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Can you please find a way to get Lisa Edelstein into an I decide caption.
Once freshly milked put your sissymaid in chastity so she can’t play with “your” toy when she’s working.
rohosub: Prostate milking is necessary during long term chastity. Here is a short blog entry on how we do it. Or at least how we did it before the anal orgasm. From my wife’s blog: Last weekend, March 9th 2013 to be exact, I reached a milestone in
malevalsmistress: Episode 311 Milking me once a month is my treat if I have been a perfect slave - but if this is a treat it is seldom something to anticipate with relish- unless the relish is liking the taste of my own ejaculate. My Manageresstress
Dear Diary I: Acceptance
Seriously?: I mean, what the hell? You can’t expect a sexy redheaded femme-boi to not fuck your husband if you don’t give her some relief every now and again. That’s what milking is for. Come on Mom, you know better!
The trials and tribulations of a kept sissy-slut.
Sometimes your keyholder has other plans for the evening. That leaves your weekly milking to you. You’ve been teased mercilessly for the last week and you’re fit to burst. What’s it going to be, sissy? Real cock or even more pain?
forfet-ishe: #Femdom #Mistress #Chastity #Milking
ilovesuckintrannycock: forfet-ishe: #Femdom #Mistress #Milking #Chastity Thankyou Mistress!! I love you sooo much!❤️❤️
slavewade:boysmakegreatpets: Wow, milking in chastity! What a humiliated bitch he’ll be…. www.FemdomEmpire.com
eternallyedged: “I wonder if I actually need to take the cage off to milk him…” Sarah wondered to herself. Turning on her Hitachi wand she pressed it firmly against his cage, watching intently as her little experiment played out before her…
forfet-ishe: #Femdom #Mistress #Tease and Denial #MIlking #Chastity
slavewade: So lucky to have Mistress T use me as Her asswipe to inspire my pathetic chastity milking session. Of course She ruined my orgasm in the end!www.FemdomEmpire.com
teasingdenialandruinedorgasms: When I finally did get to cum, being forced to have my balls milked without even being able to get hard is perfectly cruel.
neocoronaau: Ah just a quick thought, I happen to know not everyone likes text on their images so just as a little fanservice here are some textless versions of the three bonus images, enjoy! I love this guy to bits!Mostly just wanted the image in
she’s on a tight schedule. 5 more sissies to milk before lunch
Here is my little tiny sissy clit. Mistress “W” keeps my tiny little clit always locked up. She says that a sissy little clit that small must be locked 24/7 and she milks my prostate because she doesn’t want my little clit getting hard or enjoy
Oh my!!! Day 14 chaste and I can now milk myself from my prostate toys!!
otk503dd: servus-m: “Wie oft onaniert er täglich, sagten Sie??” “How often he masturbated every day, you said?” he’ll be much happier in the long run when he’s been castrated,the chastity,milkings and the stable mistresses liberal use
slvboby: Femdom 0656 #femdom #mistress #slave #chastity #milking @rebeca_rebel
xxx
cocklockedslavehubby: mistresss35: slavewade: The dreaded chastity milking means my weenie does not ever need to be unlocked. i miss the feeling of an erection…www.FemdomEmpire.com cocklockedslavehubby mistresss35 favorite way to ruin. But she
slavewade: Mistress Tiffany proves her cockteasing skills for a rare out of chastity milking. These gifs dont do justice to just how torturously slow and cruel her expert teasing was all the way to the ruined ending. www.FemdomEmpire.com
slavewade: Mistress Chanel said for my chastity milking She would actually let my weenie enter Her divine pussy if i could hold out while She warmed it up. Loser me blew my load and my chance in seconds… www.FemdomEmpire.com
slavewade: The dreaded chastity milking means my weenie does not ever need to be unlocked. i miss the feeling of an erection…www.FemdomEmpire.com
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I think you’re ready, pet. For today’s milking, you’ll wear the hood. Just be sure to focus on your breathing. You’ll be fine.Do this for me. Suffer. Maybe I will let you out next month. Maybe.
