Man to Woman

by Jane Futa

She rubbed the silky fabric on my ass cheeks and I cooed in reply. Then she gave it another whack before saying, “Good boy,” again. “Now flip over. On your back.” I did as I was told and lay down for her. She crawled above me and I realized she had removed her panties while I was getting changed.

  I groaned as I saw her place her soaking wet pussy above my face, her legs on either side of my head. “Now I’m going to let you taste me,” she said, lowering her hips to my face. I eagerly stuck out my tongue and she rode my face to the brink of orgasm. Then she pulled herself off, trying to catch her breath as she held her orgasm in.

  “Next outfit,” she commanded. My dick felt like it could explode at any second. Cecilia wasn’t the only one holding back her orgasm. I quickly moved behind the screen again and took off the bra and panties slowly. I reveled in the feeling of the fabric sliding against my skin. When my cock was free, I was half tempted to jerk it so I didn’t come too soon, but I knew that Cecilia would notice later and be displeased with it. So I moved onto the next outfit.

  I stepped out of the stilettos and draped the bra and panties over the screen as a little teaser to Cecilia. I heard her sigh when she saw the red fabric. Then I reached for the black negligee and slipped it over my head. Then I realized there was a black cotton thong that also belonged to it. I watched it drop to the floor and then I slid it up around my waist.

  The cotton felt similar to my briefs, but the thong portion was what made me feel pretty. I loved having the see through fabric draped across my torso. Having thin straps on my shoulders made me feel delicate, like a flower. I can’t believe how much I’m enjoying this, I thought. It’s so twisted and wrong, but I’ve never been more turned on in my life.

  I stepped out from behind the screen and paraded my new outfit.

  “What a good boy you are, Kevin,” she said. “But for tonight, your name will be Karen.”

  “Yes, ma’am,” I said.

  She curved her index finger and wiggled it for me to come to her. “Strut for me. Shake your hips,” she said. I placed one feminine leg in front of the other and tried my best to sway my hips like a woman as I walked toward her.

  “Good boy,” she said when I had reached the end of the bed. She reached her hand out and gently rested it on my hard cock. “I love knowing there’s a dick under all that feminine fabric,” she told me. “I bet you love dressing like a slut,” she said, looking up at me with big doe eyes.

  “Yes, ma’am,” I replied. She smiled and then gently grabbed my balls. I couldn’t help but groan but I tried to keep from coming.

  “I bet all this lace makes you want to come like a good girl, doesn’t it?”

  “Yes ma’am,” I said.

  “Well, don’t you dare come yet,” she warned. I pulled back as much as I could to keep from coming, but she kept stroking and groping me. “Ok,” she said, exhaling. “Last outfit.”

  I turned away, swaying my hips as I returned to the screen. My senses were more alive than they’d been in years. For the first time in my life, I wasn’t thinking about becoming famous or furthering my career. I was completely euphoric in the moment, as a woman. I couldn’t believe how different I felt wearing a little lingerie, but I felt alive. I felt new.

  The slight humiliation I felt from parading around in women’s clothes to a potential producer was overshadowed by the pure ecstasy I felt. It was the strangest set of emotions, and I preferred it that way. The entire night had been one giant surprise to me.

  As I stripped my masculine body of the second feminine outfit, my mind wandered to the future. Is this something I would continue to want for myself? Now that I’d been open to the world of cross dressing, I couldn’t imagine giving it up for ordinary experiences. Maybe I would secretly wear women’s panties on set, I thought with a sly smile to myself.

  I reached for the last outfit. It was the most intimidating. I started with what I knew, sliding on the bra and panties. The white complimented my tan skin nicely. As frightened as I was of the garter belt, I was also excited. It was the hottest piece of lingerie of all three sets, and I couldn’t wait to find out how beautiful I’d feel in it.

