Monday, June 6, 2016

Another night out

I went out for another night at a club and this time there were some opportunities to learn a bit more about myself.
It started off when I was getting ready.  I was trying to decide between a couple of dresses, so I posted to facebook:

I started to work on my make up and got a message from this guy who wanted to hook up. I said that I would be happy to meet him at the club, but he was not interested in that and want to come right over and get my into bed.  I was flattered.  I even shared some pictures with him and got his opinion of the dresses.  He liked the black and white one best, so that is what I went with.  Which was a good thing, because my FB friends didn't respond until I was already at the club.  Still everyone agreed that they like the black and white one better.
This guy just didn't want to meet at the club, her just wanted to meet in bed.  I was not up for hopping into bed with a guy I had never actually met in person.  I told him that and never heard or saw him.  so I went back to getting ready.
In getting ready I learned some more about the struggles of doing make-up that I hadn't experienced before.  It is now summer time and the humidity was pretty high.  The extra sweat did not make it very easy for make up to set.  Now I understand and appreciate what my wife went though getting ready to go out when we were in Rome.  The humidity does make it harder.  I was able to find some powder to help thing set and stay in place.
I also did not have any high lighter or blush for my cheeks, so I just took a dry brush and swept of some of the foundation to let my natural color shine through.  I actually worked out to bring some color to my cheeks and a fairly subtle way. 
I was not able to shave my legs this time, so I went with some opaque tights.  These are great they cover the leg hair very well and nothing really shows through.  The other thing great about them is that they have a nice smooth feel.  Sure you don't get to experience that feeling on your legs, but when a hand runs over them it will feel nice and smooth to the hand.  I will have to admit they are a little warm to wear in the summer months, but a gurls gotta do what a gurls gotta do.  Honestly my legs were not too bad from the heat.  I was however quite hot from having a wig on my head.  
I was ready to go and the rain was holding off.  It was a nice drive over until I was about two blocks from the club, then the skies just opened up.  I pulled into the parking lot and waited it out for a little bit.  The rain let up and I thought I would make a run for it.  Well here was my next lesson.  The parking lot was gravel and I was wearing heels.  Neither which made running at all possible.  Luckily the rain was light and the walk was not far.  Still I was a bit flustered by the time I got in the door.  I stumbled a bit trying to pull out my ID.
Got in there and went straight to the bar.  Once I had my drink I met with my friend from my fist time who was right there and chatting with some girls.  They were so happy to be hanging with cross dressers that we got a picture together.  
We got settled into our table with a nice view of the floor that was great for people watching.  I began chatting with this guy my friend knew and he asked my about my sexual orientation. Now I have had fantasies of this opportunity to hook up with another guy and here it was, but I didn't take it.  My true self came out and said, "I'm straight"  Sure, I could have told him I was curious or anything, but I didn't.  I realized that was not what I really want.  I just want to go out and have some fun.  Spend some time out as a girl and hang out with other girls.  I had fun that night. Get out dancing.  Got compliments on my looks and jewelry.  I was even told I look like a 20 year old.  
So my new firsts for this night were dancing in heels and using the women's rest room.  Dancing in heels was a bit of a challenge and certainly more stress on the ankles.  I got used to it and figures out how to do it without killing myself, although there were a couple of moments where I felt like I might twist my ankles. The rest room was just fine.  Really it is no big deal and I certainly felt safer going in there, than I would have going into a men's room dressed as a woman.
My conclusion from my experience is that I want to be one of those girls who hangs out with a group of girls and not be that one girl in the group of guys getting all the attention.  For an introvert like myself this is a real challenge, but now I have stepped out and found a piece of myself, so it is a start on which to grow.

Friday, April 15, 2016

The Games We Played At School

My journey into becoming a cross dresser dates back to elementary school.  I remember being out on the play ground and the boys on the playground were always mean to me.  We played this game called boys vs. girls, where the girls would try to catch the boys.  I would always let the girls catch me.  They told me they had this machine that would turn me into a girl.  Oh, how I wished this machine were real and that I could become one of the girls.  They were so much nicer to play with.  It became a fantasy of mine from then on to be captured by the girls and subject to their transformation of me into one of them. 

