David and Sarah
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Becoming Sarah free porn video
I was driving home from a work trip. That is how it started.
There was roughly 85 miles to home. I had been driving for about an hour when my mind began wandering the way it always does when I'm not preoccupied. It always goes to the same place. For the better part of five years, I have been cross-dressing in secret whenever I have the house to myself.
Sometimes I do it because it excites me sexually, and sometimes I do it just because it feels right. The way silky panties slide around on soft skin, the way a bra can hold you just right, the way a dress can flatter all the right curves and make you feel sexy and beautiful: these are the things I love most about it.
But, more recently, a curiosity had gotten the better of me. I had always considered myself to be heterosexual but, when I dressed, an inner femininity had been coming to the surface. When I found myself standing in the kitchen fully en-femme, I had started yearning for the sensation of a man to come from behind and wrap his arms around me, slowly kissing my neck and squeezing my round, waiting bottom.
I hadn't acted on these feelings yet. I wasn't sure that I ever could. But, when I was dressed and alone and had that needy, wanting feeling arise, I wanted to be held, be squeezed, be protected, and be loved. I had started to explore these feminine urges myself. Instead of just pulling out my cock and going to work, I found myself slowly letting my hands explore my body. I would feel the subtle contours and distinct textures of the lacy panties and the tension of the bra straps as I slipped them off my shoulder and caressed my nipples.
Just a week ago, for the first time, I had found myself putting a finger in my ass while imagining a man hovering over me. It felt wonderful and left me with a burning curiosity for more. All these thoughts were racing through my mind as my car hurdled down the never-ending highway. I knew that I wanted to take the next step, but I wasn't sure what exactly that would be.
Even though I was in full guy-mode in my car. My inner girl was rising to the surface as these feminine thoughts plowed through all the open spaces of my mind. I was contemplating the next steps.
Should I put an add online to meet a guy? No. Too risky.
Should I make a trip to the local gay bar? No. I might see someone I know there and I wouldn't want this getting back to my wife.
Hell, how could I even pull up the courage to meet a men dressed? I didn't even know if I could handle a man. I had only ever fit one finger inside myself and that was just about all I could take. Then, inspiration struck. I saw a billboard for a 24/7 adult novelty store.
“That's it!” I thought to myself.
The next step would be buying a sex toy to explore myself further, to see if I had what it took to be a girl and accept the willing cock of an eager man.
I took the exit and turned right as instructed. In fact, I imagined that there was a strong, confident man beside me telling me where to go. I saw the building and pulled into the parking lot. My hands began to shake. You see, I tend to get kind of nervous. I explored all of these feelings in secret, and I didn't want any chance that anyone I knew saw me in there. But, after a few long, deep breaths, I opened the car door and began walking into the store.
Luckily, upon my entrance into this establishment, I noticed that I was alone. Well, alone except for the clerk behind the counter. He was a sort of geeky looking guy. He was mid-thirties, average build, thick black-rimmed glasses. He looked like a computer guy, a gamer. He was silent as I walked in, as I guess is customary in this sort of place. I wouldn't know. I had never been in one before.
I started by walking through the DVD aisles as I tried to build the courage to walk over to what I really wanted. There was a large assortment of female sex aids lining the back of the store. I kept glancing over and then returning my gaze to the movies before this stranger would catch me looking. Crazy? I know. If I could find the courage to buy one of these sex toys, this would be the guy checking me out, so why should I be bashful now? But, alas, here I was walking up and down the movie aisle trying to be stealthy.
Just as I was feeling my courage fade and about to leave the store empty-handed and disappointed, my eyes drifted to a movie on the bottom row. I knelt down and examined it. Staring back at me were the gorgeous, dark-mascara eyes of a trans girl. She was wearing a slinky black dress, standing proudly with a finger pulling gently at her lower lip and the little tip of her sissy cock hanging from the bottom of the dress. I turned the movie over and the back cover was a picture of her naked on all fours with muscle-bound man standing behind her and penetrating her with his thick cock.
Her face in that picture is what sold me. She looked so euphoric. I knew that this girl must have, at one point, felt the exact same way as me: just starting to explore her feminine side and knowing that she needed a man to make her truly feel as girly as she could be. If I was ever to experience the pure feminine pleasure she was, I needed to go and pick out my dildo and begin my journey.
I put the movie back and walked to the aisle. I started giggling on the inside, feeling like a little slut in a candy store. Which one of these silicone penises would take my virginity? This must be what girls felt like all the time. As a man, all of the hard work that goes into trying to get a girl to sleep with you can be exhausting. I kept thinking how nice it must be to be a pretty girl and have all the men hit on you, and you being able decide whom you will let inside.
