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This is my 100th, caption, so I figure it’s a good time for another true story. My wife doesn’t usually like the taste of cum, but several years ago she met this guy whose cum was delicious, she said. She really did ask him how he got it to

This challenge has been won by: intheshadowofmyballs!

This challenge has been won by: hillary-scott!

This image has been submitted by: slutswhos!

This challenge has been sent in by: moolagoon!

This challenge has been won by: lilslutmouth!

This is how itâ€™s going to be, this is the way it has to be. <3

This one was written by my hubby!

We were out for adult fun, but this wasn’t what I anticipated.Â It was my bachelorette party with all my friends and my mom.Â My dad suddenlyÂ appeared out of the crowd and paid for a lap dance with my mom!Â Oh, my god, she got so flustered.Â

This is going to take some getting used to.

This is where your brothers big cock went…

This is the best feeling

This is the CLOSEST you’ll get to pussy EVER AGAIN.

This has been fueling my sissy cummies lately. I’d like to write a short story expanding on this. This caption most perfectly captures the satisfaction a female dominant gets purely from humiliating and emasculating a man, especially a wife doing it

This was one of the first captions I seen when the only sissy thing about me was dressing up, nothing more. I said “Yeah, right!” at first, but this caption started turning me on the more I’d see it. Then I found FemSissy.com and now I’m just

This is another of those ideas that I think could really catch on, and spread the word. So if there are any independent sex toy party consultants (who are not forced to buy only from one company) give it some thought. Contact me for more ideas about how

This isn’t as far fetched as you might think when you realize how much the courts have ruled that an employee has little or no expectation of privacy at work from their employer.

This should be an “interesting” conversation.

This works too.

This would be one of those times when you need to focus on the loveliness of pussy.

gaycurioussissy: bellesnewboots: mysissycaptions: What do you say sissy? This might be the best caption I’ve ever read. Not just original content but also a really eloquent and appropriate style. Way above the regular Tumblr standard. Sold!pandora

sissiestaci: complete-feminized: sissyjessica42: This picset made me whimper and my clitty throb OMG - so hot! Mistress will put me in chastity - and I can´t wait for it. See my own pix at: http://complete-feminized.tumblr.com Love

Not sure if you’re still looking for picture submissions. Here you go, either way. I’d LOVE more submissions. This is an open call to anybody, send me a pic, and I’ll rapid fire caption it for you! ***** “Your hair and makeup is flawless

if you’re still taking pic I sure am! Keep them coming! Hrm… I’m fairly certain I’ve used this picture before. Or at the very least, I’ve contemplated using this before. I can’t seem to find it anywhere though…

This is a very truthful caption. We counted and that number blew us away. A large portion of that number came after my entry.

Caption/image credit (possibly not original) http://contemplatingthedivine.blogspot.co.uk/2011/02/captions-to-contemplate.html?zx=925d615c5716adca God I love this caption. I was trying to get something like this and may make another attempt in the

This is what I want you to be thinking about tonight when I go out with my girlfriends. If the house isn’t better than spotless when I get back, this is the last sight you’ll have of my lingerie for a long time. Caption Credit: Uxorious Husba

This is the one! The pan whose bottom he burnt with last night’s dinner. I always love the punishment to fit the crime. So I’ll use this pan. “HOOONNNEEEYYY! Get into the garage and over the spanking bench.” Caption credit:

This caption sort of violates my rule that the voice of these captions is always one woman somehow domineering a man, since in this case, two women can be heard. On the other hand, I guess no one else cares about my self-imposed rules.

This is caption number 256, or 2^2^3; I don’t care much about decimal numbers, but I occasionally recognize binary anniversaries. So you could say that the number of my captions is increasing, not shrinking, even if shrinkage is the connecting theme

This captions is called “Another Proposal”, since I already had a caption titled “The Proposal”.

This caption is partly inspired by the ecchi manga/anime “He is my Master”. Which has it’s own hentai parody/pastiche “This is my Chastity Belt” (”Kore Ga Watashi No Teisoutai“ and “Kore Ga Watashi No Teisoutai Plus!”, if you want to

This is one of those images I copied to my “potential captions” folder, where it sat for ages: it’s a great image of a beautiful woman, but no caption I could think of was doing it justice. I’m still not sure if I nailed it.

This caption was a nice opportunity to showcase different devices, and her silver top goes nicely with all this steel, so I’m quite satisfied how this caption turned out aesthetically.

This caption is a tad bit on the longish side; even if other captionists occasionally use even longer texts, one of my rules for these captions is that they shouldn’t be “too long”. I never codified what constitutes “too long”, but after a thousand

This is one of those captions where I spent a lot of work without being satisfied with the result. I wanted to get across that there is this barely-hidden rift within the spacetime-continuum that leads to this strange, sexy otherworld, but that the rift

This goddess is more than happy to tease in front of a crowd down at the local pool. She totally knows you’re sex life is handsex only! Of course, everyone started laughing when you popped a little stiffie in your swim trucks as she humiliated you in

This is an interracial caption story entitled Daddy. It has too many frames to be contained in one post here. So here it is on my other blog… Daddy

I’m sorry, but I forgot to make a post detailing the scheduled releases for November. This post is to rectify that mistake. Better late than never, I suppose. This month’s first release was “Sharmuta” (11-7-17), which starred

This lil’ sissy not only has her clitty locked up but is secured in a cage! Wonder what plans are in store for her. One thing is known: There is no escape from her fate. She is a sissy 4 life.~ Subscribe to Sissy Princess on Patreon for original sissy

Caption this!!!

captioned-vines: tahreza: when shes like “that one is” its the cutest thing in the world and its also me Boyfriend: [mumbles] “That’s sensational.” Girlfriend: “Actually, that’s not my favorite highlighter.” Boyfriend: “It’s not?”

This memory, this image, of the neighborhood girls smiling and laughing at my unexpected erection followed shortly by my very first cum – right in my pants, right there in front of them – seems to have modeled my behavior ever since.I constantly seek

This is your reward. For all your housework, giving me endless orgasms, handing over all your pay to me, for taking my punishments. This is your reward. You’re allowed to look at me. | Caption Credit: Uxorious Husband

This is what I want you to be thinking about tonight when I go out with my girlfriends. If the house isn’t better than spotless when I get back, this is the last sight you’ll have of my lingerie for a long time. | Caption Credit: Uxorious Husband

captioned-femdom-situations: A little more than four years, a little less than 9.000 posts: This is a remarkable day. Without a doubt, femdom captions can be called an established segment - 10.000 followers can´t be all wrong. Thank you all, followers

trance and dance

kn0wy0u: Alexandra Daddario @ kn0wy0u.tumblr.com

Mr Random Thoughts

redhead-beauties:Redhead http://redhead-beauties.blogspot.com/

redhead-beauties: Redhead

redhead-beauties: Redhead

CAPTION THIS ٩(◕‿◕｡)۶

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