by Jane Futa
“Really?”
“Oh my god!” she cried. “You’re enjoying this a lot, aren’t you?”
I blushed. “I guess I am,” I admitted. Hearing the words come out of my mouth was a surreal feeling. I like dressing in women’s clothing.
“I feel like I’m seeing a whole new side to you,” she said. “It’s…sexy.”
My cock hardened at the sound of her compliment. If dressing as a woman was the only way to get her to notice me, then so be it.
“Okay. Back in front of the camera before I’m tempted to rip all those clothes off of you.” I moved into position, wondering if she’d still like me naked…when it would just be me and my cock. After all I wasn’t a real woman. She couldn’t really be a lesbian with me…
She positioned me a few more times and took a few more pictures. I felt completely naked even though I was fully dressed. I was absolutely a virgin to this. I was a virgin to modeling, I was a virgin to cross-dressing, and I was virgin to the feelings it all gave me.
She looked beautiful behind the camera. Her gaze was focused and deliberate, with a slight smile spreading into the apples of her cheeks. I could feel her eyes lingering on my body. Her irises traveled up and down the length of my legs. She bit her lower lip as if struggling with her anticipation. I wondered what she was anticipating. I wondered if she wanted the same things that I wanted. I wondered if she wanted me the way that I wanted her.
At the end of the shoot, Sasha paused and looked at me inquisitively. “What is it?” I asked.
“It's nothing,” she said. “It's just that you look so damn sexy.” I felt my face flush. I felt my legs tingle. I wanted her and I wanted her to want me.
She walked over to me and leaned in. I felt her sweet breath swirl across my face. Her big, gorgeous eyes stared into me. She reached her hands up for my face, but her fingers landed on my wig. She slowly pulled it off and stepped back.
“Time to change,” she said with her arms crossed over her chest. Her eyes surveyed me and I wondered what she was thinking. I stood up from my seat and followed her back to the shopping bags.
“I’m really excited about this one,” she said. She handed me a pair of skinny jeans and a black bra. Then she pulled out a long, wavy brown wig. “Go on. Get undressed.”
I stripped in front of her again, but this time with more confidence. I had more than enough proof that Sasha found me attractive, if only when I was dressed as a woman. I didn’t care. I’d take her affection in any way that I could.
I slid off the skirt and tank top until I was only in my panties again. I felt a little more naked due to not having a girly wig on my head, but that was about to change. I took the jeans from her and stepped inside. They were so tight and constricting as I slid them up to my waist. I couldn’t believe girls actually wore clothes that were so fitted to the curves of their bodies.
I felt hyper aware of myself in those jeans. I felt every shift of my muscles and every curve of my body. Despite its restrictive nature, I felt sexy. I just hoped Sasha thought I was sexy as well.
She handed me the bra and I slid it on. She walked behind me to fasten it. I felt her knuckles graze along the skin of my back. Her touch sent a wave of warmth through my waist. I felt my cock harden again, but this time it had nowhere to go.
Sasha reached for the long, brown wig and placed it on my head. “Let’s do something different with your makeup,” she said. I sat on the couch and waited for her to bring out the items. She wiped my face with a makeup removing cloth and started on her new masterpiece.
When she was finished she showed me my reflection in a compact mirror. It was a more natural look, and surprisingly still quite feminine.
“I thought you might be able to pull it off,” she said with a wink.
“Pull what off?”
“Your natural face…it’s feminine enough to pass as a girl without a ton of makeup. You have very pretty cheekbones.” She smiled and my stomach fluttered. “Come on. Time to do the final shoot.”
I took my place in front of the camera and Sasha directed me for the last time. As the camera clicked again and again, I couldn’t help but wonder what would happen to us when the shoot had ended. What would happen to me? Would I continue experimenting with being a woman?
“That’s it. Thank you so much,” she said through a curtain of hair on a bowed head. She lifted it up to look at me. She looked as sad as I felt. I think we were both confused about what the other one wanted. It was a strange experience overall.
