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Anal Crossdressing

SHE.

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Ryan
Ryan is a 40-year-old husband and father. He sells insurance and travels for work regularly. His schedule allows him to indulge in his insatiable hunger for transgender women.
Jasmin
Born as Jason, Jasmin is a transgender woman who works as a cocktail waitress at the local casino. Jasmin loves nothing more than flirting and shopping. She has a special interest in fashion and cosmetics.

Ryan was the only man I’d been with since my transformation. He’s the only one who made me feel beautiful in my own skin. Plus, he bought me gifts and had a cock like a stallion. For a straight guy, he sucked and fucked better than any other man I’d ever been with. He devoured my body like a sweet treat. Salivating over every inch and crevice. 

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Jasmin was the most beautiful woman I had ever laid eyes on. Long, platinum locks fell down her broad shoulders and round breasts, attached to subtle curves framing her gorgeous figure. Tall, toned legs that stretched for miles and a height on her that made me feel like an ant amongst men. She was a mixture of intimidation, beauty and a thrilling sexual drive that riled me in the most delicious ways. My cock pulsed in my pants at the mere thought of touching her. Jasmin had a talent that far exceeded anything I had ever experienced before her. One hour with the bronzed beauty and I would climax enough times to last a lifetime and yet, I would spend the entire week yearning for her- crazed for her special touch all over again. 

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Anal Crossdressing

SHE.

Ryan was the only man I’d been with since my transformation. He’s the only one who made me feel beautiful in my own skin. Plus, he bought me gifts and had a cock like a stallion. For a straight guy, he sucked and fucked better than any other man I’d ever been with. He devoured my body like a sweet treat. Salivating over every inch and crevice. 

 

I tried to ignore the fact that he was married. That after he finished with me he went home to her. I wondered what she looked like. Probably your typical frumpy, boring housewife. Obviously, she didn’t satisfy him or he wouldn’t feel the need to meet me every week in a seedy hotel. I didn’t want to take his money. In fact, at one point, I refused. Sure, I made my living having sex with strangers but Ryan was no stranger. Not anymore. I think that’s what scared him most. He knew that if he stopped paying for my services that our relationship would mean something more than just raw, animalistic sex.

 

Tonight was like every other, except I was wearing the gift he’d bought me. Red-bottom Louboutins. I’d been drooling over them since the first day I slipped into a dress and Ryan knew it. I’d shared things with him that I hadn’t shared with anyone else. The gift marked our one-year anniversary of meeting like this and tonight, I was gonna fuck him wearing those heels. My short dress barely covered the growing bulge in my pants. I got a hard-on at the thought of him waiting for me on the bed. His own quivering member twitching in anticipation. 

 

I pushed open the door and the familiar smell wafted up to my nose, enveloping my face and bringing my nipples to life. Ryan was already in position on the bed, his cock restrained by a tight, white jock-strap. I hungrily licked my lips, already tasting his salty cum on my tongue. He noticed my heels right away.

 

“You’re going to leave those on, right?” The excitement in his voice was undeniable. 

 

A grin spread across my face as I moved closer, placing a single finger under his chin and lifting his head.

 

“Of course I am,” I said playfully, glancing down at his crotch. His erection was growing with every word and caress.

 

I needed to taste him.

 

I lean down, bringing his soft lips to meet mine. He melts into my kiss, gladly parting his lips and exploring my mouth with his own. I firmly massage his tongue, sucking and flicking it the same way I do his cock. His hands are on me now, fumbling with my tight dress. Eager to touch my flesh. My cock throbs beneath the tight thong, straining to break free. I need his hands on me. I pull away, yanking the tight dress up over my head, exposing myself for him the same way I have so many times before.

 

Ryan’s eyes swell with desire as he scans my body. I feel like a powerful, sensual woman beneath his gaze. He grabs my chest, pulling me close and burying his hungry mouth between my breasts. I jam my leg between his knees, letting him hump and grind against my muscular thigh. His tongue makes quick work of exploring the soft flesh of my chest. I let out a deep moan, tugging at his hair as he pillages my body. 