Mmmphh. Listening to him suffering on the milking machine is wearing me out. So many months caged and now he’s had 7 orgasms in a row. I vibed myself to a dozen of my own at first, but now… I am worn the fuck out. May need a tiny nap. Then I’ll
Congratulations! Your good behavior has earned you another orgasm.What? No, of course I’m not going to unlock you early just so you can have it!We’ll just give you all three of the orgasms you’ve earned next month. It’s not a problem for the milking
slavewade: It has been weeks since i was last allowed to cum and Goddess Tangent has me helplessly mummy wrapped for my chastity milking. She takes Her sweet time, bringing me right to the edge over and over while She makes fun of my pathetic helplessness
August 17, 2014 12:32 am Day 13 Walden, Eastern United States Going to bed, so keeping this short. That huge dildo? Just fucked myself with it. Again. Deeper than last night. And managed to milk out some cum. Again. This is the first time I’ve been
Got Milked?No day is complete without a little bit of dairy.
maledenial: MaleDenial original.
ridder85: Miss had lots of fun.. After that she milked me with cumming!! Next morning back in cage #chastity #milked #Femdom #slave #submissive #blueballs
forfet-ishe: #femdom #chastity #milking #torture #mistress #slave
slavewade:So lucky to have Mistress T use me as Her asswipe to inspire my pathetic chastity milking session. Of course She ruined my orgasm in the end!www.FemdomEmpire.com
Another bonus caption, this one by request!
So long denied, and we shall sacrifice it. Yes, your orgasm will serve as an offering to the devil on my behalf.I shall ruin you twice. The milk the rest out. Then cage you up again, for the next ritual.
Recipe for a perfect slave:ChastityMilkingMake him swallow itBrief releaseMore chastityPegging.…and a cane, if needed.
Ungrateful of you to complain now. I did unlock you. That milking machine is going to force an orgasm from you.Yes, the penis plug is going to ensure you regret it.But I MUST use it, so that you’ll learn.
Shh, almost done now. It’s okay. The milking machine wears you out so nicely.You won’t fight at all while I lock the cage back onto your cock.
It’s called a humbler. Aptly named, isn’t it? Crawl up the stairs. I’m gonna milk your sore cock once you get up here.Teach you not to beg me for release again.
Your balls are so blue. Your face is so red. Keep it up! Ride that plug until it dribbles all over you.Your silly request for release from your chastity is denied. YOU are denied. You’ll stay that way.Ache & suffer.
It’s time for your monthly milking, Prisoner 734. Am I going to need to restrain you this time? Are you gonna cry again?Considering your behavior last time, I’ve decided not to bother with cage removal.
After over a year of him being locked months at a time, prostate-milked, cage-drained, and even given one nasty ball-punch ruined hand-job, I finally let him fuck me and orgasm.Now I am truly a goddess to him. Just one real orgasm. In a year.
Already milked you with a strap-on and made you spurt with a hitachi on your balls. You’d best think up more amusing ways to get relief.We’re not doing repeats & it’s only cage ruins I’m giving for a long time.
I am an artist of denial, & you, my milked & dribbling boy, are my finest work.Just a metal cage to compress your still-leaking cock, and… **kiss** perfect agony.
If he wants out & starts to beg,you make sure he gets the peg.If he gets mad & starts to rage,you lock him in a tighter cage.You gave him chores. He just did… some?Milk that bitch. Force-feed him cum.A boy is a slave you need to train.For
He said there’s nothing more humiliating than cumming into his own mouth.So I said, “Let’s lock you in chastity & later prostate milk you until it all dribbles into your mouth.”
I know it’s actually called the P-spot, but I think of it as the C-spot.Because it allows me to keep him Caged in Continuous Chastity, all that filthy goo drained out of him.
A prostate-only orgasm will make him obedient.If the chastity isn’t fast enough for your training needs, drain him without release.
So which tastes better? Thick cum from when I gave you that prostate milking? Or the dribbly stuff from my eventual ruin after that endless edging?Or is it the cum form a simple, full orgasm? The kind you used to get before you gave me your key? You
Have you ever been ruthlessly milked of every drop, one long continuous ruined orgasm session designed to amplify your horniness without letting you have the pleasure?No? Well, I just want you to start imagining the suffering. Because it IS what’ll
Prostate milking manual
kinkycouple30: I’m not a big fan of gif’s, but this surely hit some nerve. What would be more humiliating and destructive after a weeks in chastity. Being in humiliating position, being milked without “proper” release, when there is no more cum
