Man to Woman

by Jane Futa

  This is all so ridiculous, Neal. You can’t consider things like this for real. But I couldn’t help it. I looked back at my reflection and felt love for myself for the first time in a long time. I’d always been so insecure about my masculinity or lack thereof. I’d always been ashamed of my body, but wearing that pink dress and bob wig, I felt like a sex goddess. I felt like I could do anything. I felt beautiful.

  “Go ahead,” she said. “Sit down.” I sat right in front of her vanity mirror so that she could apply makeup. An array of brushes swept across my face. Glosses and sticky colors were applied. Wands danced and dabbed in the right places. By the time she was finished, I looked like a completely different person. I looked hot. I wanted to bang myself.

  I reached up to touch my face, confused by the new contours that extended under my cheekbones. “Careful,” she warned. “You don’t want to smudge it.”

  I nodded and dropped my hands. “Now all you need is some jewelry and a pair of killer shoes.” She returned to her closet to grab a few things and when she came back, she stopped in her tracks. She stared at me for a moment, taking me in. “You know, Neal. You’re a pretty good sport. Thanks for letting me play dress up.”

  “No problem, Mrs.-“ I caught myself, “I mean, Wendy.” She smiled and returned to my side. She fastened a gold necklace around my neck and slid a matching gold bracelet on my wrist. The necklace had a small charm shaped like a feather. It seemed to symbolize an independent spirit, something that Wendy was full of.

  I admired that about her. I wanted to be independent like her. I wanted to brave enough to dress like this whenever the hell I wanted to.

  She slid a pair of heels next to my feet and helped me inside of them. They felt awkward at first, but once I stood in them I fell in love. My calves naturally flexed as I balanced on the stilettos. My thighs looked sexually alluring. I could imagine a big, strong hand glide up them on their way to a pussy paradise.

  “It’s all perfect,” I told her, still in awe with the transformation. I’d never pictured myself as a woman before. I never would’ve thought I could pull it off even if I wanted to. But I didn’t recognize myself, and I liked it.

  “We could…show it all off if you wanted,” she said. “I could take you out to eat or something.”

  My heart raced. The thought of others seeing me dressed like this freaked me out. “I don’t know. What if someone recognizes me?”

  “Do you recognize you?” she asked. I looked back in the mirror and already knew the answer.

  “No. I don’t.”

  Chapter 5

  I couldn’t believe I was letting Wendy take me out into the world dressed as a woman. I rode passenger in her car and ducked down anytime we came to a stoplight or other intersection. If I felt like someone stared at us on the highway, I shied away. She reassured me it was only because there were two gorgeous women in the car that people were staring, but I just couldn’t believe my costume was fooling anyone.

  She guaranteed me that we’d return home promptly if it seemed as if anyone recognized me. We lived in a somewhat small town so I was certain someone would. She also said if I ever felt uncomfortable to let her know.

  “I’m really excited to have a girl to go out with for a change,” she said.

  “What about the girl I saw you with the other night?” I panicked when I realized what I’d just said.

  “So you were watching me! I thought I saw your head peeking through your blinds.”

  “You saw me? Oh god, I’m so sorry.”

  “It’s okay. Did you enjoy the show?” she asked, cocking an eyebrow at me and taking her eyes off the road for a moment to catch my reaction.

  I blushed. My body heat rose higher. I didn’t know if I could admit to liking what I saw. I wasn’t completely sure what I even thought about it yet. “I don’t know,” I said finally. It was the most truthful answer I could think of.

  “Let me rephrase it. Did you jack off to what you saw?”

  She caught me in a bind now. I would either have to lie to her or admit that I enjoyed watching enough that I masturbated to the show. I bowed my head and bit my lower lip. I felt the strands of my wig drape around my face. I liked the way it shielded my unsure expression. I tucked it behind my ear and sat up quickly. With as brave of a stature as I could muster, I nodded.

