-father doing? I wondered as he stepped into the hallway and pulled open the door.
Marie, our next door neighbor, entered. She looked from my step-father to me a small smile growing with every second. "I came home so that we could be together and this is in the hall," my step-father spoke quietly as he closed the front door. In shock I was still standing where my step-father had found me. "You’ve got to admit he’s got a cute figure." Marie took a few steps forward.
"I’d kill for legs like that." She stopped a few feet away. "Turn around honey."
In mute response I swiveled on the balls of my feet. "Look at those cheeks Tom.
Round and firm." Suddenly I felt a hand caressing the curve of my right buttock. A thrill shuddered me. Hot breathe blew over the back of my neck. My eyes shut in ecstasy. The hand sweetly kneaded my flesh drawing ever closer to the center. Another hand was on my waist, along the belt of my hot pants, beginning to dive lower and lower. Slowly my flesh began to melt. I twisted my neck to meet the source of that now panting breath. Glossed lips found damp hungry lips. Tongues entwined. Fingers began to push up the center of my rear. Hand circled my zipper. Beneath that hand I felt a tortured need for release. Then the hands moved and rested on my shoulders. Turning me around and forcing me down to my knees. The white vinyl boots creaked as I knelt. Opening my eyes, I looked up. Aflame with lust and desire my step-father began to unbuckle his pants. The moments of pleasure turned to fear and loathing. What was I doing? What were we doing? The sound of the zipper crashed through the hall. From under his white boxer shorts my step-father pulled out his pulsating member. I tried to back away. Hands on my shoulders prevented me from moving. "Relax honey." Marie whispered from behind me. "Just think of it as a big lollipop." My head still tried to retreat but my step-father’s hand grabbed me and brought me head to head. Salty ooze touched my lips. Heat radiated from the pointed flesh. Marie pinched my arm and my mouth opened. My step-father pushed his in and began to rock back and forth. Gagging I fought to find my breath. Panic flooded me until my nostrils flared with breathe. As I started to breath I was able to control my gagging. By now I could sense that my step-father was ready to explode. With one last long thrust my step-father plunged into the back of my throat. The explosion fairly gagged me again . This time I was forced to swallow.
As quickly as it had begun the act was over. "You’re a quick learner, honey." Marie was lifting me off the floor. My step-father turned away as he pulled himself together. "You’ll do fine at tonight’s party." I looked at her in the eye for the first time, she was smiling broadly now. "What party? What are you talking about?"
My step-father walked back into the living room. "Tom, your Dad thought since you like dressing as a girl he’d have a little coming out party for you." She placed an arm around me and began to walk me to front door as she talked. "I’ve got this sweet little red leather dress that you’d look hot in. Not that you don’t look good now, though you need to work on your make-up. But I can do that for you tonight." As she went on she’d opened the front door and directed me outside.
Panic erupted. I couldn’t go out like this, someone would recognize me. Someone would know that I was a man! Yet Marie rattled on about foundation and winter colors as we walked over to her house. The cold air slipped over and passed my booted legs and sent a chill through my jersey blouse. Boot heels sounded on the sidewalk and then we were inside where I felt a sense of calm. That calm lasted only for few minutes when I heard Marie mention who was going to be at this party. Mike!
Part Two
The first thing Marie had me do was strip down. My shamed resistance was laughed away as Marie took me by the hand into her bedroom. "Honey, you’ve got to relax, enjoy yourself." She pulled up my hand and turning the palm upward she softly kissed my hand, her tongue lightly running the length of my middle finger. With a hungry look in eyes she dropped my hand and took off her top, her firm breasts erect and taunt. She smiled and slid a hand into her waistband, "You want to see more you’ll have to match me piece for piece." Quickly I drew the jersey blouse over my head, the wig coming loose and falling to the floor with the blouse. Marie smiled and wiggled out of her jeans, and I tugged away at the sateen hot pants. She kicked off her loafers and I sat on the bed to tug away at the vinyl boots. As I struggled Marie stepped over one leg and pulled away the boot and then she straddled my other leg and pulled off the other one. But instead of moving away she back her full rear into my face. Clad in royal blue silk panties her cheeks poked into my nose. Her scent was intoxicating, rapturous me as my hands held her wide hips. She switched her rear a few times as my tongue flashed out. Then she in one quick movement she stripped off her panties and turned to face me her knees near my ears.
