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Finding Dana

It would always happen, without fail. I'd begin jacking off to regular, everyday porn, like everyone else. A man doing a woman, maybe two. Sometimes two women. Sometimes a woman on her own. But it never ended with that. The same thing would always happen — I would only come from watching a transgender girl.

On the porn sites, they called them "Shemales." I never knew why that was, but I figured there was a reason, and I went with it. I'd watch two of them fuck, or a shemale and a man, or sometimes just a shemale by herself. Nothing else could get me off.

It was their cocks that did it. Every time, I would find myself starting at her face, or her tits, or sometimes her feet — as I did have a slight foot fetish. But no matter what, my eyes drifted to the cock.

Sometimes I would try to see if it was cocks I was into, and I'd watch videos of men jacking themselves off, or even legit gay porn. I liked it, but always wound up back on the same category, watching the shemales.

It was destined to be a fantasy for me, as I didn't even know any transgender girls. It would have to live in the online realm for now.

Being invited to a wedding for someone you only casually know from work is a mixed blessing. Sure you're getting some free food and drinks, but you're probably going to be bored from not knowing anyone. So when I got an invitation to my coworker's wedding, I prepared myself for the inevitable.

Of course, I was seated at the Singles Table for the reception, banished to the land of hopefuls and the lonely. I decided I'd just enjoy the food, and politely leave after the dessert. That was until I saw her sit down across from me.

She had flowing dirty blonde hair, and wore the winged eyeliner like so many girls do now. Her strapless dress showed just enough of her ample tits to catch your eye, but not enough to be slutty. The slit in her dress came up high enough to show her slender legs, and even higher so that your imagination begged for more.

And what's more, she was smiling at me.

Eventually, a moment happened where it was just us at the table. I found the courage to move to her side of the table and sit down next to her. Her perfume faintly breezed through the air around her.

"I'm Chad." I told her.

"Hi, I'm Dana." She replied, with a small giggle. "I'm glad you sat down."

On cue, the servers refilled the wine glasses, and we each took a long, courage building gulp. With the ice broken, we were able to chat. Well, she was anyway.

During the normal "what do you do where are you from" chit chat, I couldn't stop looking her over. Something was begging me to look closer at her, and I wasn't sure why. She was different, somehow. Mysterious.

When the DJ shifted to a slow ballad, the dance floor began coupling up. It was the opening I needed.

"Would you like to dance?" I asked her. "I kind of feel like we haven't done our duty unless we dance at least one song."

"Well, if it's for the cause... I suppose I could." She smiled and winked, letting me know she was just messing with me.

I took Dana's hand, and led her to the floor. Careful not to overstep my boundaries, I assumed an older fashioned dance pose, with a hand out to the side. Dana bypassed that, opting to place both hands around my neck, moving in close. It was perfect.

We moved a bit with her head on my shoulder. Her perfume and hair was doing something amazing to me, until I felt it. At first I thought it was my phone in my pocket, or something shifting. I felt something move down there, and I knew it wasn't attached to me. It was..

My lord, it was her cock.

I immediately moved back and looked her in her face. She had an expression that was fear, embarrassment, shame, and terror all mixed into one. I could feel her heart pounding out of her chest. I had to let her know this wasn't just a good thing — it was a great thing.

My hands already on her waist, I did the logical thing. I pulled her closer.

When she felt that, I saw a smile break on her face. Simultaneously, the excitement of the surprise had left my own cock in the process of swelling up in anticipation. I knew she felt it, because she whispered to me "Oh, really?"

Unfortunately, the song had ended. This left both of us in the predicament of having to walk back to the table with erections while a banquet hall of people stared. Acting in the clutch, I took my suit coat off, pretending to be hot. I draped it over my arm, held it over my rock hard boner, and proceeded to walk in front of Dana to our table.

It was the longest seven yard walk of my life.

Back at the table, we looked at each other briefly. Without a word being said, we both collected our belongings and walked to the exit.

Dana opened her phone and proceeded to use her app to summon a ride. "Don't bother." She said, "We're going to my place."

On the cab ride over, I couldn't help myself. I leaned over and kissed her with everything I had. Our lips locked, she rubbed her hand up my thigh, into my lap, and started massaging my hard cock. We didn't care about the driver, there was just no time for that.

