Man to Woman

by Jane Futa

  My dress was now pulled down to my waist and up around my hips, bunching just over my hard but tiny cock. When we reached the desk, he slowly bent me over it and I quickly grabbed my cock and balls so they were as hidden as possible.

  I felt Lyle rest the shaft of his cock between my ass cheeks while he rubbed my back. He pumped his cock through my cheeks a few times and groaned. He sounded like an animal again and I knew he was going to cum quickly.

  He licked his finger and then played with my asshole. He slid his finger in slowly and I moaned. My cock was covered in fabric and rested against the desk. Every movement that I made stroked my cock slightly and I knew I might cum. Maybe I can keep it hidden, I thought.

  Lyle removed his finger and then spit on his cock. Then he pushed the head of his huge dick into my tight ass. A shot of pain ran up my spine as he stretched my virgin ass.

  “Oh fuck!” I cried out, causing Lyle to moan with pleasure.

  “You ain’t seen nothin’ yet,” he said. Then he thrust into me with full force which pushed my body up a few inches on the desk. I grimaced as his cock filled me completely and his balls nearly touched mine.

  Then he pulled out slowly and slammed back into me. He grabbed my waist and started to pound me, over and over. Each time he thrust into me my cock shifted against the dress and the desk. I bit my lower lip, preparing to cum when he did.

  He slapped his pelvis against my ass, spanking it between thrusts. “That’s a good little stripper slut. You’re going to make daddy so happy,” he said.

  “I hope so,” I said, finally starting to relax around his cock.

  “You’re going to be my prize slut. I can’t wait to show off my baby to all those horny guys.”

  “Fuck,” I moaned as he pounded me harder.

  “Are you going to make Daddy proud?”

  “Mmhmm,” I moaned.

  “That’s my good little girl,” he said, stroking my hair.

  I grabbed the edge of the desk for support as he slammed into me. Soon his body tensed and the head of my cock expanded.

  “Fuck!” he cried. I felt a hot load shoot deep into my ass which made me cum too. I tried desperately to keep the cum in my dress and hoped Lyle wouldn’t be able to see through it. Fortunately for me, Lyle was almost always drunk so it would be fairly easy to get away with.

  When Lyle finished cumming, he pulled himself out of my ass and licked it until it was clean. Then he pulled the thong back up and spanked my ass again.

  “Now get back to work, slut.”

  When he was focused on his pants, I quickly stood up and surveyed my dress. There was still a stain that could be seen. Shit! I finished dressing my top half and then ran from his office. Angela saw me sprint down the hallway and her jaw fell open when she saw my stain.

  “What the-“ she said, staring with wide eyes.

  “Angela. I quit,” I said suddenly. I darted out the front door before she could question anything.

  When I got to my car, I peeled out of the strip joint as fast as I could and raced home. Then I called the chief and told him what I’d learned.

  “Shit. Looks like we got another guy to chase down. Good work, Rick.”

  “Thank you, sir.”

  “Hang on to the clothes. You never know if we’ll need you to go undercover to catch his partner.”

  “Will do.”

  We hung up the phone and I leaned back on my couch. I stared down at my stain covered dress and smiled.

  Maybe I’ll get to do this again, I thought. I took a sip of my beer while I imagined fooling another man into thinking I was a woman.

  I knew this was the most fun I’d had as a cop since I started. Who knows. Maybe I’ll dress like this on my off days. Just for fun.

  A smile crossed my face at the thought. So much fun.

  Trapped by the Maid

  Chapter 1

  The outline of Lily’s bra showed through her sheer blouse. I wondered if she knew I could trace the lines of her bra with my eyes or not. I knew I shouldn’t be looking like I was. Lily was our live-in maid and my wife, Marla, was very fond of her. But I was still a man, and Lily had the hottest body I’d ever seen. The things I’d do to her if I was single…

  I shook the naughty thoughts from my head and focused on my emails. I was off work for a week since my boss forced me to use up my accumulated vacation time. Despite that, I still checked work emails frequently in case an emergency came up. Marla worked at a nearby restaurant and was unable to get time off, so I was unfortunately stuck at home for the week.

