Man to Woman
Page 33
She’s wearing a thong, I thought and smiled to myself. I slid my hands back up her back to her dress straps and tugged them off her shoulders. I kissed her neck, her shoulders, and then her cleavage, before I pulled the dress down to her waist. She gasped as I released her bare breasts to the air, and I felt her nipples harden against my fingers.
My eyes started to adjust to the darkness and I walked her to the bed. She sat down on it and looked up at me like she had on the plane. I quickly removed my shirt and tossed it to the floor. She unfastened my shorts and slid them down with my briefs.
I stood there naked with her breasts hanging down below me. She took my cock in her hand and started to stroke it. Then she put her mouth on it again. I leaned my head back and groaned, running my fingers through her hair. “Fuck,” I cried. “I missed this.”
She pulled off for a moment and smiled. “You did?”
“Are you kidding? I haven’t been able to stop thinking about you!” With that, she lowered her mouth again and swallowed my cock whole. She moved her mouth back and forth and I felt the tip of my dick swell against the back of her throat.
“Wait, I’m going to cum,” I warned. But she kept sucking and rolling my balls in her fingers. I pulled out quickly. I wanted to cum but I wanted to see her naked first.
“What’s wrong?” she asked.
“I want to see you naked.”
“Oh,” she said, sounding uncomfortable. “Well there’s something you should probably know first.” She looked down. I could tell she was embarrassed and afraid.
“Whatever it is, I’m sure I won’t care.” I didn’t want to ask if she had a cock, because if she didn’t it would be really awkward. So I waited in silence for her to confess to me her secret.
“I’m not exactly what you think I am.”
“What’s that?” I asked. She stood up, keeping her gaze to the side. She grabbed my hand, slid it under her skirt and landed it between her legs. I felt a small, hard dick and balls. I swallowed. So she was trans. But for some reason that only made me want her more. She was the hottest thing I’d ever seen, and her secret just made her hotter.
I left my hand on her cock while I leaned down to kiss her. She was surprised and looked up at me with wide eyes. “I don’t care,” I whispered. She kissed me hard and moved my hands back to her breasts. I rolled her nipples between my fingers while our tongues danced.
She moved her hands to her waist and slid her dress down her hips and to the floor. Then she pulled her thong down and I finally saw the complete package. She was a perfectly curvy, sexy woman with a small penis.
My cock hardened more and my balls swelled. I wanted to fuck her fast and hard. I wanted to love her like she’d never been loved before. I stepped closer to her and felt my cock brush against hers. The feeling of her cock touching mine while my hands fondled her breasts nearly made me cum. It was strange, yet arousing. It was taboo and unexpected. I absolutely loved how erotic it all was.
She dropped to her knees again and took me into her mouth. She sucked while I reached down to fondle her tits. I leaned my head back and groaned again. I was completely in awe of her sexiness. She stood up and bent over the bed, showing her ass to me. Then she reached down and spread her cheeks wide.
I stepped up to her and let my cock rest against her lower back. I ran my hand up and down her spine and then grabbed her ass. I squeezed it and then gripped her hips. I spanked her ass and she moaned which only made me want to fuck her more.
I spit on my cock and stroked it a few times. Then I pressed the head of my dick to her ass and pushed. It was so fucking tight. I couldn’t believe how tight it was. She moaned as I slid into her and my balls touched hers. I reached around her to grab her breasts again and my whole body tensed. I slid back out of her and pushed in again, making us both moan in the darkness.
“Fuck me hard,” she said. How could I say ‘no?’ I started thrusting deep into her. I pounded her ass over and over on the bed. She started screaming and I gripped her hips for support. Within minutes I was shooting my load deep into her tight little asshole.
“Fuck! I’m cumming!” I screamed. Then I heard her moaning as if she were cumming too. I felt her balls swell up and her back stiffen. Then I pulled my cock out of her and watched my cum spill slowly out of it.
