tagTranssexuals & CrossdressersCrossdresser's Private Gloryhole

Crossdresser's Private Gloryhole


This is a true story, I am a crossdresser and this is the story of a wild wild night!

HI. My name is Leslie, I am a very dedicated crossdresser. I have to live as a male by day because of work. At night I usually get home pop open a beer and pop a buttplug in my juicy hole, get on the computer and watching some dirty naughty things until I just have to dress and get my freak on.

I started crossdressing with a mistress I had seven years ago. I was a full service sub, unsure of what my own limits were. She took me shopping and I bought panties, bras, lingerie of all sorts, outfits, shoes, and then she would take me home and get me dressed up in them and fuck me with dildos, strap ons and even fist me. The first time I wore women's clothes, I had an epiphany It felt so right, but she was horrible at makeup and I felt like a dude in a dress. I felt unfulfilled.

I didn't do it for a few years after she and I parted ways until while working as a bartender a gay couple adopted me and I started going over to parties at their house. I tried to play it off like I was straight but they saw right through me. Before long I was drunk, fucked up and dressed up like a whore. I looked at myself in the mirror and was forever changed. This was finally it. I looked like a woman. I felt like a woman.

I am a house painter by trade, and was smack in the middle of a big job. It was Friday. Finally. Being a painter creates some much needed shower and paint removal before I can dress up and have any fun. It was a very long, very hot day. I fantasized ALL day about getting home, getting dressed up and getting fucked in some way shape or form.

I live in a basement apartment with my grandma living upstairs, thank god she's deaf or almost at least. I finally got back to my side of town, and had plans of getting dressed up and putting an ad on the internet to get some action and I knew I would need some liquid courage. I usually drink beer but this time opted for a liter of rum and diet coke.

When I got home I was a crossdresser on a mission. I had a thought early in the day and it had been on my mind ever since. I wanted to set up a glory hole at home for some anonymous blowjobs. First thing is first, I got home and made a drink, put a big buttplug in my hungry ass and got online. I went to the website where I advertised for hookups. I posted an ad:

Sexy Crossdresser, Private Gloryhole for Big Cocks. Metro area 32

Hi fellas setting up a private gloryhole at home this evening and well into the morning. I want as many big cocks to suck and maybe fuck as possible. I am 32, blond, green eyes hwp, beautiful, wear makeup, nails done, heels, hose wig, very passable, It is 6:00 now, I will be ready by eight. I will answer all emails with a cock pick. If I like what I see I will simply respond with an address, Come in the bottom door and put your cock in a hole. Don't need to see your face. At eight I will start answering emails, hope to see you soon! Leslie (Pic Included)

Well that was it, I had my ad posted, now I just had to get my shit together and in a hurry. I had a system, post an ad, have a few drinks and watch some crossdressers sucking cock and fucking on the internet for close to a half an hour. I then ran for the bathtub. I don't know why but I prefer baths to showers, they make me feel more womanly. I furiously washed all of the paint off, then shaved my legs, clitty, ass and chest so I would be nice and smooth for my suitors.

It was now 7:00 I had to hurry. I went downstairs and what I did was I took two sheets, hung them up at an angle in my living room area, so you could see the tv, which I would have blowjob porn on. I stood up next to the sheets so I would know about the area the cocks would be and then I cut four holes in them.

I then got my outfit ready. A cute little pink shirt, a very short cotton skirt, a fresh pair of pantyhose, a white thong and a white bra and started getting dressed. Can't forget about the heels, I had a pair of clear plastic heels with silver straps. My best stripper shoes. I started getting dressed, bra, then my silicone inserts, pink shirt, black pantyhose, which I cut the ass out of for easy access, white thong and then my skirt and shoes.

All dressed up 7:25 I was running late. I grabbed my makeup bag, and made myself look like a slut. Foundation, heavy black eyeliner, mascara, black eye shadow, dark blush, red lipstick and red lip gloss. I grabbed my wig, brushed it, put it on and put it in a ponytail cause I didn't want it in my face while I was sucking cock. Next order of business was an enema. I was going to have my ass fucked tonight even if I did it myself. I took two full bags of water and got myself nice and cleaned out. I love enemas. They make me feel so slutty on my knees with a hose up my ass.

