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October 2008
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My Little Winky Boy

October 4th, 2008

I call him that because he has such a little winky, and he knows that a woman like myself would not be satisfied with such a teeny little cocklet.
I keep him in a cage to keep him out of trouble and to show him I own his winky.

Tiny Little Winky

Tiny Little Winky

He calls me on Niteflirt and I let him out of his cage for the duration of the call so he can get himself hard for me. He knows to have his “dribble glass” and a bag of frozen peas handy. Sometimes he gets to “dribble;” sometimes he has to use the peas to get himself soft again.
He has real life adventures also it seems.

He had a couple of friends, Athena and Jessica, over the other night, and they started snooping on his computer. Here is what he had to say about that:

I forgot to log out of my yahoo group sites. The subjects were SPH, Ballbusting, Cuckholding, Facesitting, Cunniligist, Upskirts and Humiliation. My 2 friends Athena Jessica saw my groups. After others left they asked if i ever heard of SPH CFNM. i said maybe. WHY? They told me what they found. they said i must have a little cock if i looked at SPH sites. They asked to see. i told them i’d prefer not to. They insisted or they would tell all my friends what i was into. i consented and they laughed when they saw the cock cage. They asked why i wore that and i explained i used to have someone who kept me locked. i said i thought because they hung out with each other all the time they might be gay. They said they were bi but they were also SIZE QUEENS. They asked me to remove the cage but i told them there was a personal reason i couldn’t. ( i have been wearing the cage 24/7 for MS. LILLY) They downloaded all my groups to their computer and said they were going to check them out and probably have some fun with me. They squeezed and kicked my balls and teased me to watch my little cock grow into the spikes in the cage and laughed. They said next time the cage must come off so they can see my little cock. i think i might be in for it in the near future!!!! LILLY’S Winky boy

So I told Winky boy that he had to stay in the cage for the time being, but perhaps we could set up something where I give Athena and Jessica instructions on how to tease and torture and deny him… I would so love to watch that on cam :)

Until next time, happy wanking!

Teasing a Niteflirt Caller of Mine…

September 13th, 2008

As a Hot Nasty MILF on Niteflirt, I don’t just do cuckolding and small penis humiliation with my phonesex callers, but rather I employ a large variety of fetishes, depending on what the caller needs. And one of those fetishes is teasing and denial.

I have a teeny-weenie caller on Niteflirt that I have in a chastity device right now. The time he called before today, I gave him a fantasy about peeking up women’s skirts by being a shoe salesman, and then I had him look in a hole into a department store dressing room, as I rode his ass with my strap-on. I made him use a dildo for that fantasy, even though he had on a cage at the time.

Today he called looking for relief, and I fed him a story of being his next door neighbor, who watched me come in every night, and stripped and masturbated in front of an open window, night after night. I used my sextoys on myself, to bring myself to orgasm. I even let him take off his cage, and get very very close to cumming.

But then I made him put his bag of frozen peas on his balls, and bring himself back down. Then he had to put his cage back on his little cocklet. No cumsies for tiny-dicked losers today, I’m afraid.

