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Crossdressing

My Best Kept Secret

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Paul
Paul (born Paula) is a transgender man seeking companionship. His family recently rejected his new way of life, leaving him feeling depressed and alone. That is until he met Terry.
Terry
A gorgeous, successful model who’s accustomed to getting what she wants. Ava attends upscale parties and is well-known on the social scene. She’s confident and assertive with a hint of narcissism.

I’d never felt more like myself than I did when I was with Paul. Growing up attractive, you get all kinds of attention. People give you things you don’t even ask for including money, gifts, and attention. I hate to complain. I know there are many people less fortunate than me. Women who would kill for my body, my looks, and my popularity. But they don’t know what it’s like. They don’t understand the kind of pressure I’m under. It’s exhausting always putting on a show. Making sure you look good and are being politically correct. I was tired of being what everyone else wanted me to be. I just wanted to be me. Whoever the fuck that was anymore.

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I was proud to be on Terry’s arm. I know everyone says their girlfriend is gorgeous, but Terry really was. Supermodel gorgeous. Tall, thin, flowing brown hair, big tits, and a tiny waist. She’d dabbled in modeling in college but then landed a gig as a flight attendant on private jets. She had some pretty big-name clients and they were insanely generous with their tips. As long as cash tips were the only kind she was getting, I was good with it.

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Crossdressing

My Best Kept Secret

I’d never felt more like myself than I did when I was with Paul. Growing up attractive, you get all kinds of attention. People give you things you don’t even ask for including money, gifts, and attention. I hate to complain. I know there are many people less fortunate than me. Women who would kill for my body, my looks, and my popularity. But they don’t know what it’s like. They don’t understand the kind of pressure I’m under. It’s exhausting always putting on a show. Making sure you look good and are being politically correct. I was tired of being what everyone else wanted me to be. I just wanted to be me. Whoever the fuck that was anymore.

 

Things were different with Paul. He made me feel beautiful no matter what. He cared about the person I truly was. He was interested in my dreams, my goals, and helping me achieve them. That’s why he was by my side tonight at this stuffy party where I had to mingle with pilots, actors, and agents. I was inside putting on a good show when I really wanted to be outside on the balcony, enjoying a relaxing cigarette with Paul. Actually, where I really wanted to be was home sucking and fucking him, but that would have to wait.

 

I glanced over the crowd and spotted him outside, a casual smirk on his face. He was always so relaxed. I swirled the red straw of my cocktail around my tongue, imagining his mouth on mine. My nipples perked up at the thought of his head between my legs. He knew how to eat pussy like no one I’d ever met before. Paul smiled and looked down, knowing exactly what I had in mind. He jerked his head toward the door and I nodded eagerly. We were both ready to get the fuck out of there and get home to fuck.

 

I politely excused myself and headed to the elevator. He was waiting for me on the other side and like a magnet, his body gravitated toward mine. His hand found my pussy, squeezing the soft flesh through my tight dress. I grabbed his face, shoving my tongue deep in his mouth. He tasted of cigarettes and whiskey. My head buzzed after two drinks and all I could think about was getting him into bed.

 

We stumbled our way to the truck and he opened the door for me. Paul was always such a gentleman. As I pulled myself up into the passenger seat, he fondled my bare ass under my dress. He climbed into the driver seat, revving up the truck and speeding out of the parking garage. My head fell back. I was drunk on desire and vodka. With closed eyes, I began fondling my tits. My nipples were fully erect as I pressed and kneaded my soft tits. I let my knees fall open, exposing my drenched pussy to the open air. Paul’s hand tickled its way between my legs, sliding up and down my slippery folds. His fingers penetrated my hole before gliding back up to my now throbbing clit. I gyrated my hips, riding his talented fingers, my body begging for his touch.

 

I gripped the door handle as he methodically finger-fucked me. The truck accelerated, sending waves of excitement up through my crotch and into my belly. He had two fingers buried deep inside me now and I thought I might explode all over his expert hand. But before I could, we pulled into the garage. He pulled his hand from between my legs and stared at me, slowly licking my thick cream from between his fingers. He loved the taste of my juice and I loved licking it from his chin and tongue. 

 

We exited the truck and I ran inside ahead of him. I stood in the living room, removing my dress with one fluid motion. Putting myself on display for Paul’s visual consumption. He loved my naked body and I got off on letting him eye-fuck me. I caressed my soft skin, grazing my nipples and my hairy busy before beckoning Paul with a single finger. 

 

He removed his shirt and undid his belt as he moved closer. I placed my hands on his chest which was flatter than a few months ago. I knew his nipples were tender so I touched them gently. I kissed his chest, gently blowing warm air over his erect nubs. He grunted as his hands explored my waist and ass. Paul dropped his pants, letting me briefly fondle the area between his legs. The stiffness I felt was where his clit used to be. Or should I say, where Paula’s clit once was. Paul would have his own glorious cock soon enough and when he did, it would be all mine for the taking. My pussy throbbed at the thought of taking every inch of his brand new tool.

