Back
Anal Crossdressing

A Different Kind of Girl

Choose character:
Ron
Ron is an unhappily married 47-year-old with a hidden desire for transexuals. Ron’s confused about his sexuality but is drawn to drag queens and men posing as women. He keeps his secret life hidden from his wife of 15 years and his friends.
Toby
Toby (born Thomas) is a transgender club performer. Toby loves dressing in wild and outlandish outfits and performing for large crowds. She thrives on being the center of attention.

I’d see him at every one of my shows. He always sat at the same table, in front, right beside the stage. He wanted a good look. At first, I was irritated by him. Was he just coming to gawk at me? To see the freak show and laugh about it later with his buddies? But then I realized there was something more to it. He always came alone. Although he wore a wedding ring, he didn’t look at me like a married man. Shit, he didn’t even look at me like a straight guy. His eyes were hungry with desire. They were glued to my body the instant I hit the stage until the curtains closed. 

...Read more

As I entered the club for the fourth time that week, I had only one thing on my mind. The real question was whether I’d be able to get the result I so longed for, or whether I’d be shut down by rejection in minutes flat. 

...Read more

Unlock Unlock All Stories
A Different Kind of Girl A Different Kind of Girl
Listen to sample
A Different Kind of Girl A Different Kind of Girl
Listen to sample
Image
Back
Unlock All Stories
Close
Anal Crossdressing

A Different Kind of Girl

I’d see him at every one of my shows. He always sat at the same table, in front, right beside the stage. He wanted a good look. At first, I was irritated by him. Was he just coming to gawk at me? To see the freak show and laugh about it later with his buddies? But then I realized there was something more to it. He always came alone. Although he wore a wedding ring, he didn’t look at me like a married man. Shit, he didn’t even look at me like a straight guy. His eyes were hungry with desire. They were glued to my body the instant I hit the stage until the curtains closed. 

 

If I’m being honest, he made my job pretty difficult. It’s not easy to conceal a 9-inch cock in layers of spandex. It was hard enough spending hours on my make-up, applying fake eyelashes and fingernails, and teaching myself to not only walk but dance in heels. Now, this guy comes in, eye-fucking me every night and giving me wood. Why was his stare so intense? Why did it electrify me in ways I hadn’t felt in years.

 

On this particular night, he looked especially desperate to make contact. He sat on the edge of his seat during the entire show. He mouthed the lyrics along with me and clapped louder and longer than anyone else. He even stood up. As the curtains closed, I muffled a laugh. He was like a crazed, horny teenager and I was the object of his affection. I was actually a little flattered. 

 

As I headed to the dressing room, I heard a commission over my shoulder. It was him. He was getting turned away by the security guard. A flood of excitement filled my stomach. I’d never had someone pursue me so aggressively. Not like this, anyway. Not here. For a moment, I hesitated. Wondering if he knew what he was getting into. But my desire quickly overtook my doubt.

 

“He can come back through, Darren,” I said, without looking at my devoted fan.

 

I walked down the hall to my dressing room and slipped inside. I quickly took off the heavy sequin dress and positioned myself seductively on the large armchair beside my vanity. He entered the room seconds later, his erection already visible through his pants. I was instantly hard, my own cock straining uncomfortably between my legs. 

 

He stumbled into the room, his eyes fixated on my body. He shut the door behind him and I was instantly anxious.

 

“You wanted to get my attention, hm?” I asked teasingly. “Well, here I am,” I said, gesturing 

down at my body.

 

“I want more than your attention,” he said, licking his lips. 

 

My stomach tightened with desire, but I was still hesitant. Still holding back.

 

“You do know this is all an act right,” I said gesturing at my clothes once again. “That underneath all of this is a man’s body, not a…”.

 

He cut me off before I could finish.

 

“I don’t care.” He sounded so assertive and confident. “Look, I know you’re not really a woman, that it’s part of your act, but every time I see you, you drive me bloody wild. I can’t think about anything else.”

 

He was pacing back and forth now, like a caged animal. 

 

I felt like I had to do something to calm his nerves. I stood up, walking closer to him.

 

“Well now, you’d better come get me, then.” 

 

We were chest to chest now and I swiftly dropped to my knees, grabbing his erection on my way down. My hand easily slid into his trousers. His skin was warm and moist, his cock stiff in my hand. I squeezed his erection, firmly stroking the length of his cock. I was pleased. He was pretty hung for an average guy. I know how he wanted to be touched and worked his dick the way I would my own. 

 

He looked down at me, watching intently.

 

“I want you to ride me,” he said abruptly, his voice shaking. 

