An intense BDSM, gay sex story...
"Evannah Cupcake: A Fantasy in Drag," erotica by V.C.
I am thirty-two; I have a beautiful wife and a darling baby girl. We live in New Jersey in the suburbs with the white picket fence and a dog. We are the American ideal of what a family could and should be: Perfect. Wholesome. Pure. Happy. Admired. Respected. Successful. Loved.
I have a confession.
I've been cheating on my wife and my family, with a boy in drag. Do I have any regrets, any shame, remorse? I absolutely do not. I have always had a thing for androgynous men, transsexual females, she-males, and drag queens. I love them all, even more than I love women. They are mysterious. Elusive. Rare. Captivating. I knew I’d risk anything just to get my hands on one. And I did. It’s not that I have issues or that I am a closeted bisexual man either. I love women, but I love androgynous men more. I had oppressed it for so many years. Now, I have no shame. I love cock more than I love pussy. I come at the sight of watching a man enter his massive cock into another man’s rectum. I harden whenever I encounter a steamy-hot trans-female in the subway, and I quake at the knees whenever I go to a drag show. I am seduced by their illusion of femininity, over-the-top glamour, and overt sexuality. Part of the reason why I decided to work in New York is because the city is full of these marvelous creatures of taboo.
Marissa by Matthew Stradling, available at ObessionArt.com
I met him in a café in Manhattan, a café that was ironically called Taboo.
I had just gotten off work, and was enjoying a cup of espresso. He was sitting in a table across from me, cross legged, reading a magazine. He was strikingly gorgeous: slim legs, covered by fishnet stockings. He wore stiletto heels, a little black dress with polka dots, vintage-like, a long black wig that caressed his shoulders, succulent red-hot lips, stunning bluish grey eyes of the rarest kind, and a lovely pale face that was dolled up with black eye-shadow, mascara and face powder. His body was slim and petite, slightly muscular at the arms, toned at the legs, he maintained his figure well. His chest was padded, so to give off the illusion that he had 32C breasts. His backside wasn’t padded though, I could tell: it was perhaps the only real feminine feature he had on his body; it was beautifully round and juicy, like that of a real woman. If it weren’t for his prominent Adam’s apple, one would think he was a woman, albeit a slightly masculine one. I couldn’t keep my eyes off of his presence.
I was reluctant to walk up to him, afraid of embarrassing myself, but I gathered up the courage to go up to him and whisper, “You are beautiful.”
He looked up at me, in surprise, and smiled.
“Why thank you….what is your name sir?”
“Mark.”
“My name is Evannah, Evannah Cupcake.”
The sound of his voice, slightly deep but with a hint of affected high-pitched femininity, seduced me. I was his.
“Evannah…what a lovely name.”
He giggled adorably. I made him blush. His smile was charming; it said “I am yours.” We sat together to enjoy our coffee, and we talked as if we were close friends, even though we were perfect strangers. We met at that café quite often after that. Sometimes in the morning, sometimes in the evening, by accident, it was never planned. It was the perfect escape for me, to get away from my wife, away from the responsibility of being a husband and a father. I was free.
He didn’t always come to the café as Evannah Cupcake. I later found out that his real name was Alexander, and behind his drag persona there was a charming free-spirited, passionate young man who was extremely handsome, slightly serious, and wise beyond his years. Anybody who looked at him could not have guessed that he was gay, let alone that he performed as a drag queen. I admired his courage, envied his bravery. He put his whole academic and professional reputation on the line, and did it with a “Fuck you, it is my world and I am living it.”
He was a twenty-one year old NYU student majoring in business, so as Alexander he often wore a tailored black suit, white shirt, and a red tie with his short and slightly curly black hair slicked back. His overall look was very conservative, perfectly constructed from his head to the glossy black shoes on his feet. He was still stunning to look at, with his regal face. His soft curly black hair brought out the seductiveness of his grayish blue eyes even more so than when he wore a wig and makeup. He was sexy and attractive, young and powerful. It turned me on to him even more, to see this young man transform from a prim and proper business student to a fine, seductive, and jaw-dropping illusion of a woman who embodied class, sass, and confidence. He was a work of art, a fantasy in drag.
