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Fetish Elite Award

October 18th, 2008

Empress Stephanie was kind enough to present Me with an Elite Fetish Award today.

Recognition for those sites and individuals who perform
outstanding support within the BDSM/Fetish Community
and for their continued efforts in keeping the
Kink in Kinky!!

Awarded to

Lilly, the Hot Nasty MILF

by the lovely Empress Stephanie

In return I will send this award to five of My favorite blogging friends whose blogs I admire. I am so excited :)

More Humiliation and Cuckolding for My Winky Boy

October 15th, 2008

Another email from winky-boy, one of my Niteflirt phonesex cuckold callers:

Hi MS. LILLY, Sun. morning at 8:30 got call from Athena Jessica. They were coming over to play. i was to put 6 eye bolts in hall doorway and get naked and on my knees hands on head and wait in front of door between 11:30 and 12:00. At 11:45 the door opened and a lady i’ve never seen came in. She said OMG and started laughing as i covered myself. Athena followed and said I thought I told you not to move. i put my hands on head then Athena kicked my little balls. She told me that was KATHY a friend of theirs. She was 4′11″ dressed in laid schoolgirl type skirt and white blouse knotted at the waist(no bra). They said Jessica was picking up a pizza and woud be there shortly. They examined my cage, then Athena grabbed my balls and dragged me to a chair. They tied my hands behind back and tied my legs spread wide open. They then tied a rope around my balls and sat opposite me. Jessica came in opened the pizza and sat with them. Then the show began. They were flashing their pantys to me. i trie d to look away but Athena yanked the rope and told me not to take my eyes off their pantys. Things got real uncomfortable in the cage. The needles were digging hard into my winky. Kathy was laughing and really enjoying this. They finished eating then untied me and grabbed my balls and dragged me to the door where i installed the eye bolts. They tied my hands and legs in the doorway so i could not move. Athena wanted the key to the cage and said she wanted it NOW!!!! i told her where it was. She removed the cage and they admired all the little pin pricks in my winky. They went to my bedroom and found my locked box of toys. They asked for the key and i told them i lost it. After a few well placed kicks they had the key. Out came the penis whips, ball para-chutes, nipple clamps, and ball weights. They took a ball weight and clamped it on my ballsack so the balls were pushed to the bottom. Then they started whipping and busting my balls. Then they said time for some teasing of the smallest dick any of them has ever seen. They kept bringing me to the edge until the precum was dripping collecting it in my dribble glass that had 3 lines on it. Jessica said if i filled to line 1 i could get a handjob, bj, titty fuck, anal sex, or regular sex from either of them. If i got 2 lines i could do 2 of them. Line 3 meant all of them. They asked if i wanted to continue. Of course my little head said yes. Every time i came close to cumming i got my balls busted. After a couple of hours i was a blubbering idiot. But i hit line 3. i couldn’t believe it!!! They untied me and said time for my reward. Before my reward i had to perform a task for them. Athena and Jessica said they brought me a special treat. Jessica went to her purse and pulled out two used condoms. Athena had fucked a 9″ cock and Jessica fucked an 8-!/2″ cock before they came over. i had to eat the cum before my reward. Of course my little head said OK. i choked down the cum and said i was ready. Kathy came over and accidently spilled my dribble glass. i was ordered to lick it up. i finished the task and said i was ready. Athena said ready for what? i said our deal. Kathy said too bad i ate the evidence, maybe next time. i started to protest but they said back in the cage. They asked how many keys i had. i said a couple and i gave them 2. They tied my hands behind my back and busted and whipped me soft. On went the cage and click went the lock. All 3 smiled at me then Jessica beat the keys with a hammer and laughed. Athena said not to worry. She had put on a different lock and she had 13 keys made for it. One for them and their other 10 friends. They each kicked my balls and left laughing out the door. So here i sit with ice on these sore swollen balls. (i expect to see them om Wed.

I was laughing my head off after reading all of this. Good job ladies :)

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!

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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 $1.89 a minute for phonesex on Niteflirt.

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