Man to Woman

by Jane Futa

  I nodded and smiled. “I haven’t been able to stop wondering what it would feel like…”

  “Okay.” She grabbed my hand and led me to the bedroom. She bent me over the bed like she had the girl from the night before.

  She pulled my panties to the floor and disappeared into her closet. She came back with the same dildo. “Don’t worry,” she said. “It’s clean.”

  “I trust you,” I told her. She squirted some lube into her hand and rubbed her fingers up and down my ass crack. It was cool at first and then it warmed. Just having her fingers touch me was enough to make me come, but I managed to hold off.

  She slid a finger inside my ass to get it ready. Then she slid a second one in. She moved them in and out of me swiftly and I moaned. I had no idea how good it could feel to have something slid in and out of your ass. I’d never been fingered before, much less be fucked with a cock.

  I knew the dildo would be a different story. I was a little apprehensive, but my curiosity overtook that. She warned me before resting it against my asshole. “It may hurt at first. Just try and relax as much as possible. I promise to be gentle.”

  I smiled and again said, “I trust you, Wendy.”

  I felt the tip of the cock push against my hole. It didn’t feel like it would fit inside in a million years. But the more she pushed, the more I stretched. She was right. It hurt like hell at first. I thought of her at the other end of it though and it helped me to relax.

  She almost said she loved me, I thought. I couldn’t believe I could be so lucky.

  My ass stretched wider to accommodate the girth of her thick cock. My dick started to harden the further in she pushed. I couldn’t believe it was turning me on. I couldn’t believe I had just asked to be fucked in the ass.

  She pushed in further and it started to get easier. I relaxed more and more around the hard, fake cock. She held it still for a few minutes. She wanted my ass to adjust to the giant dick inside of it. Then she pushed in further, until it was all the way inside. I couldn’t believe I had swallowed the entire thing.

  “How does that feel?” she asked me.

  “Amazing,” I said.

  “Good to hear.” She slid it back out slowly and then back in more quickly. My dick started to throb. I almost felt like I could really be a woman with a pussy getting fucked. I had no idea how fucking good anal could feel.

  I reached down and stroked my cock. She pumped the dildo in faster as I stroked. I moaned and gripped the bed sheets. I looked over my shoulder at her and she was moaning too. It was turning her on to be fucking me like this.

  When I saw her moan with her tits hanging out, I knew I couldn’t hold back. I came all over the bed with one loud groan. She smiled as she pumped the cock in and out. When she saw that I was finished, she removed it and lay on the bed next to me.

  I quickly climbed onto of her and kissed her. I moved down until my lips were around her nipples. I flicked my tongue across them. She grabbed the strands of my wig and arched her back. She moaned and writhed underneath me.

  I pushed her further up on the bed and positioned myself between her legs. I lifted her skirt, pulled her panties to the side, and pushed my head against her wet pussy.

  I licked her at the pace that she used when riding my face earlier. She still held onto my head as I swirled my tongue around her clit. She gasped and moaned.

  “You’re fucking amazing!” she cried. I couldn’t help but smile. I kept licking and sucking. Her thighs tightened around my head and she rested her heels on my back.

  I felt like the hottest little lesbian slut. I wanted to be Wendy’s woman. When I finally brought her to orgasm, I felt like I was on top of the world.

  I climbed up over her and leaned my head down to kiss her. She kissed me like she loved me. When I pulled my head back up, I could see outside of the window. She had forgotten to close the curtains again.

  There in the driveway stood my best friend Bryce. He was staring straight at us with a wide open mouth and a hurt expression. He got back into his car quickly and sped off.

  “Shit,” I said. “Bryce saw us.”

  Chapter 8

  “I’ll deal with him. Why don’t you run on home for now?” she asked.

  “Yeah, okay,” I said. I got dressed and grabbed my things. But when I was outside the front door, I realized that I was still a woman and my parents wouldn’t understand if they saw.