She walked toward me and reached for the wig again. I grabbed her wrists to stop her. If I was ever going to make a move, now was the time. Dressing in girl clothes somehow brought me a sense of confidence I didn’t have before. I felt comfortable in my body for the first time in my life. I felt comfortable leaning in to kiss Sasha.
“If you don’t mind,” I said, staring into her heated gaze, “I’d like to wear it a little longer.”
She exhaled and I saw my moment. I leaned my face in, closed my eyes, and puckered my lips. I kept pushing in blindly until they hit skin. Her lips were warm and soft. She didn’t pull away. The longer our mouths touched, the faster my heart beat until it gradually fell into a slow rhythm. It was a confident rhythm – a comfortable rhythm.
I felt her lower jaw open. Her hands wrapped around my neck. I instinctively wrapped my arms around her waist, pulling her into me. Her tongue slid into my mouth and circled my tongue. Her saliva was sweet and heavenly. Everything was better than I’d ever dreamed it to be.
Her hands were warm against my hips. She dug her fingernails into the skin. Her teeth found my lower lip and bit down, nearly breaking the skin. I was enveloped in the floral scent of her perfume and her cheeks smelled like warm sunlight. I’d never wanted to be anywhere more. I’d never wanted to kiss anyone more.
She pulled away abruptly and her eyes canned my face. She kept her nails digging into my hips and my arms stayed locked around her.
“What is it?” I asked.
“It’s just…” She unfolded her hands and I dropped my arms to the side. She stepped back a few feet and looked to the floor. She was nervous as if she had a confession.
“You can tell me,” I said, desperate not to lose her affection.
“I have a sort of…fantasy,” she said, “that I haven’t been able to live out yet.”
“What is it?” In that moment I would’ve given her anything her heart desired. Fantasies were hot, anyway. Whatever hers was I was sure would be exciting.
“Well,” she started, looking up at me with a painful expression. “It really turns me on to see you dressed as a woman, but I like to play a little rough. The other guys don’t really like it that much.”
“I’ve got a pretty open mind,” I said, thinking about what rough ways she enjoyed being pounded. I was surprised that the alpha men that she’d been with previously didn’t want to play rough with her. She was hot. Who wouldn’t want to pound her tight little pussy?
“Well. If it gets to be too much for you, let me know.”
“Alright,” I said, suddenly doubting my previous assumptions. It sounded as if I was the one getting the rough treatment. But I didn’t want to lose her, not now. I’d never been this close to Sasha and I desperately wanted to get even closer.
She walked up to me with a smile on her face and then reached her hand up for my throat. She gripped it tightly, but gently. “Drop to your knees,” she said in a low, commanding voice. Despite the strange twist of events, my cock hardened at the sound of her barking an order. I nodded and then lowered to the ground. Her hand lowered with me.
“Good girl,” she said. She released her grip on my neck and then disappeared into the bedroom. She came back out with a double-ended dildo wiggling as she walked. “I’ve got a present for you, for being so good.”
Oh my god. What is she planning on doing with that thing? I wanted to please her but I wasn’t sure if I was ready to handle such a long cock. I’d only just gotten used to
the idea of wearing women’s clothing. She strutted back toward me and smiled underneath a curtain of blonde hair.
She placed her thumb on my chin and tugged it down so that my mouth hung open. “Stick out that sexy tongue of yours,” she said. I slid it out along my bottom lip, feeling the cool air of her apartment rush in against the roof of my mouth.
“I want you to suck on this big cock. I want you to take in as much as you can fit. Don’t hold back unless you think you’re going to vomit. I want to watch it slide down that pretty throat of yours.”
I nodded, my cock stiffening with each new word that escaped her mouth. Was this really turning me on? She rested the head of the dildo against my tongue. I wrapped my lips around the tip. Sasha bit her lower lip and tilted her head to the side as she slid it further in.
“Ohhh,” she moaned as she watched me take it in. Her free hand ran along her breasts. Her hips swayed. I’d never seen turned on at all before. I would’ve swallowed the entire thing just to see more.
