I was in my mid-20s and went to a two-day anime convention. It was in a city that I lived about 40 miles from and I bought tickets for both days (Friday and Saturday), so on top of buying the tickets, I also got a hotel room for the entire event. I had been a closet cross-dresser for several years and finally had enough courage to go out and dress up in public. I wasn't sure what was going to happen, nor what I was willing to say no or yes to, so I also packed lube and condoms. I had experience with men and women and my preferences flipped depending on my mood. It had also been a few months since my last sexual encounter, so I was open to just about anything. My bisexual experience was limited, topping a couple of times and giving head was about it. In anticipation for this weekend, I had been dressed up with my ass lubed and toys in me pretending to be the convention mattress. Pretending is one thing, actually doing it is another.
I got to the hotel room on Thursday, checked in, and took my things up to my hotel room. After dinner, I proceeded to prepare for the next day. I spent quite a bit of money on this weekend. The costumes weren't cheap, and I wasn't going as any particular character, just as a generic female in a schoolgirl outfit. I shaved and lotioned up. I wasn't going to be "me" this weekend, I was going to be this character, even down to when I was alone in my room. So when I went to bed, it was in a pair of panties and a nightgown.
I got up, shaved again, showered, lotioned, applied makeup (something that I had been practicing over the last couple of months), got dressed, including a pair of false tits, and went down to the convention. I was having a blast looking at the booths, meeting people, getting hit on, playing games, watching some of the movies, and other convention stuff. It got late and all the interactive stuff ended and it was time for the presentations and speeches, I decided it was time to leave for the day. Personally, I hate that kind of stuff. Sitting down quietly in a dark room while listening to speeches and presentations and endless Q and A sessions wasn't as much fun as the other stuff I was doing. Plus, I was already missing all the people who had been hitting on me. So, during one of the early presentations, I quietly got up and left. All the booths were closed and no movies were playing. It was clear that we were all supposed to be in that presentation room. I would rather do anything else.
I got up to my room, took off my shoes and skirt, and just relaxed on the bed as I watched television. I ordered a pizza and then realized that I wasn't really prepared for someone outside of the convention to see me dressed as I was. I put my skirt back on when the pizza guy handed me my pizza, he gave me a bit of a weird look and left. Oh well.
Later that night I heard a bunch of noise. Loud music and voices. I looked out the peephole, but couldn't see much. I poked my head out the door, still in the wig, and saw a huge party a few doors down from me. Someone saw me and said, "Hey, come on!" I grabbed my keys and went down to the party. It was like some unofficial after-party from the convention. Most of those there remembered seeing me, and I remembered seeing most of them as well. Most of those there were men, which wasn't unexpected. I was handed a beer and talked to a few people. As my beer ran out, I was handed another and another. I wasn't complaining as I had spent most of my money on the convention and the room. That pizza was only ordered because I was confident I could stretch it out through tomorrow.
As the party continued, I could feel the beers taking their effect and it was getting harder and harder to ignore the fact that the flirting and people hitting on me had shifted to me getting touched. My legs, my hips, my ass, and no, I wasn't hating this. One guy had been behind me for a few minutes, I could feel his hard, and his hand on me. He sat down on the bed and his hand moved to my leg as we talked and drank, his hand crept up my leg and onto my panty-clad ass. My dick was hard and I was honestly pondering if I wanted to or not, fuck him. Finally, I decided that part of why I came out here dressed up was to slut and if I turned this down I was going to regret it. So I moved his hand out from under my skirt and I looked at him and mouthed "Let's go."
I led him to my room. I didn't turn the lights on, I just closed the door and said "You're only getting a blow job."
He didn't say anything, he just unzipped his pants and took his dick out. I dropped to my knees and in the darkness of my hotel room, I took his hard dick in my hand and slowly put it into my mouth.
I closed my eyes, enjoying the smell and taste of his dick in my mouth as I moved my head back and forth. I could hear his moans of enjoyment on what my mouth was doing. I hadn't done this too much, so I knew this wasn't the best that he had ever gotten. Suddenly, he took my head in his hands, he got really aggressive with me and started to face fucking me, telling me that I was a Convention Slut looking to suck as many cocks as possible over the weekend. Well, he wasn't really being proven wrong at the moment. He then said that if I didn't get him to cum in my mouth soon that he was going to fuck my ass. I started to gag as his dick went farther down my throat than I expected and then he came. Some of it got onto my shirt and tie. Some were on my chin. I swallowed what I could. He took his dick and wiped the head on my cheeks.
I sat there on my knees as he put his dick away. I slowly stood up and opened the door. I was expecting him to thank me for what we just did. Instead, he took the door, opened it wide, and led me out of it and back to the party. Once we were back, he showed me off, pointing out the cum on my shirt and cheeks. There were cheers. I was given a glass of vodka. As I sat down on a bed and drank it I listened to him tell everyone there about my head game. I was then noticing all the attention on me. There were no women at this point, most of them either hooked up with someone or just went to bed.
I laid down on the bed as I finished the drink. I was no longer focusing on the conversations. Someone had rolled me over and was dry-humping me. I said to his guy "I need to go back to my room."
He took my hand and walked me to my room. I entered my door and he came in, uninvited. I laid on the bed, face down, and he got on top of me and continued to dry hump me. I am drunk, and my dick is hard and needs some release, and so is his dick.
"How about a quickie and then you get the fuck out of here?" I asked.
"Sounds good to me," he said.
I pointed to the table next to the bed "Hand me that." I said, pointing to the lube and condoms. I watched him grab the lube and heard his pants open and the sound of lube being applied to a dick. I then felt my skirt go up, my panties get pulled down and his dick stretch out my asshole and the feeling of his dick enter me. It was painful at first. I had done bisexual stuff in the past, but this was the first time I was taking dick in my ass. I had often fantasized about this and ran dildos and vibrators back there, but this was my first dick. Eventually, the pain went away and it really started to feel good. I wanted to touch my dick and jerk it, but I was on my belly as he fucked me. I couldn't suppress the moans that escaped my mouth as he plowed in and out of me. He didn't say anything to me as he fucked me. He started to pound me harder and faster, then he pulled out and rolled me over. I lifted up my shirt and he came all over my belly and rock-hard dick.
In the limited light of the hotel room, I watched as he fastened up his pants. I rubbed my cum covered dick until it came over my belly, giving me that much-needed release.
After the door closed behind him, I heard him tell the others that I was easy and tight. I laid on my back, listening to what was said and feeling very good. I removed my clothes and fell asleep.