Should I Be a Sissy?

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normalguy4449

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Im a 20 yo guy, I like girls and they turn me on but what turns me on more than anything is the thought of shaving, dressing up as a girl and being humiliated by a girl or giving a guy head/him fucking me. Do people think it'd actually make me happy pursuing this sissy thing as no girls would be interested in it and I'm not sure if i could actually get with a guy, being normal and straight makes for an easier life but it doesn't turn me on as much as this. What should i do? Thanks
 
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Im a 20 yo guy, I like girls and they turn me on but what turns me on more than anything is the thought of shaving, dressing up as a girl and being humiliated by a girl or giving a guy head/him fucking me. Do people think it'd actually make me happy pursuing this sissy thing as no girls would be interested in it and I'm not sure if i could actually get with a guy, being normal and straight makes for an easier life but it doesn't turn me on as much as this. What should i do? Thanks


Hi and welcome normalguy. You may wish to post an intro thread when you can, it will help other thread dwellers to get to know you.

In regards to your question you are allowed to be whatever you wish to be. From what you described it does seem to elude to being a classic sissy in the strictest sexual and fetish meaning. You want to be humiliated by being made up in female attire then forced to perform sexually. Whether this will make you happy comes down to your own experience, nobody here can see inside your head. You are obviously thinking about this fantasy and until you face the situation for real you will probably never know if it is something you want.

What I would recommend is that you try one element at a time. It may be that you want to try all the different aspects of your fantasy in little pieces then put them altogether when you have the experience you need. This role is not something that should be taken lightly. I know many sissies, some are successful and interesting, others are weird and gruesome. Throwing yourself head first into homosexual sex, with added cross-dressing and humiliation can be a lot to deal with on an emotional level. If you can find a mistress who enjoys sissies you may be able to be taught how to be a good sissy for pleasing men. There may even be a patient master or a fellow sissy that can guide you.

Possibly start with a little cross-dressing, get used to being and acting female. From your post I can assume that you will probably be looking towards the more stereotype, misogynistic view on what makes a woman. But you are not looking to transition in real life so your fantasy can be whatever it needs to be. When you feel comfortable acting in the role play you envisage you can move onto involving another person. One thing I would say is that men who enjoy sex with cross-dressers normally like those that are convincing as a girl. Those that have hairy legs and a five o'clock shadow will not be very appealing. So being able to entice potential play partners may depend on your make-up, dressing and mannerism skills.

Another aspect you have mentioned is the humiliation side of things. Have you researched this side of your fantasy? Humiliation comes in many forms, from physical to mental, emotional to practical. I assume because you are on this site you also have ABDL tendencies so try to work out if this is something you can work into the humiliation. Forced diaper wetting is a classic sissy baby experience and can lead to opening up the play session to other avenues.

If you do decide to move on to having sex with men try to get with someone that has experience having sex with cross-dressers. I only say this because unless you have experience with anal you may find the enjoyment is short lived and really disgusting. This is not the place to go into details but research good anal practice on sex education sites and possibly even BDSM or fetish sites. The last thing you would want is your fantasy ruined by poor preparation. Also make sure you agree to what you both want and start off slow, there is no need to have it all up front. If you do end up with someone who is just as inexperienced as you then make sure you have communicated and both fully understand what you are aiming for.

Best of luck, have a blast, experience life.
 

normalguy4449

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Wow what a reply haha thanks for taking so much time! Yeah I s'pose slowly incorporating things bit by bit is a good suggestion, no need to rush into anything and to start playing around in clothes on my own is harmless and sounds a lot of fun:) Shaving all over and make up I guess are the next level but as you said bit by bit and I guess I'll see how I feel! About the mistress thing, I assume you're talking about paid ones? You might know better but my assumption is that no girl would ever just humiliate/tease sissies off her own bat for fun? But thanks again for the reply, p.s. you look really good on your pic:)
 
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Thank you and you're most welcome. It is nice to be able to respond to something I actually know quite a lot about for once.
 

jamila

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"Should I be a sissy?"

No, you should not be a sissy normalguy

You should not be a sissy because you can only be a sissy if you already are a sissy and if you can honestly ask if you should be a sissy you are not a sissy and if you are not a sissy you should not want to be, and cannot be, what you are not.

Now I'm a sissy. I have been a sissy for fifty-eight years since the age of three. I absolutely love being a sissy in spite of the fact I would have been so much better off if I had not been born a sissy in 1955 because being a sissy back then was the greatest shame because all of us 'sissies' were assumed to be 'poofters' back in that ultra homophobic time even if, like me, the sissy in question was not a 'poofter'.

