The "Dude Looks Like Lady" Session#5

[Thegustaffa]

Hum the tune "Dude, Looks Like A Lady" by Aerosmith when you read this thread, somehow it fits!

I remember this session, because believe it or not, as common as cross-dressing, I had never encountered it in any of my previous sessions. I
remember giggling uncontrolably for the first couple of minutes as the sight
before my eyes was not only quite "cute" for a man, but the outfit worn
appeared to be something that was his "usual" outfit to be worn and he
seemed to have placed quite a bit of thought into it. When I opened the
door to my session, this was the sight that awaited me.

My client, seated in a chair, was dressed in full up and down lingerie.
Light purple in colour, was a bra, (32A?) that still left enough room for a
small family of cats, light purple panties (full botton), light purple garters
attached to light purple stockings, light pink ballerina slippers, and one
plastic dark purple bracelet hanging from his wrist. I thought I detected some
blush, but it may have been naturally occuring considering my giggles.
The giggles also came in part due to his demeanor when I entered the room
which was something like "a greeting an old girlfriend that you haven't seen
in a long time would give you, with whom you were once best friends".

Client: Smiling, eyes lit up, extremely cheerful "Hey you!!!!!"
Red: "Hi.....you....too" giggle, giggle, looks around room for stiletto's & purse
Client: "How do you like this?" Proceeds to turn 360 degrees around, pausing on the ass view, twirls around to front,(with Esso pipline creeping out of purple panties)giggles and waits expectantly for my response.
Red: Red cannot respond now due to bent over laughing, side splitting
giggles
Client: "I know, I know, it's g-o-r-e-g-o-u-s on me, but do you think it makes me look fat?"
Client is now staring and posing in mirror, pinching fat, pushing up breasts and fixing hair

Taking a closer look at my client, is even more hilarious as this man is the
COMPLETE opposite of what a woman looks like in lingerie and it is very
startling to actually see it. Dark long coarse hair is sticking out of every
possible opening of this outfit, even through the stockings. The inner thighs
also had pubic hair creeping out of the panties.
Even the back hair springs out in different spots around the back of the bra. The ballerina slippers looked so wrong too because they must have been a size 10 or 11 as opposed to the petite sizes most women wear. Even the sight of a feminine bracelet on a man's wrist looks akwardly placed. I suppose the lingerie might have looked more akward if he had been a very
large or obese man, however this was not the case.

I instructed the client to start the massage by lying down on the bed and
I already knew the lingerie was going to remain on. I wanted to polietly
express to the client that it was going to be a massage and not a half an
hour of some type of role playing. He agreed to the massage stating that
he was sore from dance class and couldn't wait to relax.

I did not object to the small talk about his "female complex" and I was
really interested to hear how he envisioned himself as a woman. But you
could tell that most of his "female complex" was the general knowledge
that some men have/think of a woman's life. Some men, not all, some.
"I have 3 men dying to go out with me"
"My nails keep breaking, what's the best way to fix them"
"What colour should I dye my hair?"
"I've been so emotional, I guess it's my time of the month"
"I love shopping at Guess, and lately, The Bay"

The session finished a little odd, with some "squeeze my big tits" requests
from him and some dirty talk that a woman would usually utter in her
moment of glory. Other than that, it was certainly a different and amusing
session for me and I left him to shower.

When I returned to the room, the "female complex" was gone, and a totally
normal business man, deep voice and manly attitude, was what remained.
I would not have known it could be the same person.

It looked like only the shoes and bra were in a small plastic bag when he
left, so I assume he still was wearing the other lingerie under his business
clothes.
Which U.S. president carried these similar traits? Was it J. Edgar Hoover?

 

[red_writer]

I'm pretty sure it was Emilio Estevez, but don't quote me on that.

Did he have a world class package?

 

[Fergy]

I think Hoover was the head of the FBI not president but I'm no expert on US history.

 

[dantheman]

Seems like an interesting fetish, that he got off by dressing and acting a certain way, that's opposite to how he normally is.

I do enjoy switching stereotypical female/male roles..... e.g. instead of controlling the flow of a session, lying back and placing yourself in the hands of the MPA. This is particularly good with someone you've seen a few times and she knows what you like, so you don't have to say anything and the conversation can be about other things.

 

[Lov3]

Oh my god. I had to stop three times during this story because I had to stand up and breathe. I haven't laughed this hard in eons. Thank you, thank you, thank you.

 

[me!]

One of lively discussion long ago with ex-GF's gay friends, over a bowl of Cafe Au lait as they experimented with cross-dress while search for sexual identity. "The sensual feel of satin..." One remarked tough to find size 14 heels and lingerie for 6'8". But this was before the popularity of internet
http://www.clcrv.com/crossdressing/whycrossdress.cfm

Perhaps RS should recruit him (her) to be MPA as others may seek such service? 32A, size 10/11, squeeze breast & dirty talk..

Frankcastle your U.S. history is correct, Hoover 1st FBI director. I believe Biography channel mentioned Eleanor Roosevelt was. A book with her quotes
http://www.laceyleigh.com/7Secrets.html.

 

[cruz1850]

I'm sure the 'Woman, Looks Like A Man' episode is next

 

[Jennifer W]

It's "Man I fell like (having) a Woman"

 

[72 mg]

No package in the world has more class than yours Rust!!!

 

[Intern Jessica]

Thanks a lot, Stils

And might I say that no box in the world has more class than yours.

Word is John Stamos.