Man to Woman

by Jane Futa

  For all I knew she was a virgin. I knew I should feel guilty about the possibility, but I couldn’t deny myself of her hot little body. I thought about how wet her pussy must be.

  I watched her slide up and down my cock, her hands resting on my thighs. I peeked to where I thought her pussy would be beneath her dress and my heart stopped.

  I couldn’t be sure, but I thought I saw the faint outline of a hard cock poking through her dress fabric. I would’ve stopped her if I could’ve, but her tiny mouth felt so good on my hard cock and she was just starting to get the hang of sucking it.

  I analyzed the shape protruding from her dress. There’s no way. No way in hell this slender, seductive woman has a dick between her legs. I looked at her feminine face and tried to reassure myself. I watched the uncertainty in her eyes; that virgin uncertainty. She has to be full woman. There’s just no way.

  I leaned my head back to distract myself and relaxed into Lily’s soft, wet mouth. I grabbed her head with both hands and started to fuck her mouth faster, until my balls were slapping against her chin.

  “Oh fuck! I’m going to cum!” I cried out. I let go of her head in case she didn’t want my cum in her mouth but she kept sucking. I grabbed hold of the couch cushions and released a huge load into the back of her throat. She struggled to swallow everything but I saw white streams spill from the corners of her mouth.

  When I finished, I wiped her chin and she licked my hands clean. She stood up slowly and I was nearly face to face with her hard cock. No fucking way.

  “I better get back before Marla starts to wonder about me,” I told her.

  “Yes, of course,” she said, looking slightly embarrassed. I stood up next to her.

  “Thanks for the relief,” I said. My eyes searched hers. I wanted her to know I was grateful. “See you tomorrow, hm?”

  She smiled and batted her eyelashes again. “Of course.”

  I leaned down and kissed her forehead before leaving. I knew once I left the guest house I’d have plenty of time to process what I saw between her legs.

  Did I really just let a dude suck me off?

  Chapter 3

  The walk back to the house felt longer than usual. I couldn’t believe that our sexy housemaid was a man underneath the tight clothes. What confused me more, though, was how much her dick was actually turning me on. I rushed into the house, desperate to feel something normal.

  The food Marla prepared was dull. Our conversation was an overwhelming bore. I stared at my plate, pushing food across it hopelessly.

  “Are you alright?” asked Marla with only a fraction of the enthusiasm a wife should have. I knew deep down that she didn’t really care if I was alright.

  “Yeah,” I said, never lifting my eyes from the plate. My stomach turned at the thought of eating one more bite of her cooking. I couldn’t stop picturing Lily’s hard dick under her dress. I felt strange about it. All I wanted to do was slide my hand between her legs and touch it. I wondered if she liked her dick being touched or if she liked to pretend she had a pussy instead. I couldn’t believe there was never going to be a Lily pussy for me to fuck.

  That leaves other options though… Wait! What am I thinking? I’m not going to fuck a dude in the ass. That’s…gay, right? I looked up at Marla, hoping for some renewed chemistry, but she was empty and tired. I knew she was only with me still for the money.

  “I’m going to bed,” she said after a few more silent moments.

  “I’ll go with you,” I said eagerly. She looked surprised but shrugged her shoulders. She turned around and I slapped her on the ass. “Want to fuck?” I asked unromantically.

  She turned her head over her shoulder. “I don’t know. I had a long day.”

  “Just a quick one,” I said.

  “Fine. Make it quick, though.”

  I rushed up to the bedroom and lay with Marla in bed. I lifted her nightgown and pulled her panties down. I ran a finger along her slit to warm her up but she seemed utterly bored by everything. I spit on my bare dick and stroked it a few times. Then I pushed it into her.

  She may as well have been half-dead. She even yawned while I pumped myself inside of her. I grabbed her tits, again attempting to turn her on more but she just brushed my hands away.

  I decided to use my imagination. I was desperate to prove to myself that I wasn’t gay. I grabbed her hips and thrust myself in and out of her. I closed my eyes and thought back to Lily sucking me. Then I focused on the outline of her dick again.

