Man to Woman

by Jane Futa

  “Sure. Ok.”

  She helped me remove the blue blouse and slipped the yellow one on instead. The yellow blouse had ruffled sleeves and a v-neckline. It was soft and relaxed and a little simpler than the blue one. As she slid it over my head and I felt it fall to my waist, I felt instantly transformed. I couldn’t have felt more like an incredibly sexy woman in that moment. That is, until she added the heels.

  “Gorgeous,” she said. “Damn. You’re making me want to fuck you.”

  My eyes widened and my cock hardened. She’s just teasing. I can’t fuck my roommate’s little sister. She laughed when she saw my expression and then crouched down again to put the heels by my feet.

  “Oh. And we’re going to have to shave those legs.” I nodded and stepped into the heels which fit me like Cinderella’s glass slipper. I felt like a princess with a fairy godmother. A wave of gratitude swept over me.

  “Thanks for doing all of this,” I told Nina. I had just realized how she could’ve laughed at the idea and turned me down. Instead, she was full of good humor and helping me transform into a woman.

  “No problem. I love playing dress up,” she said, her blue eyes beaming up at me.

  Me too, I thought.

  Chapter 4

  Nina taught me how to shave my legs and do my makeup. She had even brought a medium length dark-haired wig with her for me to try. By the time she was finished with me, I felt more like a woman than I ever thought possible, and I was starting to get comfortable with it.

  I had everything I needed for the interview. I was scheduled to meet with a woman named Mrs. Hutchens. When I heard I’d be interviewed by a woman, I found myself growing more nervous. Certainly another woman could tell that I wasn’t one of them?

  I sat in the waiting area of the Choodle lobby, tapping my feet nervously. The receptionist didn’t seem to notice anything strange about me which helped me breathe a sigh of relief. I heard my heel clicking against the linoleum floor and the sound soothed me.

  Bright sunlight poured through the tall lobby windows. I watched as people passed by on their way in and out of the building. A few people stared at me when they caught sight of me, but again, no one seemed suspicious.

  It’s fine. You totally look like a woman, I told myself. I tried to reassure myself as much as I could. I tried to remind myself that this wasn’t for anything but a taste of what Choodle wanted in an applicant.

  But I was kidding myself. The longer I wore Nina’s red lingerie, the more I fell in love with feeling it against my skin. Now that my legs were shaved, I loved sliding my thighs together and feeling the smoothness. I knew that even if I dressed as a boy the rest of the time, I was going to have a few moments alone in my red lingerie.

  I had distracted myself enough that I didn’t hear when the receptionist had called my name. She had to get up from her desk and walk over to me. “Mrs. Hutchens is ready to see you,” she said.

  I nodded, picked up my folder with my resume and followed her to the elevator. We rode up six floors before I was instructed to exit. She pointed me down a long, gray hallway and showed me the door to Mrs. Hutchens office. I thanked her and began the nervous walk down.

  When I finally reached her door I lifted my fist to knock, but I hesitated. What the hell am I doing here? I looked down at my tight pencil skirt and heels and I thought about my red panties. There’s still time to get out of it. There’s still time to go home and pretend none of this ever happened.

  As if my body was disconnected from my thoughts, my knuckles tapped on the large, wooden door. There was a name plate that read “Hutchens” across it. Then I heard her voice. A soft, but strong voice.

  “Come in,” she said. I opened the door slowly, ready to turn on my heel at any moment and make a run for it. I stepped inside and watched her eyes lift above her glasses while she kept her head tilted down.

  When she finally looked me over, she stood up and smiled. Then she walked closer to me with her arm outstretched. “Ah! You must be Bella.”

  “Yes,” I said as I reached out my own hand. I shook hers firmly, something I’d learned a long time ago to do in interviews. But I must’ve shaken it too firmly because she eyed me suspiciously. My heart pounded in my chest and I wanted to flee.

  “Have a seat,” she said. I walked toward her desk and watched her ass sway in her plaid skirt. Again, I was thankful to have a small cock so that she wouldn’t see my erection.