I was out of breath and so was she. I lay down next to her and stroked my hand over her head. “You’re so beautiful,” I told her. She smiled and kissed me. “Please give me your number this time,” I pleaded.
She stood up and I saw her full body again. I saw her tiny cock and her large breasts as she walked toward the dresser. She scribbled something down on a notepad and then tore the sheet off. She handed it to me. It had her number written on it. I smiled and then patted the bed. She lay next to me and we drifted off to sleep in each other’s arms.
Chapter 6
The next morning I said goodbye to Brianna temporarily and rushed back to my hotel room. The guys all looked confused when I walked back in. “Dude! Where have you been?” asked Sam.
“I slept somewhere else last night. I think I’m in love, actually.”
The guys almost looked disappointed. “What are you talking about, bro?” asked Bryce. “We’re all supposed to get laid here, that’s it.”
“You know the flight attendant? Brianna?”
“Yeah, so what?”
“She’s here in the hotel. I just slept with her and it was fucking amazing.”
“The competition’s over, dude,” said Bryce.
“This isn’t about the competition. I can’t stop thinking about her. She’s everything I want. And yes, she’s transsexual.”
Their mouths hung open and their eyes were the size of golf balls. Then they started bursting into a fit of laughter. “What the hell is wrong with you, dude? Please tell me this is a joke?”
“It’s not. She’s really transsexual and I really like her.”
The laughing stopped. “That’s cool, man,” said Rob, trying to redeem the rest of the guys. I glared at Sam and Bryce and they closed their gaping mouths and wiped the smiles off their faces.
“Yeah, whatever,” said Bryce.
“It’s cool,” said Sam.
“Good,” I said. “Because I want to see her as much as I can.” The three of them nodded and gave me their blessing. “And I want to invite her to brunch.”
They agreed and I ran down the hall to Brianna’s room. “Come meet my friends,” I said. “They’ll love you.”
She smiled and wrapped her arms around me. Her warm body pressed up against me and I hugged her in a tight embrace. I felt like the luckiest man alive.
Dressed at the Festival
Chapter 1
The Neon Poppy Festival was a month away and I was flat broke. All of my friends had their tickets already and I was about to buy mine when my car broke down. Since I need my car for work, every cent I saved had to be put towards repairs. Needless to say, I was pretty bummed. We didn’t just go for the music, of course. A huge reason we went was for the hot chicks. Not only were they walking around half naked – often no more than glitter covered their naked breasts – but they were easy too. Not that we went around fucking all of them…but you did get a nice show at the very least.
It wasn’t hard to find a pair or even a trio of girls with their tongues down each other’s throats. If you couldn’t find some, all you had to do was dare them and they would be so wasted that they didn’t even think to turn you down.
I leaned back in my desk chair with my arms behind my head, dreaming about the last festival. The lights, the sick drops, and the half-naked chicks made it the single best event all year. And that’s if you stayed sober. There were always drugs abound if you wanted to make it even more interesting. The only reason I stayed sober most of the time was so that I’d remember all of the crazy events. I had huge databases of sexy women logged into my spank bank from past years. Maybe that’s wrong to say, but I’d never say it to them out loud.
“This sucks,” I said to myself as I browsed the listings. Chicks have this amazing resource to get free shit and oddly enough they never seem to use it. The longer I browsed, the more depressed I became. How was a lanky, 20-something college kid supposed to get a free ticket to the Neon Poppy Festival? I kicked the carpet with the toe of my shoe and folded my arms across my chest.
My phone buzzed on my desk and I saw that it was my best bud, Jason. “Hey bro,” he said. “You get your ticket yet?”
“Nah, man. I’m broke as shit. You couldn’t lend me the money, could you?”
“Sorry, Matt. I spent everything I had on my tickets. I don’t get paid until after. Have you tried Markslist?”
“Yeah. There’s just horny dudes giving away tickets to hot chicks.”
