Man to Woman

by Jane Futa

  Lady in a Taxi

  Chapter 1

  “I’ve just been so stressed at work lately,” I confided in my best friend, Jacob. “It’s like I put in so much effort for no reward.” I leaned back against the patio bench and inhaled the warm, summer air. My yard was lined with pine trees and the sky’s light was slowly disappearing. The sun had fallen behind the horizon minutes ago.

  “When was the last time you got laid, Brad?” asked Jacob. He leaned forward, peering at me over his sunglasses which he no longer needed. He continued to wear them to feel cool. He wore a baseball cap that had his favorite beer logo on it rather than the logo of a sports team. His t-shirt clung to his back and his legs were spread wide enough for him to lean on.

  “Shit,” I said as I thought about his question. When was the last time I’d been laid? “I guess not since Darlene,” I admitted. Darlene was my ex-girlfriend. I had always thought I loved her and she loved me, but our relationship grew stale pretty quickly. The sex hadn’t been good for over a year, and that was when we had it at all.

  “Man. That’s been months since the breakup,” said Jacob. What he didn’t know was that it’d been months before the breakup that I even fucked her. I remembered it reluctantly as the least fun night in bed I’d ever had. It had been clear to me by that point that she was tired of me, but I wasn’t brave enough to be the one to break it off. Eventually, she came to me and told me she was leaving. She couldn’t take me anymore and wanted more excitement in her life.

  I’d told her I wanted excitement but she never wanted to do anything but watch reality TV at home. She took the insult as her cue to leave and didn’t bother fighting back. I watched her walk out of my front door, leaving me with a strange half emptiness. I was half glad she was gone and half miserable to be alone.

  “I guess it’s been a while,” I admitted. “You really think that’s my problem?” I asked him.

  “Definitely. I mean. Work sucks, but if you’re not getting laid on top of it?” I nodded. His ideas made a lot of sense. “Let’s go out and get wasted tonight. Maybe you’ll pick up a hottie or two,” he said. I laughed. Or two. I knew I’d be lucky to even get one glance in my direction.

  I wasn’t unattractive by any measure, but I was a miserable man. I knew girls could pick up on that from a mile away. I hadn’t always been this way, but my relationship with Darlene had made me bitter. When I first hooked up with her I thought she’d be the one. I thought we would get married and settle down and have the perfect life. I was glad it went south before we were tied together by marriage, though.

  “I guess it couldn’t hurt,” I told him. I looked down at my wrinkled work clothes and told him I was going to change. I went inside, splashed water on my face and put on deodorant. Then I picked the most hip, yet sophisticated outfit I could find and dressed myself. When I was ready, I returned to Jacob and we decided on a bar. Then we called a taxi.

  Chapter 2

  The bar was crowded, but I didn’t mind. The noise and commotion helped to take my mind off of my troubles. I wanted to lose myself in the busy nothingness of the bar. Jacob was talking my ear off as usual and I half listened. He pointed out several women for me to hit on, but there was always something about each of them that put me off or made me feel insecure. Ultimately, I was about to give up on the night completely.

  “Well if you’re not going to go after that blond over there, I think I will,” he said with a crooked smile. He was still wearing his sunglasses even though it was well into the evening and we were indoors.

  “Be my guest,” I told him, assuring him I lacked any interest in the blond.

  “You going to be alright over here by yourself?” I nodded with a disgusted expression. He was more condescending than he needed to be, but I knew he was only kidding. He slapped my back a few times and then turned toward the blond. I watched him for a moment before letting my eyes wander through the mass of people swerving around me. I set my glass on the bar and lifted my eyes straight ahead.

  That’s when I saw her. The most unique girl I’d ever seen in my entire life. Her long, brown hair flowed down over her shoulders as she sipped from her glass. There was nothing between me and her except the entire bar. I caught glimpses of her in between the gaps of rushing bartenders and spinning bottles of alcohol. There was just something about her that I couldn’t place. Something I realized I desperately needed.