  I ran my hands between Lily’s thighs until I felt her long shaft. Then I stroked it as her beautifully feminine face lowered over my dick. Then I spun her around and fucked her ass just like she was a tiny, virgin woman. She moaned like a woman and begged for my cock like a woman.

  I opened my eyes to see Marla half asleep. I pounded her a few times quickly until I felt my cum spill into her. Then I pulled it out and watched as she rolled onto her side without her panties.

  “Goodnight,” she said.

  “Goodnight,” I said, feeling unsatisfied despite the orgasm. I dressed myself and lay in bed next to Marla until I fell asleep. I was suddenly looking forward to seeing Lily again the next day.

  Chapter 4

  The next morning I woke up to an empty bed and the sound of a vacuum in the hallway. Marla had already left for work and the bedroom door was cracked. Through the crack, I saw Lily walk back and forth with the vacuum in her hands.

  She was delicately bent over it as she pushed it forward and pulled it back. She was wearing denim mini shorts and a white t shirt. I could see the padding from her bra poke out of her shirt similarly to the blouse she wore before.

  My cock hardened as I watched her. She turned her head and saw me staring. “Good morning, Mr. Parker,” she said.

  “Call me, James,” I reminded her.

  “What?”

  “James!” When Marla realized she still couldn’t hear me, she shut the vacuum off. “Call me, James,” I said again.

  “Oh right,” she said, twirling a loose strand of her dark hair in her hands. Her glasses fell slightly on her nose and I wanted to reach out and push them back up. “I wasn’t sure…you know. After last night…”

  “That I wouldn’t want you to be informal?”

  She nodded meekly. “Nonsense,” I said. She smiled and that familiar pink returned to her cheeks.

  “Well, I guess I should return to my chores,” she said without moving a muscle. She seemed like she was waiting for something, so I took it upon myself to make a move.

  “Why don’t you start by making the bed,” I said. She cocked her head to the side as if trying to decipher my meaning. I slid out of bed and pointed to the wrinkled sheets. She walked toward Marla’s side of the bed and leaned over. She pulled the sheet and comforter taught and smoothed out the wrinkles.

  I stared at her gorgeous body as it bent over and waited eagerly for her to make it toward my side. She smoothed her way down to the bottom of the bed and then walked to my end. Her body brushed past me and her rose perfume swirled around me.

  Then I watched as she slowly bent over to smooth the sheets again. I stepped up behind her and hovered my hand near her thigh. I shouldn’t be doing this. I shouldn’t be fucking my maid, and I definitely shouldn’t be fucking a dude. But I was more attracted to Lily than any woman I’d ever seen before. She was intoxicating and delicate.

  She stood up slowly and turned her head just over her shoulder. My hands were pushed out in front of me, inches from her waist. They were eager to grab her and pull her close to me.

  “If you want to touch me, you can touch me,” she said in a low, seductive whisper. That was all I needed. I swooped in and wrapped my arms around her waist. She leaned her head to one side, exposing the tendons on her neck. I leaned my mouth in and kissed along the skin.

  My hands traveled up to her bra and squeezed the padding as if real breasts were there. She moaned and my cock hardened against her ass. My hands traveled down her abdomen slo
wly, in search of the hidden member that she had between her legs. As my fingers reached the waistband of her shorts she grabbed them tightly.

  “I should tell you-“ she started, but I interrupted her.

  “I know,” I whispered. She gasped but released my fingers. I slid them down to her thighs and then inward until they found her half-hard cock.

  She reached behind her and found my dick. She stroked up and down and I stroked along her. I groaned in her ear and she gasped repeatedly.

  I moved my fingers to the top button of her denim shorts. I unfastened them and slide them down her long, slender legs. She kicked them off past her Keds and I noticed she was wearing a purple thong. I ran my hands along her thigh and up to her ass. Then I grabbed each cheek in one hand and gave her a small spank.

