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How Many Inches Can My Sweet Sissy Take?

 

 

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She was a lovely as ever…

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Kneeling before me in her pressed white petticoat, lacy gloves adorning her delicately folded hands, resting on her lap.
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Her hastily applied lipstick was a gorgeous shade of coral, painted on with a trembling hand, it glowed quite beautifully against her otherwise peachy completion. My sweet little sissy slut, Lolita. A name chosen so appropriate, barely 28, but with such a lovely and wicked sense of innocence about her.
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She had brought me a gift today – stopping off at Lovers before making her way to the dungeon. I can only imagine how anxious she must have been, no doubt a bit hurried in her choice in item, she grabbed what looked the most exciting and squirreled away to the cash register with barely a second discerning look at what she held in her hands.
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I kept her kneeling in front of me as I unfolded the box, removing the plastic layers and gleefully pulling out one of the LARGEST double sided dildos I’ve ever seen. “Bigger is better I suppose”, I mocked in her direction, holding the entire length of it in front of her…Honestly, even I was surprised by the size of it; how on earth could any one possibly handle this?
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“A double sided dildo – this has certain implications, don’t you think, my dear?”
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I could see her straining to catch my drift, not one for buying toys herself, this really just wasn’t clicking into place. I think perhaps that virginal sense was what I enjoyed most about her. So eager, yet so very new to nearly everything dark and erotic.
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“Typically, it’s used with a partner – to penetrate to waiting orifices in tandem”, I raised an eyebrow to her.
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It made me grin as the rush of panic flooded over her face, explaining so quickly that she tripped over her words; she’d NEVER imply that *I* should be the recipient of one end of the stick, so to speak.
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I kept my face as still as possible, making it impossible to read my emotion while she continued to fall over herself in this seemingly unending apology. A part of me wanted it to last forever, I soaked in her anxiety and embarrassment like a drug before finally holding a finger to her lips – “we will use it darling, well…YOU will, and I think I have just the method in mind.”
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I began waving the long black glistening sheath in front of her, tempted to strike her cheek with it a bit or knock her lovely little body around with this oversized appendage. “Since you are such a size queen today, I’ll give you an opportunity to redeem yourself.”
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She sat up a little taller, listening intently…
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“You will suck this big cock as deep down your pretty little mouth as you can. I’ll give you 10 minutes to try to deep throat it and wherever along this dildo you leave the farthest coral lipstick impression – that’s where I’ll take my measurement.”
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“The rest of it, you’ll be taking in the ass….look at it this way, you’ll effectively be kissing your own ass when I’m done with you.”
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She was so uneasy, sizing up the tremendous length and girth as she brought her mouth forward, fitting her soft lips around the giant rubber cock without hesitation. I have to say it was the most eager and diligent blow job I’ve ever seen someone give to an entirely unnatural and unrealistic cock, but with what was at risk – I couldn’t blame her.
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With all of her efforts, the sore jaw and thin layer of drool running down her chin, she was only able to get 4 inches of the entire 13 down her throat. Such a pity.
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I ordered her to her back, legs in the air, I cuffed her ankles up high into my suspension rig. Perhaps I pulled them a little higher and wider than I needed for our purposes, but I found her painful spread incredibly erotic through the see of ruffles and lace that made up her dress.
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The dark rubber was lubed up slowly, I made sure to stay in her line of sight as I prepared it, inch by inch, adding more and more slick silicone to ease what would be a very full insertion.
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She made a very vain and short lived attempt at squirming beneath the restraints a I lined up the tip against her nervous nether regions, forcing the toy in slowly and gently.  Her eyes were locked to mine, no doubt waiting for me to push with a bit more force as I filled her up! At 5 inches, her strain to accommodate was visible, goosbumps covering her head to toe, and all color draining from her face as her pulse was redirected elsewhere.
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Inches 6 and 7 brought loud moans of painful pleasure, I began rocking the toy in and out – forcing her to repeatedly accept every inch over and over, reminding her of the consequence of her lack luster suck job. It’s moments like this that I’m exceedingly glad to have a soundproof dungeon – I made her to take the remaining bit. 9 inches slammed in and out of her – leaving a coral ring of lipstick against her  tight little ass. She started panting and straining as I continued, teasing her by asking if she liked “kissing her own ass”.
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Somehow, I wasn’t surprised when she screamed and began thrusting back ‘I love it’; her sweet tone is still echoing off my walls and in my mind. I guess from now on she’ll be more careful about when gifts she brings to my doorstep, but then again, maybe not.

3 thoughts on “How Many Inches Can My Sweet Sissy Take?

  1. I have never had sissy desires before, but this entry spoke to me! Maybe someday if I grow a pair and get to visit you, I can be lucky enough to experience the same treatment!

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