Meeting Alice For the First Time [T(mtf)/T(mtf)] [xpost from /r/transstoriesgonewild] | 2016

During my years in college, I was fortunate enough to go to an art school that was in the heart of a major northern east coast metropolis. This meant that I had a lot of company when it came to the trans and trans-admirer community and an abundance of resources like trans-friendly shops, clubs and bars, even an entire queer-friendly neighborhood at my disposal. I had a decent amount of practice in the art of “trans-passing”, but wasn’t anywhere near where I am now. For a short primer and more details about how I identify myself as far as my orientation and gender identity, check out my last post in /r/transstoriesgonewild here. At the time, I think I still considered myself a “part-time cross-dresser” in private only because I didn’t feel comfortable enough going out in public in girl mode, but I frequently wore panties, thongs, and stockings under my clothes on days that I was feeling especially feminine. The other thing I did regularly was flirt with guys online on chat sites and forums. I wouldn’t necessarily say I was “posing” as a girl since I felt that would belittle myself and others who identify as one, but I wasn’t exactly identifying myself as a trans-girl. Something about typing that letter “F” between my age and location when I introduced myself was exhilarating though, and I knew that guys were talking to me assuming that I didn’t have a penis. That was primarily for the purpose of roleplaying sexual encounters online just to get myself off, but I also browsed trans-support forums and identified myself as a trans person there. That’s how I met Alice.

Alice was a trans-girl a couple years older than I was. She was like me in a lot of ways when it came to how she enjoyed sex and who she enjoyed it with, but unlike me she lived publicly as a girl full time in day to day life, including going out for even the most mundane of errands, which was something that I definitely aspired to. As it happened, Alice lived in my city, and after a long time chatting online and developing a friendship, we agreed to meet up in person and see what would happen.

I packed up a few of my favorite outfits and some jewelry and makeup and got on the subway to Alice’s neighborhood. As I was approaching her address I noticed the most beautiful girl I had ever seen sitting on a front stoop smoking a cigarette. It’s important to note that at this point I hadn’t seen what Alice looked like from the neck down before, and she hadn’t seen me. Both of our profiles on the site we had been chatting on used just head shots for the avatars. Now, I knew that Alice was beautiful from that head shot, but good god, her body was stunning. She was about 5’7”, thin, but with some firm thickness to her legs, and her skin was this milky white that was just incredibly entrancing. And her fashion sense seemed to be exactly the punk princess look that I had pictured. She had black hair with one side of her head shaved, an eyebrow ring, heavily applied dark makeup (my weakness) with fire engine red lipstick, a permanent snarl, and a spark in her eyes that seemed both disinterested and hungry all at once. She was like a predator surveying her territory waiting for prey to cross her gaze. She was wearing a black tee shirt with the sleeves ripped off and a band name and logo I didn’t recognize printed in white on the front, a blue and black tartan plaid skirt, black stockings with obviously intentional rips and runs all over them, and lace up shitkickers that stopped about an inch below her knees. Her hair was jet-black and styled in a sort of spiky bob, wild and messy with barrettes and hairpins keeping it that way. I approached her cautiously.

“Alice?” I inquired.

“Hey,” she answered, “you must be Tony.”

“I am, nice to finally meet you.

“Likewise,” she said as she looked me up and down. I was wearing way too tight skinny jeans, a purple tee shirt under a black hoodie and my trusty black and white checkered Chuck Taylors. My hair was a bit long and could be easily shaped into a feminine style. “Wanna come up then?”

“Yeah, definitely!”

We walked up three flights of stairs to her apartment and she let me in. She gave me a quick tour and offered me a beer. I took it and she sat down on her sofa and instructed me to do the same. As we killed a six pack together over the next couple hours we shared stories of our sexual histories and compared skateboarding scars and injuries. We talked about our families and friends and music and food and pretty much anything we could think of. We were listening to music when her roommate came home and introduced himself. He said he had some studying to do and asked if we could turn it down, so Alice grabbed a set of headphones and we shared them. Of course, this meant we had to sit right next to each other on the sofa. It was weird, for all my sexual experience, I was incredibly nervous. I had never been in the presence of someone so confident and comfortable in their transsexuality. I was a more than a little jealous and totally infatuated and just falling all over myself for this girl. It was like Lydia from Beetlejuice was in a roller derby league and as far as I could tell she was into me.

I glanced at her at caught her glancing at me. I turned on the couch and looked straight into her eyes. She leaned forward, closed her eyes and gave me as gentle a kiss as I could imagine. My heart was pounding in my chest and I thought it would leap out of my throat when she put her hand against my face and held me there, giving me no choice but to kiss her back. With our eyes closed we sat there and kissed each other while at least two songs played in the headphones. At some point the music stopped and I didn’t even notice. I knew hooking up would be a possibility when I made the plans to meet up, but being there and experiencing Alice in person was a completely different experience from what I thought it would be. It was like she had this aura that just threw me for a loop and put me off my guard. None of my “smooth” make out moves were coming to me. All I could do was follow her lead.

