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Femdom Sissy Captions @femdomsissy

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A place for sissy, chastity, femdom, pegging captions and the like. Stuff I love mostly with women and sissies :) - Femdom Sissy Captions (@femdomsissy)
Feminization signs you have become a sissy you @femdomsissy


Signs you have become a sissy: You have a closet full of high heels!

Sluttymascha a few chastity pictures hope you @femdomsissy


A few chastity pictures - hope you like it <3 :)

Not4davey handcuffed to the patio railings bare @femdomsissy


Handcuffed to the patio railings bare ass naked except for a cock cage. There is a first time for everything.

Not4davey your next assignment is to tell your @femdomsissy


Your next assignment is to tell your husband all about me. And then deliver him to me wearing a chastity cage and nothing else. And then I shall instruct you in the fine art of controlling a male.

Totalsissygirl both please @femdomsissy


Both please!

Ilovesuckintrannycock lucky hubbys @femdomsissy


Lucky hubby’s!!❤️❤️

Deviantdominantdesires cherishmyslave why @femdomsissy



Why not tease it if you lock it up?


Thesissywalrusking who needs pussy when you @femdomsissy


Who needs pussy when you have a sissy

Wantingthis do you miss doing this to your @femdomsissy


Do you miss doing this to your little thing? Yeah I bet you do. Stroking it when ever where ever you wanted. You know that fantasy you always had while pulling on your little thing. The one where you would bend me over and just take my ass? Well it’s time it came true….but with a little twist….That’s right slut BEND OVER!

Mastershango the black owned take over @femdomsissy


- The BLACK-OWNED Take-Over:

“You look at your wife every day, and you love her very much as you did the time you first met her.  And when you made her your wife.  But you no longer see her as before.  Now you see her to be another man’s property.”

Master SHANGO.   

Route82 the first six months or so it was @femdomsissy


“The first six months or so, it was difficult, mostly because as a masculine hetrosexual, he resisted and felt humiliated by it. He also had to learn how to relax, how to breathe, how to “push out” on it rather than tighten up. But once he understood and accepted that getting the strap-on was going to be a regular part of his experience, and I had established my authority in that regard, it’s been interesting to me how easily my hubby’s adjusted to take even my biggest, thickest strap-on dildo.”

Text borrowed from FemdomHotwifeCuckoldInterracial here at Tumblr.

Sissy maker sissyreaper sissy reaper @femdomsissy



Sissy Reaper … More Gay every day …

Boy to Girl Change with the Sissy-Maker

Captionsofchastity shes a natural its so @femdomsissy


She’s a natural. It’s so nonchalant how she adds a tiny bit of humiliation…

Sissy maker sissyreaper sissy reaper @femdomsissy



Sissy Reaper … More Gay every day …

Boy to Girl Change with the Sissy-Maker

Totallyfem loads of fun for tgirls @femdomsissy


Loads of fun for tgirls #crossdressing #ladyboy #shemale #sissy

Swrredhead oh i hope he likes my pretty dress @femdomsissy


Oh I hope he likes my pretty dress and my wonderful girl cock. Do you think he will let me, you know, cum all over him after I fuck him?  Do you like my pretty girl cock?

more futa by request

Captionsofchastity why not do simply everything @femdomsissy


Why not do simply everything for her?

Captionsofchastity it looks like shes learned @femdomsissy


It looks like she’s learned from life. But her ex-boyfriends have missed out on something :-)

Sissydonna i want to be a girl pink @femdomsissy



Pink, please.

Where Boys Will Be Girls

Danigirlnyc or locked away @femdomsissy


Or locked away ☺️

Sissy maker sissy stable and dont forget @femdomsissy



.. and don’t forget a locked clitty ! :)

Boy to Girl Change with the Sissy-Maker

Straponmodel thenewlovetobepegged @femdomsissy




daemonsseductress My Beautiful Seductress


Don’t keep her waiting…..