 

I move around him, taking my own comfortable seat on the bed beside him. He knows what I want and swiftly moves between my legs, kneeling before me, always so eager to please. I hold myself steady as his strong hands work the tight thong from around my waist, down over my hips, and completely off. My enormous cock springs free, the cool air tickling the soft skin along the shaft. My veins are bulging in excitement as droplets of precum spill from my slit. 

 

Knowing I can’t wait much longer, Ryan grips my shaft firmly, his touch is warm and purposeful. I sit up straight, tossing my hair back over my shoulders and smiling in delight. I love a good blowjob, especially when I’m at the receiving end and it’s Ryan working my throbbing tool. I settle on my elbows, giving me an unobstructed view of the show between my legs. 

 

He grips my shaft tightly, holding it in place as his gorgeous mouth dips down, engulfing the head. I gasp at the contact. It’s been too long since I’ve felt that sweet, warm mouth wrapped around my cock. I watch intently as he hungrily explores my body. He gags, working his way down the length of my tool until I feel the tip tickling the back of his throat. He sucks cock like only someone with their own dick knows how to do. He knows what I like and never disappoints. 

 

His body is rocking back and forth as he eagerly humps the side of the bed. I envision his own cock hard and throbbing with desire, precum spilling onto the carpet. I run my fingers through his hair, tugging firmly and controlling his movements as he works my knob. 

 

“Fuck yes,” I grunt, lifting my hips slightly to bury my dick an inch further into his talented mouth. “You like my huge cock in your little throat, don’t you?” I tease and he moans, his mouth full with my tight flesh.

 

I pull my cock from his mouth, just in time to stop my inner explosion. 

 

I stand up, grabbing Ryan by the shoulders and turning him around. With a hand on his lower back, I encourage him to bend over. He smiles, happily obliging as he bends over, bracing himself on his knees. His ass looks more delicious than ever and I can’t help myself. I grab his soft, pale cheeks, eagerly spreading them open. I drop to my knees and notice his arms are shaking. The muscles in his legs and ass tighten in anticipation. I won’t torture him any longer.

 

I dip the tip of my tongue into his dark hole, circling the edge before plunging it deeper inside. I give his soft ass an aggressive smack and he flinches. I reach between his legs, ripping his jockstrap aside, finally unleashing his gorgeous cock. It flops generously into my hand, the skin warm and taut. My tongue never wavers, fucking his hole as my hand tends to his erection. The tip of his cock is wet with precum and I use it to lubricate his shaft. 

 

“Please”, he whimpers. He’s begging for release but it’s too soon. Far too soon.

 

“Please, Jasmin.” My name on his tongue is electrifying. My entire body hums with sexual energy. “Please fuck me.” His voice is desperate and thick with desire.

 

I give his ass one final smack before pulling my tongue from his tight rim. I sit back down on the bed, my cock waving freely, a clear invitation.

 

“Get that tight hole over here, baby,” I demand, leaning back on my elbows once again.

 

Ryan straddles me, perfectly aligning his tight, wet hole with the head of my giant tool. I smile at the thought of our first time together. How tightly his ass puckered when I tried to enter him. With enough lube, toys, and practice, his hole now devours my cock easily. But not without a little teasing first. He grabs the shaft, circling his rim with my slick cock. I watch intently as he lowers himself onto my tool. His body opening up for me, pulling me inside one inch at a time. The inner walls of his body tighten around my shaft as the muscles twitch and release. 

 

I close my eyes, relishing in the familiar warmth of his body. He’s riding me now with long, smooth movements, lifting and lowering his body as he firmly grabs my chest. His hands are on my breasts, pinching my nipples as his ass works my cock. He picks up speed, bouncing aggressively on my thick member, his ass cheeks smacking against my flesh. Ryan’s hands grip at his own erection, feverishly yanking on it with the same rhythm as he rides me. I see the pleasure building in his eyes and yearn for his hot load on my body. Not so fast. 

 

I lift Ryan by the hips, tossing him aside, just in time to quell both of our orgasms.

 

“We’re not done yet, sissy,” I said, using my pet name for him.

 

I lay Ryan down, kneeling between his legs and draping them into my shoulders. His legs are shaking in anticipation. The tip of my throbbing cock is in line with his tight hole and I pause, drunk with the power I have over him. I lean forward, easily sliding into his premoistened, gaping hole. He gasps at my forcefulness, pushing back against my body and burying my dick an inch deeper with ease. I fall onto the bed, supporting myself above him and fucking with a new verosity I never knew existed inside me. 

