2008-Mar-30 - Part 1 - Transvestites and Old Friends
Tags: Straight, BDSM This is the story of my life. Or at least my sexual life. Over the next few weeks or months (depending on how involved I get), I'm going to tell all of you how I went from being a shy, somewhat geeky guy, to the confident, sexual being I am now. Before we begin, I feel the need for a small disclaimer: These stories will be genre-spanning. I'm bisexual, and a great deal of my sexual awakening has to do with BDSM. As such, there will be straight stories, gay stories, BDSM stories, and everything in between. Also, flashbacks will be italicized for clarity.
I'll begin by describing myself as I am now. At the time of my writing this, I'm 25 years old. I won't be telling you my name, because all of this is true. Instead I will insert *** in place of my name. Also, all the other names have been changed. I stand about 5' tall, which used to be a sore spot for me in my life, although I've gotten over it now. Most women want a man to be tall and powerful, and although I have a very athletic and well-muscled body, I definitely don't meet the 'tall, dark, and handsome' stereotype. I have short, sandy-blonde hair, always slicked back, and combed and parted quite elegantly in the older French style. I have different coloured eyes, the left a piercing blue-grey, and the right a rather striking emerald green shot through with flecks of gold. I'm recently become quite successful, professionally, and I tend to dress accordingly. I favor tailored suits of white or black, usually choosing unified accents of silver, gold, or the opposing shade. I have been told on several occasions that I smile like the Morningstar himself. I also have a beautiful, thick 8" cock, which, because of my height, has surprised everyone who has ever seen it.
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On that day, as I remember it, I had never before felt so confident, so sure of myself. I was infused with my newfound sexuality, and, despite the pain that I had endured to reach that point, I knew that it had been worth it.
I live in Vancouver, and I was on the Skytrain, heading from my house towards my destination. I wanted to have a particular effect that day, so I was dressed completely in white. Shoes, suit, belt, tie, watch, everything. Pure white. Since my sexual awakening, transit has become one of my favorite methods of traveling. I often stand, gazing at the people around me, wondering about their kinks, their fantasies, and invent fantasies of my own about them. On this particular day, something happened that was rather annoying, but also eventually led to an encounter which I will be describing to you sometime later.
I was in my usual spot, standing near the doors, when a woman boarded the near empty train car. She was a he, actually, a transvestite, and stood about 6' tall, with long blonde hair. I noticed right away that she had big, powerful hands, although they were quite soft looking, with long, beautifully manicured nails. She was well dressed, with sexy 'fuck-me' boots complementing her outfit, and, despite her obviously male nature, all in all she was quite pretty. She sat facing me, crossed her legs, and proceeded to read her newspaper.
A couple of stops later, a young couple came on board. By this time the train had filled almost to capacity, and the only seat left available was next to the woman reading her newspaper. The young man sat down beside her, inviting the girl to sit on his lap, which she did. As she sat, our eyes met briefly and I smiled. She was exceptionally pretty, with long, wavy, chestnut brown hair, lovely green eyes, and full lips that curled up on either side, as if in slight, perpetual amusement. She quickly looked away but, as the train moved on from the corner of my eye I saw her glance back towards me a few times. At some point I noticed that the young man had realized he was sitting next to a transvestite, and was now staring openly, running his eyes over her body and face in what I can only describe as amused disgust. The woman had noticed as well, and was obviously becoming uncomfortable with this boy's rudeness. I leaned towards the woman slightly, putting my head partly in the guy's vision.
"Didn't your mother ever tell you it's rude to stare at a lady?" I asked, looking him straight in the eye.
His eyes snapped up, his face instantly going red. "Wh... what?"
"You're being very rude, and you're obviously making the lady uncomfortable." I held his furtive gaze with my own rock-steady stare. "How would you feel if I were to stare at her like that?" Without looking, I pointed to his girlfriend, who was now fidgeting uncomfortably on his lap.
By now the woman had realized that I was coming to her rescue, and had a small, knowing smile on her lips. I could feel her eyes on me, but I kept my gaze locked on the young man. He was about my age I guessed, maybe a year or two younger, but he obviously had the emotional maturity of a 12-year-old. At the mention of his own girlfriend being treated in such a poor fashion, he immediately became defensive.
