Chap 1: Intro
First and foremost this is a true story to how I remember it. For years, about 2-3, I crossdressed in private with my mother's wardrobe. Eventually I was able to build my own through stealing items of clothing from my work, I worked at a thrift store and accepted donations. Within months I had an a brimming wardrobe of my own. Eventually a wardrobe wasn’t enough and I worked up the courage to stop at my local Adult Bookstore. More time passed and my new toys weren’t enough so I exposed myself on ImageFap and did light cam-2-cam play…..it wasn’t enough. So my mind turned towards Craigslist where I spent months debating and arguing to myself if I should do it and even more time searching for the right one. Then 2 weeks ago I found him.
Chap 2: The Invitation
His ad was simple and straightforward, he wanted a young person, male or female, to suck his dick. He was a 62 year old black man with a 10in cock. He didn’t want roleplay, back and forth, just a mouth on his cock. I replied explaining I’m a virgin to cock and a non-pass crossdresser who just wants to suck a cock for the first time but since I’m shy I just want someone who will sit back and let me suck cock with as little verbal communication as possible. He was fine with all of it. His reply was when and where we should meet. I set the time and date, my place, middle of the week early in the morning, right after both my parents would be at work as well as my neighbors. Tomorrow was my day.
Chap 3: The Set-Up
I awoke early and spent an hour getting ready. I took a shower and shaved my face smooth. I chose my wardrobe for the occasion. I went with my bright long red haired wig as it made me more passable by covering some of my face. I then chose my tightest bra to give the appearance of a woman’s chest. I found a pair of panties that went with the bra that had a nice rose pattern to it. With my matching undergarments I chose my simple long sleeved PINK shirt and black skirt that went down to my knees. With roughly 10mins before he was suppose to be their I set-up where I was going to be sucking his cock. I first put on some porn I found in my parents closet, BBC for white teens, how appropriate. I then got my knee pillow and some towels. I placed one on the couch and the other on my pillow. I took a step back to gaze at my set-up but was soon interrupted as the doorbell rang, it was time.
Chap 4: Arrival
I approached the door, I peered through the peep hole. Their he was standing. A tall, thin as bones 52 year old blackman, his hair grey as grey can be. He was no stud but I’m not looking for prince charming, my interest in man is strictly with cock, and he had 10 inches of one. I opened the door, he looked me up and down then nodded. I motioned to come inside, as he came in he looked at my set up, the towels and pillow were he’d be getting sucked off, right across from the flat screen were some tiny white girl was being fucked by a thug with a big black cock. I could see a small smile draw to his face. He then went to were I would suck his cock and started to undress. As he did so I started to doubt he actually had a monster in his pants as he looked like a skeleton with skin on him. Then he dropped his pants and their it HUNG. All promised 10 inches of black meat. It looked like it belonged on one of the pornstars in the video on screen and not this old timer, honestly it was thicker than his wrist. He then sat down as I stared in awe and started playing with himself, eventually looking at me and giving me a nod. It was my time.
Chap 5: The Cock(Sex)
So there I was on my knees. A crossdressing virgin staring at a 10 inch black cock. I took a light grip at the base of his cock to hold it up. I then used my other hand to guide the head of his cock to my mouth. As my tongue made contact with the thick head of his cock it was over, i was no longer a sissy virgin. I rolled my tongue around the head of his cock. Wrapping my lips around the tip, still working the head with my tongue. I lowered my mouth down onto the cock, taking more and more of his shaft as I bobbed my head up and down. I was taking my time working his cock, completely in my own world of sissy blissfulness. I could hear him grunting in approval at my work. I noticed the grunting stopped and he tapped me on my shoulder to get my attention, when I looked up at him he pointed at the TV. I turned to see a big dicked black man choking out the little white girl with his big cock on screen. When I turned back to him he was smiling and I nodded. I went back to sucking his cock, ready to work my way to deepthroating his meat, it was then we had a misunderstanding as I felt both his hands on the back of my head. He then shoved me down and all of a sudden I had all 10 inches of his cock down my throat. It didn’t stop there, for an old scrawny man he had tremendous strength as he moved my head back and forth as he skull fucked me. And I let him. I was gasping for breath, tears running down my face, and I couldn’t help but just sit there and take it. Every so often he let me breath than grab his cock and slap my face with it. As he fucked my mouth I could hear his mumblings “Take it you white bitch”. And take it I did. He degrade me, made me suck his balls, choke me with his cock, slapped with his meat, and called me a bitch. And I couldn’t have been happier. I had no idea of how much time had passed but he shoved me off his cock to the ground as he stood up and furiously beat his cock. With one hand still beating away he reached down and lightly grabbed my throat and pulled me up to receive my reward. I sat their staring at his cock, my mouth opened wide and then it hit me. He unloaded his hot thick creamy cum all over my face, the first couple shots blinded me and the rest filled my mouth. I sat there stunned and delighted at my current state. He slide his cock in my mouth a couple more times then slapped me with his cock a couple more times before walking away for a bit. A couple of minute later a towel hit me in the face and he placed something my mouth. As I wiped my face I heard him open and close my front door, once I had my vision back I spit out what was in my mouth, in my hand was a crumpled piece of paper with cum on it from my mouth. I unraveled it, on it was a phone number with the sentence “next time anal”. I couldn't be more excited.
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