Man to Woman

by Jane Futa

  “What kind of maid are you?” she asked as she looked me over. “Is that a slutty costume?”

  “I can explain,” I said even though I didn’t have the slightest clue how.

  “Is that my dildo? Who the hell are you?”

  “My name is Bryan,” I said, resolving to tell her the whole truth. “I’ve followed you on social media for years. I’m your biggest fan.”

  “So you thought you’d break into my house wearing an obviously fake maid uniform?” My mouth hung open as I searched for the right words. “And did you say your name was Bryan? As in, you’re a boy?”

  I blushed and nodded. I hung my head down in shame as the reality of my situation became more clear and humiliating.

  “No way. Let me see,” she said, stepping toward me. I looked up her long, silky legs as she stood next to me. I could even see a glimpse of her white panties underneath the skirt of her dress. She reached down and grabbed my wrist, pulling me up toward her. She reached for the hem of my uniform and lifted it until she saw my panties. “I don’t see a bulge or anything.”

  “I’m kind of small,” I admitted, biting my lower lip. She reached for the waist of my panties and pulled them down until she saw my small dick poking out.

  “Oh. My. God.” she said and then burst into a fit of laughter. “You’ve got to be fucking kidding me!”

  “I’m so sorry. It was never my intention to break in-“ but the laughter kept coming. She brushed her fingers along my small cock as if she was checking to see if it was real. “Theresa, I-“

  “Hush,” she said, placing a finger to my lips. “You know that trespassers get punished, right?” I shook my head. Obviously, I wasn’t aware of the rules of her house. I imagined she meant arrested, but she had a strange gleam in her eye and the anger seemed to have fled.

  “If you want to be a sexy trespassing maid, you’re going to get punished like one. Now give me that dildo,” she said. My stomach was full of butterflies. I wasn’t sure where this was going, but the tone change in Theresa’s voice was exciting. My legs started to quiver similarly to when Wyatt had stared at my ass while I dusted his books.

  “Come on,” she said, grabbing the dildo in one hand and my fingers in another. She pulled me toward the bed and sat me down. “Wait here.”

  I watched her leave the room and lean over the staircase. “I need to have a meeting with all of the maids in the master bedroom!” she cried. I was terrified. What did she need them for?

  One by one, they started to pile into the room. There must’ve been 20 or 30 different maids all lining the bedroom walls. When the last of them entered, Theresa locked the door with all of us inside.

  “Ladies. What we have here is a trespasser.” They all gasped excitedly as if this wasn’t the first time they’d had this type of meeting. “Not only is she a trespasser. But she is actually a boy in girls’ clothing!”

  The maids started to smile and their eyes widened. Theresa turned to me and said, “Go on. Show them.”

  My blood pounded in my ears as I stood up slowly from the bed. I lifted my skirt and slid my panties to the side, showing the room full of maids my small cock. A few of them gasped, some of them chuckled, and one of them raised her hand to ask a question.

  “What’s the dildo for?” A few of the other girls laughed but had expressions as if they already knew. Theresa walked up to her and wrapped her arm around her shoulders.

  “Because,” she said, “trespassers get punished. Cross-dressing sissies get fucked.” The questioning maid gasped and prepared to watch. I saw Theresa walk toward me with a smile and the dildo in one hand.

  “Open your mouth,” she commanded a she approached the end of the bed. My palms started to sweat and my legs quivered. I parted my lips and stared at Theresa’s smooth, round breasts as she hunched over me, lowering the head of the dildo into my mouth. “You like my tits, do you?”

  I nodded as I wrapped my lips around the hard cock. “Do as I say and maybe you’ll get a little peek at them.” My heart beat faster. I couldn’t believe I was in Theresa’s house, much less giving oral to one of her toys with her gorgeous rack at the other end of it.

  She slid the cock deep into my mouth. It went deeper than Wyatt’s, but I was grateful that his gave me practice. “Wow. Impressive,” she said as she shoved the whole thing in. My throat expanded and a tear streamed down my cheek. I looked at the other maids for a second and saw every single pair of eyes on me. Some of them were smiling and laughing and others looked like they were turned on.