"You'd better not be looking at her at all." He said menacingly.
"That's right, I'd better not. And you'd better remember The Golden Rule."
The train stopped on a busy platform, and the woman, who had remained silent up until now, spoke for the first time. "Excuse me. This is my stop." The young man moved his legs sharply out of the way, jostling his girlfriend, who through all of this had had the decency to look suitably embarrassed, from his lap. I offered my hand to the woman, which she took it with a smile, and she stood up, head and shoulders taller than me. I kissed her hand.
"My knight in shining armour." She said coyly. She bent down, kissed me lightly on the cheek, and then was gone. The train started to move again.
The next stop was mine, so I decided to take this a step further. I took one of my special cards, the ones not for business, out of my inner breast pocket.
"All good deeds deserve to be returned." I said, looking the young woman, now sitting beside her boyfriend, straight in the eye as I handed her the card. "Give me a call when you realize you're too good to waste your time with a small-minded bigot." The boyfriend's face darkened angrily. I stepped off the train onto the platform, noticing from the corner of my eye that she was turning the card over in her hands. I smiled, both from the young man's angry words as I walked away, and from knowing what the card said.
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"Anything. Anytime." The hot wax dripped from the candle, splashing painfully across my left nipple. "Do you understand?"
I tried to speak, but couldn't form the words through my ragged gasping for air.
"I asked you a question!"
Jenna rarely raised her voice, but it often became heated with the edge of her anger, and so it was now.
"Y...Yes." I managed.
"What did you just say?" Her voice became dangerously low, and I immediately knew the mistake I had made.
"Yes, mistress!" She dripped more of the melted candle, this time onto my right nipple, and I gasped in pain as it burned, then dried and hardened. Despite my pain, I was rock-hard, kept that way by the combination of the vibrating cock-ring at the base of my shaft, and the not-so-gentle ministrations of Jenna's free hand. I had been in this position for some time now, and the entire head of my engorged penis was covered in pre-cum. I was strapped to a table propped at a 45 degree angle to the floor, my wrists and ankles bound to the corners with leather shackles.
"I'm not sure I believe you. Explain it to me." I kept my eyes downcast, but in my peripheral vision, I could see by the concerned look on her face that this was important to her.
I took a moment to collect myself. "In order to truly submit, I must be prepared for anything at any time. I must be willing to accept that I have no choice in the things that may happen to me, and I must be able to endure them, whether I understand them or not."
I couldn't see her face clearly, but from the tone of her voice I could tell she was disappointed. "Such a surface understanding." Her voice hardened once again. "Oh well. This is just the first of many lessons to come. I expect you to do better in the future, but I think you need more examples before you can truly begin to understand what it means to give yourself completely to another person."
I was upset that I had displeased her, but her hand stroking my thick shaft kept me as hard as ever. She bit my left nipple, hard enough to leave small white teeth marks in the soft flesh, and I gasped at the shocking combination of pain and pleasure. She held the hard nub in her teeth, flicking it back and forth with her tongue. She began pumping my cock faster, and I could feel my orgasm start to build. Suddenly, she let go, then impaled herself on me, moaning loudly as I stretched open her hot, tight pussy.
"Look at me." She commanded, gripping my chin with her free hand. The other held the still lit candle. I looked up into her eyes. She held my gaze momentarily as she fucked herself on me, then bent her head down to kiss me. As her tongue snaked into my mouth, her hand moved from my chin to the back of my head, gripped my hair, then painfully pulled my head back, holding my lower lip in her teeth so that it stretched out to meet her. She held herself as deeply onto me as she could, grinding her swollen clit onto the vibrating ring at the base of my rod.
Jenna rode my cock harder, slamming herself onto me so hard I thought the table would break at any moment. "Don't you dare cum until I tell you to." She said, after she had mercifully let my lip go. Her tone and glare seemed to say, "You wouldn't want to disappoint me twice in one day, would you?" I certainly didn't want to. At that moment I wanted nothing more than please her, and so I redoubled my mental control. Jenna gasped, and her eyes rolled back in her head as my cock flexed deep inside her, growing in thickness, momentarily spreading her even wider. I felt a fresh surge of her hot juices coat my already soaked tool.