Thursday, April 7, 2016

Reflections on this Journey

After chatting with a friend I realized that my growth into a woman is  like going through another puberty.  It really starts off with a lot of sexual curiosity and develops from there.  Initially the desire is often driven sexually and I develop these fantasies of being a pathetic sissy slut and wanting to be controlled by a woman who will turn me into a gurl.  It is this sissy training that helps to bring me out further than just a fantasy and seeking out ways to be more feminine with that hope of being able to attract a "real man" and experience that sexual experience of sucking cock or even having full intercourse. 

For me the reality is that this is just fantasy as it was when I went through male puberty.  Morally i cannot bring myself to have multiple lovers and want to maintain that dedication to my wife.  That actual male persona is real and i cannot deny it is who i am.

At one point i actually matured beyond that point of sexual exploration and moved forward into discovering my full feminine self.  I had a need to post a picture of my face and although I had experimented a little with make-up I was nowhere near ready to post a picture of my face.  This drove me to seek out a professional to help with a make-over.  I searched around and found I really wanted to look like a woman and not just be a man in make-up.  In my search I even spoke with a woman who did forced feminization and although she does make-up with her clients, she suggested I would find it better with a professional artist.  That is when I found Jamie Austin.  Now not only did I need a face, but I found that I wanted to make sure I had everything to look like a woman.  I had the shoes, the skirt, and blouse.  It was no longer a desire to be sexual, but to look feminine.  Now what would I do once I attained this look?  Did I want to go out to clubs and pick up men? No, I wanted to go shopping and try on a variety of clothes.  When I was all made up and dressed as a beautiful sexy woman I knew men would look at me and it was nice to know I had achieved a true feminine look, but it was no longer a sexual thing where I wanted them to desire me and have sex with me.  It was something where I wanted them to treat me like a lady.  I realized my true desires were not to pick up guys, but rather go shopping and maybe have a man take me ballroom dancing.  Even then, the dancing was more to feel the pleasure of wearing a dress and having it spin around and flow with beauty. 

Sometimes I regress, especially when i am only part time and go through the cycles of purges. Having lost all of my feminine things i need to start again with panties and just that makes me feel like a sissy and brings me back to the immature sexual exploration and fantasies.  My profile and interest tend to reflect these various levels.  Do I go and try to express the mature cross dresser or the exploring immature dresser?  

Monday, April 4, 2016

Isabella's first night out

Went out for the first time as Isabella.  It was quite an experience.  I had originally found a guy who wanted to get together with me, but he canceled that day.  I had everything together and was ready to go out, so I figured I would do it.  There was a drag show at the local gay bar.  I checked it out on Facebook and found that there was another cross dresser who was planning to attend.
Through Facebook I was able to contact her and planned to meet her there.
I got myself ready early with all of the touches I had available to me.  I had let my nails grow out for a few weeks and painted them.  I shaved my legs the night before in anticipation of my date.  I put on my corset and pulled it nice and tight.  Put on my wig and brushed my hair.  I really do love having long hair to play with.  Then I did my makeup with what little I had.  Just some foundation to cover up the beard and blend with the rest of my face.  Then I put on eyeliner, shadow, and mascara.  Got dressed in a nice skirt and top:
Fairly simple, but good enough.
I must admit, I was a little anxious.  How could I possibly be going through with this?  Maybe I could just go to the local sex shop, but then I got the message from my new friend to meet her there and I felt that was definitely the better way to go.
With about 20 minutes before I had to go, I could not find my keys.  I had never lost my keys before how could this be happening.  I usually keep them in my pocket or on the night stand.  Well it turns out I do't have any pockets and they got put somewhere else.  I searched all over for about 15 minutes and thought maybe this was a sign that I shouldn't go, but then I found them on the counter with my make-up.  Which reminded me to touch things up one last time before I headed out.
The drive over was a bit nervous.  What if someone recognized my car and wondered about the woman who was driving it.  Of course if was dark and very unlikely.  The other thing was getting used to pushing the pedals on a standard while wearing heels.
I got to the place and drove around the block a couple of times just to figure out where the best place to park would be.  Then I finally parked the car and walked in the door.  They door man asked for my ID and I handed it to him.  I was very nervous.  He looked and looked.  I told him this was my first time out.  He said I looked great and did a very nice job.  He also compliment me on my wig.
Then I stepped inside the bar.  There I was exposed to a group of total strangers.  For a moment I had no clue what to do.  Do I grab a seat at the bar and order a drink or just walk around?  Luckily as I was awkwardly trying to decide what to do my friend spotted me and with a big smile wave me over.  We met with a warm embrace.  Wow I had really done it.  For the rest of the night I could just be myself, Isabella.  It was a nice evening we met some of the people she knew there, watched the show and danced a bit.  I had to leave early, but had a wonderful time and was quite at ease by the time I drove home.
Some notes for my next adventure.  I should get some more make-up to enhance my cheeks.  Practice more with the eyes.  And perhaps purchase a fragrance to make myself smell prettier too.  Always open to suggestions to improve my female persona.

