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pupjosh: Back in my cage, going for a new record past 10 days. I have more free time now to use my toys. Iâ€™m getting closer to prostate orgasm. Thatâ€™ll make being locked way way easier. Anyone have suggestions of how to train my nipples or videos

slave-dildosox: Fuck your ass until your dick reacts to it.

Brenda Song Monthly prostate milkings with the tube left on eliminate health concerns meaning the chastity tube can stay on permanently.

Milking and PeggingHis body must get used to the new situation. Receiving the strap-on will change from being painful, to being uncomfortable, and finally just a strange sensation.Take your time in order to stimulate his prostate when you are fucking

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

Prostate Milking: Milk that sissy bitch! Milk her hard!

how humiliating

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!!

chastityboy6969:Chastity tears. Useless locked clitty leaking and bouncing around while I take my dildo.

cumdenial: when the prostate is overfilled, it is oversensitive and prone to triggering an unauthorized ejaculation, even when the bull is locked in chastity. prostate milkings should be scheduled regularly to prevent this. through regular milking, the

PROSTATE MASSAGE/MILKING

new-chastity-male: The Milkman Cometh Marathon milking session in chastity - part 1 It was a lazy afternoon and I was really horny, so I had to do something. Milking my prostate with my dildo while locked in my CB6000s. A LOT of prostate milk was the

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readyifyouare: clevelandfag: skin2bound: rohosub: “Chastity Tears” are pretty common when you’re locked up in long term chastity. The “tears” are actually a rather constant seeping of pre-cum when you are horny as a result of your prostate

boiclitty: fetishvideos: handsfree-cum: heelfetish: A perfect sissygasm while locked in chastity Very nice handsfree prostate orgasm of a sissy in chastity Here’s one of my original vids from before I deleted my old account

Drippy cummies are the best cummies! ^_^

Überkinky have asked me to tell you about their great selection of chastity devices. Go check them out, if you buy anything from them using the link below, you will be supporting the blog. https://affiliates.uberkinky.co.uk/scripts/click.php?acc=59ca20b

married-and-caged3429: Mistress said this wouldn’t work my cock is to small to hit my prostate. That’s humiliating enough she says

Challenge: Dont cum until you’ve learnt to cum anally!

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supermilker69: Oiled, caged, cock locked in chastity before my prostate milking. It’s a good thing she allows me the honor of eating up all of my own cum!

daddyboybreeder: my boy has been in chastity since MondayToday I release him, stopped his habitual masturbation for a couple daysI will breed him and hopefully make him cum anallyhis prostate will be ready

cagedbitchformistress: Friday at the office caged and panties as always but today during lunch. A vibrating prostate massager while at my desk for Mistress. Making her caged cock all nice and wet for her.

lukeblogit: prostate milking…

fitbicouple: http://www.fitbicouple.tumblr.com Hubby’s first hands free prostate orgasm while caged. Part 2 @fitbicouple original content

lockedcumslave:cool.

That i can confirm😈😈💦💦💦🔐🔐

belocked:rohosub: Prostate milking in chastity. This is the only way you should milk a sub with chastity device: Prostate simulation

laxus-usually: sissysubdenise: u know u want to!! The good news is that if u have a healthy prostate then u are totally capable of achieving a prostate orgasm or “sissygasm” … u can even remain locked in chastity and cum from nothing more than

sissysubdenise: u know u want to!! The good news is that if u have a healthy prostate then u are totally capable of achieving a prostate orgasm or “sissygasm” … u can even remain locked in chastity and cum from nothing more than anal penetration.

skin2bound: rohosub: “Chastity Tears” are pretty common when you’re locked up in long term chastity. The “tears” are actually a rather constant seeping of pre-cum when you are horny as a result of your prostate and seminal vesicles being

boiclitty: fetishvideos: handsfree-cum: heelfetish: A perfect sissygasm while locked in chastity Very nice handsfree prostate orgasm of a sissy in chastity Here’s one of my original vids from before I deleted my old account

boiclitty: fetishvideos: handsfree-cum: heelfetish: A perfect sissygasm while locked in chastity Very nice handsfree prostate orgasm of a sissy in chastity Here’s one of my original vids from before I deleted my old account

thesmuttyrogue:Here is the final piece ‘chastity 101′. A busty teacher informs her pupils on the wonders of chastity and how to go about it the right way. Of course it involves keyholding, prostate milking and being a slut! I feel like this could

prostate-milking: Obedient sissy sluttyboy anal prostate milking massage in chastity cage gif

twinktop: “Chastity Tears” are pretty common when you’re locked up in long term chastity. The “tears” are actually a rather constant seeping of pre-cum when you are horny as a result of your prostate and seminal vesicles being full and almost

A tighter cage? Sharper spikes? A slow & proper prostate milking?Diabolical CBT? Swift ball-kicking? Urethral sounding? Want to go for a humbler crawl?Tell me what you need, baby. I’m here for you. Here to watch you suffer till you BREAK.…and

Prostate milking, ball punching just when you get there, or abandoning. Oh, or using a sound to draw it all out pleasure-free…There are so many ways to drain that cock.Chastity would be a mercy.

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.

All you need is a strap-on. You can wear it to tap that prostate and empty his balls when they get swollen. He can wear it when you feel like getting fucking pounded.He doesn’t need to come out. Ever.

Give a boy a prostate orgasm, and you own him.Give him a prostate orgasm through his cage, and you utterly break him.Take this position while asking him if he’d like to have anal sex? Words can’t express what it does to him when you bend him

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.”

Oh, I’m not JUST going to make you spurt past your chastity cage when I strap-on fuck you. I want to fuck you beyond reason.I’m going to bruise your prostate, flatten each wrinkle inside your ass, & hollow out your mind itself.I’ll

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

Three weeks, and you spent most of it begging for release. You need to surrender.But fine. If you need me to drive it home for you, I will. Literally drive my strap-on into that prostate until we empty you. Without release!I will expect a better, truer

Until he’s had a prostate orgasm through his cage, a man does not know true submission.That’s also when to tell him he’ll be locked much longer.

Prostate milking manual

Male Chastity Prostate Milking (Massage) - XTube Porn Video - iltep999

hardmasterfist-sissytraining:A proper prostate Milking ( while in Chastity )1. Insert Large Butt Plug to apply pressure on the prostate. 2. With subject laying on their back and legs spread open place Vibrator behind subjects penis. 3. Apply pressure

hardmasterfist-sissytraining:A proper prostate Milking ( while in Chastity )1. Insert Large Butt Plug to apply pressure on the prostate. 2. With subject laying on their back and legs spread open place Vibrator behind subjects penis. 3. Apply pressure

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