Man to Woman

by Jane Futa

  That’s when I saw it. Hiding inside a pair of bikini bottoms was a small erect cock. My mouth hung open. I tried to rationalize what I was seeing, but I couldn’t. I still wanted her. I didn’t why but I wanted her more than ever. She was hotter with a little cock. I wondered if she’d let me fuck her little asshole.

  I didn’t have to ask. I leaned in and kissed her and she was pleased. She practically made her tight little asshole available to me. She turned herself around and pulled the bikini bottoms to the side. She found a tree nearby and gripped onto its trunk. She bent over slightly, exposing her perfect little round ass to me.

  I looked around to make sure no one would see. I still didn’t really care if we got caught. I had to fuck her, cock or no cock. I walked up behind her and rubbed her back. I stroked her hair and spanked her ass. She moaned the cutest little moan.

  I ran my hand along her crack and teased her asshole. I bent over and spread her cheeks wide. I stuck out my tongue and licked her little hole. She pushed her hips back into me and cooed. I slid my hands up and down her thighs as I licked. I slid my tongue inside of her, feeling what I was about to fuck.

  God I loved her ass. It was the cutest little ass I’d ever seen. I lifted my head up and just stared at it for a moment. I rested my cock along the crack. I leaned over her and kissed her. My balls pressed up against her.

  Then I felt it. My balls slid against her balls. It was the strangest yet most erotic feeling of my life. They weren’t supposed to be there, but they turned me on even more. I just wanted to feel out balls slap together as I fucked her.

  I spit along her crack and rubbed in my saliva. I fingered her asshole with a single finger. Then I slid a second one in and a third. The more I shoved inside of her, the more she moaned. I knew I couldn’t hold back much longer. I wanted to fuck her ass so badly.

  I pressed the tip of my cock against her hole. She looked back at me over her shoulder and smiled. She pushed her ass back onto my cock. My jaw dropped as I watched it stretch around my shaft. It felt so fucking good. I loved being in this tiny trans girl’s ass.

  She slid her hips further toward mine until her arms were completely extended. I grabbed her hips and pressed myself further inside. I pushed and pushed until I was all the way in her. My balls dangled against her balls and I felt like my cock would explode right then.

  I exhaled and held it for a moment. I wanted to pound her before I came. She was perfect and patient. I reached around and played with her small tits. I rolled her nipples in my fingers. She bit her lower lip and moaned. I knew I was going to fuck this little body so hard.

  I wrapped my hands around her hips and gripped them. Then I pulled my cock out slowly. She moaned the entire way. I groaned the entire way back in. I pushed in and out slowly until I’d gotten used to the sensation. Then I started to thrust in faster and deeper. She seemed to enjoy every move I made.

  I pounded my cock in and out of her tight little ass. It was the hottest thing. Her balls peaked out of her bikini bottoms. I reached under and fondled them as I fucked her. I’d never held a pair of balls that weren’t my own before. It was fucking hot.

  I pounded her up against the trunk of the tree until my cock was begging to come. I shoved it deep inside of her and let my hot load explode. I couldn’t believe how good it felt to come inside of her. Her ass gripped tightly around my shaft as I let go.

  “Fuck,” I moaned as quietly as I could. My cock pulsed against her tight hole. She smiled as I came. “Did you come?” I asked, suddenly feeling bad as my semen spilled back down toward me.

  She shook her head but had a silly grin on her face. I pulled my cock out of her slowly and she gasped. I exhaled and tried to catch my breath. She reached for my shoulders and pressed down on them. I dropped to my knees. I knew what she wanted, but I’d never done it before. She’d given me the best orgasm I’d ever had, though. I wanted desperately to please her.

  She walked up to me. Her erection was inches from my face. It was only contained by her bikini bottoms. I reached up and pulled the fabric down. Her tiny cock bounced out toward me. It was only a few inches long. I looked up at her as she had with me. Then she nodded and smiled.