I went to his drag performances at the club a couple of nights: he was phenomenal, hilariously funny, an oversexed diva. He had men eating from the palm of his hand, and money falling at his feet. I dreamed of him every night, thought of him when I made love to my wife. I masturbated to the mental image of him seducing me in drag, fucking me in drag, taking me as his man, he as my secret lover. I desperately wanted to have a passionate love affair with him, or even a one-night stand. What I would have given to just suck his dick, even for just a minute, or to caress his balls with the palm of my hand and the flick of my tongue. I waited and fantasized for what felt like forever.
Then came that day when we went out to lunch in Bryant Park. I hinted to him my desires, not for him per se, no, I didn’t have the balls to tell him that, but for my desires in general. He didn’t find them unusual. It gave him a rise: oh God, to see his prominent dick squirm up and down beneath his black pants. He quickly hid his excitement by crossing his legs in the same manner as he did when I first met him as Evannah Cupcake. It gave me a thrill; I covered my timid moan with a cough, and then at last confessed to him that I was married and a family man. He didn’t find that unusual either. It made him giggle; he found it amusing. This didn’t offend me. The sneaky and seductive look in his eyes suggested that he had known my secret all along. And then I told him my age. He was surprised that I looked so young, he said I looked like a younger Richard Gere. Then he declared, “I love older men with a passion.” He said it with such power, such force. His hand touched mine; his eyes coolly gazed at me from head to toe, and then he gave me a kiss on the lips, our tongues danced. His lips tasted and smelled faintly of lipstick; it made me greedy. I wanted to pull his cute little ass onto my lap and gyrate my crotch against his so that I could feel the hardness of his luscious dick and he could feel mine. I was ever so tempted, but then he stopped our lip embrace with a passionate sigh, and gasped, “Fuck…”
“Oh how I would love to fuck you,” I thought, too nervous to say it out loud. I looked around; people were staring at us, it made me awfully self-conscious.
“People are staring,” I said, sounding so stupid and childish.
He looked at me and winked, “Let them stare…”
My dick desired his touch, his wet mouth, his tightly clenched ass. His tongue ran along his smooth and lovely lips; he was hungry for me, salivating for my cock. I breathed slowly. My feet tapped in anticipation. He could sense my nervousness, my hesitation. He knew that he was the first man that I had ever kissed, and the first man that I would fool around with. He took me by the hand and led us to a secluded area in the park, where we were hidden by brush and shadows.
“I really like you Mark,” he smirked.
He rested his hand on my crotch, squeezing on the throbbing bulge. He grabbed me by my tie and led my lips back onto his. I raised my hips against the palm of his hand, gyrating into him as we devoured each other. I felt his hands tugging at my belt, forcing my pants down my thigh. I moaned as he pulled down my zipper, and pulled out my cock from my briefs. His fingers glided along my balls, traced the veins of my bulging member, caressed the shaft, and circled around the head. I could have easily come on his hand, but I wanted desperately to release into his mouth.
Before I knew it, his mouth went from my lips to my cock. He was a fucking good cock sucker, the top of the class, obviously more experienced than I could have ever imagined. His tongue ran laps around every inch of my cock, slowly, and then rapidly, enough to make my head spin. He sucked me like a vacuum, my fucking God, he blew my mind! I raised my hips higher, forcing my cock to go down his throat; he took it instantly, letting my entire member fill him up. I gyrated my hips into him faster and faster; he followed the same rhythm, sliding my cock in and out of his mouth and down his throat in complete unison to my gyration. I couldn’t take it, the sound of him sucking me off, the way his tongue twirled and teased around me, and the feel of his throat squeezing my cock, swallowing it whole—my god! I grabbed him by his baby-soft hair and pushed him down so hard so that his lips pressed against my sweaty pubic hair. My cum gushed down his throat. I panted and gasped as he swallowed every last drop of my semen.