  I dashed quickly across the road, looking around me nervously the entire time. I ran up the stairs to my room and changed out of the women’s clothes I was wearing. I dressed myself in my normal boy clothes and felt a dirtiness creep under my skin. Boy clothes no longer felt like they belonged on me, and I didn’t understand.

  I went to the bathroom and washed off the makeup and hid the wig in a drawer. I waited anxiously to hear from either Bryce or Wendy, but neither of them contacted me all night.

  Dinner with my parents was dull and strange. I wanted to tell them that I loved crossdressing. I wanted to tell them that I was in love with Mrs. Matthews. I wanted them to know I wanted to be her trans girlfriend. I knew they just wanted me to get through college.

  I thought about the incident at the theater and decided telling them was a battle for another day. I already would have Bryce to deal with. I couldn’t take losing everyone in my life at once.

  Instead, I looked at it as an opportunity to have a little secret. It felt nice to have something that was really mine; that my parents didn’t even know about.

  The next day, I saw Bryce’s car at home. I still hadn’t heard from him or Wendy so I took it upon myself to go over and knock on their door. Before my knuckles hit the wood, however, I heard them talking faintly.

  It sounded as if they were in the backyard. I tiptoed over to her fence and pressed my ear to the white wood.

  “Is this why you and Dad got a divorce?” I heard Bryce asked.

  “No,” said Wendy. “We divorced because we weren’t right for each other. I’ve only recently started…experimenting.”

  “How many sluts have you been with?” he asked.

  “Hey. They’re not all sluts. I’ve only been with three people since your father.”

  My heart leapt for joy. So she hadn’t been sleeping around very much. Maybe I really did mean something to her.

  “Why, Neal, though? Why my best fucking friend?”

  “Because we love each other. That may be weird for you to hear, but it’s true. He makes me happy and I think I make him happy.”

  I could hear Bryce kick the dirt underneath his shoe. “It’s just so fucking weird. Why was he dressed like a woman? Why don’t you just fuck other women or something?”

  My heart sank. I worried Bryce was going to see me differently from now on. I worried that Wendy would decide she couldn’t be with me because of Bryce. A tear streamed down my cheek and I wiped it away quickly.

  “I’m not a lesbian,” she admitted. “I like a lot of different types of people. Your father was very different, but he’s the only one you agree is normal.”

  Bryce huffed.

  “I know it’s weird for you, Bryce. I respect your opinion and I’m willing to help you adjust to anything you’re willing to adjust to. I’m sure Neal won’t mind being patient with you either.”

  “You make me sound like a bigot,” he said. “I don’t care what guys want to do in bed with you. I just don’t like seeing my best friend with my mom, dressed as a woman and eating out her bare cunt.”

  “That’s understandable. I’m sorry I’m not better about closing the curtains.”

  “I’m going to go talk to Neal,” said Bryce. In a fit of panic I ran back across the street to my house. It still felt strange to be in my boy clothes. I sat on the porch and pretended I had been sulking.

  Bryce saw me and jogged over to me. “Hey, man!”

  “Hey!” I said, faking a smile and waving.

  “Can I talk to you for a second?” he asked, leaning against one of the porch columns. I
nodded and waited for the backlash. “Look, Neal. I don’t care how you dress. I just want you to know that. You’re my best friend and I’d like it to stay that way for a really long time.”

  “Me too.”

  “It was just…strange…catching you like that. It would’ve been totally different if you had come to me first and said you were trans.”

  I pushed a finger to my lips. “Could you, um, keep it down?”

  “Oh yeah. Sorry, man. Anyway, I just wanted to say…I may need some time to process everything.”

  “I understand.”

  “But-“ he said with a smile, “you seem to make my mom really happy. She was practically glowing this afternoon. And I know you’re a good guy, so…I don’t want to tell you not to see her. I also don’t want to tell you what to wear….but if you could tone it down for a few weeks or something. Just until I’ve gotten used to everything.”

  I stood up and threw my arms around him. He returned the hug. “Of course I can do that, Bryce. Everything you just said means so much to me.”

