Although I’ve been very busy with my Niteflirt Phonesex callers, I have managed to continue “initiating” my new little subbie into the world of cuckolding. The other day, I finally introduced him to my strap-on. Sure, he was a little nervous…but he willingly got down on his hands and knees for me while my stud boyfriend sat back and watched. And, just for the record, yes, I was nice and gentle and even got out the lube for his first foray into strap-on sex. I wanted him nice and ready for my boyfriend’s thick cock…he just loves “fresh meat”. Oh, the gasp my little panty-boy let out when I finally penetrated that tight little ass of his! I reached down and, of course, his puny dick was rock hard! Just the touch of my hand and the hard cock in his puckered hole was almost enough to make him shoot his pathetic little load…so I took it nice and slow…at first. You and I both know that most men would never admit that they love the feel of a cock in their asses…but in no time, my little sissy boy was practically begging for the real thing! I got to sit back and let my stud take over…and he was no where near as gentle as I had been! Sissy did an excellent job for his first time…so I actually permitted him to cum that day! He was sooooo grateful!! And you all thought Mistress Tasha was so cold hearted! I always reward good behavior, as so many of my regular Niteflirt Phonesex callers know!