I have a humiliation cuckolding caller who likes to go beyond the usual cuckold phone sex fantasy. While there’s always a humiliating component to cuckolding, this guy likes to take it to the extreme. One of our recent calls had to do with him worshipping my various male lovers before and after they fucked me. I told him that since I love when he gives my feet a tongue bath, he needed to do that for the six lovers I had present. Now women’s feet, I’m sure you’ll agree, are very pretty and sexy, but a guy’s feet? Uh, not so much. So he wasn’t too thrilled about having to twirl his tongue around my lovers’ toes and suck the sweat and sock lint off them! But he was a good boy and didn’t complain.

But I wasn’t finished with the humiliation. I also wanted him to relax my lovers by tongue punching their fart boxes! I wanted him to stick his tongue waaaaay up inside their butt holes and totally clean them out. Yuck, I can’t imagine doing that, but afterward he had a shit eating grin on his face. LOL! I wonder what my devious mind will think of next to further the humiliation of this cuckolding caller!

Jezel
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One of my favorite phone sex role plays is whoring sissies out at a glory hole! Just the thought of it makes me laugh – thinking about my sissy sluts with their frosted blue eye shadow, smeared mascara, and smeared lipstick.

Ditzy Deena was one of my latest sissy sluts to be escorted to the glory hole of my choosing. Oh, she says, I could never do something like that. I’ll suck your dildo cock, Mistress, but I could never suck a real guy off. I told Ditzy Deena she’ll do exactly what I’ll tell her to do, or else she won’t have me as a Mistress any more.

Well, poor Ditzy Deena just didn’t like the thought of that. Horrors, she exclaimed! So with much trepidation, she came with me to the glory hole. I told her it was make or break time, so she slowly crawled over to the hard dick sticking out of the hole. Go on, it isn’t gonna suck itself, I told her.

With a quivering voice (me thinks she was crying a bit), she said she would do as she was told. Then she treated me to wonderful and realistic cock sucking and cock gagging sounds. Silly ditzy Deena – pretending to not want to suck cock. You’re such a whore!

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Aden

If you’re wanting to be the best femme you can be, then it’s time for some sissy training! I have a few sissies who are under my direct sissy school tutelage right now. A couple are sissy maids, and one wants to be a total cum slut. Each one, even the sissy maids, needs special and personal attention because no two sissies are alike. One sissy maid likes humiliation and has more in common with the total cum slut, whereas the other sissy maid wants to really stress her feminine side and of being the best of service, but not in a cum slut kind of way. It’s more like an Alice from the Brady Bunch kind of way – being the best maid, cook, cleaner, and all around jill of all trades when it comes to household matters. All of my girls are doing well in their sissy training, and I’m very proud of them. I love hearing from them and giving them new assignments in how better to improve. So what improvements do you need in your sissy training?

Riley

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I was surprised when I got my first castration fantasy phone sex call. I thought wow, do guys really have castration fantasies? I asked him some more questions and realized it’s at the extreme end of the cbt spectrum, so I was more than happy to play along. His fantasy revolved around jerking off to the girl who lived next door, and I caught him. I was furious so I tied him up, iced his balls, and then sliced them right off – lol! Funny thing is, he never jerked off to the girl next door – or to any girl – ever again! Castration is a great cure for keeping such guys like that in line. Muhahahahaha!

Piper

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I love dildo training sissy whores. Whenever one of them calls me up on the phone for some sissy slut training, you know I’ve got my big strapon handy. I also expect my dildo training sissy whores to have at least one dildo (preferably three of various sizes) around to start the training. Since I like to get right into the training without pussyfooting around (haha), I expect you to be ready for some ass banging action. Ready? Set? Be my bitch, sissy!

Aspen

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When one of my callers the other day said he wanted a mean mommy who forces boys to smell her dirty panties and humiliates them for it, I knew exactly what to do. Those of you who’ve had the ball draining experience of playing with me on the phone knew I was up for that kind of role play. I forced little Johnnie to smell my dirty panties when I caught him sneaking in my panty drawer. I told him that if he really wanted to know all about mommy’s panties, then he should get up close and personal with her dirty panties. So I sat Johnnie down and emptied my dirty clothes hamper on top of him. Then I rounded up all my dirty panties and made him smell them. He was so humiliated that he started to cry. Oh boo hoo! That’s what you get, little Johnnie, for rifling through my panty drawer. You get a mean mommy who forces her boys to smell her dirty panties and then humiliates the jizz right outta them!

Jezel

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I had a guy call the other night afraid to confess his deep, dark secret. After some hesitation, he finally confessed that he wanted a femdom who makes a guy her toilet slave. He thought he was being really presumptuous in asking me for such a request, but I just laughed. I reassured him that I LOVE making guys my toilet slave. What better way than to humiliate a submissive loser and to show him where he really stands in the pecking order. It’s one thing to hurl insults at a submissive, but it’s quite another to treat them as my toilet slave. Suffice it to say, his mouth was full of piss and shit that he was gagging. I’m sure the fucker was burping up piss and turds all night long. LOL!

Roxy

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If a femdom wants to prove ownership over a submissive, I say a great way of doing so is one who brands a sissy on her ass with her Mistress’ name and then cuts off the sissy’s balls to show her who is boss. I told one of my callers that, and she giggled and gasped in horror. Well, says I, are you afraid to role play that? She nervously gulped and said maybe we could try it. So I tied up my sissy and pulled her panties down. I branded her ass with a red hot poker that has my name on it. She was whimpering and crying, but I told her to stfu. She wouldn’t. Sigh…such a drama queen. So I had to really show her who’s boss by cutting off her balls! Now she’s limping around with no balls (yay!) and a burned part of her ass. No telling when she’ll be able to sit again, but at least she doesn’t have those stupid balls dangling down. If she misbehaves I may have to cut off her sissy stick and stuff it down her mouth since she’s such a cock whore. LOL!

Marlow

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One of my regular submissive callers has been with me for awhile. We’ve experimented around with all kinds of bdsm play, and recently he expressed an interest in anal sex. I’ve done anal on a guy over the phone before by instructing him on how to do it, so I suggested that to him. He really liked the idea, so I had him purchase a slender dildo and plenty of lube. About a week before the fateful anal phone sex call, I had the guy deny himself for me so that I knew he’d be good and horny. We took our time, and slowly I seduced him and made him feel totally relaxed and turned on that he was soon begging me to allow him to stuff that dildo up his virgin ass. I waited just a bit longer, and then I told him to ease that dildo in his anal hole. I think I made that guy into a total anal slut because now all he wants to do on our calls is fuck his ass! Yep, his ass is now all mine. LOL!

Jade

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A lot of guys who call me for forced bi phone sex aren’t the least bit sissy. I know some people think that’s what forced bi guys are like, but that isn’t so. A lot of my callers are like James (not his real name, but you know, I gotta protect the innocent – lol)! Anyway, James is a real take charge kind of guy, you know, an alpha male type. He’s the boss where he works and he’s always giving orders. But he’s got this secret inside him – a secret that he plays out with me. During our forced bi phone sex role play, he gets to go with the flow – letting me take charge and give the orders. As much as he protests about following my orders for him to get down on his knees and open wide for my friend’s big cock, he eventually obeys. He loves giving over his power to me, from my order, through the struggle, and on to getting his face fucked and his throat coated with spunk. If only his employees knew – lol!

Jenna

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