Would you have sex with a ladyboy?

[Anonymous]

I've been talking on the phone and texting and swapping pictures with this ladyboy I met online. A date is imminent, I've been stalling because I'm still unsure how me and my buddy under my belt will react at the end of the night when moment ahem.. comes. Its definitely going to be a sex date too. She isn't beating around the bush like a real woman does.

So should I do it?
What do you think?

[AndyOh]

I would ask how do you feel now when you are jacking off and thinking about this Ladyboy? I mean after you blow... Do you feel guilt or something? Because that is probably how you are going to feel when you are with him/her. I would just meet, relax, and see where it goes.

[Checkmate5345]

Doesn't make you gay either bro. Fuck her brains out, plus she'll prolly give the best head of all time.

[Asker]

I actually ended up going through with it. Slightly different angle even to anal with a woman so took some getting used to at first but I ended up getting there in the end. She was very clean though. Nothing on my dick at all and I had sex with her 3 times. I've done anal with women who didn't know how to get clean back there. The only awkward thing about it was that her penis was actually bigger than mine and mine isn't exactly small so that was a bit of a surprise. Was pretty much impossible not to come into contact with it at all but I was able to get past that cause she had nice perky boobs and a nice, smooth body

[Pete671]

Nice!, I've taken anal from ladyboys and it was awesome, just letting go of my inhibitions is very theraputic

[ElissaDido]

I wouldn't have sex with women.
I wouldn't have sex with a transgender women (a man).
I wouldn't have sex with a transgender man (a woman).
I would only have sex with a biological man.

[ElissaDido]

* transgender woman But you can do whatever you want.

[Asker]

So do you think I should do it?

[ElissaDido]

If I were you I wouldn't do it. But I'm not you...

[Asker]

I see what you're saying, like if you were you but in my body you wouldn't. That's OK if that's the only way you can see the situation. Thanks for answering.

[Anonymous]

You've already gotten this far, may as well follow through with it.

[Asker]

I agree there isn't really any turning back now unless she backs out

[SarahsSummer]

Go for it. Everybody deserves love. Even men with boobs.

[Asker]

LMFAO!

[Checkmate5345]

It's a chick with a dick

[SarahsSummer]

@Checkmate5345 don't fool yourself.

[Checkmate5345]

Don't fool yourself, it's the inside that counts, that's why it goes first. These are real females on the inside, and it is a straight fantasy for a reason. No gay guys like them. Their soul is a chick's and god gave them a dick, to blame them for it is rude and unfair. I've met girls who are men on the inside too. It's your actions and character that define who you are, not your equipment.

[samhradh_leannan]

I wouldn't do it, but that doesn't mean you shouldn't.

[aficionado]

I wouldn't do it, but if you wish to, go ahead! It's not 'wrong'.

[Asker]

Why wouldn't you, what stops you?

[NJ_Casanova]

If you are into it go ahead.. at least you know what your dealing with. I think if "She" didn't bring it up before hand... there would definitely be some violence happening.

[boomstheory]

If nobody would find out

[ThisDudeHere]

I dunno probably not. At least not while I'm still young. When I'm older and don't give a fuck and she looks 100% female then perhaps.

[Asker]

I wouldn't say she looks 100% female but pretty close like 88% to be exact Id say

[ThisDudeHere]

Well I guess I could do it but only if it's my dick going in to a hole, an not her's.

[Asker]

Yeah that's the idea. Only my dick is going into a hole. Hers isn't there as far as I'm concerned. If she needs to touch herself I'm cool with that but I'm not touching it unless she absolutely needs me to but no matter what I'm not putting my mouth on it

[ThisDudeHere]

Precisely. That is about the only boundary I would have if I were to ever do it.

[Asker]

Cool. So why not while you're young just out of curiosity?

[ThisDudeHere]

Dunno... feels odd. And I wouldn't want that in my history right now.

