Man to Woman

by Jane Futa

  I lost myself in that kiss. I finally felt fulfilled. I was in love, and the man I loved was kissing me. My head spun. I grabbed his neck and pulled him in close, but he pulled away. I worried that he felt like he made a mistake. I watched him closely as he spoke his next words.

  “What about the other guys?” he asked.

  “What about them?”

  “They’re just going to come find you and drag you back to the church.”

  “What about Rene?” I asked him.

  “She left. She was so pissed that they all wanted you that she fled town.”

  “Really?” I couldn’t believe what I was hearing. So that was the end of it…or at least, it could be. “I’ll break it up. I’ll end the cult.”

  “How? This has brought so much happiness to them…to me.”

  “I’m the leader now, right? I’ll just tell them it’s over.” John shrugged his shoulders as if he didn’t believe it could be done. I wasn’t completely sure about myself, either.

  “So what now?” he asked.

  “You could come inside with me,” I told him.

  Chapter 8

  We barely made it inside before we had our hands roaming each other’s bodies. I pushed him up against my door and cupped his chest as if he had really small breasts. He moaned into my mouth and slid his tongue around my lips. I pushed my body against his and felt his cock growing underneath his skirt. I pushed my hard dick up against his through the fabric and rocked my hips into his.

  He slowly dropped to his knees, kissing me along my dress all the way down. As I looked down, I watched him caress my now feminine, girly body. I could see the strands of my wig draped over my chest. I was about to have a sissy guy go down on my woman’s body.

  John ran his hands along my thighs and I cooed with delight. He slid his fingers underneath the skirt of my dress and lifted it up slowly. I couldn’t believe he was on his knees in front of me. I couldn’t believe everything we had been through. I couldn’t believe how necessary it all was to get to this moment in time.

  He pulled my dress up above my hips and licked his lips. He dragged the palm of his hand over my erection, on top of the silk panties. He leaned in and kissed the fabric that rested against my shaft. I arched my head back and moaned. He was teasing me, but every single touch from him sent a wave of pleasure through my body.

  He pulled my panties down slowly. He dragged them all the way to my ankles. Then he wrapped his hand around the shaft of my cock like he had the day before. Only this time, he was going to take it into his mouth. I was going to fulfill my fantasy of watching a sissy John suck me off. I can’t believe this is happening. I can’t believe we’re really here and he’s really in front of me on his knees.

  He parted his lips and wrapped them around the head of my cock. It was better than everything. It was the single greatest pleasure of my life. I felt his tongue swirl along the underside of my shaft. He traced patterns I couldn’t keep up with. Then he slid it further into his mouth.

  He took it in inch by inch until he’d swallowed it whole. I looked down at him and he looked up at me. I stroked his beautiful, feminine face. He didn’t need makeup. He didn’t need a wig. He looked girly and slutty enough without them. He was my little sissy slut and I was in love with him.

  He pulled his head back slowly and caught his breath. He swallowed it again and pulled back. Then he lifted my shaft up and moved his mouth to my balls. He took them in his mouth and let his tongue dance across them. I rested a hand on the back of his head, urging him to continue. It felt so good to have my best friend licking my balls. I wanted to come all over his beautiful face. I wanted to come all over his sexy, feminine body.

  I shoved my cock back in his mouth and pumped it in and out of him. He looked at me lovingly as he swallowed inch after inch of my cock. I couldn’t hold back any longer. Within seconds I was coming down his perfect, girly throat. He swallowed every drop and then licked my shaft clean. He did it with a smile.

  When he stood back up I kissed him. I wanted to taste my come inside his mouth. It was heavenly. It was perfect. This is what I’ve been missing, I thought.

  Now it was time to repay him. I led him to the bed. He started to lay down, but I held him back. “I want to feel you inside me,” I told him. “I want to be your little slut.”