When I moved to remove my panties, she leaned forward, her hands on my shoulders forcing me down onto the bed. Oozing she lowered herself over my face and I breathed in the musky aroma. Then her soft, quivering lips were on mine and like a drowning man I lapped away at her. Time seemed to stop as my tongue moved and circled and darted around and around and around. From far away I could hear gentle moans and then Marie was grinding her hips into my face as I desperately tried to match her tempo. With a last powerful thrust Marie nestled herself onto my face. The dark black hair tickling in the inside of my nose. For a long while we remained that way until Marie finally rolled away. "Honey, you have one mighty tongue. Where did you learn to do that?" I blushed as recalled the first time I’d done something similar. "From my wife," I replied softly. Marie’s hand brushed at my face. "Is that where you learned to dress up too?"
My face went even redder. "No," my voice seemed to be stuck in my throat. "I use to do that when I was just a teenager."
"Well, Honey." Marie paused for a minute. "I can’t keep calling you that, do you have a name for yourself?" She sat up on the bed and I followed suit. "Kerry," I said in as feminine a way as I could and Marie smiled. "I always liked the way keri-lotion felt, soft, smooth, sensual."
"That’s something we can make you into." She stood up and pointed to my bra and pantyhose. "Get rid of those and join me in the bathroom. We’ve got some work to do, Kerry." She left the room and I was alone for the first time in what seemed like a lifetime but was really only a little over a hour. There were a thousand different feelings racing through me as I tried to adjust to the changes that were rapidly occurring. Most of all I was amazed at how natural, though a little scary, this experience felt to me. As I began to undo my bra and then strip down my pantyhose, the same way I had seen my wife undress, I began to feel more feminine. Standing up I looked down at my body and frowned at the thin roll of flesh around my navel. If I wanted to look really good I would have to begin to exercise much more I told myself as I went into Marie’s bathroom. Hot steam wafted from the shower stall and Marie’s bare arm waved me into the streaming jet of water. She lathered my body and toyfully pulled at my withered member, cupping her hand around my plum-sized testicles. Marie said nothing as the sweat and dirty were washed away. Then she stepped out of the shower and pulled me with her, handing me a big fluffy terry-cloth towel. "Just pat yourself dry," she instructed me, "And sit on the throne." From her vanity she produced a can of shaving cream, a pink razor and small pair of scissors. "Just sit still," was all Marie said as she began to first trim the dark hair from my legs and under my arms, then to lather my body and with short strokes to shave me from neck to toe. She used two different blades an d she must have used the entire can of shaving cream before she finally told me to go back into the shower where I rinsed away cream and hair.
When I stepped out again my body looked very different and much more feminine. Marie handed me a bottle of Jasmine-Scented Body Lotion and left. As I started to apply the soft gel I could feel how smooth and delicate my skin now felt. Rubbing in the lotion with the scent tickling my nose and the sense of achieving a level of femininity I had never reached before, I felt a twinge of excitement and began to stiffen. When Marie came back she saw what was occurring, with a wry smile she said, "That would distract everyone. Let’s take care of this for now." She dropped a tiny bundle and plopped a blob of Body Lotion into her hand and reaching for my to me. I held it out to see which side was the front and then placed my feet inside the legs. The cool material swiftly warmed to match my skin as it slid on.
Marie had me turn around and encased my torso in a red and black satin corset with six suspenders. The hard fabric constrained me ribs as Marie tightened the laces. The roll of flesh I had seen disappeared and the little flesh around my breast formed the illusion of cleavage. The suspenders slapped against my legs as Marie had me take a deep breath and pulled on the laces. After I exhaled I found that I could not breathe as deeply as before.
Taking my hand, Marie turned me and took me back into her bedroom where she had me sit on the bed. A pair of black silk seamed stockings lay beside me. "Try to get the seams straight," Marie asked as she went into her closet. I rolled down one stocking and pointed my foot into the dark O. Silk slithered up my now bare leg, the sheer material and hairless flesh sending a surge of lust into my cocooned member. Struggling to keep the seam in line I tussled with the garter snaps but soon had all three se cured and then did my other leg. Finished with the garters I ran my hands over my legs, turning my calves and looking at the line of my leg wallowing in the sensation.
