Crossdress ideas..

I've been straight all my life. But in the past year or so I've been trying on skirts and other items.

I was always afraid of penetration. But I finally decided to try it small. And worked my way up to a large dil** I would suddenly dress in lingerie and a skirt. And go out for a late drive. And find someplace quiet to toy myself. I practiced it many different times and positions..
I finally found out if I rubbed my p spot the right way it can cause a great hands free O.

I've only ever done this alone. And left myself very satisfied. But as of last month I've been getting ideas to try the real thing. With another male.
I would love to tell my wife. But I'm afraid it would ruin us.
Also wondering if it would be worth it to try it with someone for the first time.
I find myself craving it but never acting or showing my desire for it.
P.s. My wife and I have a great s** life. But I have no idea why I decided to try this. And it has made me bi.

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  • Tell us where you live and let’s set up a meeting in a secluded place

  • Most I've done is trade undies with my hot older sister, right off of her body. Started off as a joke or I dare you, then turned into a fun thing between us. I'd wear her thong panties, and she'd wear my boxers. We'd do it spur of the moment, too..At family gathering or kid's events. She'd lean over and say "Change, now", and we'd trade off. I liked it more than she knew.

    Only other thing we'd do is, since we share a thing/fetish for her killer-long nails, if she did them in a color I liked (which was pretty much any), I'd let her do my toes so we matched. Nobody knew that her sexy, long nails and well-polished color was the same as what was underneath my socks and on my toes.

  • LOL ! What do you tell your wife when you don the lingerie or skirt and go prancing out the door for "a late drive " ? Oh, don't mind me, dear, just going to the store for some tampons since I don't like your brand ! Bullshit post by a slowly developing teenager.

  • Lol I don't get dressed up in front of her. I'll do it later at a hotel or something.

  • Don't tell your wife keep it in the closet they don't understand as the urge gets stronger you want it more from experience the only thing I reget is not try it sooner I am 41 now and a closet sissy crossdresser who love cock

  • I know right? It's oddly satisfying once you get past the pain. I find it only hurt a few times when I first started. But now it doesn't at all

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