Man to Woman

by Jane Futa

  Shit. Now I know why girls do that sort of thing. Once I had a few shots that I liked, I sent them to my email and rushed to my computer, still wearing the stolen lingerie. I emailed Nathan the photos with a message:

  I’d love to have a good time with you at Neon Poppy Festival… ;)

  Then I hit the send button.

  Chapter 3

  The response time from Nathan was lightning fast. You would’ve thought I was his only reply which made me second-guess myself. The good news was that I seemed to fool him easily enough. I could almost see him salivating through his email.

  Looking good, baby. You’re in luck because the offer is still available. What do you say we meet up a couple of hours before the show?

  I raised an eyebrow at this. What does he need a couple of hours for? Shit. He’s hoping for something sexual. I paced my bedroom floor again. I just had to make sure the ticket was in my hand before he found out that I didn’t have a pussy. Then I would need to run like hell in case he was the violent type. People aren’t friendly to transgender folks, and people certainly aren’t friendly about being fooled.

  I had to play my cards just right. I couldn’t let him find out too soon or I might risk my life and miss the concert. Of course…if I gave him a little something to tide him over until the end of the concert…then I could get lost in the crowd somewhere. I tried to think of someway to convince him we’d have sex after. A kiss? A handjob? A blowjob? I stuck out my tongue in disgust. No. Definitely not that. That would make me…gay.

  Or would it make me smart? I rubbed the back of my neck nervously and then looked down at my body. Wearing Jessica’s lingerie almost made me feel like I could go through with it. Almost. I brushed the thoughts away. I knew that I didn’t have to make up my mind just yet. I decided to browse the internet for cheap jewelry making pieces to glue to Jessica’s lingerie. I guess I won’t be giving it back after all…

  While online shopping, I came across a few brightly colored wigs. Yes. Then if it looks fake it’ll make sense. I picked a bright blue, short bob style and added it to my cart. Then I remembered why I got into this whole mess. I was fucking broke.

  It seemed like the more I teased the idea of crossdressing, the bigger of a hole I dug for myself. Where was I going to get a wig for free? How could I return Jessica’s lingerie if I decorated it for Neon Poppy? I paced the floor again. My eyes landed on my textbooks and I remembered the homework I was failing to finish due to my little hair-brained scheme.

  Then I had an idea. Our school had a drama department. I had nothing to do with drama and had no idea how difficult it might be to access the costumes, but I knew there had to be something. I stripped Jessica’s lingerie off and headed back to campus.

  It was late afternoon so the crowds had died down. When I reached the drama building there wasn’t a soul in sight. I swung open the doors and looked around the dark building. I heard the sound of someone performing a monologue from a far off room. I followed the sound, figuring that costumes would be nearby. I breathed a sigh of relief when I realized that I was right.

  I walked down along hallway that ran parallel to the theater. It ended at a T intersection against another long hallway. I turned right and saw it lined with dressing room doors. Certainly they wouldn’t keep their costumes in there all the time. But when I pushed open the first door, I saw 5 glorious rolling racks lined with clothes. Each rack had a basket underneath that was spilling over with accessories.

  “Jackpot,” I whispered to myself. Then I closed the door behind me and turned the lock. The dressing rooms looked mostly like an oversized bathroom. Each wall was lined with counters and mirrors with vanity lighting across the top. I rushed toward the racks and started quickly digging through them.

  I found a hot pink skirt with blue and green sequins covering it, and coins dangling from the edges. It seemed like it was meant for some kind of modern belly dancing performance. I slid my backpack to the floor and stuffed it in. When I came across the matching top, my belly dancing guess was confirmed. It was a fully padded bra covered in coins and sequins. I shoved it into my bag and continued looking.

  I found a few pieces of costume jewelry, but no wigs. I moved some of the racks out of the way to find an entire bookshelf lined with mannequin heads. On each soft, white head rested a colorful wig. My heart started to race. I could look like anything I wanted. As much as I wanted something with bright colors, part of me wanted to see what I’d look like with a natural hairstyle. I gravitated toward a brown wig pulled back into a high ponytail.

