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my first crossdressed gangbang
my first crossdressed gangbang · Crossdressers · Hello! I am a 55-year-old bisexual male who loves to cross-dress, and this is my true gang-bang story. It was a lot of fun and I would love to do it again someday. Maybe when I do, I’ll write about it here. ;)
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.
I could feel their cocks in my stomach as shot after shot of hot cum was unloaded deep in my ass. They must have dumped at least a quart of cum in me. I was so full of cum that it squirted out of my ass and all over the guy behind me when they pulled out. Once they were done, the other men all had another go at me.
After watching the other men run a train on me for a little while, one of the black guys came over and started talking to me. He told me I was incredibly sexy and introduced himself and his friend as Rick and Marcus. He said he had a business proposition for me.
"We own this joint, how would you like to do this every Friday and Saturday night? We’ll pay you 200 dollars per show. We charge spectators a fee and we will find you the biggest, hottest dicks around with a minimum of six to ten guys".
They told me to think about it since I could not answer right away as my mouth was filled with cock. It went on like that for another hour before the last guy finally came. I was absolutely filthy from head to toe. I was covered in a mixture of jizz, spit, and sweat; I must have stunk something awful.
I got up and walked to their office. I was horribly sore and exhausted but couldn’t keep the smile from my face. I opened the door and said that I would be happy to work for them. They were excited to hear it.
"Since you’re gonna be our new slut, how about you come over here and give us some head. Think you can handle a couple more loads?" Marcus said, already unbuttoning his pants.
"Hell yeah!" I sank to my knees in front of them and happily sucked them off one at a time until they came.
Marcus finished in my throat. He held my head all the way down as he unloaded his hot, sweet cum in my stomach. Rick came shortly after but instead of cumming in my mouth, he sprayed it all over my face.
"I’ll see you guys tomorrow!" I said as I stood up, still covered in cum and looking like a beat-up whore who had a rough night. I knew my clothes were ruined, and my makeup must have been running down my face. On my way out, I stopped by the bathroom to clean up the worst of the cum dripping down my body. I was still so horny that I didn’t bother changing my outfit. I just grabbed my backpack and walked back to the hotel dressed as I was, heels and all. I was hoping that I might get propositioned by someone looking for an easy, late-night fuck.
It was around three o’clock in the morning when I left the video store. I was coming out of an alley when a police car pulled up beside me with the lights flashing. They probably thought I was a prostitute, and I was scared they were going to arrest me. I was trying to find a believable excuse for why I looked like a hooker when two big muscular cops got out of the cruiser. They surrounded me, pinning my back against the alley wall.
"Well, what do we have here? A sissy crossdresser faggot?" The one in front smirked at me while his partner laughed.
"What happened to you?" The second cop looked me up and down, taking in my disheveled appearance. The first cop whispered something into his radio, but I couldn’t hear what he said. I was hoping he wasn’t calling for backup.
I proceeded to tell them all about my night at the adult video store. Still, carefully leaving out the part about me working there, just in case they really did intend on arresting me for prostitution. Another cop car pulled up to check me out, and I regaled him with my escapades as well. I noticed all three cops had bulges in their pants and grins on their faces. After I finished my story, I could tell they were all pretty aroused. The second cop stepped closer to me with a sly smile on his face.
"Listen slut, we have a little deal for you. You blow all three of us right now and you won’t spend the night in holding for whoring."
And that was how I found myself on my knees, surrounded by three cops with their big hard cocks out. I sucked all of them off until they came in my mouth. I swallowed all their cum with a big smile. True to their word, they didn’t arrest me and let me continue my slut walk of shame back to the hotel.
Once I got back to the hotel, I was able to sneak in one of the side exits using my key card. I knew if I tried to go in through the front lobby looking the way I do, they’d probably kick me out. I was tired and sore when I got up to my room but still very excited for the day ahead. I kicked off my heels and peeled the cum soaked lingerie off my body. I took a nice hot shower and douched the last of the cum out of my gaping asshole. Once I was all clean, I got in the bed naked and was out like a light.
he following night around 12:30am I walked back to the bookstore dressed the same way, but I was wearing a red outfit with a tight black mini skirt, I took the back way this time to avoid traffic, but I had to walk through a big truck stop to get there
I looked around the truck stop before continuing and only saw 3 trucks all dark so I continued on and I stopped to check myself in the bathroom mirror but just then 2 truckers walked in as I was about to leave they took me into the bathroom and fucked me as I sucked them off. One came in my ass and one in my mouth and I was on my way.
When I arrived at the bookstore I walked in and was greeted by the two large black men from the prior night (the owners) I was quite horny and looking forward to what the night had in-store. I was wearing my clity Cage, my strap-on tits with a hot red and black latex boos-tier, lacy red G-string panties, with matching garter belt, black thigh high stockings, and my 8-inch red stripper heels and a huge Butt plug with a long black fuzzy tail.