I grabbed the top mattress off of my bed, put it on the floor behind the sheets on the cocksuckers side, put a fresh fitted sheet on it. I grabbed three of my favorite dildos and lube and threw them on the mattress. I put the big buttplug back in my ass and made a stiff drink. I sat down at my computer and started checking emails.

8:00 on the nose I had made my deadline. I was checking my inbox and had 15 emails. Not as many as I hoped but I had high hopes they would still be coming in. The first one looked to be a nice thick cut cock probably eight inches long, There were a total of 5 nice big cocks in the first round of emails that I sent my address too.

I figured I would be busy so I grabbed my phone and headed for the mattress. I set my phone to alert me when I get new emails and I can respond from the phone. I put an eight hour cumshot dvd in so the guys could see my big tv. I couldn't see the tv, so no porn for me. I could hear the sucking sounds the girls were making and that was turning me on.

I slid my thong to the side and removed the buttplug and threw it on the bed. I grabbed a ten inch black dildo, lubed it up and stuck it in my ass. I was just laying on my side propped up on some pillows with my leg up fucking my ass nice, slow and steady. My ass was already primed between the buttplug and enema. It didn't take much lube. I started going a little faster, secretly hoping I would get off before my company showed up. I can't speak for anyone else but my best orgasms are anal orgasms, mind blowing spasming goodness.

I decided it was time to switch toys and went for another ten inch dildo, but this one was far bigger around, about the size of an average woman's wrist. I lubed this one up and sat on it, rode it slow for a bit, gradually increasing intensity until I was cumming like the little crossdressing whore I am, my ass grabbing onto it for dear life. Right at the peak of my orgasm I just sat all the way down on it as deep as I could get it and rocked back and forth. A great orgasm indeed.

I am in a heap on the bed and my front door opens, scaring the shit out of me. Someone is here already. A million thoughts are racing through my head. Which one was it? I quickly took the very thick dildo out of my ass and grabbed the previous one which is a little more comfortable. I have always wanted one in my ass while sucking dick but had never had the chance. Here was my chance.

Some strange man was in my house, I heard a zipper. The sound my dreams are made of. I had my overhead light on so I could see what I was sucking very clearly, but it was dark except for the tv on their side. It was dark looking through the holes. Through one of the middle holes comes a nine or ten inch very hard veiny cock. He pushes himself up tightly against the sheet, he is shaved with very large shaved balls. He said, "suck it bitch" in a deep almost disguised voice.

I Position myself on my knees in front of the hole so that I can ride the dildo and suck his cock at the same time. I have never sucked a cock this big and was slightly nervous about it but as not to keep him waiting I didn't dilly dolly around, I opened my mouth and took him three quarters of the way down and was licking the underside of his shaft just so he knew I meant business. I held it there for a minute, gagged a little and pulled my mouth slowly off of it stopping to suck the big bulbous head. I grabbed the shaft with my hand and lifted it up, I wanted to suck on those balls. I licked them both hungrily and then took one and then the other in my mouth and savored the flavor of his manhood. I licked them a little more. They were huge and I hoped full of cum!

I licked the shaft from base to tip on all sides getting this monster nice and wet. I opened my mouth and took him inside of me again, up and down, in and out, getting into a nice rhythm rocking on my dildo and sucking on his cock. It tasted so good. I love sucking cock. I worked my mouth slowly, savoring the taste and smell of him. He said, "faster cunt" and I obliged. I went to work on it feverishly, some like it fast, some like it slow, this guy liked it fast and that was okay with me. I felt him getting tense and tasted some precum so I took a deep breath and pushed my face all the way down on his cock, past my throat into my esophagus and just held it there, he said, "good slut" and pumped at my throat until he said he was going to cum, I pulled it out, aimed it at my face and stroked rope after rope of hot sticky cum all over my face. He didn't say a word just left. I love to swallow, but I love the feeling of having cum all over me even more. I just laid on the mattress and savored the feeling of being a cum dumpster.

