Man to Woman

by Jane Futa

  I’ve never wished to have a pussy so hard in my life. I wanted him to fuck me like his little slut. I wanted him to pound me the way I couldn’t be pounded. Despite having all the wrong parts, I couldn’t stop kissing him and letting my hands travel down his spine.

  He placed a hand on my neck and rubbed his thumb against my skin. His hand lowered slowly to my chest, cupping my padded breasts. I felt the fabric rub against my nipples and I imagined that my breasts were full and round and something he would desire. His hands moved to my hips and then he brought me in close to him.

  I didn’t know if he could feel it, but our erections were gently touching. I smiled knowing how hard he was for me, but I worried he would know I had a cock. He didn’t change his approach, though. He kept kissing me and letting his hands roam over my body until they found my ass. He squeezed my ass cheeks tight and then gave them a little spank.

  “Oh!” I cried out as the sting hit me.

  “You like that?” he whispered seductively.

  I nodded shyly and he slid his face to my neck, kissing me softly. I bravely reached my hand for his cock and felt it through his shorts.

  “Oh fuck,” he moaned into my ear. “Be careful with that thing. It’s ready to blow. I don’t want to do anything you’re not comfortable with…”

  He was both showing concern and asking how far I was willing to go at the same time. I was no lady, but even I was starting to think he was good with them. I wanted to go as far as he wanted me to, but I just couldn’t. How could I explain to him who I was and what I had between my legs?

  His hands slid under my skirt and I felt his rough palms against my cheeks. He breathed heavily on my neck and my cock grew harder and harder. I couldn’t decide what to do so I just let him continue. I nervously awaited the moment when he found out I had a hard cock.

  But his hands never left my ass. He lifted my skirt up by my hips and slid his hand in my panties. His finger parted my cheeks and played with my asshole. I clung to him to keep from falling because the pleasure was so intense. I’d never had my asshole played with before, but I loved it.

  He sensed my knees were buckling and swept me up quickly like a superhero. Then he laid me on a soft patch of dirt and climbed over me. He slid his tongue into my throat again and let his hands wander over my freshly shaved legs. It felt so good to have his hands on me, and I never wanted it to end.

  He leaned into my ear and asked, “Do you like anal?”

  My eyes widened in disbelief. Was he giving me an out? I’d never done anal before, though! I lied to him and nodded. He spun his index finger in a circle, signaling me to flip over. He took off his shirt and lay it in the dirt for me to rest my head on.

  This guy wants to fuck a strange girl at a concert, and he’s still a fucking gentleman! I couldn’t believe I was so lucky. Sorry girls, I’m stealing one of the good ones, I thought.

  Jason slid his pelvis down to my thighs. Then he lifted my skirt up and I was grateful my cock was tucked up against my stomach. He pulled my panties down and grabbed my ass. Then he spanked it one more time.

  He unzipped his pants and spit into his hand. I heard him stroke his cock a few times. Then he laid his shaft along the line of my ass, resting his head by my lower back. He’s so long! I was suddenly very, very worried about agreeing to let him fuck my virgin ass.

  He spit again, this time letting the saliva drip straight down to his cock and spill over my skin. He stroked himself again and slid the head between my cheeks. I clenched my eyes shut as I prepared for the pain. He leaned down and whispered, “You don’t want to miss the show.”

  I opened my eyes again and saw what he meant. Hundreds of colored lights and lasers were spilling through the trees. The music was loud enough to hear but quiet enough that I could still hear Jason’s heavy breathing. My mind spun into a state of euphoria.

  Then he shoved his cock in.

  “Oh!” I cried out in pain as he split me wide open. But as he pushed further in, the previous euphoria exploded. I was suddenly wrapped in warm, vibrant color and my body was pulsing to the electronic music.

  Soon Jason’s cock was all the way inside me and I never felt so whole and complete. It was as if he was a missing piece of me this whole time. He groaned like a wild animal and leaned over me.

  “You’re so fuck hot,” he said as he buried his cock into my ass. He reached his hands for mine and weaved his fingers inside their grip.

