Man to Woman

by Jane Futa

  “I know! It’s so lame. Maybe if girls didn’t hate me so much it wouldn’t be so difficult to find a model.”

  “You could always ask a guy,” I suggested.

  “It’s hard to find guys too. I would have to pay each of my models and that would add up. Guys don’t usually want to model for free…”

  “I could do it,” I said, unsure of what exactly I’d be agreeing to. It didn’t really matter what it was, though. I’d do anything for Sasha.

  She looked at me curiously and I could see the wheels in her head spinning. “All the ideas I had suited women more than men, though. I also have to use up to 5 different models.”

  “So make me look like different people,” I suggested.

  “You’d have to dress like a woman occasionally…” There it was: that familiar, lustful look in her eyes. Does she have a secret fetish for crossdressing men, or something? I shrugged it off as nothing, but I wanted more than anything for her to look at me that way all night.

  “That’s fine,” I said, feeling my body tense up as I agreed. I wanted to give Sasha what she needed, but I didn’t know if I could actually wear women’s clothes. I tried to remind myself it was no big deal. Guys cross dress all the time to be funny. At least the ones secure in their masculinity did. But what masculinity did I have to be secure in? I was a thin, feminine sort of boy. Adding a dress or a skirt on top of it was only going to make me feel less secure.

  Then I thought of the red panties. What if I like it? Part of me was afraid now that I’d find something out about myself that I didn’t want to know. I’ll just have to not like it. I vowed to myself to shove down any pleasurable feelings that might arise. This was just a project for my best friend. This was a favor to the love of my life.

  What if she loses respect for me? That made me more afraid than anything. What if she always sees me as some girl after?

  “So you’ll do it?” she asked, breaking my restrictive chain of thought. My heart raced and I could hear my blood pumping through my veins.

  “Mmhmm,” I said with a throat that had tightened around my vocal chords. A mumble was the only thing I could get out at a moment, and even then it was barely audible.

  “That makes me so happy!” she cried. She leaned into me and wrapped her arms around me. In that moment, I forgot all of my concerns and got lost in the smell of her hair and the feeling of her body pressed against mine.

  “No problem,” I said in an exhale. My eyelids fell and I leaned my head against hers. She quickly pulled up and looked at me differently. It almost looked like she was considering kissing me.

  I wanted nothing more than to lean down and push my lips into hers right then. Nothing would’ve made me happier. But I was terrified. I was terrified of rejection. I was terrified of losing her as my best friend. As much as I wanted to kiss her, I couldn’t. I stared at her but remained frozen.

  The moment had passed and she pulled herself away. “Let’s watch a movie,” she said. “Tomorrow I’ll go shopping for a few outfits.”

  I nodded and watched as she leaned over for the TV remote. Her shirt lifted up to the middle of her back, exposing her soft skin. I daydreamed about reaching out and touching it. I imagined pulling her close to me and running my hand up to the clasp of her bra.

  Then I had to stop myself to keep my dick from getting too hard. She turned me on more than anyone had, and I couldn’t have her. I exhaled and excused myself to the bathroom.

  I went inside and locked the door. Then I closed my eyes and resumed my image. I reached my hands around to the front of her body and cupped her perfect breasts. I pulled my cock out of my pants and started to stroke it.

  She pressed her lips into mine and slid her tongue inside my mouth. I imagined her stroking my cock as I stroked it, while I caressed her breasts. She moaned and begged for me to fuck her and cum inside of her. I unfastened her jeans and pulled them to her ankles. Then my mind flashed an unwelcome image…she was wearing the red panties.

  The second I saw them in my head, I tried to picture a different pair on her which only made things worse. Now I was in the red panties and she was stroking my cock inside of them.

  I felt my cock swell in my hand and my legs started to quiver. I couldn’t shake the image of the panties wrapped around my cock and balls. I came so fast I had no control over it. My come spilled all over her bathroom floor.

  “Fuck,” I whispered to myself.