Upon arriving, she led me up the single flight of stairs with a sense of urgency like I'd never seen. Her party dress flowing back and forth, I did my best to keep up.

Her apartment was a pretty standard single woman's place. Decorated a certain way, with a certain scent of candle in the background.

I had no time to enjoy the scenery. Dana pulled me in close, and kissed me with her entire body. Her tits pressed against my chest, and her hand kept rubbing my cock. I kept kissing her until I remembered — her cock.

Other than my own, no cock had ever touched my hands. I'd never felt one, yet I'd seen so many of them in porn videos. I knew what to do, I just needed to do it. I needed to live out what I'd always dreamt of feeling. I had to hold her cock in my hand.

Moving over her dress, I shyly pressed my hand into the growing bulge beneath her dress. It felt familiar, yet new. It was like mine, but was hers. Hard, warm, and begging for attention. I squeezed just a little, and she let out a moan from the bottom of her lungs as if she'd never felt anything so good.

So I kept going.

I rubbed her cock through her dress, massaging it, enjoying the new sensations. I finally got bold enough to reach through the slit on her dress and rub her cock through her soft, lacy, cotton panties. She quivered, but pulled me in tighter.


"Don't stop." She whispered.

"Never." I moaned.

Rubbing her pulsing cock was getting me hotter than anything I'd ever known. She must have felt the same, because her dress somehow came right off, and she stood in front of me in nothing but pink panties, and high heel shoes. My pants and dress shirt followed immediately.

She got me into her bedroom and we immediately laid on the bed, continuing our passionate kisses and rubbing each other's cocks. As if on autopilot, my hand reached inside of her panties, and moved about until I felt it.

I had a cock in my hand. A beautiful, warm, fleshy cock. It was everything I wanted.

Laying there, I started stroking her cock. Up and down, slowly at first. I held my hand tighter, like I had on my own, and started jerking her off faster. She quivered, arched her back, and kept saying "More... more" over and over. I slid her panties off so I could stroke all of it.

Looking at her giant, smooth cock, I knew I needed to suck it.

Rolling her to her back, I moved down and took her massive cock in my mouth like I'd seen in movies, and began wrapping my tongue around the head. It was slippery from her precum, and I lapped up the savory fluids.

Her cock was amazing in my mouth. The taste, the feel, all of it. I sucked her off with every last inch of my mouth. I was actually impressed at how natural I was at it. It all felt natural. All of it. Her giant, fleshy rod in my mouth, my tongue licking all of it — this was more than I dreamed.

I could feel the swelling happening. I knew what this meant, because it happened to me.

She was moaning furiously. I looked up with her cock in my mouth, she looked back at me, unable to contain herself.

"I... I... I'm going to come." she moaned. "I want to come in your mouth."

My mouth full of her cock, I nodded best I could and moaned what I hoped she knew was a yes. I sped up my mouth, sucked as hard as I could, until I felt it happen. Her cock swelled up, her moans got louder, and her hips bucked.

"I'm... omigod... I'm gonna come." she yelled.

Her cock exploded in my mouth. My first taste of cum washed over my tongue like a wave. Hot juices filled my mouth as she shot her entire load in me. I savored the taste for a moment, and then gulped every bit of her down my throat. I had her cum in me.

After I licked her cock clean, she immediately got up on hands and knees, facing her round ass in my direction.

"Now." she stammered. "Fuck me now."

I did as I was told, and pushed my hard cock into her ass. She shook violently when it entered her, then pulled on my hips to get me in deeper. Her asshole was like nothing my cock ever felt. It was tight and warm, but softer than any pussy I'd ever felt.

It must have been a little too good, because I felt my own cock stiffen. I was about to blow my load in Dana's ass.

"I think I'm gonna..." I started.

"Yes!" she cut me off. "Please come in my ass, darling. Right now."

I had no powers of control at that point and I allowed all of my semen to explode inside of her. I must have shot three times my normal size load inside of her. I kept filling all of her ass with my semen. So much that it leaked out the back.

