Practice Sessions

This is a fantasy story about two 18 year old friends, one of whom discovering a trans side they never knew existed.

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Frank could always talk me into anything. We were both nerdy seniors in high school, a couple of months past our 18th birthdays, with no experience with girls, and no way that we could figure out on how to get it. "Look, I am telling you, girls practice kissing with other girls," he told me, again...

"So you want to practice kissing with me, while I am wearing this...," I asked, holding up one of his sister's old dresses. It was insane, but the way he looked at me and just shrugged kind of killed my arguments against it. I mean, there was no way he was going to fit in it, he was a good 4 inches taller than me, and bigger and stronger, and I was about his sister's size.

Like every other crazy idea he could talk me into, he just waited on my resistance to wear out and to give in to his plan. I knew I was going to do it, I always did, so I just shrugged and took my shirt off, slipping the dress over my head. "Looks stupid with jeans on," he commented, as if it did not look stupid no matter if they were on or off, but I just sighed and pulled my jeans off. "Really, socks," he then commented, so those came off too.

I was struggling to zip up the dress, so he stepped behind me and helped with the zipper, letting me get a view of the two of us in his mirror. I didn't see myself, I mean I knew it was me, but I saw this girl version of me standing there in a dress and this far more masculine guy behind me, with his hands on me. "It fits," he commented, "and you look kind of hot in it."

That made me blush a little, but it was true, I did look kind of hot. I moved a bit and the skirt on the dress flared out, the look of it in the mirror adding to the effect it was having on me. He was right behind me, a good head taller, bigger, making me feel even more girly. He was also... cute? How did that thought pop in my head? I blushed at the thought of it.

His hands had moved down from the zipper to my hips, and I could feel his body heat against my back. I moved my hands to my hips, covering his, and our fingers just interlaced, and suddenly we were holding hands. I was watching us and it felt like I was someone else there in the mirror, a girl, definitely a girl, waiting for her man to kiss her. Needing her man to kiss her. I turned around and looked into his eyes, my arms moving up to drape over his shoulders. I could feel his hands moving, one moving up towards my neck and the other coming to rest on my ass. We leaned into each other, my head slightly tilting to the side as I closed my eyes and felt his lips against mine. It was a perfect first kiss. Gentle, sweet, nothing too forceful, but he was definitely taking control, cupping my head in one hand and my ass in the other. We broke our lips apart and we both looked at each other, looking to make sure that things were OK, and then he pulled me even tighter to him and we were kissing again. I opened my mouth and he followed suit, then I could feel his tongue snake past my lips and all of a sudden our tongues were dancing with each other in my mouth. The hand on my ass was kneading my cheeks and it felt so good. I lifted a leg and wrapped it around him, giving him more access.

I didn't want it to stop, but it was a bit awkward standing there, holding on to each other. My arms were around his neck, and I had one leg wrapped around him, so I just kind of hopped a bit and wrapped both legs around him, letting him support both of our weights. His other hand dropped to my ass, joining the first and holding me up, our lips never separating for more than a moment. I could feel him moving, then I felt myself getting lowered to his bed, getting laid on my back with him on top of me. My legs were still spread wide from holding on to him, and I could feel his hardening cock rubbing against me. I knew I was not large by any means, but what he was rubbing against me felt so much bigger. I started to moan as he continued to rub himself against me, and as I turned my head I felt his lips on my neck, kissing me there. I could hear myself whimper, and all of a sudden I shuddered, my own little cock cumming in my underwear, never having been touched. I had to catch my breath, and we continued to kiss for a bit more before he rolled himself off me. We didn't say anything lying next to each other, I guess each of us processing what happened. Eventually I got up and grabbed my clothes and went to his bathroom and changed back, cleaning myself up in the process. I had cum so much it had leaked out and gotten on the dress, so I tossed it with my stuff and left without saying anything else.

I was on my way home when his text arrived, "U OK?" I replied with a thumb up. "Can we talk," came the reply.

