Halloween Fun

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My perfect date

For me its not just about dressing up like a girl, I enjoy the process, the feelings, the acts. I enjoy doing the things that women get to do that men normally don't. I want to know what its like not just to dress like a female but what is it like to be a female. I can have a difficult time with this because I feel like I'm pretending, but it's an interesting study in perspective. I have been out in public many times, so going out is no longer that big of a deal. I enjoy it but I have done it before. One thing I haven't really done is go on a date as a female. An actual date with someone I could get to know, flirt with and see where things go.

But if I did that what are some girly things I would enjoy.

- I think my ideal location for going on a date would be in Las Vegas. There are so many restaurants and bars and fun things to see and do. I would happily go the The Peppermill Fireside Lounge for an ice cream drink, my favorite is the Pink Squirrel. I would equally enjoy going out for a drink at The Sunset Lounge in Hyde at Bellagio, a fun romantic spot to watch the fountains. I could also enjoy a nice meal and conversation at Mon Ami Gabi at Paris.

- I think I would be happy either meeting my date out at our predetermined location or having them pick me up at my door and going out. While I have gone out solo dressed up in Las Vegas, It's just easier to be with someone else. You can talk to them and not think about everyone looking at you.

- It may sound corny or old fashioned and probably sets feminism back a few decades, but I think it would be fun to have my date order for me. Something like, "I'll have a gin and tonic and she'll have a Pink Squirrel."

- I would consider myself lucky to have a commemorative picture with my date. Sometimes the bars or restaurants will have an on site photographer who takes pictures to sell to the patrons. I could lean in and try to look cute for our photograph, hanging onto my dates arm.

- As we sat and chatted while getting to know each other it would be exciting if my date leaned in to whisper sweet nothings in my ear. What can I say, I'm a romantic.

- I do consider myself more passive. I like someone to take charge, just not overly aggressive or mean spirited.

- Assuming things went well on the date I would very much enjoy a limo ride on The Strip. My date wouldn't be able to keep their hands to themselves and would get a little "handsy" in the back of the limo.

- A lovely stroll along the promenade in front of the Bellagio to watch a fountain show could be nice too. Being out in public, on the arm of my date, holding my hand or with their arm  around my waist.

 - I would enjoy the little things associated with being treated like a lady; having doors held open for me, help getting up or down in my chair or into or out of a limousine.

- It is Las Vegas after all so a quick stop at the roulette table to make a bet, even if it is just one bet. Just being there with my date who is proud to be out with me just as I am proud to be out with them in public.

- These items above, of course, are more about romance, but that doesn't mean I can't be a little risque too. 

- Public displays of affection anywhere from a light peck to a full kiss or maybe having my ass grabbed surreptitiously could be fun.

- I do own a Hush toy by Lovense which can be worn in public and is quiet enough to not be noticed by casual bystanders. It is managed via an app on an iPhone so your partner can sneak in some exciting playtime while sitting in a restaurant or walking around town.

- Again if things go well and we have some private time together I prefer a sensual encounter, no bondage or rough treatment. I want to be taken and feel like a woman whether that is lying on my back with my legs wrapped around my lovers waist, taking it doggy style or riding them like a cowgirl.

- Sex is not just about me either, I want my date to enjoy themselves and I have another toy that everyone seems to enjoy, a Hitachi Magic Wand. Fun for all and all for fun.

- I also have a bit of an exhibitionist quality to me, as if wandering around Las Vegas dressed as a girl wasn't enough. The thought of standing in my lingerie in front of floor to ceiling windows caressing my lover excites me. Are the room lights on bright enough to be seen from below? The windows are so far away across the Bellagio lakefront, even if they could see would anyone even be paying attention? That is exciting to me.

-  I do tend to overthink things and may end up "topping from the bottom". A giant list of things I would enjoy might fall into this category. Of course I would enjoy any one of these things, or just a few of them. I certainly don't need to do all of them. Maybe my date would like to see or do something they like or show me something I never knew existed. It's a two way street.

- One last comment. Not everyone wants to be in a picture but might be happy to take a photo of me instead of with me. Maybe they don't want to stand in front of a window for everyone to see or even something simple like drink alcohol. All things have to be consensual. It doesn't matter if you are a male, or a female or a male dressed as a female. Consent is mandatory.

