It might be good to follow this whole story from I want to be a girl to I want to be a woman chapter 2
By the time I was 15, I was an amazing fucker. I could take a big cock deep in my ass and suck cock like a pro and swallow lots of cum. I had lots of practice by this time. But not only could I fuck, I was getting much better at dressing up like a girl. It helped that my stepdad kept buying me clothes and my hips were starting to spread some from the Hormones he gave me which help me fill out the short skirts I mostly wore. I was also much better at makeup and my hair was long enough I could style it more like a woman when I dressed up.
But my mom did not know, although I think she had a clue. The only time I could dress up was when she wasn’t there or when I would sneak out. And I had started to experience other sexual experiences other than my stepdad or stepbrother. After sucking and fucking a couple of teenage boys, I knew I needed to focus on men. The only thing teenagers had on older guys was large amounts of cum, which was great, but I liked the way men used their cocks better.
I soon found out that if I hung out around the adult video store I would score lots of action. At first I would just hang around the parking lot, dressed up in some short skirt outfit and completely slutted out, and would ask some of the guys who were leaving if they wanted to suck or fuck. Some guys, surprisingly, would turn me down. But I got to suck a few cocks in cars before something happened that surprised me.
My second night at the adult video store I approached a taller, slightly muscular black man to ask him if he wanted a blowjob. He said, “How much?” It was a question I had never considered. I had no idea what to say. I paused and said, “How about 10 dollars?”
He said, “Lets go into one of the booths in the video store.” I had no idea what he was talking about. I was worried that I would get carded and found out, but we walked in together. It was sensory overload for me. There were all kinds of porn videos in different categories, but what really caught my eye was the toys. There were handcuffs and dolls, but the dildos were really amazing to me. Some of them were so big I could not believe anyone would shove something that big in their body, but it excited me, too.
My black paying customer picked out a interracial video to play in the booth while we went in the booth for some action. He said out loud, “We will be in the gloryhole booth if anyone is interested.” I wondered what he meant. It would not be long before I found out.
When we entered the booth I noticed it was relatively small with a couple of chairs in it. The porn video was already playing and this hot little blonde was already going down on this black guy with a fucking huge cock. I wondered what I had gotten myself into and wondered if he had a cock like that.
He asked me, “What else do you do and how much does it cost?”
“Anal only and …um…another ten dollars?”
“You are one cheap whore. You don’t have some disease do you?”
“No. No. I am just new at this.”
“Alright whore. Lets see how you suck cock.’
He dropped his pants and sat down on one of the chairs. As his cock flopped out I let out a small gasp. He said, “Is it bigger than you have seen before?” I just shook my head yes, because it was. It was still semi-soft and it was as big and thick as my stepdad’s cock, except the head was bigger.
I dropped to my knees and grabbed the base of his monster cock and started licking and sucking like I knew how. It wasn’t long before his cock stiffened and grew. I could not believe how thick and long this beautiful black cock was. My guess was that it was about eleven inches long and once it hardened was thicker than my stepdad’s cock. I could barely get my hand around it.
I sucked it as best I could, but his big fucking dick really stretched out my mouth. I figured out that I could stroke more with my hands to give his entire dick a great sensation.
After a couple of minutes, he said, “You do know how to suck cock. In fact I would call you an expert.” I was proud that I could please what seemed like an experienced man.
He stood up while keeping his dick and my mouth and moved my head up against the wall. He started fucking my face with his huge pecker. I thought I had my gag reflexes under control by now, but I could not help but gag every time he shoved his big, black cock in my mouth. And no matter how much he shoved, there was leftover cock that did not fit in my mouth.
After about a minute of my mouth being filled with dick and being oxygen deprived, he knocked on the wall and a hard cock stuck through a hole right next to my head. He pulled his cock out of my mouth and said, “Now suck that cock!”
After what I had just been through, this cock would be easy. It was only about six inches. I do have to admit it was exciting sucking a mystery cock with only the cock and balls sticking through a hole.
I immediately went to deep throating this cock furiously. Whoever this was, they were going to get an amazing blowjob.
As I worked that dick I felt the black guy lift my skirt from behind and he ripped off my thong. He rubbed my ass shortly before I felt a lubed finger enter my ass. He said, “Bitch you aren’t super tight, but we will have to loosen you up before you can take my cock.” I completely agreed and kept working the cock that was in front of me.
I could not believe this mystery cock was holding out as long as he was and I felt two more fingers stretch my ass and drive into me. I let out a low moan which must have set off the mystery dick as I felt it swell and shots of cum enter my mouth and the back of my throat. I gladly sucked every drop of cum out of that dick before he pulled it back through the hole, but it was quickly replaced by another cock. It was a black cock, but it was smaller than the other one, only about nine inches. I was so lucky to have my first two black cocks in one day.
As I started sucking on that cock, I felt the other guy get behind me and pour some lube down my crack. I was a little scared as I felt him position his huge cock right at my asshole.
I slowed my cock sucking as he started to press at my ass. His big dickhead was having a hard time pressing into my ass, but he kept a constant pressure as I pressed out with my ass. I felt his head press pass my sphincter muscle as it entered my ass. It was almost a relief because the head was bigger than his cock. It was almost like a buttplug. After I adjusted to his cock head, he slowly started pushing his dick into my ass and I started to suck the cock in my mouth more.
It seemed like his cock went on forever as its length kept pressing in me. And that big cockhead was stretching me and filling me like I had never felt before. He finally stopped pressing and said, “I hit bottom. You almost took it all.
Then he started fucking me. He was slow. He would press in to the bottom and pull all the way out to the head. It felt like my ass was trying to keep his head in. He worked my ass back and forth and it felt great and I worked the cock in my mouth. As he fucked me it felt so good and I started to work both cocks and moan some. I could also feel some precum leaking out of my dick.
It wasn’t long before the black dick in my mouth exploded and gave me another sweet load of cum. I gladly swallowed all of it. His dick was quickly replaced by another.
The monster cock in my as picked up its pace. I could not believe how good it felt to have my ass filled so full. Now I knew what those big fucking dildos were for. We fucked so long I lost track of time. I sucked ten dicks before they quit poking through the hole. I swallowed all but two because those two fuckers pulled back and came on my face and the floor.
When the last one pulled out, the big black dick that was reaming my ass said, “I guess that is it you nasty fucking transvestite. Now lick that extra cum off the floor while a really fuck you. I bent all the way over and started licking the nasty cum off the floor as he fucked me really hard and fast.
My ass must have adjusted because I had been fucked so hard for so long because I could feel his body slamming against my ass as he buried his monster dick in my ass.
It only took a couple of minutes before I heard him grunt, “Uhhh. Take my cum you whore.” I could feel him bury a couple of loads in my ass before he pulled his cock out fast. The head made a slight popping sound and shots of cum hit my ass up my back on my skirt and one shot landed in my hair.
He wiped his dick on my ass, pulled up his pants and said, “Here’s your pay man bitch.” He slapped two tens on the cum on my ass to stick them there and left the booth.
I just laid there, bent over thinking about all the cum I swallowed and how sore my ass was. It was like paradise until the door burst open and two police said, “Get up whore. This is a sting. You are under arrest.”