Every Tuesday, Thursday and sometimes on a Friday too, I meet Justin who's now twenty, at a motel and fuck the shit out of him. He brings along a short tight dress, lingerie a variety of wigs and make up. And is usually ready for me when I arrive.
It's easy for me to explian to my wife why I'm a little late on those particular days, as I have to drive over to another town during my work pattern. What she doesn't know, is I leave early so I can meet up with Justin, a very convincing cross dresser, who's very soon to become a shemale after his breast enhancement.
I first fucked him during a work seminar in a hotel, he was a waiter at. He caught me staring at his tight ass, and asked me if I'd like to fuck a horny slut. Twenty minutes later I was balls deep up his glorious asshole, in an empty guest room.
After fucking him for some considerable time, making him cum without touching himself, then cumming all over his cute face, he told me he enjoyed dressing up as female and was saving for a "Tit job" as he put it.
From then on I paid for the cheap motel room and gave him a little money to his "Tit fund". In a months time he'll be having the procedure to enhance his breasts. Something I'm looking forward to as I've been having him stuff his bra's with socks.
I have to tell you when he's dressed up, he's such a beautiful young thing. Only he has a large cock, a delightfully tight asshole and stunning looks which drive me wild when I fucking him.
last Friday as I was fucking him from behind, lifting his short flowing skirt over his back, Justin told his new name after his operation will be Jessica. He doesn't know it because I've never mentioned it, that my wife's name is Jessica.