Marie was smiling at me from the closet. She was holding a red leather dress in her arms. "Kerry, your legs are going to get you anything you want. And with this," she extended the dress, "You’ll look hot." Unzipping the back she motioned for me to stand and as I did so I felt the blood rush away from my head. Swaying for an instant I panicked when I realized I was not breathing the way I was used to. Marie’s hand steady my arm and I found a new pattern to my breathing. She directed my arm upwards and like a child she slid the dress over my arms, head and shoulders. My somewhat large hands popped through the sleeves as my head emerged. Marie tugged the leather down over my corset, behind and thighs. She zipped me in and the leather fitted itself to me. The butter soft fabric caressing my bare shoulders and held my thighs tightly. I thought that with every tiny breathe that I took that the leather would explode. Instead the dressed warmed to my excitement and enhanced my "Now," Marie placed her hands on my shoulders and steered me to her bedroom’s vanity. Seated, Marie turned the chair so that I face her. She frowned, "That wig you had was awful and would ruin the look. We’ll have to do something with what you have." My chestnut brown hair was fairly short and Marie stared at my head for about five minutes before she took brush an comb in hand. Her hand then flew over my head as she fought to find the look she sought until she finally she grabbed a scissors. Before I could say no, Marie had started to cut. The snip of the sharp steel echoed in the room and in my ears when suddenly it stopped. Now Marie took some gel and combed out my hair. As she stepped back to look at the effect, I went to turn to face the mirror. But Marie prevented me, "When we’re done you can look. Not before."
"First things first." Marie took up my hands and cleaned my nails and with an emery board gave them a more delicate shape. Then she applied ice pink nail polish on each finger. "Let those dry for now," she said as she took up a handful of brushes and crafted my face. I closed my eyes and relished the scent of foundation, blush, shadow and gloss. A sharp pain above my eye caused me to open my eyes and look at Marie who had a tweezers in her hand. "Your eyebrows are little too thick. I’m just going to thin a bit." For long minutes Marie plucked me and the pleasure of the surcease of the act was marvelous. Then I was turned around and from right behind my ear Marie whispered, "Take a look at the new Kerry."
The face in the mirror was mine, but I looked the way I had never been able to acquire on my own. Satiny honey brown eye shadow and long black mascaraed lashes brought attention to my shining brown eyes. Rosy pink blush created a hollow and defined my cheekbones, while velvety pink lips quivered with joy. My hair was cut to pointy ends around my ears and short bangs dangled onto my forehead, with swirls of hair around my long neck. The face in the mirror was me, and I was Kerry.
"Just some last touches." Marie’s voice was now across the room. I turned again to face her with tears behind my eyes. "I think that with your legs, these will look great." She held up a pair of black patent leather spike heeled ankle boots with a tin y silver strap across the instep. Still sitting I took them from her and pointed my stockinged foot inside. Silk and satiny liner allowed my foot to glide into the boot that formed itself around my toes. With the second boot on I turned and twisted and admired my legs, Marie was right about them. "Here," Marie slapped playfully at my legs. "Stop looking at yourself and put these on." Her hand deposited a tangle of silver and I placed three bracelets over my wrist and two plain rings on my left pinkie and right index finger. Marie was spraying me with Charlie as I looked down at my hands.
Just then the front doorbell rang and I remembered what this was all about. There was going to be a party and I was going to be the star. Marie smiled at me, "You look more like a woman than most women. And those legs!" She tossed aside the perfume and took my hand. I stood and staggered for a few moments unused to wearing heels and having such a tight skirt encircle my legs. Marie helped steady me and with short steps I left the bedroom and went downstairs. My breathing was shallow and I could feel my heart starting to leap out of my red leather dress. Marie squeezed my hand and left me standing at the foot of the steps as she opened the front door. I wanted to scream, I wanted to run, I thought that I was going to be killed, I trembled and asked myself what I was doing.
Swallowing a hard lump I tried to stop my knees from knocking. A gust of cold air swept into the room. I thought my heart would stop beating from fear. Suddenly I heard a long breathe escape and a voice say, "Tommy!?" It was Mike, staring at me wide-eyed. "You’re beautiful!" He took a few steps forward and I quivered, trying to find my voice. Mike paused before me, his eyes ogling my legs. Without a thought I spun on the balls of my feet to show him all of me. The heels pushed out my tightly leather clad rear and I raised one hip to enhance the effect.
"I can’t believe it." Mike’s voice was husky.
Turning towards him again, I kept my eyes downcast and saw a swelling in the crotch of his Levi’s. He took a step forward and I quickly looked up in time to see his voracious lips descending. They wrapped around my glistening lips and our tongues shyly danced. His left arm went around my shoulder and his right followed the curve of my torso to my hip. I shuddered and ground my groin into his. The swelling in Mike’s jeans was growing and as it built up his right hand started to caress my leather bound rear. Sensations cascaded through me and I almost felt as if I was about to faint.
