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jerkoffcaps: Fuck yes I would… wish my wife would send me pics or vids while she’s out getting fucked… She knows I’m at home jerkin’ it fiendishly while she’s getting fucked…
Be careful what you wish for…
“I wish mine were that big.”“Don’t worry, Honey… Your Dad and I are more interested in your tight lil PUSS, than your growing boobs.”
I’ll bet you wish you had a pair like mine
You wish it was you sucking my sexy latina cock don’t you.
You wish you were this good baby.
I bet you wish it was you he was assfucking.
I wish your cock was bigger too…
Sometimes I wish I never broke up with my ex…
I wish I’d started fucking black guys ages ago.
Admit it, all you white bois wish you had a cute little asian tranny to suck off.
I just wish you were half the man he was…
xxx
Jada Fire sure got her wish (I know I spelled “Goddammit” wrong…complete oversight)**Gifs and caption done by me**
Don’t you wish you could fuck me in the ass, baby?
You wish, faggot.
Proper Phrasing: Always remember to word your wish carefully. Luckily, he did. Now he’ll be loved by thousands of men. After all, they’re people too. I just hope she can keep up. maybe if she took them three at a time.
Wish Granted: Have fun Carrie.
Can’t imagine a better wish fulfillment.
Well done caption. Kind of wish they hadn’t screwed up the lady’s eyes, though.
freakden: Is this your sissy wish? I bet it’s the wish of plenty of my fem sissies!
Sissy Andrea: Do you wish you had your dick in me?
hotnhardrod34: hotwendy79: Let other men help your wife. I wish my wife would allow other men to make her cum like never before
myslutywife: sharingthegirlfriend: Follow me on sharingthegirlfriend.tumblr.com I fucking wish! How cool would that be hisslutywife
jnailer46: gretchenplays: That’s right baby girl. That’s what I want you to do, and like it too. I truly wish my fiance wanted to do things like this
Well she’s an ex now but she knew and still does. I just wish she’ll send me pics when she gets laid.
cumforhenti: I wish I was her so bad. Walking across that noted rope as each notch pushed and dragged against my clit well others watched for their own pleasure..
peeisforpleasure: Okay, this is an experiment! Should I do more of these comic-style captions or not? Please be nice in your responses! I just thought I’d give it a shot. So, what do you think? Love it!
I wish this “gym class” had been on the schedule.
sexy-sissy-captions: Wish this happened to me in college!
letmebeyoursissy: oh how l wish this was me…….
“Ohmigawd, they’re so huge!” “I know, right?! I just wanna, like, lick ‘em!” *Giggle* “You probably can now! God, new dresses, new …um… personalities, new boobs! What else can your wishing stone
Don’t think of it as chastity. Think of it as three months of foreplay. Starting now. Caption Credit: Wish I could remember. I saw the three months of foreplay thing somewhere.
This is the key I’m going to make you wish you had used on that email you sent me requesting a relaxation of my rules for you. Caption Credit: Uxorious Husband
Hey hubby, it’s your Wonder Woman. Hope you like the selfie! Wish you were here! Of course you could be here … Just buy everything off my amazon wish list and I’ll unlock the front door and let you back in. Caption Credit:
You’ve been a very good slave hubby, and you deserve a treat. You may continue looking at me in this outfit as long as you wish. As long as it’s less than sixty seconds and then you continue with the housework. Caption Credit: Uxorious
Oh no, you don’t get to touch. It’s taken you six weeks of slavery to earn the right to look. It’ll take a lot longer than that to make up for saying you wished I didn’t hit you so hard. Caption Credit: Uxorious Husband
You’ve been a very good slave hubby, and you deserve a treat. You may continue looking at me in this outfit as long as you wish. As long as it’s less than sixty seconds and then you continue with the housework. | Caption Credit: Uxorious
Caption request: Goddess Candice is going to fuck you til you leak in your cage. Picture made by a fan who wished to be anonymous. Thanks for your submission!
Isn’t it great that she has so many wishes? How boring and sad would it be if she had no wishes at all and nothing to do for you.
Just before Christmas, I get two thousand followers. Thank you all for your support, and all my best wishes.Based on the caption “Hypnosis”, I made this drawing:
I can’t stop staring at him.Well I wish you would. I hardly even think about him anymore.How long has he been your chastity house boy / pool boy slave?I don’t know. He became less interesting after six months. If I let you take him home can we get
Are you a boy who’s dying to become a girl?Does the idea of being a feminized, submissive sissy excite you?Do you secretly wish that you could wear panties, high-heels, and makeup?Would you have sex with a man? Letting him use your body however
As Missy explained her new rules for you, all you could do was nod your head and agree to obey her wishes. She was beginning to get control over your mind, and you felt your will starting to bend to her power, and that’s how she wants you. Docile. Horny.
She wished her chaste boyfriend would stay locked up, teased and denied all weekend.Her wishes always come true.She has the key.
Once he opened the picture app and started it recording the video his Mistress required that he tell every woman he met who was wearing boots that he was locked in chastity and required by his Mistress to offer to fulfill any single wish the woman had.It
You can be honest with me.You wish your manhood was as big as this shifter.Truly, I do too. If it was, most likely it wouldn’t be locked up.
Hey hubby, it’s your Wonder Woman. Hope you like the selfie! Wish you were here! Of course you could be here … Just buy everything off my amazon wish list and I’ll unlock the front door and let you back in. | Caption Credit: Uxorious
Awww, does puppy wish I was licking something else? Keep dreaming puppy – it’s never going to happen. | Caption Credit: Crystal Chastity
This is the key I’m going to make you wish you had used on that email you sent me requesting a relaxation of my rules for you. | Caption Credit: Uxorious Husband
flr-captions: This is the key I’m going to make you wish you had used on that email you sent me requesting a relaxation of my rules for you. | Caption Credit: Uxorious Husband
Belen Rodrigez - Pin Up Stars. ♥ Caption - “Mmmh I’d go lesbo for those!” Feel free to add your own caption if you wish. ♥
mysissyfem: I rely upon my followers for support - if you wish to be trained by me as a supreme sissy slut or send me a gift please send me an email at MistressJade@SissyFem.com ALSO - to purchase High Quality Breast Forms endorsed by ME, please visit
captionsofchastity: Oh, but I do wish I could do what Mr. Black does! Http://chastity-captions.tumblr.com
chasteslut: One of my absolute favorite captions, I had the chance once to lick up my mess off an exes feet and chickened out…wish I could go back. Http://chastity-captions.tumblr.com
Wish to be chastised
Wishing My Wife Would Lead Me Down A FLR
