A Roleplay Gone Awry
Chapter 1

Copyright© 2014 by Ronald81

BDSM Sex Story: Chapter 1 - What was supposed to be a prank against a dorky girl within a game changes the "cool" guy forever

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Consensual   CrossDressing   True Story   BDSM   FemaleDom   Humiliation  

For as long as I can remember, I have always been into cross-dressing as a young boy. Yet, I would hide these feelings deep down as I grew up. The following story is partly true, as much as I can remember.

It all started when I was playing a roleplaying game featuring a text based game that was supposed to be medieval in nature. While I was typically a shy, somewhat submissive guy in the real world, it was very different within this game setting. In this game, I would be a fearsome warrior who had the respect of most of the characters within the world. There was a time when I was on the forum with some friends and we'd pick on many people. I could feel that it was wrong to consistently pick on people within the game and yet some part of me as the character would thoroughly enjoy it. There was one character that we picked named Laura (name changed to keep her identity secure, just in case). Laura was an odd ball and I believe even she knew it. But something I didn't know was how proud her character was. On the forum with my friends, I mentioned how I'd catch her in something really embarrassing and post it for all to see!

Laura had always respected my character as a fearsome warrior, but when I was alone with her in her text based home, I was very different. I don't know why, but I confided in her my fantasies of cross-dressing and female domination. She took it all in and nodded and at that moment, she smirked. That smirk that I would see so often, yet is still vivid in my memory to this day. She explained to me what I already knew - that I was some respectable character in this game, yet here I was in front of her explaining to her how I was this bitch boy. I was absolutely stunned to see her reaction since no one ever called me anything as crude as that. And yet, this turned me on and I would tell her that. She did tell me that this idea was very kinky. I was absolutely floored by this whole ordeal. All of this scenario about how I was going to try to embarrass her and yet here I was ... It was surreal! Laura would ask me what I envisioned myself when I was cross-dressing and I told her I would be either in a cheerleading outfit or a maid outfit. What I told her next was something I thought I would never reveal - how I've always had a fantasy about a hot woman such as herself to wear a strap-on and dominate me. She smiled at me and told me to give her a few days to take this all in. I was surprised how much she loved these ideas and I smiled that she was happy to accept all of this.

A few days past and Laura invited me back in her in-game home. Hi Laura, I said to her. Her character slapped me hard in the face and I wobbled and fell over. Laura instructed that I was only to speak when spoken to and to kneel in front of her presence at all times. She set the ground rules of also calling her Mistress or Mistress Laura. Instantly, I got on my knees in front of this goddess. Laura spoke confidently, "Very good slut. Now rise and strip off all those clothes and put on the clothes laid out for you on the bed." I took off my shirt, pulled off my pants and dropped all of my gear onto her floor. She smirked and asked me, "How big is your penis?" I dropped my gaze to the floor and bit my lip slightly, then reluctantly told her "My penis is about 4 and a half inches, Mistress Laura." She shook her head and smiled at me. "Yeah, I figured you had a little dicklet. Now hurry up and put on the clothes on the bed, bitch boy." It was hard to contain myself from all her verbal abuse and I looked over on the bed to see a pair of pink panties with a beautiful embroidery of a heart stitched in it. Also on the bed was a short red flowing skirt and white camisole. Even though it was just a game, I could seemingly feel through the screen how soft and delicate the fabric was.

Quickly, I hurried back to a kneeling position in front of Mistress Laura and put my gaze on the floor. "How does that feel sissy?" I responded back to her in a soft tone, "It feels like a dream, Mistress, thank you." I could hear her take something out of her bag and she handed it to me. I held onto it and noticed it was a big ebony dildo! "You always wanted to be a sissy slut, so now is your chance. But, I want you to first crawl over to the window so anyone can see how big of a whore you are." This was my first experience with BDSM, but I followed Mistress Laura's command completely. I could feel the shame as I crawled on my hands and knees with the dildo in hand as I looked out the window, seeing all the passerby characters in the game. They had to only look into Mistress Laura's window to see me in this predicament! "Now bitch boy, I know you aren't used to this since you have a little sissy dicklet, but what you are holding in your hand is what a REAL woman like me gets from REAL men. So do what you were born to do and suck that cock!" I was both excited from the humiliation and scared being the first time I was doing this and didn't want to disappoint my mistress.

I took the big black dildo cockhead in my mouth and swirled my tongue around it, moaning with excitement. I envisioned I was a porn starlet and wanted to please my mistress greatly. I took the dildo out of my mouth and slurped and suckled along the black shaft. Mistress Laura laughed at my eagerness to suck and encouraged me to look slap that saliva coated dildo on my face and tongue while keeping a constant look outside the window. She lifted my short flowing red skirt so that it was above my waist, exposing my large round butt and hardened penis poking my delicate pink panties. She teasingly flicked and ridiculed my little penis and marble sized balls. Smirking, she shook her head and spanked my bubble butt repeatedly as she hurled demeaning insults at me such as "slut boy, bitch boy, sissy bitch, cocksucker."

I continued to suck up and down the big black dildo, as my eyes welled up with tears rolling down my cheek. Whimpering and moaning like a bitch in heat. Gagging and sliding the shaft down my throat. Mistress Laura was back behind me and while I couldn't tell what she was doing, I could hear some noise. "I've got a surprise for you, bitch, and it's your lucky day!" I had no idea what was going on, but I felt my panties peeled over to the side of my round ass as I felt a penis very similar to the dildo I was sucking. It was lubricated and had an incredibly large cockhead as I felt it press against my ass. Slowly I could feel the shaft slide into my ass as I whimpered with a big black dildo securely in my horny mouth. "Smile as you suck on that cock while I fuck you with my big black strapon dick, my dirty little whore!" My little cock within my pink panties was dripping pre-cum, leaving a wet stain over the delicate panties. I smiled happily while sucking up and down on the black shaft as I felt like a new person who had been hidden was now revealed. Mistress Laura smacked my ass as she pounded away any remnant of masculinity that happened to still be miraculously within me. "Now back that soft candy ass back onto my big black cock, bitch!" I eagerly pushed back to meet her incoming thrusts, feeling every inch of her shaft until I could feel her plastic balls hit my tush. "Who owns this bitch ass now?" Mistress Laura exclaimed loudly. Taking the cock out of my mouth briefly, I yelled back in excitement - "You own this bitch ass now, Mistress!" Her cockhead hitting deep inside me with all her verbal humiliation and me sucking this beautiful cock while anyone could "catch" me at any moment was too much for me as I sputtered ropes of cum all over my new pink panties, soaking them completely.

Mistress Laura just laughed at my predicament and smirked. "Whores like you wet their panties at the sight of my cock." I moaned in content and she withdrew her thick, black strap-on out of my ass. Leaving me on her floor feeling like a cheap slut, I knew this was only the beginning of a huge new adventure for us.

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