Fantasy and Reality

I've started this journey squarely as a crossdresser who likes to dress up on beautiful outfits.  I've enjoyed how I feel when dressed up, and frankly love how the outfits feel on me while wearing them... smooth, silky, DELICATE, sexy, and delicious.  I was a happy camper at that point.  A married man dressing up as a woman.


But then, I went social media with my journey and have be exposed to so many new and different thoughts and opinions on the whole gender play thing and must say I can't stop thinking about immersing myself into the ways and means of a woman.  Certainly sexually speaking for now, but who knows?  So now i'm consumed, yes consumed, with the thought of sex as a woman.  For me, that entails giving blowjobs, and being penetrated by a man.  i'm vulnerable... i'm ready... i'm aroused just typing this out right now.

Not that I care what that makes me in terms of hetero, homo, etc, but I frankly don't know what I am except for being a man, loving to wear woman's clothes, and willing to explore the fantasy of being a woman sexually.  So it would seem as though my fantasies of dressing up and being like a woman are becoming more of a reality to me.  I can't wait!

I've tried to capture some cartoon/fantasy images that appeal to me and the reasons they do...

At this point, this pretty much sums up the clarity and confusion I have about sexuality.  I'm happy with the thought of being EITHER person here: the beautiful redhead that is doing the penetrating and man-handling, or the young boy who has submitted himself to being penetrated.  they both seem to be happy and i'd like to know how it feels both ways.  I think I'd be dripping all over, too.


Take your pick... I don't care who is who here, but I like it all.  Short skirts and penis' everywhere is a good starting point to a great fantasy.  Oh, and my thirst for a man's cum has become intriguing to me.  Wouldn't mind trying... crazy?  I think not.


The girl penetrating is clearly having a good time... I can see why.  but frankly the submissive she-devil is the person I want to be here.  not only is she gorgeously sexy, but she's having so much fun her eyes seem to be rolling to the back of her head!  what a sexual experience!!! i'm jealous.





So I dress up alone while in a hotel room frequently.  I've thought about inviting somebody over to explore my... curiosities... I imagine this is what i'd expect to happen if I carried out this to a reality:


Don't know what to say about this except that if I were "trapped" in this situation my boner would be just about as hard as hers.  Maybe i'd pretend to fight it for a little bit, but then ultimately just give in and submit to the helplessness:


Yep, this would be my facebook photo of me.  Cute, sexy, powerful, confident, and ready to penetrate!  Oh, and I suppose the boobs would be nice on a skimpy outfit like that as well:


Back to reality, I think the next step for me will be to buy a dildo, get dressed up, and see where that takes me.  I still don't understand why most of the images I see of men being penetrated shows their penis flaccid.  From what I know about myself, if i'm penetrated, my penis is going to be straight as and arrow and hard as a rock!  just like all the images I've shared today.


Love to you all!
xoxo,
Jess