I had a long time regular that was into anal, public humiliation, and forced feminization, so here is what I would do to make him masturbate:

I’d make him dress up in stockings, heels, garter belt and teddy. He’d get in his car for a drive like this, and bring his nice big dildo with the suction cup on it.

So I’d have him drive to a deserted country road, and get park in the middle of the road. He’d stick the dildo onto the front bumper and fuck himself with it out in the middle of the road, while talking to me.

I wouldn’t let him cum then though. I’d make him go home with a buttplug up his ass, and a raging hard-on in his panties. He’d have to wait until he got home, and called me back. Then I’d tease and deny him for a few more minutes, while I had him stroke for me.

Finally I’d make him cum all over his face. This series of phone sex calls took place over a couple of hours, and was very exciting for the both of us. Most of the time I’d be about to cum myself by this time, and so I’d also masturbate for him as well. Now THAT would really set him off.

If you think you’d enjoy being made to do a public humiliation session like this, while I am laughing in your ear and encouraging you, then you should give me a call.

You can find me on Niteflirt.

Submitted by the Hot Nasty MILF

Every day he has to call me at the same time, and spend 10 minutes with me on cam, masturbating his tiny dicklet.

Teasing and denying a cuckold phone sex caller

And every day I tease and humiliate him about his small penis, and then deny him an orgasm. It’s so funny, because his wife won’t fuck him either. He already knows she’s fucking someone else, so he’s pretty much shit out of luck…

I’m going to let him cum in a week or so I THINK. I’m not sure yet – I may not let him cum at all in this block of sessions.

So I am asking my readers out there – should I let this tiny-dicked phone caller cum by the end of March, or not? And if I do let him cum, what should I make him do with that cum?

You are welcome to leave a comment with your answer.

Submitted by Lilly, the Hot Nasty MILF

How many of you are sitting at your desk or in your armchair right now with a pair of women’s panties on? You’ve either stolen them out of your wife or girlfriend’s drawers – OR her hamper – or you’ve ordered some for yourself online or even bought them at a lingerie shop like Victoria’s Secret.

If you did buy your own panties, did it give you a thrill? Did you wear panties into the store itself when you bought them? Did you tell  the salesgirl it was for you?

Call me for sissification and humiliation phone sex and I can goad help you into actually buying panties and other sissy boy items, like bras, nylons, pantyhose, teddies, corsets, and make-up.

I love to have a guy call me when he gets to the store, and have me on his phone the entire time he’s picking out the lingerie. I’ll be in your ear whispering what a naughty little peener sissy boy you are. I of all people understand how the humiliation and being forced to buy sissy clothes and wearing them makes you oh so excited!

The Hot Nasty MILF Can Sissify You, Panty Boy

Does this sissification and humiliation blog post make you think of the possibilities that could happen when you call a good phone op like the Hot Nasty MILF? Good! Keep thinking like that – and then you can either call me or email me at hotnastymilf@gmail.com to discuss what you’d like to do.

If you’re a new member you’ll get 3 minutes free phone sex just to talk to the flirt of your choice. ;=)

Submitted by Lilly, the Hot Nasty MILF

His date Miranda was in her early 20′s but she acted like she was 15-going-on-2. She would have been a very pretty girl if not for the petulant mask of abject misery, and the sighs and rolling of the eyes while we were at dinner. And her voice! It was like fingernails on a blackboard, especially during her dramatic melt-down in  the middle of the party where she threw a tantrum with Edward and flounced off. Of course she was totally ignored after that by the adults in the room (most of whom were parents and have seen a tantrum or two in their day), and so she had to stomp back in again to get her much-needed attention.

No matter – during the formal sit-down dinner, I was opposite her boyfriend Edward, and I kept him amused by teasing him, stroking my toes in their stockings up and down the inside of his leg… And then later I was able to get him by himself (right after the flouncing scene) to make a little cuckolding date for some hot, nasty sex.

For all the little “brats” out there who think pouting, screeching, dropping your drawers and showing your hiney, and “It’s all about MEEEEEE” is sexy…Ummm no baby doll, it’s not sexy at all. If you can’t even control yourself, how can you control a man in bed?

The art of seduction is sexy. Being a mature MILF is sexy. Why do you think so many men are all about mature women who know what they want, and know how to get it?