Alice put her hand on my leg just on the inside of my thigh and slid it up to my crotch. To say I had a bulge would be silly since I was wearing impossibly tight skinny jeans, but they were becoming less and less comfortable by the second. She grabbed my junk and cupped it tightly and whispered into my ear in a sexy breathy voice “I want to taste you.” Without hesitating, I stood up and undid my belt. She yanked down my pants and pulled my three quarter chubbed dick over the waistband of the panties (orange with pink polka dots) I wore under my skinny jeans. Alice wasted no time fitting it in her mouth and getting me fully erect. She was going deep on every pump and my hands found their place on her head. I wasn’t pushing or anything, just feeling the movement and enjoying it.

She stood up and kissed me again and then I looked her in the eye and asked “Can…can I um, do you?” I honestly wasn’t sure how she’d answer (assuming she knew what I meant), since we hadn’t really gone into a lot of detail concerning her comfort with utilizing her boy parts during sex. She lived full time in what I call “girl mode” when I do it, but she always identified strongly as a trans-girl and referenced her dick being there, not ignoring it or wishing it wasn’t there or anything as far as I could tell, so I was hopeful. She nodded in the affirmative and sat back down on the couch. I knelt in front of her and rubbed my hands all over her stockinged legs, starting at her ankles and ending as far up on her thighs as the stockings went. I love the feel of that material on my own skin and feeling it on someone who I desperately wanted to fuck was just as good. My hands crept under her skirt to pull down her panties and found a black lace thong with little red bows on the front and back which I slid to her ankles. She kicked them off as my thoughts were torn between wanting to get my lips around that cock of hers and the idea that she might let me try these panties on when we were done. I initiated more kissing with her again, and when I started massaging her semi-erect penis with my hand she inhaled sharply and gripped my shoulder tightly, digging in her nails. I teased her asshole with one finger and started stroking her stiffening cock.

I flipped up her skirt and got my first look at her. It was a beautiful cock. Smooth, uncircumcised, and I swear, she must have used moisturizer on it because it felt like silk in my hands. The head was the same thickness as the shaft (I really don’t like disproportionately bulbous cock heads for some reason), which was about average, slightly less thick than mine. It reached up about six solid inches and seemed to beckon me. But before I could start giving her oral, I just had to play with the ample amount of precum that was trailing out of her cock. I rubbed it around and coated the head. I tasted it and gave some to Alice to taste. Feeling the slickness and gliding my fingertips around on it just drives me nuts and there’s something about an uncut cock that seems to generate a lot more of it. It’s one my favorite things about playing with dicks, be it my own or someone else’s.

I could tell Alice was aching to feel my mouth on her, so I got a nice helping of the crystal clear nectar on my finger and got a final taste. I then held her cock back against her stomach and gave it a lick from root to to tip and then closed my mouth around it. I swirled my tongue and sucked my cheeks in and out and gave what I think might have been one of the best blow jobs I have ever given. Alice was moaning and twitching and flexing her hard-on in my mouth like crazy, so I’m sure she enjoyed it. She called out my name and told me she was about to cum before long, so I stopped her right on the edge of it and started to tease her asshole with my tongue instead. I poked and prodded with finger and tongue, enjoying what was just the prettiest little balloon knot. If you’re a fan of this activity, you know exactly what I mean. Alice loved it, and after a few more minutes she was begging me to fuck her.

“Can I get dressed first?” I asked.

“Of course, I wouldn’t have it any other way.” Alice winked at me.

I grabbed my bag and darted into the bathroom. I only put on minimal makeup, since I wanted to get to the fun part as quickly as possible. When I emerged in my outfit and rejoined her, Alice and changed too. She was now wearing a one piece fishnet lingerie outfit with holes cut out over the breasts and crotch and a satiny black thong holding her cock in it’s pouch. It was still rock hard, but instead of sticking out of the top of the waistband like mine was earlier, it was running to one side along her pelvis, totally covered with a wet spot near the tip which I can only assume was more precum soaking through. I on the other hand was clad in a red corset with black trim, a black leather mini skirt, black choker necklace and stockings of my own. My panties were red lace and covered less than half of each cheek. Alice stepped towards me and we resumed our make out session. Our hands thoroughly explored each other’s bodies and clothes. My cock pushed out of my panties and started tenting my skirt out. Our erections were rubbing and pushing together and at a certain point neither of us could take any more. I pushed her down onto the sofa and kneeled down in-between her legs. Alice grabbed a bottle of lube and applied a bit to my tip and then worked it down my shaft. I pushed into her slowly watching her facial expression as I went. I sped up, watching her cock swing and flop around as I thrusted. We switched positions with her kneeling in front of me and I fucked her from behind. Just as I was running out of stamina and my knees started going wobbly, Alice got up straight from her doggystyle position on her knees and pulled me over her shoulder to kiss her. I reached around and grabbed her cock out of her thong and squeezed and stroked it. When she told me to cum in her ass, that was more than enough to set me off, and I did just that. As I was filling her up, she twitched in my hand and whimpered. I felt the hot drip of her cum down my fingers as she gushed all over them. She leaned against me, sighed an exhausted “phew” and gave a little “nnph” as I withdrew myself from her. We just sat there catching our breath for a moment smiling at each other and trading giggles. We layer down together for awhile just snuggling after that and we both fell asleep. When we woke up, we went out for breakfast and one of the best friendships I’ve ever had started in earnest. We never formally dated or anything, or got jealous if one of us was dating someone else, but we have definitely been friends with benefits for years no. Also, whenever there’s a threesome opportunity when one of was dating someone else, we were each other’s first phone call. In fact that will probably be the subject of my next story.