 

We made eye contact and I paused. Was he serious? My asshole tightened at the idea of riding my mystery admirer. I stood up, undoing my suspenders and removing my underwear. My giant tool sprung free, relieved to finally be let out of its tight, spandex prison. It twitched under his gaze. He reached out, pulling me toward him as he took a seat on the cushioned chair nearby.

 

His own dick was sticking straight up toward the ceiling, waiting for me. He spit into his hand and started gently stroking himself before steadying his dick at the base. I turned around, pulling my ass cheeks open, and slowly lowering myself onto his tool. The moistened tip easily broke through my barrier, slowly sliding into my gaping hole. I held his knees, lowering myself completely onto his throbbing shaft. He grunted, gripping my waist and helping me slowly descend. 

 

He was balls deep now and with a firm grip on his knees, I began riding his glorious tool. He gripped my hips and ass, controlling my every movement. 

 

“Fuck, yes. Come on. Ride me harder…”, he pleaded. 

 

I  could tell by the intensity in his voice that this was his first time with a man. Maybe his first time having anal sex. His dick was throbbing inside me, growing with every thrust. 

 

“Yeah?” I said, gritting my teeth. “You like me riding you like this?” 

 

“I fucking love it…”, he grunted, thrusting his hips upward, his balls rhythmically tapping my ass. “Ride that cock for me, baby. Come on. Fuck me, yes, ride that cock nice and hard for me!”

 

I lifted my body up, causing the head of his cock to almost release before plunging him back inside. I worked my hips in circles, grinding hard against his lap. He squeezed harder and I felt the muscles in his legs and arms tighten. His voice broke my thoughts.

 

“Get on your knees.”

 

I stood up, easing his dick out of me, and turned to face him. His cock was covered in wetness and residue. He held it steady as we both stared at its impressive length. He stroked it slowly, carefully. He didn’t want to waste his load and I wasn’t about to let him.

 

I dropped to my knees, wiggling my body between his legs and opening my mouth. I eagerly waited, my tongue out and ready. It only took a few strokes for the tip of his cock to erupt in a flurry of hot, white jizz. I closed my eyes as the shower of cum covered my face and chin. I caught some in my mouth, salivating over its thick, salty taste. With two fingers, I scooped up droplets of cum from my checks and sucked them clean. 

 

I crawled a few inches closer to his crotch, hungry for more. I wasn’t done with him yet. I grabbed the base of his cock which was still half-erect and stroked it slowly. It quickly came back to life in my hands and I licked my lips in anticipation. 

 

“I think I should clean this up for you,” I said playfully. 

 

Before he could respond, I dipped down, lowering my entire mouth onto his shaft. My tongue swirled around the tight skin, which tasted like dirty sex. I relished in that familiar feeling as I sucked my way to round 2.

 

As I entered the club for the fourth time that week, I had only one thing on my mind. The real question was whether I’d be able to get the result I so longed for, or whether I’d be shut down by rejection in minutes flat. 

Just like normal, I made my way past row upon row of tables, right to the front of the stage; I took my place, made myself comfy, and waited for the lights to dim and the show to begin. The moment the lights dropped down low to a mysterious shade of blue, the dust specs swirling in the air, I knew I was about to see him again. Or perhaps I should say see her again. 

Throughout the entirety of the show I sat transfixed, my eyes rovering over every inch of her immaculate outfit. Her long, shapely legs, the sequined sparkle of her bodycon dress, the way her ruby red lips mouthed the words to every song; every element of her performance was perfection personified. By the time her show came to an end, I was clapping and cheering the loudest, eager for her to hear my voice amongst all the others. To my relief, her eyes spotted me as she took a bow, a mischievous twinkle dancing in her irises meant only for me. 

The moment the show was officially over, I rushed from my seat and towards the back of the stage, desperate to not miss my chance. But no sooner had I started to close the line to the staff only area, a bouncer rudely spoiled my plans by stepping out in front of me. Standing as still as stone, he eyed me cooly, his expression enough to inform me that only upon pain of death was I to get past him. Deflated, I turned to leave, my hope of getting her alone dashed against the rocks of an angry shore. Then, to my amazement, the trill of her voice beckoned for me from down the unseen corridor beyond, “He can come through, Darren.”

Rather smugly, I sauntered past the bouncer and down to her dressing room, the door already ajar and waiting for me. I pushed it open and peered inside, blown away by the vision that awaited me. Perched on her dressing room chair, she sat in a black lace bodice, finished off with matching suspenders, no doubt the ones that had clung to her thighs during the performance. For a moment I couldn’t do anything except gasp and stare. It was only when she giggled at my reaction that I shook myself into moving and ventured fully inside, making sure to close the door behind me. 

“You wanted my attention, hm? Well, here I am.” She said, her eyes still alight with the playful flames of that sparkle she’d shown me on stage. 

“I want more than your attention.” I admitted, my mouth watering at the sight of her. 