  I sat down and so did she. She folded her hands underneath her chin and leaned her head on them. “So, tell me a little about yourself.”

  Everything from this point on was a lie. I couldn’t tell her about my previous job titles in case they checked up on me. Of course, I thought. I already put them on my resume and application. I tried to talk only about things other than my previous gigs.

  “Let me be honest with you,” she said suddenly. “We don’t care what you do or how you’re educated. We only care about one thing.”

  My body quivered as she spoke. “Wh-what’s that?”

  “That you’re a woman.” I was shocked. This was the most sexist and illegal interview I’d ever been to.

  “What do you mean?”

  “You are a woman, aren’t you?”

  I nodded, squeezing my legs together tightly and pulling my skirt down as if I could hide underneath it.

  “Well. You’ll have to prove it.”

  “Prove it? How?”

  “You’ll have to show me your pussy,” she said.

  My jaw dropped. Is she serious? No respectable woman, real or not, would let themselves be subject to this.

  “I don’t think-“ but she held out her hand to stop me.

  “Let me be honest with you, again,” she said. “I know full well you’re not a woman. I know you’re just trying to take advantage of the fact that we want to diversify here at Choodle.”

  “What do you-“

  “Did you really think I wasn’t going to call your references before scheduling an interview? They’ve never heard of Bella White.”

  “They’re just…um…” I felt adrenaline race through my veins as I tried to come up with a good excuse. All I could do, though, was chastise myself for thinking I could get away with any of this. What a horrible idea. What a horrible plan! Now you’ve done it!

  “So go on. Show me what’s under your skirt.”

  “I think I need to leave now,” I said, finally getting up the courage to march out of there. But before I could reach the door she had rushed up behind me. I saw her stretch her arm across me to place her hand on the door, keeping it closed. Then she cleverly slid between me and my only exit, looking at me with coal black eyes.

  “You’re not going anywhere,” she said. “Take off the skirt.”

  With no other option in sight, I reached for the zipper of my skirt. You don’t have to do this, I told myself. But part of me wanted to. I couldn’t figure out why, but my body was yearning to expose myself the way I had with Nina. I unzipped the skirt and let it drop to the floor.

  Mrs. Hutchens’ eyes traveled down to my groin, where my tiny hard cock rested inside my lacy red panties. She smiled in a silent laugh and then covered her mouth with her hands. Then she burst into laughter, letting her hands swing at her sides.

  “You’ve got to be kidding me!” My cheeks flushed but my cock only got harder. She walked up to me and reached her hand out. Her fingers slid between my soft thighs and she leaned her lips in near my ear. “You’re going to pay for trying to cheat the system.”

  Before I could respond, her hand was resting on the outline of my hard cock, and her thumb was gliding up and down my shaft. My jaw fell open and my eyes closed. I heard a moan escape me and startle me.

  “How are you going to punish me?” I asked finally.

  “I’m going to show you what happens to cross-dressing sissies. If you want to be a woman in this world, you’re going to get fucked like a woman.”

  I wondered what she meant. It wasn’t like she had a
dick. Or did she? I looked down at her skirt to try and find a hidden erection, but it was flat as could be.

  “Get on your fucking knees,” she instructed. I did as I was told and stared at my skirt on the floor to the side of me. My hands were shaking but my cock was throbbing. I was terrified and terrifyingly curious at the same time. What the hell was this woman about to do to me?

  I heard her heels click on her way to her desk. She slid out a drawer and pulled something from it, but my back was to her so I wasn’t sure what it could be. Then I heard it slide shut again and her heels click on her way back to me.

  She kneeled behind me and pushed her lips to my ear again. “Close your eyes,” she said. I closed my eyes and heard her stand up. She moved in front of me and then I pressed a finger to my lips. She slid it between them and against my tongue. It was soft and delicate, like the lingerie I was wearing.

  Then she tugged on my jaw until my mouth opened. “Keep your eyes closed,” she whispered. I waited for a small eternity to finally know what she was up to. Then I felt it. A silicon cock slid into my mouth and rested against my tongue.