[Asker]

I see what yours saying, you wouldn't want your friends to know and you have other stuff you want to do first. In my case I've pretty much done everything sexual other than this so when she told me she was ladyboy I started to get intrigued. Think of it like a cheat way to get the platinum trophy for sex on PlayStation without actually doing the gay stage.

[PYTcassiaxo]

you don't do it!!! you done know what diseases she got! don't be stupid lol smh

[Asker]

That's a good point but condoms right? I'd definitely be using those, I mean this isn't the nice girl next door it's like the opposite. I know part of what I could be getting into

[PYTcassiaxo]

truuuuue just use condoms! haha

[BertMacklinFBI]

if you're chill with rubbing dicks then go for it

[Supergirl0812]

By ladyboy.. You mean transgender correct

[Asker]

Yes correct sorry but in my defence that's what she called herself. Her first exact words to me were "by the way I'm not real woman I am ladyboy" I think it's a Thai thing, that's just what they call themselves

[Supergirl0812]

Got it

[FalloutVaultB0y]

I wouldn't do it. I'll only have sex with an actual, biological female given an option.
But hey, morality is completely subjective. There is nothing inherently wrong with doing it. It's totally up to you, man :)

[Notreallyhere]

She's a person like anyone else. If you feel like fuckin then do it and have a new experience. If it grosses you out then let her down easy and explain why.

[Asker]

Thanks. What should I say to let her down easy if the worst happens? Cause this is actually what I'm worried about and pretty much what I have posted this question

[Notreallyhere]

The easiest way is to just be honest. Not brutally honest, but honest. Tell her that you don't feel as comfortable with it as you thought you would, then hope she understands.

[Asker]

I'll just hope she lost her man strength during the transition if she doesn't take it well lol

[PatrickBateman]

If you're not sure you want to (I'm presuming you're not sure since you're asking strangers online) you probably shouldn't

[Kylesar]

I'd go for it
If I'm that attracted to her, what's downstairs matters not to me

[Asker]

You must have a good heart. It will be a test if mine is as true as yours

[Words_and_Wisdom]

As long as she knows how to use the tool given to her then hell yeah why not.

[Asker]

What do you mean by that? I'm playing the male role so to speak just to be clea about that.

[Words_and_Wisdom]

I'll be a sub for a lady boy if she was hot enough. I find the feminine body, face, and voice attractive, but can go either way with what she's sporting down there. In other words, if she looks like a woman and has the voice of a woman, I'd let her fuck me.

[Asker]

But would you fuck her?

[Asker]

As in you put your dick in her, not the other way around

[Words_and_Wisdom]

Sure.

[funny_strange_man]

I would since I am bi. For some reason not with a lady ---> guy.

[Asker]

Yeah that would seem weird. I'm with you on that one. Don't know why but that just seems weird.

[funny_strange_man]

@Asker I have met some who seem cool but rather be with a lady, guy or guy who looks like a lady

[jwhit]

I wouldn't, but it's your life man do what you want.

[Asker]

That it is

[Noxifer626]

Wear a condom and enjoy it. She's a woman after all.
At least that's what I think.

[TheOldMan59]

I wouldn't. But I won't tell you what to do. I merely advise and recommend.

[happymike16]

Maybe you like dick

[Anonymous]

Yeah. I like women and I like dick, but not guys, weirdly enough, so I'd probably take a chance and go for it.

[Anonymous]

I'd treat herher like the lady she desires to be

[Anonymous]

OH
HELL
MUTHA
FUCKIN
NO

[BertMacklinFBI]

lol.

[Anonymous]

Yes sure

[Anonymous]

If i was single id go for it. Try something new

[Asker]

That's what I'm thinking. In the pictures she has sent me it shows everything and yes it shows that but she actually has a really nice body, good booty. Boobs look pretty fake but she doesn't have full man shoulders and stuff like she's obviously been on the hormones for years. And it's guaranteed anal so I'm actually thinking I'll be fine just that little crack of uncertainty shining under the door know what I mean?