  “So are you,” I told him through a moan. He pulled his cock out slowly and as my I felt myself relax, I suddenly wanted him to slide it in deep again. When he did, it was as if my head had split open and the entire universe became ours.

  Once he was sure that I was comfortable, he really let loose. He started pounding my ass hard and fast. He heaved and grunted all while we watched the lights and concert go on just outside of our little oasis. As he pounded me over and over, my cock slid inside my panties against the ground, and I knew I would cum when he did.

  He let out a load roar and released his hot load deep into my ass. The head of my cock swelled and then exploded hot cum into Jessica’s panties. I moaned as he filled me and then he collapsed above me.

  He rolled over onto his side and I rolled over to lay in his arms. Then I saw him look down with a shocked expression. I followed his gaze to see that my erect cock was poking through my panties and skirt, and I was horrified.

  Jason didn’t say anything and I wasn’t about to give him a chance to. I tucked myself in and fixed my outfit. Then I bolted quickly back to Nathan, filled with embarrassment.

  That was so reckless and stupid of me, I thought. My only consolation was that he still didn’t know who I was. I finished the night with Nathan and then he dropped me off back home. I carefully snuck into the house before anyone could see me. Then I changed out of my rave outfit and back into my regular boy clothes.

  The clothes hung oddly on my body. They were baggy and unflattering. I threw myself on the bed and curled up with a soft pillow as I thought about the crazy events of the past 24 hours. A few hours later, there was a knock on my door.

  “Who is it?”

  “Jason,” I heard him say, and my heart nearly stopped.

  Chapter 6

  I cleared my throat and sat up on my bed. “Come in,” I told him in a low, deep voice as if I was trying to make up for my lack of manliness. The door opened slowly and Jason came in. He brushed his hand through his hair and smiled at me. He seemed different somehow, but I couldn’t place it.

  “How was the festival?” I asked, trying to fake disappointment about not being able to go.

  “It was pretty good. I met this super hot chick there,” he said.

  “Oh yeah? Sounds awesome.” I tried to sound normal but my throat tightened with heartbreak.

  “It was. I fucked her ass in the middle of some trees.”

  The hot chick he was talking about was me? But that chick had a cock… “Bad ass,” I said, unsure of where he was going with this story. Maybe he’s just going to omit that part. Maybe he’s going to pretend like everything was normal.

  “Oh,” he said, “and I think I have something of yours…”

  My eyebrows furrowed with confusion as he reached into his pocket. Then he pulled out a few gold coins from the skirt I wore earlier. I didn’t say anything. I didn’t want to admit it was me. I didn’t want to be confronted about dressing up like a woman and then letting my best friend fuck my ass unknowingly. I also was afraid I’d out myself unnecessarily.

  “I don’t know what you-“ I started, but Jason pressed his finger to my lips to hush me.

  He leaned his lips to my ear and whispered, “I know it was you earlier.” My heart raced and adrenaline shot through my body. “Now why don’t you go put that skimpy outfit back on and let me finish what you started.”

  I couldn’t believe what he was saying. Did he want to fuck me again even though he knew it was me? I was speechless and immovable. Jason stepped back and grabbed my hands,
pulling me to my feet. “I’ll turn around while you change, if you want.” Then he walked to the wall and stared at it.

  In a fit of confusion, I moved to my closet and found the outfit I’d worn earlier. I left the cum stained panties on the floor and put the rest of the pieces on, including the wig. As if by magic, I felt like I had turned back into Crystal and I walked over to Jason, wrapping my arms around him.

  He turned around to face me and smiled the same warm smile from a few hours before. Then he leaned down to kiss me.

  “I don’t understand,” I said.

  “I think I’ve liked you for a while,” he started, “but I didn’t want to admit it. But when you dressed up like that…” his eyes scanned my body from my breasts to my thighs, “I couldn’t deny it. I knew I had to have you.”

