[ / / / / / / / / / / / / / ] [ dir / animu / asmr / cafechan / htg / kc / leftpol / roze / vg ]

/sissy/ - Sissy

Bras, Boyshorts, Skirts, and Stockings ❤


Winner of the 36th Attention-Hungry Games
/alcoholism/ - The Attention-Hungry Games are the Dark Souls of Hunger Game Simulators
Comment *
Password (Randomized for file and post deletion; you may also set your own.)
* = required field[▶ Show post options & limits]
Confused? See the FAQ.

Allowed file types:jpg, jpeg, gif, png, webm, mp4
Max filesize is 16 MB.
Max image dimensions are 15000 x 15000.
You may upload 5 per post.

File: a035e3474be3d22⋯.png (1.4 MB, 1280x960, 4:3, 4f456de82534e276dd3f4300df….png)


Welcome to /sissy/. This board is for photos, stories, requests, challenges, hookups, or other discussions regarding male feminization, humiliation or sissification. Trans girls are also welcome!

What is a sissy? A sissy is a biological male who craves a submissive, emasculated status as a sexual fetish. This fetish includes crossdressing, anal play, and general feminization. Many play alone, and are "in-the-closet". Most desire to be used and humiliated by dominant men, either online or in real-life situations.

Visit our friends at:





58 posts and 1 image reply omitted. Click reply to view.






File: 1411279070012.gif (1.03 MB, 480x270, 16:9, 01 - 2PuITKq.gif)


Dumping a few captions.
76 posts and 92 image replies omitted. Click reply to view.


File: b73d4402ccde7b9⋯.gif (106.07 KB, 713x540, 713:540, Lisa Piaget Sissy ID Card.GIF)

File: e1084a148da48d0⋯.jpg (29.45 KB, 461x464, 461:464, sissy Lisa Piaget.jpg)

File: db2033aee82be0a⋯.jpg (336.11 KB, 1280x1707, 1280:1707, lisa piaget sissy.jpg)

expose and reblog this sissy cocksucking faggot everywhere


I'm a super sissy loser who needs to be exposed . my teamviewer will be open so come in and lock it down and make me watch you ruin me ! Ill be waiting !

Team viewer

Is 610 325 488

Pass : fy6p38





ejaculate in your face

or if you just want the same consistency maybe do some kind of warm water+cornstarch mixture and get something to squirt it like a baster




File: 43ac9281cab0678⋯.jpg (169.29 KB, 1280x1862, 640:931, d3f24bfd-0285-43e7-a17c-f0….jpg)

File: c0f2bc70d9907c5⋯.jpg (328.8 KB, 1280x1660, 64:83, bdf45f2a-2e84-47c0-9591-34….jpg)


Heyy, I'm a new-ish sissy who's just starting out, and I'm looking to exchange pics of myself and sexts if someone would help me get starting being a true little sissy boi by buying me a chastity cage (and maybe some other stuff💕). I'll model whatever you buy me just for you! Someone just please lock me up, I'm so horny all the time and I have a deep desire to be owned! Email: tumblrgurlc69@gmail.com

File: 1422758801874.jpg (63.59 KB, 640x480, 4:3, http://40.media.tumblr.com….jpg)


I'm not reeeaaally an ex-sissy. I just have my male side dominate my life now. But I used to be a 24/7 passable slut for a man I met on adultfriendfinder.

I was just going through some tough times with my exgirlfriend who unwittingly cuckolded me. We were just innocent kids. Back then crossdressing was really just a sexy thing I did that we both accepted.

We both had parents who were gone most of the day, leaving us to raise ourselves. We became hyper sexual. Searched both my girlfriends and my own house for porn. Found our parents sex toys. Fucked each other with them. She was bi, loved looking at girls. Both of us were molested sex addicts.

After she cheated on me I went down the rabbit hole and got a dick in all my holes well pretty much on a daily basis.

I put on some dresses and did make up. Took pictures and started a profile at the website. I was contacted by a man with a girlfriend that liked to make amateur porn and loved white boys that dress up. He wanted to make me his girl and maybe film me in scenes.
23 posts and 9 image replies omitted. Click reply to view.