We collapsed in a heap, and laid in the bed staring at each other. I had done it. I had fucked a shemale, like I'd wished for. And I couldn't wait to do it again.It would always happen, without fail. I'd begin jacking off to regular, everyday porn, like everyone else. A man doing a woman, maybe two. Sometimes two women. Sometimes a woman on her own. But it never ended with that. The same thing would always happen — I would only come from watching a transgender girl.

On the porn sites, they called them "Shemales." I never knew why that was, but I figured there was a reason, and I went with it. I'd watch two of them fuck, or a shemale and a man, or sometimes just a shemale by herself. Nothing else could get me off.

It was their cocks that did it. Every time, I would find myself starting at her face, or her tits, or sometimes her feet — as I did have a slight foot fetish. But no matter what, my eyes drifted to the cock.

Sometimes I would try to see if it was cocks I was into, and I'd watch videos of men jacking themselves off, or even legit gay porn. I liked it, but always wound up back on the same category, watching the shemales.

It was destined to be a fantasy for me, as I didn't even know any transgender girls. It would have to live in the online realm for now.

Being invited to a wedding for someone you only casually know from work is a mixed blessing. Sure you're getting some free food and drinks, but you're probably going to be bored from not knowing anyone. So when I got an invitation to my coworker's wedding, I prepared myself for the inevitable.

Of course, I was seated at the Singles Table for the reception, banished to the land of hopefuls and the lonely. I decided I'd just enjoy the food, and politely leave after the dessert. That was until I saw her sit down across from me.

She had flowing dirty blonde hair, and wore the winged eyeliner like so many girls do now. Her strapless dress showed just enough of her ample tits to catch your eye, but not enough to be slutty. The slit in her dress came up high enough to show her slender legs, and even higher so that your imagination begged for more.

And what's more, she was smiling at me.

Eventually, a moment happened where it was just us at the table. I found the courage to move to her side of the table and sit down next to her. Her perfume faintly breezed through the air around her.

"I'm Chad." I told her.

"Hi, I'm Dana." She replied, with a small giggle. "I'm glad you sat down."

On cue, the servers refilled the wine glasses, and we each took a long, courage building gulp. With the ice broken, we were able to chat. Well, she was anyway.

During the normal "what do you do where are you from" chit chat, I couldn't stop looking her over. Something was begging me to look closer at her, and I wasn't sure why. She was different, somehow. Mysterious.

When the DJ shifted to a slow ballad, the dance floor began coupling up. It was the opening I needed.

"Would you like to dance?" I asked her. "I kind of feel like we haven't done our duty unless we dance at least one song."

"Well, if it's for the cause... I suppose I could." She smiled and winked, letting me know she was just messing with me.

I took Dana's hand, and led her to the floor. Careful not to overstep my boundaries, I assumed an older fashioned dance pose, with a hand out to the side. Dana bypassed that, opting to place both hands around my neck, moving in close. It was perfect.

We moved a bit with her head on my shoulder. Her perfume and hair was doing something amazing to me, until I felt it. At first I thought it was my phone in my pocket, or something shifting. I felt something move down there, and I knew it wasn't attached to me. It was..

My lord, it was her cock.

I immediately moved back and looked her in her face. She had an expression that was fear, embarrassment, shame, and terror all mixed into one. I could feel her heart pounding out of her chest. I had to let her know this wasn't just a good thing — it was a great thing.

My hands already on her waist, I did the logical thing. I pulled her closer.

When she felt that, I saw a smile break on her face. Simultaneously, the excitement of the surprise had left my own cock in the process of swelling up in anticipation. I knew she felt it, because she whispered to me "Oh, really?"

Unfortunately, the song had ended. This left both of us in the predicament of having to walk back to the table with erections while a banquet hall of people stared. Acting in the clutch, I took my suit coat off, pretending to be hot. I draped it over my arm, held it over my rock hard boner, and proceeded to walk in front of Dana to our table.

It was the longest seven yard walk of my life.

Back at the table, we looked at each other briefly. Without a word being said, we both collected our belongings and walked to the exit.

Dana opened her phone and proceeded to use her app to summon a ride. "Don't bother." She said, "We're going to my place."

On the cab ride over, I couldn't help myself. I leaned over and kissed her with everything I had. Our lips locked, she rubbed her hand up my thigh, into my lap, and started massaging my hard cock. We didn't care about the driver, there was just no time for that.