"L8R," I texted back, and kept driving. I got to the empty house with my folks gone for a few days, so I quickly tossed the dress and some of my clothes in the laundry and went to my room. What happened, I asked myself. OK, I knew what 'happened,' but it was like it wasn't me. I was looking at myself in my mirror, and I was looking at a different person. And that person looked less natural to me than the one I saw in the mirror at his place. I knew my mom had a bunch of old clothes that were supposed to get donated, so I went into the garage and opened the box, pulling out a cute dress and a couple other things. I went back to my room and looked at myself in the mirror, and then stripped and put on the dress. Looking back in the mirror, that was me there. The dress was more me than my other clothes. I spun around in it and loved how it flared out, I liked the look of my legs, I flipped my hair with the back of my hand, I imitated every girly gesture I could think of and each time, it was more and more like that was the real me.

I knew my folks would not be home for the rest of the weekend, so I flipped the laundry over and started to rummage more into the boxes, still wearing the dress. I found a few more things I thought were cute, along with a pair of heels and a few nightgowns, not old lady style, but just kind of simple. I grabbed my expanding cache of clothes and brought them back to my room, trying everything on before finding a good hiding spot. I then decided to check out my parent's room, and rummaged in my mom's laundry, finding a bra and panty set that didn't look too used and some pantyhose. I knew better than to steal any of her clean stuff, so I grabbed it and went back to my room, trying it on with a dress. I grabbed a few socks to stuff the bra and after figuring out how to put the pantyhose on, I slipped the heels on and looked at myself. Everything I did just made me feel more and more like it was the real me. I popped on my computer and googled make-up tutorials, and in a flash I was in the bathroom trying on lipstick and eyeliner. I started to brush out my hair a little different and slicked it back, and there I was,a full on girl. I liked what I saw.

I went to the living room all dressed, walking carefully in the heels. I flicked on the TV, and saw a new rom-com in the Netflix queue. Normally, I would be putting on a superhero movie, but I was drawn to the other one, and really got into it. I loved seeing the clothes, and when the 3rd act came up and the leads were finally a couple, watching them together brought back all those feelings from kissing Frank. I went back to my room and saw my phone had kind of blown up from messages from him. "R U OK?, Call me, I'm sorry,I'm a jerk..." I was still feeling all giddy from the sappy romantic ending of the movie so I texted back

"All is good." Then I quickly added "come by 2tmrw" and added a blowing kiss emoji then turned the phone to silent so I could get in the last word. I changed out of the dress and slipped on the nightgown, and went to sleep. Well, it took a while with the feeling of the nightie against my skin, but I did eventually.

In the morning I rummaged through the clothing and found a pair of pink shorts and a tank top and went to make myself a little breakfast. I took a pair of fuzzy pink slippers and made myself a simple bite. I needed make-up, some more clothes.... There were things I wanted to wear, but couldn't steal from my mom. Target popped in my head, so I headed back upstairs and put on a pair of jeans and a t-shirt and headed to the store. I grabbed a basket and walked by the women's section, looking around. No one was there, it was early I guess, so I walked over to the underwear rack. No alarm bells rang out, no one yelled at me, so I grabbed a pack of panties off the rack. There was another area with some sexier looking things, and no one was saying anything yet, so I walked over and saw a very cute baby doll set with matching panties and a few lacier bra and panty sets. It is Target, so there was a limit on how sexy it was going to be, but it was good enough... I saw some leggings, so I grabbed a pair and then saw some stockings that looked so sexy. Into the basket they went. Next I went to the make-up area and quickly grabbed some mascara, pink lipstick and gloss. I saw some nail polish in a similar shade and tossed that in as well. I found some floral shampoo and grabbed some hair removal cream, some moisturizer and perfume, then headed toward the registers (thank god for self check-out). I saw some accessories along the way and grabbed a few for my hair and then saw some pink fashion glasses, clear lenses, and tossed those in as well. I paid for everything and headed out to the car, no one chasing me down or yelling that I was a pervert, no one even giving me a second glance.