  She was different than the other girls. I wasn’t sure how. Her breasts were small, and she was taller than my past girlfriends. It was her face. She had striking features and hard lines. Her eyes sparkled under the dim bar lighting.

  I tried to decide how I’d make my move. I craved her and wanted to take her home with me, but I didn’t want to put her off.

  Nice night, I practiced in my head. No, that’s foolish. She’d be bored instantly.

  Before I had the chance to come up with a backup line, she was gone. My eyes scoured the bar for her. I can’t have lost her already. I never got the chance to introduce myself.

  That’s when I noticed a tall, slender woman sliding into the seat next to me. It was her, the strikingly sexy lady from the other side of the bar. Her dress was cream and flowed from her hips. It clung to her body in all of the right places, showcasing her fit physique.

  “Hello,” she said in a flirty, yet somewhat deep voice. “I’m Catherine.” She extended her hand and I slid mine into it.

  “Brad,” I said, unable to take my eyes off of her.

  “I caught you staring at me,” she said with a raised eyebrow.

  “Oh. Sorry about that.”

  “I don’t mind. I like the attention.” She winked and shifted a shoulder toward me flirtatiously. My heart started racing. Then she laid a hand on my thigh and whispered, “Let’s say you and I get out of here.”

  I couldn’t believe my ears. She barely knew me and already wanted to fuck me? At least I’d hoped that’s what she meant. I looked back toward Jacob and noticed he was talking it up with the blond. I waived toward him and he gave me a thumbs up. I turned back to Catherine and nodded, dumbfounded by my strange turn of luck. She took my hand in hers and pulled me toward the front doors.

  She hailed a taxi and we slid into the backseat. I watched her ass as she climbed in before me. All I wanted was to run my hands up the bottom of her skirt and pull her hips to me.

  “Where to?” asked the driver. Catherine told him an address I didn’t recognize and then shifted her gaze to me. “Don’t tell me you’re single.”

  “Just went through a bad breakup,” I admitted. I was surprised at how easy it was to be open with her so quickly. I didn’t know anything about this girl but she already had my full attention. I wanted to give her anything and everything.

  “Allow me to help you forget her,” she said, leaning across the seat. She pressed her lips to my ear and swept her tongue across it while gliding her hand up my thigh. Once she reached my erection, she whispered, “Oh my. Big man.”

  I leaned back on the seat and sighed. She caressed my hard cock through my pants until I couldn’t take it anymore. I reached for her shoulders and brought her in for a kiss. I pressed my lips to her hard until I felt her body quiver.

  It had been a long time since I kissed a woman this attractive. Darlene had nothing on Catherine, and I knew Catherine was probably too good to call me the next day. I didn’t care. Any moment with a girl like Catherine was a moment to treasure.

  I let a hand travel down to her chest and then I squeezed. She moaned softly as I brushed my fingers over her nipples. I brought my other hand to her hip and let it slide down to her bare thigh. She caught it and stopped me from pursuing. “Ah-ah,” she said teasingly.

  She moved my hands above my head and then started to unfasten my jeans. Shit. We can’t do this in a taxi. I looked at the driver who was either ignoring us or blissfully ignorant. My heart pounded in my chest and my ears were ringing with heat. Are we really doing this? Right here? I let Catherine continue to work my
pants and briefs down until my cock was free.

  Her eyes grew wide and she licked her lips. “Yummy,” she said. She lowered her head and opened her mouth. I can’t believe I’m going to get sucked off in a taxi by a sexy woman!

  She wrapped her wet lips around the head of my cock and flicked her tongue under it. I groaned but tried to keep silent. I peeked at the driver again who still hadn’t noticed us. Then I watched Catherine lower her head, eventually taking in all of me.

  This is crazy, I thought as she bobbed her head up and down my cock. I brought a hand to the back of her head and cupped it to make sure she was real. Catherine slid a hand inside my briefs and massaged my balls while she sucked me. It was torture not to cum right there.

  Catherine pulled off and stroked my cock a few times while kissing me. Her tongue tasted like milk and honey. I massaged her small breasts again and then tried sliding my hand back toward her waist. This time, she didn’t stop me.

