My First Time Crossdressed Gangbang Story
I was 26-years-old at the time and traveling all over the country for my job. My work kept me in a new state for about four months, then it was on to the next one. I would always choose a hotel that was close to an adult bookstore or an all-male spa, and if those were not available, a truck stop would do. Luckily, in this case, there was an adult video store about 10 blocks away.
Late one night, after a few beers and getting a bit stoned, I got extremely horny. I was in the mood for getting dicked down while dressed like a little slut, and I knew exactly how I wanted it.
I had some experience sucking dick and enjoyed the occasional ass pounding now and then, but I had always wanted to be gang-banged bareback by a group of well-hung guys while dressed like the whore I am.
But before I set out to fulfill my fantasy, I had to get ready. I showered and shaved my entire body smooth, with special attention to my crotch and ass. I applied makeup, bright and thick to make my eyes and lips pop. Long, trashy red acrylic nails and matching toes rounded out the look of a hot and ready hooker.
It was about 10:00 pm when I packed my backpack with everything I needed. I stuffed in my blonde wig, strap-on titties, sexy black lace bra, matching panties, black thigh-high stockings with a bold back seam, garter belt, and a pair of black six-inch stiletto stripper heels. I also made sure to throw in some lube and several dildos of various sizes.
As I headed out, I had decided to walk since I was still a little buzzed. I made my way to the local adult video store. I had already been there several times on previous trips, so I knew they had viewing rooms, some with glory holes. That was where the real fun happened. This store was one of my favorite hook-up spots because I could always find easy cock. I was confident that I'd have no problem getting all my holes resized tonight.
When I arrived, I noticed it was quite crowded. I went to the counter, got 30 dollars in single bills, and proceeded to the back where the booths were. My favorite booth was available and I took that as a good sign. I liked this particular stall because it was small and had a glory hole on each wall. So if I got on all fours, my ass would be at one hole and my mouth would be at the other.
I'd normally just change in the booth, but I was so horny that I decided to change in the restroom. Next, I had to prepare for the night ahead of me and chose to warm up with some intense dildo action. I took the assorted plastic and rubber phalluses out of my bag and got to work. I started with the thinnest one, lubricating it thoroughly before sliding it up my butt. I stroked it in and out of myself for a few minutes, letting it flirt and tease my prostate, quickly getting in the mood. I had to bite my lip to keep from moaning out loud. I could feel my cock hardening, but I had to resist cumming, lest I spoil my plans for the night. One by one, I repeated this process with all the dildos, working my way up from the smallest to the largest. All the while trying my hardest not to shoot my load all over the restroom stall.
Once I was all lubed up and ready to go, I shoved a giant butt plug in my ass. It was so big that it barely fit and kept me stretched open wide. I quickly finished dressing and put on my heels. I was eager to get this show on the road. I walked out into the store proper, where several guys stood around, chatting and laughing. I felt daring as I strutted by them on my way to the booth, making sure to switch my hips to bring attention to my legs and ass. I even winked at them over my shoulder. The cat-calls started almost immediately as more and more patrons took notice of my scandalous getup. I felt like a real slut, and with all the stares I got, I knew that I was in for a good time. I stepped into my stall, purposely not locking the door behind me. I put in a few dollars and selected a sexy gay bareback gang-bang video, the kind I wanted to recreate. I didn't have to wait a whole minute before a nice, cut cock about eight inches or so came through the glory-hole facing me. At the other hole, I saw another guy watching me and jacking off, so I got down on my hands and knees, settling onto the cum soaked floor. I began to slowly suck the dick in front of me, simultaneously removing the huge plug in my ass. I replaced the plug with a huge dildo with a suction cup base, making sure to give the guy behind me a good view.
I stuck the fake dick to the wall just below the hole he was watching and slid my ass onto it, rocking back and forth, putting on a show. The guy behind me must have gotten tired of just watching because he thrust this cock through the glory-hole and tapped my ass with it to get my attention. I briefly paused the blowjob to look back at the new dick. It was huge! Roughly 10 inches long and as thick as my forearm! I absolutely had to have it inside me. I removed the dildo, leaving my asshole gaped, and the monster cock slid right in, all the way to the hilt. He started pumping into me bare as I sucked the other cock. It felt so good, and I was close to cumming when the cock in my mouth shot several streams of hot yummy cum down my throat.
I swallowed every last drop, and the guy left, obviously satisfied. Still, I continued to hold back my orgasm, knowing that it would be worth it later. Barely a second passed when another big hard cock came through the hole, and I got back to work sucking while my ass was being pounded. The man behind me hammered my prostate, making me moan around the cock in my mouth. Not long after, the cock in my ass erupted. I could feel spurt after spurt of thick cum being shot up my ass.
The door to my stall opened, and there stood four or five guys, all big and buff and stroking their huge cocks while watching me get fucked. As soon as the cock I was sucking filled my mouth with another delicious load, I was pulled into the hallway by this new group of well-endowed men. Each of them took turns using me. For the next hour, my ass was constantly stuffed with dick, and my stomach was full of jizz. When they were done, my entire body was sticky with sweat and cum. The men were fully sated, and none wanted a second round.
I hadn't expected my night to end so quickly and was very disappointed. Just then, two massive black guys walked in, and I knew that my night wasn't over by a long shot. They surveyed the scene and saw me in my ruined lingerie and makeup. I gave them a flirty, gooey smile and beckoned them over with a finger. They must have liked what they saw because they started to strip while everybody watched. When they were completely naked, my jaw practically hit the floor. They had two of the biggest cocks I have ever seen! Both must have been 11 inches or more and thick as a baseball bat. One even had a nice upward curve that I knew would feel amazing on my prostate.
The one with the curve got behind me; I felt him lineup his huge cock with my cum-lubed ass and slowly pushed in. It was bigger than anything I had taken so far and hurt going in. When he was about halfway in, he began slowly pumping in and out. Allowing me to get accustomed to his impressive size.
The other guy grabbed my head and tried to shove his huge cock down my throat. I could only manage to get the head in. The others stood around and watched. Some were even taking pictures and filming me from every angle. After about 10 minutes, the man in my ass shoved his huge cock all the way in. I could feel his balls pressing against mine. It was so long, I thought I could feel it in my stomach. Then he really started to fuck me hard, and all I could do was moan with pleasure. I was so turned on, and it felt so good that I shot my load from just being fucked, splattering the floor with my cum.
I finally managed to swallow a few more inches of the cock in front of me. I could feel it reaching down past my tonsils. I knew that I would have a sore throat in the morning. After a while of fucking me like this, they decided to switch it up and trade places. I could taste my ass and the other men's cum on his dick and eagerly slurped it all up. I had lost track of time. The one now in front pulled out of my mouth and went around back. At the same time, the other one slipped under me. I sat down on the cock below while the other man began pushing his way into my already occupied asshole.
I started to protest, thinking these two must be crazy. One massive cock barely fit on its own; two would surely split me apart! Before I could fully voice my concern, the head of the one behind me popped in, and I almost screamed. It hurt for only a minute or so. Before I knew it, I was being double fucked by these huge black cocks.
The other guys must have decided that they were ready for round two. They came back into it, fighting to shove their cocks down my throat and dumping what seemed to be gallons of cum into my stomach. At this rate, I wouldn't need to eat for days. The two guys fucked my ass like that for another half hour, alternating thrusts, so I was always full before adding to the collection of cum in my ass.
