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

Sports & My Sister's Closet

For starters, wouldn't it be fun to have a pickup game in one of these outfits?  would make the games soooo much more interesting and bring new meaning to the term "contact sport":


I've liked sports all my life.  Both watching and playing.  I remember going to a college basketball game when I was about 12 years old.  This game has a fond place in my heart because it was actually the first time I put on a pair of my sister's pantyhose and panties and went out in public!  OK, so I also put on a pair of pants to hide the fact that I was in heaven!  There was no chance in a million that I was going to let anyone know what I was wearing underneath.  But I remember barely being able to focus on the game, because all I could think about was the thrill of wearing girlie garments underneath my regular outfit.  In essence, I was wearing something like this:

... and it felt sooooooo nice.  I loved it.  I remember putting my hands in between my shoes and feet so I could feel my sister's pantyhose against my skin.  Walking to and from the arena was special, too, since I got to feel the tightness of the undergarments as I took each step... only 12 and I was already naturally drawn to this enjoyment!!!

During those same years I would also get home from school and ditch the schoolbooks and head for my favorite place int he sister's closet to try on her clothes.
 
Besides her beautiful pantyhose and underwear, she had a couple of pairs of high heels that I never saw her wear.  So I took it upon myself to give her shoes some attention.  Although my current preference is for something glittery or strappy, the heels looked something like these and suited me just fine at the time:



The added height, the careful balance needed to walk in them, and the way they made my feet, ankles and legs look was sheer delight!  When I think about it, it's quite amazing that I was compelled to dress up.  I didn't have the internet or other large forms of affirmation to urge me, or to indicate that there were others out there with the same desires as mine.

I do remember as the years went by and my feet would grow, that the heels began to get tighter and tighter.  Although the restrictive feel provided a certain sensation, I remember being happy that I basically had stolen my sisters pantyhose by then and needed to wear them in order to fit into her heels.  Walking around my bedroom at home with those shoes and hose on was bliss.  No wonder my grades suffered!  :)

I'm not so sure if legging like this existed back then, but if they did I would have enjoyed getting dressed up like this:


Well, it's the summertime so I'll try to start the season off with some color!  I'll take the red shoes with the neon blue stockings!  How about you?


Best,
Jess

p.s. I just think these are hot action shots and wanted to share

Women's Catalogues vs Playboy

A fellow crossdresser recently pointed out that she, as a youth, often preferred looking through women's clothing catalogues rather than Playboy/Penthouse and the like.  That got me thinking that i felt the same way growing up!  There were only so many photo's of boobs and crotches to keep me interested, but the clothing has NEVER gotten old!  I then also realized that I was fantasizing about the clothing and lingerie more than I was about being with the girls in the photos.  Give me a photo of a girl in a nice outfit any day over a girl naked on the bed showing me her privates.  Perhaps that is a telltale sign to how we feel as crossdressers... i'm just not sure.  But it was a nice revelation to have.

So in honor of this illumination, I bring you some photo's that would have turned me on as a youth, and still turn me on today!  And like many of you, i'm supposing that we are more interested in the outfits more than anything else.  agree?

Enjoy (i certainly am)...

Jimmy Choo, thank you:

I'd even pleasure myself just looking at beautiful shoes like the one's above and below!  The arches, the pointy tipped heels, the straps that lock you in, the pretty jewels.  This is all I needed to look at and blow my load.  Who wouldn't love to try on each and everyone of these shoes?  Great reading material, yes?

 

BCBG, steal my heart!  If this catalogue existed in my teen's I'm not so sure I would have ever left the house or made any friends:


I'm quickly warming up to the idea of some beautiful boots:

I'm not picky... these slippers and this whole outfit say YES too:


Feeling that urge by now?  I am...  I'm going to go grab some women's catalogues as soon as I can and ENJOY myself!  Forget the Playboys and the Penthouses... give me a Jimmy Choo catalogue (for free!)

Best,
Jess

Sofia! Sofia! What are you doing to me?!