  He blushed and smiled. He pushed me onto my stomach and lifted my skirt up until he had revealed my ass. He gave it a spank and I moaned. I felt him spit onto my ass and rub it in my crack. Then he probed me with his finger, curling it around as he slid it in. My body tingled with heat. I had just come but I thought I could almost come again from the new sensation.

  He spit again and slid a second finger inside. I moaned again and he moved them in faster. He slid them in and out of me as I writhed on the bed. He spit a third time and worked a third finger in. He was stretching me now. He was preparing me for his hard dick.

  I looked over my shoulder at him. I wanted to see him in his little sissy outfit. He was wearing the skirt and corset from the other day. I stared at the cleavage the corset gave him. I saw his dick hanging out underneath his skirt. I reached back and started to stroke it. He leaned his head back and moaned. He couldn’t take it any longer. He wanted to be inside me.

  He straddled my legs and rested the head of his cock at my asshole. “Tell me if it hurts,” he warned as he slowly pushed in. It hurt a little but I didn’t want him to stop. I felt him stretching me wide open. I couldn’t believe I was having anal with my best friend. I couldn’t believe that this was what I had been missing. I loved him and I wanted to feel him split me open like a little whore.

  He slid his cock further inside of me. With every inch he released another groan. I reached back and grabbed his thighs tightly and passionately. “Does it hurt?” he asked.

  “Not at all. Treat me like your little slut. Fuck me like your little sissy whore,” I commanded. He moaned and slid his cock all the way in. I lied. It did hurt. It hurt like hell, but I loved it. I loved feeling him dominate me. I loved getting my virgin ass stuffed by his cock. I loved that we were each other’s little sissies.

  He pulled out slowly and thrust himself back in. It felt so fucking good. I couldn’t get enough. He leaned his hands down on my back and began to pump in and out of me. His balls swung against mine as he fucked me. He leaned down and whispered, “You’re so fucking hot. You’re the hottest girl I’ve ever seen.”

  “Fuck me like your little slut,” I said. He pounded his hips against mine. “Come for me. Show me how hot you think I am in this tight little dress.”

  “You’re so fucking hot,” he said, thrusting in and out of me. He looked down at my body, my dress pushed halfway up. He spanked my ass and thrust harder. “I’m going to fucking come,” he warned.

  “Yes, come for me,” I begged. The head of his cock swelled until it burst. His come spilled deep inside of me. My ass felt warm and sticky. I bit my lower lip as I felt my dick grow harder. I loved being filled by him. I loved feeling his come flood my tiny asshole.

  He groaned until he was finished. Then he lay on top of me. “I have a confession,” he said, stroking my blond hair from my face.

  “What is it?”

  “I’m curious what it feels like to be filled…”

  “I can show you if you want,” I told him. He smiled and kissed my cheek. He climbed off of me and laid next to me on his stomach. I smiled and stood up, feeling his come drip from my ass and down my thigh. My legs became a sticky mess. I reached down and slid my fingers along the wetness until they were covered in his come. Then I brought my fingers to my mouth and licked them clean.

  He tasted so good. His come was as intoxicating as the day before. I looked down at John in his little skirt and corset and smiled. He was a sexy little sissy and he was all mine.

  I reached for his stocking covered legs and ran my hands up them. He twitched as I caressed them. I loved him in those stockings. I was excited to be able to show him something new. I w
anted to fill him up the way he had filled me. I wanted to become one with him and show him how good it feels to be penetrated.

  I lifted his skirt up. Then I leaned down and kissed his ass to show my love for him. I spread his cheeks wide and stuck out my tongue. I licked his asshole to get it wet. Then I slid my tongue inside of him. He groaned with pleasure. I wiggled my tongue around, exploring the inside of him, as if I were eating his little girly pussy.

  I slid my tongue in and out, simulating what my cock would do. Then I lifted my head and pressed my fingertips against his hole. I slid three fingers in at once. I delighted in the way his ass stretched around me. He moaned like a little girl and I smiled.

