Humiliation Tasks For Jerk Offs Who Cum Without Paying

Filed Under Ass Loving Worship, Cash Pig, Douchebag Loser, jewish princess humiliation, Small Cock Humiliation, Super Geek | Leave a Comment

I tenderized the fuck out of this losers cock in this spicy humiliation task that happened. Here’s how it all began,
Princess Melissa, it seems you have caught me jerking to your pics without permission!!
You decide to punish me by sentence of forced Masturbation no cumming just punishing torture!
I will have to jerk off for a long period that you choose 6 hrs is the record using a metronome to keep pace 60 to 180 beats per minute! The trick is I have to use butter as lube and after I lubed up and slick on both my hand and penis I must sprinkle salt and cayenne pepper on my hand and penis! Then jack off at speed you wish as long as you wish adding salt and pepper every 5-15 minutes as you command.
You can punish me any way you see fit including assign more salt, picking up the pace etc.

I ended up making this loser bitch slave ride a dildo while he performed his loser salt rub humiliation task. I wanted to make this loser turn his disgusting uncircumcised dick into a tenderized piece of loser meat. This wasn’t nearly enough punishment for this loser jerking off to me for free! So, I added some toothpaste and Ben Gay into the mix. I was thinking about hot sauce but then I would never want to eat hot sauce again if I had to know he was abusing it like that. I ended up having him jerk off to tumblr only allowing him to jerk off to gay porn for that added spice.

Another day in the life of my phone sex world.

Salt

Inviting My Effeminate Neighbor Over

Filed Under Ass Loving Worship, Cuckold, Forced intoxication, jewish princess humiliation, Jewish Sexpert, Major Niteflirt Loser, Mp3, Phone Session, Small Cock Humiliation, Tease And Denial, Total Sissy | Leave a Comment

Sissy phone sex sessions are one of my specialties on Niteflirt and yesterday I invited my “neighbor” Eric over but by the time he left I was calling him Erica.

“I’m your small sissy effeminate neighbor who has long girly hair. You know I go to the community college but have no girlfriend and have often wondered if I’m a actually a sissy. Yesterday you happened to be on your balcony and could see into my bedroom and saw me trying on panties. You now have a plan to turn me into your sissy cuckold to use.
You know you can charm me and get my pants off, so you invite me over for coffee. Once you expose I wear panties you blackmail me into jacking off in front of you and eating my own cum. You laugh at how small I am and tell me I’ll need to get used to eating cum as you need a good sissy to clean you out after you’ve been with a real man. You tell me I’ll never be a real man but will make a very pretty sissy. You add that I’ll also be dressed as a pretty maid and taking care of you and your house in addition to helping you get dressed for your dates.”

I dressed him up, I put him in the sluttiest panties I could find and turned him into my personal sissy clean up bitch.

sissyneighbor

The Shrinking Fetish Loser

Filed Under Douchebag Loser, jewish princess humiliation, Jewish Princess Mailbag, Major Niteflirt Loser, Small Cock Humiliation, Super Geek | Leave a Comment

Really awesome phone sex call of the week that was a shrinking fetish. This little freak wanted me to be sweet but, that was impossible. How can I be sweet when I’m a born snobby Jewish Princess who lives to humiliate losers with tiny cocks! He only lasted 10 minutes and then he spurt his teardrop of cum. Exposing losers and laughing all the way.

I have a unusual fantasy that involves being shrunk (2/3 inches tall), caught, sensually played with and gently humiliated, teased and mocked, made to pull my pants down and show you my ‘tiny’ little cock, told and shown how you’d twiddle it with your finger, teased as you tell me to play with my ‘teeny, little winky’
Telling me some ways how you’d gently play and tease me, cellophane taping me to the table so you can inspect my ‘cute, little willy’
How you’d dangle me from things and lean down to watch and giggle while I dangle helplessly. I suppose a lot of teasing with your finger and thumb how tiny I’d be and how my cock would be
Being your sweet little man, cute tiny pathetic joi/humiliation? thanks for your time perfect Jewish Princess Melissa
Shrinky Winky Dinky

Shrinking Man Fetish

Sissy Humiliation Assignment Victoria Secret

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Sissy Samantha compleats his sissy humiliation assignment and goes to Victoria Secret and buys lingerie and tells all the Woman working there its for him. Sissy task a total success.

