How to please a crossdressed ladyfriend

[Sting_Rae]

Hey folks! I know that explicitly sexual discussions aren't supposed to be posted here but I want to make clear that I'm asking for help finding information about sexuality and, having looked everywhere I could think of, I'm posting on this page in good faith and with the best of intentions.

I'm a cis woman and I've recently started dating a male-bodied person who will be seeing me as her feminine cross-dressed persona. I've never dated anyone like her before but it seems pretty natural to me to make love to her like a woman because she is so feminine. While the general idea of making love to her like a woman isn't a problem, the mechanics of touching her male genitals as if they were female ones throws me. I'm not sure how I should do this. It feels very much like I'm calling it one thing while doing something else and I would like for her to be able to feel as feminine as possible while it take care of her because I know how important that is to her. Does anybody know where I can find some good information on to touch/perform oral sex on male genitals in a way that's more like touching female ones?

[DeeArel]

Just go with the flow.

[Jacqueline Winona]

Wish you had 10 posts so you could get private messages, sting rae! The answers you'll get will be vanilla out of necessity, and I don't know any sources you could review, but I'd recommend thinking of what you like and that should be good. I assume your partner is a CD and not looking to transition, of course, as I can only help you with the CD part. Assuming again he is a crossdresser and thinks that way, he is still a guy . . .

[Kathi Lake]

Silly thought; You could always ask.

Kathi

[candicd]

Communication is the same no matter what persona you are projecting. If you saw the movie "What a Woman Wants" with Mel Gibson where he is in bed with the barista for the 1st time and listening to her thoughts.... If she was just have verbalized them in the 1st place, that would have made all the difference.

Or another way to say it "Kathi is right".

[BRANDYJ]

Like someone else said... If HE is a Crossdresser and not a TS, then you would do exactly what you would do with a man. The clothes don't change the way we respond, or how making love feels, simply because we are dressed and looking fem and feeling fem. The mechanics are the same. The only thing you might consider is to be more gentle and slower in your touches and caresses. What he fees is in his head. He might imagine his equipment is different just as he feels his gender is different when dressed. If he is more of a TS, then I don't know if it's any different from being a CD when it comes to sex. So my advice is to relax and just go with the flow as DeeArel said. The first time making love or having sex with any new partner is always a learning experience as to what they want and like. A CD is no different.

[Cheryl T]

Just do what feels natural and pleasurable and I'm sure no one will complain.
Treat her as a woman in all areas and just think of it as a somewhat larger version of yours.

[Aprilrain]

Hmm? well, My BF is a CDer and he pretty much likes what any guy would like. If anything hes just a bit more passive.

To really get to know what turns your friend on it would help to know your friends gender identity. As others have said a CD is still a dude underneath those breast forms however a male bodied TS has a female gender identity so will likely approach sex from a much more female perspective.

[Veronnie2]

I understand what your going through, but if you approach it with a womans attitude, and just do to her what you like done to you, you will both have a enjoyable experience. Romance, romance, romance. Just go with the flow and do what you both feel comfortable with doing. Veronnie

[Tina B.]

It's simple, if it feels good do it, if it feels icky, don't do it.
Tina B.

[Jessica Keys]

mmmmm Well, I always like to at least keep the bare minimum of lingerie on during the bedroom exploits....like bra, gater belt and nylons as these keep me feeling more fem

[ashleymasters]

I have had some luck with a technique I would love to share but the description is too graphic for the forum. When you are a full member message me and I will be glad to share.

[Aprilrain]

if you approach it with a womans attitude, and just do to her what you like done to you, you will both have a enjoyable experience.

Well if it were me then she'd need to buy a......ah.....prothetic penis

[KandisTX]

You are correct that this is a subject not easily discussed openly in this forum, the answer is the simplest one that has been offered already. ASK QUESTIONS. What is meant by that is that you need to ask your partner how they want you to treat them, what they want you to do to them. If as has been stated they are CD and not TS, odds are they would respond to the way you would treat a male partner who is not a crossdresser. Often times when crossdressed, we desire to be treated as if we were actually the gender we are presenting. Your most important tool to use is your mind and asking questions to provoke the answers you seek from your partner.

[Kate Simmons]

While the genetics and mechanics are obvious, a question I would have to ask myself in this situation would be:"If real love and caring is involved does it really matter that much?"

[KellyJameson]

You have a strong presence so this should be very complementary to your partner because I do not sense any reluctance in you for taking the initiative.

Think of a woman, many become sexually frustrated because they presure themselves to climax and the goal destroys the desire, this also happens to men when their hormones quiet down and they do not feel like pressure cookers ready to explode. Do not approach love making like a job with tasks that must be accomplished. Any thought in your mind that lives in the past or future that holds the words (how,what,where,when or should) throw away.

Enjoy each other with sensitivity, laughter,curiosity and exploration (learn together without fear) with no thought for the destination. If it feels like work something is amiss, stay in the moment.

I live very close to nature so have no knowledge of man made items used for the purpose of sex so cannot be helpful in this fashion.

[JenniferR771]

Sensitive up top? Got any erogenous zones above the belt? Women like it (I think), so pull his bra up and give his chest your full attention. Try not to get too much lipstick on his bra.
Report back.

[MsJanessa]

Many of us, me included, love the feeling of being caressed through silk and/or satin---I know that some like to wear fewer clothes when love making but for me, the more sexy lingerie I have on, the better--just a thought--as suggested above, talk to your partner about this

[StacyPump]

I think, as others have recommended, that communication is the key. I would like to add, that there are some crossdressers (not all, and not most, but some) who, at least while dressed and presenting female, are open to the thought and/or fantasy of performing the physical role of a woman during sex. It is possible, as others have suggested, that a strap-on style prosthetic might provide some fun and interesting opportunities, if you are both open to that, which you won't know....unless you talk about it!

Good luck and have fun!

[suchacutie]

ok...the communication is certainly important, but my input is that communication can only be effective with the needed questions and answers, and those might be hard to identify.

You imply that the femininity aspect of all this is very important. In that case I'd be careful to not peel back too much of the onion unless your partner indicates that is something she wants. The more of the onion you peel away, the farther from femininity (physically, by definition) you proceed. She needs to be aware of this as well and should dress accordingly.

So, to my mind, the communication needs to center around her comfort level about her femininity and where in the "illusion" the femininity loses its supremacy.

Regardless, as it is with all intimate relationships, you both need to be aware of each other and let it go from there!