Crossdressing/sissification???

Sex Tips & Talk
1

Hi.

I started fantasizing about dressing, acting and being treated as a woman, by a woman and for a woman only. Not that I'm some narrow-minded, obnoxious homophobic bigot, I'm just not interested in crossdressing or sissyfication (you name it) in and on itself, or either as an outlet for gay fantasies: I don't get aroused at the thought of any man.

It's just something I'm curious about doing for a woman.

The point is: am I on the verge of making something stupid? And I'm not implying that people who have a thing for transgender (sorry if I mess up with the jargon) are stupid. Actually, their case is the other way round: they are so sure about what they like, that they just don't have these kind of dilemma.

Truth be told, I never was into gender roles. And probably, I'd fail dramatically at the mere attempt to take it to real life. It has never been my kink. I don't dismiss anything. But, so far, it has little or nothing to do with me, with my core erotic landscape, so to say.

I'm having a hard time meeting knew people. I had a couple of awful experiences which led me to the conclusion that I've never been truly in love. It's sad and it hurts. I decided to stop worrying about it and have some fun. But online dating and one night stands left me drained and empty. I'm bored of all that. It makes no sense anymore. Specially when you've been dating people you don't like at all on purpose, selling yourself short and settling down for what the undertow may bring. Sex, thus, became mechanical and shallow and no longer enjoyable.

Why dating people you don't find attractive? Because they are easier to deal with if things go wrong. They are easy to break up with. There's also no risk of falling in love with them. I know I might sound cruel, but that's not my intention. All of this speaks of my own emotional block. I feel numb, I'm blind to the girls and women I like indeed. I'm afraid (since always, but later it became more intense) of going after the girls and women I find attractive, because I know that that's when there's something more at stake. I'm not talking about fear of rejection. I'm talking, instead, about fear of being accepted!

It's like... "Ok, she didn't say 'No', she said 'Yes': what should I do now???" In other words, I'm afraid of finally getting what I want, because that will lead to not wanting anything anymore. Like if achieving your desire will, in that very same act, annihilate your desire.

Anyway, I'm derailing. Let's get back to the topic's subject. I find crossdressing/sissification/whatever is the ultimate way of giving yourself to someone, which I'm clearly uncapable of right now. After everything I've just told you, it's obvious that I'm blocked and I can't let my feelings flow. I grew cold and distant. And that's why I'm unable to connect and enjoy sex.

It seems I lost touch with my feminine side. Instead, I became so focused on being a sex machine and a merely rational being (proof of the later is this very same post, obviously). Needless to say what one's feminine side consists of.

Maybe, and I'm just guessing, crossdressing/etc fantasies are just the most virulent way of venting that natural part of my self that I've been repressing for so long. Instead of being a little more caring, emotional, nurturing, sensitive, open, sentimental, warm and vulnerable each day, it bursted in all of a sudden in the shape of an hyperbolic femininity, after so many years of keeping it burried deep inside of me.

Funny thing is, I fantasize of acting like the kind of girl I wish I met.

Well, that's it. I'm not scared of either being or turning gay whatsoever. Again, not that it would be a bad thing. It's just not what I'm actually going through. My fears, as you can see, are of a different nature. And I'd probably would be suffering them as well even if I actually were gay.

Hope it was not that confussing. Thank you for reading.

1 Like
2

To be frank, I'm not certain what bit of it is worrying/bothering you (but that might well be my fault as I'm not fantastic at handling large volumes of text!) - but as someone on the fetish scene myself, I come across a variety of people who play with gender in varying ways.

Yes, some people are transgender and seek to present as a different gender in a long term way (that is to say they one they identify as rather than what they were assigned at birth). There are also people, often referred to as TV/CD - transvestite/crossdresser. Those people may dress in opposite-gendered clothing publicly, or only in private. They are of various sexualities, and in their day to day life they may be uber-butch, camp, or a million and one different things.