Weighting - Follow up

So I know I posted the progress I was making weight wise but didn't post a follow up.  I did get under 200 pounds for the Vegas trip. The last time I checked at work before the trip was May 26th and the trip was on June 30th.  At that point I was 198.  I jumped back up over 200 pounds as a result of eating a lot during the Las Vegas trip but I recovered and have been pretty stable, just under 200 pounds since then. After all, I have a wedding dress photo session we are still planning.

I have performed a couple of time since the weight loss and you can really tell. A couple of my costumes I need to adjust to keep them from falling off. I also have had comments from my girlfriends noting how much I have lost.  I suppose it has been about 10% of my bodyweight so that really does make a big difference.

Hopefully I will be able to keep my weight right around 197, I'm not sure what I will do once winter comes around and I can't run any more.

Just A Few More Days

I have two semi busy days left before the trip. They are only semi busy because one day is a Holiday and the other I have the day off  of work, but there is plenty to do on both days as well.

Today is packing day. I will set out all the clothes I plan to bring and check off all the things on my list of to do's. I still have to go through my makeup bag and bring only the things I will need. I also have to decied what goes in the carry on versus by checked baggage. I don't want to miss anything on Thursday so I will likely carry my wedding salon visit items and Thursday show items in my carry on.  Everything else should go into my checked bag. It's also tough because I'm not 24x7 dressing as a girl so that means two different wardrobes. You can see its a very comprehensive list.

Wednesday

-arrival

unders and sox - wearing

shorts - wearing

T shirt - wearing

pom sneaks - wearing

 -steak night

Unders - repeat

White t-shirt

Blue linen shirt - dry cleaner

New jeans

Black sox

Black Boy shoes

New jacket

Blue pocket square - dry cleaner

-After dinner

Unders - repeat

Tshirt

Shorts

Sox

Pom Sneaks- repeat

Thursday

-wedding salon

Blue silk dress

Pom sneaks - repeat

White long line bra

White gaff

White ruffle panties

Puma Purse

Jewelry

Wedding rings

Earrings

Necklace

Bracelet/watch

Crystal heels - bring along

White stay up stockings - bring along

  -show

Pink Ombre dress

Poir Moi

Strapless bra

Thong panties

Garter Belt

Black gaff

Black seamed stocking

Jewelry

Betsy Johnson Cat necklace

Matching earrings

Crystal and gold necklace

Wedding rings

Crystal heels - repeat

Black/gold wire purse

Friday

  -hiking

Unders

Sox

Hiking shoes

Shorts

Tshirt

Extra Tshirt if I sweat through it

Hat

  -Friday night out

Unders

Sox

Pom Sneaks - repeat

Shorts

T Shirt

Saturday

-poolside

Bikini - delivery?

Pom Sneaks - repeat

Red flower dress

  -show

Blue Satin dress

Pour Moi

Blue/Black basque

Blue/Black panty - delivery?

Black gaff - repeat

Two tone stockings

Bronze stockings - just in case

Black felt cutout heels

Leopard wrap

Leopard muff

Blue brooch

Jewelry

Crystal

Something blue from DuBarry's

Cat Ears

Sunday

-pool or wander

Bikini - repeat

Pom Sneaks - repeat

Red flower dress - repeat

T Shirt

Unders

Sox

Pom Sneaks - repeat

Shorts - repeat

-Sunday night show

Unders - repeat

White t-shirt

Purple pricey shirt

New jeans - repeat

Black sox

Black Boy shoes - repeat

New jacket - repeat

Purple pocket square - dry cleaners

Peacock Bowtie

Monday

-day in Vegas

Unders

Sox

Pom Sneaks or hiking shoe - repeat

Shorts - repeat

-depart

Tshirt - change

Extras -

Black kitten heels

Black maxi dress - backup

Nighties/panties/robe - wash

Wedding shoes

Wedding dress garment bag

Cash - in basket

Iphone

Ipad

Chargers - lightning and watch

Headphones

Keys

Wallet

Toiletries

Tooth Brush

Toothpaste

Floss

Deoderant

Eye drops

Gas x

Scrubbing face brush

New razor Blades

Shaving gel

Hair binders

Comb

Tweezers

Small scissors

Contact Lenses

Flask

Itinerary

Tickets

Makeup and brushes

Hairpins

Sponges

Make list

Makeup wipes

Girl glasses

Sunglasses

Girl readers/sun readers

Hand fan

Lighted makeup mirror

Hair clips ins

Breast forms

Hair curler thingy

Sponge curlers

Pool purse/bag

Toys

Aneros

Stroke 51

Magic Wand

Tomorrow I have a hair coloring appointment in the morning and and mani/pedi in the afternoon. I also have to hope my last shipments arrive in the mail. I have a new band ordered  for my Apple watch, something a little more girly. I also have two things coming for the trip. I ordered a bikini bottom for my swim suit, same style but not high waisted, and a pair of panties for my Saturday lingerie. I am having a hard time matching the blue of my basque. If they don't show up I will need to go to Victoria's Secret and just get a skimpy black pair of panties. They will work but I'd rather have the matching set.

