Becoming Sarah

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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, güvenilir bahis 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 güvenilir bahis siteleri 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 iddaa siteleri 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.

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