 

“Please”, he pleads to me. He’s ready.

 

I smile, more than happy to relent to his deep need for me. 

 

I pick up the pace, fucking him hard and fast as my balls gently tap against his. I’m deeper now than I’ve ever been before and I feel his ass gripping the tip of my cock, coaxing my own orgasm from deep within. 

 

“That’s it,” I urge him. “Let it out, baby.” 

 

I feel his ass constrict and release as a stream of hot cum explodes from his cock, landing on his stomach and the mattress beside him. Naughty boy.

 

I pull myself free, my cock slick with his juice and residue. I move next to him on the bed.

 

“My turn,” I said coyly, kneeling on the mattress and directing his mouth to meet my waiting tool. I hold his head steady as I vigorously stroke my cock, preparing my own load for delivery. He licks his lips, hungry for my cum. I press my legs firmly into the soft mattress, my muscles straining as I yank my cock to the point of no return. Like a tidal wave, my orgasm erupts from the tip of my cock, coating Ryan’s lips and tongue in my salty treat.

 

I smile down at Ryan before stumbling away from the bed, retrieving my dress from the floor. I leave him to bask in euphoria. I gather my things and slip the envelope into my bag, feeling equal parts guilty and pleased. I didn’t want Ryan’s money. I just wanted him.

 

“That was fun, sissy,” I say, flipping my hair back and plastering on a half-hearted smile. “Text me with the time and place, next week, yeah?” 

 

He doesn’t speak, just nods his head, his eyes closed, a satisfied grin decorating his perfect face. He peeks up momentarily, barely lifting his head as I give him a playful wink and quietly exit the room. 

 

Till next time. 

 

Jasmin was the most beautiful woman I had ever laid eyes on. Long, platinum locks fell down her broad shoulders and round breasts, attached to subtle curves framing her gorgeous figure. Tall, toned legs that stretched for miles and a height on her that made me feel like an ant amongst men. She was a mixture of intimidation, beauty and a thrilling sexual drive that riled me in the most delicious ways. My cock pulsed in my pants at the mere thought of touching her. Jasmin had a talent that far exceeded anything I had ever experienced before her. One hour with the bronzed beauty and I would climax enough times to last a lifetime and yet, I would spend the entire week yearning for her- crazed for her special touch all over again. 

 

I had spent the last six months convincing my wife that I had been travelling for work, as I scout for cheap motels in the area where Jasmin and I could finally indulge in each others appetites. As I spend every Friday night compelled by the secret affair, I would feel a sense of guilt grip at my core. I loved my wife and I adored the life we built together. Nonetheless, Jasmin was a hurricane that ripped through my barnyard soul and with every inch of guilt, came a mile of starving lust that would override any moral thought that would stop me. 

 

I lay the envelope of cash on the dusty nightstand before anything else. I knew the drill; discretion in business eliminates that gut-wrenching feeling of disconnect when she inevitably has to leave. I slowly undress, folding my grey suit over an arm-chair in the corner of the room, baring down to be ready for her. I sit on the bed in nothing apart from a white jock-strap, hugging my throbbing cock as I await her presence with a fiery anticipation.

 

I jump at the sudden jiggling of the door handle at the entrance of my room. My heart races, walking myself through a quick mental marathon, recollecting my texts with Jasmin to make sure it was really her coming to meet me. 

Her blonde locks flick over her shoulders as she slides into the room and I instantly melt into the mattress below me. 

Locking the door behind her, she swivels on her step to face me with a heart-stopping smile stretching over her sharp features. She was just as beautiful as I remembered. 

 

She stalked toward me without a single word and I inhale the sight of her with shaky, infinitely aroused breaths. 

Her short, sequinned dress shimmered in the dull motel-room lamps, with dark fishnet stockings leaving a pool of saliva to dare drip from my mouth. She’s wearing the tall, red-bottom Louboutin’s I bought for her and, wow, she wore them like they were designed just for her. 

 

“You’re going to leave those on, right?” I stuttered, pointing down at the sleek heels. Her grin widened as she came to a stop in-front of me, enticing me to stand with a single finger hooked under my chin. 

