Man to Woman

by Jane Futa

  But I wasn’t a full woman, and I was curious. “Okay,” I said. I looked around the room for Ben, but he still hadn’t returned. Why the hell did I ask for a girly drink? They always take the longest to make. I figured maybe he got caught up talking to someone in the kitchen.

  I stood up from the sofa and followed Josh upstairs. We didn’t even make it to a bedroom before he had me pushed up against a wall with his tongue down my throat.

  He tasted sour and was more forceful than I had expected. His hands were on my padded bra and then traveled down to my hips. Fuck. He’s going to feel that I have a cock. And he did. His hand brushed right over my hard dick, but he was too drunk to realize what it was. I waited for him to put it together, but his hands eventually just made it to my ass. He squeezed it and pulled me into him.

  “You’re already panting,” he said. He was right, but he didn’t know why. I was breathing quickly from the fear of getting caught. After all, his hand had just brushed down the shaft of my cock. My body was filled with panic and ecstasy. This was the most exciting night of my life and I knew it would stay that way if no one found out who I really was.

  Suddenly, Ben came running up the stairs. “Hey, asshole!” he shouted toward Josh. “She was hanging out with me first.”

  Josh pulled from our kiss and confronted Ben. “Hey, man! You snooze, you lose!”

  Ben raised his fist up, preparing to slam it into Josh’s face. I covered my mouth with my hands in horror. Then his eyes met mine and he lowered his hand. “I’m sorry, man,” he said.

  “You’re fucking crazy!” shouted Josh. “You can have the fucking whore.” Josh quickly left the scene and ran down the stairs. I kept my back pressed to the wall as Ben approached me.

  “I’m sorry, Lexi. I didn’t mean to frighten you. I don’t know what came over me.” I was silent. I didn’t know what the fuck had come over him either. “I guess I just saw him on you and it sent me into a rage.”

  My heart started pounding. I had no idea Ben was such an alpha type. I felt my entire body fill with arousal. Without thinking, I wrapped my arms around his neck and pulled him into me for a kiss. He leaned his hands on the wall behind me and slid his tongue into my mouth.

  Ben tasted as sweet as Josh tasted sour. I couldn’t get enough of Ben’s lips and tongue on me. I moaned into his mouth, practically begging for him to place his hands on me. I knew I was taking a huge risk. If I tried to do anything with him, he’d definitely find out I wasn’t who I said I was.

  But I couldn’t help myself. I wanted him to touch me. I wanted him to fuck me. Somewhere, deep down, I wanted him to love me. Not as Mike, but as Lexi. I suddenly wished I really was a girl.

  Chapter 8

  Ben pushed me harder against the wall. His hands ran from my ribs to my hips and across my thighs. Then he pulled back quickly, too my hand, and said, “Come on. Not in the hallway.” I followed him without question. As we entered a nearby bedroom, I heard the sound of male voices disappear.

  It was just me and Ben in a dark room. I could just make out the outline of his broad shoulders. They were highlighted by the street lamp that poured into the window. He pressed his mouth to mine again and slid his tongue in. His hands grabbed my ass and he pulled me up against him. I felt my hard cock rub against his thigh and hoped he hadn’t noticed.

  “You look so fucking hot, tonight,” he whispered, leaving a trail of kisses down my neck. I grabbed his biceps and squeezed, surprised at how much his body was turning me on. I wanted to be taken like a woman is taken by a big, hunky, alpha male. I wanted Ben to treat me like a dirty slut.

  “Thank you,” I replied, biting my lower lip as he tugged my shirt off my shoulder.

  “I never knew you were into this sort of thing,” he said in between kisses. I furrowed my brow into confusion and then I felt his hand on my cock.

  No way. There’s no way he fucking knows. “What do you mean?” I asked innocently. He pulled away and stared into my eyes. He brought his hand to my cheek and touched me romantically.

  “Come on. I knew it when you walked in. Mike.” My jaw fell to the floor and my eyes widened to the size of golf balls.

