jamieinpanties: Recently, I watched a video of a very beautiful transwoman, wearing an absolutely ti
jamieinpanties: Recently, I watched a video of a very beautiful transwoman, wearing an absolutely tiny chastity cage and panties, put on a strap-on dildo and peg a pretty, lingerie-wearing crossdresser… and, it really did something for me. I had also seen a video of a crossdresser in chastity, stroking a strap-on like it’s their own cock, and actually cumming! I wanted to try that for myself…so I did. I had already been in chastity since Monday (daytime only, ~14 hours per day) so I was ready to explode! I inserted a prostate massager into my ass, and picked out my biggest, most realistic dildo. It’s way bigger than my actual penis - a full 9 inches long, and thick. My own is a bit over 5 inches at best (and 1.75 inches in its cage) so the dildo was a major upgrade. I put it in the harness and slipped in, adjusting the straps. The base of the dildo sat over the locking mechanism of the cage and was snug without pinching. I looked down at this beast of a cock; I could wrap both my hands around it and it still extended further. I put on some porn, including the video I had enjoyed so much. I squirted a big dollop of thick lube on the tip of the dildo and used one hand to spread it up and down the shaft… then began stroking my new, rubber cock in time to the porn. I turned on the prostate massager, and set it vibrating on a wave pattern. When they got to the part where the girl in chastity starting fucking her partner with her strap-on, I grabbed my fleshlight, and lubed it up, and started fucking it with my huge dildo. It stretched out that sleeve like I had never done before, nearly hitting the back of it. I felt almost nothing, just a repetitive push on the lock of my cage. The vibration of the massager had me dripping precum, but there was no way I would cum like this. My cock was straining in its cage, dripping and aching. My hips thrusting a giant, slicked-up dildo into a fake pussy, feeling none of it for myself. Happy Locktober! -- source link
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