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Chapter 33 by gemmaxoxo gemmaxoxo

What's next?

Let's go!

Gemma's first challenge is the sheer circumference of the dildo. It's the thickest object she's ever attempted to mount. Even the gigantic anal beads that she had so much trouble with at the start of your journey were only half the size, although she has since graduated to bigger and better things. It takes her several attempts, sitting on the massive rubber cock and trying to ease herself down until finally, she's able to press the tip through her sphincter and take the first two or three inches inside her ass.

"A-a..ah... I can't," she whimpers, unable to go down any further. She's panting hard, and beads of sweat have already begun to form on her forehead.

"Yes you can, baby," you say, getting up from the chair and walking over to her. "Just relax."

You slide your cock into her mouth and down her throat, and the familiar feeling of your shaft between her lips seems to send her into a trance, relaxing her body as you smoothly and carefully slide your cock in and out. You watch as slowly her ass slides down the shaft of the enormous dildo, stopping every few inches for her to grow accustomed to the size until after about five minutes the entire thing is inside of her. The last portion is the most difficult part, where the dildo flares out to an even greater thickness, but she managed to get it all the way down until she's practically sitting on the floor.

At this point she's struggling to hold it inside of her, her face grimacing as she stares up at you with your cock in her mouth, but you also detect a hint of pleasure in her eyes as her eyelids flutter. You can't imagine how full she feels, with her guts sandwiched between the dildo from the bottom and your cock from the top.

What's next?

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