  “Hey. That’s what best friends are for.” He pulled back and shoved his hands in his pockets. “So have you told your parents yet?”

  “Oh god no,” I said with a laugh. Bryce chuckled too. “Maybe I’ll save that for next summer.”

  “Ha. Probably a good idea,” he said. “If you do tell them, let me know. I want to be there for you no matter what happens. If you decide to be all boy again too, that’s cool.”

  “Thanks, man,” I said. We looked at each other and smiled. I couldn’t believe everything that had happened. I couldn’t believe I was going to be able to keep my best friend and my new identity. Along with all of that, Wendy loved me.

  “So. Want to play some video games?” asked Bryce. “I had kind of a long day.”

  “Sounds rad,” I said. I followed him back to his house to the surprise of Wendy. “We’re going to play some games,” I told her. She smiled, not just for my happiness, but for her own too.

  I wasn’t sure what the rest of the summer would bring, but I could only hope it would be as explosive and meaningful as the beginning had been. I couldn’t wait to find out where my relationship with Wendy would take me.

  One thing I did know. I wasn’t definitely done dressing like a girl.

  Friend Zone

  Chapter 1

  I was in love with Sasha. I had been in love with her for years. She was smart, creative, incredibly funny, and I was really comfortable around her. It helped that she was the hottest girl I’d ever seen, but that wasn’t what made me love her. I’d do anything for her. My friends all joked that I was pussy whipped, but didn’t I have to be in a relationship for that?

  Sasha and I were just friends, which I was okay with. Sure, it stung when I’d see her date jerk after jerk only to get her heart broken and never consider dating me. Not that I had ever been brave enough to ask. She was the type to do all of that. She was aggressive and fearless. I was filled with anxiety and too timid to ever ask out a girl like Sasha.

  Of course, maybe that’s why she dated the bad boy types. Maybe she thought they matched her fearlessness. They were all bone heads, though. None of them appreciated how smart or caring she was. They all just wanted to bang her. I didn’t blame them, of course, but would it have killed any of her boyfriends to take two seconds to actually listen to her?

  I was Sasha’s closest friend. I was the other half of all her failed relationships. What she didn’t get from her ex-boyfriends was a friend. She needed someone to express herself to. She needed someone to share her problems with. I was always that guy.

  She even teased me a few times in a loving sort of way. She joked that I was her girlfriend and that she could tell me anything. She said I was the type to eat a tub of ice cream with her after one of her horrible breakups. It helped that we lived in apartments across the hall from each other. I could always tell when she’d gone through a breakup because her door would slam and she’d be crying.

  Strangely enough, comforting her through her breakups were my favorite moments. She’d often lay her head on my chest and I stroked her hair or her back. Sure, I was tempted to kiss her several times, but I didn’t know if she was into me. I figured if she was she would’ve told me by now.

  I loved leaning my nose in toward the top of her head and smelling her coconut shampoo on her long, blond locks. I loved sliding my hands down her back, resisting the urge to continue to her small, round ass. I bit my lip so many times while imagining cupping it and leaning down to kiss her.

  She was the subject of many of my sexual fantasies. I felt a little guilty, but I often jerked off to the thought of finally getting to fuck her. Most of the time it was harmless and simple. Sometimes, it got a little weird. Like the day we were dumpster diving and found a bright red thong. Sasha made a joke that I’d look good in it. She had stuck out her tongue to imply she was teasing, but her eyes seemed hungry as she said it.

  I didn’t want to admit it, and I never would out loud, but the way she had looked at me when she found the panties turned me on like nothing before. I’d never in a million years wear women’s clothing, but that night I went home and imagined myself in them. I pictured that hungry look in her eye and tugged on my small cock until I came. It was one of the strongest orgasms I’d ever had.

  I also would never admit that I thought about that comment nearly every day since she’d made it. I didn’t have the balls to actually try any panties on, but I wondered. At the very least, knowing how much Sasha seemed to like the idea made me curious. That was, if she liked the idea. Between her usual playful teasing and the serious lustful expression in her eyes, I couldn’t tell if she really meant it to be a joke or not.

