I began crossdressing at 12, but it wasn't until I was 17 when I dressed up completely for the first time. When my parents went away for the weekend to Atlantic City, I took advantage of the opportunity to explore my feminine side to the fullest. As soon as they left the house that summer morning, I got out of bed, padded naked into the bathroom, drew myself a bath and poured a packet of Caswell & Massey sandalwood powder into the steaming water. The scent was like a forest after a heavy rain, the tiny suds crackling softly as I climbed into the tub and let the water's heat seep into my body. After relaxing for awhile, I gave myself a panty shave, removing every trace of hair from my cock and balls. What remained was a thatch of slightly kinky tendrils just above the base of my shaft. I thought it looked pretty sexy. With that done, I stood up and turned on the shower and let the water drain out. The hot stream of needles pounding against my skin made me crazy with lust, but I resisted the urge to masturbate just yet.
I rinsed the last of the suds from my feet and stepped out of the bath, reaching for a large, thirsty white towel to dry my body. Next, I dusted my skin with a richly scented powder and a fine sable brush, then sat down at the vanity to do my nails. Using an emery board, I buffed my toenails to artistic perfection and placed cotton balls between the spaces of each toe. I painted the nails scarlet red, carefully smoothing out the lustrous Chanel varnish with the soft little bristles. I did my fingernails with French tips while my toes dried, thinking about how to do my hair and face. When my finger nails dried, I applied a generous amount of styling moose to my wet curly hair and arranged a short, yet feminine couiffure. At 17, it didn't take much makeup to make me look girlish. With just a little foundation, mascara, blush and a touch of red lipstick, I was ready to move on to the next step.
I entered my parent's bedroom and went to my mom's huge walk-in closet, surveying her highly sophisticated wardrobe. From the lingerie drawer, I picked out a pair of Lise Charmel panties and stepped into them. Then I shimmied into a microscopic black YSL minidress with pointe d'esprit inserts at the sides. This dress was clearly meant to be worn with no undergarments, so I took the panties off, feeling my cock beginning to stir. The collection of sexy shoes included stiletto sandals, platforms with chunky heels, pumps with knotted vamps but I took a particular interest in a pair of black Charles Jourdan four inch sandals with three tiny straps to cross over the toes and lace bows at the centers. I was fascinated by how dainty my feet looked in the strappy lattice work of the skyscraper sandals, the cleavage of my red-painted toes criss-crossed by the gleaming straps of supple black leather. Within about ten minutes, I found myself walking in the sey heels with a sexy, hip-swaying stride. Just walking around the room was like an erotic exercise. The more I clicked across the floor, the more my swollen cock against the exquisitely form-fitting dress. Soon, I was literally trembling with lust. I went before the bedroom's full-length mirror and posed in a variety of sexy stances, pausing for several moments when I looked my feminine best. While gazing at the points of my stiff nipples straining against the glimmering minidress, I imagined what it would look like if I had a firm set of breasts and by this time, clear streams of pre-cum were literally pouring from the swollen head of my erection.
I hoisted the hem of the dress up to my waist, curled my fingers around my shaft and began stroking it hard and fast. After about five minutes, my entire being exploded like a white-hot burst of energy. My body convulsed in a series of powerful spasms as my cock spurted rapid bursts of cum, splattering in a lewd rain across the mirror. I was so overtaken by the sheer force of my climax that I was barely aware of my own voice when I sharply cried out my self-loving passion. I'd experienced many great orgasms before, but this was definitely the most powerful ever. I loved dressing up completely and knew from then on that there would be no turning back.
One good thing about my having been a teenager before the Internet age began booming was that I had no knowledge about society's labels. I didn't understand the difference between crossdressing from transvestism or a transgendered person from a transsexual. There was no pressure to try and figure out whether my secret past time was a sexual thing or something deeper. No one was going to find out about it anyway, right? I had the whole weekend all to myself to just be a girl. I only masturbated one more time that evening and only twice the next day which was highly unusual for a teenage hormone on two legs like me. I ended up just doing the same ordinary things I normally did on weekends; only dressed as a girl. Well, that's not entirely true. I did put a bit of a spin on things, like cooking breakfast with nothing on but an apron and six inch wedge heels. I normally cut the lawn on Sundays in a t-shirt, jeans and sneakers, but this time I risked being watched by the neighbors doing this chore in a skimpy self-made pair of denim short-shorts, a high-cut pair of red satin panties, flip-flops and nothing to cover me up top. I'll never know if anyone saw me dressed like this.
