When I travel, my grandpa house sits for me and watches my fur babies. They just love him. So do I. Now, I always thought grandpa was a pretty straight laced guy. You know the kind. Loves beer, Duck Dynasty and football. This last time I traveled, I came home early and got a huge surprise. My burly grandpa, setting on the couch in my clothes with a Pabst Blue Ribbon in his hand. By clothes I mean my pink bra with matching panties and a black garter and thigh highs. When I said hello, grandpa was really embarrassed. Tried to tell me he lost a bet. I explained to him, that although we are family, there are rules in my household like you do not wear my clothes without permission or without consequences. I told grandpa if he was fond of ladies clothing, well he was going to wear them in public all day long.
He tried to argue with me, apologize, say it was just one time. But, I knew this was not true. When I have returned home before I have had my suspicions based on clothes not fitting right. I told him if he could wear my clothes in my house, he could out and about too. I went and got him a blouse, a skirt and a pink bow. Ordered him to put it on. He kept protesting so I snapped pics of him in my lingerie and said do as I say old man or I send these pics to grandma. He immediately got dressed in my street clothes. Now he didn’t look too hot in them. In fact he looked like a sissy; an out of shape sissy.
I ordered him to take me to the hardware store. I wanted him in my clothes in a manly place. The whole drive he was pleading with me to give up this silly punishment. He was ashamed to enjoy ladies clothing. I told him to embrace his feminine side, to accept the fact that he is a sissy and cross dresser. I reached over and grabbed his crotch and could feel his hard on. I informed him a hard cock on a old fart meant he liked it; that he was enjoying being humiliated. Truckers passed us and honked their horns, waved, some even blew kisses. When we got to Ace Hardware, I instructed him to own it. Walk in chin up, boobs out.
I was so proud of my sissy grandpa. He strutted right in and embraced his femininity. There were some stares, some snickers, but he never showed embarrassment. When we got home, I let grandpa jack off on my big tits. He may be a sissy boy now, but he is still a red blooded good old boy who likes big boobs. Grandpa comes over all the time now and we play dress up. I do his hair, his nails, give him boobs and dress him in something pretty. Maybe I can feminize you too?