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Magical Items: If you are lucky enough to run across one of these then for gods sake, don’t leave it just anywhere! Lock that sucker up in an safe or something.
High School Again?: If you’re extremely lucky, you might get another chance to get things right.
The Trap: You should have known she put those clothes in there just for you, sweetie. Welcome to your new room. And don’t worry about all your nasty man clothes; she’s already thrown them out. Enjoy your new life of servitude, you lucky sissy.
Satisfying Your Benefactor: Even if you’re in a rush to make the bus to school, you’ll always have time to take care of your duties. Maybe if you’re lucky you’ll be late and have to explain things to the Headmaster. He always gives
Turned Out: Sometimes you get lucky and your wife accepts who you are, and sometimes you get even luckier and she doesn’t. Then you wind up with your new master.
Kevin, you insanely lucky bastard!
Job Satisfaction: We should all be so lucky to have a job that we’re happy and very talented in doing!
I have a feeling someone is going to be stripping in the near future. Lucky girl.
vanilla-chastity: When you tried to resign as my assistant last year I gave you a choice: Quit and I’ll give you a reference so bad, you’ll be lucky to work for minimum wage.Or, stay and be my chastity boytoy for a year, after which I’ll let
Haylie had been saving herself for marriage. She told Brad that when they met. She told herself she was lucky to find a man that understood that, especially today. Occasionally he would make suggestions but would apologize when he got shot down.She was
You’re lucky you are fairly tan already Charlie, otherwise those ropes would leave some pretty messy lines on you. And we need you looking your best for Friday.
buff357: Dominated! Lucky bastard!
francieum: tayyzilla: THIS GIRL AT MY SCHOOL IS PREGNANT AND SHE POSTED THIS AND CAPTIONED IT ”♥HIS TOUNG IS OUT♥” BITCH DO YOU NOT SEE THAT IS A DEMON THE GRUDGE IS IN YOUR STOMACH Actually, it’s in her uterus.
locked2012: Only if you are lucky.. cause that can also be torture if done right.. so close but so far away..
artsubbie: blueballs1629: My keyholder is giving me a taste of long term chastity! We are lucky i put on whichever cage She picks for me daily and may get to come every 100 daysif She allows
13 is unlucky for some but lucky for me. I’m thrilled to have 13 followers so thanks! I love it if you love my posts with the little heart button, whether they are ones I’ve reblogged or original. But that doesn’t matter, it’s
You’re quite lucky that she’s so lenient.
You’re quite lucky that she’s so sensible and saves you from most of your crazy ideas your constant horniness makes so appealing of you. She talks you out of most of them, except those she finds herself amusing.
The armadillo isn’t photoshopped in (at least not by me), so the image is quite a lucky find. The German word for armadillo, by the way, is “Gürteltier”, which literally means “belt animal”, and for someone obsessed with chastity belts, the
You lucky guy: instead of your girlfriend spending your money left and right, she looks for bargains. I think she’s a keeper.
You’re such a lucky guy that you have such a polite girlfriend.
A ratio of merely 100 to 1? You lucky bastard!
This must be your lucky day: you don’t get eaten by the sea monster and you finally meet a girl who’s into chastity play.Unless you have a fetish of being eaten by sea monsters.
You lucky boy: she just called you her favorite sex-slave.
I think your husbands are the lucky ones. Compared to other men.
Your girlfriend is quite lucky that her girlfriend isn’t requesting anything more valuable.
You’re a lucky guy, she’s showing you the strap while wearing it.
Eliza Dushku’s boyfriend must be a lucky guy.
Aren’t you lucky that she’s so easily entertained?
It’s your lucky day, you’re allowed to watch them joking around.
With a deck full of cards reading “permanent chastity”, “castration”, “penectomy” or “40 years of chastity”, you are quite lucky.On the other hand, with a deck full of cards reading “one day of chastity”, “light flogging” or “an
Let’s put him back in his prison, ok?Ten minutes are more than enough for one month. You can consider you a lucky guy anyway: Other keyholders don’t even allow ten minutes!
Do you remember when we made this silicone cast of your cock one year ago? Right before you put it in the CB-6000 and gave me the only key? I can’t imagine how lucky it would make you if it was able to grow this big ever again…Anyways…
Do you think we schould let him have at least a boner for a few minutes?—-Hell no! The deal is that he stays locked until this vacation is over. It’s not our problem that he was ok with paying for everything for one month in advance. He’s lucky
chien-espagnol: What I wore to last night’s @tdgpresents Winter Quarterly ~please leave caption
You should consider yourself lucky that she has suspended you so high that she can’t get her heels in your butt.I imagine she will think of something else.