 

“Of course I am,” she purred and my cock vibrates, pushing painfully against the jock-strap. 

 

She ducks her head, leaning down to place a long, luscious kiss onto my quivering lips. Her warm, plump mouth smoothes over mine with practised brushes, whilst my knees buckle and tremble beneath her proximity. She pushes her tongue between my lips and with the delicious scent of smoke and whiskey, begins massaging my tongue with hers. I groan into her kiss, fumbling my jittery hands up the sides of her dress, the scratchy material teasing me as I torment myself with the thought of what lay underneath.  Our mouths become rabid for each others taste, moving in messy, ferocious licks and gasps. She pulls away from my mouth for a brief moment, tugging her shimmering dress over her head with a single, swift tug. 

 

I practically melt to her feet, letting out an audible grumble as I trace my perverted sights over her lean body. A dark, royal blue set of laced lingerie hugged her intoxicating frame. Her push-up squeezed her round breasts together, her suspender hung onto corners of her fishnets, with a thin, blue thong stretched over her giant, pulsating bulge. I push my face between her breasts, licking at her hot skin as my hips thrust against her bare leg with an uncontrollable, overwhelming need to feel her. She walks around me, sitting on the bed with an expectant, lust-filled stare encasing her expression. I follow her like a light in the dark, crouching by her feet as I pull on her thin thong, dragging it down her toned legs. I swallow, hard, staring in awe as her thick length bounced from the freedom of her undergarment. Her veiny, warm cock twitched as it waited eagerly for my attention, the view itself feeding a deep ache that swam through my entire body. 

 

I wrap a perspiring palm around the base of her girth, utterly consumed by the sheer size of her hard member. She flicks her long hair behind her shoulders, a devilish smirk eating me up as she leans back onto her elbows for a clearer view. I moan a press my hard cock against the side of the bed, between her legs. I lean over her, mouth salivating for the taste of her. I wrap my lips around her knob first, sucking up her sweet, wet arousal as she sighs out a small, adoring hum. 

I duck my head further and with a deep breath, take her overwhelming length down my throat. I smooth my tongue down her shaft as I swallow and suck on her like her hard cock was oxygen and I was desperate for fresh air. I choke and gag on her impossible girth, groaning and moaning around every mouthful as my own cock grinds painfully against the side of her leg. Her head falls back at the sensation and she moans into the air, running her long fingers through my hair before gripping onto my head to control my pace. She pushes my head down further, forcing me to gag on her length over and over again. She sighs out in euphoria and I bask in the honour to pleasure her like this.

“Fuck, yes,” she grunts, bucking her hips to match my eager strokes. 

“You like my huge cock in your little throat, don’t you?” She teases and I moan around her length in pure bliss. 

 

She roars, pulling on my hair to tug me from her pulsating shaft. She sits back up, swivelling me around, pushing a hand on my upper back to entice me to bend over. I do as she pleases, placing my hands onto my knees to balance myself as she parts my hot cheeks with long, manicured fingertips. My knees tremble, anticipating her warm, wet tongue as she plunges between my cheeks with a starving caress. Her tongue circles around my tight hole, teasing and enticing me, waves of pleasure rippling through my nerves as I let small whimpers, entrapped within her hold. She uses one hand to smack at my heated skin, spanking my tender cheek as she licks and strokes and eats my little hole with her gorgeous tongue. With her other hand, she pushes between my thighs and pulls my jock-strap to the side to release my painfully needy cock. She begins stroking my length with long, practiced tugs, her tongue unmoving from my greedy rim that sent pangs of pleasure to beam through me, screaming at me for release. I close my eyes, moaning into her experienced touch, revelling in the glorious sensations that rippled around me as she devoured me, enveloping me with her talented caress.

“Please,” I plea, needing to feel her inside me.
“Please, Jasmin, please fuck me,” I moan, feeling my limbs stiffen as she edges me to the point of climax. She pulls away just in time, spanking my cheeks with hard thwacks before I turn around to straddle her.

“Get that tight hole over here, baby,” she purrs and leans back onto her elbows once more. 

