Niteflirt Phone Sex Cuckolds

I’m sure you’ve all been wondering how things are going with my new sweet panty boy.  Well, yesterday, I decided to take him shopping!  Of course, he’s been wearing lacey panties since day one, but I really needed to complete his new transformation.  He was so excited when we arrived at the lingerie department!  You should have seen the tiny little bulge his teenie weenie made in his pants as he carressed all of those delicate materials!  I found him a few matching bra and panty sets…bright pink, lavendar, black and, of course, a nice slutty red.  We went on to buy plenty of thigh highs with lacey tops (so sexy), a few short shirts, and some little little low-cut sweaters and blouses (even one that shows of his tummy!).  But my favorite was shoe shopping!  I had made sissy boy wear pantyhose under his trousers, so he was already to slip his feet into the high stiletto heels I was picking out for him.  We chose a few different pairs…some nice sensible pumps, strappy sandles…and I wish you all could have seen him trying to walk in them in the shoe store!  Of course, everyone was watching…which had my sissy the brightest shade of red!  It was all very amusing! 

So…today, we began our walking lessons.  I allowed him to choose which pair to practice in.  He’s been stumbling around the house, tending to my needs and whims all day in his red patent leather pumps.  I know his poor little feet must be killing him!  But I told him he has to wear them all day!  Practice makes perfect!  I can’t wait to dress him up for tonight!  My boyfriend and a few of his buddies are all visiting…and I want my sweet little panty boy to be all ready for them!  I can’t wait to see him in all of his finery, a cock in one hand, his mouth on another….  I just hope he swallows EVERYTHING!  I would hate for him to have to deal with all of those cum stains!

Just wait till you hear what I have in mind for Halloween!!

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!

I’ve been having so much fun lately. Of course, I ALWAYS have a good time with my phonesex callers on Niteflirt…but lately, I’ve been breaking in a new sissy here in my private time. Hubby is not exactly happy that he has to take a “back seat” while someone new learns the ropes…but that’s just not MY problem! He’ll learn to deal with it…as he has in the past when I’ve taken on a new panty boy. There’s nothing like the thrill of watching a panty-clad, tiny dicked sissyboi take his first cock!! They’re soooo hesitant…are they afraid they just might like sucking cock a little TOO much?? How I enjoy holding their heads while my boyfriend shoves that ten inch piece of meat down their throats! You and I know how they crave that…to feel that throbbing dick in their mouths! Once they’ve accepted that, I love to just sit back and let my stud “play”! The look on my new sissy’s face the first time my boyfriend shot his load…talk about a Kodak moment!! And the look of triumph he had…knowing how he had pleased me! I can’t wait till I bring in one of my well-hung black studs…and maybe one of his friends, to really initiate my new little cuck! I’d love to share with all of you my plans…and I know you little cuckld wanna-be’s would love to hear about it while you jerk your teenie weenies!! So get on your knees, get on your panties…and call me!