Suddenly our lips parted and Mike’s hands were wrestling with the fly of his Levi’s. A step backward and I knelt in front of Mike as he peeled away the denim. Ice pink nails ascended to white briefs. From beyond the cotton a large lump appeared and for a moment I thought about how it compared to my step-father’s and how it shamed my small member. But that thought was fleeting as Mike half-stepped towards my waiting lips. Eye half-closed I fully open my mouth and began long luxurious licks of my tongue. Soon I felt a pulsing on the inside of my mouth and from above heard moans. My nails were biting into the hard flesh at his hips. Mike was now pushing his hips into my face as he held the sides of my head. Then all at once a spurt hit the roof of my mouth. For a second I gagged and then swallowed and kept on swallowing and milking Mike until he finally extracted himself.
From the front door I heard a hard sardonic laugh. My step-father stood there, an arm draped across Marie’s shoulder. "He’s all yours Mike. For tonight." He leered at me. "Tomorrow tonight he’ll start to earn his keep." A hand disappeared into my step-father’s pocket, "Here’s a hundred." He stepped away from Marie, "Take my ‘son’ out and show him a good time. Make him feel like a woman."
Slightly embarrassed, Mike pulled up his jeans and zipping himself he took the offered money. I came to my feet staring at my step-father who would not look at me. From the hall closet Marie took out a long white rabbit fur coat. She smiled ruefully and giving Mike the coat scurried upstairs. Mike held out the coat and I slipped my arms inside. Seconds later Marie was back with a small black velvet purse and pair of cashmere lined winter white leather gloves. As I pushed my hands into the gloves, Mike was taking me by the elbow and walking me out the front door.
"Bring her home by midnight. She’s going to have a hard day tomorrow." My step-father’s rough laughter followed us down the walkway to Mike’s car. "I’m sorry about that," he said under the streetlight as he paused in front of the car. "But not about you. You probably didn’t know that I was bi, did you?" He kissed me again and I melted into his arms not caring that I was a man standing on his tiptoes in a pair of high heeled ankle boot dressed like a sexy woman. All that mattered was Mike’s warm tongue and he sure hands. Tomorrow would be later, but tonight was now.
Part Three
The car horn brought us up short. Mike was still holding me and I could feel him breathing deeply as his tongue slipped away from my hungry mouth. Slanting winter sunlight created long shadows. Our breath steamed as we broke our embrace. The chilled air swirled around my stockinged legs and pantied bottom but I felt nothing except elation. A dream, a fantasy from the past come to fruition as I watched Mike open the car door for me. Without a thought I turned my leather encased torso so that my tiny rear was pointed at the bucket seat. One gloved hand smoothed the back of the red leather and I bent at the knees. Leather on leather I kept my knees together and pointing my feet swung my legs into the car. Mike closed the door and scampered about to seat himself. A big grin on his face, he slipped the key in and the ignition caught, the engine purring with contained heat.
"Where we going?" I asked as he pulled away from the curb. My voice still sounded too masculine, though I was aiming for a husky, sexy sound. "I know a little Mexican place, not far from here." Mike cast his eyes at me.
"Then I thought we might go dancing?"
"I haven’t danced since ..." My voice cracked at the end. Tears welled as the memory of Penny and our marriage sprang to life. Trembling with anxiety my situation suddenly dawned on me. What was I doing? How’d this happen so fast? Shoulders racked as I fought back the tears. Totally confused the world seemed to shrink before my eyes.
"Tommy?" The sound and the hand on my shoulder brought me back to reality. "Tommy? You alright?" My eyes remained downcast, I was ashamed. I’d allowed myself to give into a fantasy I had thought long dead and forgotten. I’d given into pleasure and sensuality and now I was sitting in a car masquerading as a woman with someone from my past. I had to get out, to go back, to ... "Tommy, tell me what’s wrong." Mike’s hand made me feel dirty. How could I like the sensation of his hand on me, of the leather dress against my flesh, of theætightness of the corset, and the arch of my booted feet. This was all wrong, wrong! My voice was clenched shut and all I could do was shake my head. Mike slid his hand across my shoulder and pulled me closer over the bucket seats. "There, there," he cooed, "everything will be fine." His hand brushed below my eyes and I felt his flesh absorb the dampness from my cheeks. Unwillingly I found solace in his embrace.