  My hand reached her bare thigh and slid under her dress. A strange feeling came over me as I reached closer toward her panties. Something was brilliantly different about Catherine, but I couldn’t figure out what it was.

  Then I found it. My fingertips grazed along silk panties with a small cock tucked in them. She must’ve felt my surprise in our kiss because she pressed harder. That’s why she seems different, I thought.

  I’d never been with a trans girl before, but the way she handled my rock hard dick didn’t make me want to stop. I brushed my knuckles against her tiny cock and she smiled through our kiss.

  She reached under her dress and slid her panties down her legs. Again I looked at the driver but never met his gaze. She spit on my cock and stroked it before climbing in my lap. Then she slowly lowered herself until her asshole met my cock.

  She leaned down and slipped her tongue in my mouth again to distract me. Then she lowered herself further, until I felt the head of my cock slide into her tight little ass. I grabbed her hips as she sank further down. Moments later, I was filling her up and I could feel her balls resting against my pelvis. The tip of her tiny cock just barely touched my abs. Then she circled her hips around.

  I groaned again and looked at the driver. He has to be ignoring us at this point, I thought. It didn’t matter. I had stopped caring.

  Catherine worked my cock like a pro. She rocked her hips back and forth, dragging her tiny cock across my stomach. She lifted up and down on my dick as much as the small cab would allow.

  I reached for the top of her dress and pulled it down. Then I took one of her nipples in my mouth and flicked my tongue across it. She moaned quietly and rode me harder.

  Shit, I thought. I’m going to cum right here in this cab. But before I could, Catherine climbed off of me again and sat beside me. She zipped up my pants but left her panties on the floor. Then the taxi came to a stop.

  “That’s me,” she said, ushering me to exit with her. I paid the taxi driver and stepped out of the car followed by Catherine.

  “Don’t you want your panties?” I asked as the cab drove away.

  “I leave those there for Brent,” she said. “So he lets me fuck in the back of his car.”

  “So he knows?”

  “Of course, silly. You didn’t think we could get away with that otherwise?” She laughed at me and pulled my hand to hers. I looked down and could see the tiniest erection through her skirt. “Naughty boy,” she said when she caught me looking.

  She pulled me up a flight of stairs to a dark apartment and pushed open the door. I followed her in, unsure of where the furniture was. Then I felt her bend over something and raise her skirt up. “I want you to fuck my little asshole like the slut I am,” she said.

  The way she talked dirty to me got me instantly hard again. I quickly stripped off my pants and briefs and stroked my cock. I ran a hand over her gorgeous ass and gave it a little spank.

  “Harder,” she said. “I’ve been such a bad girl.”

  My cock swelled and I spanked her harder. She screamed from the pain, “Yes! Yes!” I spanked her again and then pushed my cock into her ass. “Oh, fuck! Your cock feels so good!”

  I pushed my cock in and out of her, spanking her ass every few thrusts. My eyes started to adjust to the darkness and I saw that she was bent over a couch. I pulled my hips back and forth, slamming into her as deep as I could.

  As I pounded her little asshole, my balls swung against hers which filled me with a new euphoric delight. I grunted as I thrust. Catherine’s screams only grew louder.

  Before long I shot a hot load into her ass. I thought I would cum forever as it seemed never-ending. She moaned as I filled her asshole with my cum and then I collapsed over her.

  After I caught my breath, I pulled out of her slowly and felt my load spilling out of her. She turned around and dropped to her knees. “Allow me to clean you. I deserve as much punishment as you can give.”

  I nodded and she lowered her mouth onto my cock. She licked her tongue up and down my shaft until my cum was cleaned off. Then she stood up and kissed me.

  I felt a small pool of my own cum slide into my mouth as she circled her tongue around me. Then she moved her lips to my ear and whispered, “I made a little mess of my own. Would you clean me?”

  I nodded in a euphoric daze and then dropped to my knees. I lifted her skirt up until I found her tiny cock which was covered in cum. She must’ve shot a load onto the couch, I thought. I opened my mouth and took her two inch long cock into my mouth. I sucked it clean and then I licked her balls. She moaned and caressed my hair as I licked her.

