Cross Dressing Fantasies

I have mentioned one of the fantasies before in other threads, but I thought it was time to actually start a separate thread. Many may think it's a little odd, but I don't care.

I am very submissive, and nothing would please me more than to find a long-term domme, a mistress who will control me and make me hers totally. I also consider myself to be a sissy boy, since I love wearing panties, stockings/pantyhose, and lingerie, and I would want a mistress that enjoys dressing her sub up. But, considering my location and other circumstances, that may never happen.

So, since finding a permanent mistress seems unlikely, there are many specific fantasies that I would like to fulfill. A couple of them specifically involve being a sissy sub.

Now, while I love wearing panties, stockings, lingerie, etc., I have never really had much desire to totally cross-dress. Wearing bras seems pointless since I don't have boobs, and wearing dresses or skirts and blouses doesn't really appeal to me either (I do like wearing heels with my stockings though). Neither does wearing makeup and a wig (especially since I have a goatee.) Except for a couple of specific fantasies.

One fantasy is that my mistress dresses me up in a French maid outfit. I then spend the rest of the day serving her and pampering her. I give her a bath, massage, cook for her, serve drinks, etc. She sometimes feels me up as I walk by, reaching under my skirt. She makes me get on my knees to lick her. If I do something wrong, she puts me across her lap and spanks me. And if I do well, she eventually takes me to bed, sitting on my face before bending me over for her strapon.

But my other fantasy is my favorite. Again, she totally dresses me up, wig, makeup, everything. I even shave my goatee for this one time. She has me wear a short skirt and stockings, maybe even a schoolgirl outfit. She turns me into a woman, and treats me just as if I was a lesbian (or maybe a straight woman who is feeling certain yearnings.) She seduces me as a woman, kissing my neck, running her hands all over me, etc. Then she makes love to me, pretending my ass is a pussy. But, while it is somewhat romantic, she also dominates me just like she would a lesbian lover. She makes it clear that I am her slave, making me worship her. Maybe she restrains me and sits on my face. Or anything else she would want from a woman.

So, how many women on here enjoy sissy boys, and would like these types of fantasies? Or other fantasies that involve men wearing panties, stockings, etc.? Does anyone have similar fantasies?

There's nothing "odd" about your fantasies. A lot of guys like to cross-dress and there are certainly no shortage of "Doms" out there for you. Good Luck on your search.

You have a awesome Fantasy. It's very doable with the right person. I'm sure many providers have contacted you and are MORE THAN WILLING TO OBLIGE. Screening them is what you should be doing what you are asking takes trust. It is more than client/provider relationship I believe. Don't get taken advantage of Hun. Being a submissive doesn't mean you're stupid by any means. Be safe. It would make me proud to have you as my sissy boiPussy. Good luck

I played out a fantasy extremely similar to this with Yummy Marie a few years ago. She was absolutely incredible. She made the whole experience very real.

More recently I've done something like this with Stella Dearborn, also exceptional, and she has a toy closet overflowing with kinky delights.

So much fun--especially when we are both in silky lingerie and stocking and sensuously rub our bodies against each other and intertwine ourselves. Yum. . . . .

And this is why I carry a whole suitcase full of Outfits 👙, nylons, 3 pair of shoes 👠 and a couple of wigs, bows, lipsticks 💄

See, there's nothing strange about your fantasy! You are bold to admit your true desires most subs won't do it... At least in front of their none fem male counterparts. Any mistress could be really happy to have you and dress you up... Etc.. Most will actually tour with outfits and wigs etc just to have that chance. It's a very fun fantasy hopefully you find a Domme that will mold you into her sissy bitch.

Get dressed by a hot provider in a strange city and then she makes you pay the rent down to BBC road and your stuffed airtight till your ass is so sore you tap out with your safe word .

Tall house cracker !!!

I'm a cracker so what !

I have played with guys who are crossdressers...I luv kinky boys!
{I really love when a gent wears sexy pink panties under his jeans...but thats a different fantasy..lol}

I had a gent in oregon who was a big ig and well known in town..he would come over to play...and I would put his makeup on and then help him dress..then we would go have a drink at the hotel bar! He actually knew the bartender once,but the bartender did not recognize him {lol}...So much fun!!