  I smiled in a fit of elation. Then he reached his hands down and grabbed my ass again. He stepped away from the wall and pushed me up against it. I placed my hands over my head and he gripped my wrists with one hand. Then he lifted my skirt up.

  “No panties…good girl,” he said with a smile. Then he whipped out his cock again and spit on it. He pushed the tip against my hole and slid it in. This time, there was no pain. It was all pleasure as he filled me up with every inch. “You’re my good little slut, aren’t you?” he asked as he slid his cock in and out.

  “Mmhmm,” I moaned.

  “I’m going to cum so hard in your tight little asshole.”

  “Please cum for me,” I begged him. He started pounded me harder against the wall. He put his hands on my hips for support and pushed deeper and deeper inside of me.

  “Fuck!” I cried out as I came against the bedroom wall.

  “Shit!” he called as he filled my ass with his cum for the second time. His heavy breathing started to slow as he lowered his head to my shoulder. Then he pulled his cock out and spun me around.

  “You’re so amazing,” he told me. “I hope you dress like this more often.”

  “What about all of our friends?”

  “Fuck ‘em. You let me handle them.” I couldn’t help but smile. We lay down on the bed together in each other’s arms. I closed my eyes and heard the pounding of electronic music and saw the rainbow colored lights.

  Then we drifted into sleep with smiles on our faces.

  Trapped by My Best Friend’s Sister

  Chapter 1

  I’d only been friends with Brandon for a few months, but we grew pretty close in a short amount of time. We shared a lot of the same hobbies and taste in music. We even were going for the same major at school which is how we met in the first place. We both wanted to graduate with an engineering degree and make the big bucks. Brandon and I shared a class and happened to sit next to each other. We’d been tight ever since.

  Since we both lived on campus, I’d never gone to Brandon’s house or met his family, and he didn’t share a whole lot about them. I didn’t question it. Most college students were happy to be away from family. The newfound independence didn’t lead many of us to chatting about our lives back home. Instead, we were trying to live it up on campus and create new experiences.

  “Want to party this weekend, Adam?” Brandon asked me.

  “You know it, bro,” I said. We bumped fists and grinned at each other. Brandon wasn’t known to be super wild, but he always attracted the hottest girls. To me, that’s all that really mattered. As his sidekick, I usually got to score with a hot chick too.

  That weekend party ended up being typical of most weekends for us. Brandon played the quiet loner type, despite my constant presence next to him. Within an hour, the two hottest chicks at the party were flirting with us. They bit their lips constantly as they spoke, as if they could cum just from talking to us. We played hard to get and pretended that sex wasn’t our agenda when it most certainly was.

  After 30 or so minutes of pointless small talk, the four of us found a bedroom upstairs and locked the door. It wasn’t the first time Brandon and I shared a room with two girls. Party girls always seemed down for anything.

  Now I wasn’t gay or anything. Brandon and I didn’t rub dicks or anything like that. We just watched each other fuck our girls and occasionally switch. Watching his cock isn’t gay if it’s fucking a pussy. At least that’s what I told myself.

  The bedroom we picked had one bed which was a first for us. We looked at each other to mentally check in. We both shrugged it off and laid our girls on the bed. Brandon stood on one side and I was on the other. Our two girls lay head to head, each pair of legs facing the dude who was about to fuck them. We didn’t even have their clothes off before they started making out with each other.

  Brandon and I looked at each other with utter satisfaction. We grinned and nodded, following with a sly fist bump across the bed. Then we each made our moves on the girls.

  My girl was Lauren and Brandon’s was Rebecca. I leaned down and pushed Lauren’s faux leather skirt up to her hips, revealing a hot pink thong. I could see a small wet stain between her legs where the slit of her pussy rested. I licked my lips and ran my index finger across it.

  Lauren moaned into Rebecca’s mouth and I looked up to see Brandon removing Becca’s jean shorts. Brandon’s girl had bright blue panties on. I couldn’t see if they were wet or not but judging by Brandon’s expression, they were soaked. His eyes were wide and wild and he quickly removed her panties.