  I placed the wig on my head and walked to the mirror. I almost didn’t recognize myself. I didn’t just look like a woman, and I didn’t just look hot. I looked like the hottest thing I’d ever seen. I couldn’t believe the transformation.

  I placed the wig carefully on top of the stolen costume pieces. Then I saw the makeup that lined the counters. I wrapped my arm around a pile of things I didn’t fully understand and slid them into my bag. I only needed one last thing…shoes.

  Next to the shelf of wigs was a shelf of shoes, and I found a pair of sparkling platform sneakers that would be perfect. I scratched my head wondering what kind of performance would require these, but it didn’t matter. They were perfect. I slid them into my bag and then headed toward the door. I carefully unlocked it and slipped out and down the hall.

  As I turned down the other hall, I ran into a guy dressed in all black. “Hey! You can’t be in here!”

  “Sorry,” I said. “I just got lost.”

  And then I bolted out of there.

  Chapter 4

  When the time finally came to meet Nathan, I knew it would be tricky. I had to wait for a moment when most of my roommates were either in their rooms or out of the house. I parked my car down the street so that if I got caught at the end of the driveway, I’d look like any other chick. The last thing I needed was for my roommates to see some festival chick getting into my car with the keys and driving off…

  I kept Jessica’s lingerie for the time being so that I could use her panties. Since the top I found at the drama department was practically its own bra, I knew I wouldn’t need hers. I shaved my legs again, dressed myself, and applied makeup as expertly as I could. It took a good amount of tutorial videos for me to get it right. The only thing that helped me with it was that festival makeup was usually a bit crazy, so I knew it wouldn’t have to be perfect.

  By the time my face was made-up and my wig was on, I was absolutely unrecognizable. At least that’s what I hoped. I still wasn’t sure what I was going to do once I met Nathan, and I definitely wasn’t looking forward to hanging out with him for a few hours. I knew it was too much time for him to try and fuck me or something. I calmed myself down and then listened for any noise coming from outside of my bedroom.

  When I was certain the coast was clear, I quietly snuck out of my room. I bolted down the hallway as quietly as possible. I looked outside to make sure I didn’t see anyone I knew and then I jogged to the street. I knew I was safe once I was on the sidewalk. I exhaled and trekked toward my car. Fortunately, it was only a block away because the platform shoes were a bitch to walk in.

  I got in my car and pulled up Nathan’s address. I couldn’t believe he was crazy enough to trust me with it. What if I sent someone to rob him or something? I shrugged it off and entered it in my GPS. I followed the route for about 30 minutes until I pulled up to a small, white house. All of the windows had curtains drawn even though it was the late morning. I shuddered at the thought of being trapped inside his dark house dressed as a woman.

  What if he finds out that I’m a fraud? I tried to calm myself and then headed to his door. Before I could even knock, he pulled it open.

  “Nathan?” I asked in a high pitch voice. He looked slightly different from his photo. His body was fairly muscular and his face was handsome.

  “Yeah. Are you Crystal?” I nodded. He smiled eagerly and ushered me in. I followed him to the back of the house where, thankfully,
the curtains were drawn open. His house opened up to a gorgeous lake and he had a hot tub on his deck.

  “This is really nice,” I said in an airy tone.

  “Yeah. People don’t expect it to be when they pull up. It’s a small place, but I like them cozy.”

  There was an awkward silence growing between us. I wanted to know he actually had the tickets before I gave him too much more of my time, but I didn’t want to offend him either.

  “Thanks for inviting me to the festival,” I said, batting my eyelashes playfully.

  “Oh, right,” he said. He padded his body down with his hands until he remembered where he’d placed the tickets. He reached into his front pocket and it was then that I noticed his long, hard dick trying to burst through his pants. I expected seeing it to make me want to run, but it didn’t. Instead, I felt strangely flattered and…curious.

  He pulled out the tickets and set them on the counter. “Thanks for being my date,” he said. He seemed nervous. I could tell he wanted to ask me for some kind of payment, but he was afraid. Maybe a hand job would satisfy this guy.