  I opened my mouth and she slid her tiny cock in. It was the strangest sensation, but I loved it. I loved feeling her small dick in my mouth. She stroked my head as I slid up and down it. I flicked my tongue along the underside. I mimicked what she had done for me.

  I reached my hand up for her ass and slid a finger inside of her hole. That really got her going. She leaned her head back and groaned. I fingered her cum filled asshole while I sucked her dick. She rocked her hips back and forth into my face. I exhaled wild gusts through my nostrils. I’d never sucked a cock before.

  I felt it grow and throb inside my mouth. I knew she was close to coming. I slid a second finger inside of her while I sucked. She let out a loud howl. Then I felt a pool of hot liquid spill toward the back of my tongue and down my throat. I swallowed every drop eagerly.

  She pulled herself out of my mouth and I stood up to kiss her. She licked her own come from inside my cheeks. I brought my cum covered fingers to my mouth and cleaned them. She smiled at me.

  We dressed ourselves and kissed one more time. She took my hand and led me back toward the campsite. It was so dark now that I worried we might be lost, but Sarah seemed to know her way around.

  When we had finally returned, all head faced us. The crowd erupted in applause and laughter. I blushed and tried to look innocently confused. “What’s that for?” I asked.

  Matt smiled and said, “Come on, man. We heard you guys moaning back there. You weren’t that quiet.” I blushed again. They all knew we had just fucked but I wondered if they knew about Sarah’s little secret.

  We finished the night with more beers and food. Eventually Matt and his friends went back to his campsite and I stayed with Sarah. Since everyone knew we had fucked she wasn’t shy about showing her affection. She sat on my lap with her arms wrapped around my shoulders while we hung out with her friends.

  At the end of the night I asked Sarah for her number. She gave it to me and kissed me. “Normally people just fuck me,” she said. “You seem like you’re pretty unique though.”

  “So are you,” I told her. “And not just because…”

  “It’s okay. I get you,” she said. She smiled at me. I reached my arm around her and kissed her one last time before we went to bed.

  The next morning the RV was gone before I woke up. My heart broke a little but I comforted myself with the knowledge that I had her number. I quickly sent her a text but knew the reception would be bad until we left a few days later.

  ---

  On the way home, my phone lit up with texts from Sarah. I was ecstatic that she already missed me. We made plans to meet up again since she lived within thirty minutes of my house. I felt like I had a girlfriend suddenly.

  Then it occurred to me that I should let my friends in on my little secret. “Guys,” I said, looking around the car. “I need to tell you something about Sarah…”

  I didn’t care what they thought, I wanted to be with her. I at least wanted to give a relationship with her a fighting chance. “She isn’t exactly what she seems.”

  “What do you mean?” asked Matt. “Like she’s a dude or something?”

  I was silent. I hadn’t expected him to guess so quickly. “She’s trans, yes,” I added for clarification. Everyone’s jaws dropped. They didn’t think that would actually be the case.

  “That’s cool, Gene,” said one of Matt’s friends. He leaned forward and put his hand on my shoulder. I smiled and thanked him.

  “Yeah man. We don’t care,” said Matt. I smiled wider. I texted Sarah back and let her know how much my friends liked her. She asked if they knew about her little secret. When I told her they did she sent a string of happy emojis.

  I was happy too.

  Plaything

  Chapter 1

  It was the summer after my first yea
r at college. I hadn’t seen my best friend Bryce or his family all year. We grew up together in the same neighborhood, right across the street actually. But when it came to deciding on a college Bryce and I had separate ideas in mind. Bryce thought college was a waste of money and time, at least before he had worked a few years first. I wanted to get in while I was 18 and out with a good degree while I was still young. I wanted to have a stable career early.

  Bryce did take a community college class here or there as he could afford it. He worked for a company that fixed arcade games and vending machines. Don’t ask me how he landed such a specific job right out of high school, because I still scratch my head over it. It paid more than minimum wage, so he was happy. It also allowed him to take classes at night. Because of that arrangement, I was probably going to be sitting on my ass all summer alone while he worked. I had other friends but they had moved to other states for school and very few of them planned on heading back for the summer.