“You do know this is all an act, right, that underneath all of this is a man’s body not a—”

“I don’t care,” I interrupted, unable to hold myself back. “Look, I know you’re not really a woman, that it’s part of your act, but every time I see you you drive me bloody wild. I can’t think about anything else.” Part of me was embarrassed by my outburst, but another part of me was proud that I’d said my piece, especially when I watched her sway towards, her notable curves enhanced by the shadows of the room’s lighting. 

“Well now, you’d better come get me then.” Was all she said before she dropped to her knees and plunged her hand into my trousers, her fingers immediately finding my rock hard cock. Within seconds she was working my shaft, her touch more skilled than any woman I’d had the pleasure of knowing before. As she continued to wank me off, her hand moving with a fluidity that only someone with a cock could truly understand, I found myself thirsty for something more than a mere hand job. If this was happening, it was going to happen exactly how I’d imagined it every night since seeing her.

“I want you to ride me.” I told her, my cock flexing between us as we looked into each other’s eyes, her hand still stroking me. At first she didn’t react, much to my concern, but then finally she sprung into action, her hands moving fast to unfasten her suspenders and remove her knickers. When she pulled them down, her enormous, hard cock caught my gaze. I was amazed that such a large length had been concealed so well, her underwear having never hinted at its presence earlier. Even though I could see it, it didn’t change the way I wanted her, nor did it break the illusion of her femininity as my hands groped for her to come closer. 

As she backed up onto my lap, she spread the exposed cheeks of her sculpted buttocks, her fingers holding her open so that she could lower herself onto me. During her descent, I moistened my cock with my spit, making sure to wet my shaft to help ease me inside. The tight knot of muscles and nerve endings widened to allow my entry, my member sinking into her as she slid down the full length of my hardness, her ass easily taking my girth. Once I was balls deep inside of her, she got to work riding me, her motion as skilled as a jockey; she bounced and bucked, her cock bouncing around wildly as I gripped her ass and helped her steer. 

“Fuck… yes. Come on… ride me harder…” I begged of her, my voice attempting to sound dominant but coming across more as a plea. 

“Yeah? You like me riding you… like this?” She asked, already knowing full well the answer I’d give.

“I fucking love it…” I groaned, my eyes rolling towards the back of my head as I neared closer to the inevitable conclusion of our tryst. “… ride that cock for me, baby… come on… Fuck me yes, ride that cock nice and hard for me…!” 

We both collided together, my cock almost fully out of her ass before plunging back into her, her walls now used to the way I manipulated and opened her up. A couple more hard thrusts and I was about ready to spill, the force growing in my loins to an almost unbearable pressure. Try as I might to breathe through it and calm the oncoming storm, I couldn’t stop the build up from ramping up to its climax.

“Get onto your knees.” I barked, my words shaking as I struggled to talk between each gasp. 

Doing as she was told, she eased herself off of my cock, my shaft now slick from my spittle and her tight, wet ass. My cock throbbing in my hand, I tried to control myself long enough to allow her to get on her knees. 

Once she was down, she opened her mouth and stuck her tongue out waiting for my load. I spurted all over her face, my cum splattering against her chin and cheeks, some of the streams lashing her tongue in heavy spurts. Obediently, she sat and took it all, patiently waiting for me to relieve myself before she started to lick up the mess. For the bits she couldn’t reach with her tongue, she used her fingers to scoop up the fluid, before greedily sucking it from her digits. 

Given my inexperience in such situations, I expected it to end there, but to my surprise she edged closer to my cock, her lips inches from my still wet tip. Although I’d emptied myself, my hardness remained, the way she riled me proven by how I was able to remain erect and ready for more. 

“I think I should clean this up for you.” She suggested, just as she lowered her mouth and started to work me all over again. It was, and still is, no word of a lie to say she’s truly a different kind of girl to the ones I’ve known before.

More like this

Discovering New Depths
Choose character of story:
Discovering New Depths Discovering New Depths
Discovering New Depths Discovering New Depths

SHE.
Choose character of story:
SHE. SHE.
SHE. SHE.

Bro’ Code
Choose character of story:
Bro’ Code Bro’ Code
Bro’ Code Bro’ Code

Uncharted Waters
Choose character of story:
Uncharted Waters Uncharted Waters
Uncharted Waters Uncharted Waters

My Best Kept Secret
Choose character of story:
My Best Kept Secret My Best Kept Secret
My Best Kept Secret My Best Kept Secret

Mirror
Choose character of story:
Mirror Mirror
Mirror Mirror

More Than Roommates
Choose character of story:
More Than Roommates More Than Roommates
More Than Roommates More Than Roommates

Coming Clean
Choose character of story:
Coming Clean Coming Clean
Coming Clean Coming Clean