  Theresa pulled the cock out of my mouth slowly and said, “Good girl. You may feel my breasts for a second as your reward.” I reached out eagerly with one hand and rested it on her round tits. My cock grew rock hard instantly. As I massaged her breasts, Theresa moaned, and then she leaned in for a kiss. I kept squeezing her tits as she slipped her tongue into my mouth. For a moment, I forgot we were being watched at all.

  She pulled away and took a step back. She reached for the straps of her dress and slid them down her shoulders until the top half of her dress fell to her waist, exposing her large, bare tits. She was braless and her nipples were hard and pointing right at me. “You may suck them if you want,” she said, stepping closer to me.

  I leaned forward and parted my lips. I took her first nipple into my mouth and looked up at her. She stroked my hair and moaned as I sucked on her tits. I moved back and forth eagerly. I couldn’t get enough of her and I couldn’t believe this was really happening.

  “Ok, that’s enough,” she said, pulling her tits away. She didn’t pull her dress up yet. Instead, she told me to roll onto my stomach. I reluctantly did as I was told. I really just wanted to play with her breasts more.

  I rolled onto my stomach and faced some of the other maids. They watched the scene before them in awe. I felt Theresa’s hands slide up my silky legs and lift my dress up above my hips. She pulled my panties down my legs until they dropped to the floor. Then she dragged the dildo up and down each of my legs and some of the girls laughed.

  Theresa crawled beside me on the bed so that I had a peripheral view of her bare tits. She spread my ass cheeks and spit between them. Then she rubbed the spit into my asshole, fingering it a few times.

  “Ohhh,” I moaned as I was reminded of Wyatt’s huge cock fucking me the night before.

  “You like that, hm?” she asked. I nodded. “Beg for it,” she said.

  Beg for it? I was too timid! I was too shy! But I wanted it. Oh, how I wanted it! “Please,” I said meekly, hoping it would be enough.

  “Louder,” she said.

  “Please!” I cried.

  “Please, what?” she asked, straightening up in defiance. As she sat up, her breast shifted slightly and my cock felt like it was going to explode.

  “Use the dildo, please,” I said.

  “You mean fuck your little asshole?” I nodded. “Say it,” she said.

  “Please, fuck my little asshole,” I begged. She stroked my hair.

  “That’s a good little slut,” she said. She spit on my ass again and rubbed it in with her fingers. Then she pressed the tip of the dildo to my hole and pushed in.

  “Oh!” I cried as my asshole stretched again. My eyes met with the eyes of the other maids as they watched my idol fuck me like a little slut. I shifted my gaze back to Theresa’s tits which were swaying as she pushed the cock in and out of me.

  “Yeah, this is what you wanted, right?”

  “Mmhmm,” I said with my fist pressed against my mouth.

  “This is what you get for trespassing and being a little sissy.”

  “Oh!” I cried again. She slid the cock in and out faster until I was about to cum. Then she pulled it out and lay it on the side of the bed.

  “Roll over,” she told me. I rolled over and watched her climb above my face. She reached under her dress and slid her panties to the side, exposing her soaking wet pussy to me. “I’m going to ride your little sissy face until I cum,” she told me.


  Oh fuck, I thought. I’m going to get to lick Theresa’s pussy. As she lowered her hips over me, shrouding me in the bell of her skirt, I couldn’t help but feel gratitude for the strange chain of events which led me here. I stuck out my tongue and tasted that that pleasant juice that had covered the dildo before. She rode my face as all of the other maids watched, and I knew they could all see my exposed cock growing harder and harder.

  I slid my tongue into Theresa’s pussy and circled her clit, but for the most part she was in control. She rocked her hips back and forth over me while she moaned. Then she reached the bottom of her dress up so I could see her tits bounce each time she thrust forward.

  I moaned into her pussy and felt it contract around my tongue. She grabbed her breasts and pinched her own nipples.

  “Sarah!” she called, and a maid rushed over. Sarah climbed on the bed and took one of Theresa’s nipples into her mouth. “Oh! Maria!” she called. Maria, from the kitchen, rushed to other side of her and took the other nipple into her mouth.