She drove herself onto me frantically a few more times, her large tits bouncing in my face, then groaned as her orgasm started to peak. "Cum now." It was an order, and I was in no position to refuse. I abandoned myself to the sensation of being sheathed in her hot, dripping wet pussy. She still came before I did, her entire body quivering with release as her insides clenched down on me, but she continued to drive herself down onto my cock until I, too, found release, flooding her insides with my hot cum. My moan of pleasured release turned into a scream of agony as she planted the still lit candle, flame down, on my nipple, extinguishing it there. My mind reeled, the pleasure in my cock mingling with the flare of pain in my chest, and, just before I passed out, I heard her say once more: "Anything. Anytime." She kissed my throbbing nipple, and then the darkness took me.
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As I neared my destination, I put the events from the train out of my mind. Stopping briefly to check my appearance in the reflection of a glass storefront, I mentally collected myself, organizing my thoughts for what I was about to do.
I arrived at the building and knocked on the front door. I didn't notice at the time, but when I thought back on it afterwards, I realized that I had not been at all nervous. A muffled voice came from the loft.
"Who is it?"
"It's ***." I called back.
"***? It's open, come on up!"
I made my way up the ladder/stairs to the second floor as she spoke again.
"Sorry, I'm just in the middle of making dinner." I stood facing her with my hands in my pockets, her back to me as she faced the stove. "I'm so glad you stopped by, it's been too long since we hung out." I took a moment to savor the sight of her before she turned around. Valentina is my height, and Chilean, with flawless, nut brown skin. She is a seemingly impossible combination of cute and sexy, with a smile that ranges from pixie-like to downright impish. I let my eyes roam down the straight, black A-Line of her hair, down her back, lingering momentarily on the impression of her bra-strap visible underneath her tight, 3/4-length t-shirt. Her form-fitting jeans only served to intensify her firm, well-proportioned ass, and she had them rolled up slightly to expose her bare feet and well-formed calves.
She wiped her hands on a cloth that was over her shoulder as she turned from her work, and her jaw dropped as she looked at me for the first time.
"Hi, Val. I'm glad to see you too." I said casually.
"***, you look amazing..." She breathed, her eyes wide.
I smiled slightly, looking down from her eyes momentarily in false modesty. "Thanks. I'm glad you think so." She regained a measure of her composure and smiled coyly.
"What are you all dressed up for?", she teased. "You got a hot date tonight?"
I chuckled softly, meeting her gaze once again. "Something like that."
"Well do you at least have time for dinner before you go?" She gestured behind her. "I spent all day making pastel de choclo and alfajor."
Val is a fantastic cook, and my stomach grumbled in mouth-watering anticipation, but I played it off.
"That sounds amazing. But I actually came here for something specific. Maybe we'll have time for dinner after that."
An expression of curiosity crossed her features. "OK, but you're missing out." She waggled a wooden spatula at me, then turned back to the stove-top. "I just need to finish this last one off."
"No problem," I said. "We can talk while you're cooking." I moved past the kitchen and into the living room.
"What's on your mind?" She called over her shoulder, head bent to her task.
I paused for a moment before answering. This was my last chance to reconsider. After this, there would be no turning back. I felt tingles of excitement shoot up the back of my neck. I knew there was no way I wasn't going to go through with it.
"Val, how long have we known each other?" I knew the answer, but I wanted her to tell me so that we would be on the same page.
"Ummm... About 8 years I guess? Why?"
I smiled at the memory of our meeting for the first time. "And how long have we been friends?"
She laughed liltingly, and my heart sang at the sound. "About 8 years I guess." I heard the stove and hood fan click off, and then the sound of dishes being pilled in the sink. She came into the living room, once again wiping her hands on the towel. My breathing quickened slightly at the sight of her, her skin shining with a slight sheen of sweat. I looked her straight in the eye, mentally pulling her to me.
"And how long have I been in love with you?" I asked softly.
She froze, clearly not expecting this. "***, we've been over this..."
"How long?" I asked. Softly again, but more insistently this time.
She looked away. "About 8 years." She mumbled.
