Letters From A Sissy Cuckold

Good Morning, Mistress,

I just wanted to relate our most recent foray into chastity and humiliation. I was off yesterday so S made sure to lock me into her cb3000 before she left for work. She wanted to make sure that I didn’t waste my day touching myself. So I did my honey-do list as required and she was very happy with my work. She had a business meeting that she had to attend with several of her peers and she looked absolutely gorgeous in her black A-line skirt and white tailored oxford. She left for the meeting and needless to say I was feeling the pinch as my cock strained in its prison. In her meeting there was several men and women but one of which she is quite fond. She had worked with him before and had repeatedly talked about how handsome he is. Anyway, as I’m at home watching the news she texted me and told me to go look at the bed and I did. When I got there I texted her back asking if she had taken her panties off before going to her meeting. She responded that she had and that she was soaking wet looking at her handsome muse. God I got hard as a rock! She teased me a little bit more by saying that she saw the outline of his bulge when he walked in and he was very large, this only furthered my humiliation as I sat in my chastity prison.

When she got home the fun continued. She got the Kept-for-Her dildo attachment for my cage and affixed it to the ring around the base of my balls and then led me to the living room where she grabbed the computer. When attached the dildo is much larger than I am and I was somewhat embarrassed by the whole thing. She lifted her skirt and backed up to me while I was on the sofa. She opened her legs and straddled my lap and slowly lowered herself onto the dildo. As she did she said, “Wow, now THAT is a cock!” She told me that she was sure that the phallus in her was about the same size as she imagined her friend’s to be as she fucked herself to several orgasms. I was well and truly almost crying from frustration at this point.

When she was done she turned and kissed me and thanked me for letting him fuck her so well. How humiliating! She then finished undressing and she led me into the bedroom. I was sure that I was going to be allowed to fuck her at this point but she had a surprise for me. She handed me a little gift bag and I opened it to find a Fleshlight that looked like a pussy! She released her cock from the prison and told me that I could fuck the fake pussy while she watched! I begged her to let me inside of her but she was firm that that wasn’t going to happen for a while and that if I wanted to feel a pussy that my little cock better get used to the fake one! I was so humiliated!. She sat on the edge of the bed while I knelt in front of her and stroked myself to orgasm with the Fleshlight feeling completely useless. When I was done she had me reattach her cage to her cock and we went to bed.

I don’t know what came over her last night but I loved it and hated it all at the same time. Maybe a case of be careful what you wish for!