By the time the yard was finished and I'd taken a shower that day, I realized it was getting close to sundown and I knew that my parents would be back home in the next few hours. Sometimes they even returned an hour early so I chose to be careful and put back everything the way I found it and get my homework done. I hated that Sunday evening realization that the weekend has flown by and it was responsibility time again. Within the next twelve hours, I'd be sitting in homeroom class all over again in boy mode with a bunch of people I hardly knew, except for one other kid.
My best friend, Devin Witherspoon was not only my best friend during my senior year of high school, but my only friend. He was a fellow honor student who sat next to me in homeroom class. Just like me, he was shy and awkward; a wallflower at dances and extra-curricular activities. He could have dated just about any girl he wanted to if he knew what he had to offer. However, if he'd been aware of his good looks, he may have been impossible to deal with. His modesty seemed to enhance his sweet personality.
Upon learning that we lived near each other in our small northern New Jersey suburb at the beginning of the school year, we began walking to and from school together, eventually developing an easy, comfortable comradeship. We talked about everything, but my physical attraction to him was something I chose to keep to myself since I hadn't yet come to terms with the fact that I might be bisexual. I'd always considered myself to be purely heterosexual, so my attraction really surprised and alarmed me.
I was quite certain that Devin was one the prettiest boy I'd ever met in my life. He had a thin, angular body and a certain feminine air about him combined with a look of rare serenity for someone so young. His demeanor was one of quiet reserve, except for when he spoke about a subject that fascinated him. Then, his features would become animated with a lively intelligence which I found terribly appealing. I sometimes wondered if he'd ever experimented with makeup or feminine clothing, but of course, I couldn't just come right out and ask him that. Instead, I just made use of every opportunity I had to just look at him without appearing in awe of him or love-struck.
His androgynous looks amazed me; pretty eyes as blue as a cloudless sky, fine aquiline nose and a wide, sensuous mouth , the edges of which were always upturned in just a trace of a smile. With his longish blonde hair curling crisply over his temples and high cheekbones, he reminded me of some of the flattest waif models that were so popular in the early 70s whose images graced the pages I'd seen in my mom's issues of Vogue and Harper's Bazaar. I've never any racial preference but thought our contrast would be pretty sexy, skin-to-skin.
The first time we made small talk in homeroom, I was acutely aware of the way his sexy, narrow eyes lingered over my face and body, not just once but two and three times. Could he be attracted to me, too? I wondered. I was so glad that we'd both chosen to sit at the very back desks of the room, where no one would notice how I allowed my eyes to drink in the sight of him when I thought he wouldn't notice.
Devin introduced himself to me formally in the middle of our first conversation.
"By the way, I'm Devin", he said in a quietly unassuming tone, extending his hand. I took his hand in mine and shook it from across from across our desks, letting mine linger just a moment longer than necessary when I told him my name. His eyes dropped downward and a rosy hue came to his face. I realized that my flirty little handshake actually made him blush! Hopefully it wasn't just wishful thinking on my part.
One day, while walking home from school, we tossed around the idea of catching a movie or going to the mall to hang out and people watch so we exchanged phone numbers. So there I was at home one night itching to call him. I picked up the phone, dialed his number, but then stopped and hung up. I repeated this process three times before I finally allowed my call to go through. When he picked up, I didn't really know what to say and asked him if I'd caught him at a bad time, half-hoping he'd tell me that I did.
"No, I was just doing some homework", he replied.
"On a Saturday night" Devin? "Instead of hanging out with some hot girls?"
"Well, yeah. See, I had three dates lined up consecutively for tonight, but they all fell through."
"That's not funny. You could actually do that if you wanted too, if you put yourself out there."
"Yeah, you too, kiddo. So what's your excuse for being at home tonight?"
"My dates fell through, too." "Well, in that case, we might as well be doing our homework together."
I couldn't believe my ears when he asked so I invited him over.
"Yeah, but it's like ten o'clock already. Wouldn't your folks mind?" "I've lost track of the time. Weren't your parents going to Atlantic City again this weekend?"