After some serious thought, I picked out the most lifelike one I could find. I figured that if I was truly training myself to one day take a real man, I might as well work with the most real trainer. I made sure that it had a suction cup on it so that I could affix it to my wall and fuck myself doggy style like I always am being fucked in my fantasies.
Even though my outside was still dressed as a man, at this point my inner self was completely girl. Sarah is what I called her. I was all Sarah now.
I tried to make my hips swivel as I walked to the counter, getting in a little wiggle practice. Although, no matter how hard I tried, I could never get quite the same sway as a real girl.
I put my new toy on the counter and began to reach for my wallet.
"34 dollars," said the clerk.
Without a word, I pulled the cash out of my wallet and handed it to the man. He took my money, made the change, and put his hand out. I put my hand under his waiting for him to drop the coins in my palm, but he hesitated. A sort of awkward moment ensued, and then he spoke.
"What are you into?" he said.
My face flushed red and my heart started pounding. I didn't know what to say. I obviously was a guy buying a dildo, what more did he want? I’m sure he saw my cheeks flush.
"You don't have to tell me if you don't want to. I was just curious," he said in a very calming way.
His eyes locked onto mine and, oddly enough, I began to feel a calming wave wash over me. I could sense that this guy wasn't looking to harm me in any way. He was here to protect me. Feeling safe, Sarah came rushing back to the surface. I tilted my head down just a bit so that I could look at him with a little puppy-dog pout.
"Actually, I'm a sissy," I said.
And immediately after saying it, I felt a thousand pound weight lifted off my shoulders. This was the first time I had ever confided this to another human being. But, the way his eyes were still locked onto mine, I couldn't lie to him.
"You don't look like one," he said.
This immediately crushed me and he could tell.
"No, no, no. Don't feel bad. I just mean, you’re wearing boys clothes. Do you have anything in your car you could wear?" he asked.
I didn't. But now my mind was racing in a hundred different directions. Why did he ask me that? Does he want to see me dress up? Is he hitting on me? My heart began racing again, but in a good way this time. What was this new feeling? A new tingling sensation I had never felt before began working its way through my veins.
"I don't, unfortunately," I said in my cutest little whimper voice.
He dropped the change in my hand and immediately cupped it in a warm, gentle embrace.
"What is your name?" he asked.
I let a little coy smile out and replied, "I'm Sarah. What's your name?"
"I'm Matt," he answered.
Another little pause occurred, and then he stroked the outside of my wrist with his finger.
"Sarah, I want you to go walk down that hallway and go into the second room on the left. Would you do that for me?" he asked.
At this point, on any other day, with any other man, I would have taken off running. But, for some reason, maybe it was this new tingling in my veins, maybe it was the fact that my head began to swim and swoon, I just nodded and began to walk toward the hallway.
I had a feeling that Matt would be watching, so I tried to put on my best wiggle-strut for him. The whole time I wished I get it down pat. I couldn't quite figure out exactly how to get my hips to sway the right way yet.
I opened the door and, before I walked in, I looked back at Matt. He had the most handsome grin on and gave me a little wink. I walked in and shut the door behind me.
The room was dimly lit. There was a little bench and some hooks on the wall. This was a dressing room, but larger in size than the ones typically found in a department store. I sat in the room for what seemed like an age. I had no idea what I was doing and what I was in for. All I knew is that I wanted to make Matt happy, whatever that meant. After a few minutes there was a knock at the door.
"Sarah?" said Matt.
"Yes, Matt," I sort of nervously giggled.
"Take your clothes off," he said firmly.
My knees immediately began to shake. My palms got sweaty. I felt like I could faint any second, but Matt's voice telling me what to do made it seem okay.
"Tell me when you’re done," he said.
I took my shirt, pants, and underwear off. I was now standing in this dressing room completely naked and unsure about exactly what was happening.
"I'm done," I replied.
"Good," he said.
The door creaked open just a slit, but Matt did not come in, nor did he peek inside. He tossed in a few articles of clothing that I couldn't quite make out in the dim light and shut the door again.
"Put these on and hang tight, Sarah. A customer just came in. I'll be back in a second," he reassured me.
I walked over and discovered he had tossed in the cutest little pair of black lace bikini cut panties with matching garter belt; sheer, knee-high black stockings; and padded, black push-up bra. With my shaking hands, I picked up the panties and put my legs through one-by-one. When I pulled them up to my thighs, I stopped and took a second to push my testicles up and tuck my cock back, then pulled the panties all the way up so that I had the flat front of a real girl.
