Man to Woman

by Jane Futa

  I reached with shaky hands for the bow around my neck. I pulled the strands and felt the neck start to loosen and sag. The cloak fell around my shoulders and dropped to the floor. Everyone had seen that I was an imposter. Everyone saw that I was still dressed like a man.

  Rene clicked her tongue. “What an imposter,” she said. “Imposters get punished if they don’t join.”

  I looked to her with wide eyes. “What sort of punishment?”

  She leaned in until her lips were nearly touching my earlobe. “You don’t want to know.” I swallowed hard. “John! Join us, please.”

  He came quickly and apologized repeatedly for bringing me. “John, you don’t have to apologize,” I told him.

  “It’s alright,” said Rene, holding up her hand to silence him. “But he needs some clothes to wear, don’t you think?” John nodded his head and I felt my heart beat faster. “I hear you keep a spare bag with you. Is that true?” John nodded again. “Go and get it. Let’s show Greg here, how to comply with the rules of being a sissy.”

  John ran quickly from the church. I knew he was headed to his trunk to grab the duffle bag I’d seen the day before. It felt so long ago. I couldn’t believe there was a time when I didn’t know this group existed.

  The seconds ticked by slowly and quickly at the same time. I could hear my heart beat over the sound of murmurs from the other guys. My palms were sweating and my fists were clenched. I watched John run back in with his duffle bag, trying desperately not to fall in his heels. As he ran, the middle of his cloak blew open, revealing another stunning lingerie outfit underneath.

  He was wearing something akin to a nighty in royal blue. His stockings were white and the stilettos that were desperate to trip him up were white. He ran up to the center of the circle and leaned over to catch his breath. He dropped the duffle bag beside Rene and took a step back.

  Rene smiled and stroked his cheek. She leaned down and kissed the top of his head. “Good girl,” she told him, throwing me off guard. Sure, he was dressed like a girl, but he wasn’t actually a girl.

  She turned to me and told me to strip. “What?” I said, still in disbelief of what was happening.

  “You either strip or you get the paddle and the whip,” she told me, narrowing her brows at me. Is she for real? This whole thing is totally nuts!

  Nevertheless, as if my hands had minds of their own, they started to lift my shirt from my torso. The guys licked their lips and sat on the edge of their seats watching me. My hands moved to my shorts but they hesitated. There was no way I could take off my pants in front of a room full of guys.

  “John, help your friend,” said Rene. John looked at me awkwardly and blushed. I felt my own cheeks heating up at the thought of him undressing me. My mind quickly dashed to the night before when I had jerked off to the thought of him sucking my cock. I couldn’t let him take off my pants.

  “It’s okay,” I assured her. “I got it.” John exhaled. I wondered if he had been nervous to undress me for the same reasons I was. Maybe he just thought it’d be too weird. Then again, nothing about this entire experience was normal so far.

  I dropped my shorts and revealed my boxers to everyone. I kicked off my shoes and stepped out of the bunched fabric around my ankles. I noticed everyone’s eyes widened and I looked down to find my cock was stiff and lifting my cotton boxers upward. I blushed. I couldn’t hide that I was turned on. I couldn’t much of anything.

  “Look here!” called Rene. “He likes it! Maybe he does belong here.” She teased me, pointing out my erection to the room. Then, in one swift motion, she tugged my boxers down to my ankles.

  I was horrified. My erect cock was fully visible to everyone. A few of the guys were stroking themselves like they had to John the day before. Oh my god. What is happening? I was horrified, but my body was filled with lust. I kept telling myself to run but something inside me planted my feet to the floor. Curiosity. Emptiness. Desire.

  “Time to play dress up,” said Rene with a crooked smile. Her eyes sparkled as they gazed on my cock. “We need to hide that tiny dick of yours.”

  My cheeks heated up again as the guys snickered around me. I wanted to hide myself but the snickering intoxicating. Did I actually like being humiliated?

