Probably the most humiliating I've done was with a former cuck that had fully embraced cissification - he had a maid's outfit, complete with fishnet stockings and suspenders, high heels, and a blond wig...cuck72 said:My wife watching not only her bull making me get on my knees and suck his cock, BUT THEN! have me lick his asshole in front of her. To just think of my wife so disgusted losing all respect for me, and looking at her lovers as the real men and me a disgusting shithole licking faggot.
After resisting longer than is normally the case, eventually the wife succumbed and I took her anal cherry - when I'd finished, I told the cuck to clean it up... rather than lapping up her ass, he sucked my cock clean first! At our next meeting, he pleaded with me to take his anal cherry, which (although not a fan of M-on-M) I did - he then cleaned me up again.
My job there was complete......