So, I guess in short what I'm saying is - have fun with it, and don't think it means a thing about who you are more generally. :)

3

NymphetamineKiss wrote:

To be frank, I'm not certain what bit of it is worrying/bothering you (but that might well be my fault as I'm not fantastic at handling large volumes of text!) - but as someone on the fetish scene myself, I come across a variety of people who play with gender in varying ways.

Yes, some people are transgender and seek to present as a different gender in a long term way (that is to say they one they identify as rather than what they were assigned at birth). There are also people, often referred to as TV/CD - transvestite/crossdresser. Those people may dress in opposite-gendered clothing publicly, or only in private. They are of various sexualities, and in their day to day life they may be uber-butch, camp, or a million and one different things.

So, I guess in short what I'm saying is - have fun with it, and don't think it means a thing about who you are more generally. :)

Thank you and sorry, you're right: I myself lost the point.

Question, in a nutshell, is: am I'm wasting time (and energy, and eventually missing my goal) trying to work something out by transgenderism, when the more accurate way of solving it is more "simple"? (I'm putting my emotional block as a problem, and crossdressing as probably the most complicated solution to it).

4

I suppose, to my mind, what it comes down to is the role crossdressing plays for you. It might turn out that it is actually a need for you - which I don't believe to be a bad thing, we're all wired in varying ways - or it might be, as you suspect more of a sticking plaster solution to your problems.

I think the easiest way to move forward is probably in trying it out a bit and seeing how you feel. Purely on the CD side, if you don't have one, I'd suggest a Fetlife account as there are lots of groups on there that may be of help. In terms of the deeper psychological issues, it's probably a bit beyond what anyone can work out online. Have you ever spoken to anyone about the difficulties you have with intimacy?

5

I cannot comment on your way of attempting to deal with deep seated emotional issues by crossdressing.

Personally I love to cross dress for my OH, in private and purely for sexual relief. I enjoy the dressing up, usually stockings, lace panties/briefs, short skirt with petticoats and a short chemise or similar. It brings out my submissive side and really allows me to play.

There is no hint of being homosexual as I don't find men that attractive but ultimately I do enjoy my OH to peg me while dressed up. She loves it as well, its a way for me to get a degree of satisfaction and release I never really managed before.

So don't over analysis, have a go in the privacy of your own home and see how it makes you feel, it does help if your partner is understanding.

1 Like
6

NymphetamineKiss wrote:

I suppose, to my mind, what it comes down to is the role crossdressing plays for you. It might turn out that it is actually a need for you - which I don't believe to be a bad thing, we're all wired in varying ways - or it might be, as you suspect more of a sticking plaster solution to your problems.

I think the easiest way to move forward is probably in trying it out a bit and seeing how you feel. Purely on the CD side, if you don't have one, I'd suggest a Fetlife account as there are lots of groups on there that may be of help. In terms of the deeper psychological issues, it's probably a bit beyond what anyone can work out online. Have you ever spoken to anyone about the difficulties you have with intimacy?

Thank you once again.

I buy the second possibility. The sticking plaster. If it were a need, I'd rather be getting busy buying woman's clothes and asking for advice on how to wear them. Which is not the case.

Trying it out would help. But here's the paradox: I'm not interested in doing it for myself. I want to do it for my eventual significant other, as a way of allowing myself to trust and giving myself to them. Yet, in order to find a significant other, I must open up and get over this emotional block I wrote about. And, in order to open up, I need to get in touch with my feminine side again... by crossdressing in front of that significant other I'm longing to meet? That's where either I get stuck or find that crossdressing is a little too much, an out-of-proportion solution.

I'd probably give Fetlife a try, unless the whole CD thing turns out to be a waste of time. Maybe it's just a way of distracting myself from taking matters on a more realistic way.

