A quick one with a cosplay cross-dresser [FM]

This brief encounter actually happened over a month ago, at the last cosplay convention of the year for me, but I’ve been so busy I’ve only just found time to recount it. It had been a dry spell for me, with no meetings and an unsuccessful Comic Con, and given that I was hanging out with a group of friends at the year’s final event I didn’t really hold out much hope of that changing here. Nonetheless, sat drinking on the second night of the convention I couldn’t resist pulling out my phone and swiping through Tinder matches – there wasn’t much of interest, but I did find a couple of people who were also at the event, and one of them almost instantly matched me back a couple of minutes after I’d swiped.

The guy in question was 21 and a tall, lanky cross-dressing cosplayer I’d already seen around the con… he’s seen me too clearly, as he noted in his opening message. The small was pretty short and sweet before we both came to the same conclusion – we were both horny, and we both needed a release. The only question was when and how we’d separate ourselves from our respective groups of friends.

As the night’s main party began, he spied his opportunity and messaged to me to meet him at the other bar at the hotel where the convention was taking place in five minutes, giving me a little time to conjure up an excuse (which was a boring “Oh, someone I know just messaged me, I’m going to go say hi.. I’ll be right back!” before heading off up the stairs to the bar in question. I spotted him immediately – it’s hard to miss a 6 foot 4 tall cosplayer dressed as Rise from Persona 4 (a cosplay I also own myself, I told him excitedly during our very brief spot of small talk), sporting a long-white blouse, patterned short skirt and thigh-high stockings. For my part I’d chosen to spend the day as Chitoge from Nisekoi ([https://imgur.com/ww7Nzw6](https://imgur.com/ww7Nzw6)), wearing a blonde wig with a red ribbon in it, short-sleeved white and light blue blouse with a neck tie, short blue skirt and black thigh high socks with simple shoes.

Once I went over to him and he spotted me, things quickly got intense – after the quick “how are you doing” pleasantries, he leaned down to me in the middle of the noisy bar, putting his mouth near my ear and saying simply “so you want to come upstairs and get fucked?” I’m sure I blushed – I felt my face flush – as I nodded, and he was soon striding towards the lift as I almost struggled to keep up.

After impatiently probing at the lift buttons a few times, an empty lift finally arrived, and after punching in the floor number of his room he came around behind me – I watched in the lift mirror, then took in my breath as I felt his erection from beneath his skirt press against me. “I need this so much” he said, making eye contact through the reflection in the mirror. “Me too” I told him. I saw his hand reaching up to slide up my skirt, but the lift reached our floor by then and so he snatched it away in case anyone was waiting outside, and ushered me out of the lift and towards his shared – but currently empty – room.

His room was inevitably messy, with stuff strewn everywhere, and so there was a brief pause as he hurriedly swept items from his bed onto the floor. With that problem solved, he was soon standing before me again, and this time there was nothing to interrupt his hand touching my leg, and impatiently running up my thigh. After the briefest of teasing touches over my white cotton underwear, his hand was inside my knickers, moving down inside them to find my pussy already wet and waiting for him. “So wet already, I love it” he muttered, making eye contact with me before my own eyes closed as his fingers moved from rubbing my wet slit to find and rub my clit. He spent a minute or two first rubbing me, then slipping a finger and then two inside me. Satisfied I was ready, his hand was removed from my knickers so that he could hurriedly pull them down to my ankles. While I completed the task and stepped out of them, he reached under his own skirt to pull down the black cycle shorts protecting his own modesty, allowing his hard cock – quite long and thin – to spring free under that skirt, which he then also swiftly unhooked and let fall to the floor.

Without being asked, I climbed onto the bed, laying back as he stuck his hand into a bag next to the bed and quickly pulled out a condom, tearing open the packet and smoothly rolling it down the length of his cock. As he joined me on the bed I instinctively spread my legs, pulling up my skirt for him as I did so to offer him full access to me. He didn’t need any further invitation and was soon positioned between them, taking his cock in his hand and rubbing it up and down the length of my pussy, testing its wetness as I breathed more heavily beneath him.

Satisfied I was ready, I now felt the head of his penis pressing between my lips, and moaned slightly as I felt the tip pushing inside me. He was slow and deliberate as he entered me, taking a few movements before moaning himself as he finally slid his entire length inside me. From here he moved slowly for a little while, taking just a few moments to enjoy the sensation of my pussy gripping him (“You’re so tight” he told me), moving in and out carefully before quickly moving to build up a pace and rhythm. From sitting on his haunches he was now leaning forward over me, watching my facial expressions as he fucked me while I gripped the bed, my legs spread either side of his body. I felt a little self-conscious of his intense stare as he moved in and out of me, which I broke every now and then to look down and peer over my hiked-up skirt to watch his cock rapidly and easily slipping in and out of me. I wished I could see myself being fucked from the doorway of the room to get a better view of him inside me.

For a few minutes no further words were spoken, and the room was quiet but for the sound of his cock moving in and out of my wetness, our heavy breathing, my moans and gasps under him as he fucked me and the rhythmic movements of the bed. I was enjoying the feeling of a new cock inside me, and especially one from a guy I’d only met five minutes previously, and he seemed to be loving it too.

Eventually the relative silence was broken, and he asked me to get on all fours as he pulled away from me. I did as he suggested, hopping up to my knees and turning around for him before he guided me to the edge of the bed. Once in place, I felt a hand on one of my hips, and then his cock being guided back inside me as I moaned slightly again. Back inside me, those hands now tightly gripped both of my hips, as he started to move, building up speed quickly as he thrust into my wetness. In next to no time, he was fucking me hard – the bed was rocking, and I was moaning louder as his body slapped against mine over and over. I reached down and started to rub my clit frenetically as he pounded me, and after a period without sex and a few days without masturbation I was quickly finding myself getting close to release.

The increasing urgency of my moans told him that I was getting close, and he breathlessly urged me to cum on his cock as he continued to relentlessly fuck me with an impressively constant, unbroken rhythm. I didn’t need to be told as I was already on the brink, and my fingers rubbing my clit hard pushed me over into my orgasm as my pussy contracted around him involuntarily. He barely broke his stride however, continuing to fuck me through my orgasm, although as mine subsided so his built. He warned me that he was about to cum, and fucked me even harder as he began to throb and ejaculating inside the condom with loud groans as I panted and tried to regain my own breath in the meantime.

Both spent, he pulled out and discarded the condom, and quickly set to putting his skirt back on, while I clambered off the bed and hunted around for my knickers which had also been left on the floor. Pulling them back on, I checked my cosplay in the mirror while he pulled his bike shorts back on, and with barely another word said we said our goodbyes and I slunk back out of the room. Taking a slow walk to allow my flushed face to cool off in the hotel corridors, I returned to my friends with some non-committal answers about the “friend” I’d just met, feeling that bit more satisfied as I took a much-needed refreshing sip of my drink.

Source: reddit.com/r/gonewildstories/comments/eed38a/a_quick_one_with_a_cosplay_crossdresser_fm