Humiliation Phone Sex with Jillian

humiliation phone sex

You know, I consider myself a dominant MILF, but more of the sensual kind. I don’t believe that I’m very strict with the submissive men around me. Yes, I have rules, but there aren’t many of them. And the ones I do have are very simple, aren’t they?

Now, if I were to ask you which of these few and simple rules is the most important one, what would you say? Yes, that’s right. No cumming without my permission.

And yes, somehow, despite you knowing this and despite how very simple it is, you still managed to disappoint me by going and breaking it. That means I’m going to have to punish you for it.

How? With humiliation phone sex, naturally.

First, you’re going to get naked for me. But not *just* for me. My friends will be there, too. And it’ll be CFNM, so you’ll be the only one not wearing clothes. We’re going to laugh at your small cock first, of course, but that’s low-hanging fruit. I plan on moving on to bigger, better, and more embarrassing things to make sure you’ve learned your lesson.

I plan on having you do all kinds of ridiculous things for the enjoyment of my friends and me. Maybe we’ll give you humiliating jerk-off instructions that you must follow, even though you won’t get to cum no matter how much you beg. Maybe we’ll have some of our male friends over, too, so that they can see how pathetic you are.

Oh, there are so very many possibilities for humiliation phone sex punishment, aren’t there? If you call me now, you can get what you so obviously deserve.

Jillian 1-888-704-6848

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Cum Eating Phone Sex with Jillian

cum eating phone sex

Let’s talk about cum eating phone sex, my dears.

I know you’ve always wanted it. You’ve always been curious about what it’d be like. You wanted to know what cum tasted like, and what better place to start than with your own?

But even though you find the idea sexy while your cock is hard, as soon as you blow your little load, you don’t want to do it anymore. And that’s almost surely why you’ve been seeking out these older dominant women like me, isn’t it? Subconsciously, you’re thinking that if you can’t bring yourself to do it, then maybe someone like me can make you.

And that, my reluctant little subbie boy, is exactly what I’m going to do. You may have always chickened out before, but that comes to a stop today.

Oh, don’t worry too much. I’m going to help you out. I’ll work you up into a frenzy with jerk-off instructions and edging, so you’ll be willing to do anything if I’ll just let you cum. The bargain, of course, will be that if I let you cum, you’ll have to eat the mess you make.

And since you’re a precious thing who’s still nice and flexible, I’m going to make it even easier for you. I’ll teach you the very best position to get into to give yourself a self-facial. That way, when you’re finished, you can just lick it all off your lips and chin without even having to change position.

After that, congratulations. You’ll have successfully completed your first cum eating phone sex session.

Now give dear Ms Jillian a call 1-888-704-6848


Sissy Phone Sex with Jillian

sissy phone sex fantasy

One of my favorite things to do with my little sissy phone sex husbands (or sissy wannabe husbands) is to dress them up in the manner of *my* choosing, rather than their own. What I want them to do can sometimes be quite different than from what they want to do themselves.

But of course, they obey me because they can’t not obey me. I seem to have that effect on people.

When this sort of thing happens, my go-to plan is usually to lay out a pair of panties and perhaps some matching lingerie of some sort for him to wear to work the next day underneath his usual work clothes. He’s always happy enough to do that, so we go to bed without another word mentioned on the subject…at least until the next day.

The next morning, after he’s gotten out of bed and showered and is in the process of getting dressed, I stop him before he can get too far along. Then, I pull out a bottle of lube and the plug I secretly selected for him the night before, and I tell him that there’s something else I want him to add to his outfit.

He’s usually surprised and then wary. “You really want me to wear that ALL DAY?”

Yes, darling, of course I do.

Eventually, though–because he can never resist me–he agrees, and I bend him over the bed. I lube him up, work the plug in, and fuck him for a couple of minutes with it, just to tease. Then I pull his panties back up over his semi, pat him on the ass, and tell him to go back to what he was doing.

My last words to him before he heads out the door are always something like, “I hope those panties are enough to hold your plug in place. It’d sure be humiliating if it fell out while you were in the middle of a meeting, wouldn’t it?”

Does that sound like the kind of sissy phone sex fantasy you’d enjoy? If so, then call me at 1-888-704-6848 ask for Jillian.