And yes, I sort of discussed this (my emotional block, not my CD fantasies) with a few friends lately. My closest circle of friends, I mean. Both male and female. It wasn't easy, but I shared this with them. And their opinions are all the same: I should stop over-thinking, specially when it comes to feelings, emotions and pleasure.

Maybe, my sudden CD fantasies are anything else but a new problem to keep my mind ruminating.

7

bigstu wrote:

I cannot comment on your way of attempting to deal with deep seated emotional issues by crossdressing.

Personally I love to cross dress for my OH, in private and purely for sexual relief. I enjoy the dressing up, usually stockings, lace panties/briefs, short skirt with petticoats and a short chemise or similar. It brings out my submissive side and really allows me to play.

There is no hint of being homosexual as I don't find men that attractive but ultimately I do enjoy my OH to peg me while dressed up. She loves it as well, its a way for me to get a degree of satisfaction and release I never really managed before.

So don't over analysis, have a go in the privacy of your own home and see how it makes you feel, it does help if your partner is understanding.

Thank you for your response.

I'm well aware that discussing CD fetish would be more interesting if I already were in a relationship, and there were a real scenario in which I struggled with, let's say, whether share this kink or not with my partner, and, if so, then how approach it, etcetera.

Being single and trying to fix something else makes the CD subject, at least in my case, almost pointless. And I know that, and I won't be surprised if someone finds it that way.

Again, the question is if all I'm actually doing is wasting time into a brand-new problem created by me myself, in order to keep me from taking matters in my own hands, right here right now.

I mean, what's the true reason behind I started to fantasize about crossdressing? Is it just for fun? (And seriously doubt it, because I feel unease and anxious about it, although not because it could mean a closeted homosexuality) Or is it just, like I said before, the most difficult solution for a much simplier problem?

8

you will never knwo the true reason until you start to explore it. furthermore, the true reason, or what you think is the true reason, may keep on changing as you change and become more involved or distracted away from dressing.

It is something I have toyed with myself for years and years and still have not got to the true reason.

At the moment however it is something that simply turns me on and makes me feel good sometimes.

Like you, i did think it would help me get closer to a partner as for me, dressing is also part of my submissive side. A million questions have run through my head over the years and I still havent found the answer.

Just know this - as you explore this road, there will be great times and not so great times - as with anything - so just go with it if you feel it is the way ou want to go and slow down when you feel you dont want to explore it for a while.

9

wonderlost wrote:

a brand-new problem created by me myself, in order to keep me from taking matters in my own hands, right here right now.

That was my guess after reading this:

I'm not interested in doing it for myself. I want to do it for my eventual significant other, as a way of allowing myself to trust and giving myself to them. Yet, in order to find a significant other, I must open up and get over this emotional block I wrote about. And, in order to open up, I need to get in touch with my feminine side again... by crossdressing in front of that significant other I'm longing to meet?

You've concocted a scenario in which your ability to become intimate is dependent upon finding a woman who wants you to cross dress.

If this isn't an elaborate troll, it does sound like you're stacking the odds against yourself and putting up quite a barrier to intimacy.

10

I don't know how to help with your emotional issues, or what to suggest except professional help if you feel you need to resolve deep seated issues, but I can tell you that cross dressing is a gender thing, who you desire to sleep with is a sexual orientation thing and the two have no bearing on each other. In other words...dressing as a female will NOT change your desires to suddenly start wanting to sleep with men. Changing your gender most often does not change who you are attracted to. A man could be entirely straight then go through a sex change, turning to female and still he will be attracted to women and will therefore be a lesbian I guess. Hope this makes sense.

The point is...gender has no bearing on your sexual desires. You cannot help what or who you are attracted to and if that is women, then it won't suddenly change to men just because you slip on a pair of lace panties. I mean...its kinda like assuming a man must be secretly gay if he enjoys something inside his ass. In other words...illogical.

