The Crossdresser’s Guide To Masturbation

You’re a crossdresser but how do you masturbate? This crossdresser’s guide to masturbation will give you a few tips. Panties feel amazing against your cock, don’t they? You love that silky cool smoothness pressing against you and can’t wait to really start masturbating all dressed up. You just started really putting on clothes, and while it seemed very exciting at first, there were some logistical aspects you didn’t really think about, weren’t there?

Nothing that can’t be overcome, especially with an experienced assistant guiding you. That’s what I’m going to do a little bit of here. Give you some Masturbation options for when you are all dressed up and feeling sexy.

First of all, lets get past the fact that you already know how to masturbate and have been doing it for years. If you really believed that you wouldn’t be here reading a guide to masturbating as a cross dressed man. You would be happily stroking along and thinking of nothing but that amazing orgasm you’re about to have.

That’s not what happened when you got dressed up, though, is it? You realize, that while not impossible, you wonder just how and where to start. Normally, you  just pull down those man jeans and your very ugly men’s underwear. Yes, by the way, even those silky boxers only look really good on women. And you grab your cock and go to it. Well, when you wear a dress and stockings and silky soft panties, you can’t do it that way. It requires a little more finesse.

Crossdresser’s Guide: I Have To Keep My Clothes On

So lets assume you just adore the feel of those clothes.  And taking them off kills the incredible hard-on you have. Still, you have to do something to get all the way off. Well, you are about to find out just why you sometimes see women sitting with their legs crossed and moving them just enough to cause a gentle rubbing.

It may look a bit like a praying mantis until you are used to the movement, but you will love the friction caused by nylons when you cross your legs and rub just slightly. With your cock and balls covered in the silky panties, this is a subtle way to start masturbating without needing to use your hands at all. Alternatively,  use your hands to rub your nipples into the soft padding of the bra you are wearing. That’s what we do, after all!

I Need To Toucha Toucha Toucha My Cock

Now, maybe you want to use your hands. You are a man, after all, and we know how you love to feel that hard cock. Well, there are many, many ways to go about this. You can choose whichever works best for you.  But since we don’t want you to have to undress, the best way is the naughty slut way.

You know what I mean.  Lay down and lift up that skirt! Put your hands under that skirt and start rubbing, first your thighs.  And then, if you’re wearing pantyhose, roll them down to just under your panty-encased ass. If you are wearing stockings with garters, that’s a step you can skip.  I want you to be able to get to those panties.

This is where you are going to want to just go crazy and pull things off and stroke wildly. However, that will, in the end, feel like you did it wrong.  And you’ll be disappointed in yourself.  So, pay attention. I’m going to help you slow down and enjoy it, since I know that is what you really want. You want to enjoy every sensation.

Amazing, Isn’t It?

That’s the point of the silky panties, after all.  For you to enjoy the luxurious feeling of your cock being rubbed smooth and soft by the silk or satin and then many even pricked a little by the edging lace. Take your hand now and run your fingers around the edges of the panties, teasing yourself a little, before sliding them over and letting your hand rest on top of your cock in those panties.

Press the smooth cool fabric against your skin and start just slowly rubbing your whole hand up and down, not stroking, since you aren’t grabbing your cock. Just rubbing like you would if you were a woman, right through those panties. Amazing, isn’t it?

Crossdresser’s Guide: Stroking Is What Really Gets Me Off

Finally, for those of you who just have to grab the cock and stroke it. You can still be a stroker and all dressed up, just take off as little as possible. Ideally, the panties will be the only thing that needs to come off. In fact, I highly recommend to you, if you know you need to feel your cock in your hand to really cum, that you choose a garter belt and stockings over the pantyhose, so you can leave them on, along with everything else.

This can be highly exciting, to sit on the edge of your bed, or lay back and flip up that skirt, panties off, and stroke your cock. Just remember that unlike your boy clothes, cum can ruin silk stockings. So, have something to catch it with, so you don’t have a stain on your dress. Those are tacky.

While there are many variations, these are a few of the basic ways to masturbate while cross dressed, without having to give up the excitement of having on the clothing you love.  And the good feelings that go along with it.

Feel free to experiment with positions and outfits and even encourage your partner to help you out. Or ask your Mistress.  She will happily guide you in  all kinds of interesting, sexy masturbation techniques that will still allow you to stay dressed and sexy and feminine.

Enjoy this crossdresser’s guide to masturbation? Give one of our feminization Mistresses a call, today!