  She smiled. Then she reached a hand across to my thigh. I noticed her nails were painted hot pink and she dug them in lightly to my skin. “That’s really hot,” she said.

  My lips rose into a smile. I was glad that my spying had turned her on, but I still wasn’t sure how I felt about everything that had happened in the past twenty four hours.

  We finally pulled up to the restaurant and hopped out of the car. Everyone was staring at us. The only thing that relieved me was that they seemed to be staring at Wendy as much as they stared at me. I couldn’t blame them. I wanted to stare at her all day, too.

  We got our table in the busy restaurant. My nerves felt shot. We sat in the middle of the entire place, right where everyone could look at us. I kept shifting my gaze left and right to see if anyone was laughing or pointing me out, but no one was. I started to settle into my seat when the waiter came up to take our orders.

  The waiter didn’t seem to notice anything wrong with either of us. In fact, everything seemed just as normal as if I’d worn my guy clothes to go eat.

  “Will you relax?” asked Wendy. She lifted her leg so that it was hidden by the long tablecloth and traced her heel up my calf. I felt chills form under my skin. My cock stiffened slightly but I tried to keep it under control.

  “What are you doing?” I whispered, leaning over the table.

  “Just having a little fun.”

  “Someone might see…”

  “Oh, hush. Everyone’s eating and sitting with someone else. They won’t have any clue unless you make it obvious.”

  I sat back in my chair. I could tell she wasn’t going to let up. She slid one of her heels off and dragged her barefoot up my calf and thigh. She slid it under my skirt and between my legs.

  I felt her toes run along my lace covered shaft. It was rock hard now and only hidden by the tablecloth. If for some reason I had to stand up in that moment, every single person in that restaurant would see what I was hiding under my dress.

  My heart raced as she let her toes dance along my balls and cock. I exhaled through my nostrils, trying to pretend that everything was normal. My eyes stared directly at her and her eyes stared at me. She was daring me with them. She was daring me to stop her and she was smiling because she knew that I wouldn’t.

  The base of her foot curled so that it rested against my shaft. She slid it up and down until I thought I might come. Suddenly, she dropped her foot and placed her folded hands underneath her chair. She looked up as the waiter approached our table with our drink orders.

  I was exhaling heavily as if I’d just run a marathon. “Are you alright, ma’am?” he asked. I looked up with sheepish doe eyes and nodded.

  “I’m just parched. Thank you for the drinks.”

  “No problem,” he said, winking at me. I looked back at Wendy who was smiling at me.

  “He totally likes you! You should get his number,” she teased.

  “Can we just eat, now?” I asked, hoping she didn’t have any more cruel tricks for me. She nodded.

  “I’m sorry. I was just having a little fun. We’ll keep it simple now,” she said. I was grateful and the rest of the meal was divine. After we paid our check and were about to leave, Wendy turned to me. “Hey, I’m going to run to the bathroom. Care to join me?”

  “In the women’s?”

  “Of course, silly,” she said while looking around to see if anyone had heard. She grabbed my hand and pulled me off into the bathroom which was surprisingly empty. She rushed into the biggest stall, dragging me behind her.

  “What’s going on?” I asked. “What are we-“ I became speechless when I saw her lift up her skirt and slide her red p
anties down.

  “Get on your knees. My pussy is so fucking wet right now from touching you out there. I need you to get me off.”

  “Here?”

  “Yeah,” she said, looking around. “Where else?”

  I dropped to my knees as she’d asked. She walked up to me until her pussy was inches from my face. I’d never eaten a girl out before and I hoped I would do a good job. Mrs. Matthews deserved to be pleased right.

  I stretched out my tongue and let her maneuver her hips over me. Her pussy was wetter than I had expected and my face was soon drenched. I slid my tongue inside her wet hole and swirled it around. She tasted like honey and flowers. I could spend all day between her legs if she’d let me.

  She reached for her breasts and played with her nipples while I licked. She panted over and over, trying to keep quiet. I could tell she wanted to moan. She seemed as if she was used to screaming.

