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Sex with transgender woman?

T

the crony

Greenlighter
Joined
May 5, 2015
Messages
2
For the past few months I have been dating a very lovely transgender woman. I'm not the kind of guy who chases those types or sees himself with them, it just kind of happened. We had a class together..she is fresh from the great country of Brazil and didn't speak English too well so I offered to help out. An absolutely gorgeous girl with a great figure and (go figure) big big booty. Studying turned into lunch which turned into dinner over time. On one of our early dates, she made sure that I knew she was trans before we proceeded any further. I was pretty sure. I told her I was completely fine and supportive of it. We have since held hands, kissed and made out on a number of occasions. I enjoy holding her in my arms. I have felt her penis through her clothes on a few occasions, both erect and flaccid. When she sits on my lap I sometimes feel her balls. It was a little shocking to me at first but not in a bad way.

This weekend her parents are out of town on big business and she has her house to herself. She is inviting me over for a "special weekend" which means we will likely have sex for the first time. I'm just wondering how to approach it. I'm still a bit apprehensive about her having a dick but I don't think it will be too much of an issue. She likes that I am very much a straight guy and not someone who likes her because of that. She has said that she attracts many bi/homosexual men who like her because she has a dick. She kicks them to the curb.

I feel like I can't assume that she's into anal just because she's transgender. If she is I'm guessing that I would penetrate her that way. If she isn't I'm guessing I could just rub my dick between her legs to get off. And I know that at some point her cock is going to come into play and I really have no idea what to expect. Any insight would be appreciated.

She's going to Brazil for 3 weeks in August and is hinting that she wants to bring me with her. By that time I would like to be fully comfortable having sex with this beautiful, special woman.
 
Honestly if you are attracted to her in every other way, you shouldn't have too much to worry about.

It is ultimately going to have to come down to communication between the two of you. Your expectations, your worries, your questions.
You already said you don't want to assume she wants anal just because she is Trans, that's good. Try not to assume anything. Since you guys seem so close already, and you seem rather mature about the situation, it shouldn't be too hard to bbring it up, right?
 
Congratulations on your new relationship and also on not being too insecure/transphobic to take a chance on this nice lady!

It's totally normal for straight men to be attracted to transgender women. But I think you know that.

If you're uncertain about what to do in bed, just go slowly and ask her what she likes. I'm pretty sure she'll have a better idea of what's going to work than you do. Good communication is the basis for good sex.

Good luck! I hope it's mindblowing.
 
You'll probably find that your knowledge of your own penis will translate naturally when handling somebody else's. You know what feels good to you, so use that to your advantage (in a sense, you're already an expert!). Any time you have sex with any new woman you have to 'feel it out', so just attempt to be observant and listen to your intuition.

It's natural to be a little nervous about the dick (or any new territory for that matter) - as far as 'first times' go, that's a big one (if you're lucky anyway ;)). I'm sure she'll understand and should be perfectly willing to walk you through it.

I've experienced some hilarious 'snags' during my first encounter with some of my partners. I think the longer you wait to have sex with somebody, the more time tension has to build. Sometimes when I decide to 'take it slow' with somebody, a LOT of tension accumulates, and sometimes the initial sexual encounter winds up full of blunders, bloopers, and follies. When it's somebody you really care about, you've got plenty of time to discover each others' bodies and allow a dynamism to develop. You can always look back on the first time together and laugh.
 
If she wants you to have sex with her, she will probably let you use her back door pussy.
You need to explore what she likes. Perhaps she will suck you and not let you behind.
Some pre-op women can enjoy anal, and some will derive pleasure from the penis.
It's all rather complicated and there are really no standard rules as everybody is different.
If this is a genuine relationship talking to each other is the most important thing you can do.
 
Transgender relationships are usually... complicated. I've had sex with a transgender male (no operations), so he was hairier than women (duh)... slightly odd experience. The shots also cause the clit to enlarge - so it was largest clit I ever sucked and played with. I got hit on by a post-op man, who I had meet years earlier as a girl once (small talk that I had long since forgotten) This was years ago, when transgender and sex-change was very NEW to me. It was meeting a pre-op woman (as a friend) that changed my mind that they are "strange / freaks" - to, this is not a gay man who wants to look like a women... but I felt, was interacting with a woman (who has a penis).

Anyway, his body language and eyes was "hitting on me" - while we still had an enjoyable conversation. The beard and other unknowns made me not interested. Curious... yes. Unlike some post-op guys, He was quite slender... not the usual "big guy" post-op we see.

So Crony: I give you kudos for actually SEEING past gender and being in love with the person. (I meet my wife, while she was dressed to pick up chicks - but we clicked for amazing and strange reasons - people are, sometimes amazing, eh?)
Many (if not most) gay men are not interested in transgender woman. So they are usually limited to bisexuals.

It seems like you both are young... Let her be in charge and/or be honest and yourself. - especially if you are a virgin. Just being touched or kissed by my wife can make my day, and start an erection because the attraction is to her as a person, not the sex organ bits.

Hope you two have a fun and amazing weekend.
 
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