Man to Woman

by Jane Futa

  I ignored him and chalked it up to him being drunk. “Nah,” I said. “I think I’d know.”

  “That’s not always true,” said Rebecca innocently.

  “I know what a dude looks like. Doesn’t matter how they dress or act,” I reinforced.

  “Dude, could you just shut up,” said Brandon sternly.

  “What’s your problem?” I asked.

  “You fucking are!” he shouted back. I was taken aback and dumbfounded.

  “Okay, dude. Chill. Let’s change the subject.”

  Lauren was laughing at both of us and Rebecca seemed concerned. The four of us started talking about school instead and finished our food.

  I didn’t know why Brandon had been so upset with me, but I was about to find.

  Chapter 2

  A few weeks later came Spring Break. Brandon invited me to visit his place because his parents were loaded. Mine did okay for themselves but Brandon’s house would be like a free vacation and I wanted to take it. He only had one, weird rule: don’t fuck his sister.

  “I’m serious,” he said as he grabbed my suitcase from the trunk.

  “I’m not going to fuck your sister,” I said laughing. His sister had just turned 18 and had a bunch of guys chasing her, so naturally Brandon thought I’d follow the pack. In any other circumstances, he’d have been right, but Brandon’s friendship meant too much to me. Of course that was before I caught sight of his hot little sister.

  We walked into the big, white house and set our suitcases down in the foyer. I followed Brandon to the kitchen to grab some beers and that’s when I saw her. As we turned the corner, I caught a glimpse of the most perfect little ass as she bent over to scour the food left in the fridge. She was humming pleasantly and she had long red hair that draped over her shoulders.

  She was wearing a hot pink sundress and I could see the hint of her ass cheeks peeking out from under the soft fabric. I bit my knuckles to punish myself for my dirty thoughts. All I wanted to do was grab her by the hips and fuck her right there. Suddenly, I knew what Brandon had been worried about and I wasn’t sure how I was going to make it a week around that hot little thing.

  She stood up when she realized someone else was in the kitchen. She closed the fridge door and spun around.

  “Oh, hi,” she said. Her blue eyes sparkled and her skin was the smoothest I’d ever seen. “I’m Sheila,” she said, reaching out her delicate little hand toward me. I walked toward her and took her hand in mine. My cock stiffened at her touch and I hoped it wasn’t noticeable.

  “This is Adam,” Brandon said as he slipped behind her to grab the beers.

  “Nice to meet you, Adam,” she said in a sultry tone. I watched the tip of her tongue glide sensually over her upper lip. Then her eyes scanned my body, landing on my hard cock.

  Horrified, I looked down only to find out that it wasn’t visible yet. Sheila started laughing at me, as if she found out my secret. Shit, I thought. How did she guess I was hard?

  Then Brandon slammed the fridge door and I quickly let go of Sheila’s hand. “Alright, dude. Let’s head up to my room.”

  I followed him out of the kitchen and turned my head back one more time toward Sheila. She had her pouty lips wrapped around her middle finger, sucking it tenderly. A quiet moan escaped me.

  “Where’s your bathroom?” I asked Brandon.

  “Down the hall on your left,” he replied. He didn’t seem suspicious and I was grateful for that. I knew if I was going to be in the same house as Sheila, I’d have to jack off a lot to keep from fucking her. It didn’t help that she was hot and down to fuck. She was practically irresistible.

  I rushed to the bathroom and locked the door behind me.

  My mind instantly raced to the image of Sheila bent over in front of the fridge. I quickly dropped my pants and pulled out my semi-hard cock. I closed my eyes and started stroking it to the sight of my friend’s sister.

  I went up behind her and slid my hands under her dress. I grabbed her hips and pulled her ass to me. She cooed in shocked delight and then braced her hands on the counter for what I was about to do to her. I pulled down her wet panties and found her slit. I slid my finger in and she moaned. My cock throbbed and my head swelled. I rested it at her entrance and pushed in.

  Her moan was loud but soft as my thick cock buried into her tight, virgin pussy. She pulled her small tits out of her dress so they were resting against the counter top. I pushed further into her and then held it there as I watched her squirm.