  I slid the belt up my legs and over my hips, letting the claps hang. Then I slowly rolled the first stocking over my foot, up my ankle, and pulled it up to my thigh. I thought I might come right there from the taboo alone. A man in women’s stockings? But I had never felt so sensual and perfect before. I slid the other stocking up and dared to take the task of figuring out the clasps.

  I fumbled with them for a few minutes, and I heard Cecilia moaning from the other side of the room. “Are you almost ready, my princess?” she asked.

  “Almost,” I said, raising the pitch of my voice. I finally figured out how the clasp grasped the stocking fabric and fastened the other three. Before I walked out for Cecilia, I stretched my legs and let the fabric pull and gather at my skin. My cock was harder than it’d been all night. I was Cecilia’s little princess.

  I stepped out from behind the screen and saw Cecilia lower her hand from her neck to her collarbone. “Stunning,” she said with a gasp.

  She spun her finger around in a circle and said, “Give me a twirl.” Like a little girl, I turned around, showcasing the entire outfit. “I bet you love wearing those stockings,” she said.

  “Yes, I do,” I admitted with a slight blush to my cheeks.

  “Good. Now press yourself against the wall.”

  I wasn’t sure what Cecilia was about to do to me since this was the last outfit, but I didn’t dare disobey. I stood next to the wall, pushing my hands and chest into it and poking my butt out like a woman would who was about to be dominated.

  “Good girl,” she said, walking toward me with a feather in her hand. She kneeled behind me and tickled the feather against my calves, then my thighs, and finally slid it between my legs. I felt a light tickle against my balls through the lace fabric and moaned.

  “You like that, do you? You’re such a naughty princess,” she said. Then she dropped the feather and let her hands caress up and down my legs, moving faster the more turned on she got. I could tell she wanted to stay in control but was too ready to come to wait too long.

  Soon, I felt her hands fumbling with my panties. I exhaled as she reached under the garter belt and looped her fingers around the waistband of my panties. She pulled them down over my ass and let the fabric stretch around my thighs. They were pulled down as far as possible without having to unhook the garter belt clasps.

  She teased my asshole with her finger. “My princess has a nice little ass,” she whispered, now leaning over my shoulder with her lips pressed to my ear. Her breath traveled down my neck and sent a chill through my body. She circled her finger around my hole and then slid it up and down my crack.

  She bent down and pulled my panties back up. I heard her fasten something to her body, but I waited for her instructions to look. “Get on your knees and face me,” she said.

  I turned around and saw that she was wearing a black strap on dildo. It was huge and hung from her waist. She had removed her clothes so aside from her breasts, she looked like a man ready to fuck his princess.

  I lowered myself to my knees and she walked toward me. The dildo swayed as she walked and I nervously anticipated what was next. “Open your mouth,” she commanded.

  I lowered my jaw so that my mouth hung open in a large O shape, waiting for her to enter. She rested the black cock on my face, dragging it around from one cheek to the other. She traced it along my jawline and moved it from ear to ear. I moaned as I felt the head of the cock slide across my skin. I’d never been so submissive before, but I enjoyed every second of it.

  She rested the tip of the head against my lower lip. Then she reached her hand down and stroked my hair. “What a good little princess. You going to suck this cock for me?” she asked.

  I nodded and she quickly slipped the head into my mouth. I tightened my lips around the shaft, my body tensing from the eroticism it provided. I couldn’t bel
ieve how much I was enjoying having a dick in my mouth while I was dressed like a woman. I felt sexier than I ever had in my life.

  I moved my head back and forth, swirling my tongue along the shaft. I loved the feeling of the cock ridges against my tongue. I imagined it coming in my mouth, semen spilling toward the back of my throat.

  Cecilia gripped the short strands of my hair in her fingers. She held my head in place and began to fuck my face with her cock. I gagged a little as she thrust toward the back of my throat. Having her fuck my face made me feel complete; like that dick belonged in me. Suddenly, I found myself wanting to feel it inside another hole.

  I thought of how it felt when Cecilia’s fingers teased my ass as I sucked her cock. I imagined her fucking my ass with her dildo and I started to moan through the blow job.