  “Is everything alright?” I heard Sasha call from the living room.

  “Yes!” I called back, biting my lower lip as I tried to wipe up my semen. It took a few minutes, but I was pretty sure I’d found every last drop.

  As I walked back to the living room, I felt my cheeks heat up. I just came to the thought of me in red panties. I was about to crossdress for Sasha’s photo project. I was starting to worry about my relationship to women’s clothes.

  Sasha’s smile was so bright and welcoming, though, that I quickly forgot my fears. I joined her on the couch and watched one of her favorite movies.

  Chapter 2

  The next day she invited me to go shopping with her, but I had work. I was a cashier at our local grocery store, but I was desperately trying to look for something else that was more prestigious and made more money. I was in school part time taking business classes. I wanted the kind of job that would impress Sasha one day.

  I knew it was a foolish idea. Sasha didn’t care about how rich her boyfriends were. They mostly just needed to be muscular and total jerks. I still couldn’t figure out why she went after those types. Some of them weren’t even very attractive other than having large arms and chests. They were almost always rude and selfish to her.

  On the other hand, I sat there day in and day out. I was there for her whenever she needed anything. I was someone she could depend on. I was someone who respected her. Yet outside of the few odd moments, she seemed completely disinterested in me romantically or sexually. I thought maybe, just maybe, if I had more money it would outweigh my lack of muscle.

  Minutes before it was time for me to clock out, my boss asked to speak with me. I knew that was never a good sign, but I couldn’t think of anything I’d done that would warrant getting in trouble. I followed him to his office and waited to hear what the issue was. Maybe I was being promoted!

  “Cory,” he said, folding his hands on his desk. His dark eyes peered into me underneath the weak fluorescent lighting. “You know we think you’re great.”

  “Uh huh…”

  “But we’re having to cut back on employees. Our store hours are being cut. You’re just a little too slow at scanning things.”

  “So?”

  “So we’re letting you go. I’m sorry.”

  “What?” I was convinced my ears had deceived me. “You can’t be serious! I’ve been here for years.”

  “I know, I know. But we’re cutting back. You’re a good, loyal worker but you’re just not up to speed on everything. I’d keep you if I could.”

  I stood up, my fists shaking by my sides. But I was a wimp. I knew I wouldn’t do anything. My rage turned back into my usual insecurity. “Thanks for everything,” I said as genuinely as I could. I walked out of his office and to my car. Then I drove off to meet Sasha at her apartment for the photo shoot.

  She pulled the door open and her eyes widened with concern. “What’s wrong?” she asked. I wrapped her in my arms and let a tear fall down my cheek.

  “I just got fired.”

  Chapter 3

  “That’s horrible!” she said, pulling back from me enough to watch my expression for clues. “Do you want to postpone the shoot?”

  I shook my head. “No. Maybe it’ll help get my mind off of everything.”

  “Damn, Cory. I’m so sorry. That’s so shitty.”

  “It’s ok. I wanted to find a better job sometime anyway. I just wanted to be able to do it while still keeping my old one.”

  “Well let’s go to the living room and dig through my shopping bags.
” I followed her to the sofa and watched her shuffle through some clothes. I caught a glimpse of something that sparkled and something with lace, but she pulled out the boy clothes first.

  “Figured I’d start you with something easy,” she said, handing me a suit. I’d never worn a suit before and was almost as freaked out by it as much the women’s clothes. I changed into it quickly and walked back into the living room.

  “Oh. Wow,” said Sasha.

  “Good wow, or bad wow?”

  “Good. Very good. You clean up well,” she said with a smile. She posed me in front of her camera and lights. She took a few shots and directed me on my expressions and posture. It involved a lot of touching, which was my favorite part.

  She had me change out of the suit once she was convinced she got a few good shots. The next outfit was a nice button up and a faded pair of jeans. She seemed to like that outfit too, though not as much as the suit. We ran through the same steps and then she hesitated.