  I stroked faster, trying to keep my heavy breathing as quiet as possible. I held my cock over the toilet so it would make cleaning up easier.

  I pulled my cock out of her pussy only to shove it back in quickly. Sheila started to cum just from the sheer pleasure of feeling my cock inside her and that sent me over the edge. I started pounding her pussy over and over until my cock swelled and exploded inside of her. I watched my cum start to drip from her tight pussy onto the kitchen floor.

  “What a dirty girl,” I told her as she came down from her orgasm.

  Cum shot out from my cock into the bowl below and I whimpered in an attempt to keep my moans quiet. I braced myself against the bathroom wall and tried to calm my mind down from the image of fucking my friend’s sister.

  Hopefully this will get her out of my system, I thought. I exhaled a few long, deep breaths and then cleaned myself up. I left the bathroom and searched for Brandon’s room.

  Unfortunately, I came across Sheila’s room first and she was lying on her bed with her ass facing the doorway. Her legs were spread wide despite her wearing a dress, and I was able to catch another beautiful view of her ass. Oh, how I wanted to run up and pound her right there.

  I walked away quickly before she could catch me staring at her. I didn’t need her trying to seduce me like she had downstairs. I found Brandon’s room and joined him on his bed. He had started up our favorite video game and tossed me a second controller.

  “Man you suck today,” he said after a I’d died easily a few times.

  “Yeah,” I said with a laugh. I knew it was because my mind kept thinking about his sister’s tight ass, but I couldn’t tell him that.

  “One more round then I’m going to shower,” he said. The round didn’t last long since I was so distracted. Brandon dropped his controller, told me to suck it and then headed to the bathroom.

  I lied down on his bed and stretched my arms behind my head. I tried to shake Sheila from my mind, but I couldn’t. Moments later, the door creaked open.

  “Did you forget something?” I asked, assuming it was Brandon.

  “Yeah,” I heard Sheila reply. “I forgot this.”

  I looked up and saw her crawling on the bed between my legs. What the hell is she doing? I wondered. I wanted to stop her in case Brandon walked in, but I couldn’t move my body. I was completely frozen in the midst of her beauty.

  Within seconds, Sheila had her hands on my pants and slid them down my thighs. She ran her hand over my briefs where my cock lay. She had a hungry look on her face and she licked her lips.

  She’s so fucking hot, I thought. But I can’t fuck her. I could lose Brandon as a friend. But I couldn’t stop her. My hands were glued behind my head and I watched in horrific pleasure as Sheila caressed my stiffening cock.

  She leaned down and kissed my cock through the fabric. “Fuck,” I moaned. I heard Sheila giggle and it only turned me on more. Her giggle was so perfectly young and girly. I wanted to do the naughtiest things to her.

  She reached for the elastic band around my briefs and slid them down slowly. Her eyes widened as she revealed each new inch of my hard cock. I watched my friend’s gorgeous little sister eagerly stare at my dick. It was the hottest moment in my entire life, despite all the casual sex I’d been having at campus parties.

  Fortunately, I could still hear the water running from Brandon’s shower, so I was hopeful I’d have decent notice if he finished soon. Sheila reached her long, slender fingers down and wra
pped them around my cock. She pulled it toward her and began stroking it slowly.

  I closed my eyes and gasped as she touched me. Her thumb glided delicately up the underside of my cock and she circled it just under the head.

  “Fuck,” I moaned through an exhale. I heard her sexy giggle again and I couldn’t help but fall in love with the sound.

  Moments later, she lowered her head and I could feel her breath on the tip. I looked down at her and saw her hair cascading down. Her eyes looked up at me seductively as she opened her mouth. I watched her wrap her pouty lips around the head and I felt her tongue resting against the underside. I was grateful I’d just cum or I might’ve cum in her mouth already.

  She sucked her cheeks in, creating a vacuum on my dick. I moved my hands to my side and rose up on my elbows. She lowered her head further down my shaft and I felt my cock throbbing in her mouth.