  One person I could count on being home, though, was Bryce’s hot MILF mom. She was recently divorced, making her that much more irresistible. I swear she had to have been Bryce’s stepmom or something because she looked way too young to have given birth to him.

  Her name was Wendy but I always called her Mrs. Matthews out of respect. That’s how the kids were raised in my town, and I still called her that to this day. I knew I would be able to spy on her from time to time from my bedroom window, like I used to do when I was going through puberty. I don’t know how many times I jacked off to her taking her clothes off. The damn woman never closed her curtains. Not that I was complaining…

  Mrs. Matthews had a gorgeous, curvy figure. Her breasts were full and her hips matched perfectly. She had the ideal hourglass shape that all the women were after. If only they knew it was pointless to attain. Only goddesses had perfect bodies like that.

  She was also a brunette, with long wavy hair. I could never understand how she looked so beautifully manicured day in and day out. I had never seen her with her hair in a bun or wearing a pair of sweatpants. She was as unreal and fantastical as they come. Of all the times I watched her undress through her bedroom window, I mostly just saw sexy lingerie or completely nudity. Never once was there a pair of cartoon pajamas or baggy t-shirts. Not that I minded that in a girl, it just wasn’t how Mrs. Matthews was.

  Anytime I think of her naked, I always remember the time I had walked in on her in the shower. It wasn’t too long ago, I had just turned eighteen. It was right after graduating high school and I had teamed up with Bryce on his X-box. His speakers were loud so I hadn’t heard the water running. When we had a break between levels I ran to the bathroom and was shocked to find Wendy showering.

  What had confused me was that she had her own bathroom attached to the master bedroom. I would later learn that she had a plumbing issue and needed to use the guest bath. To this day, I always wonder why she didn’t lock the door. I always wondered if maybe she wanted her son’s best friend to walk in on her.

  Of course that was just a little fantasy I told myself. I didn’t actually believe she’d have any interest in a scrawny boy like me. I was always told I’d fill out during puberty, but I never quite did. I was on the shorter side, though not too short. My limbs were long and stringy for a boy. An ex-girlfriend of mine even used to tease me for having hips. I remember rolling my eyes until I had inspected my figure in the mirror later that night.

  I was horrified to find out I really did have a killer pair of hips. In fact, my entire physique had always been kind of feminine. I always tried to downplay it though by acting like a total jackass. That’s how real men were supposed to act, right?

  So when I had walked in on Wendy in the shower that day, I was surprised that she hadn’t noticed me at first. She had her hands up by her head, massaging shampoo delicately into her long locks, and her breasts were pressed out like they were begging to be touched.

  My cock had become rock hard while I watched her, but fortunately the steam hid it from view. I had watched Mrs. Matthews lather her perfect, sexy body for a good two or three minutes before she realized I was standing there. When she caught me, she only smiled. I swear to this day that she winked at me too, but the steam was so thick I couldn’t be sure it wasn’t just my silly, hopeful imagination.

  “Sorry, Neal,” she had told me. “I needed this bathroom for a minute.” But she hadn’t shied away. Instead, she faced the full front side of her body toward me. Even through the steam, I could make out the tiny, trimmed patch of pubic hair just above her pussy.

  I had left quickly to go to the master bathroom. My hard-on that day wasn’t going to go away until I jerked off. I whipped out my underdeveloped cock from my pants and started tugging it furiously over the sink. I’d closed my eyes and imagined Mrs. Matthews body the way I’d seen it. Except in my fantasy, I was licking every inch of her while she moaned.

  It took mere seconds for me to come, and that’s where the real embarrassment had begun. I wasn’t aware at that moment of the plumbing issue. There was no water in the entire bathroom. I’d turned on the faucet to wash away my jizz and nothing came out.

  Fuck, fuck, I’d thought. I tried to clean it up with toilet paper, but I just created a sticky mess. My heart raced as I tried to find a solution. A few minutes later there was a knock on the door.

  “Are you okay in there?” asked Bryce.

