What should I expect on a date as a sissy crossdresser?



What should I expect on a date as a sissy crossdresser?


I am a sissy crossdresser, and when I go out on a date with any man, most of the time, I get disappointed.

The reason is that most men don’t know how to date sissy crossdressers.

Either they are very rude to us, or sometimes just clueless and boring.

Sometimes they want to do grand gestures, which is totally not my type of date as a sissy crossdresser.

Now, just like most other sissy crossdressers, I am tired of going on boring and

horrible dates and coming back home dry. I want to change this.

In this blog, I am going to share some important things that a sissy crossdresser wants from their dates.

It’s not that hard to have a happy and romantic date with a sissy crossdresser.


So let’s get started.



8 Things Sissy Crossdresser Want From Their Date


Make Me Feel Feminine


What should I expect on a date as a sissy crossdresser?


This is the first thing I want from my ideal date. Just makes me feel cute and feminine.

I want my date to recognize me as a woman and do all the textbook things that a man should do for his date.

It starts with coming on a date with some flowers, giving me compliments on my outfit,

being chivalrous, and leading the date like a man.


What should I expect on a date as a sissy crossdresser? 


Make sure you don’t cross the line by being homophobic or commenting

things like I just look like a girl or I am very passable.

All I want is not to be reminded that I am a man; I know that already.

Treat me like your queen and lead the date like my king.

I know this sounds very cheesy, but that’s how you can make a sissy crossdresser feel special.


I Want To Tell You About Myself


What should I expect on a date as a sissy crossdresser? 


Sissy crossdressers want people with whom they can share their feminine feelings and experiences.

Being a sissy crossdresser, I have very few people in my life with whom I can be myself.

So, I want a date who can listen to me when I pour out my feminine heart in front of him.

This is not just me; almost all sissy crossdressers want this from their dates.

We want to be heard, and we want to be reacted to.

For instance, I take great pleasure in sharing about my crossdressing journey,

about my first dress, my difficult times in my crossdressing journey, and everything around it.


What should I expect on a date as a sissy crossdresser? 


A sissy crossdresser expects her date not just to keep talking about himself but also to want to know us and listen to us.

And trust me, boys, I can easily tell whether you’re listening attentively and if you care about what I am saying.

So don’t just pretend to hear when you are on a date, but genuinely listen to what we are trying to tell you.


I Want to Know You


What should I expect on a date as a sissy crossdresser?


This is my priority and basically a necessity for any sissy crossdresser.

It’s one of the reasons why I usually agree to the date in the first place.

No matter what happens by the end of the night, the date should make both

of us feel comfortable around each other enough so that we can be more intimate with each other.

To be honest, I don’t want to go home with a person who I don’t know and trust fully.

This is the primary reason why sissy crossdressers love going on dates.

It gives us a chance to get to know others and see if they like crossdressers.


I Want to Feel Safe Around You


What should I expect on a date as a sissy crossdresser? 


Being a sissy crossdresser, I want to feel safe around the man I am dating.

As sissy crossdressers, we feel very vulnerable because of the social stigma around crossdressing.

The biggest concern sissy crossdressers have is privacy.

What if someone catches us and creates a mess out of it, or some random stranger starts bullying us?

That’s why the best thing a date can do is make his sissy feel comfortable and safe.


What should I expect on a date as a sissy crossdresser?


To make a sissy feel safer, you can start by opening up and introducing yourself.

Sissy crossdressers go on dates to do things we can’t do over text: see if the guy is genuinely good.

We go on dates to check for red flags, such as homophobia, being disrespectful, or rude to us or anyone.

Also, it gives us a chance to crossdress in public. Personally speaking, my purpose for going

on a date is to get to know one another, and if a man wants to land another date with me,

I need to see if you’re a nice guy first. Otherwise, what’s the point?


I Want You to Lead Me Like a Man


What should I expect on a date as a sissy crossdresser? 


Most sissy crossdressers are tired of being a man in their real lives.

Crossdressing and being a sissy is an escape for us to feel relaxed and true to what we are in reality.

So when we are dating, we want you to lead like a man and let us be the woman in the relationship.

A sissy crossdresser wants her date to be masculine to make her feel feminine.

When dating a sissy crossdresser, a man can do things like picking us up

for the date, paying the bill, being protective, and chivalrous.


What should I expect on a date as a sissy crossdresser? 


On my last date, my man booked a cab for me and dropped me home,

and it was the most romantic thing any man has done for me.

It made me feel so special and feminine.

That’s what we want from our date: just be the man and let us live the feminine vibes.


I Want To See If There’s A Follow-Up Date


What should I expect on a date as a sissy crossdresser? 


This is a pretty obvious thing. As a sissy crossdresser, all I want from a date is to see whether

my date passes my standards or not. I want to know if you are the kind of guy I could date

for a prolonged period and if there’ll be a follow-up date.

I am just testing if there’s enough compatibility and chemistry to keep seeing the man regardless

of what happens on the date and how much of an ideal date it is for me.

If I am being honest, most of the time, I come back with a broken heart.


I Want To Know That You Like Me


What should I expect on a trans date  


As a sissy crossdresser, all I want is a compliment, so I expect my date to compliment me.

Acknowledge what I am saying, and make me feel special and feminine. It’s not that hard.

This is also another significant aspect of a date, especially when dating a sissy crossdresser.

If you want to make a date as special as possible, make me feel liked and adored.

I want my date to let me know that he is actually interested in me and getting to know more about me.

So just validate me and make me feel special; that’s all I want, for god’s sake.

Do all those cheesy romantic things. Sissies love it.


You Make the First Move


What should I expect on a ttrans date 


Being a sissy crossdresser, I am the follower in the relationship, so I expect the man to make the first move.

Yes, we sissies love giving those flirty signals, but a man should be the one making the first move,

whether it’s kissing or taking me to his bed. Sissies like men who have this confident energy,

so go ahead, big boy, and take me home with you.




What should I expect on a trans date 


Dating a sissy crossdresser is not that hard. All we want is to be respected and treated like a woman on the date.

All we want is to know you, have some fun, and spend a night naked in your bedroom.

But that only happens if you treat us well, make us feel safe and protected, and be a really good gentleman on the date.

Sissy crossdressers like open-minded, progressive men who are chivalrous and treat us like their queens.


So all the men out there reading this, just man up and make us feel special and sexy, and we are all yours.


FAQs Sissy crossdresser


What should I expect on a date as a sissy crossdresser? 


Why do sissy crossdressers like being submissive?


There can be multiple reasons for that, but the most common one is that being submissive makes us feel more feminine.

The feeling of giving control to the man and being a follower in the relationship is a very relaxing and liberating feeling for sissy crossdressers.

Some sissies like being submissive not only in bed but also in life.

Being submissive takes us closer to our femininity.


Do sissies want long-term relationships?


Of course, we do want long-term relationships, but that doesn’t mean we are desperate and ready to settle with anyone.

An ideal man for a sissy crossdresser is someone open-minded and progressive enough to date us and take pride in it.

He shouldn’t have a fragile masculine personality that gets harmed by dating a crossdresser.

If a man likes us for who we are and respects our choices, then why not? I would marry such a man. Hmm, it’s such a dream.


Do sissies not date women?


That’s not true at all. There are a lot of sissy crossdressers who are into women and want to

be in a relationship with a woman. Some sissy crossdressers swing both ways, men and women,

so there’s no doubt about that.

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