I called her name in a firm voice. "Look at me." She looked up shyly, clearly not wanting to meet my gaze, or to have this conversation again as we had before. "Look at me," I said again. "But not through the refraction of 8 years. Look at me as I am now, standing here before you, and try to remember the reasons you've never returned my affections."
Her face clouded, as if in mental turmoil, but she did as I asked. After a moment, I thought I saw some flicker of recognition in her eyes, and her features softened slightly. I knew that now was the crucial moment, and I stepped forward quickly, fluidly, until we were standing mere inches apart. She was confused now, having had no time to assimilate or understand what she was feeling. I lifted her chin with one crooked finger, and gazed into her eyes for a moment.
"***, I..." And then I kissed her.
At first she stood stock still, unsure of what to do with her conflicting emotions. But when my tongue parted her soft, full lips she moaned sharply, and then melted into my arms. I drew her closer, and she met my kiss with equal passion. One advantage of having been close friends with this girl for so long is that I had been privy to all the details of her sexual experience, and I knew exactly what turned her on. I pulled her upper lip into my mouth, running my tongue along the underside of it, and she moaned again, more insistently this time.
As suddenly as I had started it, I pulled away. She stood, breathing heavily, her eyes still closed, with her fingertips resting on my chest. When she opened her eyes, I was smiling at her, and she smiled back in surprised amusement.
"Wow. I... I'm not quite sure what to say. I never expected that."
"I did." She chuckled softly, knowing exactly what I meant. My expression became more serious. "But there's only one thing you need to worry about saying."
Her gaze became questioning. "What's that?"
"Stop."
"I don't understand."
"In a moment I'm going to kiss you again. From that point on, the only thing you need to worry about is whether or not you want me to stop."
I was sure she could see the fire in my eyes, and, since I could feel her full, firm breasts pressed up against my chest as she breathed deeply, I was equally sure she could feel the firmness of my resolve pressing into her thigh. She flushed darkly, and I saw lust spark in her eyes.
She considered for only the briefest of moments. "'Stop' is the last thing I'm going to be saying at this point." She put her hands behind my head and pulled me in for another passionate kiss. I could feel her need igniting in the heat of that kiss, and I returned it in kind. I felt her hands on my chest, undoing the buttons on my jacket, and then she pushed it from my shoulders. I held her close as she pulled my tie loose, my lips moving from her mouth to her neck, trailing soft kisses down into the hollow of her throat. When she started unbuttoning my shirt, I intensified my kisses, using a combination of sucking and long strokes of my tongue on the soft, sensitive flesh below her jaw and above her collarbone. She groaned encouragingly, and my shirt fell to the floor.
I stood, naked to the waist, then suddenly bent down and swept her up into my powerful arms, lifting her from the floor in a sitting position. She squealed with delight as she wrapped her arms around my neck and started kissing me again. Making my way mostly by feel, I managed to get to the bedroom without bashing into anything along the way. My knees hit the bed and I stopped, locked in our passionate embrace. After a moment I sat Val gently on the bed, her legs wide apart with my knees between them. I bent down to continue our kiss, and let my hands move from her face down her body. I caressed her neck, trailed my fingers teasingly over her breasts, and felt, more than heard, her moan into my hungry mouth. I drew her tight top up slightly, tracing the line of her jeans with one fingernail. She gasped sharply as my light touch tickled the line of muscle leading down into her waistband. She lifted her arms above her head, and I indulgently pulled the concealing garment off. I stood back a little to admire her beautiful form. She smiled, as impishly as I had ever seen, as she ran her fingernails down my chest and hard abdomen to my belt, which she started to undo. I grabbed both of her wrists, twisting her arms behind her back, though not painfully, and held them both there with one hand.
"Not yet, little one." I chided lightly, wagging one finger at her.
She pouted in mock protest, but I saw light shining in her eyes and I knew she was enjoying this as much as I was. With my free hand I lifted her chin into another kiss, and as our tongues explored each other's mouths I used my free hand to undo the clasp of her bra.