  “I don’t- I don’t know what-“

  Ben put his finger to my lips. “If you don’t want me, just say so. But just know this. I want you like I’ve never wanted anyone before.” He pulled his finger away and looked at me again, waiting for an answer.

  “I want you,” I told him, finally. Part of me was relieved that he already knew what he was getting into and part of me was terrified. Knowing that I was caught, however, was a huge turn on. I was just ready to come.

  Ben kissed me again and then lifted my shirt above my head. He ran his hands over my padded bra and squeezed. I felt the fabric rub against my nipple and I moaned. I lifted his shirt and let my knuckles trail against his pecs. I couldn’t believe how attracted I was to him.

  I unfastened his pants and slid them down. I let my body drop to the floor with them, until I was face to dick with his huge cock. I’d never thought I was small, but he made me feel so tiny. His cock was thick and long, and I couldn’t believe I was about to take it into my mouth.

  He looked down at me and stroked my fiery red hair. I wrapped my fingers around his shaft and parted my lips. I’d never sucked a cock before, but every fiber of my being wanted to suck his like a little slut. I stretched out my tongue and lowered my jaw. Then I rested the head of his dick against the back of my tongue and slowly tightened my lips around him.

  “Ohhh,” he moaned when my mouth enclosed his head. I slid it in further toward the back of my throat and heard him moan again. I could feel every ridge and curve of his cock massaging the roof of my mouth. When his head reached the back of my throat I felt my cock harden more than it ever has before.

  I let out a muffled moan with his dick still in my mouth. He rested his palm on the back of my head and kept me pushed down on his cock. When he released me, I came up quickly for air and he smiled. Then he shoved my head back down.

  He started pumping in and out of me, taking me like the little whore I’d become. Each time his head touched my throat, I wanted to come. I took him in over and over again, still trying to process how this had all happened.

  I reached for his ass and squeezed it while he fucked my mouth. He leaned his head back to let out a loud growl and then he fucked me faster. Just before he was about to come, he pulled out and lifted me from the floor.

  “Get on the bed,” he ordered. I moved to the bed and sat down. “On your stomach,” he said. I turned over so that my face was buried in the sheets and then I waited for him to take me.

  I felt his hands run up my smooth thighs. I moaned as he touched me like I was a woman. Feel his rough skin on my silky legs was thrilling. I felt chills climb up my spine and spread into my head. I loved laying there in the dark, being felt up by some college guy. For a second, I pretended I didn’t know him and that he was taking advantage of me. It was all an elaborate fantasy.

  But Ben was good and that’s why I liked him. That didn’t keep me from pretending he was bad and I was helpless. I felt him lift my skirt until my panties were showing. He rubbed his hand over my ass cheeks and then spanked one.

  I jolted forward on the bed suddenly and let out a cry of surprise. I heard him chuckle and then he spanked me again. “That’s what you get for trying to fool everyone,” he told me.

  “Am I in trouble?” I asked teasingly.

  “You bet your sweet ass, you are.” He spanked me again and I shot forward. I gripped the sheets in my fingers. In one quick motion, he tore my panties down to my ankles. He didn’t bother trying to pull them down over my long heels.

  He kissed each of my legs until his mouth reached my ass. Then he spread my cheeks and licked around my asshole. I couldn’t believe how good it felt to have his tongue there. My cock hardened and I wasn’t sure how much longer I could keep from coming.

  He stuck his tongue inside me and I squirmed on the bed. Each
time I moved, though, he spanked me to remind me who was boss. He slid his tongue in and out of my ass and licked along the edge. Then his tongue traveled down toward my balls.

  I felt him swirl the tip of it massage around my balls. I moaned to let him know I was close to coming and he spanked me again. “Not until I say,” he warned. His authority reminded me of Lexi’s and it only turned me on more.

  He pulled his mouth off of me and spit on his cock. I heard him jerk it a few times before resting the head between my cheeks. He pushed in slowly and I gasped as I stretched around him.

  “Fuck,” he groaned as he slid into my tight, virgin ass. I wasn’t sure I could take him all in because of his size, but he worked his cock in there until his balls were touching mine.