 

Her impossible length throbs and twitches in the air as I climb over her, straddling her and lining my puckered rim up with her thick knob, sleek with arousal. I grab her cock and circle my hole, teasing and wetting her length with the delicious saliva she’d left on me, groaning at the anticipation- the overwhelming euphoria I knew I’d feel when I finally had her inside of me. She looks up at me with a hungry gaze, studying my quivering features as I fall around her hard, thick member. I sink around her, tremors of pleasure and pain ripping through me as she fills my hole with her girth- her veiny, gorgeous shaft scraping along my walls until my cheeks meet the base of her pelvis. She croaks out a long groan, gorgeous lips parted as she disappears inside me. I moan loudly, overcome with the most intense need to come all over her gorgeous body. 

 

As I pull back up, feeling her length all over again, I smooth my hands up her torso, cupping and squeezing her perfect breasts as I grind around her, every inch of her stretching my hole. I pinch and pull at her nipples, riding her, lost in the sensation of her veiny cock filling me over and over again. I pick up momentum, slapping my cheeks on her hips with each bounce, indulging her perfect moans, high from her focused, enthralled stare. She grabs onto my hips, pulling me back and forth, using me to pleasure her as hard and fast as she needed. I’m a catastrophe of moans and intoxication, gripping onto her captivating rack with one hand, pulling on my thudding cock with the other. I feel myself edging once again, wanting nothing more than to release my climax all over her beautiful chest. 

 

She senses it in my tense limbs and throws me to the side, pulling out of me just before I could finish and I groan in protest.

“We’re not done yet, sissy,” she asserts and climbs over me as I my entire core vibrates with the overwhelming need to come for her. She kneels on the mattress, lifting my shaking legs to sit atop her shoulders and leans in, too fast, sinking back into me with a forceful push. The sudden fullness forced a disgruntled whimper to rip from my throat and I grasp onto her smooth hips, unsure if I wanted her to stop, or to never ever pull out of my aching hole. She slams into me with a newfound heat, grunting and moaning as she leans over me, her gorgeous, sweaty features mere inches away from my face as she fucks me hard and fast and utterly provocative. She huffs out deep groans, the manly sound of her groans tugging on my arousal more than anything else.


As she thrusts into me, pounding my little hole entirely for her own pleasure, I feel that glorious sensation climbing up my spine.

“Please,” I beg. She responds with a satisfied smile, using my plea as momentum as she fastens her pace.
She bucks her hips, her hard member digging deeper than I had ever felt and my body loses all control. I feel my release rippling through me in delicious bursts and I come, hard, all over my stomach. I cry out, exhaling deeply as she continues to push inside me, riding out my climax with a devilish smirk.

“That’s it,” she hisses through gritted teeth. “Let it out, baby.” She coos. 

I begin to melt into the mattress, limbs limp and exhales shaky. She pulls out of me slowly, stepping onto the side of the mattress.

“My turn,” she purrs and kneels slightly onto the edge of the bed, forcing my head to face her as she strokes and tugs on her pulsating length. I open my mouth, salivating and drooling for the taste of her load. She looks down at my twitching frame as she tugs hard on her length, eagerly jerking herself as she climbs to her own release. Her gorgeous, plump lips part softly and she moans into the otherwise silent room. Her legs stiffen and she fumbles her rhythm, relentlessly tugging on herself until she comes with a roaring height. Her warm, salty come bursts onto my face and stretch my tongue out, starved to taste her beautiful release, consumed by the pure eroticism.   

 

She huffs and pants as her mind trails back to earth and I watch in awe, completely captivated by the magnificent goddess standing over me. The room falls silent and just as I was becoming convinced that I could live in this moment forever, she looks down at me with an exhausted grin, stumbling back as she searches for her discarded clothes. I audibly sighed the moment she hid her chiselled frame back under her dress, laying naked and stunned as she walks over to the bedside table, sliding the envelope into her small handbag.

“That was fun, sissy.” She chimed, fluffing her blonde curls, recorrecting her appearance like none of this happened.
“Text me with the time and place, next week, yeah?” she continues. 

I nod, still lost in the intensity of the last hour- still shaking and unmoving from the pool of arousal and sweat seeping through the sheets beneath me. 

 

She stalks back to the door, turns the handle and flicks me one last, mischievous wink, before disappearing into the cold night. I instantly began counting down the days until I could see her again. 

 

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