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Yeah I have before, I was fucking him so hard with the strap-on that it fell out of the harness and stayed in his pussy.

Love stretching out my sissy cuck's pussy 🤤

I have been working on my sissy husband for a little over a year now. Started slow, bought him a cage a week before our wedding, made him wear it for three days straight including our wedding day. It was so hot knowing he was caged under his clothes. That night I bought him an anal trainer kit...

It's not his first cock, but first time taking a load 😉

It really was!

We met a guy who had come to our house to try to sell us something. Well flash fwd after fisting my bi cucked husband and trying to fist our new friend. We decided to go over to his house last weekend where they both were wearing sissy panties, I made my husband suck his cock, while I fucked him...