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maidangela: Lol. Oh my goodness. Her little clitty is trying to swell in her chastity cage. What a true sissy. Just watching me kiss you Jerome has gotten her this excited. Lol. And we thought that you might get upset and act like a little bitch. Boy
ashli-richelle:master-ferdok: Because I want to know who finds this thought appealing. MASTER, i find this very appealing and would love to become an OWNED sissy slave to a very controlling and demanding OWNER. Ashli-Richelle. Flint, MI (810)516-7037
behindthecurtain15: Thought I’d switch gears from my sissy side and show followers the fun I have when I’m the one doing the fucking. My Fleshlight collection, plus easing into Suzie Carina Vortex and Angela White Entice. Videos in the archive of
sissyowner: cdcarly: ♥️ if you like it! 🔁 if you crave it! x cdCarly💄 Before I leave for a few days I thought I’d leave this here for you all. Which sissy craves this?
littlemisschastity: Had a request for a shot of Little Miss Chastity going reverse cowgirl on Lady Sapphire’s strap-on. Also had a request for a pic of the sissy’s hole, fresh from a fucking. I thought the two looked good in GIF form, hope you like!
dirtylittletrannywhore: i thought this trashy whore looked exactly like you, you filthy sissy slut- sure it’s not ;)
cockdrunk: How many times have you thought about dressing up and coming out as a sissy to your best friend?
sissytherapy: Turn your craving thoughts into a lustful reality, deep down you know what you were born to do sissy :3
People ask this a fair bit so thought I’d cover it alongside the sissy post to avoid confusion of terms:I’m not trans or on hormones. Dressing is essentially a fun thing I do. I while do seem have some little boobs going on, that’s just an odd
makeup-stained-pillowcase: It was close, but it looks like most of you thought the sissy deserved to be milked. Shame. I worked his pathetic little clitty mercilessly while I fucked his face with my dripping pussy. It didn’t take long until I felt
degradedsissy1: The frustration of the emasculated sissy… ….trying to sleep during the night in its stockings and pretty lingerie,… …aroused to distraction by the girlie sensations, feelings and thoughts as its sheer stocking sheathed legs brush
audreypink77: Doesn’t mommy’s hand feel better than your silly girlfriend’s?? Aren’t mommy’s breasts more ample than your girlfriend’s?? And does your girlfriend know that u are ur mommy’s closet sissy???? I thought not.
daddywantssissys: Such naughty thoughts and words from a good little sissy slut. Does not get much better than this.
jackiefucher: I wish I had a daddy doing this to me right now. His thick cock stroking in and out of my sissy cunt. His weight pounding down on me with every down thrust. His every thrust removing any possible thought, just desire and lust in my bimbo
tgirlsarehot: websissy: Yes Miss, Please. The thought of being your cum sucking sissy slave excites me tremendously. Please Miss, please make me your little fag. Please let me lick your balls, suck your cock and swallow your cum. Please make me your
zombee2468: tgirlsarehot:websissy: Yes Miss, Please. The thought of being your cum sucking sissy slave excites me tremendously. Please Miss, please make me your little fag. Please let me lick your balls, suck your cock and swallow your cum. Please make
ppsperv: Reblog if you thought about sucking cock today!Follow 🎀💄💋💕❤️Pretty Pink Sissy!❤️💕💋💄🎀!
fag4blkcock: I admit black cock made me a sissy faggot. This faggot white boi only beats off to black men or the thought of black men abusing me in front of my wife, family, and friends. I can’t cum in my wife as my tiny dick clit won’t get hard
slut-for-sissies: Be grateful for the glimpse @princess-jenna1 is giving you. Now edge until there’s not a single other thought in your head.
iamsissysamantha: ANY THOUGHTS, SISSIES?
sissyboiexposed:Good Morning Tumblr 💋 Lots of pics to cum later but thought I’d leave this here 💋💋💋 Sissy Vanessa 💋💋💋 I just love this girl
blackbeastandboibitches: White sissy bois may think that they are alone in desiring to dress girly, to get on their knees and blow the dicks of real men, but it’s a thought that every littly dicked puny skinny pretty white boi has once in a while.
scurvy-gurl: daddywantssissys: Such naughty thoughts and words from a good little sissy slut. Does not get much better than this. this is one of my all time favs, would only change it to YOUR* bitch :3
mandatory-feminization: A MESSAGE TO ALL SMALL COCK BOYS! Reasons why Boys with small cocks should be come Sissies: You will never be able to pleasure a woman sexually. Girls who you thought liked you will become disappointed and probably leave you, and
herhappysissywife: A Woman’s Prerogative“Just stay the way you are” She said.“But…i thought you wanted me in a dress?” the sissy cuckold asked.“I did, but he wants you in just lingerie and heels” the Wife replied.“I’m going to feel
chasteandimpure: I did warn you Sissy. I told you over and over to keep your eyes on my feet, but you just can’t help yourself can you! Sneaking glances at my stockings like the lustful little slut that you are. I thought putting you in that tighter
chastity-key-holder: analphafemale: beta-husband:I’m pretty small 4 inch….. What purpose does a penis serve on a beta male?I’ve shared some thoughts here on my blog.An Alpha Female Small cocks need to be locked and in panties! #chastity #sissy
dark-sissy-caps: The thought Keeps coming up more frequently 
peggingpuppet:You thought this was for you didn’t you sissy?
