More Humiliation and Cuckolding for My Winky Boy

Another email from winky-boy, one of my Niteflirt phonesex small penis humiliation and 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 :)

Small Penis Humiliation with winky boy

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 pink ruffled panties and 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!

Another Cuckolded Caller on Niteflirt

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.

Do I Really Get Off on Phone Sex Calls?

I had a phonesex caller today ask me did I actually get off on mutual masturbation calls.
My answer is – truthfully? Sometimes yes and sometimes no…
Sometimes my callers know that I am not actually getting off with them, but they still want to hear me moan and gasp for them. It’s just like when you go to a movie theater, you really know that the actors aren’t dying or falling in love with each other, but you are able to be swept up by the whole scenario.
Sometimes a caller will ask for me to fake an orgasm, especially if he’s pressed for time or money, and wants to get off quick. I don’t mind at all, it’s all part and parcel of the job description.
But sometimes a caller gets off more by my gut reaction than by any sound effect. If I cum, he wants it to be real. I am always up front with these guys, as I tell them it usually takes at least 10 minutes to get me to that place where I can truly orgasm. Most of these guys obviously into the body worship of women, love to smell and taste them, lick every inch of them, and it makes it that much easier for me to get off, knowing that they are hanging on every word and description, like how wet my panties are right now, or that my nipples are hard, or my pussy lips are swollen with desire.

Also I will be honest, and tell them that it is quicker for me if I use a vibrator in order to cum. Most of them don’t care, they just want it to be real.
Then there are the times I am not really even trying to get off, usually in domination calls. I have to admit though, that describing domination scenes really gets my juices flowing, and sometimes I surprise the both of us by cumming in spite of myself.
And by the way, I am NOT quiet when I cum… Usually if a guy is close to the edge, my own orgasm will tip him over, even if I am not ready for him to cum.
How do I sound? Well I just guess you would really have to call up and see for yourself, now wouldn’t you?

A Great Caller I Had the Other Day

I had a very naughty phonesex caller the other day. He was so much fun :)

He called and wanted to do a fantasy where he was doing a survey asking questions about my love life. So I said sure, that sounds like fun.

Some of the things he asked were:

  • What is your naughtiest fantasy? It’s rather involved but it has to do with starring in a porno film.
  • Where was the strangest place you ever had sex? In church with my priest.
  • Who was your first lover? My best girlfriend. We actually lost our virginity on a double date.

Well I think you can get the picture, dear reader…

Of course the answers were much more involved and nastier than this but you would have to call me to get the whole story.

Lilly had sex in church with her priest

Lilly had sex in church with her priest

After the survey, he picked the church/priest one to elaborate on and do a roleplay. We both had a LOT of fun with that one :)