"Lay down." I said in a soft, firm voice, and as she did so I released my grip on her wrists, sliding my fingers teasingly along her arms, bringing the lacy straps of her bra with them as I did. She lay there, flawless, her flesh flushed darkly with her desire. Her bra was sitting atop her breasts, barely covering the two heaving mounds of soft flesh. I longed to remove it, to take her breasts in my mouth, but I delayed a little longer, instead stretching my body out along hers, supporting myself on my hands, with one knee pressed firmly between her soft thighs. I could feel the heat radiating from her crotch. I took her wrists again, this time moving them above her head, and pressed them both to the mattress, one held with each of my hands. I kissed her mouth, her neck, her collarbone, traced a line between her breasts with my tongue, and nipped playfully at the sensitive flesh over her ribs. Her eyes were closed as she lost herself in the sensations, and I smiled that devilish smile of mine, knowing that I was about to make her feel even better. Kissing the tops of her breasts, I then lightly bit at her nipples through the fabric of her bra. She gasped sharply, and I knew it was time to take things a little further.
Still holding her arms firmly above her head, I took the bra in my teeth and flung it away sharply. Val's eyes flew open, and I took her in another kiss, more roughly this time. I put my other knee between her thighs, spreading her legs around my hips, and leaned down over her body. Her flesh burned against mine, and I could feel against my chest that her nipples were becoming hard. I tilted my hips, pressing my bulging sex against the heat between her legs. I groaned in pleasure at the sensation and Val gasped into my open mouth. I took the opportunity to kiss her more deeply than I had yet, massaging her tongue with my own.
Switching my grip on her wrists so that I had one free hand, I reached down and lightly stroked my fingertips across her breasts, savoring the sharp intake of her breath every time the rough tips passed over her hardening nipples. Without warning, I took one of the small nubs between my thumb and forefinger and pinched. I removed my mouth from hers in time to hear her gasp, and then clamped it down over her other breast, sucking in both the nipple and the entire areola. She moaned deeply, delighting in the mixed sensations of pain and pleasure. I continued to suck on her firm tit, alternating between flicking my tongue across the nipple and giving it long, sweeping stokes. Val continued to moan, and her breathing became heavier and faster. After a minute of this, I stopped pinching and started massaging, kneading the entire breast in my hand, feeling the firm flesh respond and heat under my touch. I switched positions with my hand and mouth, giving each breast equal attention, bringing Val deeper into her pleasure.
"Oh fuck, I want you inside me right now." She groaned.
I moved my mouth from her breast to her lips, brushed them softly with my own, feeling the heat of her breath. "Soon. I promise."
Suddenly Val moved with surprising speed, and despite my greater strength I was caught off guard. She twisted out of my grasp and used the momentum to throw herself on top of me, her small hands pinning my wrists. With my legs dangling off the edge of the bed, my position of power was significantly compromised. She looked down at me, a smile playing at the corner of her soft lips. "You don't get to be the only one who makes promises."
I smiled back, and responded with only partial sarcasm. "Yes, mistress."
Val looked momentarily confused, trying to decided whether or not I was making fun of her, and then decided it didn't matter. "Mistress, is it? All right then. Put your arms out to the sides, palms flat against the bed."
I knew from experience that I would enjoy this new game, so I complied without comment when she relinquished her grip on me. It hurt a little in my shoulders, to turn my arms so far forward, but I embraced the pain, letting it wash over me to become part of the overall sensation. Thus crucified, I awaited further instruction.
Val sat straddling my crotch, her bare upper body fully revealed to me as she edged back slightly, until she was sitting on my knees, at the edge of the bed. Her nails raked lightly down my chest, flicked teasingly over my nipples, and I gasped with a sharp intake of breath. My nipples have always been extremely sensitive, and even this light touch was enough to make me squirm. Val seemed not to notice my discomfort as her hands glided further towards her destination. Her fingers found my belt buckle and deftly undid it in one motion. She suddenly stood up, catching the waistband of my trousers as she did, and pulled them and my underpants down and off. My fully erect cock sprang up, a willing testament to my arousal.
Val froze, her eyes drawn reflexively to my member. "Wow..." She knelt down between my knees, and tentatively reached out to touch me. "OK," She said, in a remarkably candid voice. "I was not expecting that."
I smiled down at her. "No one ever does. But I don't mind, really. It's my secret weapon."