  “Show me how badly you want this job,” she told me. Shit. Was the job still on the table? Very confused and even more aroused, I wrapped my lips around the fake cock and sucked my cheeks in. I felt her hand stroke the side of my face as she slid it in deeper toward my throat. “That’s a good little slut. That’s my good sissy boy,” she cooed.

  I sucked harder to show her how aroused she was making me. She started pushing it in and out with more force, until I felt it slamming against the back of my throat. Eventually I started to gag on it, and she seemed to be enjoying the show. I opened my eyes to plead with her, but she was staring intently at my mouth. I felt my saliva spill out of my mouth as she fucked my throat with her silicon cock.

  When I could hardly breathe, I pulled myself off and collapsed on the floor. “Come on now,” she said. “You can’t possibly think you’re finished?”

  “Mrs. Hutchens,” I started, gasping for air. “I can’t take it anymore.”

  She held the cock up to her face and turned it in her hand, surveying its every ridge. “Well then,” she said. “We’ll just have to find another hole for it.”

  My mouth gaped open at her suggestion and my eyes were wide. There was only one other hole in me. My ass. I couldn’t believe what she was suggesting. At the same time, I wondered what it would feel like. I’d never had so much as a finger in my ass, much less a cock. Was she really suggesting I get fucked for the job?

  “Walk to the desk and bend over,” she said, slapping the dildo against the palm of her hand. Her feet were straddled wide like she was ready to deliver some serious punishment to me if I didn’t do exactly what she said. I wiped my mouth and stood up. I walked to her desk with quivering legs. I placed my hands on the desk and bent over so that my ass was exposed.

  She walked toward me. “Good girl,” she said, giving my ass a little spank.

  She reached over and pulled my red lace panties down, exposing my tight virgin asshole. Then I heard her spit and rub it over the silicon cock, moaning as if she could feel the pleasure. I can’t believe I’m about to get pounded in the ass by a Choodle manager, I thought to myself. I exhaled and bit my lip as I waited. I was never so excited or curious to feel anything in my life as I was now.

  Mrs. Hutchens moved her finger up and down my crack, resting the tip in the center of my asshole. Then I felt her push in slowly.

  “Fuck,” I cried out as the tip of her finger entered my tight ass.

  “It’s only going to get more intense from here,” she warned.

  I nodded as I felt her dig her finger in.

  “Good girl,” she said, sliding her finger in a little further. My ass eagerly opened up for her. She pulled it back out only to thrust it in again, picking up the pace as she went on. Soon, she slid in a second finger and I felt my ass stretching around them.

  “This is to get you ready. You’re still a virgin, I’m guessing?”

  I nodded again. I lifted my fist up to my mouth and bit my knuckles. I couldn’t only imagine what was about to come.

  I moaned with her as she fingered my ass. My body writhed with anticipation. She pulled out her fingers and reached around to my face. “Suck them clean, sissy,” she said.

  I opened my mouth and wrapped my lips around her fingers. I could taste my virgin hole on her skin and I was just about ready to come. My cock grew harder and the head of me swelled.

  She slid her fingers in and out of my mouth over and over. She pulled their wet tips along my cheekbones. She spanked me and moaned as she did so. Then I felt her hands on my ass, massaging me. With each new slap I moaned helplessly. She spread my cheeks apart and then lay the shaft of her cock between them.

  “You ready to see what it’s like to be a woman?” she asked me. I nodded and closed my eyes. She dragged the cock down so that the tip rested at my asshole. She slowly pushed in the head and I felt my ass stretch as wide as possible.

  “Fuck!” I cried, knowing it was just barely in and there was much longer to go.

  “Ah-ah,” she said, spanking my ass. She continued to push and I felt my ass pulse and stretch around the silicon cock. My body tensed at first and then finally started to relax into it. The deeper in it went, the better it started to feel.

  I groaned with pleasure and pain. The cock was sliding all the way in and I felt her quaking body pressed against me. “You like getting your tight virgin ass penetrated?” she asked.

  “Yes,” I gruned.