I then sat down on the bench and put on the stockings, slowly pulling them up over my knees until they rested on my thighs. Next, the garter belt came up; I pulled the straps down and clipped them to my stockings. Finally, I snapped the bra on. Matt guessed exactly right on my cup size. Being ever so slightly chubby, what little natural breasts I had were pushed up and gave the appearance of perky B cup breasts spilling ever-so-intoxicatingly over the bra line.
I looked in the mirror on the wall and was unbelievably happy. That ‘feeling-so-right’ I got when I dressed at home returned. I was admiring my body in the mirror and how feminine it looked when there was a gentle knock at the door.
"Almost forgot something," Matt said.
The door opened just a slit again and a wig and some basic make-up came in. I wasn't the best with my make-up yet, but I did the best I could. Foundation, blush, eye-shadow, lid-liner, lipstick. When I was finished applying them to the best of my ability, I put on the wig. Matt had given me a dark auburn, long wavy-haired wig.
I put it on my head and swung it back to give it a natural look. When I met my own reflection in the mirror, I was floored. I looked hot. Matt had picked out all of the right sizes for my body and all the right colors for my complexion. This was by far the most beautiful I had ever looked. I was ecstatic.
Then, suddenly, the doorknob to the dressing room started turning. My heart began fluttering uncontrollably, but then Matt's voice came through and soothed my nerves.
"Sarah, baby. Are you all dressed? Can I come in?" he asked.
I took just a second to let my brain register what had happened in the last half hour. Just 30 minutes ago, I was a man driving home from a business trip, and now I had become Sarah, standing vulnerable in erotic lingerie in a dressing room in some hole-in-the-wall sex shop in God-Knows-Where. But, by this point, I was transfixed by Matt.
I looked at myself in the mirror once more, at all of the exquisitely selected items he had chosen for me. He seemed to know me better than I knew myself. After the roller-coaster of emotions of the past half-hour, the only one that was left was a desire to please this man who had been so kind to me.
"I'm ready," I said, "you can come in."
I was nervous again, not for any reason of my own, but because I wanted Matt to approve of me. I wanted him to like me in these clothes he had picked out just especially for me.
He came in, and for the very first time, I saw the look of lust in a man's eye while he stared at me. He clearly liked what he saw. I could see his pupils dilate and watched the throbbing pulse of the artery in his neck quicken.
"You look incredible, Sarah," he said as he walked closer to me.
He stopped just in front of me. We were separated by no more than an inch when he put his hands on my hips and leaned in to kiss me. I titled my head back and accepted his embrace. His lips were on mine and I opened my mouth a little wider. I wanted his tongue to wrap around mine. He obliged and our tongues began dancing around each other.
I felt like I was floating. His hands were on my hips but they were now wrapping around the back of me and he began to squeeze my ass. I could feel every ounce of myself being given over to him. My body was now his for the taking. He could use me in whatever way he wanted. All he had to do was direct me to his every whim.
He pulled me closer and his mouth began wandering to the side of my head. I could feel his hot breath in my ear.
"Sarah, be honest with me. Have you done this before?" he whispered.
Although I wanted to tell him no, that I had no worries, I couldn't lie to him.
"I've never been with a man before," I answered.
I could feel his grip on my ass become a little gentler. I knew I was in good hands.
"Then I'll take it slow for you, baby," he said.
I melted in his arms. We stood there kissing for a few minutes, his hands slowly moving from my ass to hips, down to my thighs, back up to the back of my head, pushing my mouth into his. Then, I could feel his palm on my shoulder and a gentle push down.
This was it. No going back now. I knew what this gesture meant; I had used it many times before on the various women I was with. But, this time, being on the opposite end, it felt better than it ever had before. I knew what he wanted, and I wanted to please him.
I got down on my knees and, for the first time, began rubbing a man's cock through his jeans. It was already semi-hard from our making out, but as I caressed it I could feel it growing even more. I undid his belt, unbuttoned his jeans, and slid them down.
Now the only thing left between my face and his hard cock was a thin layer of underwear. I pulled those down and saw the thing that I had been dreaming about for months. Matt's hard cock was staring me right in the face. I put my hands on it and was surprised by the texture. I had felt my own cock countless times, but it felt so much different to be holding this one. I could feel it pulsing.
As I paused for one last second, a shadow of a doubt crept in. I somehow knew that once I put this cock in my mouth there would be no letting go of Sarah. But, when I looked up at Matt's face and saw the expression of pleasure I had sought to bring out, I wrapped my lips around the end of his hard cock.