Hurrying back home I spilled out my haul on my bed. First things first, I decided to shower. I was never very hairy, but I thought that a girl should be smooth, so I trimmed the hair as best I could and then used the hair remover, even under my arms and all around my little but rock hard cock. Next came the wardrobe, so I slipped on a pair of lacy panties, high cut and a matching bra. I looked at myself in the mirror and loved what I saw. Well, almost. I wasn't big down there, I measured it at 4 inches one time, but it was still kind of bulging. I played with it and smoothed it out, but couldn't get the look I wanted. Finally, I went to the internet and just typed 'how to hide bulge in panties.' Internet to the rescue. I really wasn't sure about tucking away my balls, but I decided to give it a go. A few minutes later I figured out where they were supposed to go and,pop, in they went. It felt a bit odd, but I smoothed myself back down and looked at my very girly crotch in the mirror. I had the nail polish, so I looked for a tutorial and on it went. It didn't look great, especially when I used my left to do my right, but eventually I got my fingernails and toenails done. I felt very feminine blowing on my nails to get them to dry as I stared at myself in a bra and panties. I looked at the string of texts from Frank and decided to ignore all but the last one, asking how I was, so I replied for him to come over in 2 hours. This time I left off the kiss emoji.

Next I worked on my make-up, keeping it simple, just the mascara and lipstick. I really wanted it to look perfect, so I put the lipstick on and took it off a few times to get just the look I wanted. A little lip gloss on top and I had a very sexy pair of lips that definitely needed a big strong man to kiss them. God I hope he isn't freaked out. I sprayed on the floral perfume and then added the thigh high stockings to the look. Slipping the heels on over them I was almost tempted to wait for him looking just like this, but no, I smiled to myself that he only would get to see all this if he was good. Well, bad. Well bad in a good way. I put on a plaid skirt, not a quite a schoolgirl uniform, but close enough, and added a pink tank top that just left my midsection exposed with spaghetti straps. I slicked my hair back and put a little flower clip in it and put on the pink glasses to complete the look.

I was lost looking at myself in the mirror when I heard his car pull into the driveway. I texted that the door was open so he could let himself in. I looked myself over one last time and saw a cute, no, very cute, girl there staring back at me. I decided to sit on the bed and crossed my legs, seeing just a hint of the stocking top leaking out. I heard the door open and close and he called out to see where I was in the house. He headed toward my room and was saying that he was sorry for yesterday, that he pushed things too far, that he was a jerk. My door opened and he stopped dead in his tracks, his mouth hanging open for a moment before he shut it, not saying a word. I held out my arms in a way that signaled I wanted him to help me stand, and I told him that I thought maybe he wanted a little more practice.

He walked over to me and took my hands helping me stand up. With the heels on, I was only a half-head shorter, making us a bit more even. He was about to say something when I pressed a finger to his lips. "Shhhh. Do you want to talk, or do you want to practice?" I don't know where all this confidence came from, because it felt like I was shaking on the inside, but he closed the distance and took me in his arms and all of a sudden we were making out hot and heavy. Where he was tentative yesterday, he was aggressive today, grabbing my ass from the start and pushing his tongue past my lips. I had my eyes closed and my arms wrapped around his neck, sucking on his invading tongue and swirling mine around it. I could feel the heat of his hands as one cupped my back under my top and the other snaking under my skirt and kneading my ass. A finger traced the crack of my ass, I don't know if he meant to do it or not, but that got me to break the kiss and bury my head in his shoulder, moaning loudly as my body reacted to the intimate touch. He boldly slid the finger under my panties and fingered me again, bruising against the opening. That had me whimpering and shaking, almost cumming right there as I stood.

My knees went weak on me and slumped to the floor, my arms still around him and now my face level with his crotch. I could see the outline of his cock in his jeans, straining at the denim. It looked so big and masculine, and my hands went to it, rubbing it though the material. I loved looking at my small hands, with my painted nails, tracing the outline of his hard cock. I went into the day thinking of nothing more than a make-out session, but I suddenly needed to see his cock, to touch it, and even more. I opened his jeans and pulled them down leaving him standing there with his cock tenting his boxer briefs. I looked up at him as my hands rubbed his cock through the cotton, licking my lips. "Did I do this," I asked. I moved closer, taking in his musk and rubbing his cotton covered cock against my cheek. I took both hands and traced the outline of it, and then slowly drew his shorts down to join his jeans on the floor. His cock sprang into view, rock hard and looking so much bigger than what I had. I pushed that thought out of my head, not wanting to think about my body, but instead focusing all my attention on his.