  I walked up to him slowly and his eyes widened. “I don’t know how I can repay you,” I said seductively. I half-hoped he’d push me away and insist we just stay friends, but deep inside part of me wanted him to let me flirt with him as a girl. I walked closer to him, my hands reaching for his. Then he stepped toward me. He placed his hands on my hips and leaned in, pressing his lips to mine.

  I’d never kissed a man before, and I think if I’d been dressed in my normal clothes it would’ve felt wrong. But something about wearing a skimpy skirt and having his rough, muscular grip on me made me want to slide my tongue down his throat. We parted lips and I could feel his hands trembling.

  He was too attractive to have bad luck with women, I thought. Why is he so nervous? I placed my hands on his chest and let them slowly travel down to his belt buckle. His breathing grew heavy and he shook against me. I could feel his passion quaking inside his body, and when my hand ran over his giant bulge, I could tell it was ready to escape.

  Maybe he just likes strange women, I thought. I rubbed my palm gently against his shaft. Suddenly, I wanted him to take me, bend me over, and fuck me right there.

  What the hell is wrong with me? It was like my past identity, all my friends and everything I knew, just slipped away. I was someone new, someone confident and sexy. I was Crystal, and Crystal had sex with strange men in exchange for extravagant gifts.

  I unfastened his belt and pants, his tongue still circling mine. I started to reach my hand into his briefs when he caught me at the wrist. I suddenly realized how dainty I was next to him. He pulled his head back and looked at me with wide, worried eyes.

  “What is it?” I asked, shocked that I wasn’t pleased at him stopping me.

  “I should warn you…”

  Shit. He’s got an STD or something…

  “My cock is…well it isn’t…”

  “You can tell me,” I assured him.

  “It’s not circumcised…”

  Suddenly it made sense. I knew how shallow people could be and I sympathized with him. I was being given a great opportunity to make him feel better about who he was. In exchange, he would help me feel better about dressing as a woman.

  “I don’t mind,” I said. “Certainly you haven’t been rejected that much.”

  “I don’t give people a chance,” he said. “I’m a…”

  “A virgin?”

  He nodded and dropped his head. Suddenly I was salivating. This guy isn’t going to try and fuck me. He’d probably love even just a hand job. But I wanted to give him more. I wanted to show his cock how loved it could be. I dropped slowly to my knees and looked up at him. Nothing made me feel more feminized in that moment than being on my knees with my face to his groin.

  I slid his pants and briefs down to release his hard cock. As stiff as it was, you couldn’t even tell it was any different. I looked at it in awe…my first blow job. I wrapped my fingers around his shaft and watched it pulse in my hand. He wanted me and I wanted to give myself to him.

  I opened my lips and relaxed my jaw. I stuck out my tongue slightly and flicked it along the underside of his head. He moaned immediately and threw his head back. “Fuck,” he sighed.

  I licked it a few more times before wrapping my mouth around his bulbous head. I sucked my cheeks in and lowered down.

  “Fuck,” he sighed again. He cursed with each new inch I took in. I slid my tongue along him while I moved back and forth. Minutes later, he was shooting hot cum down the back of my throat. I’d never tasted cum before, but I liked it. I liked it so much that I thought about doing this again. Maybe not with Nathan, but with someone. Only if I could be dressed as a woman, of course.

  He groaned as he finished and then pulled himself from my mouth. “You didn’t have to do that,” he said.

  “I wanted to,” I replied with a reassuring smile. He zipped himself back up and I picked myself up from the floor.

  “Should we head out to the festival?” I nodded and then we left.

  This is going to be one hell of a trip.

  Chapter 5

  We got to the festival after the first few bands had played. The parking was insane and there was dust flying in the air. You could hear the bass from the back of the parking lot.

  I couldn’t believe I was going for free and that I was going dressed as a chick. I knew this would be unlike any other year’s experience. I wondered if I’d get hit on or get dared to make out with someone. Everything would be different now that I was wearing a skirt.