Sissyreaper sissy reaper more gay every day @femdomsissy


Sissy Reaper … More Gay every day …

Cuckoldhusbandobediencetraining @femdomsissy



Another very effective milking technique to drive a man insane with desire.  You just have to be careful that you never, ever touch the head of his penis.  It’ll be extremely sensitive, and if you touch it, he’s likely to instantly explode with orgasm. You can grab hold of the shaft of his penis, and even stroke it a bit, just don’t touch the head or anywhere near it.  If a man has a small penis, like my hubby’s, it might mean that you don’t touch his penis at all.

The idea is to not let him cum, and prolong the session.  Drag it out.  Take your time.  Relish in his frustration, his desperate pleas, and erotic suffering.  You just slowly massage his prostate with your finger… you kind of flick your finger up like you’re saying “come here”, or you can use a special dildo called an Andros that has a special curve and a knob on the end that is designed to hit his prostate just right… and do it until his penis starts leaking semen. 

That’s how you milk his balls.  Once his penis starts leaking… and it will typically leak out slowly in small drips and dribbles… you just keep milking him like that until it empties his balls.  Typically it might take 20-30 minutes.  You’ll be amazed at how much cum leaks out.  It’s kinda freaky.

With enough experience… and a little technique and patience… you can actually “milk him” by fucking him with a strap-on.  The best strap-on to use for this purpose is a medium size one that has a bit of a curve to it and has a big head but has a thinner shaft behind the head so the head stays in his ass and hits his prostate while you fuck him with it. 

I’ve learned how to milk my hubby’s balls quite effectively this way.  But it took a while to get the technique just right. Now, after a good strap-on session, there’s usually a large wet puddle of sticky goo underneath him where it’s all leaked out. 

But strangely, he doesn’t really cum that way, it’s not like a real orgasm where he spurts his cum all over.  To hear him describe it, and from what I’ve read about it, it’s not really sexually pleasurable for a man.  It’s more frustrating than pleasurable.  Like intensely frustrating.  My hubby describes it as getting close to cumming… getting close… getting close… getting really close… and then “OH FUCK!”… not being able to cum. 

All of which, of course, keeps him on edge and wanting to please me.  You should see how anxious he is to lick out my cunt after a good strap-on session.  Like he’s never tasted pussy before, and can’t get enough. 

Believe me, when he’s in that “zone”, he’ll pretty much do anything for you, especially if you give him the idea that you’ll let him cum if he does.  That’s usually when I like to tease my hubby about some of my wilder fantasies. 

“Are you gonna suck a cock for me someday, sweetie?”

“Uhhhhh… ummmm… what?”

“I’m sorry.  Did you wanna cum tonight, sweetie?”


“So… are you gonna suck a cock for me someday?”

“You really want me to do that?”

“Yes, I do.”

“If that’s what you want…”

“It is what I want. So are you gonna do it for me someday?”


“Mmmmm… that’s a good PussyBoy.”

“I want to be a good PussyBoy for you.”

“I know you do, sweetie.  And I’m so proud of you.  Are you gonna suck a nice big black cock for me someday, and let him cum in your mouth?”

Hesitation.  Then “yes ma'am, if that’s what you want me to do.”

“Even if he cums a lot?”

“I’ll try, if that’s what you want me to do.”

“It is what I want you to do, sweetie.  I want you to feel what it’s like to suck cock.  To taste it.  To feel the heat of the meat in your mouth.  Are you going to swallow all the cum, like a good PussyBoy, or are you going to let it drip on the carpet?”

“I’ll swallow it all.”

“Do you know what will happen if you let any of it drip on the carpet?”

Hesitation.  “Yes.  I won’t let it drip.  I promise.”

“That’s a good boy.  Will you thank him afterwards, for letting you suck his big cock.”


“Will you tell him how good it tasted, and how much you liked it?”


“Are you going to suck black dick for me, whenever I want you to?”

“Yes ma'am.”

“Will you suck Johnny’s cock for me?”


“Will you suck it and get it hard so he can fuck me with it?”


“The next time I’m out of town, and Johnny wants a blowjob, are you going to suck it for him?”