Being Southern is sexy. I think that’s why so many men find Southern women exotic and desirable. We are taught from birth to have excellent manners, but get us in the bedroom and you will find a seething volcano of passion. And I for one have no taboos.

Sometimes a smile, a look, a wink, is louder than a screeching temper tantrum. And crossing your legs and letting a little bit of thigh, or dropping your heel to show the arch of your foot is more erotic than showing your ass any day.

Showing Nothing Can Be More Erotic that Showing Your Ass...

Are you into mature MILF’s who know what they want and know how to get it? Love to hear a sensual sexy Southern voice, taking charge and telling you exactly what to do? Well then, darlin’ you should call me, the Hot Nasty MILF.

If you’re a new member you’ll get 3 minutes free phone sex just to talk to the flirt of your choice. ;=)

Submitted by Lilly, the Hot Nasty MILF

Since he can’t doesn’t have enough cock to make a woman orgasm, I like to keep him in a chastity device, like the CB6000. I might as well, as it’s no good to anyone.

Once he’s been in chastity for a couple of weeks, I love to play cuckold games with him – especially when I have a “real man” over at the house.

I wait until hubby is whining about wanting to cum all the time, that his balls huuuurt and are all bluuuuuue. Yeah, whatevs.  Well it does make him a lot more submissive to me.

And then I’ll sissify him by dressing him up in his little girly panties and his thigh high stockings, and his fuck me heels. I’ll also stick a nice big buttplug up his ass.

Then I’ll make him suck my boyfriend’s huge cock to get it nice and erect, and then watch my boyfriend bang the hell out of me, while he kneels beside the bed. He’s NOT allowed to touch himself at this point.

After I’m totally sated, and so is my boyfriend, I’ll take hubby’s chastity cage off. I’ll lie in bed, all nasty and sweaty and full of another man’s cum. I’ll spread my legs and make hubby rub his face in my open, oozing pussy. Then I’ll make him lick every drop of cum out of my pussy, and I’ll squirt all I can into his mouth. He is NOT allowed to touch himself at this point. It doesn’t matter, he’s rock hard within a minute of removing the chastity device.

And then I’ll give him 6 strokes and one minute to cum all over my swollen pussy lips. If he doesn’t come in that time per period, he doesn’t get to cum at all. Nope. Nosiree bob. Put the cage back on mister. Until next time.

About half the time he can’t do it. I’m not sure if it’s because he’s waited so long, or my real man is laughing at him, and humiliating him, as well as myself. He starts crying and begging for me not to put the cage back on, but I do it anyway. I tell him he’s blown his chance. He should be grateful I gave him one.

The rest of the time he cums all over my lips. I make sure that he only gets one minute, and six strokes. If he’s not done cumming, I pinch his head hard to stop him, and then make him use an ice pack to make himself go down. And of course he has to lick his own cum off me, that goes without saying.

Are you into small penis humiliation, or just humiliation? And do you like the thought of being cuckolded by a dominant MILF?

Then you should give me a call.

You’ll get 3 minutes free just to talk to the flirt of your choice. ;=)

Submitted by Lilly, the Hot Nasty MILF

My site on there is Hot Nasty MILF and from there you can see all my listings and call buttons – and they do work! And of course we can talk about all the naughty, nasty things I’ve always talked about on Niteflirt – you’ll see a list of the things there that I especially am good at, like fantasies, being the mature, older MILF, mutual masturbation, cuckolding, or just taking charge of your body and mind – and leading you to an explosive orgasm..

Submitted by Lilly, the Hot Nasty MILF

a. How does he get such beautiful girls hanging on him?

and then

b. How big is his penis?

I bet you do.

I bet you look at men, and you can’t figure out how they have all the women, when they are no more attractive than you, or richer than you. But there’s a certain je ne sais quoi about them, n’est pas?

It’s that indefinable air of self-confidence that all your bravado and bluster can never match, little dicklet boy. It comes from having a healthy size penis, and not having to compensate in so many ways or to constantly feel the loser that you must feel you are.

Sure, women can tell you “Size doesn’t matter,” but you can see they are lying. And you know the first man with a big cock that treats them halfway decently will carry them off – if they have any sense that is.

So what to do? It’s not like you can get a penis transplant, now is it? And all those pathetic penis enlargement pills and creams don’t work – I bet you’ve already tried them and know that.

Accept your state of loserness. Realize that you, too, can get off, just by being humiliated for your tiny cocklet. Realize that even though women will not ever want to fuck you, you can hopefully watch, and maybe even help – providing you have other talents like making money for them.