I recently saw this an have a new crush:


Simply put, Sofia is a hottie.  She does everything for me, just like a typical man.  With that said, i also found myself wanting to LOOK like her, and especially to try on her gorgeous swimsuit.  Her beauty, AND the beauty of her choice in clothes makes me warm and tingly all over.  So in honor of Sofia and anyone else feeling similarly to how i feel...

I'd actually like to wear this teddy under the ensemble.  I could live in that outfit for a long time and be happy:



Yep, would like to take her out on a date looking like this:


In the end, the above photo is actually what I'd like to wear the most.  A mini-skirt with those leggings, along with a simple camisole/tank and fitted jacket looks great here.  Heck, I'll even paint my nails to complete the look!

Cheers to Sofia!

Best,
Jess

Thinking in Pictures

Oye!  I'm intrigued by everything going on here.


Now what do i do with myself?

I've never had anal sex (giving or receiving).  Wondering what's the appeal and what it's like.  Seems so verboten but something i'm missing out on at the same time.  Can anyone chime in here?  In so many of the video's and photo's i've seen, it seems like the person being penetrated is flaccid.  Does that mean it's not enjoyable, physically?  I would think I would be hard if I were into that type of thing.  Kinda like I am hard right now thinking about it.

But i'm still in the camp that women are beautiful and i'm attracted to everything about them.  Still sorting things out.

More exploration to come... :)

- Jess

Enjoying some alone time once again!

I put on some tights today along with a beautiful set of glitter heels.  These photo's don't do the outfit justice due to the lighting, but i really liked the look of the tights and the shape of the heels.  I really like this first photo because it elongates my legs.

The undies were lacey thongs that rode up me very intoxicatingly.  The tights held my undies and privates in place very well.  Atop everything was a Mossimo sheer top with beading which swayed nicely.

 Ooppss!  I forgot to wear something on my underside, so i hope you don't mind the extra visuals.  :)

Tonight I don't think things are going to get too messy, but I still plan to sleep in as much of my garments as possible, minus the heels.

 

In recent times, I've found myself wondering what I could be wearing while at work or running errands.  If only i could do so... I think it would be really fun and nice to do.  But I don't see that happening in my lifetime.  Dare to dream:

I've still been thinking about how I can enjoy myself with somebody else.  I'm so aroused by women, that anything short of being with somebody feminine doesn't work for me.  I'm just not turned onto men.

But me dressed as a woman also creates a perverse desire to do womanly things, like interact with the male organ. I still think about this, and would not resist the opportunity one bit if it presented itself. What is that opportunity?  It's probably to be with another crossdresser or transexual.  I have dark hair like the woman in the image above.  I want to make out with the blonde in the photo but wish she had a penis so I can then experience intimacy as a woman.  Is there any other way to do it?  Do I have the courage to meet up with somebody to play out my desires and curiosities?

 

Uh, oh... things might get messy afterall!

Best,

Jess

 

 

Feminine Exposure

I've been receiving some really nice comments from viewers in recent times and i've gotta say, it's a new experience to hear from other boys on my looks.  As a man, it's not often that you hear somebody telling you how sexy you look, or that you have nice legs, or that the outfit you're wearing is nice and asking me where i bought it.  It's really nice and i've enjoyed talking back/forth with my viewers.

I'm really itching to get back into some heels and dresses but haven't been able to find the alone time needed to do so.  I'm looking forward to the swaying of a soft dress and feel of stockings, panties and heels encompassing my body from hip to toe.  Aroused just thinking about it.


I wouldn't mind going to bed (or waking up) in the outfits below.  i would just hope things didn't get "messy" early on:
 


Which brings me back to my earlier point whether or not I want to experience all things feminine, which includes the clothing, etc, but also the intimacy which involves being with a man.  As stated before, i'm not attracted to men, but I am finding myself curious to experience intimacy as a woman which involves somebody else's penis.

WHAT DO I THINK ABOUT THE IDEA OF GIVING HEAD, OR BEING PENETRATED MUCH LIKE A WOMAN?

DO I RELEASE MY USUAL ROLE AND  PLAY THE PART OF THE WOMAN (WHATEVER THAT MEANS)? 

I will be thinking about this more and keep you posted!  Still have no idea where this journey will take me.  In the meantime, I've got to keep my hands occupied with something else!  :)

- Jess