"Yeah, Dev. They should be getting there just about now. They won't mind the hour. I think they'll be just glad to see I have a new friend."
"Okay then," he replied. "I'll be there in about half an hour."
We started out with art history in my room, which was one of my favorite subjects. Devin liked art, too, but couldn't understand Picasso's cubism so I tried my best to explain it to him.
"You're pretty deep aren't you?" he asked, once he started to get it. "No, actually I'm pretty shallow, Dev." "You're basically a loner like me, right?" "Yep." "I thought at first that you had some sort of racial hang-up going on." "Why would you think something like that, Devin?" "Well, there's only a handful of other black kids at our school and you seemed to have some sort of special common friendliness with them. But then I'd see you talking with all different kinds of kids once in awhile and decided that wasn't it." "Yeah, I like everyone, Devin, even white kids like you." "So what did you think of me at first?" "Do you really want me to answer that?" "Sure, I've probably heard it before." "Okay. When I first saw you in homeroom class, I um, thought you were a girl at my first glance. I'm sorry. Maybe i shouldn't have told you that." "Don't be sorry. That's nothing new. But why didn't you change your seat or something once you realized that I wasn't one? You didn't mind being seen sitting next to such a girly boy?" "I didn't say it bothered me, did I?" Uh, no. I guess you didn't."
I couldn't help but wonder if Devin was asking me what else I'd thought about him because I wondered if he was as attracted to me as I was to him. Thinking this would probably be the best time to find out for sure since we had complete privacy for a change, I decided to go for it. I rose from the desk and began to leave the room.
"Hey, where are you going?" he asked. "Keep studying," I replied. I'll be back in a few. And to answer your question, I think that you have an open mind, Dev. At least, I hope so."
My opportunity to reveal my feminine side to Devin had finally arrived so I took total advantage of it, not knowing when it would come again. As soon as I reached my bedroom, I stripped out of my t-shirt and blue jeans. I'd already laid out a sexy outfit, having hoped things would turn out as well as they had so far. I sat at the edge of the bed, curled up one leg of my sheerest pair of black stockings and smoothed the soft fabric over my painted toes, up my calf and thigh , repeating the process with the other silky stocking. Then I stood up to pull the hose up my thighs, over my stiffening cock and around my hips. I wriggled my body into my favorite short, low-cut black lycra minidress which showed off the large points of my nipples and showcased my long smooth legs. In the bathroom, I put on a little makeup and lipstick and smoothed some finger waves into my hair with a little styling mousse. I was completely satisfied with my feminine look in my reflection in the mirror and it was now or never.
I slowly entered the study with my hips swaying ever so gently, awaiting Devin's reaction.
"Oh my God, I almost didn't recognize you , "he exclaimed. "Damn, you look hot."
I let out a long sigh of relief. He asked me to turn around and I pirouetted with as much grace as I could muster.
"I always knew you'd look beautiful this way, but I didn't expect you to..." "...You've thought about seeing me dressed like this?" "Yeah, but, wow. Even your voice sounds different now. How do you do that?" "This is my natural voice really. I'd speak this way all the time if I didn't have to act so boyish at school."
Devin rose from behind the desk and came within a few feet from me.
"I know I'm gawking at you, but I just can't get over the way you look. Do you know there's not a soul in the world who wouldn't think you weren't a real girl looking like this?"
I'd been dressing like this for a few years, but I never thought I could actually fool anyone. I was convinced that Devin really thought that I looked like a real girl and a pretty one at that. Yet, I was still so nervous that my legs were shaking.
"I have a confession to make, "he offered shyly. "I dress up and try my best to look like a real girl, too, but I could never look as good as you do." "What are you talking about? You look like a girl even when you're trying to look like a guy." "Well, I've never tried to completely transform myself. I have brothers and sisters at home, so there's not much privacy." "Would you like to try it now, Devin?" "You'll help me?" "Of course I'll help you, silly. Come with me," I said, making my way to the bathroom off my bedroom. I turned on the bath and told Devin to take off his clothes.
"Oh my God. You're going to see me naked."
"Don't worry about it, hon. If it'll make you feel more comfortable, I'll get naked, too. We've both seen other guys naked in the locker rooms, right?" "Yeah, but not each other." "Are you beginning to have second thoughts?" "Yes, I am. So we'd better get on with this before I change my mind."