It felt so warm in my hands, thick and long, rock hard but also smooth. I wrapped a hand around it and started to jack it slowly, feeling the skin move with my hand and glide over the head. I knew exactly what it felt like from the other side of things, but this was so much more fun for me. I loved the feel of it in my hands, and when I was able to get a drop of precum to form on the tip, I licked it up without a hesitation. One lick became two, then three, then I was swirling my tongue over the entire head, and finally I just parted my lips and took him in my mouth, the head of his cock just getting past my lips as he groaned and started to cum in my mouth. I never stopped sucking or licking the head, taking his full load and swallowing it down. I kept sucking and licking, taking whatever he had to offer. Finally he stopped shaking a bit and I pulled my lips away, still on my knees, looking up at him and kissing the shaft and playing with his balls. I reached out my hand again for him to take it and help me up, and he surprised me by moving in for another kiss. Not that I minded. We started making out again, hot and heavy, with his pants still down around his ankles and me gently stroking his cock. Being a teenage boy, it didn't take long for it to get hard again.

I was really enjoying the feeling of his cock filling up, thickening and lengthening in my hands as we kissed. I felt like I had this power over him, but also that I was so small and feminine and under his control. I wanted to feel it inside me, but not quite yet. He was stronger and bigger, but he also still had his pants down around his ankles, so I was able to push him onto my bed pretty easily. He landed with a slight thud on his backside, his now fully hard cock sticking up in the air like a flagpole. I looked at it, licking my lips, thinking of giving him a second blowjob, but instead blew him a kiss and said I was hungry for food. I turned away from him and started walking out of the room, swinging my hips as I did. I wandered to the kitchen and put on a pot of water so I could make some pasta. I heard him come downstairs so I made sure to bend at the waist and make my ass the first thing he saw as I rummaged in the fridge. I heard his footsteps on the tile then they just stopped. I moved a bit so I could see over my shoulder and he was just staring there, slack jawed, ogling my ass, that same blank lusty and shocked stare he gave me when he first came over. I walked over to him and gave him a quick peck on the lips and went back to making some dinner. I had always helped in the kitchen, but dressed like this, wearing heels, with my - I didn't know what he was yet, lover, boyfriend, FWB? - there made me feel so feminine.

He started to talk and I just put my finger to his lips to quiet him and kissed him on the cheek. 'Later," was all I said. I went about making the pasta for us, really just ravioli and jarred sauce, and set the plates so we were next to each other at the table. "Look," I started, "I don't know where this is going to go, I don't even want to think about the end of the weekend right now, but when I put on that dress last night, for the first time in my life I felt like... me. I like that feeling. I like being this me."

"So, does that make us, gay", he asked, something I had thought a bit about myself.

"I don't feel gay. I feel like a girl who is with a guy. Her straight guy. A straight guy who likes me as a girl. I had never looked at a guy before and thought he was cute, or sexy, or that I wanted to... do things to him." That last line definitely got him to blush, which I found so damn cute and sexy. So cute and sexy that I had an uncontrollable urge to kiss him, so I just went with it, and just like that, we were making out again.

I don't even know how we got there, but eventually we were on the sofa, his body on top of mine, my legs wrapped around his hips. I could feel his growing manhood pressing against me and his hips slowly dry humping me as we continued to make out, his tongue exploring every corner of my mouth. He moved to start nibbling on my neck and I began to moan, feeling the blood rushing to my own growing organ. As much as I was enjoying myself, I wanted to make the night last longer, so I pushed him off me. Well, I wasn't strong enough to do that (which just reinforced my girlishness), but I did push him far enough away that he got the hint. I squirmed out from under him and told him to pick a movie on Netflix while I went into the kitchen to make popcorn.

I came back out with the popcorn and saw he had selected a horror movie I settled in next to him, leaning against him with my legs tucked in underneath me, sharing the bowl of popcorn as the movie played. He had his arm around me absentmindedly stroking my hip, but I am pretty sure he had seen the movie before because he perfectly timed poking me with the first big jump scare of the movie, Of course that made me leap, which got him to laugh, and me to throw popcorn at him, and then we were making out again, the movie forgotten, and our bodies right back to where the were before, me on my back with my legs wrapped around his waist and him slowly grinding his hips against me. I grabbed the remote and turned the TV off and told him maybe we should head off to bed. I don't think he was planning on spending the night, but it was common enough for us to spend the night at each other's place, so I knew it wouldn't be an issue for his parents.