Cheating Wife Phone Sex with Jillian

cheating wife phone sex cuckold

Throughout my marriage, I was a cheating wife, and I enjoyed it immensely. Even now, after my divorce, I like to have my fun with as many large cocks as I can. And why shouldn’t I?

Of course, after all that experience as a true cheating wife, that means I’m quite the expert at cheating wife phone sex. And I love it because it combines two of my favorite phone sex-related things: cuckolding and roleplay.

Oh, yes, the role play is what makes cheating wife phone sex different just regular cuckold phone sex. We pay a lot of attention to the story itself, using backstory, and interactions between the two of us (and possibly others), and scene-setting, and so forth to create a fantasy that’s something more than just mere cuckolding. It’s more intimate, and therefore, far hotter.

What kinds of cheating wife roleplays do you like? Do you want to walk in and catch me in the act, perhaps? Or do you want to know what I’ve been doing while I’ve been leaving you home alone, drooling and jerking off over the thoughts of what’s happening? What about being made to go out with me and choose the man I’ll be going home with tonight, knowing that if you make the wrong choice, I’ll never allow you to participate in any of my extra-curricular activities ever again?

I’m up for any of it, so you tell me.

Just ask for Jillian at 1-888-70-HOT4U

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MILF Phone Sex with Jillian

milf phone sex

Men call for MILF phone sex for many different reasons, although they ultimately boil down to the same thing. They’re attracted to MILFs, obviously. MILFs like yours truly.

And why are they attracted to MILFs? Well, again, it’s for many different reasons. I think that for many men, it’s because older, more mature women are usually more confident and therefore more open-minded sexually. We’re not worried about petty things like how we look in a certain position or if we’re doing a good job. We know we look good, and we know we’re doing a good job, so we can concentrate on what’s important–mutual enjoyment.

It’s also a matter of simply knowing what we want and knowing how to get it. And not being afraid to pursue it aggressively, if necessary.

And we know this because we have had lots of sexual experiences. Then, with all those experiences comes plenty of skill. When you consider all those things together, I think that’s reason enough for any man to want to try MILF phone sex.

Are you one of those men? Maybe you’ve never had phone sex with an older woman before and would like to see exactly what it’s like. Or maybe you have done it before and are desperate for more. Either way, you should give me a call and let me show all the things I can offer.

Jillian 1-888-704-6848

Forced Bi Phone Sex with Jillian

forced bi phone sex milf

As much as I enjoy big cocks myself, I’m not completely selfish. Oh, I’ll get what I want out of them, of course, but I’ll share sometimes, too. Whether you want me to or not, actually. It’d be awfully rude of me to do otherwise.

Do you want to get down on your knees and take a real man’s cock in your mouth? If you do, I can make that happen for you with a snap of my fingers.

Is that something you’re not into? Does the idea of sucking cock make you nervous or fill your body with dread? If so, I can still make it happen. Forced bi phone sex can be rather entertaining under the right circumstances.

I would love to coerce you into sucking cock for me. You wouldn’t want to disappoint me, would you? Or if the situation calls for more direct measures, I’m also not about holding or tying you down in order to keep you still for it. I can even put an open-mouthed gag on you so that there will literally be nothing you can do to stop yourself from getting throat-fucked.

Of course, the more cooperative you are, the easier forced bi phone sex will be for you. So if you’d like to avoid getting face-fucked against your will, it’s much better if you just obey my commands.

Keep that in mind when you give me a call at 1-888-704-6848 just ask for Jillian

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Strap On Phone Sex with Jillian

strap on phone sex

I know how much some of you love feeling something long and thick inside. And I completely understand, my dears, because I love it, too. But I love dishing it out just as much as I love receiving it, which is why strap on phone sex is always a good choice in my book.

Technically, I have a number of dildos that fit perfectly into my favorite strap on harness. But I know that all of you little size queens out there won’t be satisfied with anything less than my biggest one, will you? So for all intents and purposes, I suppose I only have one dildo for you–my big 11 inch one that’s roughly as thick as a soda can.

Oh, don’t get scared now, boys.