On Tuesday I leave for Las Vegas.

The real work begins

Over the past few weeks I have been dutifully filling out my spreadsheets, planning what to bring where I can pack it, going to the store to make sure I have fresh razor blades and new false eyelashes.  That was all kid stuff compared to what is in the works starting today.

Yesterday, I had my body waxed and I still feel sticky.  Its surprising how long it takes to find all the hidden, sticky wax bits after you are done.  The waxing itself takes about 90 minutes to do both arms, both legs, my chest, my back, my butt, and then getting a nice bikini line. Nobody wants to see yucky boy hair sticking out when I'm wearing my bikini at the pool. Waxing is awesome for a nice clean feel and you don't get stubble for a while. That's very important when you have a few nights of dressing up on the schedule. I want to be able to focus on hair and makeup and not have to shave again the next evening before slipping into my stockings and garter belt.

This weekend is finalizing a few things, and I get an extra day since its Memorial Day weekend here in the US. I will spend some time working on my eyebrows. I have had them waxed in the past but they always do a natural full brow. I am hoping to pluck them a little tighter than normal from the bottom up so its a little thinner than I normally wear them. They'll grow back, right?

Tuesday is the day before I leave and that will be a busy day as well. I have my hair color appointment as well as a manicure and pedicure. I love the feel and look of a nice gel nail extension. The color is baked right into the process so my nails will be pretty for the duration of the trip. Some people will notice my long colored nails when I'm waiting in line for airport security but who cares. My nails will look beautiful dammit.

Just a quick note on where I stand with my weight loss plan for the wedding dress fitting. My last weigh in before I leave for Las Vegas I came in at 197.5 pounds. Yay Me! I should be able to slip into the wedding dress with no problems. I shipped it off on Tuesday so it will be there when I get to Las Vegas.

One little thing to leave you with. After my waxing and weight loss I just had to do a test fitting of my black and pink lingerie. This is my official Thursday night show lingerie.

Its Been 10 Days, lets talk shoes

Oh my, how time flies. Its been ten days since my last post and and I only have eleven days until I fly off to Las Vegas. I think I have pretty much everything planned but I have a couple of things left on my to do list. First off is the shoes I am going to wear. I have a few pairs I will be bringing for various reasons.

1. I have a pair or custom ordered Chuck Taylor low tops. They have black bumpers and black laces but the canvas is a super cute pomegranate print in red, white and blue. These will be my generic walking around shoes. I can wear them to and from the bridal salon, out to the pool with my cover-up and bikini or just around the casino.

2. Fancy shoe #1 - I have a pair of strappy stiletto heels from Dolce Vita in silver, they are pretty cool. But I have spent  some of my free time rhinestoning the heck out of them so there is a ton of sparkle. I'm super excited about them, everyone is going to freak out when they see my shoes.

3. As much as I like my fancy shoes the heels are super high and after a couple of hours in a pair of torture shoes, I may need to go to a shorter heel. So my backup shoes are a black Mary Jane with a kitten heel that should go with both my evening outfits.

4. I am debating on what to wear with my Saturday Night outfit, I could wear the same sparkly shoes but I also own a pair in black felt that I didn't sparkle the crap out of. I might bring those just because I don't want to wear the same shoes on two nights. What kind of a fashion maven would do such a thing?

Only one week until my waxing and I get to be smooth as a baby for my time in Las Vegas.

Lingerie Options

As I prepare for the big Vegas vacation I am building out my list of things to pack and wear.  I am a huge planner, I like making lists and checking things off and organizing so I am sure to have everything I need. I might even make a blog post out of it soon. But for now I am trying to organize my outfits. I have three main events in Las Vegas and while the outwear will steal the show for everyone that sees me, I am one of those girls that likes to match my underwear to my outerwear. So lets go through some of my lingerie options.

Outfit One - is a sparkly pink and black hombre gown, and with it I was going to wear a basque from Pour Moi Lingerie and just remove the shoulder straps. I have the matching panties in the same Jewel/Black color. The beauty of wearing a basque is that it allows me to wear fully fashioned Gio stockings with my outfit.