  “You like that, you little slut?” I asked him. He nodded. I pumped my fingers in and out of him faster until his ass started to relax around me.

  “Does it hurt?” I wanted to check in with him before I continued. He shook his head. He must’ve known I was lying before about the pain, but he must’ve enjoyed it just the same. He was lying to me, after all. I saw a wince or two as I slid my fingers in and out, but he wanted me to continue.

  I pulled my cock out and stroked it a few times. Then I pushed the head of my cock into his ass. I felt his ass stretch around me and clench my dick hard. I didn’t know how long I’d make it in his tight ass before exploding. I wanted to show him how it felt, so I had to hold on a little longer.

  I bit my lower lip and pushed in slowly. He gripped the bed sheets in his hands as I slid in deeper. Soon, my balls were touching his and I lay flat against him. I picked up my hips and drew myself out of him slowly. He groaned with each thrust. He seemed tighter than I was, or perhaps I was bigger than him. I kept it gentle and smooth until he felt more relaxed.

  When his wincing stopped and his moaning increased, I started to pound him. I gripped his hair in my hands and tugged his head back as I fucked him. He moaned and begged for me to come. “I want to feel your come inside me!”

  I threw myself against him a few more times and then I felt my body seize up. “I’m coming!” I cried and my cock blew a load right into his ass. He moaned as my white, hot come filled his tight, virgin ass.

  Then we both collapsed on the bed. I lay above him panting for a few minutes before I pulled my cock out. Then I rolled next to him on the sheets. We stared into each other’s eyes without saying a word. Our faces were stuck in permanent smiles.

  “I love you,” I told him, finally breaking the silence. He blushed and his grin widened.

  “I love you too,” he said. We held each other for a few hours before falling asleep. When we woke up, we were still half naked in our girly clothes.

  Chapter 9

  I couldn’t believe I was waking up in bed next to my best friend. We were both dressed like sissies and we had both just fucked each other the night before. I leaned in and kissed him, stroking his face. He kissed me back and I hoped that meant he didn’t regret anything.

  “How are you?” I asked him. “My ass hurts a little.”

  He laughed. “Yeah. Mine too. It was worth it though, wasn’t it?”

  I nodded. “It was the greatest feeling of my life. Outside of the moment you said you loved me.”

  “I do love you,” he said again. Then he climbed on top of me and leaned his head down to mine. He kissed me and slid his tongue into my mouth. I could still taste my come in him and it made me smile.

  “Jenny!” cried a few people from outside of the window.

  “Oh no!” I slid out from underneath John and ran to the edge of the room. I peered outside at the mob of cloaked men who were standing at my front door. They were chanting my girl name over and over again.

  “I told you,” said John. “You’re going to have to do something about them.”

  “What am I supposed to do?” I was panicking. Why did Rene have to leave? I wondered if there was any way to get in contact with her. I wanted to tell her I was leaving the cult and she could have them all back.

  “You can’t call her,” said John after I confided in him my only plan. “The guys want you. It doesn’t matter if she comes back.”

  “Fuck,” I said, adjusting my skirt. My eyes widened. “It’s this damn dress. This wig. The heels. I just need to show up as a dude again and they’ll all leave, right?”

  John shrugged. “It’s worth a shot.” I didn’t really believe it could be that simple. I didn’t really think that would be enough for these guys. I stripped myself of the dress, the wig, and the lingerie. John’s eyes watched my naked body as I uncovered inch after inch. I enjoyed his gaze on me and I couldn’t help but remember the night before.

  I dug through my drawers for the most hideous guy clothes I had. I pulled on a baggy pair of jeans and cringed at how loose they felt. I missed the tightness of the white dress. I missed having hips and breasts. I felt like an alien in my own body all of a sudden. Maybe I was meant to be a woman all along, I thought. I quickly threw on a baggy t shirt to match.

  I opened my front door and greeted the group of guys. Their jaws dropped and a look of disgust formed on their faces. “Sorry guys,” I told them. “I don’t think we should be a group anymore.”