  I flicked my tongue along her slit and circled her clit. I couldn’t believe I was eating out Mrs. Matthews’ pussy. What would Bryce think? What the hell would he think of me dressed as a woman? I felt like a lesbian as I wore that little pink dress while eating pussy.

  It was the greatest feeling of my life. But I was about to realize how many great moments Mrs. Matthews was planning to give me.

  She rocked her hips a few more times before she came. Her pussy clenched around my tongue and pulsed as her orgasm rippled through her body. She panted heavily and braced herself against the stall door.

  Just as we’d finished, someone came into the bathroom. Wendy motioned for me to stand up quickly, and when the new person disappeared into a stall, she snuck out first.

  I left shortly after and we ran to the car giggling like a couple of girls.

  Chapter 6

  “Where to next?” she asked once we were safely in the car.

  “What do you mean, where to next?”

  “You’re not ready to go home already are you? You didn’t get all dressed up just to go out to eat with me, did you?”

  “I didn’t know what I was getting dressed up for,” I admitted.

  She cocked her head to the side as if she didn’t believe me. “How about we go to a movie?” I thought about her suggestion seriously. At least a movie theater would be dark.

  “Okay,” I replied. She quickly started the car and drove us to the movie theater. Once we were there she told me she was going to pick the most boring movie that was playing.

  When I asked her why, she just replied with, “You’ll see.”

  She held my hand, this time locking her fingers inside of mine. I felt instantly cradled. I was protected and warm. We ordered a few snacks and slid into the back row of the theater. I may have never crossdressed before but I knew what the back row of the movie theater was for. You didn’t have to be gay or a sissy to know that.

  Once the lights dimmed and the movie started, so did Wendy. She laid her soft hand on my thigh and inched it upward. Soon it was under my skirt completely, cupping my hard cock. She traced her fingers along my shaft and balls, and I tried as hard as I could to not moan.

  Her fingers slid my panties to the side and wrapped around my hard shaft. I couldn’t believe she was trying to jerk me off in the movie theater. She grabbed my hand and slid it underneath her skirt, pressing it up against her cunt. It was already wet again. I couldn’t believe it. She had the highest sex drive of anyone I knew.

  I slid my finger into her panties and up her slit as she stroked my cock. We both leaned back in our seats, pleasuring each other. When Wendy knew I was about to blow my load, she angled my cock down so that my jizz would fall onto the floor. This girl knew what she was doing more than I had anticipated. It made me wonder how many people she’d done these things with.

  I suddenly realized how badly I wanted to be the only one that pleased her. I wanted to be her only little sissy. I wasn’t sure how I’d ever tell someone like Bryce, but I had to at least try and win Wendy’s heart somehow. It was more than clear to me now that I was absolutely in love with her.

  I fingered her until she seemed to come in the seat next to me. She winked at me to let me know when she had finished. I slid my fingers out from her legs and brought them to my mouth. I licked them clean and she smiled.

  We actually watched the rest of the movie and it didn’t end up being as boring as we thought. Wendy reached over for my hand in the middle of it and just held it. I felt like I was floating. Even if she didn’t want me to be hers by the end of the day, I knew I would always have this moment. I smiled to myself through the rest of the film.

  The lights went up and we started to leave. A pair of guys that had been sitting next to us seemed to be stalking us down the stairs and out of the theater.

  “Do you notice them?” I asked Wendy.

  “They probably just think we’re hot,” she said, shrugging her shoulders.

  “Hey dykes!” cried one of them. I turned around with a scowl on my face and he threw his soda at me.

  “What the hell?” cried Wendy.

  “We saw you two cunts fingering each other in the theater. You guys make me sick,” he said. They marched off toward the exit and Wendy pushed me up against the hallway wall.

  “We should wait here a moment. I want to make sure they leave.” I nodded, still dazed by what had just happened. I’d been bullied before in school, but no one had ever thrown a drink at me. As harmless as it was, it felt just as violent as a weapon.