Tuesday, March 15, 2016

Dare to Shave my Legs

 It all started with a game of sissy truth or dare over Pintrest chat:




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  • Will you dare me or ask me a truth? Dares are more fun :p But I doubt you could come up with a really 'Sissy' dare could you? Let’s play a game. A sissy game!
    Pin sent

  • I'll start you with a truth. How far have you gone with your sissy sexuallity?

  • men wearing panties


  • Just Dress Up with Rosie Palm
  • Learn more at thechive.com
    definately c
  • What about you?

  • I have gotten a total make over as you can see from my profile pic, so definitely C.

  • Have you ever worn women's clothing in public?

  • I have not gone out in full girl mode but I have worn panties and leggings under my boy clothes. Do you go out in public dressed fully?
  • Ludmilla Von Lubitsch
  • so pretty! Love her dress!
  • Crossdresser Style: Totally beautiful
  • Sissy Bitch : Photo

  • I have often worn undergarments. I went out shopping a couple of times in girls jeans and once went to Walmart in jeans and a boat neck top with a padded bra underneath. I was wearing a fleece over that and I bumped into someone I worked with. She never said anything, so I guess it was subtle enough to not raise a flag.

  • I also enjoy going shopping and trying on dresses in the dressing room. Have you ever tried that?

  • Yes I have a few times at Old Navy, Target and a few department stores.

  • What is your best memory of going our en femme?
  • With Love From Courtney x
  • I know where I get my love of girly things… Do you??? yes I do.
  • Cross, Transformistas, Traviesas y algunas mujeres
  • Look I actually already had from a Jamie Austin Make-over
    Pin sent

  • This is from my best experience. I had a professional make-over with Jamie Austin. He brought out my full feminine potential. I have never felt like such a woman as when he had me all made up and spent hours just flirting with the camera and admiring my beauty.

  • I didn't actually go out afterward, other than driving home en-femme and having to pay a toll at a toll booth.
  • Wow sounds like you had a great time! What city were you in?
  • She Has An Extra Something
  • LOVE autumn! Cool weather means I get to wear anything & everything I want all day long under my clothes. Fun to sometimes push the boundaries ;-)
  • morecrossdressers: Visitmorecrossdressers... for more beautiful crossdressers, real crossdressers, cute crossdressers, crossdressing, mtf, male to female, men wearing dressess

  • The make over was with Jamie Austin in the Boston area. It was the best time of my feminine life. Still I have had some other fun just exploring how far I can push myself in shopping.

  • How far have you gone in you shopping excursions
  • Crossdressing Fashion See Suddenly Fem's FULL 2015 Fall Fashion Catalog ! Designed & Manufactured Specifically For The Crossdresser & Transgender Community ! See Full Catalogsexycrossdresserg...
  • Well Dressed Crossdressers and Transgendered Women

    I am envious of all these great looking CD's
  • Beautiful crossdressers, real crossdressers, cute crossdressers, crossdressing, mtf, male to female, men wearing dressess
  • She Has An Extra Something
  • cdmestephanie: soooo good! looks like she’s ready for a great night out – or maybe a date with someone cute…?
  • Joe, what's wrong? Sis, another night with mother, and she ran out of lub, so she went in dry.