  “Where’s Jenny?” asked one of them, as if he genuinely couldn’t remember it had been me in a dress.

  “Look. I can’t say I won’t dress up again,” I admitted to the guys who were still practically strangers. “I probably will. But you can’t keep worshipping me like this. You guys need to explore your own sexuality and stop looking for validation from others.”

  I turned behind me and saw John smiling. I spun back to the guys. “Go home. Get your lives back. Or find new ones, whichever makes you happiest.”

  They started to talk amongst themselves and I could already sense their mob energy dying down. I watched one or two of them leave and then the others got the memo. “Yeah. Sorry, Jenny,” said one of the guys.

  “I’ll see you around?” I asked him, almost sad to see the group breaking up for good. He nodded.

  “Of course. It’s a small town after all.”

  One by one the group split up and left. John came up and put his arms around my waist, resting his head on my shoulder. “So you think you’ll keep your Jenny persona?” he asked teasingly.

  I shrugged. “I want to. I don’t know how the whole town will take it. I don’t know if I’m ready to show them all quite yet.”

  “Hell, me neither,” he said. “But…maybe when we are ready…we could do it together.”

  I turned to face him and I smiled. “I’d love that,” I said.

  “Come on. Let’s go get your car.”

  I had totally forgotten about my car. It was parked just outside of the church still. John didn’t change out of his sissy clothes and I admired that he kept them on. We climbed into his car and rode to the church.

  As we pulled up I thought of everything that had gone on the past few days. It was the strangest adventure of my life. It was terrifying and new, but I ended up with a new appreciation and love for my best friend. I looked at the stained glass windows of the church and thought of Rene, wondering where she went and if she’d start a new cult.

  I reached my hand for John’s and squeezed it. “We should go shopping sometime,” I told him. “I think we could use some more girly clothes.”

  “Sounds good,” he said. He leaned in and kissed me. I got out of his car and walked to mine. It felt strange to touch the handle. It was as if I had awoken from a long dream where I was a man but I wasn’t supposed to be.

  I’m meant to be a woman, I thought. I didn’t know if that would make John and I lesbians or gay or what, but it didn’t matter. I loved him. I loved him in boy clothes and girl clothes. I loved being his little sissy. I wanted to be sexy for him and feel him fill me up with his cock.

  I also wanted to see his face every morning when I woke up. I wanted to kiss him and talk to him like we were the best of friends, because we always had been friends. Now we were more. We were so much more.

 
I got in my car and looked back at the church. As bizarre as everything had been, I didn’t regret a moment. I couldn’t help but smile to myself as I thought of all the crazy events that led me to telling John that I loved him.

  “Thank you Rene,” I said to the empty summer air.

  When I returned to my place, John was already there. We went inside together and made breakfast. Even though he was in his girl clothes, we talked like old times. I was grateful that I had my best friend back.

  After breakfast he sat on the sofa with me and we played our favorite video game. I looked over and stared at his girly body. I stood up suddenly.

  “Hey! Where are you going?”

  “Just give me a minute,” I said. I took off my jeans and t shirt and looked for the lingerie and white dress from before. I slid on the panties and the bra, then I pulled the dress up my curvy body. I didn’t even know I had curves until I put on this dress the first time.

  I looked all over for the wig and breathed a sigh of relief when I finally found it. I put it on my head and then walked out of the bedroom to meet John.

  “Oh my! Do you want to finish this game or not?” he teased. “You’re turning me on over here.” I laughed and joined him on the couch.

  “By the way,” I said, picking up my controller. “What was your girl name at the cult?”

  “Oh…promise not to laugh?”

  “Of course.”

  “Rebecca.”

  “Why would that make me laugh?”

  “I don’t know,” he said, shrugging his shoulders. “You just never know with things like that.”

  “No problem. I’m going to kick your ass in this level, Rebecca.” From the corner of my eye I saw him smiling and my heart thudded in my chest.