So last Halloween I (27 M) decided to rock a cross dressed costume for a party my friend was having. After much debating as to what to wear I was convinced by several friends to go with Harley Quinn (the suicide squad version before anyone asks).
I had to wait almost three weeks for the costume and it was all I could think about through that entire time. When it finally came I was over the moon, it fit exactly as advertised! I went to The mall the next day to pick up some undergarments (I figured may as well go the whole way if I was crossdressing) and wound up with a pink thong (avoid those panty lines) and a matching bra. Not gonna lie, I put those on many times before the night of the party.
Halloween finally came and the party was a lot of fun, I had spent a full 2 hrs getting dressed and putting on my makeup and not to toot my own horn but I looked pretty good. Everyone was drinking and dancing and I was hanging out a lot with the hosts roommate (34 M). He was taller than me, cute, about 6 ft 1 with really nice tatted, muscular arms. We did several shots together and danced a bit and we’re having a lot of fun. After about an hour of only hanging out with each other he invited me to take a look at his comic collection (I was dressed as a DC character after all).
I’d say it took him about 15 seconds maximum after I entered his room before he closed the door, had both hands on my ass and his tongue down my throat. He was an amazing kisser and I was rock hard almost immediately. He suddenly broke away and sat down on his bed, I went to join him (a distance of about 10 feet) when he suddenly said “crawl”. He had been very easy going up to this point so I was shocked but very into it.
I got on all fours and crawled over to him, he immediately said “turn around”. I spun around and felt him spank my ass hard. I winced but again, was shocked but into it. He gave me about eight or nine more intermittent swats before ordering me to turn back around. When I did his cock was already out, he was about 7.5 inches and very thick, I’m about 5 so he was def bigger than me. I was so turned on at this point so I just started licking him up and down, all over his shaft and giving a good tonguing to his balls. Immediately once I introduced his shaft to my mouth he grabbed my hair and started sliding himself in and out of my mouth. Every now and again he’d shove himself deep until I gagged and made my eyes water but for the most part he seemed to just read my limits.
I was completely lost in my oral efforts when he suddenly pulled out of my mouth and grabbed my chin. He looked me in the eye and asked “do you want me to fuck you”. I nodded aggressively. He told me to open my mouth and when I did he spit into it and asked me again (once more, shocking but I was so into it) and I begged for him to fuck me. He stood me up and ripped off my shirt and short, he told me to leave on my fishnets bra and thong. He got me on all fours on his bed and I could feel him squirting lube on my ass and massaging a finger in.
I was so turned on at this point that all I could say was please, and soon enough my wish was fulfilled. I felt my thong pulled to the side and his head pop into my awaiting hole. He was thicker than I had experienced in a while and I cried out at first when he entered me, but as he slowly thrust in and out I felt myself relaxing, the shock of entry replaced by radiating waves of pleasure.
Once he got his rhythm he started fucking me senseless, driving himself in and out of me with each powerful stroke. I was limited to moans and the word fuck, loving every second lost in my own lust. We switched positions a few times, me riding him for a while, impaling myself on his cock as he talked dirty to me, then on my back where he spit in my mouth some more and we made out aggressively. Finally I could tell he was getting close and he abruptly pulled out. He walked away for a moment and came back with a hairbrush. He told me to fuck myself with the handle while sucking him. At this point I was so turned on I would’ve said yes to him no matter what. I took him back in my mouth and started fucking myself and within 30 seconds he pulled out and came on my face and in my hair. He came a ton too, like 5 or 6 thick ropes I was covered. After he got his wits back he bent down and started stroking me. He asked me “do you want to cum” I nodded whimpering. Again he ordered my mouth open and spit in it before asking again, I blurted out “please” and he ordered me to cum. I shot a massive load straight onto my stomach and chest.
We both caught our breath and traded numbers, he offered to let me stay over but I wanted to head home. I cleaned up the best I could, got my clothes back on (though my shirt was stuck to my chest with my own cum) and got an Uber home. Upon getting home I def still had visible cum on my eyebrows and hair, knowing that the uber driver saw me that way turned me on so I grabbed a hairbrush and fucked myself until I finished.
A fun epilogue to this story is that the next time I saw my friend he said several party guests could hear me sucking his cock (I guess I give noisy head) and some of the start of him fucking me. I saw him a few times after that but the first time was definitely my favorite.
I hope you enjoy my story and if you want more I definitely got more, feel free to dm me with questions or story requests!
Source: reddit.com/r/gonewildstories/comments/jcgy71/mm_some_fun_from_last_halloween