  “Yeah, just a minute!” I quickly tossed the sticky wads of toilet paper in the nearby trashcan and left.

  As far as I was aware, no one had caught me, but I couldn’t help wondering about that incidence as I pulled into my old neighborhood. I parked in the driveway and stepped out, my gaze instantly searching Bryce’s house for a sign of his sexy mom.

  I’d never told Bryce that I thought she was hot. That just wasn’t the sort of thing you’d tell your friend in this town. They’d be freaked out by it and it would be seen as a sign of disrespect. Instead, I kept it quiet all these years, even though Mrs. Matthews was my dream girl.

  A car pulled into Mrs. Matthews’ driveway and I instantly recognized it. She stepped out of the driver’s seat turned to me and waived.

  “Neal! How are you doing, sweetie?” she called from across the street. She was sexier than I had remembered, despite thinking of her gorgeous, curvy body every night when I jacked off. She was wearing a blue sundress that flared out at the hips and had tiny straps to keep it up above her large breasts.

  She wore strappy white heels and had a matching clutch. She ran over to me and my heart started to race. I watched her breasts bounce up and down as she jogged and I bit my lip. Oh, the things I wanted to do with her!

  “How are you? How was your first year of college?” She wrapped her arms around me, smothering my head in her chest. I would’ve happily died there.

  “It was okay,” I said. “It’s harder than I expected.” She pulled back and stroked my face.

  “That’s a good thing, right?”

  I shrugged. It would’ve been nice if college was easy. It wasn’t the classes that were that hard, it was the stupid rules for parking and attendance that made everything a bitch. I pretended though that I was being challenged intellectually, in case that was the kind of thing that would impress Wendy Matthews.

  I wasn’t sure what kind of guy she liked. She obviously didn’t have a good relationship with her ex-husband and he was the most alpha male guy I knew. He drove a motorcycle, made good money, and was ripped. The fact that they had gotten a divorce always gave me hope. Of course, deep down I knew I could never end up with a girl like Wendy. If I could then I definitely shouldn’t since she was my best friend’s mom. Still, it was my favorite fantasy to turn around in my mind.

  I looked up at Wendy and smiled. Her eyes sparkled as she looked at me. Her skin was sun-kissed and she smelled like exotic flowers. I took a deep breath in and exhaled slowly. I could stand next to her for my entire summer vacation.

  “So what are you going to do this summer?” she asked. �
��Do you have a job lined up or anything?”

  “To be honest, I was thinking of taking it easy,” I told her. I didn’t really need the money because of my student loans, and while I knew the smart thing would be to work I was kind of lazy about it. I just wanted to enjoy my summer vacation like I did when I was in high school.

  “Oh, well there’s no shame in that.” I knew she said that of course because she never worked. She had always been a stay at home mom and housewife. When she got divorced, she got enough money from it that she still didn’t need a job. In fact, it made me wish I was a woman so I could land that kind of set up.

  “Well, if you do need some work and don’t mind doing a few odd jobs, I have a few things you could do,” she said. I smiled.

  “I’d do those things for free, Mrs. Matthews.”

  She blushed. “Please, Neal. Call me Wendy. And I wouldn’t think of it! I’d pay you handsomely of course.” She turned her shoulder toward me and smiled bashfully. “Well I better get back for now, but you call me any time, you hear?”

  I nodded and watched in a daze as she ran back to her house. Her ass made the skirt of her dress sway from side to side as she crossed the street. I knew there was nothing I could do about it, but I was absolutely in love with her.

  As hot as she was, it wasn’t just that. She had the sweetest, most caring heart of anyone I’d ever known. She was smart and funny…but I knew I was only allowed to admire her from afar. Still, she had really set the bar for the kind of girl I was looking for. I wouldn’t take anything less than the greatness that was Wendy Matthews.

  I grabbed my suitcase from the backseat and headed inside. My parents weren’t back from work yet so I had the entire house to myself. I had planned to eat first thing when I got home, but after seeing Mrs. Matthews again, I had other plans.