I had heard my phone ding a few times so I checked my emails and sent my address to two more guys both of which were big and uncut, my favorite. I heard my door open again and waited for my next dick to come through a hole, I took the dildo out of my ass and replaced it with my buttplug, it was just too much work and I'd rather focus on the cock.

A flaccid penis entered the first hole. Good. I like a challenge. I didn't fuck around, I just opened my slutty crossdresser mouth and took his whole cock in there. I sucked hard on his meat and made my mouth tight like a virgin and fucked him with my mouth. I felt him get hard in my mouth, which I love. Without warning not fifteen seconds after he was hard He shot a huge very salty load in my mouth. It was one of the biggest cumshots I have ever experienced.

I heard the door open and it sounded like three people talking while I swallowed his salty load. Sure enough less than a minute later there were three more cocks poking through three holes that were next to each other. Someone said, "I brought a couple friends cocksuker." There was a beautiful uncut cock in the center with a lot of foreskin around the head, and two medium size cocks on either side.

I started from my left and took his relatively small cock in my mouth; it was probably five inches long and very thin. I easily took the whole length over and over and over again. I moved to the one on the far right, probably 6 inches and thick, I gave him the same treatment, I could feel his cock hitting the back of my throat over and over again, he grunted and I pulled out just in time to catch his cum on my forehead.

I went to the one in the middle, the one I really wanted, and put the whole thing in my throat and just held it there for probably a minute, I felt it pulsating in my throat. I was jacking off his friend to my left and working this big uncut cock over, nice and slow, sucking on the foreskin. His friend took his dick in his own hand, and started jerking, I grabbed the lube and covered his cock with it, he said, "thanks" and kept jerking, he told me as I was slowly devouring the middle cock that he was getting ready to cum so I put my face down by it and took it on my face, kind of a small load, but what can you expect from such a small cock. I went back to work on his friends uncut cock, working my hand and mouth in unison, manipulating his foreskin back and forth over the head and before long he filled my mouth up with a nice sized sweet tasting load. I swallowed it all.

They left and by this time it was late, and some of the guys had bailed on me I was figuring and no more emails had come in, I put a towel l on my couch and made myself a much needed drink, and sat down enjoying all of the cum on my face and in my belly. I felt very satisfied. I was content. I heard my phone ding so I went to the mattress to go get it and came back to the couch.

Sitting on my buttplug my clitty was hard but I wasn't going to cum until I got off every guy I could. I checked out the email, I saw the picture and my jaw dropped. It was beautiful. It was black. It was huge. Twelve very thick inches of man meat, I emailed back my phone number. A few minutes later he called, said he was in the same town just a few miles from where I live and he could be here in 5 minutes or so, I said "come on over."

I even took the buttplug out of my gaping ass, I didn't want to think about anything but this gigantic black cock. I waited for what seemed like forever. Twenty minutes had passed and I thought he wasn't coming and I was so disappointed. Just when I was ready to jack off my clitty and call it a night the door opened. He went to the right hole and in came this monster. My asshole ached wanting this monster in it.

I took it as far as I could go down on it but there was a lot of cock left I couldn't get. I worked my head up and down, with two hands twisting around this beauty. I couldn't believe it but he said, "I want that ass." I thought I died and went to heaven. He pulled the sheet up and there was a beautiful black man with a gargantuan black tool. He flipped me to doggy, I handed him the lube and I felt it tickling my hole. It didn't tickle for long. He pushed. It was so thick. I was already well lubed, and he didn't take much mercy on me, he had it in as far as it would go.

He was hammering me. I felt so full I thought I would die. He manhandled me and put me on my back with my legs up on his shoulders, he fucked me slow sensually and deep, god it was deep for probably a half an hour before pulling out and spraying me from my belly to the top of my head with a torrent of cum. He said thanks got dressed and left.

I had a wonderful night. After being worked over by that big black cock(I was sore for days) I simply fell asleep with cum from head to toe. It was one of the best nights of my life. I can't wait to do it again.

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