My venture into crossdressing.

I dont know where I really fit into all of this. I love being dressed up, but as of yet, I have not actually worn female clothes, etc., other than what you will see in my photos.  My wife has made a fantasy of mine a complete reality and she loves the idea that she can play with the idea of bisexuality without actually doing it with another women. She gets the best of both worlds when I am dressed up and we make love.  She and I both have fetishes for breathplay (plastic, underwater,) and smoking long 120mm cigarettes (or longer) in cigarette holders.  I am just a year into this really so I dont know where I intend to go with it, but for now, I just need to purchase some more pvc clothing as I do not think I will ever look great in womens clothes.  I am just too big in body structure. When I wear my boots, I am 6'6" tall. 

Anyway, I am glad I found this site again and have more than just my breathplay artwork to share now.


JenniferCori

[Like Ra]

Hang on... Are you wearing a mask? If yes, it blends amazingly perfectly. If not... How did you achieve that look?

Good question. I have seen masks before, but I don’t think it’s a mask.
But I love the makeup. As for clothing, they do make plus size clothing that really looks good. For me, knee length skirts and matching vest works well for me. PVC.... not so much. Maybe that’s why I haven’t bought any latex gear.

There is only one image with a mask and that Is a masquerade mask. The rest are my face with make up done by my wife. Admitted there are three of them that have put through a glamour shot type filter
My wife did a really great job.

And you did a lot of this in a motel room?
Very brave and very good as well.
WOW

[Like Ra]

The rest are my face with make up done by my wife.

Whoa, amazing!

a glamour shot type filter

Still fantastic.

Maybe I have a chance 😋

The rest are my face with make up done by my wife.

Whoa, amazing!

a glamour shot type filter

Still fantastic.

Maybe I have a chance 😋

I didnt think I had a chance when I first started into this. I had for many years worn a mustache and a goatee and I decided to go at it slowly, shaving the goatee off first and I didnt look right with just a mustache so I went the rest of the way.  I keep my face shaven most of the time now as I would never attempt to dress up with facial hair showing through. Thats just not right in my opinion.

And you did a lot of this in a motel room?
Very brave and very good as well.
WOW

Yes, we found a motel that had one or two rooms that allowed smoking so we went there and had a great time doing photos and playing around.  My full intention was to be brave enough to walk from the hotel room dressed like Jennifer and walk to the end of the hall where the indoor pool was at and I planned to get some underwater photos as well but apparently there was a softball tournament in town that night and there wasnt anything but a bunch of teenage girls in the pool so I decided against it.

My younger brother passed away in February of 17 and it was at this point I realized I needed to come clean with myself and take a chance on fulfilling a notion that had been a part of me for a huge part of my life. I began smoking long cigarettes meant for a woman when I was 12. I never put 2 +2 together except a couple of times in my life and I thought it was ridiculous those few times so I just never went further with it. After my brother passed and knowing I had quadruple bypass surgery 5 years earlier and realized I am living on borrowed time (I think we all are in the end), I decided to make Jennifer happen.

I was sitting around one morning by myself and started sketching out a "vision" of JenniferCori and once I was satisfied with the idea (you can see the drawing had no face which was important to my idea once I finally explained all of this to my wife because she saw the drawing, didnt think anything about it and later she understood).

I started looking around on the internet for things to make this drawing come to life. I still have the full drawing somewhere but need to find it and will repost the image here later.  I started finding the items that would bring JenniferCori to life and had to wait about 2 months entirely before everything came together. It was almost another 2 weeks before I told my wife.  Its weird how it happened because we were going to do a photoshoot of her "dressed up like her vampiress" in one of her books and she said...."I wish I had some really sexy boots to wear during the shoot".   I told her I had some in the trunk of the car.   She looked at me surprised and thought they were a surprise meant for her.....but I told her "Yes, but they belong to me".   It was easier in the end to tell her than I thought i thought it would be and this was the first time she had any inkling that I may be fond of doing something like "dressing up".  

She was always a huge fan of the Rupaul drag shows on TV and things like that so I think she really started seeing the canvas that she had to work with and later that evening, she made it happen.  Ive got an awesome wife.

Here are some of the things that brought JenniferCori to life and I carefully selected everything that I thought would fulfill the idea. I do wish I had started this younger, in my teens.

[Like Ra]

My wife was shopping today online, then suddenly asked me:
"Do you want a silver mini-skirt?".
I replied with:
"Sure! Always! But I've aeady got a couple of shiny sequined skirts. They damage pantyhose. And I finally need to wear them..."
"Yes, just wear them".

And that was it for that moment. Later today I realised that she indeed ordered that mini-skirt for me 😁 Eagerly awaiting the delivery now 😋