Would you date a sissy?

[Shyfemguy]

Let's say he's a nice gentle shy guy and he likes women like all other guys but he has a weakness for crossdressing and wearing makeup in private, would you date such a guy?

[coldmarch]

I did, twice, but that wasn't their main "point", just a side kink. And I don't think I would date anyone with a strong kink that takes a too high relevance in their life, because I wouldn't be compatible with that lifestyle.
If you want to increase your chances to get dates, I think you should put yourself first and not present yourself as a "sissy", or to even mention your kinks at the beginning. You're much more than your kinks I hope, and you can give much more in a relationship, than that. Women you could potentially date are most likely not looking for your kinks, but for a relationship with a guy who can give them also a "regular" sexual life as well, and who can guide/protect them in the daily life (of course not all of them but this is a widespreaded preference). As long as your kinks don't overshadow what is considered normal sex, and they stay like a side thing that comes out only time to time, then you don't even need to mention that before dating someone.
Instead, if this is really important for you, then probably you should try to date girls who are already into this kind of things, for compatibility. I don't know exactly where to send you to find them but I think you would get more chances in environments that promote sexual freedoms (lgbt) or general progressivism (leftist activists).
Also, I think that if you get a girl who is like-minded to you (not about the kinks but about topics, interests, personality etc), then she would be more keen to "understand" you better and to connect better with you, as a friend too, not just a partner. In that case she would be more open minded to explore your kinks, or anyway to accept them.
Just try to not make it the main point of your sexual life because things would get really difficult and would potentially corner you to pay for femdom sessions.

[TacosRAwesome]

No thanks. I'd like to date someone with an intact man card.

[Shyfemguy]

I guess you want to date a real man, you don't want to date no tranny no, you want to date a real man!

[humanearth]

Nope, I hate Sissy Prissy girls.

I the like rough, tumble, get their hands and clothes dirty girls

[youngmix]

I only spend time with nice guys, I love gentle men, and I think you know how I feel about shyness (Girls, What do you think about shy men?

As for crossdressing and wearing makeup...
I generally find that to be extremely attractive, but he has to have a good fashion sense. Like, he has to look cute in what he is wearing, and he has to wear cute outfits. I'd definitely like to buy him a wardrobe and dress him up. I would like it if he shaved his legs as well, and kept his body mostly hairless, unless he already has very little hair. But that's just a preference, and not even close to a deal breaker.

Now, as for him *only* doing it in private...
I would probably put a considerable effort into pushing the boundaries on this.
My current preferences are for transgender females with or without breasts (born male, still have their male genitals, and may have taken hormones to grow breasts), and crossdressing men who are very effeminate.

I would want to dress him up real nice, get his makeup all cute, and take him out for a date night. I would want to eat something very light, maybe go to a movie, then put considerable time aside for intense PDAs, and show everyone how hot I think he is. I would work towards turning this kink into a lifestyle for him. Not necessarily for every day, he can dress however he likes, but for at least some days. I would want to show him off.

I live in areas where crossdressing in public is no problem.

Keeping a kinky little secret between us is nice as well, but I love the idea of him breaking free, even if it's an every now and then event. I don't think it would make sex any less hot, especially if he's very fem.

So a nice, gentle guy is perfect for me, especially if he's a shy guy, and even more so if he likes to crossdress. If that's how you define a sissy, then yeah, I'd date a sissy.

I would still need to know more about what he's into: his style, other kinks that he has developed, sexual desires that he has, and how he would be ready to explore. I live a particular lifestyle, and I am starting to get an understanding of the kind of relationships that I would like, so I would have to know if he is compatible with that as well.

Also, I want him to wear a collar when he crossdresses, with a dog license tag that has my initials on one side, and my lip prints in lipstick on the other side. I will make him different tags in different colored frames, paper, and lipstick for his different outfits.

He would have to be okay with being my little pet.

[Anonymous]

I already have a woman, I don't need two of them.

[Shyfemguy]

But 3 is more useful than 2

[LazerBean]

Absolutely not.

[Shyfemguy]

But why not?

[LazerBean]

If I wanted someone feminine I would go for another woman.

[Shyfemguy]

😭😭😭 but we need love too

[LazerBean]

I'm not stopping you from getting love, you just won't be getting mine lol

[Shyfemguy]

Ok, i hope a dominant woman sweeps me off my feet.