For long minutes we sat there, unmoving. Raging emotions sought a balance within me and after a while I was able to breath regularly again. One gloved hand on Mike’s chest allowed me to push myself upright. "I’m sorry," I croaked and he gave me a tissue to blow my nose with. Wiping my face, I saw traces of the make-up job Marie had performedon me. "This is all too quick." I began to explain. "I can’t do this." My hand waved to encompass the world. "Can’t do what?" Mike leaned back in his seat. Then I realized that he had pulled the car over to the side of the road.
"This," and now my hands pointed to me. "I can’t be a woman. I must look like a joke. I’m sorry." Ashamed again I turned my head to look out the side window. The sunlight had evolved into a deep blue star flecked night sky. Dimly I could see my reflection and wanted to laugh at how pitiful I must seem. "Tommy," Mike touched the side of my neck. "Damn, I can’t call you Tommy. You’re not Tommy, not when you look so feminine, so sexy. You must have another name, no?"
"Kerri," again my voice cracked. So much for being sexy! "Kerri," Mike repeated. "A soothing name." His palm rested on the side of my neck now. I could feel his fingertips and wondered if he could feel my pulse leaping. "Let me sooth you, Kerri."
"Mike, don’t," I began trying to turn further away but there was nowhere to turn to, nowhere to run. "I don’t know what happened back there at Marie’s place, but I can’t go on with this charade." My reflected eyes saw the quivering man behind the streaky make¬up.
"Well, you might see this as a game, but I see a lovely person who is finally doing what makes them happy." Mike slid his hand away. "I’ve had problems too, you know." His voice fell lower. "Staying here and trying to deal with what I wanted. I envied you, envied that you tried something new, went somewhere." "But look at me now!" I almost shouted. "Nothing worked out, lost my job, lost Penny. And now this!" Swiveling my head I faced Mike. "Not much of a man am I." "Depends on your definitions." Mike replied. "You took some chances, and yeah, some of them didn’t work out. But you tried. And this," he looked pointedly at my feminized body, "is another try. Don’t give up on it until you’re sure." "Sure!" I started to laugh and then I couldn’t stop. Mike joined in and the tension slowly dissipateæ. When I finally regained some composure I looked Mike straight in the eye. "If you’re sure that you don’t mind being seen with me looking like this then why not!"
"Only if you’ll fix your make¬up!" Mike grinned. "You look like something the cat dragged in."
Leaning over, I gave Mike a quick kiss on the cheek and then took off my gloves. Fishing in my purse I found what I need to do some repair work, powder, blush and lipstick. As I worked on my face in the small round mirror I began to relax. Mike was right, why not give this a chance? This could be fun. And when was the last time I’d had fun. Penny leapt to mind again, but this time the pain of loss and the anxiety of what I was doing was lessened. "How’s that?" Snapping close the compact, I faced Mike.
"I’d kiss you but you’d have to do your lipstick again." Mike smiled and started the car again. My breath was deep and relaxed again as the car spun away down the road. Watching the lights ripple by I was suddenly shocked to feel Mike’s hand on my leg. His eyes on the road, he drove with both hands directing two different machines. Head pressed against the head rest I moved my leg closer to Mike, spreading my legs. His strong long fingers went from thigh to knee to inner thigh and upwards. Nestled within the black silken panty my own desire fought to spring to life to no avail. Trapped and constrained all I could do was gyrate my hips into the vee of the bucket seat as Mike continued his journey along my leg. When he reached the stocking top his fingers tickled the exposed flesh and snaked under the garter strap. Between my legs I could feel myself start to percolate, and then boil. The groan that followed my shivering rear and trembling legs had Mike give a squeeze to my pantied groin The rest of the drive raced by as did my thoughts and feelings. "We’re here," Mike announced, turning off the engine. I glanced out at the orangy colored street and as I gripped my gloves Mike was out of the car and opening my door. Holding my knees together I swung out my legs and using Mike’s strong arm levered myself out of the car. He shut the door and with his arm entwined with mine we walked to theærestaurant. All the doubts I’d had seem to vanish. The spicy sound of heels on pavement, the sensation of Mike holding me, the aroma of my perfume all alleviated my fears. Instead of anxiety I relished the feelings and for a few steps laid my head against Mike’s shoulder. He softly squeezed me and my heart nearly exploded with joy.