  “What a good little princess,” she said moaning as she thrust her hips toward my face. I groaned in response and she smiled. She looked down at me with round, commanding eyes. I knew this wasn’t the only idea up her sleeve.

  “Now that it’s nice and wet, I want you to bend over on your hands and knees.” I pulled off her cock slowly and wiped my mouth. I turned around and bent down so that my hands lay flat on the floor. “Good girl,” she said, giving my ass a little spank.

  She reached over and pulled my panties down again, exposing my asshole. Then I heard her open and close a bottle of lube. I heard her lather the slick gel over her dildo, moaning as if the cock was really hers. I can’t believe I’m about to get anally fucked by the movie producer, I thought to myself. I bit my lower lip as I waited. I’d never had so much as a finger in my ass before and yet I was never more excited to feel anything as I was now.

  Cecilia 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 first inch of her finger entered my ass.

  “You like that, baby?” she asked me.

  “Yes,” I admitted.

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

  I moaned with her as she fingered my ass and my body twitched with eager anticipation. She pulled out her fingers and reached around to my face. “Clean them with your mouth,” she said.

  I opened my mouth and wrapped my lips around her fingers. I could taste my asshole on her skin and I was ready to come. I held back as much as I could, waiting for her to tell me it was okay to.

  She slid her fingers in and out of my mouth a few times before dragging their wet tips along my cheek. Then I felt her hands on my ass, massaging and spanking it intermittently. With each slap I moaned helplessly. She spread my cheeks apart and then rested the length of her cock between them.

  “You ready for the best fuck of your life?” she asked me. I nodded and closed my eyes. She dragged the cock down so that the tip rested at my asshole. I felt my ass stretch as wide as possible when she slowly pushed in the head.

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

  “There, there,” she said, rubbing my back. She continued to push and I felt my ass pulse and stretch around the permanently hard cock. My body tensed at first and then finally started to relax into it. The deeper in she got, the better it felt.

  I groaned and she moaned. Her cock was pushed all the way in and I felt her quaking body pressed against me. “You like getting your tight little asshole fucked?” she asked.

  “Yes, very much,” I replied.

  “Good girl,” she said and slowly pulled the cock out. I felt my asshole 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 body shaking as I neared orgasm, but I hadn’t yet been given permission.

  “Does all this fucking make you want to come?” she asked.

  “Yes, please.”

  “Beg for it,” she said as she started pumping my ass faster. Soon her pelvis was slamming into my ass as she shoved the cock deep inside me.

  “Please let me come for you,” I begged.

  “Louder,” she commanded.

  “Please let me come!” I squealed as she thrust into me over and over. Cecilia moaned as she rocked her hips and it felt so good to play the woman.

  “Ok, princess. Come for me,” she said in a low growl. She pounded my tight little ass faster and harder and I pretended to be a woman getting fucked for the first time.

  “Fuck!” I cried as I shot my load all over myself and the carpet. She pumped my ass over and over while my thick ropes shot out. She grabbed my ass and I felt her body shake. She was coming too.

  “Shit!” she cried, hunched over me like a man ejaculating. She had the cock shoved deep inside me as we both finished together.

  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.

  Cecilia collapsed next to me and we both exhaled deeply. “Fuck,” I said, still in awe of how the night had turned out. “Does this mean I have the role?” I asked, half kidding and half serious.

  She turned her head to face me. Her eyes looked at me seductively and she bit her bottom lip. “Did you enjoy yourself tonight?”

  “I came didn’t I?”

  She laughed, “Yes you did.” She propped herself up on her elbow and looked at me with a serious expression. “I’ll tell you what. You can have the role if I can get a few more nights of this with you.”

  “I couldn’t think of a more perfect scenario,” I told her, smiling. I had meant every word. I had no idea at the beginning of the night that I would end up wearing lingerie and getting my ass fucked, but at the same time I wasn’t disappointed. In fact, Cecilia was responsible for opening me up sexually to something new, and soon I would learn it was something I needed to feel whole.

