1. When dressed


    Date: 8/24/2015, Categories: BDSM, Fetish, Author: klammer, Rating: 100, Source: xHamster

    and my Mistress taking my ass every day with a strap on excites me. I would very likely soon regret it, but I am sure I would beg her to keep my tiny cock locked, fuck me with a strap on every day until she cums and keep doing it for as long as it takes until I cum, still caged, while being fucked. I have no idea how long it would take. I am sure it would be weeks, could possibly be well over a month. Wouldn’t matter. Once my Mistress laughingly agreed the choice would no longer be mine. I am sure that after the first few days or week my ass would be perpetually sore. Every day I would bend over, get on my hands and knees, or assume some other very submissive position and offer up my ass to my Mistress. It started with a couple of fingers up my ass when she was sucking my cock. Soon I was wearing a butt plug around the house. Next I had to wear it anytime I was given an orgasm. From there is was a small step for my girlfriend to strap on a dildo and be the one who does the fucking in the relationship. From the first day that she bent me over the bed and fucked my ass until she came I have not been allowed in her. When I saw her new strap on I actually begged her not to use it. It wasn’t the width, I knew I could take that, it was the length. It was easily twice as long as anything she had used on me before. I never thought I could take something that long inside me. She laughed. Told me that she wanted to hear me squeal. Told me she would get all of it up deep inside my ...
    ass. As I took off my clothes and bent over the bed I was certain that soon she would make me squeal. I was pretty sure before she was done she would make me cry. Somehow I was beginning to think she wouldn’t mind that either. My Mistress was displeased. She had been feminizing me for years, and recently had given me to one of her friends to suck his cock. The report back was not favorable. As she watched me put on the clothes she laid out she told me this evening would be dedicated to cock sucking training. She would not have me embarrassing her any longer. Mistress had me wearing a tight crop top with no bra or fake breasts, stockings, garters, heels, sheer panties and my shortest skirt. She clearly was openly advertising that I was a sissy male and a slut. Smiling she took me out and brought me to a Jamaican Pub in a not good part of town. As we walked in she told me that I was to challenge every man there to a game of pool. I did not realize what the penalty was for losing, but Mistress was well aware of it. I am very bad at pool. It was not long at all and I was on my knees on the floor of the bar with a large black cock in my mouth as the other patrons watched. The rest of the night was filled with quick games of pool then on my knees sucking long hard cocks. Somewhere around the fourth or fifth cock my panties had been pulled off. I never found who had done it and never got them back. A souvenir for someone I guess. I still had to play every man in the bar, knowing I was ...
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