The restaurant was dimly lit and the hostess pleasant as she showed us to our seats. For an instant I found myself looking at how she was dressed, how the outfit set off her stocky torso and wondered how she got her make¬up to look so good. Then we were sitting, ordering and eating. No one paid any more attention to me than any other customer, except for Mike. He would touch my hand, or teasingly stork my leg with his foot. As the meal went on, he did most of the talking, which was a relief for me since I was still unsure of projecting a feminine voice. Mike told me all about the rest of our high school crew and what had happened to them. When coffee and dessert were being served I felt the urge to urinate. Panic! Where would I go, raced through my mind and was almost instantly followed by the thought of having little choice dressed in this fashion. So, with a deep breath I excused myself and went to the Ladies Room. Seeing my painted nails push open the door, I dreaded seeing another woman inside, but the room was empty. Quickly I went into a stall. In the small stall I began to struggle with my dress. At first I thought of removing it, but that was not only awkward be foolish, I’d never get it back on!. Instead I pulled up the hem above my hips and pulled down the panties and undid the flap on the corset. Still standing, I realized that urinating this way would make a mess, so like a lady I sat on the chilled seat and relieved myself. With the dress still hiked up I grabbed a piece of toilet paper and wiped myself, not wanting to stain the panties. Then standing I worked the panties back up, making sure to tuck myself in before tugging with the corset flap and sealing myself away again. Next I pushed down the leather and took some time straightening out the material. Finally I flushed and opened the stall door. I was still in luck as the room remained empty. Taking advantage of this void, I went to the sink, washed my hands, amazed at how the nail polish made them look so much more feminine. Then I looked in the mirror. A shy smile hit my lips as I saw the new me. And then I softly cursed at not having brought my purse as I noticed that my make¬up needed some touching up. That thought sent a shiver through my soul and I looked away, the feeling seemed so female to be concerned with my make-up. Holding the sides of the sink I took a deep breath and looked again at the mirror. Though by no means a stunning beauty I appeared to all outward semblanceæ a woman. This was something I’d thought about and something I’d made happen. I could always stop after tonight, came the thought. Yes, that’s what I’ll do, after tonight I’ll find a job, move out and get my life back. But that was tomorrow and there was still the night and Mike. With a long shuddering breath I brushed at my hair and pulled open the door just as someone else was entering. We smiled at one another as we passed. Back at the table the coffee was waiting and so was Mike. Again he filled the time by regaling me with stories of one-time mutual friends. All too soon he paid the bill and was escorting me out of the restaurant. "Still up for dancing?" he asked as we drove away.
"I’m sorry Mike," I began. "Its been a long day. Could we just go home?"
"My place or your’s?"
"Mine, I guess." I touched his knee. "I’m really sorry. This has all been so sudden."
"Don’t worry, and don’t be sorry. I had a great time and you were simply marvelous." He smiled at me. "Now that you’re back we have all the time in the world."
"Thanks Mike." I snuggled into the bucket seat and tried not to think as the car swept me home. The lights were still on as we pulled up. Another surge of panic. My step-father had said something about a coming out party for me! Had he been serious? Had he told my mom? And what could I tell her? I began to tremble until Mike laid a hand on my knee. He stared into my eyes, "You’ve nothing to worry about. You look lovely."
"But about my family? What about my mom? Do you think my step-father told her?"
I could hear the edge of hysteria.
"You could go to Marie’s house."
"Yeah, you’re right. I could borrow some clothes..." The laugh was less panic-stricken as I realized that I was wearing her borrowed clothes right and now and that was the problem.
"I’m sure she has some jeans and a sweatshirt you could borrow. I’d loan you my stuff but it’d be too big for you."
"Thanks again Mike." I leaned forward and kissed his open lips. He was right I’d go to Marie’s change and slip into the house. Then I could deal with whatever my step¬father had concocted. Mike returned my kiss and drew me closer. Our tongues slid over one another, the rough and tender caress. His teeth nibbled at the very tip of my tongue as I extracted myself. My eyes closed and senses on fire it took me a few minutes to realize that someone was tapping the window. With a gasp I opened my mascared eyes and turned in the seat. My step-sister, Toni was at the window! She was a big woman, about an inch or so taller but weighed at least thirty pounds more than me, though much of that was muscle. Her hard face, physique and dirty blonde hair gave her the appearance of a Roller Derby Skater. Now she was standing in the street with a wicked leer on her thin lips as she saw me.
My heart skipped and thudded fighting between panic and the wish to die of shame. Toni simply crossed her arms beneath her protruding breast and waited. There was no thought of running to Marie’s now. No escape from having the entire family, maybe the whole neighborhood know about me, about Kerri. With one backward, sad smile at Mike I pushed open the car door. "I’ll cal you tomorrow," Mike said as I exited. Beyond speech I nodded and let Toni shut the door, as she told Mike, "Better call afternoon, SHE has an appointment tomorrow morning at Studio 19."
