Wednesday, October 31, 2012

A sissy's perspective on endurance in black & white


A photo shoot from 1980 that still has a BIG effect on a 2012 sissy. i thought Cynthia was pretty smoking back then. She never made eye contact, She doesn't have big tits, She isn't necessarily a world class beauty. It doesn't, She has an enduring quality in this sissy's world. She possesses endurance.

It doesn't matter to me that She posed for this shoot 32 years ago. What matters (to me) is the profound effect that She still has on me. What She represents is a glimpse into my long term interest in Femdom. i am now ready to admit what i was totally in denial about it all in 1980.

Back then, (i admit now) i was looking at the cock at least as much as i was looking at Her - if not more! i simply didn't want to admit it to myself. She was getting him very, hard! And what a timelessly beautiful hard on he had! Yes, i thought i was masturbating because of Her - and the fact that Her 'subject' was so aroused about being dressed. Now, i realize his big boner is also a timeless beauty. Now i admit that i love and appreciate the tapered shape of that cock. It seems that the head and top part of the shaft  is slightly smaller than the meat of that considerable cock.

Made for entry into another sissy's moth or sissy pussy.! Talk about endurance........
If Cynthia demanded that i sucked him off, i would (now) eagerly comp\y. Or bend over.....

And once again today, there's the ever present Monica - well for about 3.2 years!. Lately, She has endurance & presence as well.  Like Mistress Cassie, She is a prominent Figure in the 'picture game'. i lost to Monica tonight and the mandatory post was the 'Cynthia' caps, a Monica cap ..

And - two Mistress Cassie caps:

Once again, with Mistress Cassie - there is no winning. Except for Her. She always wins! Oh, my..........

sissy maid diane

Tuesday, October 30, 2012

A sissy hubby cuckold - caption series

Her panty and bra set is so, so beautiful. And so is She. Even if being Her sissy hubby can be difficult at times.......

sissy maid diane 

She 'had' panties on - caption

I'm riding out hurricane Sandy. Speaking of riding.....

sissy maid diane

Monday, October 29, 2012

i never get tired of Monica.

sissy maid diane

Dressing for a tranny - caption

Whether dressing for a Mistress, a man or in this case - a tranny:

A submissive sissy must always be prepared to do what's needed.

sissy maid diane

Sunday, October 28, 2012

Past, present, future femming

THE PAST - fantasizing & getting excited about pics like this.......vulnerable to femming. Suppressing the woman within.
Masturbating in secret spots with secret lingerie.

PRESENT - A trained, feminized sissy. A little off on  my feminine sissy hygiene, i need a shave paint my nails & shoot a blog post.

FUTURE - It may be a few days as the hurricane approaches. Certainly by the end of next weekend -i'll be poofed, painted, shaved. Posting in full sissy mode. Getting ready to resume my advanced sissy training - ready for Mistress.

sissy maid diane 

Saturday, October 27, 2012

Teased, tormented, transformed (by a tranny)- Part 2

Here's some pics from the other issue of Teased Tormented & Transformed. This one features a lovely tranny - Shannon. Of course, the poor cross dresser didn't know that She was being feminized by a tranny - until it was too late.  i just love the accompanying text. Yes, shocking!

So many years ago. i didn't realize back then what i had in store for me. Again, the color pics are the ones i remember masturbating to the most, especially the first one.
 Yes, so many years ago i was fantasizing about such things. Masturbating away, using my secret stash of panties and slips. Long before my own femming. i have a lot more lingerie now. Naturally i  masturbated again after this joyous reunion. A violent orgasm for sure. Yes, it was much, much different this time around.

This time i caged.

Oh, my!

sissy maid diane

Teased, tormented, transformed - facing the past

Here's an unexpected development. Today i spent an inordinate amount of time surfing for a long lost - but well remembered lingerie ad from my adolescence. The Internet is amazing, but i failed to come across that influential image. But i did happen to find something else that was very influential. Years ago.(before Mistress) i crossdressed in private and fantasized then masturbated to porn. Way before the Internet it was magazines. Overall - Club magazine was probably my fav.

From time to time i would purchase a Femdom mag, from an adult book store. i.distinctly remember two magazines in particular & here's a couple of pics from one of them. Teased Tormented & Transformed. What a great name for a magazine. There were a lot of pages that i purchased - digital copies. 

Most were actually in black & white.But these color pics are the two images that i remember the most.The Red Head is Cynthia. A couple of years later, i married a red head. Hmmmm.....  Very influential. i remember frequently masturbating to these images almost 30 years ago. Back then my femming was fantasy. 

Now, it's real - and anything but private.

Next up - a few images from another vintage copy of Teased Tormented & Transformed.

sissy maid diane

Thursday, October 25, 2012

Funnel of love

Yes, i know - it's been entirely too long between posts. i'm still struggling with the trials & tribulations of life. This is an upbeat blog, so i won't get into the details.

There's something else i'm struggling with besides life issues. That of course is my undeniable need for femming. While i have been doing very little dressing of late, i do find myself surfing the net and i'm back to playing the picture game.

The picture above is one of my latest faves. The Woman holding the funnel is Katie, the One i'd like to trade places with is Jacky. i've even found myself looking for yellow funnels and theta gag.

Here's another view of these Two - wonderful!

And this:

Then, there's the tries and true. From posts past, here's Monica and Her friend Sonja.

 Monica still has that certain feminizing effect on me. Her legs are perfect! i have other images of these Two. They really are Bad Girls.

Sonja at the bar, one hand on a cigarette, one hand on a bottle of liquor. And the seductive Monica in the forefront. Yes,. They are a bad influence for sure. That is unless you are a fan of feminization.

So, what else? Oh yes - this one has been of interest to me lately:

It seems that my sissy hygiene has slipped of late. i have on a girdle and stockings right now - i'm feeling so inspired! But i know i'm not experiencing 100% of the silky feel of nylons on freshly shaved legs.

Not yet anyway.

sissy maid diane