  However, after watching Lily meticulously clean the house in her sheer blouse and tight black shorts, I decided it might not be such a bad thing to be home after all.

  “Excuse me, Mr. Parker,” said Lily as she brushed her tight body against the side of me to reach the hutch. “I need to dust a few things over here.”

  I bit my lower lip and clenched my fists to keep from grabbing her waist right then and throwing her on the kitchen table. I scooted my chair a few inches and lamented when her rose perfume faded from the distance.

  “Please, call me James,” I said.

  She didn’t look at me but I caught her cheeks flushing light pink and her eyelashes batted with nervousness. “Alright…James,” she said. I watched her stretch her long, slender body to reach the top of the hutch. She flicked her wrist quickly so the duster in her hand danced elegantly along the wood.

  Everything about Lily was seductive and I wondered if she was trying to be sexy on purpose. I never saw her much before since she lived in a small studio on our property. Though, I admit to peeking through her windows on occasion. She was horrible at drawing the curtains closed and I had the perfect view from our guest bathroom.

  I’d peer out our window and watch her undress. She always wore the sexiest lingerie compared to Marla. I even stroked my dick to the sight a few times, but none of that was intentional on her part. Now, however, it seemed as if she were trying to get my cock hard.

  That’s ridiculous. She wouldn’t risk her job to sleep with me. I chalked it up to a typical male fantasy and returned to my emails.

  Then she bent over. Her ass was suddenly inches from my left shoulder as she dusted the lower shelves of the hutch. I peeked through the sides of my eyes and let my gaze wander over the curves of her cheeks. I noticed a small amount of ass dipping below the hem of her shorts.

  I clenched my teeth. It took everything in me to keep from sliding my hand up her inner thigh until it brushed along her slit. If I had my way, I’d stand behind her, rip her shorts down and fuck her from behind. I imagined her gripping the edge of the hutch for support as I pounded her over and over.

  My cock became noticeably hard and a small wave of panic swept through me. “Excuse me,” I said, staring at her perfect ass one more time. I stood up and rushed to the nearest bathroom to get rid of my hard on.

  Once in the bathroom, I pulled down my pants and boxers and whipped out my hard cock. I leaned my head back and stroked the shaft slowly.

  “Mmm, fuck,” I moaned to myself. I thought of Lily’s dark hair pulled back into her tight bun. I thought of her black frame glasses which only made her face sexier. She had a small pointed nose and pouty red lips. I imagined her lips wrapped around my cock and gagging on it.

  “Yeah. You like that slut?” I whispered to myself. I remembered watching her through the window as she’d take her top off. She unbuttoned it slowly, revealing a white lace bra. Then she unclasped that and dropped it to the floor.

  I imagined her tiny tits bouncing up and down as she rode my cock, her wet pussy cumming all over me. That’s a good little bitch, I thought. This will teach you a lesson about seducing your employer.

  I thought of her bent over the hutch, me running my hand up her thigh as she moaned with delight. I imagined her pushing me away but ultimately succumbing to what she desired. I ripped her shorts and panties down and slid a finger into her wet cunt. She moaned and pleaded but I continued.

>   Only when she was about to orgasm did I stop and then I rested the head of my cock at her pussy entrance.

  I stroked my cock harder over the bathroom sink. Every thought of Lily sent a heat wave rolling underneath my skin. I spit on my dick and stroked faster.

  That’s my good little slut. Tell me how badly you want it. I imagined her begging for my cock, still bent over the hutch. Then I gave it to her. I slid my cock all the way into her tight little virgin pussy. Then I pulled it out and thrust it back in. I started to pound her until every loose thing on her body bounced in rhythm to my thrusting. I watched her tits shake each time my cock filled her up.

  Moments later, thick white ropes shot out from my dick into the sink. I bit my lip to keep from moaning too loudly. That’s my good little slut, I thought, picturing her licking up every drop. I braced myself by placing one hand on the mirror. I caught my breath and looked at my reflection.