You see, I can’t wait to get it out and use it on you. I want to see you down on your knees, coughing and gasping and struggling to swallow it all down. I want to fuck your face with it and hear you gag and see the tears roll down your cheeks. And when I’ve finished using your mouth to my liking, I want to see you up on all fours, presenting yourself to me, so that I can bury the whole thing inside you with one long, hard thrust.

What do you think? Are you ready for a strap on phone sex session with me and favorite toy? Come on and show me what a size queen you really are!

Jillian 1-888-704-6848

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Creampie Phone Sex with Jillian

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Hello there, little cuckolds. I’ve got a nice fantasy scenario in mind for us tonight. Picture it in your head for me, and let me know if you like it.

Imagine this: I come home late one night. You have no idea where I’ve been This is nothing unusual for me, of course, so you don’t ask, but you’ve got your suspicions. And those suspicions arouse you to no end, don’t they?

After I come in, I take you to the bedroom with me, where I tell you to take off all of your clothes and then mine, too. You begin to grow…excited…because you think I’m going to take you to my bed and let you fuck me. But that’s not what happens at all. Instead, I push you down on the bed on your back, climb up to sit on your face, and tell you to lick me.

At the first taste, you know that your initial suspicion was right. You’re licking another man’s cum out of my pussy. It’s a creampie phone sex surprise, and I saved it just for you.

Oh, I bet your cock would get hard at that, wouldn’t you? You wouldn’t be able to resist. And after you finished your creampie cleanup duties, will you confess your secret cuckold desires to me? You will, won’t you?

Mmm, yes, that sounds like everything I could possibly hope for out of a creampie phone sex call. Wouldn’t you agree?

Just ask for Jillian 1-888-704-6848

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Phone Sex Size Queen Jillian

 phone sex size queen

Hello, boys.

I must say, it always makes me laugh a bit on the inside when I hear younger women talking about how they like men to have big cocks, but not too big. I always have to bite my lips to keep from laughing out loud when they start saying things like, “Oh, a little extra is good, but after a point, it just gets too big and too thick for you to enjoy it!”

Now, this phone sex size queen would never be so rude as to say what she was thinking, which was something like, “Oh, honey, one day you’ll learn. After you grow up, you’ll be able to handle real cocks.”

Personally, I say there’s no such thing as “too big.” Ha! The very idea is ridiculous. If a man can bring it to me, I can take. Well, assuming it’s big enough to suit my tastes, that is. If it wouldn’t be completely crass, I would have a sign somewhere that says “Must be at least nine inches to ride.” But I’m certainly not that crude, so the sign will simply have to remain in my mind.

And if there’s no one available with a big cock for me, I simply make myself available for size queen phone sex sessions instead to keep me amused until one of my many lovers is free. If you boys aren’t big enough to please me, I’ll just cuckold you instead. That will surely make the time fly by.


Jillian 1-888-704-6848

My aim and yim is hotmilfjillian

Cuckold Phone Sex with Jillian

cuckold phone sex

One of the things I hear quite often from my callers is that they’re voyeurs. They like to watch other people in sexual situations, especially if “other people” includes their wives, girlfriends, or any other woman whom they know personally and are sexually attracted to.

And lest you get the wrong idea, it’s not just women’s solo masturbation sessions that they’re watching, either. Oh, no. They also love watching these ladies fuck other men…suck their cocks…and all sorts of other things.

I suppose it’s possible that there are that many voyeurs in the world. But I think it’s more than that. It seems to me that it’s a lot more possible that a lot of them are simply cuckolds in disguise. So when they call me and tell me that they want to “watch,” I think it’s very likely that what they’re really asking for is cuckold phone sex.

And nearly every time I’ve made that guess, I’ve been correct.

You see, I think a lot of would-be cuckolds are hiding their secret behind the “voyeur” label because they’re nervous or ashamed. They think that simply watching other people have sex will be enough to sate their urges. I’ve certainly seen it happen often enough.

But they’re wrong about that. When one is a cuckold, the experience of watching is really second to the humiliation of it all. And when too much emphasis is placed on watching while also neglecting the desire for humiliation, then the fantasy is never really fulfilled, and the man who has the fantasy is never really satisfied.

I suppose what I’m really trying to say, my dears, is if cuckold phone sex is what you really want, ask for it.

Jillian  1-888-704-6848

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