1. A Virtuous Reality


    Date: 7/6/2024, Categories: Transgender & Crossdressers, Author: byA_Boring_Writer

    ... fit but meeting an airtight blockade against her...
    
    She needed him to relax even more...
    
    "Liam... I need you to loosen up for Mommy, okay? It's going to hurt quite a bit but I promise you'll feel better in a minute or two... Just... Take a deep breath..." Viv spoke gently to him, a partial ruse as she fought off every urge to just force her way in... She was serious that she didn't want to break him... She wanted him to enjoy this too...
    
    Liam paused as he calmed himself down, Vivenne watching his body rise as he inhaled a full lung's worth of air... She felt his button relax... his body softened under her... and with a good amount of pressure applied...
    
    Pop!
    
    She felt his body clamp down around her tip like it was trying to strangle it blue, the intense bolt of pain making Liam gasp with heart-stopping agony... She didn't move... She let Liam bite down on the pillow, muffled squeals erupting from it as she gave him time to adjust... It felt like sticking a metal rod into a burning forge, the red hot tip searing with heat and pain through his gentle, inexperienced muscles...
    
    He wasn't a stranger to anal play, but this... this was inhuman...
    
    He knew how big she was before all of this... He thought he could handle it... He thought the pain wouldn't be that bad... If it was this excruciating with her numbing gel and a condom, he could only shudder at the thought of taking her raw...
    
    A few moments passed...
    
    He felt the nerve endings cool, the shock ...
    ... wearing off as his beautiful mother let herself marinate... He took another deep breath, holding back tears as his teeth stayed clamped to the padding underneath him... Vivienne could feel him start to relax again, giving him a proud smile as she waited a few moments more...
    
    She felt the path clear slightly, letting herself sink a bit further, feeling an inch and a half disappear inside his restricted opening...
    
    She could feel him tense again... Fighting her... Resisting her... It was the tightest thing she had ever felt... She was getting impatient, but she had to give him as much time as he needed... She felt him open up to her as she plunged forward, another few inches managing to fit into him before she hit another wall...
    
    That was as deep as she could go, holding almost six inches in him before reaching the inner wall of his intestines... This younger generation was a bit too shallow for her tastes... Her dominating instincts goading her into taunting him...
    
    "Oh my... Only halfway in and I'm already hitting your limit...? I expected my son to have more well-endowed friends to hollow him out a bit, but I guess I don't mind catching you up to your peers." Viv's eyes could have glowed red from the amount of evil intent behind them, Liam shutting his own eyes even tighter as he waited for the hardest part to begin...
    
    She tried applying another small coat of lube directly to his hole first, gripping her son's waist as she pushed forward with most of her strength... ...
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