  She swirled her tongue in so many different directions that I couldn’t keep up. For an eighteen year old girl, she really knew her way around a cock. I reached my hand out and held it on the back of her head, stroking her hair as she sucked.

  She moved her head up and down, picking up speed each time. Soon, I was adding pressure to the back of her head to push her down further. After she figured out the rhythm I liked, I moved my hand back to my side and watched her expertly suck me off.

  She brought a hand to my balls and started to massage them while she sucked. “Shit,” I moaned again, still acutely aware of the sound of running water through the walls.

  She juggled my balls in her hand and moved her vacuum tight mouth vigorously up and down my cock. I knew I would cum any moment and thought I should give her warning. “I’m going to cum soon,” I told her.

  She smiled as much as she could with my cock still in her mouth, and then she picked up her speed. Oh fuck, I thought. She wants me to cum in her mouth. That’s when I let go. I lay my head back and took in the feeling of her mouth on my cock until my head felt like it was exploding. I shot my load to the back of her throat and I felt her sucking intensify as she swallowed every drop.

  “Holy shit,” I said when my load stopped firing. She pulled off of me and wiped her mouth. Then she smiled at me and ran her fingers through her hair to straighten out the wild strands. Then we both heard the sound of the water shut off. A look of panic flashed across my face, but Sheila only giggled.

  Despite her finding humor in the situation, she quickly left the room and I pulled up my briefs and pants as fast as I could.

  Moments later, Brandon walked in with a towel wrapped round his waist. I tried to calm my quick breath, but fortunately Brandon didn’t seem to notice.

  “Hope you didn’t get too lonely,” he joked.

  “Not at all,” I said, thinking about Sheila on my dick. Brandon got dressed and then suggested we sit outside and get some sun. “Sounds good,” I said, eager for the break from running into his little sister.

  As we walked down the hallway, I noticed the family photos for the first time. I didn’t see Sheila in any of the early ones. Instead, I noticed Brandon sitting next to a young boy.

  “I didn’t know you had a brother,” I said to him, confused.

  “I don’t.”

  “Oh. Then who is this?”

  “That’s Sheila,” he said. “She’s transgender.”

  My heart nearly stopped. “Like what? She wants to be a dude?”

  Brandon stopped and turned back to me. “No. She was born a boy but doesn’t identify that way.” He eyed me suspiciously, waiting for my reaction.

  “But she’s a chick, now, right?”

  “Dude, don’t be ignorant and get all weird.”

  “I’m not,” I said, trying to sound convincing. Little did he know that his trans sister just sucked my dick and now I was trying to wrap my head around it. “I’m just confused.”

  “She’s still anatomically the same…she just dresses and behaves like the woman she identifies as.”

  “So she has a dick?” I felt horrified at the thought, but I had to know.

  Brandon punched my shoulder. “Don’t make me beat your ass. Yes, she has that,” he answered finally.

  I grabbed my shoulder and rubbed it, but it didn’t hurt as much as my ego. Did I really just let a dude dressed as a chick suck my cock?

  A wave of conflicting emotions swept through me. Does this make me gay? I knew it wasn’t gay to think a chick was sucking me off, but I still felt an attraction to her after finding out she had a dick. Fuck me, I thought.

  Brandon and I sat outside and I welcomed the change of scenery. I couldn’t stop thinking about how Sheila had a dick swinging between her legs this whole time. My heart sank as I tried to figure out what all of it meant. Needless to say, I was distant for most of my conversation with Brandon.

  Why do I still want to fuck her? I wondered, worried about my sexuality suddenly. This is going to be one long fucking week, I thought.

  Chapter 3

  The next few days passed easily without running into Sheila. She was staying at a friend’s house for a few days which left me and Brandon to party it up and relax by the pool. His house was like a vacation home and I had no regrets about spending my Spring Break there.

  Today would be the day that Sheila would come back, though. I’d tried to cleanse her from my mind by fucking other women and drinking as much booze as possible, but nothing could prepare me for seeing her again. She was the hottest thing ever and I was trying to lock up my dick because she had her own dick. I was conflicted and yet, strangely aroused by the conflict.