File: 1441535852343.jpg (60.63 KB, 600x600, 1:1, 9755547885.jpg)


File: 1441535950740.jpg (491.61 KB, 800x1021, 800:1021, tumblr_ncke3fo7Jk1te4icko1….jpg)



I don't care if this is fiction. Fucking mind blown.



on average blacks have deeper voices and more often have athletic, muscular bodies

they're also more aggressive, which racists love to point out, and aggression translates into being more dominant in a relationship and during sex

they also are more open sexually, and more accepting of your sissy status

asians, on average, are in fact smaller stature than people from other races

they also tend to be smarter and have better income than blacks

intelligence and small stature aren't really traits that get a sissy off

white bois tend to be prejudiced and demeaning, good for psychological domination

they are also more passive aggressive which is annoying

note that these are generalizations, you'll always find exceptions to these rules in every race, but if you're looking for daddy with a certain characteristic you might filter by race first. that characteristic might be skin color anyway, then race would definitely matter

note note: these generalizations of races might actually not apply at all to dominant daddies looking for a submissive sissy, since those dominant daddies will already tend to be dominant in every way


File: 94bc512ea8472ec⋯.jpg (22.73 KB, 336x529, 336:529, cb44a370d1b54aaa0743c5409a….jpg)

File: 1411622865737.gif (971.63 KB, 460x393, 460:393, 1409626363052.gif)


So, to get right to the point; Is it possible to train your prostate into becoming an actual g-spot? Essentially make it more sensitive? If so, how?


It doesn't take long in chastity before you'll cum from anal. If you can't cum from playing with your clit, you better learn to cum from getting fucked.


You can be trained to have an orgasm even just by playing with your nippples. The orgasm happens in the brain. If you stimulate your prostate as you are cumming and watching sexual things then you'll soon be able to cum from it



I can't get my ovaries inside the cage though, they're so close to my body. What do?


Hey Guys, Sissy Rianne here. I'm a closet sissy and I'd like to get a submissive task over email every now and then. I'd confirm I do the tasks by taking pictures. Send me an email and we can sort out boundaries and interests: sissyrianne@outlook.com


Is there any way to make your penis smaller without causing erectile disfunction?



I'm pretty sure temporary chastity in a small enough cage can cause permanent shrinkage. I'm naturally tiny so I've never worried too much about that personally




I was going to write a big ass post but tl;dw is that unless you're actually physically crushing and damaging the clitty and waiting for the clit to reheal in-place, your fully erect clit size won't change. And according to this guy there is no permanent damage: https://malechastityjournal.com/2016/05/26/permanent-changes/

Further, erectile dysfunction is not permanent, assuming you're not old or have some kind of muscle/nerve/hormone disorder. If you're healthy, it's either psychological, or a loss of muscle memory/control. You can actually train yourself to have ED; I've actually done it myself and then re-trained my way back to full functionality.

Knowing these things, your best bet is to aim for minimizing your flaccid size (which involves muscle control and blood flow/pressure, specifically about relaxing whatever muscle that helps push blood into the penis). Chastity cages probably help train you in this but you definitely don't need it. Prostate stimulation coupled with waiting for yourself to go flaccid after going erect, and ruined+flaccid orgasms are how I trained myself. Eventually you'll learn how to prevent blood from filling your clit.

You might be able to do some shit involving contraction of the blood vessels, like how when you genitals are exposed to extreme cold they shrink and retract into your body, or maybe some kind of drug that constricts blood vessels, but those probably aren't useful for sexual purposes.

File: 977fae7bdb59d86⋯.jpg (427.31 KB, 1266x982, 633:491, message.jpg)


Waiting to reply to you


I'm a super sissy loser who needs to be exposed . my teamviewer will be open so come in and lock it down and make me watch you ruin me ! First come first to torture me!

Team viewer

Is 610 325 488

Pass : fy6p38


I'm a super sissy loser who needs to be exposed . my teamviewer will be open so come in and lock it down and make me watch you ruin me ! Ill be waiting !


I'm a super sissy so come on teamviewer and expose me asap. Lock it up and make me watch helplessly as you go through and do whatever you want!


Id: 610 325 488

Pass fy6p38

File: 50b594c33ba7db0⋯.jpg (611.08 KB, 1280x765, 256:153, tumblr_ordk52Gmgw1rw2ehco1….jpg)


Overwatch faproulette

14 posts omitted. Click reply to view.