I worked my tongue around the head as I slipped my lips up and down the shaft. I couldn't believe how good it felt! I could feel every ounce of masculinity slide off and was overcome with feminine joy. I was working this cock and it felt incredible. Matt was moaning and I knew that my mouth was bringing him so much pleasure. It was euphoric.
I sucked Matt's cock for about ten minutes before I tasted my first bit of salty pre-cum. He put his right hand under my chin and gently pulled me back up. He put his tongue deep inside my mouth, where his cock had just been, and he pushed me against the wall. I had clearly awoken something with him. He was consumed with desire, a desire for me. His hands moved all over my body and I knew that he wanted to fuck me.
He spun me around. I put my hands up against the wall. He began kissing his way down my back and his hands were stroking my inner thighs. I could feel wave after wave of ecstasy over come me. I could tell my body was getting ready. I could actually feel myself giving way in anticipation.
His hands pulled away for a second and I could here a bottle click open and something squirt out. Matt put his mouth on my ear and began whispering just as finger found its way past the side of panties and began gently rubbing a warming gel on my asshole.
"Baby, I know this is your first time, so I'm going to go slow. I need you to relax. Can you do that for me?" he asked.
"Yes, I can. I want you, Matt. I want you to fuck me," I moaned.
The tip of his finger was slowly pushing into me and it felt a thousand times better then when I had done this to myself back at home. Another finger found its way to mouth and I began to suck on it as if it was his cock.
He spun me back around and we kissed for several more minutes. He knew I needed to fully relax. The warming gel was working wonders and I could feel a heat begin to radiate inside me.
"It's time," he said.
He gently turned me around and put his hands on my hips pulling me down to my knees. His chest pressed against my back and his weight guided me down to my hands. I looked in the mirror to my right and saw myself on all fours in front of this man. My legs were spread apart and he was on his knees between them.
I recognized the look on my face. It was the same look that the girl on the movie cover had. I was about to experience the true feminine ecstasy that can only happen when being taken by a man.
Matt pulled the back of my panties down. His hands rested firmly on my hips as his cock eased its way between by butt-cheeks. He stopped when his head touched my whole. He slowly started pushing.
"Just relax, Sarah. You look so fucking hot right now. I'm not sure how long I'll last fucking a girl as beautiful as you," he assured me.
Again, the exact right words I needed to hear. My ass opened up, as if by command on those words, and I could feel all of his seven inches rush inside me. There was a sharp pain. I had never had more than a finger inside me and now I had a fully erect cock! I never even got to try the dildo I came here to buy!
Our bodies rocked back in forth in synced rhythm. The pain I felt slowly gave way to ecstasy. This man was using me for his pleasure and I couldn't be happier about it. He pumped in and out of my ass, over and over and over again. His hands firmly grasped my hips and he used his muscles to pull back my gaping asshole on top of him. I let out moans of pleasure as his cock rammed in and out of my ass.
I glanced back to the mirror and watched my man fuck me. There was no man staring back, however. I saw Sarah, fully and truly. Matt had taken every last drop of masculinity and fucked it right out of me.
Suddenly his pace quickened. His hands squeezed my ass cheeks unbearably tight and he gave one last, deep thrust. I felt his hot cum shoot deep inside me. I was overcome with emotion. I now had the essence of this man inside me, and I couldn't be happier about it.
He held is cock inside me for a few moments as he leaned over top of me and pulled my head sideways and back. He kissed me again as I felt is cock go limp. He pulled up the back of my panties and returned me to a standing position. I could barely keep any balance. My freshly fucked body was still wobbly and weak. Matt leaned into me for one long last kiss.
"My God, Sarah. You were absolutely amazing," he gasped.
Every ounce of my being was satisfied knowing I had let Matt use me for his pleasure.
"You have to get going now before my replacement comes. But, please keep these things on," he motioned to my lingerie, "I want to know that you'll be wearing these as you drive away."
Matt pulled up his pants and walked out of the room. I put my boy clothes on overtop of my lacy undergarments as he instructed. I took a moment to reflect on everything that had just happened and a beaming smile came upon my face. I walked out of the dressing room and Matt was behind the counter again.
"Bye, for now, Sarah. I really hope you find your way back here again," Matt said with a grin.
"I'm sure I will," I said through my gaping smile.
As I walked out of the shop I noticed something amazing. My hips were swaying with every step effortlessly. My ass was wiggling and bouncing with every step like so many girls I had seen before. I knew that I had just been forever changed!
I got in my car and turned on the ignition. As I began driving back down the highway, I could still feel Matt inside me. His cum was slowly working its way out of my ass and pooling in my panties. Sarah had been freed. I was already counting the minutes until I could return back into Matt's arms.