  Rene leaned over the duffle bag and pulled out the silk panties I recognized from the day before. “Why don’t you put these on your friend,” she told John, handing them over to him. He swallowed and then took them hesitantly. He was reluctant to dress me and I was reluctant to let him. But part of me wanted him to put the panties on. Part of me hoped his fingers would brush against my legs and make me quiver.

  He whispered an apology and then bent over. He stretched the fabric out for me to step into. I slid one foot in and then the other. I closed my eyes when John started pulling the panties up my thighs. I felt the cool silk brush against my leg hair and I moaned. I heard Rene snicker but I didn’t care. This was the sexiest experience of my life, even if it was a little weird.

  I looked down to find John’s face inches from my cock. He stared at it longingly before wrapping his hand around my shaft. Oh fuck, I thought. I wanted him to take me into his mouth. I wanted him to suck me dry. But he only lifted it so that he could secure the panties around my hips. Hips I didn’t even know I had.

  He sighed, pleased he had finished the hardest part. I wondered if he wanted me as badly as I wanted him. I hoped he did, though I knew I’d probably never find out for sure. He reached into the duffle bag for a matching bra and stood up to put it on me. He slid the straps up to my shoulders and I looked around the room. A few of the guys were stroking themselves to the sight of me in lingerie. Of course, they had two sissies to look at this time.

  I looked back at Rene who seemed pleased with herself. She folded her arms across her chest and held her head high as she watched down the length of nose. Her hair fell over her shoulders, and her large breasts were trying to escape her tightly fitted top.

  I thought about how badly I had wanted Rene the day before, and how strange it was that today I wanted John. Maybe I really was gay. Maybe I wanted to be a little sissy, just like John. Maybe I wanted him to be mine.

  John reached in the bag for a tight fitting dress with a short skirt. It was white with skinny straps. He unzipped the back and I stepped inside of it. He scooted it up my hips and zipped it back up. Then he pulled out a pair of black heels. I loved how striking the black heels were against the white fabric. I slid my feet into them, and instantly felt transformed.

  In an instant, I had gone from man to woman – male to female. I couldn’t believe how feminine I felt inside a pair of heels and a tight dress. I looked down at myself and gasped. It wasn’t my body. It had to be someone else’s. It looked just like a woman!

  John reached in the duffle bag again. I watched eagerly to see what he’d pull out next. It was a wig. I cocked my head in confusion. Some of the other guys wore wigs but John didn’t. I wondered why. He placed the wig on my head. It was long, straight, and blond. It fell around my shoulders and curved around the padding from the bra. I felt beautiful and sexy. Every head in that room was turned toward me. Every expression was filled with desire.

  I looked back at Rene who seemed…jealous. I wondered what was going on through her head. She stuttered as she spoke, “Now to anoint him!” The room cheered with eager applause. I didn’t remember hearing applause at John’s anointing. I looked at him and he blushed, stepping backward and hanging his head down.

  Rene ordered me to get to my knees. She was no longer smiling. I dropped, awaiting her punishment. She whispered something to John. I assumed she had asked him to grab the anointing dildo from the day before. Instead, I watched him lift up the skirt to his nighty and pull out his very hard cock.

  “Wait…what’s going on?”

  She leaned down and pressed her lips to my ear. Her breasts hovered directly in front of my face. “If you’re going to be a little attention whore and steal all of my praise, then you’re go
ing to get a real cock shoved into your throat.”

  “What? What do you-“ but I couldn’t finish. She had grabbed me by the throat and pulled my jaw down. She ordered John to put his cock inside. He looked at me with desire and a hint of regret. I wanted to tell him how much I wanted him. I wanted to tell him it was okay. I didn’t want him to think he was hurting me or ruining our friendship.

  I’ll show him, I thought. I’ll give him the best head anyone’s ever gotten. I stuck out my tongue to show that I was willing. His face relaxed, though he looked confused. He laid his cock on my tongue and I fell into a daze. It was the most amazing feeling in the world.

  I wrapped my lips around his head and began to suck. He moaned and leaned his head back. I loved that I could give my best friend pleasure. He looked so hot in his little girly outfit. I wanted to make him come harder than he ever had.