I can help you learn your place in life.

Give me a call =)

Submitted by Lilly, the Hot Nasty MILF

It wasn’t until I was grown that I found out that “the sin of Onan” wasn’t masturbation at all but in fact was the act of wasting your cum.

Or as Monty Python would say “Every sperm is sacred.”

Now you wouldn’t want to go against God who gave you  that lovely joystick to begin with would you? I mean, it may be teensy and all and I may even humiliate you for its size, but that little clitty gives you great pleasure, I am sure.

And masturbation could possibly give you a longer, more enjoyable life..

So what to do? Well you can always EAT YOUR OWN CUM..

That’s not wasting it now is it? Nope, not at all. Cum is good for you and nutritious, as well as being high in protein and low in fat and carbs if you’re on a diet.

So everything Miss Lilly has been making you do when you call is for your own good, and I want you to remember that.

Now if you haven’t called before I am always happy to take new callers. Just make sure you have a little “dribble glass” to catch your cum with.

Submitted by Lilly, the Hot Nasty MILF

I have a very amusing phone sex call I can talk about.

I was on Niteflirt late one night, while waiting on my cuckold husband to come home and service me, and so I got a call from a cam whore cross-dresser regular of mine.

Now this cross-dresser was into sissification, humiliation, and forced bi, and liked to dress up for me on cam, making himself into a slut. I would direct him while he’d put on all kinds of skanky revealing panties, bras, hose, lots of make-up, and of course cock-sucking whore red lipstick.

He also had several dildoes that he liked to use for anal play, and I would humiliate him and tease him, making him suck a big fat dildo and then stick it in his little wet pussy, but only after he begged and begged for that “big black cock”.

This little cam whore of mine was married, but he would always call me on Tuesday nights when his wife went to an ongoing education class. According to him, she had no idea he even liked to cross-dress, much less his bisexual fantasies.

So I’ve got him across the bed, his ass up in the air, all painted up and with a blonde wig, lipstick etc. He’s got one big dildo in his mouth and fucking himself up the ass with another.

His back is to the door, and so he doesn’t see his wife open the door and the look on her face. I’ve never seen such a look of shock and horror in my life – her mouth was a perfect O and her eyes were wide as saucers as she’s watching him fucking, begging, gagging, moaning etc.

I went ahead and let him cum before I told him she was watching – I figured he wouldn’t be getting any kind of sex for a while – phone sex or real-time sex, at least not from her.

And I was right, it was six months or so before he started calling again.

It took everything I had not to laugh and spill the beans while I was watching her watching him though.

Do you like sissification and humiliation? Like to play with toys and beg for that big dick? I enjoy doing this calls very much and I am quite good at them.

Try giving me a call.

Submitted by Lilly, the Hot Nasty MILF

As my regulars know, I took off Sunday night to kick up my heels and do a little cuckolding, as well as a bit of cock teasing..

I went to my husband’s country western bar and grill on Second Avenue in Nashville, so I could flirt with, and tease, and possibly even pick up a man right in front of my husband while he was working the bar.

I started dancing with a tall rangy looking cowboy, and you know what they say about tall men, right? Long blue jeans.. Well also big cocks. And boy howdy, did this young man have one.

The band started playing Johnny Rivers’ “Slow Dancing” and I had my arms around him, and was grinding into his cock with my wet pussy right through my thin little cotton dress and silk panties.

He had his hands all over me, whispering in my ear he wanted to fuck me so bad, could we go somewhere so we could fuck please?

But I was having way too much fun making hubby watch me from behind the bar. I knew hubby’s little chubby was rock hard watching his wife practically climb all over a man on the dance floor. So I kept saying ‘No, let’s just dance a bit more, then we will leave and go back to my house.”

And then it happened. As I was grinding into that nice big fat cock, I felt it spurting through his blue jeans and he started practically dry (well wet actually) humping me there. I felt the growing wet stain through my dress and nylons and looked down. The cum was spreading all down his left leg.

I just started laughing and told him go home and clean himself up, maybe next time you’re in town, cowboy. I did have a lot of fun cock teasing him, and I think I will try to make that happen again.

Then I went and found another man to fuck that night, but that’s another story..

Enjoy being cockteased and cuckolded?

Give me a call..

Submitted by Lilly, the Hot Nasty MILF