She was still softly gripping my shaft, and now she started to stroke it a little, experimentally, pulling the foreskin down to expose the fat, engorged head, glistening with pre-cum. "Yeah..." She breathed. She blinked, regaining her composure, and smiled mischievously at me. "Some secret."
"Sweetheart, I've been trying to reveal this one to you for years."
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Her face clouded momentarily, and I though I had ruined the moment. "I guess I'll just have to make up for lost time then." I was glad to be wrong.
I started to say something, witty to be sure, but the words flew from my mind when I felt her hot, small mouth clamp around the head of my cock, her full, moist lips sliding smoothly along the shaft. "Oh fuck me..." I moaned, stretching exquisitely, feeling her with every muscle in my body as I arched my back, urging her to take me deeper, into her throat. She pulled back, and I groaned.
"Soon." She parroted me mockingly. "I promise." I laughed at the sweet, ironic torture, and then forgot myself completely as I felt her wet warmth envelop me again. Enough talk, I though, and lay my head back, closing my eyes. Val worked me over expertly, alternating deep sucking and stroking, with jerking me while taking my balls in her mouth. I was well on my way when Val said, between long, stroking licks, "I want to taste your cum." I groaned in response, again arching my back and thrusting my hips upwards. This time she responded eagerly, taking me into her throat all the way to the hilt. I moaned again, holding myself there, delighting at the sensation of her muscles contracting tightly around me. Keeping her mouth and throat open as wide as she could, Val began to bob her head up and down, fucking my thick length with her throat. She didn't gag once, and I was inexplicably proud of her.
I could feel my orgasm building, but I wanted Val's first taste of my cum to be perfect. I opened my eyes. "Move back a little. Stay on your knees, and keep my cock in your mouth." She understood immediately and did as I said, placing her hands on my hips to steady herself and control my depth. As she moved, I stood, and we effortlessly shifted so that I was standing, with her kneeling in front of me, my achingly hard penis still buried in her mouth.
"I'm going to fuck you now." I told her. "And I want you to look into my eyes while I fuck your beautiful little mouth." She looked up at me obediently, and I was momentarily stuck by how fluid her concept of dominance and submissiveness was. Combined with the sight of her big, pretty eyes staring up at me, it was almost enough to push me over the edge, but I held back with some effort. I reached down to softly stroke her cheek, not yet moving my hips, then gripped her jaw, on both sides, with one hand, forcing it open by applying subtle pressure. Enough to get the message across, but not to really hurt. Her jaw dropped, and she repositioned her head slightly to allow me a straight line into her awaiting throat, her eyes never leaving mine. I started to fuck her then, slowly at first, pulling fully out, then gliding all the way in, holding myself as deep as I could, savoring her tightness. As I continued like this, my need grew until I couldn't control it anymore. I started to fuck Val's mouth faster, harder, and I interlaced my fingers behind the nape of her neck to control my stokes. Usually I'm known for my stamina, but I'm not ashamed to say that in this situation I came rather quickly, after only a minute or two. My cock stroking continuously into her, there were tears running from the sides of Val's eyes, and to this day I can't say whether they were from pain or pleasure. Probably both.
"I'm going to come now." I said, and Val groaned, clearly eager. I released the back of her neck and ran my fingers through her hair, holding her head but loosely, stroked shallowly into her soft, hot mouth a few more times, and then every muscle in my body tightened, I stopped moving completely, and then the world, and I, exploded. I arched my back and closed my eyes as hot, thick spurts of cum shot from me, hitting the back of Val's throat, filling her mouth completely. She swallowed it down eagerly, not spilling a drop. As I started to come down, she moved her hands from my hips so they could help her milk the last drops of sticky fluid from my softening member, sucking heavily. I jerked, the sensation so pleasurable it was dangerously close to pain. I looked down at her and smiled a tired, satisfied smile.
Val pulled back, still holding my flaccid penis in one hand. "Mmmmm..." She licked her top lip with her tongue, and then frowned in a mock pout. "And here I was hoping to get properly fucked. After an 8-year build up it's the least you could do."
I laughed and helped her stand, then kissed her softly. "Who said anything about being finished?"
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