  The closer we walked toward the fairgrounds, the crazier the scene got. There were sculptures and rides and tents for miles. And everywhere I turned there were hot chicks that were already half-baked or wasted. I shook with excitement as we walked through security.

  Nathan assured me I didn’t have to stay with him the entire time, but I couldn’t think of who else I would hang with. I couldn’t tell my friends that I had shown up as a girl. I figured I’d tell them later on that I snuck in somehow and saw the show, but that I couldn’t get a cell signal or something. I knew I had time to make up a good excuse later.

  We swiftly entered the crowds of costumed people. Everyone was laughing and swaying and it was easy to feel at home and accepted. I couldn’t feel bad about dressing like a chick when everyone was dressed in crazy, wild costumes. It was one giant masquerade festival. The more out of body you acted, the more you were adored.

  I was surprised to see how much a guy like Nathan lost himself in this kind of crowd. I wouldn’t have pegged him for someone that liked electronic concerts but I started to feel like he felt included here as well. He seemed to blend in perfectly with the waving arms and swaying hips around us.

  We didn’t talk much during the festival. We grabbed some beers and had some laughs and we even met quite a few friendly strangers. It was as fantastic of a time as any other year, except this time I had a secret identity. Not one single person seemed to peg me as a dude or, if they did, they didn’t call me out on it.

  The day was nearing its end and I my head was spinning from all the excitement. I told Nathan I was going to wander through the crowd and he waved me off. I wanted to disappear amidst the people and really become a part of everything. I closed my eyes and stretched out my arms, brushing past dancing bodies as I walked through the chaos.

  That’s when I recognized his voice. “Hey there sexy!” called Jason. My eyes shot open wide and I turned toward him. “What’s your name?”

  He didn’t recognize me. I can’t believe he didn’t recognize me. “Crystal,” I replied in a high tone. Jason didn’t look wasted, but he still didn’t seem to know it was me underneath all the makeup.

  “You alone?” he asked in a concerned tone. I never realized how big a sweetheart he could be. He always jokingly insulted his friends, but know that he knew I was chick, he seemed worried about my well-being.

  “No. Just wandering!” I
shouted over the music.

  “Well, be careful. You can hang with us if you want!” He pointed behind him and I saw the rest of our friends dancing. They all looked at me with a lustful stare. None of them fucking recognize me. This is hilarious! It wouldn’t have been funny if they did recognize me, but since they didn’t…I should hang around and mess with them a little.

  “Thanks. I think I will,” I said. I walked up to Jason and started dancing. I shook my hips, knowing full well that the guys behind me were staring at my ass. I chuckled to myself. They have no idea that this chick has a cock between her legs.

  Jason looked at me every few seconds and smiled. My cheeks flushed and my heart beat faster. The way he looked at me made me feel special and desired, and not just in a sexual way. He was sweet and tender and friendly. Not that Nathan hadn’t been, but this was different.

  He looked at me again but longer this time. I suddenly had the urge to kiss him, but I held back. Staring into his gorgeous eyes with the music surrounding us and the lights sending us into another reality made it easy to consider kissing him. But I couldn’t…he’s my best friend.

  When the song ended, he leaned down and put his lips near my ear. He whispered, “Want to go somewhere a little quieter?” I swallowed and nodded. What the hell am I getting myself into?

  I followed him through the crowd as we searched for an open area away from most of the stages. He reached his hand for mine so he wouldn’t lose me. I smiled and blushed, sliding my fingers in against his palm. He felt warm and safe and I never wanted to let his hand go.

  We found a small patch of trees surrounded by tents. There weren’t many trees in this place, so they were hogged by people camping out. He led me into them until we were safely unseen. He turned to me and let his eyes wander over my face.

  I felt his gaze on my eyes and then my lips. I watched them travel slowly down to my breasts and around my hips. My cock stiffened and my body tingled. I didn’t know how I could have him, but I wanted him bad. I couldn’t hold back any longer. I wrapped my arms around his neck and pressed my lips to his. His tongue slid quickly into my mouth and he tasted like maple syrup straight from the trees.