Jason laughed. “Yeah that sounds about right. You could always dress up as a Poppy Chick. You know, get the little tutu and the glitter and everything.” He laughed again and I rolled my eyes. Jason was good at entertaining himself with quirky ideas.
“Yeah right, man. Thanks for nothing,” I teased.
“Alright, alright. I’ll see if I can find anything. Keep your eyes peeled. It’s gonna be crazy!” Jason hung up the phone and I continued browsing.
Despite brushing off Jason’s wild idea, it kept popping into my head. If only I was a hot chick, I thought. I laughed to myself and kept scrolling.
Free NPF ticket…prefer to go with a pretty lady. Out of curiosity, I clicked on the listing. The poster’s name was Nathan and he’d included a photo of himself…and his cock. I rolled my eyes again. These fucking losers, I thought. The last thing a chick wants to see before they meet you is your dick. That means there’s just a ton of extra tickets sitting around that’ll never be used.
My blood started to boil. Why couldn’t they just give a few tickets away to poor guys like me? The angrier I became, the less taboo Jason’s idea seemed. It would serve them right if I dressed up as a chick…
I hopped from my chair and walked to my full length mirror. I was tall, but not too tall. My arms and legs were slender and lanky. My face lacked all the typical masculine angles and my skin was soft and pale. I bet I could pass myself off as a chick. I laughed at the ridiculousness of it, but I hadn’t brushed it off just yet.
It couldn’t hurt to try on an outfit or two… The hamster wheel in my mind was spinning. No one would have to know…
Chapter 2
I frantically thought of a place to find an outfit. I had three brothers, but no sisters and I couldn’t handle the embarrassment of buying ladies’ clothes from a store. I paced my bedroom floor until the only answer available to me revealed itself. My roommate.
Being a college guy, I lived in a house with five other people. One was a girl who was dating my other roommate. They shared a room, making rent cheaper on both of them. And I knew their schedules like the back of my hand. I couldn’t let myself go in there and rummage through her drawers…could I?
I had time to decide. Sam was gone now but Jessica wouldn’t leave for another 30 minutes. Unfortunately, the time flew by and when I heard the front door slam shut I knew it was my only chance. I didn’t even really know what I was looking for. She never went to concerts or anything, so she wouldn’t have any outfits a raver girl would have. But she’d have lingerie. Some of the raver chicks at Neon Poppy made their own outfits by gluing and sewing items to ordinary lingerie.
And besides…I’m going to need to send the guy from Markslist a photo of me. The plan was nearly perfect, I just had to execute it. I exhale and burst through the door. My other roommates were home, so I would still need to move quietly across the hall. I peeked down the hallway for a sign of either of them. I heard one guy yelling at his video game system. The other two were talking in the kitchen around the corner.
The coast is clear…for now. I tiptoed across the hallway to Sam and Jessica’s bedroom. Then I turned the knob slowly so as not to make a sound. When the knob was turned as far as possible, I gently pushed on the bedroom door until it was wide enough for me to slip in. Then I held the knob to the side while I quietly pushed it closed.
Their cat instantly greeted me, meowing and rubbing against my legs. “Not now, Fins,” I whispered. She meowed again and then leapt onto the bed, curling into a ball. I trekked across the carpet to the dresser. As my hands reached the knobs, I froze. I thought I heard Jessica’s voice, but the longer I listened, I realized I misheard.
I slid the drawer out slowly so it didn’t creak. I was greeted with panties of every color and fabric and each with matching bras. Jackpot, I thought. I dug my hands into the waves of silk and lace, and a warm euphoria washed over me. I felt like I’d dipped my entire body into a sun-kissed ocean and was being lulled by its gentle ebb and flow.
I pulled my hands away from the fabric and felt empty and cold. Must be because I’m so attracted to girls, I told myself. Maybe the panties just remind me of getting laid. I dipped my fingers back in and carefully lifted the corners up of each item so that they never left their places. My eyes landed on a deep purple bra and panty set far in the back. I figured if it was in the back, maybe it would go unnoticed.