  What the hell are you thinking? You can’t picture your maid like this. But what could be the harm? It was just a private fantasy after all…

  I cleaned up and then returned to the table. My coffee was getting cold so I picked up my mug and headed into the kitchen. When I turned around, Lila was there washing dishes. Her tight little body was standing between the sink and the island countertop. I knew I could walk around the island to get to the other side of her, but I didn’t want to.

  I walked up beside her, said, “Excuse me,” and shimmied past her ass. For one split second, my cock was inches away from her beautiful ass. My eyes rolled into the back of my head with the image of grabbing her hips, but I made it to the coffee pot safely.

  “Coffee’s cold,” I told her.

  She looked at me with one large dish in one hand and a sponge in the other. She smiled and blushed again. I loved watching the little pink specks form on her cheeks. I saw her wrinkle her nose adorably.

  “Do you have an itch?”

  “Yeah,” she said with a laugh. Without completely thinking, I moved toward her. The sunlight spilled through the kitchen window and caressed her soft skin. I reached my hand up and lightly scratched the end of her nose. “Thanks,” she said, her round hazel eyes looking up at me. The tension was palpable. Her tiny breasts were inches from my chest. If I brought my hand down in just the right way, I knew I could brush it accidentally against her nipple.

  I stood by her completely frozen in her gaze. I loose strand of dark hair fell across her face. I gently lifted my fingers to her hairline and combed it back behind her ear.

  Then, as if someone were yelling at me, I snapped out my trance. I took a step back and turned around to grab my coffee. “Well then,” I said. “There you go.”

  As I left the room, I swore I could feel her gaze on my ass. This is going to be one long fucking week, I thought.

  Chapter 2

  I avoided Lily as much as possible for the rest of the day. I was bored out of my mind so I spent most of the afternoon doing yard work. When my wife came home I hugged her close to me and kissed her forehead.

  “What’s wrong with you?” she said, confused by my elaborate and unusual display of affection.

  “Nothing,” I said. “I was just terribly bored today.”

  “Lily didn’t keep you company?”

  “What? Of course not. Why would you-“

  “Wasn’t she around to clean the house?”

  “Oh,” I said when I finally understood. “Yes. Yes she was. But we were frequently in different rooms.”

  “Okay…” said Marla with one raised eyebrow.

  I wrapped my arm around her waist and pressed my lips into hers. I tried to lose myself in our kiss and escape my thoughts of Lily, but it failed. The harder I kissed Marla, the more I imagined pounding Lily’s tight little pussy.

  Marla pushed me away. “You really need to get back to work,” she said. “I’m going to go get out of this uniform.”

  I watched Marla strut down the hallway. I loved my wife, but her body didn’t excite me as much anymore. Not when a hot little thing like Lily was always around.

  I went out to the yard to grab the lawnmower before the sun completely set. From where I left it, I could see inside one of Lily’s windows perfectly. She was wiggling her tight body into a new black dress. I could see the muscles in her back tense as she reached behind to zip it up, and all I wanted to do was zip it back down. I wanted to slide that dress down her hips and slide my cock into her slit.

  I exhaled. Time to go back inside and stroke again, I thought. My cock throbbed against my thigh and I hoped wheeling in the lawnmower would give me time to calm down.

  Before I made it a foot, the backdoor opened. Marla poked her head out. “Hey James?”

  “Yeah?”

  “Would you mind going over to Lily’s and letting her know I have her check for her.”

  My heart stopped and my throat tightened, forcing my voice into a higher pitch. “Me?”

  “Yeah. I’m working on dinner and you’re already out there.”

  I looked at the guest house painfully. “Sure thing.” Marla stepped back inside and I abandoned our lawnmower completely. My feet were heavy but determined as they marched across the lawn.

  I reached the door to her place and knocked lightly. Part of me was hoping she wouldn’t hear it at all, and part of me was hoping she’d answer naked. That’s silly, I thought. She at least would be wearing lingerie.

  Before I knew it my cock was hard again. I looked down and gasped. I could see the outline of my dick against my thigh. Just as I was about to turn around and run, the door opened.