She loved visiting historical sites.Her interest had lately included collecting historical artifacts.Medieval chastity devices were particularly interesting when used in historical locations.Aren’t you the lucky one?
vanilla-chastity: When you said you wanted to “try” male chastity for a while, I knew you were asking me to lock your orgasms away forever. Lucky for you, I’m all too willing to ensure you never come again.
ramennochibi: More captions here
squidwardelric: I’M SORRY I FOUND THE PICTURE AND COULD NOT RESIST PUTTING THAT CAPTION. PLEASE SPARE ME.
unicornsarecooler: niamhtumbly: Stop trying to make fetch happen. Fetch is never going to happen. I literally cannot stop laughing at that caption
rebel-in-overalls: Because everyone needs more baby bunnies in their lives. Also, I spent time on the captions, you should look at them.
carryonmy-assbutt: imanassbutt: owlishnaiad: Sometimes infomercials make me question the fate of humanity. Other times they just make me laugh hysterically. DID NO ONE READ THE CAPTIONS OR
whatwouldcapdo: dangit-jim: shredded-sorostitute: confusingeuphoria: howellama: book-titles-for-band-names: unic0rrn-****s: this doesnt even need a caption… every girl knows what this is… IT’S BACK. IT’S FINALLY BACK. ITS BAAAAAACK of
everythingelsegoesherethen: yencid: me on my way to your bed. There will never be a better caption for this
hindre: leonkuwatas: youreouttayourtree: ladies dont start fights, but they can finish them. that is a cat with a hairbow how is that relevant to the caption
vipertruck99: Is this a caption contest?
malkatz: spotthelooney: IT’S 1:19 A.M. MY COUSIN JUST SENT ME THIS PICTURE WITH NO CAPTION I’M FREAKING THE FUCK OUT “butter me up, sunshine”
anythingfeline: Photos by John&Fish (flickr) Captioned photos. [x] [x] [x] [x] [x] Please DO NOT remove photos’ source links.
madame-loki: nerdywithadashofawesome: paintedprintedpaper: moonlightmina13: gayteenss: wetpaintanddrynoise: thatfuckingcrowv2: unic0rrn-sluts: this doesnt even need a caption… every girl knows what this is… Acurate. Actually today. Yes
claykaczmarek-y: i sent this photo to one of my friends with the caption ‘motherfuckin bubbles. you best envy me’ and all he did was reply with ‘ARE YOU NAKED????’ i was like, ‘what??????????no???’ ‘who the fuck takes a bath naked
the-toxic-mermaid: madame-loki: nerdywithadashofawesome: paintedprintedpaper: moonlightmina13: gayteenss: wetpaintanddrynoise: thatfuckingcrowv2: unic0rrn-sluts: this doesnt even need a caption… every girl knows what this is… Acurate. Actually
the-tabularium: ilovejohnmurphy: corntroversy: toushindai: [video: a person twirls an anime keychain above a number of chicks and creates a chick vortex] why did this need to be captioned so u can decide when it’s not loading whether or not it’s
spider-manofficial: hindre: leonkuwatas: youreouttayourtree: ladies dont start fights, but they can finish them. that is a cat with a hairbow how is that relevant to the caption Uncultured swine
robotseverywhere: wendycorduroy: here’s all my fave out of context lines from the pokemon episode “ghost at maiden’s peak,” more colloquially known as “eric stuart tries to fuck a rock” i worked really hard captioning this one as you can
cipheramnesia: wodneswynn: captn-sara-holmes: happifying-things: hyperspeed 🎥 by 5frogmargin It’s literally captioned hyperspeed and I was still not ready 😂 He hungy how Muppets eat
cafe–gay: grim-anatomist: When you see a really good post but there’s some form of guilt tripping to reblog it added on at the end (ID: A screenshot of Marge from the Simpsons looking dismally at the camera with one arm raised. A caption underneath
submissivegames:It will be your little secret. Only She will know about it. Locked in place, hidden away. All of your friends think you are so lucky, having this beautiful girlfriend that points out other beautiful women to you. It must be great,
cherishmyslave: You are one lucky slut….
![anythingfeline: Photos by John&Fish (flickr) Captioned photos. [x] [x] [x] [x] [x] Please DO NOT remove photos’ source links.](https://69.media.tumblr.com/5a77c702b8ef3d2800330bab793ae556/tumblr_n0rl2fOkEQ1s4at2ao1_250.png)
![the-tabularium: ilovejohnmurphy: corntroversy: toushindai: [video: a person twirls an anime keychain above a number of chicks and creates a chick vortex] why did this need to be captioned so u can decide when it’s not loading whether or not it’s](https://40.media.tumblr.com/avatar_3cafb283565d_128.png){kind=avatar}