“You are so good at this…” I sighed, releasing him from my cock.
“And there is more to come….” He winked. “Pun-intended.”
His white business shirt was damp and transparent, my mouth craved for his perky little nipples that were protruding through the fabric. I leaned forward to unbutton and expose his smooth chest and his slim sexy stomach, but he pushed me back gently, whispering, “Let’s continue this in my apartment, okay?”
I nodded.
This cannot be happening, I thought, as we took a cab to his apartment. I couldn’t believe that he sucked my dick in public; even my wife wasn’t that risky or daring. I couldn’t believe that I was madly, passionately in lust with a 21-year-old boy, and he with a 32-year-old man. Just the thought of that made me rock-hard again in my trousers; he noticed, and wanked me off in the cab with my pants on, and then he sucked my dick in the elevator with my pants all the way down to my knees. The danger of possibly being caught was a rush for me; he didn’t seem to care, he had obviously gotten away with this behavior many times before.
My knees collapsed once we reached his floor. He grabbed me by the tail of my tie, dominantly, and walked me on my hands and knees to his apartment door as if I was a dog on a leash. He hauled me inside his apartment; it was no poor college boy’s apartment. He was filthy rich, and he had good taste.
He slid off his belt as I shakily tried to get up from the floor. His belt cracked in the air as he whipped it against my back, stinging my flesh through the fabric of my shirt.
“You kinky old man,” he smirked, whipping my back once again, but with more force than before, the sting more prominent. “Get up! Take that shirt off, get comfortable, and treat yourself to some wine in the bar. I’m going to change.”
I got up and grabbed him roughly by his shirt collar, smashing my hand against the crotch of his black pants. I could feel his member throb; he was fucking huge, a skinny boy with a massive dick. Just the way I imagined it. My only thought was to undress him, for me to finally see, touch, and taste his body and his enormous cock, which I had never seen before in its entirety. He bit onto my lip and pulled it with his teeth, growling, “Hold it dirty man….” He thrust me onto his leather couch; I was desperately eager, I didn’t want to take my hands off of him so he strapped my wrists together with his leather belt. He had no other choice; I was too excited, brimming with lust and debauchery. He left me even hornier, the way he dominated me, in total control.
My cock was still exposed, hard and erect, my briefs hanging down to my knees. I closed my eyes, imagining what he was doing, leaving me here all alone. I could hear the sound of makeup falling against a countertop, a sound that I was all too familiar with every morning when my wife was getting ready for work. Then all was silent; he took his time. I breathed slowly, trying to calm my nerves, waiting for the very thing that I expected and wanted, needed more than anything. And then there he was, there she was, Mistress Evannah. I was speechless.
Her hair was long and straight, dark as black ink, falling past her shoulders, and braided to give off the illusion that it was a whip. Her lips were rose red. She wore a skin tight vinyl red dress with a shiny black vinyl waist cincher. Oh, that body, that shape, her arms so toned and muscular, those legs, smooth and slick and hairless, donned with shimmering black stockings. She wore five-inch black platform boots, sharp enough to penetrate through my soul. Her smile was provocative. She carried a bag; I imagined that it was full of tricks and devices and toys. She turned around; the backside of her dominatrix outfit exposed that voluptuous booty, bare naked, I was filled with lust once more.
“Oh my goodness,” I grinned, kicking my head back in disbelief of what I was seeing, of what I was doing, here in this place, in this setting, in Alexander’s world. I did not care what Mistress Evannah was going to do to me, if she were to leave marks on my flesh that would give my wife a clue to this secret rendezvous, or if she were to tempt me to stay and to not come back to my family for days, for weeks. I had waited years for this type of sexcapade, which I could only capture in my wildest dreams or in a porno, until now. Now it was all real.
She demanded me to come to her on all fours, and to bark like a dog. I was confined by her belt, but I obeyed. She stood on top of the round glass table; I crawled, on my knees and forearms, right underneath it, to look up her dress. I could see her cock; it was massive, a sight that made me want to cry with joy. I got up from underneath the table and drove my head up her dress, licking on the head of her dick. I wanted to undress her and set that cock free, but Mistress Evannah wouldn’t have it.