I bubbled the bath water and only glanced at Devin now and then as not to make him more nervous than he already was. I saw that there was no hair on his flat, hard chest and his precisely rounded nipples and areole were the prettiest shades of pink. His tiny waist tapered down to an enticingly wide set of hips. Although his penis was flaccid, it was longer and thicker than I'd imagined it would be, with a heavily-veined shaft and a bulbous, smooth-fleshed crown. His legs were well-toned and long, ending in a trim set of narrow, dainty feet with the most adorable long pretty toes. I was dying to see Devin's sizeable cock completely hard and I could feel his eyes on me as I peeled myself out of my dress, slipped out of my heels and paused for a few moments for effect before pulling my pantyhose down to expose my erect cock, which danced up and down lewdly once freed from its silky constraints.
When I was completely nude, Devin was too shy to really look at me directly. However, his cock was as hard as a roll of quarters, standing out from his loins and up toward his belly button as he stepped into the bathtub. Neither of us commented on one another's naked bodies and Devin just smiled innocently as he sank into the steaming water.
I bathed him first with a soft cloth, then a loofah from the side of the tub. The tension was thick enough to cut with a knife and I broke it by jumping inside the tub with him and playfully splashing him with the bubbly water. He splashed back at me and we broke into a water fight, the two of us giggling and thrashing about like a wildly competitive pair of schoolgirls. The bathroom floor was soaked with water by the time we calmed down.
We got out of the tub and threw a few large, fluffy white towels on the floor, then entered my bedroom, our naked cocks bobbing this way and that respectively. Devin couldn't seem to pry his eyes away from mine at first, then looked lower down my body.
"You must be proud to have such a big one, he said." "I don't really think about it, "I responded. I really haven't had much use for it yet." "You will soon I think."
As soon as I tried to search for Devin's eyes, he looked away, his shyness driving me crazy with desire.
"Oh, really? Ya think so?" I asked, moving toward him until we were close enough to be kissing. Devin froze and stared into my eyes. As badly as I wanted to touch him, I wouldn't risk scaring him off and held myself back.
"Have a seat on the bed while I get you something to put on, " I said, struggling to regain my composure.
Inside my closet, I found a pair of one of my most feminine, strappy high-heeled sandals from Via Spiga for Devin to try on. When he slid his feet into them, I fastened the delicate straps around his tiny ankles and had him stand up in them. The height of the heels strained his calves tautly, stretching his long firm thighs and elongating the symmetrical orbs of his plump, protuberant ass. Looking downward, he said, "I love the way they make me look, but I don't know if Ill be able to walk in them."
"It'll take some practice, " I admitted. "No one's born knowing how to walk in high heels."
I put on an equally tall pair of heels to guide him around the house until he learned how to move about with a sexy little sway. Then we spent the next hour or so changing in and out of various sexy outfits, doing each others hair and makeup and posing before the mirror together. At one point, I just couldn't seem to stop staring at Devin and began to think of him as her.
She, Devin, was wearing an ensemble of mine of black lace, including a waist cinch that laced up the back with four ribbons to hold up the stockings and matching thong which barely encased her cock and balls. The underwire bra created the illusion of a sexy, feminine cleavage and her pretty pink nipples peeked through the lace. Her narrow, pedicured feet were arched upward in black patent leather mules with tapering five inch heels. All I had on was a lacy white LaPerla bra and panty set to show off my brown skin and a pair of five inch tall clear lucite platforms from Frederick's of Hollywood. Devin had seen me in a variety of sexy outfits from my collection by now, but this one seemed to intrigue her more than anything else I'd worn. She became unusually quiet and somber and instead of looking at our reflections in the mirror, we found ourselves silently staring each other up and down. The next thing I knew, I found myself staring into her cool blue eyes that sparkled as if made out of crystal. I was in a daze when she leaned forward and planted a gentle kiss on my lips and then pulled back with her eyes full of question. She stepped away and brushed back a lock of hair that had slipped across her sweet, tender face." I shouldn't have done that", she whispered. "I'm sorry."