File: c1d4cab23ce0c19⋯.jpeg (278.24 KB, 678x1205, 678:1205, Snapchat-2123926007-01.jpeg)


her IG: Sissytrapnina


File: 7cc5098e11e56f1⋯.jpg (211.53 KB, 720x1034, 360:517, IMG_20180318_121717.jpg)

okay i admit it, this is me haha, follow me guys <3




You look good but this looks photoshopped

File: 24e1c98fe3fa12f⋯.jpg (41.27 KB, 480x480, 1:1, 14.01(1).jpg)

File: 76722918b2b2c9d⋯.jpg (154.64 KB, 2048x1536, 4:3, 2017-10-21-095845.jpg)

File: 1febb456e324308⋯.jpg (36.92 KB, 480x480, 1:1, FB_IMG_1490027060903.jpg)

File: f98e89c2037ace6⋯.jpg (55.06 KB, 720x861, 240:287, FB_IMG_1490027070067.jpg)

File: 846b75e8695e359⋯.jpg (37.96 KB, 480x480, 1:1, FB_IMG_1490027078784.jpg)


german sissy

1 post omitted. Click reply to view.


File: 0b8e3df126c7875⋯.mp4 (11.08 MB, 1280x720, 16:9, 76bad4545b1e4b6d9d1622be1e….mp4)

Passwort and Photos


File: 80d2ee0ee36f461⋯.jpg (114.9 KB, 2048x1152, 16:9, 27624873_158934191419379_3….jpg)

File: 80d2ee0ee36f461⋯.jpg (114.9 KB, 2048x1152, 16:9, 27624873_158934191419379_3….jpg)

File: 8c653339073215c⋯.png (81 KB, 720x1280, 9:16, Screenshot_20171216-232222.png)

google login


key: ilovesissy


File: 695fed437cf9a03⋯.jpg (829.12 KB, 2046x2046, 1:1, IMG_20171119_162609_311.jpg)


File: 695fed437cf9a03⋯.jpg (829.12 KB, 2046x2046, 1:1, IMG_20171119_162609_311.jpg)

File: 71e871383a93e5e⋯.jpg (279.04 KB, 1872x3328, 9:16, IMG_20180210_093322.jpg)



File: a89b650e0384889⋯.png (1.38 MB, 1920x2646, 320:441, screencapture-facebook-ale….png)

File: a89b650e0384889⋯.png (1.38 MB, 1920x2646, 320:441, screencapture-facebook-ale….png)

any teamviewer

665 787 194


File: b32594d591880fa⋯.jpg (372.49 KB, 540x960, 9:16, 8c1d7189-8135-43b0-b397-42….jpg)

File: d31f1f5f328f36e⋯.jpg (226.59 KB, 960x540, 16:9, f1f45148-2b56-45f8-8e4c-ce….jpg)

File: 941c6f83a0089bb⋯.jpg (350.66 KB, 960x540, 16:9, 1527b765-2c94-4c68-8016-1d….jpg)

File: 43d07c433c2aebd⋯.jpg (373.93 KB, 960x540, 16:9, f1ccd94c-18e0-4c12-bb91-8d….jpg)


This slut posted wanting their pictures passed out where they would be degraded and humiliated. Post your thoughts here or KIK them at MP567890 to show this little sissy what a real man looks like and what a pantyboy is used for.


File: a10bf5e2fbfb608⋯.jpg (453.22 KB, 960x540, 16:9, 56550566-c1d0-4663-bd57-e3….jpg)

File: d6818e2af0d4fac⋯.jpg (407.51 KB, 540x960, 9:16, 6f50432c-170c-4b5f-9202-e8….jpg)

Sent me a couple more… look at that tiny sissy clit!





Damn that's a cute little one… This Sissy is in serious need of shaving though.

Delete Post [ ]
Previous [1] [2] [3] [4] [5] [6] [7] [8] [9] [10] [11]
| Catalog | Nerve Center | Cancer
[ / / / / / / / / / / / / / ] [ dir / animu / asmr / cafechan / htg / kc / leftpol / roze / vg ]