I dunno if dressing as female will help resolve issues. Probably not UNLESS those issues are specifically caused by having a desire to dress or be female and supressed them for years and years. However, there is no harm in experimenting with it either and you should try not to overthink it. If this is a desire for you and a sexual turn on...just let it be what it is. There are LOTS of men who enjoy this fantasy and lots of men who fulfill it with their partners.

As for your mental block regarding intimacy and how deep it all goes, I think a psychologist or someone professional would be more apt to help overcome those kind of barriers.

11

Have you actually tried just dressing up as a girl? You'd be amazed at what it can do for some people, as has been said as well it doesn't change your sexuality at all... unless you went the whole way with surgery etc to become a woman, in which case you'd be a lesbian, but you don't need to do that at all.

12

I have loved to wear female underwear for years and just recently took the huge step to tell my partner. It was a difficult task to tell her, but I am so pleased that I have. She loves it so much and just what this lead to, I'm not sure, but it will be fun! She will be bringing me a little gift or two this Saturday when she visits me next. I can't wait.

13

If you do join fetlife I recommend joining this group https://fetlife.com/groups/45663

The group owner is very good on this topic, and she focuses on it when Mistressing. I've met one of her subs who is a trans cross dresser, but I believe she has sissified non-trans men too.

I've had very little experience. I've known a guy who purely found cross dressing fun, he was bi sexual. I saw one guy who wanted to dress up as a girl for a new experience and to prove how much he trusted me, he was striaght. And then I've put a sub in womens clothes, and well, he hated it so much, it almost broke him.

I have found that with these men cross dressing has not altered their sexual orientation. Even when experimenting with subs who are forced to perform bisexual act, those subs are already bi. I wouldn't be able to perform that form of play if a sub wasn't bi (although I wouldn't do it if they were striaght as that's not ethical).

14

My boyfriend is a cisgendered (i.e. not trans) male, but he enjoys wearing my clothes.
It's a huge turn on for me and he likes skirts a lot, so it works out well for us both!

You shouldn't be afraid of what you like because in the end, it's only clothing that has been branded as 'feminine' by society anyway. Like, why the stigma?

And if it turns out that it's not for you, then that's okay too. Just enjoy your curiosities rather than try to block them out! -w-

I know loads of girls who love boys crossdressing, and vice versa. That's just my opinion though. It's not too dificult to find someone who won't help you indulge, I'm sure.

Good luck! <3

15

Just Jenson wrote:

you will never knwo the true reason until you start to explore it. furthermore, the true reason, or what you think is the true reason, may keep on changing as you change and become more involved or distracted away from dressing.

It is something I have toyed with myself for years and years and still have not got to the true reason.

At the moment however it is something that simply turns me on and makes me feel good sometimes.

Like you, i did think it would help me get closer to a partner as for me, dressing is also part of my submissive side. A million questions have run through my head over the years and I still havent found the answer.

Just know this - as you explore this road, there will be great times and not so great times - as with anything - so just go with it if you feel it is the way ou want to go and slow down when you feel you dont want to explore it for a while.

Thank you.

I'm questioning where does it come from, and why, and etcetera. Pleasure doesn't need any explanation. Looking for one is a sign of not being really enjoying it.

Probably it will be better to leave it for further.

16

rose hip wrote:

wonderlost wrote:

a brand-new problem created by me myself, in order to keep me from taking matters in my own hands, right here right now.

That was my guess after reading this:

I'm not interested in doing it for myself. I want to do it for my eventual significant other, as a way of allowing myself to trust and giving myself to them. Yet, in order to find a significant other, I must open up and get over this emotional block I wrote about. And, in order to open up, I need to get in touch with my feminine side again... by crossdressing in front of that significant other I'm longing to meet?

You've concocted a scenario in which your ability to become intimate is dependent upon finding a woman who wants you to cross dress.

If this isn't an elaborate troll, it does sound like you're stacking the odds against yourself and putting up quite a barrier to intimacy.

(Sorry, I don't know how to multi-quote, if it's possible)

Thank you too.