  When she came back, Brandon and I were lounging in his room. I heard the front door open followed by the sound of tiny footsteps up the stairs. Brandon was pounding furiously on his video game controller and I just looked at the ceiling to try and distract myself. All I wanted to do in that moment was head into Sheila’s room and fuck her cute little ass.

  I exhaled. Does that make me gay? I wondered. Everything about her was feminine except for the male member that swung between her legs. I’ve never been attracted to a dude before. But Sheila wasn’t a dude. She was a woman through and through, with one tiny exception. I couldn’t figure out how important or defining that exception was. All I knew is that she was irresistible and no amount of pussy could keep her off my mind.

  Most of the afternoon went by without Sheila and me seeing one another. When we finally did meet again, it was downstairs in the early evening. Brandon had asked me to grab a few beers and Sheila was watching TV in the living room. I passed by the couch on my way to the kitchen and I felt her seductive eyes on me the whole time.

  “Hey,” I said in a struggling voice.

  “Hello,” she said sweetly. She wore a lacey white tank top with a floral skirt that ended mid-thigh. Her creamy skin stretched on for miles. On her feet was a pair of strappy wedge heels. Her blonde hair draped like a waterfall around her face. I wanted to slide my hand under her skirt and pull her ass to me. I bit my lip as I walked into the kitchen to try and control myself. After all, even if I didn’t mind her being trans, my best friend asked me not to fuck her. So I couldn’t, right?

  I grabbed my beers and headed back to the stairs. I peeked over my shoulder one more time before ascending. Sheila was eyeing my ass and licking her lips. Fuck, I thought as my head started to spin with wild desire.

  I rushed back upstairs and set a beer next to Brandon. His eyes were focused intently on the game in front of him. He was in for the long haul tonight. He’d just entered a competition with a few friends and it was supposed to last a few hours. It was difficult for me to sit on my hands idly while Sheila sat downstairs, ready to fuck.

  Half an hour later I heard Sheila’s bedroom door open but I never heard it shut. I waited as long as I could before excusing myself to go to the bathroom. My cock was getting hard and I didn’t want Brandon to see. Not that he would’ve noticed anyway. All his focus was poured into his game.

  I entered the hallway and pulled Brandon’s doo
r closed behind me. Rays of golden sunlight stretched along the width of the hallway to the right of me. They were pouring through Sheila’s bedroom window. I slowly approached with the plan of passing by. As I stepped in line with the doorway, I saw Sheila lying on her stomach again. Her skirt was lifted high enough that I caught a glimpse of her pink satin panties.

  I swallowed hard and bit my knuckles to keep from moaning. She looked like she was reading a magazine or looking at her phone. I tried as hard as I could to move my feet and leave her doorway but I was frozen in place. I just stood there staring at her perfect little ass.

  Then Shelia shifted her legs and I saw a small pouch where her balls would be. I was strangely more turned on. I couldn’t shake the attraction, even though it felt wrong. No one could know I fucked a trans woman, I thought. Especially not her brother.

  Sheila turned her head slowly over her shoulder and caught me staring at what lay under her skirt. She smiled slowly and then shifted to her side. She leaned on one elbow and used the other hand to pat the spot next to her, inviting me in.

  I looked down the hallway toward the bathroom that I knew I should head to instead, but my feet walked further in. As if on autopilot, I closed her door behind me.

  “Lock it,” she whispered. I reached over and turned the knob for the lock. I exhaled when I heard it click, as if I could finally relax into myself.

  I turned back toward her and let my eyes wander across her perfect body. She flipped the strands of her hair back and smiled. I took a step toward her, wondering if I would cross into a world I couldn’t come back from.

  I heard Brandon shout from the room next door and knew it was safe to continue. At least, it was safe for now.

  I sat on the edge of the bed, leaning my hand down on the bedspread. It lay inches from Sheila’s taut stomach and I wasn’t sure who should make the first move. My nerves were on end now that I knew Sheila was trans. Everything was easier when I thought she was a normal girl. Then again, her uniqueness is what drew me into her.