  “Oh. James,” said Lily. Sweat dripped down my cheek as I watched her eyes shift toward my crotch. When she realized my dick was hard she looked quickly up at my face and strained to keep eye contact.

  “I just came to tell you Marla has your check.”

  “Okay, great. Thank you.”

  “Mmhmm,” I said, still standing there like a jackass. Neither of us made a move or a sound for the next few minutes. Instead, we shifted our eyes to the side awkwardly.

  “You look nice,” I finally said, cursing myself under my breath.

  “Thank you,” she said, lowering her head and looking out through the tops of her eyes. Her dark hair was straightened and draped down over her shoulders. “Would you like to come in for a moment?”

  “Sure,” I said. “I haven’t seen the place since you moved in.”

  She opened the door wider and I followed her inside. “It looks relatively the same,” she said, but I was hardly listening. My eyes were focused on her delicious ass and how her dress rose up slightly when she walked.

  She sat down on a small loveseat and patted next to her. I sat beside her while checking the windows for a direct view of the house. From our position, we were hidden and I breathed a sigh of relief.

  Lily turned to me with flushed cheeks. “I noticed you seem a little tense,” she said, her eyes watching me closely for a reaction. I remained silent, unsure of what she was getting at. “I could…help you with that…if you want.”

  “With what?” I asked.

  She lowered her hand to the top of my thigh and slowly dragged her palm upward until it was rubbing along my cock. “That,” she said, licking her lips.

  I exhaled and stared into her gorgeous eyes. Is our housemaid really stroking me right now? “Oh,” I said in a heavy breath. “That.”

  “Do you and Marla…”

  “We haven’t…in a while.”

  “You poor thing,” she said, her eyes growing hungrier.

  “Mmhmm,” I said. I could hear the blood pounding in my ears. She continued to stroke up and down lovingly. I leaned my head back and let my jaw fall open.

  Lily lowered her hand so that it was just under the hem of my shorts. I felt her fingertips slide under, crawling inch by inch up my inner thigh until she came in contact with my cock.

  I heard her gasp as the tips of her fingers touched my bare head. I looked down at her and saw that she was stari
ng at my lap. She moved her hand up more until her fingers were wrapping around my shaft and lightly stroking.

  “Ohh,” I groaned. I moved a hand to her head and tucked her perfect dark hair behind her ear. She turned her face toward me and her eyes were wide. Then she leaned up and pressed her lips to mine while stroking my cock.

  I parted my lips and slid my tongue into her honey sweet mouth. I groaned through our kiss as she stroked. I rested a hand on her hip and slowly slid it up to her ribs. Her breathing grew heavy and I could feel her ribcage expanding quickly.

  I moved my hand over to her breast and cupped it gently. Her tits felt mostly like padding from the bra, but that didn’t bother me. I was more of an ass-guy, and her tiny frame only made me want her more.

  Lily moaned and started to unbutton my shorts and boxers. I lifted my hips to help her slide them down. I shook them from my legs and felt her hand stroking me again.

  She pulled away from our kiss and knelt between my legs. She stroked my cock up and down while looking at it with an impressed expression. I wasn’t huge but I was larger than average. She seemed ravenous and it was as if my cock was the only thing that would satisfy her.

  She raised herself up slightly and opened her mouth. Her tongue was small and flat and she stuck it out just over her lower lip. It brushed against the underside of my shaft, sending a hot wave of euphoria through me. I combed my fingers through her hair to help keep it out of her face.

  Lily gently wrapped her pouty lips around the head of my cock. She looked like a repressed virgin. She looked at my cock like it was forbidden to her all of her life. She looked up through the tops of her eyes and I nearly came from the sight of her. She lowered down gently, easing my cock toward the back of her throat and I kept stroking her hair.

  “That’s it, baby,” I said, helping her ease into it. Once she had most of it in, I began rocking my hips to pump it in and out of her mouth.

  “Mmm, fuck yeah,” I moaned. Her nostrils flared as her breath quickened. I reached a hand into her dress under her bra and massaged her nearly flat chest. I didn’t mind that she was flat. It made her seem younger than she was. It made her seem like more of a virgin.