Skip to content

Your Ladyboy Date is a virgin

This post was last updated on .

I feel silly writing this but I think it’s something that’s worth talking about. I’m a fan of the series Jane the Virgin and it inspired me to write about this topic. We all know that most Asians believe in saving their virginity for the right man (not me, lol) as our culture puts it in high regard.

What will you do if you find out that the ladyboy date you’ve been chatting with is a virgin and you are so into her sexually? Dun dun dun… Alright, Jimmy, or whatever your name is. Drop your gun (metaphorically) and listen to me.

There is nothing you can do but WAIT.  If you are really into your ladyboy date, you have to respect her views in life.  I think that in this situation, you should be the one to compromise. If you can’t, simply look for other options.

Compatibility is Out of this World… BUT

I know how very rare it is for you to find compatibility with someone whose cultural background is so different from yours but the nagging thing about her is that she’s trying to save herself before marriage. If she’s naïve about your attraction with her wee-wee, please slow down.

a ladyboy and her boyfriend

I know that it sucks to be in your place right now but do you really want to take risks in turning her off just because you want to get your way into her pants?  If the compatibility and everything seems to mesh well with you and her, be patient.

Below is a list of more in-depth reasons why you can’t easily get into her pants.

Fear of being labeled a Slut

Globally, women who have an active sex life with different men are labeled sluts. This is wrong but this is the reality. In the east, the majority of the people don’t think of slut as a meaningless word. Some take it to heart and don’t want to be associated with it.

This is the very reason why you may encounter a lot of ladyboy virgins. This is not to say that all Asian ladyboys thrive in their virginity. However, their virginity may be something that they can be proud of in a sense.

She wants IT to be Special

Ladyboy virgins probably still have a notion that their first sexual encounter must be extra special. Because online dating sites have a considerably large number of perverts, they may feel that you’re only after having sex with ladyboys in rotation. If she does not feel like she doesn’t have a special connection with you, there’s a low possibility that she’ll get in bed with you.

Is she your Ladyboy Girlfriend?

To sum this section up, she must be your ladyboy girlfriend. If she’s already in an exclusive relationship with you, you’ve got the two things above covered. It may be hard to commit to a relationship just for the sex so, at the end of the day, the decision is yours.

However, committing to someone just to test the waters out is usually a bad move. Just imagine the explosions of emotions should both of you not work out. Imagine breaking the heart of someone who gave all of herself just for you. Will you be able to live with the guilt?

She’s not a Total Prude

Please don’t get me wrong. I’m not saying that virgins are prudes, I just want to make things clickbaity for you to focus on me lol. If she knows how sex goes (ok that sounds shady Amanda) and she likes talking about it with you, maybe you can convince her to do some fun things without the penetration.

Maki and Cyril

You can do long French-kisses and go second base.  There are a lot of ways to reach orgasm without popping the cherry.  Be creative and always know that there’s no greater power than the power of visuals.

Wear sexy costumes to make things more exciting that you don’t feel the need to enter uncharted land just to reach nirvana.  You know what they say, a real friend always lends a hand… or mouth LOL.

Oral Sex

To further elaborate this section, you must resort to oral sex. If she’s open to other stuff other than penetration, thank your lucky stars. Think of this as mastering something. Wouldn’t it be amazing to not only give and receive head for less than three minutes?

There are many ways to master the art of a good blowjob. The use of the tongue, exercising the gag reflex, teeth placement, and making proper use of the saliva, are all very interesting, not to mention, highly sensate stuff.

Eating Other Areas

It’s not just the genitals that deserve love. Other body parts need tender loving care as well. Some areas that you can explore are the anus, feet, hands, belly button, neck, ears, chest, nipples, armpits, thighs, butt, etc.

Make it extra spicy by incorporating soft bites as well. This is an amazing way to express your love for each other without having the need to pump anything.