“You don’t really want me to do that, do you?”

“Of course I do.  I want him to turn you into a little cocksucker.  I think you’d be good at it.”

“Oh God… can I please cum?”

“I don’t know, that depends.  Are you going to suck Johnny’s cock and let him treat you like a bitch?”

“Yes.  If that’s what you want me to do. Can I just please cum?  Please?  I’ll do anything for you.”

“I know you will, sweetie.  I know you will.  You’re such a good little PussyBoy, aren’t you.”

“I try to be, for you.”

“Is it OK if I tell Johnny how much you like getting fucked in the ass?”

(via polarities)

Sissyhusbandfantasies every little gurl needs @femdomsissy


Every little gurl needs to be taught

Cuckoldhusbandobediencetraining @femdomsissy



Thank You Mistress

Exactly the sort of thing that any pussyboy just loves to hear their mistress say.

Showyourtinydick dick so small you need to wear @femdomsissy


Dick so small you need to wear panties?

Swrredhead seriously you want to watch the @femdomsissy


Seriously? You want to watch the game?  Seriously?  Look at me, look at me.  Yeah, your game, but I have needs and now I want them taken care of. You can do this the easy way or the hard way.

Sissyarchive sissy archive all the best sissy @femdomsissy


Sissy Archive - All the best Sissy posts

Sissypantyboi4master thechainedwolf for all @femdomsissy




Seeing as how there are flags for BDSM rights, leather pride, rubber pride and puppy play amongst other things, I thought it would be a good idea to create a pride flag for sissies.

This was my idea, and working with my sissy pet GirlyNekoBoi (please follow him and his photo accounts) we eventually ended with this design. The appearance is partly based on the BDSM rights flag, which itself was based on the leather pride flag. The colours are the ones most associated with sissyfication and feminisation. The traditional male symbol is there to remind people what gender most sissies are (although my GNB is transgender).

Whether you are dominant or submissive, this flag is for anyone who considers themselves to be a sissy, or simply wants to support sissies.

Oh, that’s cute.

Sissypantyboi4master auntiesuzette @femdomsissy



Sissyhood, never to be taken lightly, yet to be enjoyed thoroughly…. choose wisely!

I choose!  ;)

Lyndseygurl substitute for wife @femdomsissy


Substitute for wife

Michelle4446 eraobsequium tangodeltawilli @femdomsissy




Hi. Sorry I haven’t introduced myself sooner. I know you moved in about two weeks ago.

I just wanted to let you know I can hear your husband’s screams all the way over at my house when you are punishing him – at least I guess that is what you are doing.


Well, I have a gag in my purse. I thought maybe we wouldn’t want the rest of the neighborhood to figure this out.

And I was hoping you would let me help.


Thank you so much for the gag!  And let’s see if you can help out, too!

Swrredhead come here sissy boy show me how @femdomsissy


Come here sissy boy.  Show me how good my little sissy loves to suck cock.  Oh such a good sissy you are, you suck cock even better when you have nice big hard Princess cock in your ass.  Good sissy you are.

request for some sissy strapon stuff

Herdickisbigger i am honestly scared of her @femdomsissy


I am honestly scared of her cock EVERY time it first goes in! Once I’m loosened up, OMFG I become such a slutty bitch boi for it! Even after she’s wore out from a good fucking, and I’m sore, I STILL want more!

Swrredhead come on slut take it all take my @femdomsissy


Come on slut, take it all, take my cock balls deep and beg for it deeper.  Naughty boy loves getting pegged

Yeahwatsup promiscuousgurlyboi @femdomsissy




Working gurls

all of the above is good with me!  hottt!


Swrredhead you want more i know you do i can @femdomsissy


You want more, I know you do, I can tell you love this big cock.  Tell Mistress how much you love her big dick in your ass. 

Sissycuckcumdump bitch daddy i like her way @femdomsissy



I like her way of thinking.

I’m your sissy bitch for life

Sissykiss from designer to dance girl you @femdomsissy


From Designer to Dance Girl 💕

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