  “Oh!” I cried out as he pushed in deep. Then he reached for my throat and cupped his hand around it.

  “That’s a good little girl,” he said as he started to pump in and out of me. “Tell me how bad you want it.”

  It was difficult to respond. Between the pain and pleasure, my head was spinning. “I want it so bad,” I finally uttered.

  “What is it that you want?” he asked.

  “To come.”

  “That’s a good girl,” he said again. His voice was rough and sweet at the same time. I wanted to please him as much as I wanted to be dominated by him. He put both of his hands on my hips and started to thrust in and out of me.

  Then, to my surprise, he pulled out. “Flip over,” he demanded. I rolled onto my back with a confused look on my face. “I want to see your eyes as you come.” I exhaled at his words and watched as he lifted my legs up to expose my asshole. He leaned between my legs and took my balls into his mouth. He sucked on them and juggled them against his tongue. Then he licked along the shaft of my cock.

  I moaned and felt myself throb against his mouth. His hot breath traveled down my groin until it reached my ass. “Please,” I begged. “Please, fuck me.”

  His lips curled into a smile and then he stood up until his cock rested against my hole again. He pushed in until he was balls deep. He leaned over me, his face inches from mine, and stared into my eyes. Then he started pounding me with all of his strength.

  I reached for his shoulders for support and looked down. I could see his long, thick cock disappear inside me. He thrust over and over until veins started protruding from his neck. Despite all the force he was using, there was tenderness in his eyes.

  Moments later I screamed and started to come. I watched my come spill all over my skirt and navel. I watched Ben’s muscles tense until he let out a low growl.

  “Fuck!” he cried. I felt his hot come spill inside me. I had never felt more whole and complete in my life. He kept pumping over and over until his come was spilling back out of my ass and onto the bed. Then he collapsed on top of me while he caught his breath.

  As we lay there, I wondered what would be next. I feared he would regret what we had done, but I knew I never would. I waited for him to say something or to yell at me for tempting him. Instead, he lifted his head and gave me a kiss.

  “That was incredible,” he said with a smile on his face. His cock had softened inside me. He pulled it out slowly and lay next to me on the bed. He stretched out his arm so that I could snuggle inside of it. I lay my head on his chest and smiled as his come dripped from my asshole.

  “Yes, it was,” I said, running my fingers along his chest. “Does that mean everyone downstairs knows that I’m a little sissy?”

  He laughed. “Hardly. They’re all pretty wasted and stupid.” As soon as my hopes were lifted, they were dashed by the thought of having to put my sissy costume away after the night was over.

  “That’s too bad,” I replied. “I’d kind of like to try this full time.” I said this partly as an admission to my new love of cross-dressing and partly as an admission to wanting to be Ben’s little sissy.

  “You could, you know.” He turned his face to look at me and then he kissed my forehead.

  “Do you like me this way?”

  “Did you not just feel my cock inside you?” he said with a laugh.

  “I didn’t ask about your cock,” I replied, leaning up on my elbow and looking down at him. “What do you think?”

  He leaned up to face me and brushed my cheek with his thumb. “I think you should do whatever the hell you want and know that you have my full support.”

  I bit my lip and tried to process the past twenty four hours. “I’m not ready to tell anyone yet,” I told him.

  Ben took my hand and said, “That’s ok. I’ll be there if you ever do.”

  I smiled and kissed him hard. “Does that mean?”

  “If you want,” he said.

  “We’re dating?”

  He smiled and nodded. “If you’ll have me,” he joked.

  My heart swelled with pride. Ben was the nicest guy in the group. He’d always been single but I never understood why. Either he was gay or just waiting for the right woman. I secretly hoped it was the latter and that I could be that girl to him.

  “We’ll have to go on a proper date,” he teased. “You’ll have to dress up for it, though.”

  “I don’t have a problem with that,” I said with a smile. He leaned in and kissed me again.

  “Should we return to the party?” I nodded. We got dressed and kissed again before heading downstairs. When we finally returned, all the guys were staring at us.