 

He grabbed my wrists, pushing me backward onto the couch. I knew what he wanted and I was more than happy to give it to him. He knelt between my legs, shoving them open. I held behind my knees, looking down at Paul’s face just inches from my dripping pussy. I held my breath, anticipating the contact. He licked his lips and inhaled, taking in my scent. I bit my lip as he effortlessly plunged his fat tongue into my honey hole. I draped my legs over his back, pulling his head into my crotch. His tongue ran from my tight asshole all the way up to my clit, which was a hard, throbbing marble. Paul obediently stayed motionless between my legs, letting me hump and fuck his face but I wanted more.

 

I lowered my legs, grabbing his face and licking my pussy cream from his chin.

 

“Fuck me,” I whispered into his ear, nibbling and sucking the lobe.

 

He stood up, removing his underwear as I grabbed our favorite dildo and strap-on. Paul slipped the harness on, securing the realistic eight-inch cock in place. I wanted to suck it. I grabbed the shaft aggressively, wrapping my mouth around the fat head. Without warning, Paul grabbed my head, shoving the entire length of the flexible dildo down my throat. I gagged, pulling away but Paul gripped my head firmly, fucking my mouth with the dildo. 

 

I grabbed his thighs, pushing away more aggressively. As the cock slipped from my mouth, a long string of saliva hung from my chin. 

 

“Turn over,” Paul demanded. 

 

I rolled over onto all fours, my favorite position. Paul grabbed my ass, spreading my cheeks apart and teasing me with the tips of his fingers. He ran them up and down the length of my crack. I pushed back, begging for him to enter me. I felt the tip of his pinky slide into my asshole and I yelped. Paul knew I enjoyed a little ass play. I pushed down gently, welcoming his finger a little deeper into my forbidden zone.

 

He pulled out, spitting on his hand and preparing the realistic dildo for entry. He ran the fat head up and down my pussy folds, lubricating it with my thick cream. I arched my back as he finally penetrated my dripping cunt with the fat head of the dildo. My pussy spread open, welcoming the familiar sensation of my favorite dildo. He grabbed my hair, pulling my head upward and slowly burying the cock inch-by-inch. I cried out as he buried the entire length into my cunt. He pulled my hair and fucked me hard and fast. I gripped the couch, bracing myself against his thrusts. 

 

I reached between my legs, working my swollen clit, imaging Paul’s own nub throbbing with desire. The artificial balls of the dildo smacked my ass, sending waves of pleasure through my ass and up my belly to my nipples. Paul delivered a firm smack to my ass just as my body reached its height of pleasure. I screamed as the hot flood of cum rushed from my pussy, saturating the strap-on and the couch. Paul gripped my waist, steadying my body as it shook. I let out a heavy sigh, collapsing onto the couch in a fit of satisfaction and exhaustion. 

 

I turned over to face Paul. He was standing with his chest out, the cum-covered strap-on proudly on display. Without hesitation, I leaned in and started cleaning my pussy cream from the dildo. With my eyes closed and Paul’s hand resting on the back of my head, I fantasized about tasting my sweet cream on Paul’s own dick and a fresh flood of excitement filled my cunt. 

 

I was proud to be on Terry’s arm. I know everyone says their girlfriend is gorgeous, but Terry really was. Supermodel gorgeous. Tall, thin, flowing brown hair, big tits, and a tiny waist. She’d dabbled in modeling in college but then landed a gig as a flight attendant on private jets. She had some pretty big-name clients and they were insanely generous with their tips. As long as cash tips were the only kind she was getting, I was good with it.

 

We met on a dating app and hit it off immediately. She’d been through a recent break-up with a hot-headed Italian and was looking for someone gentle and kind. I fit the bill. I was shorter than her — masculine but sensitive, and had a tongue like a jackhammer. There were no complaints on her end.

 

I stared at her through the sliding glass door as she networked with big wig clients, pilots, and other professionals. I wasn’t much for socializing in big groups or putting on a front. I took a deep drag from my cigarette, leaning against the rooftop railing. It was a chilly night. My breath poured from my mouth in large clouds. Terry looked over the shoulder of the man who was most likely rambling on about travel guidelines. She twirled the skinny red straw of her cocktail around her tongue and gently sucked it between her fat pink lips. I had other lips on my mind. 

 

I nodded in her direction, letting her know I was ready to get outta there and get her into bed. She matched my nod, breaking off her conversation, handing her empty glass to the cocktail waiter, and heading toward the elevator. We met in the parking garage, our bodies like magnets to one another. I grabbed her chubby pussy firmly in my hand and she yelped. I shoved my tongue in her mouth, tasting a mix of vodka and garlic from the appetizers. She squealed in delight as we kissed and fondled one another all the way to the truck.