There was roughly 85 miles to home. I had been driving for about an hour when my mind began wandering the way it always does when I'm not preoccupied. It always goes to the same place. For the better part of five years, I have been cross-dressing in secret whenever I have the house to myself.
Sometimes I do it because it excites me sexually, and sometimes I do it just because it feels right. The way silky panties slide around on soft skin, the way a bra can hold you just right, the way a dress can flatter all the right curves and make you feel sexy and beautiful: these are the things I love most about it.
But, more recently, a curiosity had gotten the better of me. I had always considered myself to be heterosexual but, when I dressed, an inner femininity had been coming to the surface. When I found myself standing in the kitchen fully en-femme, I had started yearning for the sensation of a man to come from behind and wrap his arms around me, slowly kissing my neck and squeezing my round, waiting bottom.
I hadn't acted on these feelings yet. I wasn't sure that I ever could. But, when I was dressed and alone and had that needy, wanting feeling arise, I wanted to be held, be squeezed, be protected, and be loved. I had started to explore these feminine urges myself. Instead of just pulling out my cock and going to work, I found myself slowly letting my hands explore my body. I would feel the subtle contours and distinct textures of the lacy panties and the tension of the bra straps as I slipped them off my shoulder and caressed my nipples.
Just a week ago, for the first time, I had found myself putting a finger in my ass while imagining a man hovering over me. It felt wonderful and left me with a burning curiosity for more. All these thoughts were racing through my mind as my car hurdled down the never-ending highway. I knew that I wanted to take the next step, but I wasn't sure what exactly that would be.
Even though I was in full guy-mode in my car. My inner girl was rising to the surface as these feminine thoughts plowed through all the open spaces of my mind. I was contemplating the next steps.
Should I put an add online to meet a guy? No. Too risky.
Should I make a trip to the local gay bar? No. I might see someone I know there and I wouldn't want this getting back to my wife.
Hell, how could I even pull up the courage to meet a men dressed? I didn't even know if I could handle a man. I had only ever fit one finger inside myself and that was just about all I could take. Then, inspiration struck. I saw a billboard for a 24/7 adult novelty store.
“That's it!” I thought to myself.
The next step would be buying a sex toy to explore myself further, to see if I had what it took to be a girl and accept the willing cock of an eager man.
I took the exit and turned right as instructed. In fact, I imagined that there was a strong, confident man beside me telling me where to go. I saw the building and pulled into the parking lot. My hands began to shake. You see, I tend to get kind of nervous. I explored all of these feelings in secret, and I didn't want any chance that anyone I knew saw me in there. But, after a few long, deep breaths, I opened the car door and began walking into the store.
Luckily, upon my entrance into this establishment, I noticed that I was alone. Well, alone except for the clerk behind the counter. He was a sort of geeky looking guy. He was mid-thirties, average build, thick black-rimmed glasses. He looked like a computer guy, a gamer. He was silent as I walked in, as I guess is customary in this sort of place. I wouldn't know. I had never been in one before.
I started by walking through the DVD aisles as I tried to build the courage to walk over to what I really wanted. There was a large assortment of female sex aids lining the back of the store. I kept glancing over and then returning my gaze to the movies before this stranger would catch me looking. Crazy? I know. If I could find the courage to buy one of these sex toys, this would be the guy checking me out, so why should I be bashful now? But, alas, here I was walking up and down the movie aisle trying to be stealthy.
Just as I was feeling my courage fade and about to leave the store empty-handed and disappointed, my eyes drifted to a movie on the bottom row. I knelt down and examined it. Staring back at me were the gorgeous, dark-mascara eyes of a trans girl. She was wearing a slinky black dress, standing proudly with a finger pulling gently at her lower lip and the little tip of her sissy cock hanging from the bottom of the dress. I turned the movie over and the back cover was a picture of her naked on all fours with muscle-bound man standing behind her and penetrating her with his thick cock.
Her face in that picture is what sold me. She looked so euphoric. I knew that this girl must have, at one point, felt the exact same way as me: just starting to explore her feminine side and knowing that she needed a man to make her truly feel as girly as she could be. If I was ever to experience the pure feminine pleasure she was, I needed to go and pick out my dildo and begin my journey.
I put the movie back and walked to the aisle. I started giggling on the inside, feeling like a little slut in a candy store. Which one of these silicone penises would take my virginity? This must be what girls felt like all the time. As a man, all of the hard work that goes into trying to get a girl to sleep with you can be exhausting. I kept thinking how nice it must be to be a pretty girl and have all the men hit on you, and you being able decide whom you will let inside.