  “That’s it for the men’s clothes,” she said. “Are you sure you don’t mind dressing as a woman?”

  I swallowed and felt my throat tighten again. “Nope,” I managed to mutter even though my head started to feel dizzy. She reached back into her shopping bags and pulled out a sparkling pink cocktail dress. She handed it over to me and I took it reluctantly.

  “Let me know if you need help with the zipper on that,” she said. I took it back to the bedroom to change, but I just stared at it for a moment.

  I took off my guy clothes until I was completely naked. Then I unzipped the dress and stepped inside of it. It was cool and smooth. It fit snugly around my hips and chest. It was unlike anything I’d ever worn before. My cock hardened as it brushed past the silk lining. I slid the straps up to my shoulders and reached behind me to zip it up. I could only get it halfway before I needed some help.

  But my cock was too hard to ask for help. What the hell am I going to do? I tried to think of gross things to get my erection to go down. It eventually worked enough that I was sure my hard on was no longer visible.

  I opened the door and stepped out slowly. Sasha’s eyes widened and her jaw fell open. Something shifted in her posture, as if her knees were suddenly weak. She blinked a few times to snap back from her daze and I saw that lustful look for the third time.

  “I guess I do need help with the zipper,” I said. I walked toward her, careful to keep my hard dick semi-soft. As I walked, I felt the silk lining shift up and down along my hips. I felt elegant and sexy. My second worst fear had been confirmed: I liked wearing women’s clothing.

  Chapter 4

  Sasha zipped me up and then spun me around. She seemed speechless. Her eyes roamed over my face and body and I even caught her biting her lower lip. I wondered if she knew that she had done it or if it was subconscious.

  “You know, that dress looks pretty good on you,” she said, trying desperately to hide her admiration. I blushed. “Of course we’ll need a few more things if you’re going to convince my photography class that you’re an actual woman.”

  I wondered what she meant, but I was soon going to find out. She walked back toward the bags and shifted things around. I heard the bag rustle as she searched for the next item. She slowly pulled out a pair of strappy black heels and showed them to me.

  “Will they even see my feet?” I asked.

  “Even if they don’t end up in the photo, they’ll completely change how your legs look. They’ll instantly look feminine while you’re wearing these.” I cocked my brow at her. I wouldn’t believe it until I saw it.

  I took the heels from her and slid them on one at a time. It felt strange to wear heels on my feet but they added to the sexy feeling. When I stood back up, nearly falling over, Sasha was giggling.

  “What? What’s so funny?”

  “I don’t mean to alarm you,” she said. “But I can see your dick.”

  I looked down quickly and saw a fully erect cock poking out through the dress fabric. It looked like it was trying to escape its new confinement. I was horrified and blushing. “Oh. Sorry,” I said.

  “It’s okay,” she laughed. “I have an idea that could help you.”

  What the hell does that mean? I wondered. She stretched out her hand until I placed mine in hers. I loved feeling her soft skin slide against my palm. She pulled me back into the bedroom and started to dig through her drawers. Finally, she pulled out a pair of silky black panties and handed them to me.

  “These should help tuck it away.” They were ordinary panties, but as I slid them on up over my hips, I realized just how snug they were. She was right. My hard cock was now tucked away neatly and I felt more womanly than ever. I looked down at my legs and saw definition in them that I didn’t think had ever been there.

  “You’re right,” I said. “My legs do look more feminine.” When I looked back up I caught Sasha’s eyes gliding over me, hungrily. I caught her licking her lips. I couldn’t believe this was actually turning her on. Maybe we are meant for each other, I thought. After all, I had fantasies of wearing panties. I even jerked off to the idea. Sasha looked like she wanted to fuck me while I wore women’s clothes. It was a weird situation but I didn’t want to question it. The thought of us being meant for one another made me smile.