I closed my eyes and took in inch after inch. I felt the tip of the cock at the back of my throat, and still I took in more. Suddenly, I heard a click sound. My eyes snapped open.
The studio lights were still on. They were blindingly bright. I heard another click and the cock slid further in. When my eyes had finally adjusted, I saw Sasha’s free hand now leaning back toward her camera. She was photographing me!
I felt so vulnerable and so exposed, but it only turned me on more. “That’s it,” she cooed, her hips still swaying. She was incredibly good at multitasking. I wanted to protest, if only for the privacy of my photos, but I was too busy swallowing a giant cock. I couldn’t even move my jaw.
She moved her hand away from the camera and kneeled down in front of me. She continued to slide the cock in and out of my mouth while unfastening my jeans. She slid them down to my knees and reached her hand into my panties. She smiled when her fingers wrapped around my stiff cock.
“Someone likes this, don’t they?” she asked. I nodded, my mouth still full of cock. She began to stroke me as I sucked on the dildo. I moaned through my sucking and she seemed pleased. “That’s it, baby. Mmm, just like that.”
She alternated between fondling my balls and stroking my cock. I continued to suck and gag on the dildo in my mouth. It was sliding slowly down my throat and I felt my throat stretching to accommodate it.
Suddenly I felt her mouth on my cock. Her lips were wrapped around the tip. I looked down and watched the love of my life suck my dick. Her head bobbed up and down. Her beautiful blond hair fell around my pelvis.
I reached up for her head and wove my fingers into her blonde locks. She moaned through her sucking and I moaned too. As much as I enjoyed watching her, the pleasure was just too great. I had to close my eyes.
My body grew hot and tense. I knew I was about to blow, but I couldn’t warn her. My mouth was practically gagged. I felt my cock throb against her tongue and then explode. My hot come shot toward the back of her throat.
She swallowed every single drop. She was a cock sucking expert. Not that I’d had many blowjobs.
She pulled her tight little mouth off of me and looked up with big doe eyes. She looked so sweet, so innocent, and yet she was shoving a double ended dildo down my throat. She slid it in and out a few more times before giving my jaw a break. She pulled the whole thing out and then sucked on it too.
I knew she was attractive, but I had no idea how wild she was until now. I had no idea she was ever even hiding such a long sex toy in her bedroom. I wanted more. I wanted her to do whatever she wanted to me. I was about to get my wish.
She leaned me back on the floor with my pants still around my knees. I watched her eye me hungrily and lick her lips. She slowly climbed over me, kissing her way from my cock to my neck. Then she kissed my lips, sliding her tongue all around me.
My breathing was heavy and gasping. My chest lifted off the floor to get enough oxygen between kisses. She wasn’t the only person that was hungry.
She climbed above me further, until she was standing, one foot on either side of my head. My eyes traveled up the length of her bare legs and peeked underneath her jean skirt. She had on soft, white panties and they were soaking wet.
She reached her hands up under her skirt, lifting it around her hips. Her fingers hooked around the band of her panties and she slid them down over her ass. As they lowered to her knees, I saw a wet string of her lubricant connecting her beautiful pussy to her panties. She lifted one leg at a time, sliding them out of the white cotton. Then she tossed them to the side.
I had the perfect view of her bare pussy. It was tight and clean. Her small folds flipped outward, revealing just how swollen and turned on she was. She lowered to her knees and dropped her skirt. Suddenly I couldn’t see a thing. I could only smell the sweet scent of her pussy. She continued to lower until her folds rested against my lips.
I stuck out my tongue eagerly and began to lick. She moaned as I flicked my tongue along her beautiful folds. I heard the camera clicking over and over. I didn’t even care. I was getting to taste my best friend’s pussy. The friend I had yearned after for so long. It was like a dream come true.
She rocked her hips slowly over me. I quickly learned which spots and motions pleased her. I listened intently to every moan and whimper. I took note when her thighs quivered around me. I slid my tongue inside of her little pussy and felt just how tight it was. I couldn’t believe I could feel the walls surrounding my tongue. She was too perfect. I only loved her more and more as time went on.