lockedupselena: delicatesissyboi: lockedupselena: Me :) thoughts ? Wanna be locked like this it’s the most comfortable feeling :) very pretty but i like my sissies to cum when i fuck them
drake6975: sassierica: sissiestaci: sissyboival: Oh god, I do!!! Omg I’m turning into a sissy n can’t help but love the thought Dress me up in pink, give me a pair of slippers, and find me my perfect prince Forget dress up…just give me cock
trapsandcumsluts: My blog explained in one post check it out The thought of cum makes me cum and then I lick up all my own cum. It’s a never ending sissy cumslut cycle!
dominantadmirer: sissypinkx: bigdaddyblog: pantyboybitch: part-timesissy: I would love to be a sissy housewife! The ideal job for me!!!!!!!! This is how you take care of a REAL man…and you want this more than anything… I love the thought
sissybitchbrides: This pretty boi used to love being “one of the girls” until the girl he had a crush on took that a little literally. He thought that she was always putting him the friendzone, but what she really wanted from her sissy boi bff was
sissydonna: sweet-sissy-natalie: I never had such thoughts *giggle* the first time I was dressed like a girl and had to suck a cock was like coming home… oh what a sweet memory *giggle* Where Boys Will Be Girls
abc12316: cockdrunk: How many times have you thought about dressing up and coming out as a sissy to your best friend? all the time
dionnespet: They rented the hotel room and thought they could get away with having some fun. In a few moments their wives will enter the room and turn their fun into a profitable new lifestyle. The soon to be sissy cock whores will see it as hell. Follow
exposedsissycockwhore: 100percentbritishfaggot: exposedsissycockwhore: On the eve of my Tumblr approaching 2500 Followers I thought I would make a post that my many Sissy Faggot beta Sluts could reblog and take this Pledge with me. I, Diane, as
cumcumsissy: itsmeganprincess:You never thought you would be softly kissing a man’s full balls, leaving little lipstick prints on his engorged sack…. Me aha xoxox I need to try this on some sissys
masterofsissies: Some sissies who thought I was joking when I said I was going to lock them up until next month - they wish they never made that stupid bet with me when they were drunk….
cockdrunk: You know they’ll find out soon. Follow me at cockdrunk.tumblr.com and @sissycaps Good sissies reblog CockDrunk ;) Do you worry about being found out…or does the thought excite you?
sissyandreaworld:sissy-pussy-galore:Well, we do like to play dress up.Exactly my thought before I even read the caption.
anythingforwordsworthy: Curiosity often never has a good outcome. How many times have you squirmed in your safe masturbation fantasies and wondered how these fantastic sissies look and act so good? Have you really ever thought about the process?
sissydonna: sissydonna: seattlejasmine: http://seattlejasmine.tumblr.com Clothes fit better than you thought they would? Time to rethink your wardrobe sissy. Where Boys Will Be Girls Where Boys Will Be Girls
sissydollychristie:So what was your first thoughts Sissy Dolls? ✨☺️💕🎀💋🏖🌈🌸✨
valsissyslut53: raquelmsweetcd: sissyofspades: I neeeeeed this!!! The thought of this scenario though! ♡♤ My sissy dream! Si una gang bang💋
sheplacementslut:Any thoughts to return to being a man quickly vanishes when daddy pulls your pink panties aside and fingers you sissy ass.
secretfemboy: Sissy Thanksgiving Pt. 5I was so embarrassed that I had gotten an erection when I took a sauna with Mr. Gregory that I had to get out of the hotel and clear my mind. What was happening to me? I had never thought about being with another
bi-bottom-bitch-stories: Sissy Sam, Part 1 Later that day, I got home, filled with a mixture of shame, pleasure and arousal. I logged back onto Tumblr, it had been a couple days. I had just found the “SissyRulez” blog, I thought it was the best!
edenalchemy: What are your thoughts on Sissy Dating?
jaynelovesdick: Call that Sissy Spot your G Spot It might have been a P Spot when you thought you were a guy But now that you are a girl you know it is far more orgasmic than anything you ever felt pretending to be a guy
ppsperv: Follow my tumblr—> Pretty Pink Sissy Perv jdubjsw: blackmywife: theirhappening:Love it! reblog if you like the thought! In a heartbeat!
lynne-en-femme: I got a new toy too. Yay! :) I’ve always wanted to feel a man’s hot cum inside my sissy pussy, but I’ve never been willing to fuck bareback, so I thought I’d give one of these a go. Video tomorrow …