  “Oh!” she cried in a wonderfully delicate voice. I reached back around to her cock and stroked it again. It was small and I could see how easily it could be hidden.

  As I stroked her, she lifted her t shirt over her head. She tossed it to the bed and dropped her hands back by her side. Her bra was purple as well and I wondered how I didn’t see the color through her white shirt.

  I moved my hands to her lower back, dragging my knuckles slowly up to the clasp of her bra. I unhooked the fabric and slid the straps down her arms. She dropped the bra to the floor and then turned around. For the first time, her body looked boyish to me and I could clearly see the outline of her hard, tiny cock through her panties.

  But her face and hair was the same elegant and feminine look. I reached my hand to her cheek and pressed my lips to hers. She slid her tongue into my mouth and swirled it around. She slid her fingers into my boxers and pulled them down, kissing my chest and abdomen along the way.

  My cock sprung out toward her face and she giggled. Even her giggle was feminine! She dropped to her knees and wrapped her fingers around my shaft again.

  I watched this boy-woman open her mouth and wrap her lips around my head. Then she flicked her tongue along the underside, sending my head spinning. I ran my fingers through her soft dark hair and pushed her further down my cock.

  She sucked in like a vacuum and moved her head back and forth. I stared at the cock in her panties while she sucked. What the fuck am I doing? I couldn’t believe I was letting a dude suck me off again, but I couldn’t stop. And nothing was better than seeing Lily’s gorgeous face taking in my hard dick.

  She pulled off with a pop! and smiled. Dick or no dick, I still wanted to take her. I wanted to grab her body and pound her over and over again. I grabbed her hips, kissed her hard, and then spun her around.

  I leaned her over on the bed and she braced herself with her forearms. I slid her thong strap to the side and stared at her beautiful ass. I spanked her again and then lowered my face to her cheeks. I stuck out my tongue and licked along her asshole. She cooed like a woman and from my angle, she was all woman.

  I stood up and stroked my cock. I spit on the shaft and stroked it again, until my saliva covered every inch of me. Then I stepped forward, resting the head of my dick against her asshole.

  Before pushing in, I traced her entrance with my finger. Then I slid it in slowly. She moaned with pleasure so I moved it back and forth. I could see her small balls hanging below. I reached out and fondled them as I fingered her asshole.

  “Fuck,” she moaned. I kept massaging and fingering her, and she rocked her hips back and forth like a woman. I stared at her ass and couldn’t keep from fucking it any longer.

  I pulled my finger out and grabbed my cock. I pushed the head into her hole slowly, feeling it stretch and tighten around me. She moaned with pain and pleasure.

  “Oh fuck!” I groaned once my head popped all the way in. I eased into her slowly until my cock was all the way in. My balls hung against her balls which sent a wave of electricity through me. I grabbed her hips and pulled out slowly.

  “Mmm,” she moaned. I pushed back in again. Once she seemed more relaxed, I started thrusting with more force. I was careful with her, but eager to pound her like in my fantasies.

  “You like that, my little slut?”

  “Yes, sir,” she said.

  “You were pretty naughty, trying to fool me into thinking you were a chick.”

  “Yes I was, sir.”

  “I’m going to have to punish you for that,” I said.

  “Yes please. Punish me, Daddy.”

  “Fuck,” I groaned at the sound of her calling me Daddy. I spanked her ass and pulled my cock almost all the way out. Then with full force I slammed it back into her, my balls slapping against hers.

  I pumped my cock in and out of her tight little asshole quickly. I leaned over her and placed my hands on either side of her while I thrust my hips into her. She had her head turned to the side with her hands up by her face. I moved her hands above her head and held her wrists.

  Then I leaned into her ear and whispered, “You’re going to get the pounding of your life.”

  She looked both frightened and excited. Her eyes sparkled and her cheeks flushed red. I kept her wrists in one hand and placed my other on her hip. I slammed into her ass over and over until I thought my head would explode.

