Transgender TV, oral, anal, b/MM
This story is a work of fiction and contains descriptions of explicit sexual acts of boys and men discovering their sexuality. It contains graphic scenes of sex between a consenting underage boy and adult males. If this type of content offends you or you are under the age of 18 do not read it.
Copyright 2022 Wolf, all rights reserved.
You may contact me at pomowolf74@gmail.com if you like. All flames will be ignored.
Jimmy is a Sissy Slut
By
Wolf
It was a typical Friday night for me after school. I was playing my video game when my mother was on her phone talking to God only knows who her flavor of the week was. More than likely going to dinner and dancing when I saw her picking out a little black dress and rummaging through her lingerie drawer, so I knew I was going to be home alone that evening.
Just as I suspected a little later, she was putting on her dark self-supporting nylons and her 4-inch stiletto heel black pumps, matching black bra and thong panties before she put on a form fitting little black cocktail dress. She put on lipstick. I smiled knowing she was about to get parted by someone again. It wasn't long before I saw a car pull into the driveway. As she exited the house, she left a ten-dollar bill on the kitchen counter for me to order pizza.
Instead, I went to her room and put on one of her really slutty lingerie sets of lace thong and teddy, before sitting in front of the computer and logged into an AOL chat room planning on stroking my cock while chatting with a man. When I got a chat request by someone identifying as BBC daddy. I was intrigued and started chatting with him and telling him all about myselfand trying to get an idea of what he wanted, finally I told him what I was wearing and that I was home alone, and if he was serious, he could stop by. I gave him the names of the intersection roads and which corner I would be waiting on. He told me that he would be there at 9:00pm.
So, I put on a pair of cargo shorts and a Tee-shirt over the teddy and left the house at 8:45 to walk down the street to the corner and stood under the street light on the southeast corner. I was there within a couple of minutes. Standing there waiting seemed like an eternity, as cars passing slowed down to look at the young preteen. I was getting nervous and butterflies were turning my stomach thinking over thinking that any of them was him. Eventually a car slowed as it approached the corner and as it pulled close to the curb the passenger side window came down electronically and a black man leaned over the console and asked: "Hay, are you waiting for a 'Big Black Cock?"
I smiled and said: "Yaa."
He told me to get in, so I got into the passenger seat and told him to drive east on the street and pointed out the driveway to pull into. When we got out of the car, I saw that he was a mountain of a man well over six-feet-tall. He was a good-looking man in a nice suit and his nappy hair was graying at the temples. Even in the suit I could tell he had an amazing body. His voice was a deep baritone that sounded confident, when he asked me if anyone was home. He was apprehensive since he realized I was much younger than what I had told him, but the bulge in his pants said that he was interested.
I took hold of his massive hand and led him into the house, where his apprehensions went away once I led him to my bedroom and removed my Tee-shirt and cargo shorts, and saw that I was wearing Mom's matching lace teddies and one of her thongs. He immediately smiled and said: "I'm going to have some fun with you!"
When he removed his clothes, I was impressed. I had seen men's cocks that were very impressive before. Some were as much as 8 or 9-inchesb long and very large in diameter, but nothing could've prepared me for the sight of the largest cock I have seen in my life in front of me. My hand could barely wrap around it and it was probably the length of my forearm if not bigger.
Part of me was scared and nervous As I got on my knees and he took over. He was very verbal while having me suck kiss enormous cock while slowly inserting a butt plug into my asshole. He just smiled and he said: "You don't need to worry I will make it fit one way or another!"
He eventually Bent over me and pulled out that butt- plug, and he proceeded to mount me while I lay face down on my bed. He straddled my legs and sat on them as he ran his finger up and down the crack of my ass before he placed his cock in the valley. Then he used his fingers to push down really hard forcing the big mushroom head against my tightly puckered asshole, while telling me to relax as he managed to get the head of his enormous 12-inch cock into my tight asshole and while he pushing down on me while his weight pressed my small body into the mattress. He just kept telling me that I was a good little boy and to enjoy it with each thrust he kept forcing his cock into me, spreading rectum. I was feeling both pleasure and pain from being literally split apart that night. Eventually he got maybe 3/4 of the way into my ass, and I couldn't take any more.
That was when he started humping me mercilessly hard and fast. Just when I thought he was about to cum he quit. He pulled out, leaving a gaping void, while he turned me over onto my back and applied additional lubricant in my asshole. Then he picked up my legs and rolled me up until I was resting on just my shoulders and the back of my neck with my legs dangling over my head. He stood over me and straddled my butt and told me: "look at how I'm making you take my big cock into your little asshole!" I was looking up at the big purple knob with the pink circumcision scar that covered a quarter of the length of the bark black cock that must have been a foot long as he used his finger to stuff the head into my tight little hole. While he was driving his cock into my asshole, he was telling me how good my boy pussy was. He I watched him fucking me and with every thrust he shoved a little more of the shaft into me. Eventually his wiry pubic hair was smashed into my stretched asshole ring. I was amazed that he was able to get all the way into my body. With every thrust it felt like the heads of his cock were poking my belly button. He eventually came in my ass.
When he pulled out and allowed me to uncoil and relax on the bed until we felt recovered. He had me suck his balls and cock until he was hard again. When he was fully erect, he lay back on my bed and picked me up bodily by my waist and placed me over his cock and lined up my asshole with the head of his cock before lowering me and letting my body slide down impaling me on his cock. He started bucking his hips up and down in fact fucking me or you could say I was fucking myself. The whole time he was using me he was calling me slut pussy boy wearing my mother's slutty lingerie, and telling me that when he finished stretching my asshole, I would be spoiled for small cocks forever! After he came in my ass, he lifted me off of his cock. I reached back and felt my asshole and it was gaping open and when I tried to clinch the hole closed, I felt a stabbing pain that forced me to relax the hole.
He told me that my sphincter would relax and return to normal, but it would be sore for a day or so. I lay on the bed and watched him get dressed and he promised that anytime I wanted to see him again that I could email him or give him a call.
I fell asleep reliving the nights events and was woken from a deep sleep by my mother and her latest cock come stumbling up the hall to her bedroom. There was no mistaking what they were going as I listened to the headboard banging against the wall.
If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to pomowolf74@gmail.com