 

I opened the passenger door, helping her in by grabbing her bare ass cheek. She never wore underwear and it drove me crazy. I climbed in the driver’s seat, eager to drive the 5 miles back to my apartment and get her completely naked. As I drove through the dark city streets, the street lights bounced off of her beautiful face and body. She gently stroked her breasts and nipples through her thin dress. I couldn’t help but reach over, tucking my hand into her warm, welcoming crotch. My hand was instantly met by sweet, warm, wetness. I ran my fingertips up and down the soft folds of her pussy. She pressed her knees outward, making it easier for me to reach her pleasure spot. I circled her swollen clit slowly, dipping my fingers down into her hole to gather more thick cream. She grabbed the door handle, pushing her body firmly into the seat as I methodically finger-fucked her. 

 

I pulled into my garage, turning off the truck abruptly and pulling my fingers from her pussy. I shoved them in my mouth, licking her cream from each digit. She was out of the truck before I was, bounding inside and into the living room. I chased behind her, kicking my boots off at the door and removing my jacket, tossing it on the kitchen counter. She stood in the middle of the large living room, removing her dress and exposing her gorgeous naked body. She was so slender. Her stomach was flat, tan, and defined. My eyes were first drawn to her perky tits and then her fat, hairy pussy. She rubbed her hands up and down her body, beckoning me closer with a single finger.

 

I stepped toward her, undoing my belt and removing my shirt. She placed her hands on my chest which was flatter now than a few months ago. The hormones were working but left my nipples especially tender. She was always so gentle with me, kissing my bare chest softly and blowing on my nipples. I dropped my pants, standing in just my boxer shorts now. Her hand gravitated toward my crotch, rubbing it through the thin fabric.

 

I grabbed her wrist and moved it away, pushing her toward the couch where she obediently sat. A huge smile spread across her face. She knew what was coming. I shoved her legs open and knelt before her, taking in the smell and sight of her cunt. It glistened under the moonlight pouring in the front windows. I dove between her legs eagerly. I was starving for her peach.

 

I shoved my tongue deep into her hole, scooping up her thick pussy cream. She draped her legs over my back, grabbing onto the back of my head where I recently shaved. I licked from her tight asshole up to her bush, circling her fat nub with my tongue. I could tell she was buzzed and horny by how aggressively she grinded her crotch against my face. I let her hump my tongue and move my head wherever she wanted. 

 

She sat up slightly, pulling my face to hers.

 

“Fuck me,” she begged, sucking and nibbling my earlobe.

 

I stood up, removing my underwear. She reached beside her on the couch, handing me the strap-on. Terry didn’t care that I didn’t have a real cock yet. She loved sucking and fucking her favorite strap-on and I loved giving it to her. I slipped my legs through the harness, securing the eight inch cock to my pelvis. She didn’t wait to deep throat the entire thing. I grabbed her head, helping shove the huge rubber dick completely down her throat. She gagged and tried to pull her mouth free but I wouldn’t let her. I thrusted my hips farther, fucking her mouth and fantasizing about her choking on a real dick. 

 

She pushed away from me hard, a string of thick saliva connecting her fat lips and the strap-on. 

 

“Turn over,” I instructed her, grabbing her legs and easily flipping her thin frame over onto all fours.

 

She grasped the back of the couch and shoved her ass toward me, begging for it. I spread her plump asscheeks apart, running the tip of fingers up and down her crack, briefly fingering her asshole with the tip of my pinky. She squirmed and giggled, pushing down on my tiny finger.

 

I popped it out and spit in my hand, lubing up the shaft of the dildo. Her drenched pussy engulfed the fat head with ease. I guided the tip of the rubber cock into her hole, watching the lips spread around the fat, round head. Terry’s back arched as she accepted the thick shaft. I buried another inch in, grabbing her hair and yanking her head backwards. She cried out as I drove the entire rubber dick into her loose cunt. I pulled harder on her hair as I fucked her with deep, long strokes. My clit throbbed and I felt wetness running down my inner thighs. I couldn’t wait to have my own magic wand to fuck her with.

 

She reached between her legs, rubbing her own swollen nub as I continued to drive it home. Her perky tits bounced vigorously beneath her. Her moans caught in her throat as I bent her neck back an inch further. The fake balls of the strap on slapped her ass, which I used as a handle, squeezing and pulling her flesh. I gave her butt a firm smack and she screamed. She was cumming. I thought I felt her pussy clamp down on the strap-on. I closed my eyes, imagining her soft wet cunt squeezing my cock and showering it in a thick coat of cum. 

 

I wished I could fill her hole with my own hot load of salty cum. I continued to pound her pussy until she came and squirted all over the dildo, the couch, and my thighs. Terry collapsed onto the cushions, breathing heavily and pulling her hair from my hands. 

 

I step backwards, the giant cock covered in her hot wetness. I felt powerful standing there, in control of such a large tool. A tool that pleasured Terry’s pussy so many times. She leaned in without hesitation and began cleaning her cum from the shaft. I closed my eyes once more and fantasized about jizzing on her face and down her throat.

 

One day. 

 

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