Judd is bigger that I expected, well over six feet, bald and bulky, deep voice, a really butch guy. We'd met on the phone in reponse to my ad. Now we were sitting in a booth at a truck stop nursing coffees. Usually he's a mechanic but today he's driving a truck to make overtime. I'd arrived first. Even though we'd never met, I recognised him when he walked through the doors. A big guy like I said with a masculine stride. He looks at me across the table and tells me he'd never do what Bruce Jenner did but he admires him. I know because Judd has told me but no one would guess that under his working man's thick plaid shirt and grubby jeans, he's wearing a bra and a thong like always. He's worn women's underwear exclusively for 15 years because there's nothing like the sexy feeling it gives him. He loves the thong because of the way it fits tightly between his buttocks against his asshole, rubbing against it when he walks. I ask him if his chest is hairy and he nods. I wouldn't want a woman to have hairy breasts but I love it in a guy, running my hand over his tits and feeling the crinkly hair between my fingers. I'm feeling my cock stir in my boxers and I suggest we drive while I can still stand up and walk to his truck. I'm in a hurry to see him nude and to touch him. There's a quarry a few miles further on where we can be undisturbed. We get out of the cab for him to undress. He takes off his shirt and there's a certain feminine grace in the way he undoes his black bra and shrugs it free of his tits. He's obviously studied the way women do it. He tells me the bra was specially made and fitted for him. His tits are beautiful, well rounded and slightly saggy with largeish nipples and a thick covering of dark hair. He makes a sharp intake of hair when I reach out to caress them. I like that, he tells me. There's a hesitation when I want him to take the thong off. When he does shyly pull it down, I see why; he has a tiny cock, scarcely bigger than a small boy's. Fully nude now except for his boots, he relaxes and doesn't object when I take his cock in my hand. I masturbate him standing up using my forefingers and thumb only because even hard he's too small to take in my palm. He gives himself to me like a woman, yielding to my hand in a way that's feminine without being effeminate. He cums, sighs and says he is now my bitch. He needs to get back on the road to make his deliveries and drives me back to the truck stop where I left my car. We arrange to meet again and he leans from the cab window before driving off to thank me for wanking him. It was nice, he says.