1. SissyMandy - Insatiable Little Me


    Date: 8/1/2024, Categories: Cross-dressing, Author: Jilluvscox

    ... tight embrace as his talented fingers and tongue give me the bestest orgasm I could have ever imagined.
    
    "God…" I pant as Max swallows my sissy load, "I wish I knew how to do that for a man."
    
    "It's a special skill your Mistress wants you to learn before we send you back to her."
    
    "So you're gonna teach me?"
    
    "That's why you're here, babe," Rob says as he forces me to my knees. "Brenda wants you learning about everything men do with other men."
    
    Rob then widens his stance as Max begins teaching me the art of prostate massage. It's a little weird at first sticking my middle finger up Rob's ass, but he seems to like it as much as I do. I start giggling as I probe around to locate his walnut-sized pleasure spot, but it's not all that hard to find with Max guiding me to where it is.
    
    When I'm somewhat comfortable with it, Rob slaps his cock across my face a few times before shoving it down my throat. Since we all have the same anatomy, Max then sticks his finger back up my sissy ass, massaging my spot again so I can simultaneously feel the same sensations Rob's feeling as I'm learning all the cool techniques.
    
    Max is a great coach, and I'm so excited he's teaching me this erotic new thing I can do with men and other sissies. It's mind blowing to finger-fuck Rob as he fucks my throat, and when he orgasms a second time this morning, I get a hands-free sissygasm as his cum seeps into my belly!
    
    Fuck… that was the most totally gay thing I've ever done, but I loved ...
    ... everything about it, and I'm learning so many fascinating things about our male sexuality that a female Mistress could never teach me. At times I was even wondering if maybe things would escalate to the point where they'd want to pee on me like Brenda and Virginia do in our shower.
    
    It was a weird thought, because even though I love doing it with women, I don't know if I'd like it so much with men. I'm glad they didn't make me find out.
    
    ~~~~~
    
    Once we're out of the shower and all cleaned up, I'm looking through my suitcase, deciding what I want to wear for them today. Max has to work from eleven to seven o'clock tonight, so we're going out to eat, then Rob's taking me to see the sites around Carmel after that.
    
    It's foggy outside and rather cool, so I'll be wearing cotton thigh-high sissy socks to keep my legs warm. I'd rather have my skinny legs covered in public anyway, at least until I get more meat on my thighs as I'm developing my fat sissy ass.
    
    Now that my breasts are growing and the hormones have changed my psyche to that of a girl, I've become very conscience about my appearance. I'm taking extra care putting on my makeup, cuz I want to look hot and sexy, but at the same time, not over do it like I've often done at home.
    
    All the hours that Brenda and Sherry have spent teaching me about makeup are paying off now as I do my own makeup on my very first weekend date with men.
    
    ~~~~~
    
    We take separate cars into Carmel, and I'm tempted to suck Rob's cock on ...
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