  Then I looked down at her stomach and noticed a stain forming at her side. Fuck. She just came! I started to pound her harder and faster, over and over again. I grunted and groaned and she moaned with a tinge of pain.

  Before long, I was unleashing my hot load deep inside of her. Her gorgeous, pouty lips hung open as I filled her. I gripped her hair in my hand to make sure she stayed in place while I finished.

  When I caught my breath, I slid my cock out of her slowly and watched a waterfall of white hot cum spill from her asshole. I reached out and rubbed it along her balls. Then I pulled her thong strap back and secured it in place.

  Lily sat up and looked at me with those gorgeous brown eyes. “Are you going to tell Marla about me?”

  I thought for a moment, knowing full well I never told Marla anything. “I’ll keep your secret if you keep mine.”

  “What secret is that?”

  “That I fucked you.”

  “Oh yes. That,” she said looking to the side. “Will you be fucking me again?”

  “Lily, I want to fuck you every day that you live with us.”

  The corner of her lips lifted up into a smile and her eyes sparkled again. “I’ve never been anyone’s mistress before. It makes me feel sexy.”

  “Lily. You’re the sexiest person I’ve ever seen.”

  “You don’t mind my…” she said, looking down at her groin.

  “It makes you sexier,” I said, lifting her chin up toward me. She stood up quickly and wrapped her arms around me.

  “I promise to satisfy you as long as I’m able,” she said. She dropped to her knees again and took my cock in her mouth one more time. She licked it clean of her ass and my cum, moaning pleasantly while she did so.

  I stroked her beautiful face with my hand and watched her delicate tongue glide along my cock.

  “Fuck,” I moaned, starting to get hard again. “Go do your chores so I can interrupt you,” I said.

  She pulled off my cock and smiled. We both got dressed and Lily went back to her housekeeping.

  My job for the rest of that week was to watch her clean until I couldn’t take it anymore. Then I would I grab her and throw her on a piece of furniture and fuck her brains out.

  It was the best vacation of my life.

  Dressed as a Babysitter

  Chapter 1

  I was 19 and needed a job badly. College only racked up expenses and I needed to work nights so I could still make my classes during the day. Unfortunately, the only night jobs I could find where warehouse and stocker positions, and I was pretty thin and lanky for a boy. I knew manual labor would not be my forte.

  I needed something more delicate and easier on the joints. Something where I could showcase my winning personality over my rugged muscles (which I had none of). I knew I’d be better suited for a
customer service position, but there weren’t many customers in my town that stayed up past ten.

  I racked my brain for over a month as I watched the college bills pile up. I lived on ramen and diet soda, pinching pennies the whole time.

  I knew there had to be something out there for me, but what? That was when I noticed an entire section of job listings on craigslist for babysitters and nannies. For some reason, everyone preferred women for the job. How sexist, I thought to myself. Sure, I’d never really dealt with kids before, but how hard could it be? They’d mostly be asleep the whole time.

  So I started going to interviews. With no references and a boyish body, I was turned down repeatedly. It seemed that most moms just didn’t trust a teenage boy without references watching their kid.

  So I had an idea. If they were looking for a woman, why not trick someone into hiring me? After all, I was dainty enough. My build was slender like a fashion model and I was sure I could pull it off. No one would have to know, I thought. I’d only wear the women’s clothes during work.

  It was as good as settled in my mind. I just had to get my hands on some clothes. I’d never worn women’s clothes before so I didn’t have any lying around. I did have a younger sister back home though, and fortunately my school was only an hour away. I decided to drive back home over the weekend and wait until my sister left to raid her closet.

  This is the perfect plan, I thought. What could go wrong?

  Chapter 2

  “What are you doing home, loser?” Emma asked as I walked in the door.

  “Shut up, sis, or I’ll pop you one.”

  “With those twigs for arms? Ha!” She took a bite out of her sandwich and plopped herself on the couch. Emma had always been glad to see me go off to college. We didn’t hate each other, but we had the sibling rivalry bit down well. Her sour attitude was only making the idea to raid her closet more pleasant.