After some serious thought, I picked out the most lifelike one I could find. I figured that if I was truly training myself to one day take a real man, I might as well work with the most real trainer. I made sure that it had a suction cup on it so that I could affix it to my wall and fuck myself doggy style like I always am being fucked in my fantasies.
Even though my outside was still dressed as a man, at this point my inner self was completely girl. Sarah is what I called her. I was all Sarah now.
I tried to make my hips swivel as I walked to the counter, getting in a little wiggle practice. Although, no matter how hard I tried, I could never get quite the same sway as a real girl.
I put my new toy on the counter and began to reach for my wallet.
"34 dollars," said the clerk.
Without a word, I pulled the cash out of my wallet and handed it to the man. He took my money, made the change, and put his hand out. I put my hand under his waiting for him to drop the coins in my palm, but he hesitated. A sort of awkward moment ensued, and then he spoke.
"What are you into?" he said.
My face flushed red and my heart started pounding. I didn't know what to say. I obviously was a guy buying a dildo, what more did he want? I’m sure he saw my cheeks flush.
"You don't have to tell me if you don't want to. I was just curious," he said in a very calming way.
His eyes locked onto mine and, oddly enough, I began to feel a calming wave wash over me. I could sense that this guy wasn't looking to harm me in any way. He was here to protect me. Feeling safe, Sarah came rushing back to the surface. I tilted my head down just a bit so that I could look at him with a little puppy-dog pout.
"Actually, I'm a sissy," I said.
And immediately after saying it, I felt a thousand pound weight lifted off my shoulders. This was the first time I had ever confided this to another human being. But, the way his eyes were still locked onto mine, I couldn't lie to him.
"You don't look like one," he said.
This immediately crushed me and he could tell.
"No, no, no. Don't feel bad. I just mean, you’re wearing boys clothes. Do you have anything in your car you could wear?" he asked.
I didn't. But now my mind was racing in a hundred different directions. Why did he ask me that? Does he want to see me dress up? Is he hitting on me? My heart began racing again, but in a good way this time. What was this new feeling? A new tingling sensation I had never felt before began working its way through my veins.
"I don't, unfortunately," I said in my cutest little whimper voice.
He dropped the change in my hand and immediately cupped it in a warm, gentle embrace.
"What is your name?" he asked.
I let a little coy smile out and replied, "I'm Sarah. What's your name?"
"I'm Matt," he answered.
Another little pause occurred, and then he stroked the outside of my wrist with his finger.
"Sarah, I want you to go walk down that hallway and go into the second room on the left. Would you do that for me?" he asked.
At this point, on any other day, with any other man, I would have taken off running. But, for some reason, maybe it was this new tingling in my veins, maybe it was the fact that my head began to swim and swoon, I just nodded and began to walk toward the hallway.
I had a feeling that Matt would be watching, so I tried to put on my best wiggle-strut for him. The whole time I wished I get it down pat. I couldn't quite figure out exactly how to get my hips to sway the right way yet.
I opened the door and, before I walked in, I looked back at Matt. He had the most handsome grin on and gave me a little wink. I walked in and shut the door behind me.
The room was dimly lit. There was a little bench and some hooks on the wall. This was a dressing room, but larger in size than the ones typically found in a department store. I sat in the room for what seemed like an age. I had no idea what I was doing and what I was in for. All I knew is that I wanted to make Matt happy, whatever that meant. After a few minutes there was a knock at the door.
"Sarah?" said Matt.
"Yes, Matt," I sort of nervously giggled.
"Take your clothes off," he said firmly.
My knees immediately began to shake. My palms got sweaty. I felt like I could faint any second, but Matt's voice telling me what to do made it seem okay.
"Tell me when you’re done," he said.
I took my shirt, pants, and underwear off. I was now standing in this dressing room completely naked and unsure about exactly what was happening.
"I'm done," I replied.
"Good," he said.
The door creaked open just a slit, but Matt did not come in, nor did he peek inside. He tossed in a few articles of clothing that I couldn't quite make out in the dim light and shut the door again.
"Put these on and hang tight, Sarah. A customer just came in. I'll be back in a second," he reassured me.
I walked over and discovered he had tossed in the cutest little pair of black lace bikini cut panties with matching garter belt; sheer, knee-high black stockings; and padded, black push-up bra. With my shaking hands, I picked up the panties and put my legs through one-by-one. When I pulled them up to my thighs, I stopped and took a second to push my testicles up and tuck my cock back, then pulled the panties all the way up so that I had the flat front of a real girl.