  Then she pulled my head back and ushered me back up. “Thanks for the fun,” she said, handing me my pants.

  “Thank you,” I replied, sliding my briefs and jeans back up my legs. “When can I see you again?”

  “I’m afraid I only do one night stands,” she said with a wink. “You understand.”

  Unfortunately, I did. Ever since my breakup all I’d had were one night stands. Catherine, however, was worth sticking around for. I nodded again and she leaned in for a kiss.

  “You’re my favorite fuck,” she said as she walked me to the door.

  “Back at you,” I said.

  “Don’t forget me, okay?” She opened the door and I stepped outside.

  “It’d be impossible to forget you,” I told her.

  She closed the door and I looked around her complex trying to contemplate everything that’d just happened. I just fucked a hot chick with a dick, I thought. A cool breeze blew past me and I watched the traffic in the street die down.

  I descended the stairs and hailed another taxi. To my surprise, Brent picked me again and I slid in the backseat. On the floor lay Catherine’s panties.

  “Those are for you,” said Brent with a wink. I reached down, picked them up and held them to my face. They smelled like her tiny cock and her gorgeous ass.

  “Thanks,” I said as I slid them into my pocket. I told Brent my address and looked out the window one last time toward Catherine’s apartment. Maybe she’ll get my address from Brent and come find me one day.

  A guy can dream…

  Chapter 3

  To my surprise, the next morning I woke up to a knock on my door. I expected it to be Jacob. I rubbed my temples as I contemplated how I would apologize for abandoning him the night before. How would I explain what I abandoned him for? I figured I’d never see Catherine again anyway, so maybe it would just be my little secret.

  When I opened my door, however, Catherine stood there in a sensual and sexy sundress. “Hope you don’t mind,” she said with a wink. “I felt something special between us. I brought breakfast, if you’ll have me.”

  I nodded, still in a sleepy daze. I pulled my door open wide and watched her gorgeous body glide past me. She set a white paper bag and two coffees on my kitchen counter. “I hope you like pastries,” she said.

  The longer she stood before me, the more awake I felt. I walked up to her, wrapped my arms around her waist, and pulled her
in for a kiss. I inhaled her scent and I could still smell our sex from the cab on her. She was intoxicating and I couldn’t get enough. She kissed back, pushing me against the counter passionately.

  I pushed her back across the kitchen to the counter opposite us. I gripped her hips and lifted her ass onto the counter. I reached under her skirt and tore her panties to her ankles. I tossed them to the floor and then slid my hands up her thighs. She arched her head back against the cabinet and moaned.

  I couldn’t believe I was with her again. I couldn’t believe she found out my address from Brent. I was so grateful. I wanted to show her just how grateful I was.

  I unfastened my pants and dropped them to the floor. My erection stood tall, despite finally getting laid the night before. I lifted her skirt so that I could see her cock as I slid mine into her ass. She blushed and I could tell she was still slightly embarrassed about what she was.

  I wrapped my hand around her cock and stroked her as I pumped in and out of her ass. I watched her slide across the counter as we fucked. She closed her eyes and dropped her jaw as I brought her pleasure she clearly hadn’t felt in a long time.

  I kept stroking her dick and slamming into her ass. I caught myself and slowed down. I wanted to do it right. I wanted to treat her like the best thing that had ever happened to me, because she was.

  I slid in slowly and carefully. She looked down at me and bit her lower lip. She leaned her forehead against mine and our eyes stared deeply into each other. We rocked our hips together gently, daring ourselves not to kiss but instead to watch the other’s expression as we came.

  I started first. My balls swelled and my cock exploded deep into her ass. When she felt my warm liquid shoot up, she couldn’t hold back any longer. I felt her shaft quiver in my hand. Her bulbous head burst a hot white pool up against my shirtless torso. I felt her come cover my chest and I couldn’t keep myself from kissing her. I leaned in, pressed my lips to hers and felt them melt against mine.