You’ve been so awesome for me Melissa.
Yesterday was the best. Here’s what happened after…I think you’ll like it. I love it.
I was of course very aroused. After my conference call I decided to play with myself (my ass) a bit (still in chastity). So I was down in the basement with some toys. My wife sends me a text saying “mom and dad are coming over for dinner”…
Right then the door opens upstairs. It’s my wife.
She knows I have my little toy thing and watch porn. But it was early and I hadn’t expected her. So I scurry around and try and clean up a bit before she comes down.
When she comes down she says “mom and dad are on their way over…and WHAT THE FUCK IS THAT?”…She’s pointing at my tattoo overy my frilly panties…I explain briefly. But she says get upstairs, they’ll be here any minute…And she also sais “I will get you a REAL tattoo right there”
I’m running up the stairs, bare ass naked and I see through the curtains my in-laws walking toward the front door. I barely make it upstairs before the door opens…
We all have dinner, and a great time. Then Karen and I go to bed. But about 4 in the morning, I’m horny as fuck and can’t sleep. My wife also wakes up…We end up, after some preliminaries, having a really wonderful conversation while she holds me, me wearing one of my new little gay-boy outfits.
Yesterday with you I kind of made a break-through in understanding my different kinks and needs, and how they relate to my real relationship with my wife. I think the missing piece was figuring out that I NEED to be OWNED sexually by someone who doesn’t necessarily put out for me, but who can activate my sexual brain in that way. Since my wife has some physical/medical issues and isn’t a horny girl, this idea that she could arouse me with her playful brain was huge.
You did that for me so well, that it helped me to accept that this new thing was what I needed. It helps me get to that sub place where my hardened guy shell comes off and I can accept emotional intimacy.
M wife is so awesome, and loves me so much that I knew the only person holding me back was me. I told her my remaining secret fetishes (desire to be humiliated, forced to eat cum, suck a dick, be OWNED by her as a key-holder, and forced to dress up in totally gay outfits) and I told her that I love her (which I do).
It’s now 6:30. She had me make her some breakfast (no coffee). Then she went back to bed (loves her sleep).
In all seriousness you’ve been a great therapist for me this week. The money I’ve spent with you is one of the best investments I’ve made. And it was soooo fun as well.
I really did suck that tranny cock. And I would have totally done whatever else. But the time I just had with my wife (and all the fun things to come) was really what I needed.

Sissy Samantha

Princess Melissa Makes You Pose For Sissy Selfies

Filed Under Ass Loving Worship, Blackmailed By Melissa, Cuckold, jewish princess humiliation, Jewish Princess Mailbag, Jewish Sexpert, Major Niteflirt Loser, Phone Sex Email, Small Cock Humiliation, Tease And Denial, Total Sissy | Leave a Comment

Meet sissy Samantha isn’t he fabulous in his selfie shots for me! I love sissy selfies and having my beloved sissy boys dress up for me looking like the worst drag sissy bois ever. Sissy Samantha has the best sissy fantasy, what a total sissy pervert loser!

I have a recurring fantasy about being part of a neighborhood chastity and sex club. The wives run it of course.
The husbands are in chastity for 2 weeks before the meetings. They meet at one of the houses for a few drinks. Then the men draw a bead from a jar.
The color of the bead specifies who and what. One bead is for oral with another wife. Giving and receiving. Another is for straight sex. The third is for anal sex. The fourth is for a three way with two women.
But I want the last bead. That pink bead is clean up duty. He has to stay in chastoty, dress as a sissy slut and eat all the cum from every couple. Then his ass is taken by the two from the third room.
Afterwards he has to stay in chastoty until the next meeting. For the first two weeks he’s still on cleanup duty for anyone who asks.
I love that fantasy Princess Melissa so much.
Sissy Travis

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