  “Okay,” she said. “Now we need a wig and some makeup.” Sasha grabbed a short, blond wig and placed it on my head. She sat me down on her bed while she put on blush, mascara, and lipstick. She stepped back and surveyed my face. “Perfect. There’s no hint of man left in you.”

  I wasn’t sure how I’d felt about that comment but I felt sexy and Sasha still looked horny as hell. I didn’t care how little man I was, I felt like the luckiest person alive. Sasha led me back toward the camera and directed a few more poses.

  “These are fucking amazing,” she said as she looked through the images on her camera.

  “Thanks,” I said with a shrug. I didn’t really have any idea what I was doing. I’d never been a model and I certainly never wanted to be. “I guess we just work well together.”

  She smiled and brushed a hand through her hair. “Yeah, I guess we do.”

  “Okay! Next outfit,” she said, quickly changing the subject. She pulled out a pink skirt that flared out from the hips and a floral tank top. I grabbed the items from her hand and went to the bedroom to change.

  “You don’t have to change in there…if you don’t want to,” said Sasha before I had stepped through the doorway. I stopped in my tracks.

  “You mean…change out here?”

  She nodded. “Only if you want. To make things easier. It’s not like I didn’t just see your cock a few minutes ago.”

  Hearing her say the word cock made me stiff again. I didn’t know if I could handle undressing in front of her, but I wanted to take the opportunity. I turned around and walked back into the living room.

  “Here, let me help you,” she said, walking toward the back of me. I felt her hands on my zipper as she pulled it down slowly, revealing my skin again inch by inch. I could feel her warm breath roll against my skin. For a second, the tips of her fingers grazed it and chills crawled down my spine. I couldn’t believe I was about to get naked in front of her. I couldn’t believe she wanted me to.

  I slid the dress all the way down until I was only in the panties and heels. “You can take those heels off now,” she said. I slid my feet out of them and kicked them to the side. I turned around to face Sasha. I reached up for my wig, preparing to take it off when she grabbed my wrists. “Leave that one on, for now. I have a different one for the next outfit, but this is okay for the second one.”

  I nodded and dropped my hands. She was reluctant to remove hers from my wrists but she forced herself to. I felt a smile forming on my face but I tried my best to hide it. Sasha diverted her gaze and handed me the tank top. She stretched it over my head to help keep the wig from sliding off. I leaned forward and let her slide it over me.

  “Why are girl clothes so soft and delicate?” I a
sked her.

  “Why? Do you not like it?”

  My throat tightened and my body tensed. “No. I do like it. I just kind of wish that boy clothes felt this nice.” She smiled but tried to hide it. I was feeling more and more like there was something growing between us that neither of us was brave enough to admit to. Just when I had planned to lean down and finally kiss her, she handed me the skirt.

  I sighed and stepped inside of it, pulling it up to my hips. Everything felt so good. It was like I was wearing what I was meant to wear all along. What does this mean? I wondered. I couldn’t wrap my head around it. I didn’t feel like a girl necessarily, but I didn’t really feel like a guy either. All I knew was that I loved wearing delicate, soft fabrics more than I liked rough cotton and baggy jeans.

  Sasha stepped back and stared. “You look really hot,” she said. “You might even turn me into a lesbian.” She threw her head back and laughed, but I wasn’t opposed to the idea. Especially if it meant she’d stop dating jerks.

  “Thanks,” I said, half joking and half serious. “What shoes should I wear?”

  “Spoken like a true woman!” she cried with another laugh. I was glad to see her having so much fun. I hadn’t seen her smile this much in weeks. “I have some ballet flats that would look cute with that outfit.”

  She handed me a pair of white flats and I frowned slightly, but tried to hide it. I wondered if I’d still like girly without the heels. I worried my legs wouldn’t look feminine enough. I slid the shoes on reluctantly and Sasha took notice.

  “Do you hate them?” she asked.

  “No, no. I just didn’t know if they’d be convincing enough,” I told her.

  “Cory, you surprisingly still look like a really hot woman,” she replied. I smiled.