  I stared up at Theresa, with a maid sucking on each nipple, as she rode my face to orgasm. She leaned back, opened her mouth wide, and let out a wild scream as she came all over my face. My cock swelled at the sight until I came too, spilling cum all over my shaft and torso.

  I heard giggling in the distance and some moaning. Sarah and Maria were touching their pussies as they helped Theresa come down from her orgasm. Then Theresa ordered them away and they thanked her for the opportunity.

  I couldn’t believe what had just happened. Theresa swinger her leg over my head and climbed off the bed. She readjusted her clothes until she was full dressed again, and then she ordered all of the maids to leave.

  “Not you, Bryan,” she told me as I started to head for the door. When all the maids left, I turned back toward Theresa.

  “Theresa, I am so, so sorry,” I told her, feeling a little more confident strangely enough.

  “What do I have to do to keep you on my staff?” she asked me as she sat on the end of the bed. I walked toward her with a look of surprise.

  “What do I have to do to stay?” I asked.

  “Oh, just more of that at my command,” she teased, flipping her hair back. “Sit,” she said, patting the spot next to her on the bed. I sat beside her and looked up at her. “What do you need, Bryan? And do you have another name you like to go by?”

  My stomach had butterflies again as I tried to work up the courage to tell her my needs. “I go by Melody,” I said. “And if it wouldn’t be too much…” but I didn’t have the balls to finish.

  Theresa reached her hand under my chin and pulled my face to hers. She kissed my lips and then said, “Anything. Just tell me.”

  “Well…I kind of need a place to stay.” She started to laugh. “I’m sorry,” I said. “I knew it was ridiculous.”

  “Is that all?” she said. I was confused but hopeful. “You got it.”

  “Wait…really?”

  “Of course! You are special, Melody. You’re unlike any of my other house workers. I have to keep you around.”

  I felt elated. I couldn’t believe my luck. Just moments ago, Melody had caught me holding her dildo locked in her bathroom, and now she wanted me to stay?

  “Come on, I’ll show you to your room.” She stood up from the bed and took my hand. I followed her down the hall to the bedroom that was next door to hers. It was much smaller, but full of gorgeous mid-century furniture. The walls were lined with vintage posters and she even had a few plants on the side tables.

  “Welcome home, Melody,” she said. I turned around and wrapped my arms around her tightly.

  “Thank you! You won’t regret it!” I cried.

  “See that I don’t,” she said playfully. “I have very creative ways of collecting payment.” We both laughed and then she kissed me again. “I’ll let you get settled, but be prepared to work again tomorrow.” I nodded and watched her curves sway as she left.

  I threw myself on my new bed and smiled. Everything is finally perfect, I thought.

  Mile High Club

  Chapter 1

  “You ready, Jacob?” asked Bryce when I opened my front door. I grabbed my bag and flung it over my shoulder. I always like to pack light on a trip so I know I won’t lose my luggage to the airline. I followed him to his car and saw Sam and Rob sitting in the backseat.

  The rolled down the window and shouted, “Let’s party man!” I laughed and threw my bag in the trunk of Bryce’s car. Then I climbed in the passenger seat and gave a friendly “bro” handshake to everyone. Then we turned up the radio and peeled out of the apartment parking lot.

  My buddies and I were headed to Cancun to celebrate making it through another year of college. We’d worked our asses off and saved up all year for it. There were lots of reasons to go to Cancun, but our agenda? We wanted to get laid a lot. We’d heard countless stories of crazy sexual encounters and we just wanted to have a good time.

  One of our buddies had gone last year and his stories were endless. Random chicks every day, sharing them with his buddies. It was just one giant party where you could forget all the stresses in life. You wouldn’t feel anything but pure ecstasy.

  None of us had been to Cancun, but we were all excited. We didn’t have much of a plan, so we were ready for anything.

  We decided to make it interesting. The first guy to nail a chick gets his flight paid for by the other three. Of course proof was required. It didn’t have to be big. A pair of wet panties would be good enough, but nothing that could be store bought. We were all pretty attractive dudes, so we knew getting laid wouldn’t be too difficult.