  “So how many people have you done this with?” I dared to ask her.

  “Only a few,” she said. “You’d be surprised at how many guys are uncomfortable cross dressing even for a film role.”

  I was genuinely surprised. I figured everyone was like me, willing to do anything to get in.

  “Of the guys I’ve turned into girls, though, you are my favorite little princess,” she said with a wink. She reached across the floor to me and ran her hand through my hair delicately. She dragged her fingers down my cheek and rested her thumb on my lower lip.

  I wrapped my lips around the tip of her thumb and gave it a familiar suck. I was completely spent. “I bet you’re eager to get out of those binding clothes, hm?” she asked.

  “Actually, no,” I admitted. “They make me feel sexy and beautiful.”

  “You are,” she said. “You’re definitely my favorite little toy.”

  My body tensed when she called me her toy. The image got me hard again.

  “Looks like someone wants a round two,” she said as she ran her hand up and down my thigh. “What do good little princesses say?”

  I looked up at her with big baleful eyes. “Please,” I said.

  She smiled and then leaned in to kiss me. She forced her tongue into my mouth and swirled it around. Then she pulled away and said, “Good girl.”

  I was definitely looking forward to working with Cecilia.

  Dressed for a Ride

  I guess just because you can do something, doesn’t exactly mean that you should do it.

  I probably should have been telling myself this, as the arid desert breeze brushed against my eyes and I banged my lithe fist against the hood of my deadbeat car in frustration. The hot metal hood – cherry red – only burned my fist, and my car had the last laugh, as usual.

  “Fuck,” I exhaled.


  I looked one way, and then the opposite, down the lonely two-lane highway; not another sign of life for miles, and the late-afternoon temperature inched toward triple-digits, so much so that the waves on the cracked asphalt horizon waded like transparent globs from a lava lamp.

  I knew I ran the risk of this very situation when my uncle offered me a job in Phoenix. College had done little for my job prospects and now, unable to find any internship, I found myself driving from the cooler summer of Tennessee, to the unforgiving wasteland of the Southwest. That’s not to say that I didn’t find the empty landscapes gorgeous – because I did – but it helps to not have a piece of shit car to travel by.

  And mine was a certified piece of shit.

  I had no idea what had happened this time – all I knew was that the smoke coming from under the hood was probably not a good sign. I decided to pull off the highway on my own, before the car exploded and I found myself blown past the dull brown mountains and tall cacti in the distance, like some sort of cartoon.

  I brushed my jeans and fanned my white t-shirt as sweat started to drizzle against my cheekbones and I felt the sting in my blue eyes, squinting and looking out for just about anything. Hell, if a donkey had shown up, I would have asked for a ride. But there was nothing, and my cellphone’s shitty reception was no use, either.

  I kicked the tire of my car and walked toward the trunk. I’m not even sure why I did it – I think for a moment, I thought there could be something useful in it. I didn’t know the first thing about cars, but I suddenly imagined with some hopeless optimism; maybe if there was water in the trunk, I could find a hole in the engine to pour it in. I’d cool it down and be right on my way. As I said, I know nothing about cars.

  When I popped open the trunk, I brushed my hand over my short dark hair and laughed. I shook my head as I saw, not water, but something I had completely forgotten about. Six months before, one of my buddies in college had decided to go to a Halloween party in total drag. I never asked him why he’d decided to do that – all I knew was that he seemed to love every moment of the car ride over to the party, dressed in the long golden wig, the over-the-top makeup and the trendy little blue spaghetti strap and tight denim jeans. The moment I saw the stuff lying there in my trunk, the entire evening came back to me. It had been a blur since it even happened. Even though I was the designated driver on the way to the party, I slipped up and had way too much to drink. I ended up passing out at the house and driving home the next morning with a head-splitting hangover. My buddies presumably found another ride home. And little did I know, I had been driving around for six months, with the girl’s outfit in my trunk.