Outfit 2 - would be for the wedding dress fitting. The dress is strapless so I need appropriate underwear for the fitting and I can just wear that under the casual dress that I will wear to the wedding salon.  I have tried a corset that I own and it doesn't work well with the wedding gown. I really am left with two options. On the left is something like a lace teddy but it is backless, the halter strap in the picture is removable and it has little tabs that are sticky on the sides of the bra, the bra cups are also sticky so it stays in place via the stickiness instead of boning and straps. The option on the right is a La Vien low back longline bra. I can wear stockings with either outfit but the La Vien has garters where the lace teddy I would need to wear hold up stockings.

Outfit 3 - I don't have a picture of but it is a blue satin tea length gown with some pleating around the skirt that give its some fullness, I would say the silhouette is A line. There is also an accent of black satin right across the top of the bust. The dress is also strapless but the back is high enough to wear a basque again or a strapless bra and garter belt set.  I am having some difficulty finding what I want in the right colors. I tried another Pour Moi set but they don't make a garter belt in that color and I don't like the black one I bought to go with it. At this point my option would be to purchase the same basque as above but in blue and black. But then I would basically have the same lingerie for both outfits just in different colors or I could try to find a different set of lingerie for outfit one. I really want to be able to wear stockings with this outfit. since I will have a little leg showing due to the tea length dress I can wear tan stocking but the welt of the stocking is in a contrast black so it would go so well with the basque.

I need to figure this out quick, only 22 days before I am on my way to Las Vegas.

Those In The Know

There are so many crossdressers that are afraid of being found out, I myself used to be one of them. Even to this day I am out, but not OUT. I lead a sort of a double life; those who know and those who don't. Ultimately progressing in my adventures may come back to haunt me but I continue to expand the number of people who know about my dressing.

The friends I have had since childhood and I still see regularly today are not familiar with my crossdressing adventures. Well....that's not entirely true, I have on a few occasions shown up to a Halloween party as a bride, Cher and Cyndi Lauper. But those were costumes and there is a difference. I don't expect that any of my friends would mind if I told them about my crossdressing. I don't think they would want me to show up to Thanksgiving dinner in a party dress either but I think they would be OK with the fact that I dress up sometimes. Some may even want to see it.

But when I think of how closeted I was in the past to where I am now, I was curious to think about just how many people are aware.

First off, my wife. She knows I dress up and is fine with it. She helps me with sizing and fashion advice, buys me the occasional gift and will go out in public with me dressed up too. Not wanting to hide this from her, I told her after about two months of dating just so she was able to make the decision herself if she could live with my crossdressing. That was about 11 years ago, so I think she is OK with it.

Second is what I'll refer to as my burlesque friends. My wife bought me a series of burlesque dance lessons for a birthday gift about eight years ago and I've been dancing with them ever since. Initially it was my burlesque teacher, and the students, then more students and the people who came to watch our shows so that has kind of exploded the number of people. I don't know a most of the audience members by name but some and of course my girlfriends have boyfriends or husbands whom I've met and chatted with. I would put this number at around 50-100 with varying levels of familiarity, excluding audience members.

Within the burlesque community I have about ten close friends who I perform with or takes classes with a lot and I have two besties who I would call my girlfriends, not dating girlfriends but who I hang out with a lot whether I am dressed as a girl or not. These are the girls that will be joining me at the wedding dress fitting and shows in Las Vegas, along with my wife.

My Besties

I also have a number of service providers that I have some contact with as well.  I have my regular nail salon tech, my hairdresser, the guy where I get my body waxing done, I have met with a couple of different makeup artists and photographers who I've done photoshoots with. 

And lastly are the random encounters, this would be the last group of people who I have interacted with while dressed. This would include bartenders and waitstaff at restaurants, retail workers at makeup retailers, womens clothing shops, Victoria's Secret and all manner of locations, movie theater staff, etc.

It's really not that hard to be out and about and the number of people who are aware of you just grows and grows.

Waiting and Weighting

A little more information on the wedding dress fitting event in Las Vegas. As I said in the previous post I purchased the dress on a previous visit to Las Vegas in November of 2017. At that point in time I was on a running schedule to prepare for a half marathon and as a result my weight was a pretty respectable 205 pounds. That was my weight when I went in and was trying on dresses.

Again as I said before I fell in love the dress and bought it, the store model actually fit me quite well but I was buying MY dress, a brand new dress made just for me. So we took measurements and add a little extra length to it because I'm tall. I took about four months from the time the order went in and when the dress was delivered.