  I reached for the strap of Lauren’s thong and pulled it down her silky legs. She wore white sneakers and I didn’t bother removing them. Rebecca had on black heels which were kicked off the moment we entered the room.

  Brandon and I simultaneously knelt down between our ladies’ legs. We spread them and then stretched our tongues out toward their wet paradise. Occasionally Brandon and I looked up at each other as we licked each girl’s pussy.

  Suddenly, I felt Lauren’s hands resting on the back of my head, holding me close to her cunt. She rocked her hips back and forth and moaned louder than any girl I’d had before. “Yes! Oh yes!” she cried in a half hoarse voice.

  Rebecca on the other hand was a quiet one. She made “mmm” sounds more than she screamed expletives. The important thing was that we both knew our girls were having a good time.

  When both our girls had cum in their own unique ways, Brandon and I stood up. We dropped our pants at the same time and started to stroke our already hard cocks. I was a little bit bigger than Brandon but he never seemed bothered by it. We took our cocks and rested their heads against the slits of their wet cunts.

  Brandon pushed in first, moaning as he slid into Rebecca. I liked to take my time and really appreciate the sensation. I closed my eyes and leaned my head back as the head of my cock split the folds of Lauren’s pussy. Then I felt it stretch around my cock as I pushed in farther.

  “Oh, fuck,” I cried in a loud whisper. I heard the girls giggling, despite their tongues still plunging down each other’s throats. The giggling was hot, and the moans between the four of us were even hotter. I felt my balls swell and my cock throbbing as if already about to cum.

  Brandon leaned his hands down on either side of Rebecca and started pounding his cock into her. The bed shook and caused Lauren’s pussy to slide up further on my cock.

  “Shit,” I moaned again. I looked down at Lauren and then lifted up her tank top. She had the perfect stomach, the kind you just want to cum all over, and breasts that fell at a perfect 45 degree angle off her chest. Luckily for me she wasn’t wearing a bra.

  When I had her shirt lifted above her tits, I grabbed one in each hand as if they were my support. Then I started to pound Lauren to the rhythm that Brandon was pounding Becca.

  I watched Brandon’s cock slide in and out of Rebecca and I felt even more aroused. I watched Rebecca’s tits bounce as Brandon ravaged her body. Then I looked back at Lauren’s tits in my hands and felt like I would explode.

  When Brandon started yelling like a wrestler, I knew his cum was filling up Rebecca’s tight pussy. The sound of the girls mixed with Br
andon’s orgasm cues made my cock swell. Soon, I was filled with a white hot electricity and I felt my cum spill into Lauren’s cunt. She moaned louder which intensified my orgasm.

  We hovered over the girls for a moment while we caught our breath. Then Brandon and I looked up at each other and grinned.

  Lauren and Becca stopped kissing and Lauren was looking up at me. “I’m starved. Do you guys want to grab something to eat?”

  I couldn’t help but laugh at how casual she was. It was refreshing. “What do you think, bro?” I asked Brandon.

  “I could get some grub,” he said, and quiet Becca just nodded in agreement.

  “Great!” shouted Lauren. Brandon and I pulled our half limp cocks out of the girls and then pulled up our pants. The girls got dressed and giggled at each other while trying to pick a nearby restaurant.

  We agreed on a Mexican place that had late hours and piled into Brandon’s car. We ordered our food and sat down to talk for the next hour and a half. We covered many topics, but only one that stood out to me that night.

  Lauren started. “So like…have you guys ever accidentally fucked a dude?” She leaned over the table toward me with wide, daring eyes.

  “What do you mean?” I questioned. “Like with my boy Brandon?”

  “No, no. Like if you thought he was a chick.”

  “Why would I think that?” I asked.

  Rebecca jumped in, “Because they might be transsexual.”

  “Oh,” I said, it clicking finally in my head.

  “I don’t think this is a cool conversation,” said Brandon. I looked at him suspiciously. Brandon and I talked about dirty, kinky stuff all of the time. I couldn’t figure out why he was averse to this topic.