He's gay

I wouldn't be able to do it personally, my vagina would dry up and clam shut at a full grown man even saying the word sissy. 🤢

I think if he admits to being sucked he has had to have tried penetration... that is what bi-sexual means. If he had plans to be with just you he wouldn’t tell you like this he would reframe it like I went through some stuff trying to figure out who I am and I experimented, it was fun at the time but when I’m with you I know I’m not that guy. The way he makes it sound is I know who I am if you want me you have to accept me like this.
He won’t change, he will pull you into his kinky world and you will find him in bed one day with a dude. The next step will be inviting one of his bi buddies with you for a threesome.

If you want a relationship with this person then go for it. A straight person who enters into a monogamous relationship is giving up pursuing sex with other people, it's the same for a bi person, yet I don't see people saying, "nah you should run away from the straight guy you're interested in, he'll just cheat because he still wants other ladies".

There's a saddening amount of bi-phobia and bi-erasure in a lot of the comments above. Bi men aren't gay, they're bi, just like bi women aren't gay, or straight ladies experimenting, they're bi. It's possible for people to be attracted to people of more than one gender! It's real, it happens, but sometimes people hide this fact about themselves because of the bullshit like the comments above. If he tells you he's bi then have the decency to believe him.

If you want a monogamous relationship then tell him that, don't just assume he'll know (this goes for everyone, not just someone dating a bi person). If you think one day you'd be open to an open relationship, tell him you want monogamy for now and can't guarantee anything but maybe one day you would consider opening things.

If you're concerned about STIs then be honest with him; STIs can be transferred regardless of who is bonking whom, why don't you suggest you both get screened to be on the safe side? Also, not every gay or bi man likes anal so don't assume he's lying to you.

I can't tell by the way you phrased it about the ladies' underwear thing; did he actually tell you he wears them, and he identifies as a sissy because of that? Or do you just think that sissy = wears ladies'underwear. What are your concerns about this? You could talk to him to find out more. Is it a secret pleasure thing, he likes going about his day with this little transgression nobody knows? Is it something he wants you to humiliate him for in the bedroom? Does he expect a dominant partner?

It's ok to be vanilla in bed, but it's also ok to be a little (or a lot) kinky. Maybe you've got a few quirks you'd like to explore with a safe partner. Maybe you're a little intrigued by what he's saying.

At the end of the day YOU and HE are the only ones who'd be in this relationship. What does it matter what a bunch of anonymous strangers think of it? Stop worrying about what others think of this guy's preferences, because that's pointless. How do you feel about him? If nobody ever knew what you knew, if you removed all feelings of shame and external influence, would you date him?

Not a good idea, walk away.

Just walk away

Hmm 🚩🚩🚩🚩🚩🚩🚩🚩

Sounds like he's still quite inquisitive given that he's only gone so far, such could present a problem down the track. Or he's lying about not doing anything more than he's stated.

Calling himself a 'sissy' for wearing women's underwear send a bit 'humiliation fetishist' to me, which is something I'd personally have an issue with on a long-term partner.

Are you considering him long term? Personally, I'd have fun, then move on. It seems a bit too risky.

Run. The ones who say they are bi always end up full blown gay.

Id just want to be sure if he was having safe sex. Although thats also true for sex with a female.

Yeah, nah

I remember Carrie in sex and the city dating a bi guy saying she feels insecure and jealous of men and women she didn't know who he was checking out! I would be insecure but my main worry was if you were exclusive and then got married etc would you be enough for him to not engage with other men. I would worry he might cheat. I reckon just stay friends or occasionally fuck buddy fun but nothing more

Ummm if you’re ok with your man enjoying d**k regardless in which fashion then go for it. For me it’s a straight out no thank you next! You can accept who he is but doesn’t mean you need to enter a relationship if it doesn’t sit right with you.

I think it would only be a problem if he's not exclusive in our relationship. Otherwise if he's all about me, who cares about the underwear?

Don’t go there, walk away. You will never satisfy him.