  • I think the most daring shopping I did was to go to the make-up counter at Belk and get assistance on picking out the right foundation. The girl there was very helpful and I think she enjoyed putting make-up on a guy.

  • Have you ever asked for assistance with anything when you have been shopping?

  • Never, always too scared, I wish I had your courage.
  • cdmestephanie: soooo good! looks like she’s ready for a great night out – or maybe a date with someone cute…?
  • Learn more at facebook.com
    Beautiful Crossdresser#Venus_Belle -www.facebook.com/...

  • You should try to take it in little steps. I have almost always been treated very nicely. The only negative experience has been some people who gave me a look of disapproval.

  • The first time I asked for help was at a VS and I used the cover that they were for my girl friend.

  • Thanks for the advice!
  • Learn more at facebook.com
    Beautiful Crossdresser -#Venus_Belle
  • Learn more at facebook.com
    Beautiful Crossdresser#Venus_Belle -www.facebook.com/...
  • Learn more at facebook.com
    Beautiful Crossdresser#Venus_Belle -www.facebook.com/...
  • Learn more at facebook.com
    Beautiful Crossdresser#Venus_Belle -www.facebook.com/...

  • How old were you when you started crossdressing?

  • The idea of being a girl was with me since I was about 8. I probably didn't try on my first panties until I was about 12.

  • I started when I was 5, tried on my sister's swimsuit and have been crossdressing ever since. I love the feel of shinny spandex and pantyhose. What is your favorite part of crossdressing?
  • She Has An Extra Something
  • Where Boys Will Be Girls

  • Yes, the way the clothes feel is one of so many things. I guess what really has me hooked is just how it connects me with experiencing all of the sensual aspects of being a girl. The feel, the look,and even the smells.

  • The feel, the look are my favorite!
  • transgender transvestite transsexual www.dress-me-up.c...
  • via I care for Girly Boys
  • bettany tv

    I really love the look and feel of pantyhose on smooth legs!

  • That is an amazing one. I shaved my legs once and putting on pantyhose was the first thing I did. Wow, it made wearing pantyhose and even more sensational experience. I haven't had a chance to do it again since.

  • I know it is hard to hide saved legs, I did it during the winter and hid it under pants when I went out.
  • Will you dare me or ask me a truth? Dares are more fun :p But I doubt you could come up with a really 'Sissy' dare could you? Let’s play a game. A sissy game!
    Pin sent

  • I think I am ready for a dare.

  • Dare you to shave your legs wear panties and pantyhose for the rest of the week! Even when you go out in public! (you can wear it under your boy clothes)
  • A high protein breakfast helps you start the day right. Wearing pantyhose just perfects it.
  • Mega Shemale Fans
  • J'adore
  • Love the legs heels and hair
  • When do you need to wear pantyhose to work? When should you wear tights instead? When can you wear bare legs? So many questions... and we hopefully have the answers in our new Guide to Pantyhose for Work.

  • I accept your dare, although I may not get it done right away, as I need to find some time to shave. Thank you so much for the inspirational pictures and the advice on wearing pantyhose to work.
  • Pin sent

  • What sort of evidence shall I provide?

  • What did you have in mind? I will take your word for it if you let me know what your experiences feelings were every day.
  • women in pantyhose so sexy — heypantyhose: Pantyhose don’t need underwear.
  • pantyhoseheadquarters: Beautiful pantyhose butt and feet.
  • Man, the Japanese really got the panties and pantyhose combo figured out. This shot is perfect...straight seems...totally in focus...HOT!!! AdamMan

  • Thank you for sharing such wonderful inspiration. It really helps to keep me going.

  • I have started shaving by trimming some of the hair on my legs, but there is so much it is going to take a few more days.

  • Still I did make some preparations. I went to Walmart last night and got some nude panty hose to wear for work, just like was suggested. I also bought some tights for those cold days that are coming up and a pair of girly leggins because I want to know what those feel like too. I tried on some leggins once and they felt so nice. I can just imagine how much nicer they would feel with clean shaven legs.

  • I have also started with wearing panties. Today I have on my white boy shorts with lace trim.