After all, I thought. I will return it after the festival. I knew that was a long time to keep a pair of stolen panties and a bra, but even if she noticed it missing I could sneak it in one day. She’d just think she was going crazy or something. Great plan. Excellent, excellent plan. I was nodding to myself with a smile on my face and my eyes closed. I was filled with pride that I shouldn’t have been filled with yet, because Jessica was home early, and I could make out her voice talking to a roommate in the kitchen.
Shit! I grabbed the pieces and shoved them in my pants. I flattened them so they wouldn’t leave any odd bulges around my hips. Then I rushed to the door and pulled it open quietly. I peeked around the corner. No sign of her. I closed the door quietly and turned to face my room. That’s when Jessica walked around the corner.
“Oh, hey Matt,” she said, approaching me quickly.
“Hey, Jess.” My throat was tight. My voice was strained. Would she notice that I was up to something?
She walked to her door with a confused expression and then opened it. Everything was in order. She looked back at me and said, “I forgot my wallet.”
I laughed nervously and watched her leave. Then I exhaled a long sigh of relief and entered my room. I closed the door and turned the lock. Then I slid down to the floor with my back against the door and tried to calm myself.
That was too fucking close, I thought. There’s no way in hell I can pull this off. But I had to try. After all, I still hadn’t seen myself in women’s clothes yet. Maybe I could be more convincing than I thought. I knew I could always turn back if the guy from Markslist laughed at me. No one in my immediate circle would have to find out.
I reached into my pants for the stolen treasures. I suddenly realized that my cock was rock hard. I couldn’t tell if it was due to the proximity of the dainty fabric or the thought of almost getting caught with it. I decided it didn’t matter and continued. I pulled the set out and lay them on the carpet. They’re beautiful.
Jessica had average breasts. I’d have to stuff the bra, but not too much. I was grateful in that moment that she didn’t have triple D’s or anything. As I looked at the lingerie, I slid my shirt off. Then I stripped my pants and briefs down, kicking them to the side. I glanced down at my hard cock and stroked it twice. Then I reached for the purple panties.
They were silk and shiny…perfec
t for Neon Poppy. I slid my legs into them and pulled them up to my waist. My cock and balls sit snugly against them and that familiar warmth swept through my body. I moaned and rubbed my cock in the panties. It feels so…damn…good. I kept rubbing as if I’d lost control over my body. I stopped myself in time to keep from cumming inside them.
That would be a disaster, I thought. I can’t wear cum stained panties to Neon Poppy. I reached for the bra next. I slid the straps up my arms and struggled with the clasp. Eventually, I had to turn the bra backwards so I could see the clasp better. Then I moved the hooks to my back and slid my arms back through the straps.
I walked to the mirror and gawked. I was hot! My hairy legs and boy’s haircut were the only things that gave me away. I wasn’t sure whether to be flattered or disturbed. I twirled around and stared at my ass. Then I gave it a little spank.
My cock hardened again. Enough of that, I scolded myself. I wasn’t going to ruin the only pair of panties I had. I thought about how to be more convincing to the online poster. Shaving will be easy, but a wig? I decided to take a body photo only until I could get my hands on a brightly colored, festival wig.
I reluctantly shed the lingerie and got dressed. I rushed to the bathroom and pulled out my razor and shaving cream. I lathered the cream against my legs and ran hot water in the sink. I slid the razor along my shin from ankle to knee. Then I felt the smooth skin with my thumb. Wow. This feels amazing! I couldn’t believe girls complained about shaving. Having smooth legs was the best feeling in the world.
I finished my calves, knees, and thighs and then rushed back to the bedroom. I slid the lingerie back on, careful not to ejaculate. Then I pulled out my cellphone to take a few photos. I posed over and over, trying to keep my hair out of the shot. I took a few photos with my mouth hanging open sexually. I wouldn’t give this guy a blow job or anything, but I wanted him to think I would.