Erotic Massage

Finally, if you want to enjoy with a ladyboy who’s stern in maintaining her virginity, you could introduce her to an erotic massage. Erotic massages are amazing as these don’t only help one release, these also greatly helps with relaxation.

You could look up lingam massage as this will be the most pleasurable. It specializes in perfecting the sensations from touching one’s penis. However, if you’d also like to take care of your anus, you could ask her to look up prostate massage. Just know that this involves inserting finger/s in the rectum so she may not be interested in receiving one.

If she’s not ready for focusing on the genitals and private areas yet, you guys could explore Nuru massage. It’s the type that requires one to rub their body against another’s using an odorless oil. It’s sensual, passionate, yet not too invasive.

Furthermore, if she’s a Thai ladyboy, there’s a chance that she’s aware of what a Thai massage is. Maybe she could perform it for you in a less professional way. However, don’t ask this explicitly as she may be offended.

She’s Disinterested in Sex

We all have that friend who is not comfortable with the talk of sex.  Maybe your ladyboy date is asexual, I don’t really know the situation.  Be sensitive and find a way to gently lure her into the conversation about making love.  If she really has no interest in it and you’re like me who can’t live without sex, what are you waiting for? Hop on the passenger seat and let’s go far far away lol.

a ladyboy and her boyfriend

Seriously, waiting for the right man to have sex is one thing but someone who doesn’t even masturbate… that’s a whole different story.  If you like the restraint and find it sexy, it’s up to you.  Love makes you do crazy things but it shouldn’t turn you crazy (as a person).

However, you must know that not all ladyboys don’t have sex just for the reason of not wanting to. They’re also not doing it to piss you off or test your patience. Some reasons can cute quite deep and to be educated on these, keep reading.

She isn’t comfortable with her Penis

Because a lot of ladyboys have elevated levels of gender dysphoria, there are some who are uncomfortable with their penises. Some are so uncomfortable that they even close their eyes whenever they take showers. If she declines to have sex with you because she’s ashamed of having a penis, don’t force her to have sex with you.

Most ladyboys who are uncomfortable with their penises turn out to have amazing sex lives after a sex reassignment surgery. If you can wait for her to achieve this goal, there’s a huge chance that she’d gladly give away her virginity to you.

No Anal Sex

You may argue that if she’s not comfortable with having a penis, you can still use her anus. However, you must know that there are ladyboys who aren’t comfortable with anal sex as well. Some of them associate anal sex with gay sex and they don’t want to feel like they’re men by participating in it.

This is why it’s very important to have a deep conversation with her before assuming that she’s disinterested in you. If you open up yourself to her, she will feel that she can trust you.

Try having more meaningful conversations with her before opening up this topic. This will signal her to think that you’re not just interested in her body. Patience is key when it comes to dealing with a virgin.

You may Come on Too STRONG

The last possible reason why she’s disinterested in sex is maybe you come on too strong. Don’t talk about a lot of fetishes and kinks from the get-go. This will intimidate her and might result in her, thinking of you as nothing but a pervert.

Don’t be too hasty when you’re having conversations in regards to sex with a virgin. This is the cardinal mistake that you can make. Just relax and let the sex conversations flow naturally. Stop pushing her to the limit as she may get scared and run away.

Try Dating other Ladyboys

If you’ve done everything to understand her and be there for her but she’s still not comfortable in having sexual relationships with you, it’s best to seek another partner.

MyLadyboyDate founders

My Ladyboy Date is filled with beautiful and open-minded ladyboys who are looking for love. A challenge is quite thrilling and exhilarating. However, at the end of the day, compatibility in all aspects of life is still what matters when it comes to a life-long partnership.

Good luck!



Posted in Love & dating, Product updates

About the author

Amanda Valentine Dela Cruz
Just a random trans woman playing with makeup and skincare. Loves bacon and the operating table. I'm also the author of the dating guide book Dating Transgender Women for Gentlemen. Know more ->

Related posts


Leave a Reply

Your email address will not be published. Required fields are marked *