An audible gulp thundered in the night, followed by Toni’s biting laughter and the sound of Mike’s car easing away. Studio 19 was a fancy beauty salon with tanning parlors and massage tables that I’d seen advertised on television. Before I could think any more of that ordeal Toni had roughly seized my upper arm. She half-dragged me toward the house. I began to whimper, "please, please don’t do this to me, please."
Toni merely laughed harder. "You’ve done this yourself you little fag. Listen to you begging like a girl. You’re pathetic, what a poor excuse for a man." She twisted open the front door and pulled me after her. My feet slipped in the heels and I sagged against her firm body. Eyes downcast I began to cry. "Oh stop it, will you." Toni shook me and with her arms on mine stood me up straight. "There’s no one else home. Dad took your mom out to dinner. It’s just you and me, babe." She pulled the wig off my head and for some reasion I felt naked, as if I had been exposed. Toni eyes me, "You don’t really need a wig, girl, you have such nice femme features." Again that leer filled her face. "What do you want?" I choked out. I almost added that I’d do anything but that seemed pretty obvious to me.
"Well, Kerri," she stressed my femme name, "I want a lot of things. But tonight I want you."
"Me?!" Taking a step back I bumped up against the wall. Toni stepped forward. "Not as a man!" She sneered. "Look at you. You’re more a slut than a man! Though you do look very sexy in that leather dress. C’mon, I’ve some games we can play upstairs."
Toni turned and for an instant I thought of running. Then I became of aware of how I was dressed and that aside from Marie, who’d helped me into this red leather dress and black patent leather ankle boots, that there was nowhere for me to run. Trapped by my own fantasy.
Slowly I followed Toni. Walking up stairs with 4" heels was a new challenge, I kept thinking that the shaft would snap under my weight so I focused my balance on the tips of my toes. At the head of the stairs Toni waited at the door to her bedroom. Since I’d returned after the divorce and losing my job, I’d never been in her room. The queen size bed filled most of the space along with a chest of drawers and footlocker under the window. The room seemed neuter with off-white walls and ceiling paint and no other ornamentation. Toni allowed me to enter and then shut the door.
In silence she went over to the footlocker and undoing the hasp she started sorting out garments. She tossed things onto the bed, black and red bras, panties, corset-like things. I stood there watching her the aroma of leather filling the room. Unwillingly I felt myself respond to the scent and tried to move my hips to accommodatethe growing pressure. Finally Toni stood up holding a long pair of boots in one hand and red stiletto pumps in the other. My eyes bounced back and forth between the two and Toni seeing my reaction laughed again. I was growing to hate that laugh.
"Strip." She tossed the boots and pumps atop the pillow and glared at me. Under her gaze I took off the white rabbit fur, the leather glove and searched for a proper place to lay them down. Only the floor beckoned and so with knees together I bent at the hips and laid them out. "My god," Toni howled "you even move like a woman! Is that why Penny left you? Did she hate you for being so pretty? Or did she find you with someone like Mike?" Her words opened the scabbed wound of my lost marriage and I wanted to scratch her eyes out. Instead I merely shook my head no and got on with undressing. There was a struggle with the zipper on the dress and Toni made no effort to help. With convoluted and twisting arms I finally undid the zipper without ripping the dress. Stepping out of it I folded the garment and placed it over the coat. For a moment I stood there until Toni said, "Everything." Resigned to further humiliation I leaned back against the door and tugged off the ankle boots, next I undid the garters and rolled the stockings down. Toni’s laughter filled my head. Getting the corset off was more of a problem as I wrestled with knots and laces and the groin flap, but finally I was standing there with only the black silk panties covering me. "That too." Toni pointed, "after all you don’t have much to hide!" Turning my back to her I stepped out of the panties and held them before me. "Oh, such modesty," Toni snickered. "Turn around, now!" I did as she asked, though I retained the panties in the vain hope of keeping some dignity. But that was dashed as Toni strode around from the opposite side of the room and tore panties from my grasp. Now all I had on was my make¬up and nail polish. Toni used her forefinger to flick the head of my flaccid and retreating penis. With a gasp I jumped away and she looked me up and down. "Well you’re still seem pretty hairless, but to be safe you’d better go shave again." She opened the door and naked I shuffled into the bathroom. Toni followed "I’m going to leave you your attire for the night in my room. Once you’ve shaved get dressed and come back downstairs." I nodded and got to business of shaving,legs, chest, underarm. When I was done I ran