Upon arriving, she led me up the single flight of stairs with a sense of urgency like I'd never seen. Her party dress flowing back and forth, I did my best to keep up.

Her apartment was a pretty standard single woman's place. Decorated a certain way, with a certain scent of candle in the background.

I had no time to enjoy the scenery. Dana pulled me in close, and kissed me with her entire body. Her tits pressed against my chest, and her hand kept rubbing my cock. I kept kissing her until I remembered — her cock.

Other than my own, no cock had ever touched my hands. I'd never felt one, yet I'd seen so many of them in porn videos. I knew what to do, I just needed to do it. I needed to live out what I'd always dreamt of feeling. I had to hold her cock in my hand.

Moving over her dress, I shyly pressed my hand into the growing bulge beneath her dress. It felt familiar, yet new. It was like mine, but was hers. Hard, warm, and begging for attention. I squeezed just a little, and she let out a moan from the bottom of her lungs as if she'd never felt anything so good.

So I kept going.

I rubbed her cock through her dress, massaging it, enjoying the new sensations. I finally got bold enough to reach through the slit on her dress and rub her cock through her soft, lacy, cotton panties. She quivered, but pulled me in tighter.


"Don't stop." She whispered.

"Never." I moaned.

Rubbing her pulsing cock was getting me hotter than anything I'd ever known. She must have felt the same, because her dress somehow came right off, and she stood in front of me in nothing but pink panties, and high heel shoes. My pants and dress shirt followed immediately.

She got me into her bedroom and we immediately laid on the bed, continuing our passionate kisses and rubbing each other's cocks. As if on autopilot, my hand reached inside of her panties, and moved about until I felt it.

I had a cock in my hand. A beautiful, warm, fleshy cock. It was everything I wanted.

Laying there, I started stroking her cock. Up and down, slowly at first. I held my hand tighter, like I had on my own, and started jerking her off faster. She quivered, arched her back, and kept saying "More... more" over and over. I slid her panties off so I could stroke all of it.

Looking at her giant, smooth cock, I knew I needed to suck it.

Rolling her to her back, I moved down and took her massive cock in my mouth like I'd seen in movies, and began wrapping my tongue around the head. It was slippery from her precum, and I lapped up the savory fluids.

Her cock was amazing in my mouth. The taste, the feel, all of it. I sucked her off with every last inch of my mouth. I was actually impressed at how natural I was at it. It all felt natural. All of it. Her giant, fleshy rod in my mouth, my tongue licking all of it — this was more than I dreamed.

I could feel the swelling happening. I knew what this meant, because it happened to me.

She was moaning furiously. I looked up with her cock in my mouth, she looked back at me, unable to contain herself.

"I... I... I'm going to come." she moaned. "I want to come in your mouth."

My mouth full of her cock, I nodded best I could and moaned what I hoped she knew was a yes. I sped up my mouth, sucked as hard as I could, until I felt it happen. Her cock swelled up, her moans got louder, and her hips bucked.

"I'm... omigod... I'm gonna come." she yelled.

Her cock exploded in my mouth. My first taste of cum washed over my tongue like a wave. Hot juices filled my mouth as she shot her entire load in me. I savored the taste for a moment, and then gulped every bit of her down my throat. I had her cum in me.

After I licked her cock clean, she immediately got up on hands and knees, facing her round ass in my direction.

"Now." she stammered. "Fuck me now."

I did as I was told, and pushed my hard cock into her ass. She shook violently when it entered her, then pulled on my hips to get me in deeper. Her asshole was like nothing my cock ever felt. It was tight and warm, but softer than any pussy I'd ever felt.

It must have been a little too good, because I felt my own cock stiffen. I was about to blow my load in Dana's ass.

"I think I'm gonna..." I started.

"Yes!" she cut me off. "Please come in my ass, darling. Right now."

I had no powers of control at that point and I allowed all of my semen to explode inside of her. I must have shot three times my normal size load inside of her. I kept filling all of her ass with my semen. So much that it leaked out the back.

We collapsed in a heap, and laid in the bed staring at each other. I had done it. I had fucked a shemale, like I'd wished for. And I couldn't wait to do it again.

finding   dana  

Aug 25, 2018 in anal

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