I might be a sissy Yea Forums, help me decide what to do, tell me your sissy stories or stories about fucking sissies

I dont see why not. Shame is half the fun

If you could be a hot sissy, then I wanna see how hot you could be.

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Have you done it before, my issue is I'd have to lose muscle. Also hot pic.

Well it all really depends on the shame were talking about. shame in the bedroom? definitely sexy and part of the kink. Shame for having the kink and outside of the kink? not so sexy

Not a sissy myself, but I am a married man who's both a master/top and a power-bottom. My wife pegs me when I tell her to and I fucking love it. I don't find men sexually attractive at all either, but damn if getting fucked up the ass doesn't feel good, doubly so when you can collapse onto a warm pair of perky tits afterwards.

Fuck man how did you bring it up to her.

Open communication is a huge thing with us. Honestly, I know I lucked out and landed an epic catch of a wife, but it's all about communication. Keeping it all non-judgemental too. Talk about things you look for in porn. Take yourself entirely out of the equation and try to learn what intrigues her (intrigue is different than like. You can be intrigued and not want to participate, but the initial idea still fascinates you in some way). Simple shit will come out at first but, as you start going out on a ledge and talking about some thing that even you aren't entirely comfortable with, the will start sharing some too.

honestly, pegging took me a LOT of working up to. Being able to be vulnerable with your woman is something a lot of guys can't bring themselves to do. You can admit you're interested in something, even on a trial basis, and also admit that you're not comfortable about it. This makes its a much less aggressive conversation and puts her on equal footing.

That being said, I will say that I consider myself bi, and always have, but I have a severe distrust of men. I don't keep many male friends either. Discussing that with her helped as well. I'm happy with who I'm with and I love our relationship, but there's a side of me I wanted to explore more and I asked for her help.

Do you dress up to like role reversal or just naked pegging

Whoo think was him!?!

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you ever suck a dick?

Not yet

Make a list of steps to take you where you want to be, as a sissy. Show us.

Show your body, we will see if its femine enough.

Depends. Some days it's just naked pegging or being toyed, but that tends to be with me much more in control. Giving orders and feedback and having her serve as my sub. We already have an established dom/sub relationship so that was a benefit as well.

Honestly, I don't like sissy shit. I'm not into makeup or degredation, and I don't have chick clothes to put on. But, I will say this, when I can get her into a top-male headspace (she's very female but considers herself pan), the pegging is mind blowingly worlds better. It's not a mechanical attempt to follow orders, it's a joyful fucking. For that, I'm usually happy to play into a few requests of hers like letting her mouth off (I don't tend to be very verbal when getting pegged. Too busy moaning and screaming). The furthest I'd say I've gone is wearing a skirt because, and I bet everyone of you fuckers can relate to this, from the "I have a dick and am fucking someone from behind" perspective, there's something cathartic about fucking a girl with her skirt on. Just lifting it and having it splayed out over your legs and stomach as you hold onto their waist and fuck. I'm getting something new and joyful out of it, and so it she.

im not a sissy but im into sucking dick so i might be kinda biased. you want to suck mine?

Nah I see how pics circulate on here

What do you mean?

You want a sissy story?

>Be me
>Be 22
>Hit up Grindr for someone to fuck
>Match with an older guy who's in town for three months on business
>Get drinks at local bar
>Tells me he wants to fuck me
>Go back to his very decent served apartment and he fucks me
>Shit's good
>He keeps referring to me as a 'good girl', a 'cock whore' and a 'slut' and referring to my asshole as a cunt, pussy and boypussy
>Tells me he wants to fuck me every day while he's here
>Says he'll shower me with cum and gifts
whythefucknot.gif
>Keep meeting him every day or two to fuck
>He buys me nice dinners, takes me out, gets me some nice clothes, pays for the nice Uber to collect me and take me home
>Third time he asks me if I'm down for a little for a little role play and crossdressing
Sure why not
>He leads me into the bedroom and tells me to put on what's on the bed
>Pleated skirt, stockings, tank top, cock cage
>Fucks me like a girl with the clothes on
>Over the next few weeks he has me stay with him while he works from home
>Has me wear girl's clothes constantly
>Leggings, denim shorts, comfy skirts, tank tops, summer dresses, etc
>Makes me dress up to fuck, keeps me caged
>Starts buying me more expensive stuff
>Like, watches and shit, then just leaving money in my bag
>Treats me like a sissy bitch for three months
>I go there to meet him on the last night
>Spend an epic night of passionate male on sissy bitch love making
>Fuck long, fuck often
>Next morning he's gone with all his stuff, and there's a note telling me he had a good time and $10k cash
>Never see him again

...maybe... what's it like?

sucking dick? or sucking my dick specifically?