She rotated her hips and the clicking of the camera stopped. She was concentrated on coming. She moaned over and over again until her body started shaking violently. She let out a wild scream and came on my face. I lapped up every last drop of her sweet pool.
She climbed off me and lowered her body toward my pelvis. She smiled at my rock hard cock. She placed her mouth around it again, sliding it up and down a few more times. Then she sat up and stripped her red tank top from her body. I saw her breasts for the first time, covered only by a sheer white bra.
She reached around and unhooked it, sliding it down her arms. She tossed it to the side and stood up to remove her skirt. She was completely naked now. She straddled my hips and lowered her pussy over my small cock. She seemed eager for it. She seemed excited to fuck a chick with a dick.
She slid it all the way in until her clit was grinding against my pelvis. She rocked her hips back and forth. Then she lifted her hips up only to slam them back down. She alternated between these two positions until she was ready to come again.
I recognized the quivering of her body as she neared orgasm. She looked me straight in the eye and said, “You’re the best lay I’ve had. I love a good little trans girl.”
My heart pounded in my chest. Even though she was fucking my cock, the thought of being her little girl turned me on. The longer I thought about it the more my cock throbbed. She ground her hips into my pelvis until we were both screaming, coming simultaneously.
She collapsed against me as we caught our breath. I stroked her hair, unable to believe I’d just fucked the love of my life while dressed like a woman.
“That was amazing,” she told me. “ But there’s something else I’ve been dying to try.”
She reached for the dildo and dragged it along my cheek. “I want to fuck your virgin asshole with this,” she said. She read my shocked expression. “Don’t worry. I’ll be gentle.”
I bit my lower lip in hesitation and nodded. She lifted her hips off of me and rolled me onto my stomach. I heard the camera click a few more times and I turned my head to face it. “Good girl,” she said with a smile.
She grabbed my ass cheeks and spread them wide. Then she spit between them. I felt her run a finger along the crack, sliding her spit all around my skin. The camera clicked again.
She spit again and continued rubbing. She slid a finger in. Click. She slid a second one in. Click. By the time she’d worked three fingers in
I felt completely full. I knew that dildo would be much thicker than three of her tiny fingers.
I heard her suck on one end of the dildo. She removed her fingers and spit one more time. Then I felt the head of the dildo rest against my hole. Oh my god. Here we go, I thought.
She pushed in and I felt my tight little asshole stretch around the cock. “Fuck!” I cried in temporary pain.
“Shhh,” she said. “It’s ok. The more you relax the better you’ll feel.” I tried to relax but it still hurt. She pushed in further. As it slid in deeper, the pain subsided and turned to pleasure. Insane pleasure. I couldn’t believe how good it felt. Eventually she pushed in as far as she could go.
“How do you like that, baby?”
“It feels so good,” I said in a long exhale. She smiled and started to pull it back out slowly. It felt even better as she pulled out. I let her slide it in and out of me for a few minutes. I heard the camera click a few more times.
“It looks so good inside of you,” she said. I smiled. I wanted to look good for her. I wanted her to enjoy herself.
I felt her shift around and I peeked over my shoulder at her. She was straddling my ass, her pussy hovering over the other end of the dildo. I watched her place the head of it along her slit. She dragged it through the folds of her pussy, only stopping to slap it against her clit. She leaned her head back and moaned. Her blonde hair fell delicately down the length of her back. Her neck was exposed and vulnerable.
She slid the tip of the dildo inside of her tight pussy. I watched her cunt stretch around it. I thought of when my ass stretched around the opposite end. I imagined that I had a pussy instead, like Sasha. It felt incredible. It was as if I was meant to be a girl all along.
The dildo slid further inside Sasha’s pussy. “Ohhh,” she cried as it filled every inch of her. She managed to fit it almost completely in. Then she clicked the camera again.
Using her pussy to clench it, she began fucking my asshole with the shared dildo. She raised her hips, pulling the cock with her. It slid slowly out of my ass until she stopped. She pushed her hips down and it slid back in. I felt my cock harden and throb. She was fucking me like I was a little slut.