  My heart pounded and everything swirled into a blur. I fell to the floor and tried to catch my breath. My chest was tight and my head was dizzy. I cradled my legs into my chest and bowed my head. Wendy slumped beside me and wrapped her arm around me.

  “It’s okay. We’re going to be okay. Don’t worry about it. Just breathe.” She rocked me back and forth against her chest. A small crowd formed to make sure we were alright. A few of them had seen the incident and offered to call the police. I waived them away because I was still trying to process everything.

  After a few minutes had passed, Wendy helped me to my feet and we went back to her car. We sat there without moving until I was breathing normally again.

  “Are you sure you don’t want to press charges?”

  “I kind of just want to go home, if that’s ok,” I replied.

  “Of course,” she said. The rest of the car ride was silent.

  Chapter 7

  When we arrived back at her house she held my hand until we were inside. Then I fell against her and cried. She stroked my hair and let me weep on her shoulder.

  “What is it, Neal?” she asked me.

  I pulled away from her and avoided eye contact. “It’s just that…” I swallowed, trying desperately to find the words to express myself. “I felt so good about myself all day. I’ve felt the best that I’ve ever felt. I even started to wonder if I was meant to be a woman, or at least crossdress more often…”

  She widened her eyes to let me know she was listening. “And then when that happened…it was kind of terrifying.”

  “That’s completely understandable. You don’t have to do anything that makes you feel uncomfortable or threatened. But if you enjoy the way you feel as a woman, you can’t let anyone convince you otherwise. I’ll always be here for you.”

  My gaze met hers, but I was suddenly full of distrust. “Am I just some fling for you? Just some toy for you to play with?” I asked finally.

  Her eyes lowered to the floor. I could tell she was giving it serious thought. She folded her arms. “I’m sorry, Neal. I never meant to get you caught up in all of this. I do like you, but I don’t know how I’d explain any of this to Bryce. I kind of just thought today would be a little fun.”

  “But I’m in love with you, Wendy.” My chest seized up as I heard the words escape my mouth.

  She looked at me with wider eyes than before. Her jaw hung open. She walked toward me and cupped my face in her hands. “I know I shouldn’t…” she said, “but I…”

  Before she could get
the words out of her mouth I kissed her. I wrapped an arm around her waist and drew her into me. Her lips pushed against me differently than before. They were tender and soft. The ferocity was gone and I felt them tremble slightly.

  Her tongue slid into my mouth and she hooked her arms around my neck. I ran my hand up her spine and she quivered against me. It was the first time all day that she seemed vulnerable, and it made me believe I had a chance with her.

  I slowly lifted her top and she pulled away from our kiss long enough for me to remove it and toss it to the floor. I gripped her breasts as she started to unzip my dress. She slid the straps from my shoulders and I could feel my entire body shaking with anticipation.

  This wasn’t some slutty experience. We were about to make love. I grabbed her neck and kissed her passionately. She reached behind my back and unhooked my bra. She brought her hands around to my chest and squeezed my pecks as if I had small breasts there instead.

  I smiled and she blushed. I turned her around and kissed her neck from behind while I unclasped her bra. I watched over her shoulder as it fell to the ground. I reached up from behind and cupped her full breasts in my hands. Her nipples hardened against the palms of my hands.

  I lowered them slowly until my thumbs were brushing against her nipples. She gasped at my touch. I slid a hand into her skirt and traced a finger along her panties. My other hand continued to tease her nipples. My mouth kissed her neck. My teeth bit her skin.

  I took her ear lobe into my mouth and nibbled lightly. She rotated her head against me while moaning. She had completely lost herself to me. I wanted to give myself to her.

  I pressed my lips to her ear and whispered something I never thought I’d ever ask for. “Would you fuck me with that cock I saw you with last night?”

  She pulled away from me and turned around to face me. “Are you sure?”