New to Sex with a Person with a Vagina

[Anonymous]

Hey everyone,

I used to be very active on here over 4 years ago, but I'd rather make this post anonymously.

I'm a trans man and I've identified as gay my entire life, I've only ever been into masculine presenting people and dicks. I still am and I still identify as gay, but for over a month now I have been very happily in a relationship with someone who was assigned female at birth. My partner is agender but presents in a traditionally feminine way and I'm attracted to that (though this attraction only applies to them). Our relationship is a long-distance one, but we will be meeting up very soon and are very excited to get to the sexual aspect of it!

My issue is: I'm nervous because I've never been attracted to breasts and a vagina before, but I am attracted to theirs. I've never had sex with someone with this set of genitals. I want to prepare somehow and give them the best experience they can get. I was wondering if some folks on here might have some advice for me - how do I make sure I don't disappoint?

Thanks so much in advance everyone!

[Pyromancer]

When you say that you're a trans man, am I correct in assuming that you were assigned male at birth but now identify as female? But you still have male sexual organs? And your partner is agender but was assigned female at birth? Forgive all the questions, but I have 2 friends who were born female but now identify as trans men. So I want to be sure.

From what you describe, this isn't just going to be a one-off...this is someone you care about and want to build a relationship with. So why not start out being completely honest...telling your partner that this is something you've never done before and you want to make it good for them. I think that showing genuine affection...kissing, touching, caressing...would help set the mood for both of you.

As the two of you grow in intimacy, you'll learn each others bodies and learn what each other likes. Don't be nervous, treat it as an adventure! And as I said, above all...communication and honesty.

[Anonymous]

Hey!

Like your friends, I was assigned female at birth but identify as male.

Thanks for the advice! I agree that honesty and openness are key.

[Jae]

Dive in and have fun. Maybe you are more afraid of the body contact than you are the actual acts of sex. Show respect of course, offer to use a condom, she may or may not want to, but at least you offered. Sliding your cock into a wet pussy will be an unbelievable experience for you especially when you are at full shaft deep inside her. Rest there for a bit, throb your dick insider her, you'll feel like your ready to explode. She'll have a good time of it for sure, you can pet her when you are both done, getting ready for round 2.

[Pyromancer]

Dive in and have fun. Maybe you are more afraid of the body contact than you are the actual acts of sex. Show respect of course, offer to use a condom, she may or may not want to, but at least you offered. Sliding your cock into a wet pussy will be an unbelievable experience for you especially when you are at full shaft deep inside her. Rest there for a bit, throb your dick insider her, you'll feel like your ready to explode. She'll have a good time of it for sure, you can pet her when you are both done, getting ready for round 2.

If you read what this poster said, he was assigned female at birth but has always identified as male...so there's no hard cock, throbbing or otherwise, to slide anywhere...

[Jae]

I got more confused the more I read it. Needless to say, S-E-X is to be fun, have it!

[TwisttheLeaf]

There is no "set guide" or tried and true technique to "fucking a vagina" (other than lube and/or natural lubricant is important). Individual tastes, sensations, sensitivities, etc are (in my experience) especially relative to that part of the anatomy.

Tell your partner that you're new at sex in this particular situation and -ask- them what they like. Ask them to guide you through the first experience because you want to make sure it's good for them. Most will find the fact you asked and are looking out for their needs and desires extremely attractive.

[princealbertofb]

Quite honestly, I'd say what we generally say here, which is : just ask them what they'd like you to do to them and how. It's probably better than asking us what to do and how to do it. We have no guarantee that what we'll say will be in any way relevant to the way they want you to worship their body, not matter what set of genitals they may have. I think you'll probably find what makes them tick after you get down to it, but really, just ask.

[Cuddly]

I like Pyromancer's reply.