I reached out to her and pulled her against me gently. Her body was intensely hot and her heart was beating rapidly as I held her close. I moved a finger to trace the outline of her strawberry lips and she opened her mouth slightly with her eyes shut to allow my finger to slip inside and feel the wet heat of it. I leaned forward to kiss her soft cheek and said, "Don't be sorry. I'm not. "
I then pressed my lips to hers and the passion of our kiss rose to sensuous heights that left us both gasping for breath. I opened the front clasp of my brassiere and slid out of it. Devin's eyes, which so often found it easier to look away during intense moments were burning into mine as I continued to undress.
Gazing down at my bare chest, she used one of her pretty manicured fingers to run small circles around one of my jet black nipples and areola and then the other. They responded quickly to her touch, erecting fully as she kissed my neck and earlobes.
"I love your complexion," she purred. It reminds me of caramel."
My cock was straining against the snugness of my panties and I felt a strong sense of relief when I worked them downward to let it spring out into the open air. I clasped the base tightly to pronounce the thick veins bulging around the shaft, extending its normal length.
"Oh God, hon. I'm so hard for you," I breathed.
"I did that to you? " she asked innocently.
"Mmmm, yes," I gasped. "I've never been so turned on before."
"Can I touch it?" she asked.
I was dizzy from the wave of excitement that surged through me when she asked that. "Go right ahead. "It's all yours."
For the first time in my life, I felt another person's hand on my sex. She caressed my cock gently and clear streams of pre-come began to flow from its tip. "You can squeeze it harder if you want to," I offered and she did.
"This is so strange, "she said, staring mesmerized at my cock as she stroked its hard length. "I've never touched another penis before. In fact, I never even thought I would."
"Is this a problem for you, Devin?" "Well, yes, sort of. I cant believe we're doing this," she replied. "But at the same time, I know that I love it."
She kissed my lips again while firmly stroking my stiff cock. When our kiss broke, I moaned, "Oh, that feels so good, honey. Amazing."
"I could make it feel better if you want." "How so?" "I could sort of lick it a bit." "Would you really do that for me?" "You have no idea how much I'd do for you."
I pushed my panties down to my ankles and stepped out of them. Then I sat down on the bed with my high-heeled feet spread widely apart on the floor, my cock throbbing in an erotic dance between my open thighs. Devin sank to her knees and slipped between my legs to take me inside her mouth, gently licking just below the head of my staff, the most sensitive area. Then she went about giving me a full-fledged blow job. I savored every delicious detail of her going down on me; the softness of her hair on my thighs, the way she stared up at me, her soft hands gently caressing my smooth-shaven balls, the contrast of our skin tones.
"Am I doing this right? " she asked between her downward sweeping oral caresses. "You've got to be kidding," I whimpered, lying back on the bed. "Can't you tell?"
Every now and then, she'd pause to stare at my swollen cock, firmly stroking the shaft, her eyes glazed as my prick filled her field of vision. The peaches and cream complexion of her pretty face made my cock seem to appear darker than ever. She began licking me everywhere, from the base of my scrotum, across my ball-sack, and even at the aperture of my anal opening. She worked her tongue up along the underside of my shaft and teased my cock head with feather-like flicks and hot breath, then began sucking me in earnest, her head moving rapidly up and down, her talented mouth sending me racing toward orgasm.
Her lips reached further down my shaft as she worked one of her long, slender fingers inside my ass, sending me completely over the edge. At the moment of my climax, she pumped my shaft in her fist furiously, aiming the head directly at her face. Then began the maddening rapture of orgasmic contractions; great torrents of hot white seed racing from the tip of my spasming cock. The look on her face was one of pure amazement as my thick white come splashed against her lips, nose and chin. She gave me an erotic little surprise by scooping up my come as it rolled down her face and licking it up as if it were frosting on a spatula.
As I kept spending, she closed her mouth around me and stared up at me lustfully until I was completely finished. As I lay there, gasping for breath, she rose to her feet, the alabaster column of her cock completely stiff, the bulbous head engorged in an angry shade of red. I grasped her hot staff and playfully pulled her onto the bed next to me. I took each side of her beautiful face and kissed her deeply. We began rubbing our bodies together and I was hard again in no time flat. I reached down and impulsively slipped one of my fingers inside her virgin ass.
"Oh, God, I've been waiting for you to do that for so long, "she gasped. "Work it in and out of me, please."