"...it does sound like you're stacking the odds against yourself and putting up quite a barrier to intimacy."

Yes, that's the problem, I guess. Trust me, I'm not a troll. I don't see the point not only in wasting your time, but also wasting mine trying to put together an idea in a language that it's not my native language.

Despite your suspicion (which it's totally valid, since you don't know me at all), your post was very insightful and thoughtful. Thank you once again.

17

Fluffbags wrote:

I don't know how to help with your emotional issues, or what to suggest except professional help if you feel you need to resolve deep seated issues, but I can tell you that cross dressing is a gender thing, who you desire to sleep with is a sexual orientation thing and the two have no bearing on each other. In other words...dressing as a female will NOT change your desires to suddenly start wanting to sleep with men. Changing your gender most often does not change who you are attracted to. A man could be entirely straight then go through a sex change, turning to female and still he will be attracted to women and will therefore be a lesbian I guess. Hope this makes sense.

The point is...gender has no bearing on your sexual desires. You cannot help what or who you are attracted to and if that is women, then it won't suddenly change to men just because you slip on a pair of lace panties. I mean...its kinda like assuming a man must be secretly gay if he enjoys something inside his ass. In other words...illogical.

I dunno if dressing as female will help resolve issues. Probably not UNLESS those issues are specifically caused by having a desire to dress or be female and supressed them for years and years. However, there is no harm in experimenting with it either and you should try not to overthink it. If this is a desire for you and a sexual turn on...just let it be what it is. There are LOTS of men who enjoy this fantasy and lots of men who fulfill it with their partners.

As for your mental block regarding intimacy and how deep it all goes, I think a psychologist or someone professional would be more apt to help overcome those kind of barriers.

Hi, thank you.

As I stated before, I'm not afraid of being gay. Yet, your post is quite illustrative. It helped me to learn a few more things which I didn't know about, and I will keep them in mind if one day I decide to try crossdressing with my significant other.

18

Ashe wrote:

Have you actually tried just dressing up as a girl? You'd be amazed at what it can do for some people, as has been said as well it doesn't change your sexuality at all... unless you went the whole way with surgery etc to become a woman, in which case you'd be a lesbian, but you don't need to do that at all.

Hi.

I didn't try it, I must say. Not at all. Now that you mention it, I guess it would be an interesting thing to do for and by myself first, instead of looking for a woman who is eager to fulfill that fantasy. I mean... Maybe I should not depend on anybody else's point of view and try things for my own pleasure, if I'm really into such fantasy. Thank you.

19

Brian47 wrote:

I have loved to wear female underwear for years and just recently took the huge step to tell my partner. It was a difficult task to tell her, but I am so pleased that I have. She loves it so much and just what this lead to, I'm not sure, but it will be fun! She will be bringing me a little gift or two this Saturday when she visits me next. I can't wait.

Lucky you! You seem to be several stages ahead from me.

20

The Nymphomaniac wrote:

If you do join fetlife I recommend joining this group https://fetlife.com/groups/45663

The group owner is very good on this topic, and she focuses on it when Mistressing. I've met one of her subs who is a trans cross dresser, but I believe she has sissified non-trans men too.

I've had very little experience. I've known a guy who purely found cross dressing fun, he was bi sexual. I saw one guy who wanted to dress up as a girl for a new experience and to prove how much he trusted me, he was striaght. And then I've put a sub in womens clothes, and well, he hated it so much, it almost broke him.

I have found that with these men cross dressing has not altered their sexual orientation. Even when experimenting with subs who are forced to perform bisexual act, those subs are already bi. I wouldn't be able to perform that form of play if a sub wasn't bi (although I wouldn't do it if they were striaght as that's not ethical).

Cool. I was wondering also whether combining crossdressing and submission would end up in forced homosexuality or any other practice against one's will. It's good to know that, since I'm a little attracted to BDSM, too. Thank you.