  Another thing I didn’t want to admit was that I had the body for women’s panties. I was lender, but my ass was round. I had long, toned legs and my hips were slightly curvy. I’d been told I looked feminine plenty of times before, but I tried to be as masculine as possible because that’s what was acceptable. I often wore baggy pants and band t-shirts to hide how skinny I was underneath.

  I looked at my body in the mirror one day and imagined myself in the red thong Sasha had found in the dumpster. I knew they’d look good on me, even if I hated that they would. Thinking about them on me made my dick hard and I hated that too. It didn’t keep me from jerking off, but I was more than conflicted by it. I figured eventually it would pass and that it didn’t make me any less of a man than I already was.

  Sasha was into the big, muscular types too. One year I signed up for a gym membership with a trainer and everything, but nothing helped. I just couldn’t build any muscle. He said I had a fast metabolism or something because I could eat and eat and never gain anything. The more I worked out, the more I had to eat, until it was all I did all day. I finally gave up on all of it and sulked at my lean physique.

  I wondered, though, if it made me seem more trusting to Sasha. If it did, then I wouldn’t change it for the world. As much as I wanted to make love to her, I also wanted to be the shoulder she had to cry on. She deserved one.

  She never had many female friends and her mom didn’t understand most of Sasha’s problems. I was pretty much all she had apart from the muscle monsters she dated, and they never listened to her anyway.

  One night, like clockwork, I heard the crying and slamming of her apartment door. I sighed and looked out of my window to see a sports car speeding off. Sometimes it was fast cars, sometimes it was motorcycles. All I had was an old Honda, but my car treated me well.

  I waited a few minutes and then hopped off my couch to go see her. I knocked on her door and made up some excuse like hearing something funny online. I never let her know that I knew she had a breakup. I wondered if she ever suspected me due to my impeccable timing.

  “Who is it?” she called from behind the door. Her voice echoed since the kitchen was right next to the front hall.

  “It’s your best friend, Cory,” I said with a smile on my face.

&n
bsp; “Oh thank god,” she said, pulling the door open. Her cheeks were stained by her running mascara. Her blond hair was flipped to one side with a few strays as if she’d quickly run her hand through it. Her nose was bright red from crying.

  “What’s wrong?” I asked, feigning ignorance and holding out my arms. She ran into them instantly and began sobbing.

  “It was horrible. It was my worst breakup yet!”

  “With Josh?”

  “Jacob,” she said, mid-sniffle. I stroked her back and laid my head on top of her head. We stood like that for a minute or two before she invited me in.

  We moved to her living room couch and sat beside one another. She tucked her legs in close to her body and grabbed one ankle in her hand. She had dark red lipstick on that was starting to fade. Despite my intentions on listening to every word of her frustrations, the lipstick reminded me of the red thong. My mind kept trying to pull away from the discussion and back to my curiosity that was still unaddressed.

  “And then he called me a fucking bitch! Can you believe that?”

  “No!” I said, hoping to sound convincing. Normally she had ever ounce of my attention, but this time I couldn’t be sure what had happened before Jacob called Sasha a bitch.

  “After everything that asshole did,” she said. I listened closely hoping she’d repeat herself, but she didn’t. “Anyway, good riddance, am I right?”

  I nodded. “Mmhmm.”

  “I need some fucking ice cream,” she said, quickly hopping from the sofa. She ran into the kitchen and pulled out a giant tub from the freezer. She grabbed two spoons, one for her and one for me, and returned to her seat. We both started to dig in and I smiled. She was only inches away from me.

  “Oh! And another thing-“ she said, waving her empty spoon at me. “My next photo project is required to have models in it so that I can show my competence in photographing them.”

  “No way,” I said while lifting my eyebrows. Sasha was in school for photography. She took some of the most amazing photographs I’d ever seen, but her relationships often got in the way of her work. She frequently looked for models who would pose for her but most of them never worked out so she stuck with landscapes as much as possible.