“Is that the way a good dog should behave?” she questioned, kicking me with her boots, making me fall back on the floor. I felt a bruise forming on my head, but I didn’t care about the pain. I loved it.
“Is that the way a good dog should behave?” she shouted, making the hairs on my neck rise up in suspense.
“No sir, I mean, no ma’am!”
She laughed, and responded to my silly reply by removing her belt from my wrists and pulling my shirt off. Then she released her vicious whip: a cat-o-nine tails. My stomach was forced against the floor, her heel pressed against my buttocks, ever so slightly penetrating into my asshole. A small painful groan came from my mouth, from the pain of the whip as well as the pain of the heel going into my virgin hole. She pushed it in with a slow pumping motion as she flicked the whip fast and quick; the sting was so sharp that it forced my ass up into the air, which forced her heel to penetrate into me deeper. Tears trickled down my cheek. I had never felt a pain such as this, it felt so good. She stopped until my entire back was patched with red spots and blue bruises; when she pulled her heel out of me, my asshole was sore and throbbing. I collapsed onto my back.
“Did doggy learn his lesson?”
I nodded. I was too overwhelmed for words.
“Stay where you are!” she smirked. “Mommy needs to sit down and relax; all this punishment can make her awfully tired.”
Her soft luscious ass covered my face; it was smooth and hairless, smelling faintly of baby powder. A huge diamond circle protruded from her asshole; it was a steel butt plug with a diamond-studded handle. She bounced on my visage and gyrated into me, moaning softly, demanding me to lick her asshole. I swallowed the base of her butt plug into my mouth, and pulled it out slowly. I stretched her ass cheeks as I pulled the plug completely out from her hole. My tongue plunged deep, swirling around her insides. Her hole clenched around my tongue and then opened up again as I greedily ate out her ass. My hands reaching for her cock from underneath her dress. The veins felt more prominent than before. That cock was going to explode.
“May I please suck you off Mistress?” I asked, while my tongue was still inside of her. She didn’t hear me. I pushed her ass up away from my mouth, and asked again, but she suffocated me with her bottom, and I was forced to eat her out some more. She got off me and lay back on the leather couch, spread eagle. She whistled at me to come over, and then at last she allowed me to play with her cock. It was even larger and longer than before. Her balls were full and heavy. I had no idea how I was going to handle it. She could read my thoughts, sense my intimidation. She smirked evilly, grabbed my head, cooing “Come here baby,” and forced her cock into my mouth.
Even with only her head inside my mouth felt full. She closed her eyes and kicked her head back in a moan as she pushed her cock deeper. With smooth, fluid thrusts she inched her cock down into my throat. I could hardly breathe, I winced in disbelief that she had forced it all in. Her fingers ran through my hair, sweet and gently, and then she pulled it roughly, pulling my mouth away from her cock completely. I gasped for air, my heart was racing. I closed my eyes for but a second before her entire cock was down my throat again. She pounded into me relentlessly. Suddenly, she grabbed me by my hair, and dragged me into the kitchen, with her cock acting as my gag and my leash. My throat was sore, my mouth was hurting; I couldn’t even let out a moan, a whimper, or a cry. She released her cock out of my mouth once more, gagged my mouth with a damp wash cloth, and smacked my face hard.
“I don’t need the neighbors to call the cops again for ‘disturbing the peace’,” she stated.
“So you better keep your fucking mouth shut.”
She grabbed another washcloth and tied my wrists around the leg of a chair, so tightly that it burned. She got her goody bag and took out a collar and leash, putting it around my neck. She dripped a bottle of lubricant along my ass; she lubricated my tight virgin ass and then her dick. I hoped it would lessen the pain of what she was about to do. The cool chain of the leash slid down my back, making me shiver. I felt her finger gently penetrate my asshole.
“It is so fucking tight.” she remarked. “You are a virgin, I can tell.”