  I reached around and grabbed his ass, pulling him into me. I swallowed his whole cock until it slid down the back of my throat. He looked down in awe and stroked my cheek. The whole room was watching, but it felt like it was just me and John alone.

  I realized in that moment that I loved John more than I ever knew. I wanted to be with him. I wanted to make love to him. I wanted to be his little sissy and him to be mine. I wanted to care for him and protect him.

  Out of the corner of my eye I saw Rene panic. This wasn’t what she had been expecting. She didn’t want me to like it. She wanted to force something unpleasant on us. But I loved it and I loved John.

  Soon he was spilling his come into my mouth. I swallowed every single drop. My own cock exploded come into my white dress. I felt the warm pool of liquid cover my stomach. John removed his cock from my mouth and panted, looking at me inquisitively.

  I turned to the room and saw that every single guy had their cocks out and were coming. They all had skirts lifted up to their hips and their cloaks dropped to the side to expose them. They stroked simultaneously, as if it were some ritual. I watched them all start to come, one by one.

  It was strange having a room full of men come to me sucking my best friend’s cock, but I liked the attention. I turned back to Rene and saw an angry expression. She tried to bullshit that this is what she wanted, but I noticed that everyone had finally stopped listening to her.

  Instead, they all kept looking at me, as if I was the new Rene. It infuriated her, but I was the one they desired now. I was the most seductive woman in the room. She called the evening to an end and demanded we all leave. She said we didn’t deserve her spiritual guidance.

  “What do you want us to do, Greg?” asked one of the men. I looked at Rene who looked as if she wanted to punch me.

  “Go home, guys. We’ll meet back here tomorrow.” I watched them all instantly stand and leave one by one. Rene stormed off without so much as an insult or goodbye.

  John grabbed his duffle bag and started to leave. I grabbed his shoulder and spun him around. “John. Can we talk?”

  “Uh- keep the clothes,” he said, and then he ran quickly out of the door. I’d never felt so fulfilled and so empty at the same time. I went home wearing my new clothes and tried to process everything that had happened.

  I sat on the edge of my bed and pressed my fingers to my lips. I can’t believe I just sucked my best friend’s cock.

  Chapter 6

  I woke up the next morning with a dizzying sensation. I could hardly remember the remnants of my life from before. I didn’t know where I stood with John, and I wasn’t sure what was happening with the sissy group now that I had angered Rene. Everything seemed to be falling apart as quickly as it had come together for me, and I still hadn’t found my happiness.

  I dressed myself in the sissy outfit from the day before, but this time I was able to study my reflection. I danced in front of the mirror in the corner of my room, twisting my hips in the tight fitting white dress. I slid the wig on and brushed it around my shoulders, playing with where it fell. I suddenly wished I had makeup. I wanted to wear the same bright red lipstick I had seen on John a few days ago.

  Then I thought of John again. I thought of his red lips wrapped around the fake cock and I thought of my lips wrapped around his. God he is sexy in everything he wears. I couldn’t deny it anymore. I was falling in love with my best friend. But I was uncertain as to how he felt about me, and I was worried I had ruined all of this for him.

  I put on my heels and wrapped the cloak around me. Then I drove to the church for the daily cult meeting. Everyone was there except for John and Rene. I didn’t care to be there without the two of them, but I decided to go inside and wait. I figured John was late or something.

  I sat with the other guys in the half circle of chairs, but all of their eyes were turned toward me. They even started moving chairs around to complete the circle, so that I was suddenly at the head position.

  “What name do you want to go by, Greg?” asked one of the guys.

  “What do you mean?”

  “Everyone here has a feminine name. A sissy name. What’s yours?”

  I thought about it. I’d always liked the name Jenny. “Jenny, I suppose,” I said with a shrug, keeping my gaze locked on the front entrance to the church.

  “Jenny. Do you have any wisdom for us? The guys and I decided to make you the new Rene.”

  “What? Oh no. I couldn’t,” I said, but their eyes just stared at me lovingly. They were all on the edge of the seats, listening intently to my every word.

  “Jenny?” asked one of the guys. “Which one of us will you punish today?”