  “Good,” she said, slowly withdrawing the cock from my ass. I felt my hole relax again, but only for a moment. Soon she was pushing back in with a little more speed this time. Then she pulled out again. I could feel my legs quiver as I neared orgasm, but I wasn’t sure if I was allowed to come.

  “I want you to come for me, you little sissy slut,” she commanded.

  “Okay.”

  “Beg for it,” she said as she started pumping my ass faster. I felt her body slam into mine as she shoved the cock deep inside me.

  “Please let me come,” I begged.

  “Louder,” she commanded.

  “Please let me come!” I squealed as she thrust into me over and over. Mrs. Hutchens moaned as she pushed her body against mine and it felt so good to play the dirty little slut. I couldn’t believe I was getting my ass fucked and enjoying it.

  “Come for me,” she said in a low growl. She pounded my tight little ass faster and harder and I closed my eyes while fully relaxing into my part as the sissy slut.

  “Fuck!” I cried as I shot my load all over her desk and probably her paperwork. She pumped my ass over and over while my come spilled everywhere. She grabbed my ass and I felt her body quake above me. She was coming too.

  “Shit!” she yelled, collapsing above me. She had the cock shoved deep inside me as we both came simultaneously.

  When our bodies had finished shaking, we both held our positions while we caught our breath. She ran her hands over me, giving my ass one more spank before finally pulling out. My asshole relaxed in the absence of her cock and I collapsed on the floor.

  She stood above me, panting. “What have you learned today?” she asked.

  “Not to dress as a woman for a job,” I told her.

  “No. But if you dress as a woman, prepared to get fucked like one,” she said. I nodded and stood up to grab my skirt. While I’d enjoyed the sex, I knew the job wasn’t possibly still available.

  “Where are you going, Bella?”

  I turned my head in surprise. “I figured…”

  “You thought wrong,” she said, sitting at her desk. She held up a few come soaked papers and shook her head. “We need diversity. Now I can’t hire you as a woman, but I can hire you as a trans woman.”

  I neared her desk with my ear toward her. What was her plan?

  “Are you prepared to be a little sissy the duration of your employment here?”

  I thought abo
ut it for a half a second before realizing that being a little sissy was what I was meant to be. I nodded. Nothing would’ve made me more proud.

  “Great. Then let’s get you this job,” she said with a smile. “Of course, there may be a few extra activities I’ll need from you…if you get my drift.”

  “Nothing would bring me greater pleasure,” I told her.

  “Just what I wanted to hear,” she said.

  I went home that night still reeling from the day’s events. A week before, I was Brent the lanky programmer with nothing to offer the world. But now, I was Bella, the trans woman with a secure job at the world’s top search engines.

  When Jason saw me walk in the apartment, he started laughing. “Sorry, man,” he said. “How’d it go?”

  “I got the job,” I said with a smile on my face.

  “No shit! What are you going to tell them?”

  “I told them I’d take it.”

  “But how are…what are…” he stumbled looking for the right words.

  “I hope you like the outfit,” I told him. “Because I think you’re going to be seeing me wear these things a lot more.”

  His jaw hung open as he processed my statement. “Well, good for you man!” he cheered on.

  “It’s girl, from now on,” I told him.

  “Sorry, man- I mean girl. That’s going to take some getting used to,” he said, shaking his head.

  “I’m a patient person,” I told him. Then I set down my things, went to my room and lay on my bed. I stretched my arms down the length of my body and ran my hands along my outfit, taking it all in.

  What a fucking trip! I thought. I pictured myself working at Choodle in a short little pencil skirt, and I couldn’t help but smile the biggest smile of my life.

  Dressed for the Bachelor Party

  Chapter 1

  My buddy Jay was an idiot. He was about to get married and give away his card to the singles club. There was too much pussy in the world to tie himself down to one person, and I just didn’t get it. But when he asked a guy he’d only known for six months to throw his bachelor party, I couldn’t help but take offense. I was his best friend of ten years. I was the king of all things party related. I was going to be his best man, for fuck’s sake. Isn’t it the best man’s job to throw the craziest, wildest party for the groom? After all, it was going to be his last night of new pussy. Did he really want Ben to handle it?