a quick shower and with a towel about my waist I went back to Toni’s room. On the bed I saw a collection of red leather garments. Drawing closer, I fingered them, separating them and trying to decide which went on first. I settled for the waist cincher. The supple leather was chill against my flesh but quickly warmed as I positioned the garment and worked the laces as tight as I could. The leather helped to flatten my stomach though looking down I could not see if I’d made any female curves on my torso. Next I snaked on the red bra and had to take it on and off a few times until I had the right length on the shoulder straps. The red again my shave chest was a vivid contrast. I spotted a garter belt and hooking it around my waist, below the cincher I straightened the straps and looked for a pair of stockings. Toni had left a pair of sheer red ones that slithered over my legs. Getting the front garter was not a problem, but I spent long minutes wrestling and twisting the rear snaps. Frustrated that the snap would not hold I almost tore the stocking. Finally the garters held and with a sigh of achievement I looked for the next item. All that was left was a tiny thong panty with silver side snaps. I undid one snap and stepped into the panty. The thong seemed to disappear between my small, tight cheeks and with a tug I managed to do up the snap. The panty pressed my small bit of manhood into a flattened mound and I saw that I not shaved close enough as a few stray hairs peeked from behind the warming, molding leather.
At last I took the stilettoes and seated on the edge of the bed I scrunched my toes and wiggled my feet into them. Standing up I fell back onto the bed. Never had I had tried on such a high heel. As I glanced down I estimated at least 5" if not 6" of spike. Closing my eyes I move to the edge of the bed again and this time I slowly pushed myself upright. I teetered for a moment and then found a modicum of balance. Taking extremely tiny steps and with my arms held out for added security I practiced walking around the room. The rug caught at the heel and made the task even more daunting. This would require hours of practice that I did not have, so gritting my teeth I headed for the stairs. If walking up in 4" heels had seemed a climb up Mount Everest, then descending in these spikes was like entering the Inferno. Turning my feet so that the entire sole was on the tread I gingerly made my way down. The thought of falling and breaking a leg or arm made me wondered how I could explain my clothing and nail polish to the EMS squad.
With that thought I reached the bottom and still going slowly I crossed into the living room. The strobe of a flash greeted me followed by applause. Blinking my eyes, I feared that there were a thousand eyes looking back at me. Only Toni was there. She had donned the black garments and stood in the center of the room in black bustier, her nipples peeping over the edge, black garter belt and panties festooned with silver studs and black over the knee spiked boots. A camera dangled from her hand. Though not a stunning beauty she projected an aura of sensualityæ that filled the room.
"My, don’t you look hot!" She placed the camera on the coffee table and walked up to me. "Dear, you ruined your make-up. Here sit down and let me fix you." She sat me on the sofa and darted upstairs to return with her make-up kit. "Close your eyes. You’ve such a petit face," Toni said as she worked on me. "Why didn’t you do this early. I’ll bet if you’d done this when you were 20 you’d be married to some really hung stud right now." Her chatter made me cringe while her brush strokes and the feel and odor of the cosmetics made me squirm on the sofa pillow.
"There," Toni announced. I saw the afterlight of a flash though my shut eyes before she said, "Open your eyes and see." She held an enlarging mirror in her hands and the sight before me was no longer petit but wanton. Toni had given me a dramatic look, if not a whorish look with blue eyeshadows, deep red blush and brilliant gleaming red lips. "You look good enough to eat me." She licked her own painted lips as she let the mirror slid to the floor. Her strong arms rested on my shoulders and then with one quick movement she brought my head to her black pantied groin. "Use you tongue and teeth to move the panty, bitch." She kept my head pinioned and I could feel her heat, smell her musky deep desire. With a gasp I closed my eyes again and sought to move aside the strip of the panty that covered her waiting flesh. My nose nestled in her pubic hair and with nibbles and licks I managed to slightly move the panty. Opening my eyes, I saw her glistening before me and with now smeared lips I began to delve into her. Her grip tightened as I spent long minutes probing and quivering with my tongue. Toni seemed lost, as did I, and urged on by some unknown and insensate passion she was shimmying and quaking in her seat and I could feel her liquid desire oozing and covering my tongue.
"Marie was right," Toni’s husky voice whispered. "I can’t wait until the others meet you." Others?!!
© 1998 Jojo Bruno
The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.