I then sat down on the bench and put on the stockings, slowly pulling them up over my knees until they rested on my thighs. Next, the garter belt came up; I pulled the straps down and clipped them to my stockings. Finally, I snapped the bra on. Matt guessed exactly right on my cup size. Being ever so slightly chubby, what little natural breasts I had were pushed up and gave the appearance of perky B cup breasts spilling ever-so-intoxicatingly over the bra line.
I looked in the mirror on the wall and was unbelievably happy. That ‘feeling-so-right’ I got when I dressed at home returned. I was admiring my body in the mirror and how feminine it looked when there was a gentle knock at the door.
"Almost forgot something," Matt said.
The door opened just a slit again and a wig and some basic make-up came in. I wasn't the best with my make-up yet, but I did the best I could. Foundation, blush, eye-shadow, lid-liner, lipstick. When I was finished applying them to the best of my ability, I put on the wig. Matt had given me a dark auburn, long wavy-haired wig.
I put it on my head and swung it back to give it a natural look. When I met my own reflection in the mirror, I was floored. I looked hot. Matt had picked out all of the right sizes for my body and all the right colors for my complexion. This was by far the most beautiful I had ever looked. I was ecstatic.
Then, suddenly, the doorknob to the dressing room started turning. My heart began fluttering uncontrollably, but then Matt's voice came through and soothed my nerves.
"Sarah, baby. Are you all dressed? Can I come in?" he asked.
I took just a second to let my brain register what had happened in the last half hour. Just 30 minutes ago, I was a man driving home from a business trip, and now I had become Sarah, standing vulnerable in erotic lingerie in a dressing room in some hole-in-the-wall sex shop in God-Knows-Where. But, by this point, I was transfixed by Matt.
I looked at myself in the mirror once more, at all of the exquisitely selected items he had chosen for me. He seemed to know me better than I knew myself. After the roller-coaster of emotions of the past half-hour, the only one that was left was a desire to please this man who had been so kind to me.
"I'm ready," I said, "you can come in."
I was nervous again, not for any reason of my own, but because I wanted Matt to approve of me. I wanted him to like me in these clothes he had picked out just especially for me.
He came in, and for the very first time, I saw the look of lust in a man's eye while he stared at me. He clearly liked what he saw. I could see his pupils dilate and watched the throbbing pulse of the artery in his neck quicken.
"You look incredible, Sarah," he said as he walked closer to me.
He stopped just in front of me. We were separated by no more than an inch when he put his hands on my hips and leaned in to kiss me. I titled my head back and accepted his embrace. His lips were on mine and I opened my mouth a little wider. I wanted his tongue to wrap around mine. He obliged and our tongues began dancing around each other.
I felt like I was floating. His hands were on my hips but they were now wrapping around the back of me and he began to squeeze my ass. I could feel every ounce of myself being given over to him. My body was now his for the taking. He could use me in whatever way he wanted. All he had to do was direct me to his every whim.
He pulled me closer and his mouth began wandering to the side of my head. I could feel his hot breath in my ear.
"Sarah, be honest with me. Have you done this before?" he whispered.
Although I wanted to tell him no, that I had no worries, I couldn't lie to him.
"I've never been with a man before," I answered.
I could feel his grip on my ass become a little gentler. I knew I was in good hands.
"Then I'll take it slow for you, baby," he said.
I melted in his arms. We stood there kissing for a few minutes, his hands slowly moving from my ass to hips, down to my thighs, back up to the back of my head, pushing my mouth into his. Then, I could feel his palm on my shoulder and a gentle push down.
This was it. No going back now. I knew what this gesture meant; I had used it many times before on the various women I was with. But, this time, being on the opposite end, it felt better than it ever had before. I knew what he wanted, and I wanted to please him.
I got down on my knees and, for the first time, began rubbing a man's cock through his jeans. It was already semi-hard from our making out, but as I caressed it I could feel it growing even more. I undid his belt, unbuttoned his jeans, and slid them down.
Now the only thing left between my face and his hard cock was a thin layer of underwear. I pulled those down and saw the thing that I had been dreaming about for months. Matt's hard cock was staring me right in the face. I put my hands on it and was surprised by the texture. I had felt my own cock countless times, but it felt so much different to be holding this one. I could feel it pulsing.
As I paused for one last second, a shadow of a doubt crept in. I somehow knew that once I put this cock in my mouth there would be no letting go of Sarah. But, when I looked up at Matt's face and saw the expression of pleasure I had sought to bring out, I wrapped my lips around the end of his hard cock.
I worked my tongue around the head as I slipped my lips up and down the shaft. I couldn't believe how good it felt! I could feel every ounce of masculinity slide off and was overcome with feminine joy. I was working this cock and it felt incredible. Matt was moaning and I knew that my mouth was bringing him so much pleasure. It was euphoric.