  “Woah, Ben! You fucked the stripper?” asked Jay.

  Ben wrapped his arm around me and replied, “No. I’m dating the stripper. And her name is Lexi.”

  “Actually,” I said, looking up at him one more time for reassurance. “You all might know me better as Mike.” I watched their jaws drop and I pulled the wig off to reveal myself.

  I waited for the backlash but was pleasantly surprised. Josh, of all people, started to clap and everyone else in the room followed his lead.

  Ben pulled me in close for a hug as the guys applauded us. I suddenly felt like I was in my own little fairy tale.

  Maybe Lexi meant for me to find that bag after all, I thought. Maybe she was my fairy godmother….

  “There’s one thing I don’t understand,” said Jay, interrupting my kiss with Ben. “If you’re the stripper, then what the hell did you do with all the money?”

  “That’s going to be kind of a long story.”

  Dressed as a House Maid

  Chapter 1

  I had followed Theresa Young on social media for years before she became famous. I watched her videos, scrolled through her selfies, and even listened to a few music covers she did of her favorite bands. I knew she didn’t have a clue who I was, even though I left a comment on every single post she ever made. Occasionally she would like one here or there, but I was too shy to put my real photo on the internet. To her, I was some random fan. I was a total stranger.

  Now she was starring in the highest grossing films and she never managed to lose her charm or charisma. I was as in love with her as two strangers could be, and I would’ve given anything to meet her. Of course, the chances of that happening were getting slimmer and slimmer by the day. The more money she made, the more inaccessible she became. I slowly learned to let go of my fantasy and keep her in my heart as a distant dream.

  I’m almost ashamed to admit that I jerked it to her pretty often. She’s the hottest thing on this planet and no one would ever know besides me. In some of her older videos, when she was still eager for views, she’d wear some pretty skimpy clothing. My favorite were her fitted, spaghetti strap tank tops that perfectly showcased her large breasts.

  I remember one night, pausing the video at the perfect moment. Her pouty pink lips formed a soft O shape and her head was leaning back a few inches. Her soft brown locks slid from her shoulders and down to her back and her breasts were pushed out so seductively. I had locked the door to my room since I was still living at home, and then I pulled out my cock.

  Tugging my cock in front of Theresa’s frozen
picture was exhilarating. I wasn’t the biggest in that department, so I felt more comfortable knowing there was no one there to judge me. When my hand wrapped around it, my palm almost covered the entire length, and my hands weren’t very big. I let go of all my inhibitions and started to pull on my cock while my eyes traveled between Theresa’s soft mouth and sexy breasts.

  I imagined her lips wrapped around my dick, taking all of it in easily. I pretended it was a fetish of hers. I pretended that she got off to sucking my tiny cock and flicking her tongue along it. Then I imagined cumming over her tits and watching my cum slide in through her cleavage.

  In reality, I came all over my jeans and hoped that my mom wouldn’t notice the weird stains that ended up on all of my pants. I was 19 years old, but my mom still did my laundry. I figured I should take advantage of her hospitality while I still could. But the longer I lived at home, the more often I dreamt of being somewhere else with Theresa.

  I remember one of her house tour videos. She had just bought a small mansion in Los Angeles. It was bright and airy, and she looked gorgeous in it. The windows bathed her sexy curves in natural lighting and her skin looked smoother than ever. I imagined her riding me in her luxury living room on her luxury white rug.

  Now, she tried her best not to show too much of her house, but I was still able to find her address pretty easily. People often underestimate what can be used as clues. Fortunately, I only wanted the best for Theresa and had no ill intent, but I often teased the idea of showing up one day to see her. It was just a dream, of course. I had no desire to get arrested or anything.

  One day, however, after a particularly nasty fight with my dad about responsibility and maturity, I found myself more desperate than ever to leave home. I ran up to my room with tear stained cheeks and furiously searched online for anything I could afford. Unfortunately, I only had a part time job delivering pizzas and next to no friends who could live with me. I just couldn’t afford rent by myself and I couldn’t find anything full time.