Those four months were winter in Minnesota and even when training back late October there were some very cold and windy 30 degree runs. I don't belong to a gym so like most winters I just don't exercise as much. Well, over those four months I went up to 216 pounds. When the dress arrived, those extra ten pound didn't help me at all trying to get into my brand new dress. I wasn't able to get it zipped up. That was no good at all, after spending my money on my dress and I couldn't even wear it.

Back when I purchased the dress the salon owner said I might need to get it altered once it arrives. I could do that in Las Vegas at the salon or have it done locally. Initially I though I would do it locally but with the shows coming up in May/June I thought I might be able to do it in Las Vegas. And that would give me a few months to try and get back into wedding dress shape.

I have tried diets and exercise in the past without much movement on the scale but now I had a mission. I needed to get down to 205 pounds by May 31st, the day of my fitting which I scheduled back in March. So now I was going to start tracking my weight every Monday. My regimen consisted of smaller portion sizes, less sugar (no soda's), less beer, more fruits and vegetables, and starting to run again.

Naturally winter decided to make things hard and it was on April 14th that we had a blizzard that dropped one foot of snow on us. Things had been looking better up until then, the sidewalks were starting to clear, I could run in 30 to 40 degree weather and I was making progress. When the snow hit I had to stop running and I decided to dust off the old T25 exercise DVD's and try that. I could only do those on Tuesdays and Thursdays though.

In order to meet my goal I would have to lose about one pound a week over 11 weeks, that was my minimum. I set a secondary goal of 200 pounds, I called that my ideal weight. I wanted to have a little wiggle room if I needed it. Then I tracked my actual weight and charted it so I could see how I was doing.

At this point I have five weeks left and things are going very well.  I have actually made my wedding dress minimum with time to spare. I am continuing to work to lose that last five pounds to get to my ideal wedding weight. There is even a chance that I can surpass it. I graduated college in 1990, since then I have been under the 200 pound mark only three times. I hope to see a fourth.  Here is a chart of my current progress. Wish me luck.

The Events of Summer

Las Vegas 2014

Depending on how you count I have anywhere from 2 to 5 events planned for the next few months.

First, I am going to Las Vegas at the end of May with my wife and friends to attend some shows and generally have a fun time. At a number of points during the trip I will be dressed up in all my girl finery. We have two shows that I will definitely be dressing to the nines for. We also have a pool day planned and I will be wearing a bikini at the hotel pool. So I guess you can count that as one or three events.

Also, while in Las Vegas I have another event planned. Back in November I was in Las Vegas to run a half marathon and while I was there I decided it could be fun to go wedding dress shopping, at a real bridal store. It was every bit as fun as I had imagined, trying on beautiful dress after dress. Well, one thing led to another and ended up buying one. Silly me. It arrived about a month ago and I plan on having a final fitting to get the hem and fit just right.

I told my girlfriends about the dress fitting and they want to come along and join in the fun. So now that is an additional event while I'm in Las Vegas. Girls day at the bridal salon. Of course I'll have to make sure my wedding lingerie works with my wedding dress so, I'll be wearing that and a easy to get into and out of casual dress when we go. If I'm doing that I might as well do my hair up too.  Just to get an idea of how the whole package will look. There will be pictures.

Finally, after we get back from Las Vegas and the dress is all perfectly fit there is one more event on the horizon. The girls who are going with me to the bridal salon are a couple of my burlesque friends.We actually do an act where I am Marilyn Monroe, they are wearing tuxedos and we perform to Diamonds Are A Girls Best Friend. Recently, they told me about this cool old mansion where we could do a photo shoot.I thought we were going to do promotional photos for our troupe, but it turns out they want to wear their tuxedos and I will be wearing my wedding dress. Little old bridal me with two "grooms" for a photoshoot. That will be so much fun, I am super excited. And so are they.

So that's it, somewhere between two and five girly events depending on how you count it.

34 days and counting to Las Vegas

Dream Board

While talking to Fiona from Sissyschool.com, she thought a Dream Board might be a good idea. So I started gathering photos of the things I plan to wear, will wear or would like to wear during my summer adventures. I also hope to get some nice pictures of the events as they occur too.

What events you ask?  I will post them here soon, so much to do and only 41 days to do it.

I know this is a quick post but here is the link to my Dream Board on Pinterest.

https://www.pinterest.com/heisthebride/2018-sissy-gurl-summer-events/

Countdown Timer for Las Vegas 2018