  We jammed to music all the way to the airport. The weather was nice, but we knew Cancun’s would be better. When we finally arrived, we parked the car and grabbed our luggage. As we neared the airport doors, my eye caught sight of the hottest woman I’d ever seen. She looked like a flight attendant, and her breasts looked as if they were trying to burst out of her uniform.

  My cock hardened instantly and I tried to keep it under control. I hadn’t been this easily turned on since high school. She was waiting at the door and as we walked past she looked up at me. When our eyes met, she smiled and winked at me. I couldn’t stop, but it nearly killed me to keep walking. There was something magical about her. There was something that made all my other conquests seem trite and trivial.

  “Come on, dude,” urged Bryce. I reluctantly snapped my gaze away and we entered the bag check line. We were early, but only because we wanted to get a drink or two before we boarded the plane. The lines were long, but otherwise getting through security was pretty smooth. Of course, we were all pretty white with the exception of Sam who had hardly enough Mexican in him to worth mentioning.

  He liked to brag, though. He said it was why he tanned so easily. As if Bryce and I couldn’t get a tan on our own! Poor Rob, though. He burned easily without sunscreen.

  We crossed through moving walkways and escalators until we’d neared our gate. Then we found a sports bar and each pulled up a seat. We ordered are drinks and basked in our trip’s success so far. As the guys picked up their conversation, my mind started slipping back to the gorgeous flight attendant. I quickly excused myself and headed for the nearest bathroom.

  I found one down the hall and turned the corner. I found it surprisingly empty and slid myself into the stall farthest from the exit. Then I dropped my pants and watched my hard cock spring out of its cage.

  Chapter 2

  I wrapped my fingers around its shaft and began to tug. I leaned one hand against the wall for support, aiming the head of my cock over the toilet. I closed my eyes and thought of unbuttoning the flight attendant’s blouse slowly. I imagined each new inch of skin exposed until I had her in just a sheer bra. I ran my hand over her large, full breasts and kissed her pouty red lips.

  I tugged faster and imagined her tongue against mine and her breasts pushing up against me. I ran my hands down her back and over her round ass. Her eyes were closed
but her mouth hung open as she gasped from my touch. I unhooked her bra and took her nipples into my mouth. Her body quivered as I built her up. I was preparing her for my cock and she was almost ready.

  I sucked and bit her nipples as I unzipped her skirt. It dropped to the floor revealing sheer white panties that were soaking wet. I slid my hand along her pussy and watched her knees buckle. Then I slid the sheer, wet fabric to the side, lifted her up in my arms, and slid my hard cock into her tight, virgin pussy.

  I stroked my cock harder at the thought of entering her. She was pressed against a wall and I slid in and out of her wet cunt. She had her fingers in my hair and her arms leaned against my shoulders for support. Her tits bounced with each thrust of my dick, and I moved my mouth between them eagerly.

  Within minutes I was cumming and panting, trying to quiet myself in case anyone had entered. I caught my breath and zipped my pants back up. I noticed some of my cum on the seat below and I wiped it clean before flushing. Then I ran a hand through my hair coolly and adjusted my clothes. I left the stall and washed my hands. As I looked in the mirror above the faucet, I saw my reddened cheeks and smiled.

  Maybe that’ll be enough for now, I thought. I dried my hands and walked back out into the main hallway. I was so distracted by my orgasm that I bumped into a girl, nearly knocking her to the floor. I reached out to grab her arm and caught her just in time.

  “Shit, my bad,” I said. Then she looked up at me, her straight brown hair shifting from her shoulder to her back. I recognized her as the flight attendant from the door and my recent fantasy. My voice felt locked in my throat suddenly. She picked herself up, her breasts brushing against my arm as she collected herself.

  “It’s ok,” she said in the sweetest voice I’d ever heard. “It happens all the time. People rushing around to get to their flight and all.” I nodded like an idiot. She found my silence amusing and smiled. Then she walked away, leaving me as quickly as she’d arrived. I wanted to run after her, but what would I say? Would I tell her I wanted to fuck her brains out? Something about her told me she might even be down for that, but she had me tongue tied. So instead, I just watched her round ass walk away.