Perhaps next time…

Until then, happy wanking! :-D

Lilly

Another Cuckie Caller on Niteflirt

June 24th, 2008

My cuckie caller on Niteflirt SAYS his name is Paul Marks, but I don’t know if that is true or not.
He has a wife named Erica that likes to cuckold him.
And how! Erica, my hat is off to you sweets :-)
She is so mean to him, humiliating him at every possible moment…
Sometimes she goes out without him, and makes him get her ready for her fuck-buddy date, telling him over and over that she’s going to see a REAL man with a REAL cock, unlike his teeny little weener. And then when she gets home, all full of another man’s sperm, she will make him get down on his knees and sniff her panties, then pull them down and lick the cum out of them.
She has a framed certificate that is outside of her bedroom that is signed by him, that it is ok for other men to fuck his wife.
In fact, when she brings her men home, she makes him beg over and over for them to fuck her, then for her to let him lick the jizz out of her cunt.
The other day when he called me, he had to tell me 50 times each that other men fucked his wife, and that he licked their jizz out of her. I nearly cried, I laughed so hard.
She has 2 black men that fuck her sometimes, Derek and Marcus. They request that Paul be dressed in his little school-girl pleated skirt and white anklet socks and heels when he watches them tag-team and DP his wife. I nearly lost it when I heard that. And he has to beg to suck their cocks, and to put them in his wife as well. And then of course to lick the cum out. They fuck Erica so hard and so well, she goes into what I call a “brown-out” where you cum so hard and keep cumming you just totally lose all rational thought.
Erica has a little room for Paul to sleep in when she has other men spend the night. It’s just a plain little room, with only a bed. But adorning the walls are her panties, full of other men’s dried cum, and stapled onto the walls. I can only imagine how this room smells.
Of course he is not allowed to cum except when she says so. Sometimes she even milks his prostate rather than let him cum.
One night he came, even though he wasn’t touching himself, while she was humiliating him, making him lick her cum-filled pussy, and she made him lick it off the tile floor of the bathroom.
She’s also training him anally and fucking him with a dildo while she makes him suck that big black cock, so you can pretty much guess what is coming just around the corner…
Paul has spent several hours with me, telling me all these things. He is SUPPOSED to send me pictures of his face covered with other mens’ cum. His wife loves to take pictures like that so she can humiliate him even more at a later time.
I do hope Erica reads this, Paul. If not, please do let her know that I am waiting for those pictures so I can put them on my blog.

Cuckolding on a Sunday Afternoon…

June 9th, 2008

I had a great Sunday afternoon off…

Hubby was actually off this last Sunday, which is a rarity for him. So I decided to take advantage of the situation and have a couple of his old football buddies over - the ones that I used to sneak around and fuck, after hubby had consumed his first six-pack.

Now I just fuck them out in the open, with hubby watching…

Yesterday was even more fun though, as I dressed him up in a pair of my black silk thong panties and some heels, and made him crawl on his knees to one of his friends, the one with the biggest cock. I had hubby get his friend, Mark, all ready for me, sucking on him until he was fully erect, then had him put Mark’s cock inside my waiting pussy, which his other friend, Adam, was getting ready by licking.

Isn’t it wonderful when a married couple works together like this?

And just because Mark got to fuck me, and Adam had to watch, I rewarded him by making hubby suck Adam’s cock until he blew in his mouth.

Then I allowed hubby to remove his cage and stroke himself through those silk panties until he came inside them. He had to wear them the rest of the day like that ;)

It was such a fun day, we might just do it again later this week :D

Happy wanking!

Having Fun with Chastity

June 5th, 2008

Oooh, not me of course… I don’t see the point personally. But with my hubby, yes, it’s been fun the last few months, keeping him in a CB6000.

What’s even better than that is to have him in one, and then to make him watch me in action with another man. He doesn’t want to admit that it turns him on, but he would be hard as a rock if I let him out of his cage.

I do let him cum occasionally, of course….

I have a little group of boyfriends that I like to invite over for the “cumming” ceremony.

I dress hubby up in a new pair of panties, and with his sanitary napkin, which he has to wear at all times now. And of course he has the cage on.

I have him pull down his panties and show us all his pathetic little dicklet in its chastity device. And then I make him decide which would he rather do, would he rather have me milk his prostate, or would he rather have all my friends cum on his favorite food (apple pie) and then he gets to cum on it too. But of course the apple pie is in a dog bowl, and he has to get down on his knees and eat it with just his face, like the little piggie that he is.

By the way, he has been smelling me bake his apple pie for him all morning, so his mouth is watering….

If he decides to have the prostate milking, I let my boyfriends eat it all right in front of him, while I am milking him.

If he decides on the apple pie, the entire pie gets jizzed on, as he is not allowed to have any that is not cum-flavored.

Usually he chooses the pie…..

Yup, life is good :)

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About Me



I'm a 36 year-old cuckolding MILF. I love to masturbate via phonesex for strange men, as well as sensually dominate them, humiliate them for having a small penis, tell them fantasies, do roleplay, hear confessions, force them to dress up as women, bitch them out, and so much more!
I charge $1.69 a minute for phonesex on Niteflirt.

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