I sucked Matt's cock for about ten minutes before I tasted my first bit of salty pre-cum. He put his right hand under my chin and gently pulled me back up. He put his tongue deep inside my mouth, where his cock had just been, and he pushed me against the wall. I had clearly awoken something with him. He was consumed with desire, a desire for me. His hands moved all over my body and I knew that he wanted to fuck me.
He spun me around. I put my hands up against the wall. He began kissing his way down my back and his hands were stroking my inner thighs. I could feel wave after wave of ecstasy over come me. I could tell my body was getting ready. I could actually feel myself giving way in anticipation.
His hands pulled away for a second and I could here a bottle click open and something squirt out. Matt put his mouth on my ear and began whispering just as finger found its way past the side of panties and began gently rubbing a warming gel on my asshole.
"Baby, I know this is your first time, so I'm going to go slow. I need you to relax. Can you do that for me?" he asked.
"Yes, I can. I want you, Matt. I want you to fuck me," I moaned.
The tip of his finger was slowly pushing into me and it felt a thousand times better then when I had done this to myself back at home. Another finger found its way to mouth and I began to suck on it as if it was his cock.
He spun me back around and we kissed for several more minutes. He knew I needed to fully relax. The warming gel was working wonders and I could feel a heat begin to radiate inside me.
"It's time," he said.
He gently turned me around and put his hands on my hips pulling me down to my knees. His chest pressed against my back and his weight guided me down to my hands. I looked in the mirror to my right and saw myself on all fours in front of this man. My legs were spread apart and he was on his knees between them.
I recognized the look on my face. It was the same look that the girl on the movie cover had. I was about to experience the true feminine ecstasy that can only happen when being taken by a man.
Matt pulled the back of my panties down. His hands rested firmly on my hips as his cock eased its way between by butt-cheeks. He stopped when his head touched my whole. He slowly started pushing.
"Just relax, Sarah. You look so fucking hot right now. I'm not sure how long I'll last fucking a girl as beautiful as you," he assured me.
Again, the exact right words I needed to hear. My ass opened up, as if by command on those words, and I could feel all of his seven inches rush inside me. There was a sharp pain. I had never had more than a finger inside me and now I had a fully erect cock! I never even got to try the dildo I came here to buy!
Our bodies rocked back in forth in synced rhythm. The pain I felt slowly gave way to ecstasy. This man was using me for his pleasure and I couldn't be happier about it. He pumped in and out of my ass, over and over and over again. His hands firmly grasped my hips and he used his muscles to pull back my gaping asshole on top of him. I let out moans of pleasure as his cock rammed in and out of my ass.
I glanced back to the mirror and watched my man fuck me. There was no man staring back, however. I saw Sarah, fully and truly. Matt had taken every last drop of masculinity and fucked it right out of me.
Suddenly his pace quickened. His hands squeezed my ass cheeks unbearably tight and he gave one last, deep thrust. I felt his hot cum shoot deep inside me. I was overcome with emotion. I now had the essence of this man inside me, and I couldn't be happier about it.
He held is cock inside me for a few moments as he leaned over top of me and pulled my head sideways and back. He kissed me again as I felt is cock go limp. He pulled up the back of my panties and returned me to a standing position. I could barely keep any balance. My freshly fucked body was still wobbly and weak. Matt leaned into me for one long last kiss.
"My God, Sarah. You were absolutely amazing," he gasped.
Every ounce of my being was satisfied knowing I had let Matt use me for his pleasure.
"You have to get going now before my replacement comes. But, please keep these things on," he motioned to my lingerie, "I want to know that you'll be wearing these as you drive away."
Matt pulled up his pants and walked out of the room. I put my boy clothes on overtop of my lacy undergarments as he instructed. I took a moment to reflect on everything that had just happened and a beaming smile came upon my face. I walked out of the dressing room and Matt was behind the counter again.
"Bye, for now, Sarah. I really hope you find your way back here again," Matt said with a grin.
"I'm sure I will," I said through my gaping smile.
As I walked out of the shop I noticed something amazing. My hips were swaying with every step effortlessly. My ass was wiggling and bouncing with every step like so many girls I had seen before. I knew that I had just been forever changed!
I got in my car and turned on the ignition. As I began driving back down the highway, I could still feel Matt inside me. His cum was slowly working its way out of my ass and pooling in my panties. Sarah had been freed. I was already counting the minutes until I could return back into Matt's arms.
Geraldine
- 09.12.2022
- 33
- 0
- Category:
- Crossdressing