Regardless, there is something about being a sissy male that is so good it still dumbfounds me. Because I'm a (heterosexual) sissy I have only had two serious relationships in my entire life and both only lasted two years. Both of my girlfriends left me because I was "a lousy lover" my second girlfriend and only defacto said. My first girlfriend - my one true love - left me a few months after we had sex for the first time after two years of loving friendship and kissing & cuddling for hours on end. She was a virgin and I was a huge disappointment to her because what I really was to her was her girlfriend rather than her boyfriend, but she apparently didn't realise that. I really should have refused to have sex with her because I didn't want to, but I loved her so much and if I had turned her down?

"Should I be a sissy?"

“Alone”

By Edgar Allan Poe

From childhood’s hour I have not been

As others were—I have not seen

As others saw—I could not bring

My passions from a common spring—

From the same source I have not taken

My sorrow—I could not awaken

My heart to joy at the same tone—

And all I lov’d—I lov’d alone—

Then—in my childhood—in the dawn

Of a most stormy life—was drawn

From ev’ry depth of good and ill

The mystery which binds me still—

From the torrent, or the fountain—

From the red cliff of the mountain—

From the sun that ’round me roll’d

In its autumn tint of gold—

From the lightning in the sky

As it pass’d me flying by—

From the thunder, and the storm—

And the cloud that took the form

(When the rest of Heaven was blue)

Of a demon in my view—


Am I glad that I have been a sissy for fifty-eight years? Hell yes! But the price has been pretty high. So what is it that I got from being a sissy for all of my life that stopped me from committing suicide which I began wanting to do from the age of eleven and ever since? How have I managed to live through forty-eight years of living my life alone in the world as a sissy, mommy's boy, diaper loving, 'little', transvestite, humiliation loving masochist?

"Suffering is the door - the only door - to the depth of truth" (Paul Tillich)

Should you be a sissy?

Do you have the 'balls' to be a sissy normalguy?

"That is the question."

Because if you don't have what it takes to be a sissy you should be a man instead.

best wishes
 

rennecfox

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"Should I be a sissy?"

No, you should not be a sissy normalguy

You should not be a sissy because you can only be a sissy if you already are a sissy and if you can honestly ask if you should be a sissy you are not a sissy and if you are not a sissy you should not want to be, and cannot be, what you are not.

Exactly its not like picking whether to get a couch or twin recliners,
 

jamila

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LOL :smile:

I might also add that I consider myself to be a ‘sissy’ rather than a TS because I have always claimed that I want to be a girl and not I’m a girl in a boy’s body. Now wanting and being are not the same thing of course. You can only want to be something if you aren’t what you want to be whereas a TS would claim “I am a…” not “I want”. However, I take it as a given that someone can be a sissy and also be quite happy and content being a boy. I would call that being a ‘sissy boy’ - whereas a sissy (boy) who wants to be a girl (like I do) I would call a straight ‘sissy’.

So we have sissies, sissy boys, and m2f transexuals who, of course, could be straight out transexuals or sissy transexuals, but not 'sissy boy' transsexuals. So, have I resolved the bitter debate out defining sissies vs transexuals? No? oh well... don't blame me I'm just a silly sissy.
 
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HoganBunny

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"Should I be a sissy?"

No, you should not be a sissy normalguy

You should not be a sissy because you can only be a sissy if you already are a sissy and if you can honestly ask if you should be a sissy you are not a sissy and if you are not a sissy you should not want to be, and cannot be, what you are not.

I find that is a rather limiting definition. Labels really are what you make of them. They're a shorthand way of explaining complicated interests, and as such, they don't capture the nuances. Two people who identify with the same label may well have differing interests within the broad area described by that label.

Questioning whether a label applies is, well, rather common, and it doesn't say anything about whether the label fits that person or not. Once you realize that you don't exactly fit into the typical mold, it's not unusual to switch labels or question which labels best fit you. Labels really are just an imperfect shorthand for describing a broad, colorful spectrum.
 

jamila

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You are quite right about definitions imho HogansHeroes, but the statement that you quoted is not a definition of 'sissy' it is an indisputable existential fact that you can't be what you are not. Yes, you can become what you are not on rare occasions, but notice that the OP said 'should I be a sissy' (which is existentially impossible and which was why I highlighted it) Now if the OP had asked "Should I become" I would have said something else entirely, but that wouldn't have been a definition of 'sissy' either because we are not trying to define what a sissy is or might be (and I wouldn't even attempt to do that) we are talking about becoming a sissy at 21 years of age. I would also point out that my last post just before yours does not attempt to define what a 'sissy' is or might be either, but is, rather, a discussion about two 'types' of sissies.

regards jamila
 

CanadianGal

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Don't ask others what you should do. Do what makes you happy. As long as you are not causing harm to yourself or others, you don't need permission to be.
 

TenaHyena

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I've had a similar conflict. I Enjoy the thought of wearing pink, frilly clothes... but when it comes to trying them on, just feel a little silly. Anyone had similar reactions to the first time experimenting? Or was everyone in love with dressing up from the start?
 
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