She pushed her finger into my ass up to the knuckle, added another finger, and another, knuckles-deep. My eyes were closed tight and my body was shaking from head to toe; I let out a muffled moan through the wash cloth gag.
“My cock is going to rip your ass in two,” she cooed. “Hold on tight darling, you are going to be in a world of pain.”
I was afraid it was going to be all too much, but I didn’t have a choice. She held onto the leash, and pulled my head back, so she could force me to look at her as she fucked me. I could feel the head of her cock stretching me wide; the lube made the entrance easier, but not less painful. I was in pain, but it was an intensely good pain.
Her hand smacked my ass cheeks as she pushed inch after inch into me, slowly at first. And then she decided to turn up the vigor and speed. I knew she was determined to put all of her huge cock in, even if it killed me. I felt her pump into me, balls smacking hard and sharp against my thigh. She drilled her cock into me faster and faster, deeper and deeper, stretching my asshole wider, until finally she had all of her inside of me. She filled my hole up entirely; my sphincter wrapped so tight around her cock that I heard my Mistress Cupcake curse, “Goddamn you fuckin’ tight-holed virgins!”
She pulled out, releasing her seed all across the floor. She didn’t just ooze, she catapulted. Spurts of semen landed on the floor, on the chair, on the counter top, on my feet, between my toes. She fell back, demanding me to clean it up. After she let me go from the bondage and took the collar off of my neck, I lapped up every drop from the floor: her cum tasted so fresh and sweet. It pleased her well.
“Good boy…” she sighed. “Now you can do me one more favor. I want you to fuck me, fuck me as if you are fucking your wife.”
I had been waiting for weeks to do this. I was the boss now. I forced her arms behind her back and bent her over the counter, dunking her face into the sink water. She seemed to love it. I spread her ass open. My cock was not even close to being as big as hers, but I drove deep into her anyway, as she had done to me. I had never entered my cock into a man’s ass before; it was unbelievably tight, nasty, hot. Each time she moaned I dunked her head into the sink water, groaning “Don’t want the neighbors to call the cops, right?” Her asshole pulled my cock into her greedily; whenever I pulled out, it was blinking for more. I pulled her head out of the water, so to let her breathe. The wig fell off; the illusion was gone, she was now a man wearing a dress, makeup dripping down her face, lipstick smeared, he was a hot, filthy, sexy mess.
“What is your wife’s name?” he panted, spitting sink water from his mouth.
“Roxanne…why?”
“Call me Roxanne, bitch.”
Somehow, that really turned me on. I didn’t know what came over me, but I pounded Alexander to the extreme, balls deep into his asshole, screaming “Roxanne! Roxanne! Roxanne!” Each time I said my wife’s name, it made me want to come. His ass devoured me; it was as if his ass was more in control than my cock. Alexander revolved his ass onto me deeper and deeper in unison with the pumping of my cock. I tweaked his nipples through his dress, grabbed hold of his dick, I was going to come. In seconds I climaxed inside his hole. It was the most amazing feeling in the world, to cum inside of a man. Fully spent, I crumpled to the floor, wiping the sweat from my face. He stepped on top of my chest in those platform shoes. My seed was drizzling down his thigh. I was in ecstasy, he was on fire. He wiped his face with the cloth that he had gagged me with. The makeup ran down his face, his lips were stained with blood from biting them.
In his normal masculine voice, he said “You have got a lot of explaining to do with your wife. You got bruises all over, your dick looks sore, your asshole is gaped wide open…how are you going to explain that to her when you get home?” He laughed.
I thought of asking him if I could stay the night, but I didn’t want to overstay my welcome.
“I guess I will have to think about that on my way back,” I chuckled.
He picked me up by the hands, wiped his lips, and kissed me. My body was wounded and bruised, awfully weak and tired, but my heart yearned for the love of a man: it was strong. Just when I thought that he was going to say goodbye, with a firm hand he took me to his bedroom, and shut the door.
I had no other choice, I was there to stay.
Originally published October 2010