No fucking way also that's hot as fuck. How did you like it? What was the cage like? Have you been fucked before? Thanks for actually responding to my post correctly.

Sucking dick

How far have you taken it? Are you cross dressing? Show us.
Make a gay friend and start talking about it. Maybe see if he'll let u kiss him or touch his dick.
What's next for you?

I have a plug so far nothing else yet. And I guess I could try that. I wont post pics on here

Just don't post face. Posting yourself in lingerie will help you make the next step

I once took a kids hand and made him keep hitting himself with it, he freaked out and started crying like a little sissy.
Maybe I should take your hand and keep hitting you with it too?

Maybe after a few steps.

Going sissy takes a lot of dedication and hard work. Are you up for that?

Like what?

its hard work. its uncomfortable and the jizz tastes awful. but the fact that it is a struggle and that it feels so good for him is what makes it so fucking hot. if you're truly submissive you will do this and you will strive to get good at it with a slutty passion.

I'm gay, so yeah I have before.

Never got into sissy stuff before, but fapped to it and trap porn. This was the first time getting fucked while crossdressing.

Shit was good. This guy basically seemed like he was living out a fetish/fantasy and had the means to do it.

Wearing women's clothes for three months straight has given me an appreciation for how comfy it is. I don't wear out in public, but I wear leggings, tights, skirts, dresses, activewear and some other things privately. Skirts in summer is liberating as shit and I started wearing kilts and sarongs out and about.

As for the cage, it was weird at first. I think he wanted to hide my cock while he was pretending to fuck a woman. I wanted to be hard and fap but he didn't want me to, but as long as he was giving me free shit I didn't mind it too much. I didn't keep it.

Fuck, I just realised I replied to myself.

Damn that's hot as fuck. The cage to me is all about dominance and humiliation so I get it. Probably about not allowing you to be masculine or have control.

Are they more comfortable than girls clothes?

Guys*

Definitely. Men's clothing is usually made of harder, thicker, harsher material. At least, unless you invest more money on higher quality or more expensive materials. Compare men's jeans with women's jeans, or men's cotton track pants with women's. Men's track pants are usually thicker and heavier, but women's are lighter and thinner, making them more airy and comfortable.

Skirts and dresses are breezier in summer, hence now wearing kilts and sarongs to get the same feeling without actually wearing women's clothes in public.

Leggings, tights, etc, are comfy as fuck. Imagine a nice, tight second skin. A good women's tank top, especially activewear, achieves the same thing for the upper body. There's a reason that women basically live in them both at home and about now.

And, finally, women's underwear. He only had me wear pretty ordinary stuff, nothing frilly, and I found that a size 16 fit me perfectly while not crushing my balls, but women's comfy undies are also thinner and softer than men's equivalents.

What? Sucking dick is only as much of a struggle as you make it. It's Hella a fun and I'm sorry but cum tastes amazing. Also sucking dick makes you look and feel super cute. Shit now I'm turned on lol.

Tell me more

im just tryna set first time expectations, bob. if he's a cock slut for real then he will love every bit of it as you and i probably do

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Interesting, did you wear thongs too?

Nah. Only stuff he asked me to wear, and I continue to wear, are various types of boyshorts and bikinis. Also a fan of a particular brand that sells a cut called 'cheekster' because they're string sided, so very airy. I've tried thongs and g-strings, but I don't like picking 'em out of my crack

Once i went to a place to meet with a guy, i like fem shit, we had fun, let him to play with my ass with his cock. Pic is me.

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Hello Tom. I'm surprised you're back on Yea Forums after it got outed your wife fucks other people when you keep posting those chastity threads.

Few facts about Tom:
>Tom is a cuckhold
>Tom identifies with women sexually
>Tom wishes he could put his brain in a females body and has considered becoming a tranny

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Tom believes that if you fuck his wife and bail that he's the powerful one because he gets to cuddle her after you fuck her.

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SEX

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Jesus christ

This makes me feel irrationally angry.

End youself

What was it like?

That makes sense

wrong!

Well I'd still need to lose arm and shoulder muscles

Maybe.

>OP

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kill yourself, faggot, before the AIDS does

>implying he isn't posting this for a fap session based on a porn induced fetish that he has no intention of practicing irl.
Bro you just don't understand sissies.