The 2 black men escorted me through the bookstore where it was quite crowded with lots of horny men. We went back to their office where I sucked both their cocks as they gave me the rundown of the night. The one with the husky deep voice explained that they had 10 well hung guys that were just dying to get at me. Then the other guy spoke with a much higher fem voice with a slight lisp.
He said that they had a private room in the rear all set up and there were going to be about 20 people that were just going to watch and enjoy the show, they also said that pix and video were going to be shot.
About that time one of them shot a huge load of cum in my mouth it was so big I thought I was going to drowned, but I managed to swallow it all. The other guy came around back of me and removed the huge butt plug I had in and shoved his huge black cock in my ass and started to fuck me hard after a few minutes of this he shot a huge load of cum deep in my ass.
It felt like he was filling my stomach. I loved it, it felt so good that it made me cum, and no one had even touched my cock yet.
They then shoved my plug back in my ass and said don’t want all that good lube to drip out, then pulled me to my feet and escorted me through the bookstore where everybody started clapping and whistling.
I then noticed that on one wall there was a large flat screen monitor that showed their office where I just got the 2 men off and realized that everybody in the bookstore just watched me get them off and that turned me on even more.
We walked through this door in the rear and inside was a sex swing, bed and 2 couches, in the middle of the room were 9 of the biggest cocks. All around were men and some women seated all naked and waiting for the show to start.
I strutted into the room and went right to work. I started sucking the first cock I came to. I am telling you there was not a cock under 8 inches.
Almost immediately my panties were taken off of me and my ass hole eaten, lubed then filled with cock as I sucked cock after cock as cock was being shoved in my ass after a little while the first load was shot right in my mouth I swallowed every last drop of it, then I felt the huge cock in my ass erupt with a huge load deep inside me it felt so good.
Then another cock was shoved in my mouth and then before the other pulled out of my ass another cock invaded me and I was being fucked in my ass by 2 huge cocks at the same time.
After a little while it got quiet and in walked this Arab guy, he had the biggest cock of them all, I swear it was at least 12 to 13 inches long and so fat it looked like a little baseball bat, I thought it would rip me in half. I tried to get it in my mouth, but I could only get the head of it in, he went around back of me and started to push his huge cock into my ass which was dripping with cum and very well lubricated, it felt like he was ripping me.
He was gentle and took his time though. finally, the head of his enormous cock popped into my ass I tried to scream but my mouth was full of cock. he slowly entered me until he was almost all the way in and then slowly pulled out all the way leaving my ass gaped, then he shoved it back in.
He did this several times until I was used to it and it started to feel real good then he slammed it in as far as it would go and started to pound me hard, all I could do is moan as the cock in my throat erupted at the same time and was pulled out and replaced by another. he fucked me hard for what seemed like an hour before he shot this enormous load into my ass, it felt like a fire hose inside me it was by far the biggest load I had ever had.
It was so much that it was seeping out as he continued to pump my ass. it turned me on so much that I shot my own load I could feel my ass hole clamping down on his enormous cock as he moaned as I used my asshole to suck every drop of cum out of that wonderful cock.
He finally gave me all he had to give I could feel his cock going limp and he pulled out. 2 other cocks took his place quickly. this guy would fuck my ass 2 other times throughout the night, this went on for hours until I had every cock cum in my ass and in my mouth I was covered with cum and loving it.
When they were all done I went out to the audience and started to do some of them, I was so turned on I could do this all night then the 2 Owners came in and had 2 tall shot glass's filled with cum from the audience and wanted me to drink them.
I did, it was so good I licked the glass's clean then they both fucked me in the ass, it was so good to have these 2 huge black cocks deep in my ass as I felt them both cum in my ass, it was dripping cum as I stood up and they handed me 200 hundred dollars and a video tape of the whole thing and said will we see you next week?,
I said hell yeah they said that they had already had about 15 guys for me next week and I said can’t wait. I left shortly afterwards dressed like a slut.
I was still covered in cum and had the huge butt plug in my ass to keep in all the cum as I walked towards the truck stop where it was full of horny truckers. again, I was taken to the bathroom where about 4 truckers waited for me, I sucked off all of them before I started my walk back to the hotel room.
But, before I got there, I decided I wanted to stand out on the corner across from the truck stop hooking myself out for the rest of the night.
I got 3 guys and sucked and swallowed each of them for 20 bucks each. the sun was Cumming up, so I stood on the corner and jacked off for all to see until I shot my own huge load all over my self. I was soaked in cum from all the cock I had throughout the night and my ass dripping cum I then walked my slutty ass back to my room and popped in the video they had given me and started to jack off to it when there was a knock at the door!
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