  Another guy asked, “Do you want to fuck any of us?” I was confused by their sudden interest. They all seemed to want to share me the way they had shared Rene. I loved the adoration, but my focus was solely on John.

  “What’s John’s female name?” I asked the group of guys. They all shrugged. It seemed as if they didn’t pay attention to each other the same way they paid attention to Rene. My eyes returned to the door. I saw John peek his head in and then quickly leave. I couldn’t take it anymore. I jumped from my seat to chase after him.

  The group of guys followed me. They started calling after me, trying to get me to stay. I saw John standing by his car with his arms across his chest and his head bowed.

  “John!” I called but the group of sissies surrounded me. They all started touching my body and I couldn’t get to John. They carried me back into the church and laid me on the floor, forming a circle around me. I watched them all pull out their dicks and start stroking over me.

  I would’ve thought it was hot if I wasn’t so concerned about John. Unfortunately, there was nothing I could do. They weren’t going to let me leave. They were used to getting a show, and they were determined to get one.

  Suddenly, I heard John’s voice yelling over them. He pushed his way into the circle and shoved some of the guys back. He reached for my hand and pulled me to my feet. We both ran quickly to his car, leaving the guys behind.

  He drove me home, but didn’t say anything. I couldn’t get out of his car until I knew how he felt. “I’m sorry,” I told him. “I’m sorry that I ruined your happiness.” The silence grew between us. I started to feel like I really had ruined everything.

  “Why’d you have to show up to these meetings anyway?” he asked.

  “I don’t know. I guess I just missed you.”

  Chapter 7

  “You didn’t even like the idea. You laughed at it,” he protested.

  “I know. I was wrong. Can we talk about what happened?”

  “Now they all want you. I guess you’ll just be the new Rene,” he said with an acidic tone. I couldn’t tell what he was angrier about: the fact that Rene had disappeared or the fact that everyone wanted me instead of him.

  “I didn’t mean for any of this to happen,” I replied. He looked at me with big, sad eyes.

  “I know you didn’t. How can I blame you?” His eyes scanned my body from head to toe. “You put on that dress and wig and became the hottest chick there. Sissy or
not, you are so much more beautiful than Rene.”

  My voice strained in my throat. “Thank you.” I wanted to tell him that I was falling in love with him. I wanted to tell him how much it meant to me that he found me beautiful. I was frightened. I still wasn’t sure how he felt for me on an emotional level. I didn’t want to push too hard and end up pushing him away completely.

  “I guess I was just jealous,” he continued. I kept my lips tightly closed and just listened. “I was jealous of how beautiful you looked. But I was also jealous that all the guys wanted you.”

  “Did you want them to want you?” I asked.

  “Sort of,” he said honestly. “But I mostly wanted you for myself.” He quickly covered his mouth as if the words slipped out without his permission.

  “What? Did you mean that?” I asked. He looked away shamefully. I reached across the car and turned his face toward mine. “All I’ve wanted is you this whole time,” I admitted finally.

  He looked as if he didn’t believe me. “I don’t understand,” he said.

  “I came to this stupid thing to save you. I missed having you as my best friend. I missed hanging out with you. Then I saw you suck that cock…” My heart started to race as I spoke the words. It was more difficult to admit than I had imagined. “John…I jerked off to the thought of you sucking that cock.”

  His eyes widened but he didn’t say anything. I continued. “Then, yesterday…when I was forced to suck yours…John-“ I wanted to tell him it was the best thing that had ever happened to me. I wanted to tell him it was the greatest moment of my life. I wanted to say that I’d do it again and again happily. I wanted him to know how much I wanted to please him.

  I didn’t get a chance to say any of it. He leaned over and kissed me for the first time. I realized how strange it was that I’d sucked his cock without kissing him first. I enjoyed kissing him almost as much. His lips pushed against mine and his tongue slid into my mouth. He tasted sweet and intoxicating. His skin smelled of warm sunlight and faint floral perfume. Rene was far from my mind. The cult was far from my mind. For the first time in days, I stopped caring about my old life.