Her cock was oozing copious amounts of pre-come and when I suggested taking her ass with my cock, she responded with a bashful admission that shed fantasized about it, but had been too embarrassed to ask for it. Her eyes were luminous, her lips trembling as she breathed, "I want your cock inside me now. I want it."
I thought about how lucky I was that my room was far down the hall from my parent's master bedroom and that they never just barged in on me by surprise. I think that Devin was so excited, she never thought to ask about it. As I reached into my nightstand drawer to find a small bottle of vaseline to lubricate my erection with, she perched herself on her hands and knees on the bed, raising her sexy little bottom high in the air. In the dim light, her ass looked so inviting, the shadows making its soft curves even more alluring. She reached back and spread her ass cheeks widely apart for me, displaying her tiny, wrinkled rosebud. I moved behind her with a trembling fist clasped tightly around the base of my throbbing hard on. She looked back at my swollen cock and a worried look came to her face.
"I'm not going to hurt you, Devin," I whispered. She smiled back at me with a renewed sense of calm and assurance, a lock of hair dangling across her face prettily. "I'm not going to lie to you, though. Actually it might hurt at first."
"I know, but I think I'm ready."
I guided the head of my cock to her tiny rosette and pushed forward. It took several moments of patient care and a bit of lubricant before I managed to sink the entire length of my shaft inside. "If it hurts, let me know and I'll stop."
With my hands firmly grasping Devin's hips, I began to move in and out of her with measured strokes, establishing a steady rhythm.
"Oh, God, I'm getting fucked! "she cried out, not in disbelief but in emphasis. I hadn't imagined that she'd take to my penetration so quickly and with such unbridled enthusiasm. The inner muscles of her ass tightened around my pumping cock periodically, stretching my member out to its full length, drawing on it like a hot, hungry mouth. I reached beneath her and grasped her cock, which was every bit as hard as my own. As I shoved myself in and out of her, manipulating her erection in time with my thrusts, her cock felt like almost an extension of my own.
As much as I enjoyed taking Devin from behind, I had a sudden urge to have her lying beneath me on her back. I withdrew my cock just long enough for her to turn over. She spread her long, coltish legs high in the air in an abandoned offering of her tender opening. She let out a sharp gasp as I sank the head inside of her again. then she smiled up at me lustfully and began breathing heavily. Very slowly, I worked my way further, deeper inside her.
"Oh, yes," she panted. "Give me all of your cock, please." I probed inside balls deep, feeling her vise-like anal ring squeezing to keep the head of my tool from slipping from her tight orifice. As I fucked her faster and faster, with all the strength and endurance my body could muster, she yelped, shuddered and broke into a frenzy, bucking up against me. She wrapped her arms around my tightly and gasped, "Oh, God. I'm gonna come."
Her cock erupted untouched, blasting a cascading offering of creamy white spurts that splattered across my stomach. Her ass muscles spasmed harder than before throughout her intense orgasm. I was soon about to experience for the first time the moment of exquisite bliss that accompanies release inside a hot tight ass. When I was unable to hold back any longer, I wrapped my arms tightly around her frame and came with a sharp cry and a series of violent shudders.
"I can feel you coming in me, Caramel, "she moaned. "Oh, I love this," she mewled as I collapsed on top of her spent, sweaty form. Both of us completely exhausted, we cuddled quietly and drifted off into a deep slumber. The last thing I remember thinking about was that she'd given me a new name I might use for the rest of my life. That was pretty special to me.
Devin and I continued to meet as often as possible but after graduation, it was time to get ready for college and neither of us would be attending school near one another. I was to attend Northeastern University in Boston MA and she was off to Louisiana State University. We stayed in touch by phone, snail mail and email but it wasn't quite the same. What made things the most difficult was that we had no privacy at our dorms, not even for chat online much. We both had room mates to deal with and it always seemed that once one of us were free, the other was busy.
We looked forward to meeting during the holidays until her parents dropped the bomb that they were moving to Florida for an early retirement. Once it became obvious that it might be years before we got together again, we promised to stay in touch, and kept our hopes up about being together again and possibly exploring a long term relationship one out of college. For the next four years, we never stopped writing love letters to one another.
If you've enjoyed this story, email me at caramel@tsdreamland.com