Buying your first dress

What was it like buying your first dress for yourself? How were you feeling?

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  • Excited
  • Nervous
  • Blissful
  • Other

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This topic contains 39 replies, has 34 voices, and was last updated by  Rosiebeth 2 weeks ago.

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  • #242158
     Angela 
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    Registered On: August 27, 2019
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    I bought my first dress online. It was very exciting. I couldn’t wait to try it on once I received it. Last week I went to my local Lane Bryant store. I made an appointment with the SA that had done my bra fitting. It was a fantastic experience. I got to the store a little early and was browsing the store. She asked me what I liked what I would want to try on. I was asked for my name to put on the dressing room door. Of course I said Angela! I went in to buy more dresses but ended up with some leggings, skinny jeans, 2 tops, and ankle boots. I was on cloud 9 trying everything on. The SA helped with sizing different styles she was great! I can’t wait to go back and buy dresses this time and panties. I’m going to go as Angela this time.

     

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    • #242278
       Rosiebeth 
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      Angela

      that is most awesome girl.  I’m so happy for you having a great time.   It is so exciting when things go well and we can enjoy being ourselves and not have to worry.  Now go model all those new clothes girlfriend.
      😘

      Rosiebeth

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  • #241217
     J J Johnson 
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    Really all three, but excited is the top emotion.

    I was nervous picking it out and going into the dressing room, blissful when I made the choice and bought it, but excited about the whole experience,  both in the usual use of the world and excited in the sexual sense in that I was glad I wore tight panties that day to keep “things” under control.

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  • #240531
     Patty Phose 
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    Every time I buy something it’s because I want it bad and have to have it. I’m always kind of nervous but very excited.

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  • #240231
     Sharon Trying2findmyway 
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    My first dress was actually purchased for me by my wife!  I was pleased and beside myself with happiness that she would do that for me. The next time she took me with her and I was able to pick out a dress and some lingerie for myself.  That was the first time I was actually able to shop for myself.  Again I was pleased and thankful that my wife accompanied me.  I was very nervous but was more comfortable having her there to support me.  The last shopping experience that was the most exciting for me was in a large department store at the mall.  My wife was in the dressing room trying on jeans.  I was looking at dresses and found a pink lace skirt and top that was amazing.  I showed it to my wife when she came out of the dressing room.  She selected a size she thought would fit me and took me in the dressing room so I could try it on.  I felt absolutely giddy and ecstatic.  I was so excited I had to lean against the wall of the dressing room to support myself!  I loved the outfit and bought it!  Happy day!

    Thanks

    Sharon

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  • #239797
     Nobody Atall 
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    1. So the story begins with my friend. She was my best friend. At the time i had crossdressed in private (mothers dresses bras ect). I was staying at her house for the night and we were just chilling and then she jokingly asked “can i do your makeup?” i replied “sure why not” so then she did my eyebrows and everything made me look great. After that she gave me a wig and said “you look like a real girl” then i said “surley we do the full thing then” she was exited and i acted like i was joking. So she went and found me a nice bra, some tights, and a dress, then did my nails and we had a great night. Throughout the night i tried acting like i wasn’t completely loving every second of it but she could tell i was. Anyways a couple of days later she came over and said “lets go on a walk” and then seriously asked me if i wanted to do it regularly i said yes. So then she took me to the local goodwill shop to buy my own stuff. We ended up getting a bra and 2 dresses at once then getting tights after. An amazing story i love her so much for everything
  • #239587
     Mona 
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    It was at a thrift store (Goodwill) near work.  A simple purple bodycon dress that was/is way too short for me.  But I remember at the checkout, a lady in line behind me commented “that’s a nice dress.”  I’m sure she thought I was buying it for a female SO – was tempted to reply, “yes, I hope it fits me.”  But then I came back to my senses and just said thank  you.  Was nervous the whole time in that store and especially at the checkout.

    That was the first of many more thrift store dresses since then.  Now I shop openly and happily in the women’s sections – I don’t think anyone really gives a hoot and I sure don’t.  I’m sure they get cross dressers in those stores all the time.

    Great poll/topic by the way.

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  • #239564
     Donna Allen 
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    My first “dress” was actually a night shirt. There was a year in the late 60’s or early 70’s when night shirts were popular, even for boys. Both my older brother and I requested one for Christmas and we got them. First chance I got I snuck a pair of pantyhose out of moms drawer (which I had done many times)a tried on with my nightshirt. It was blissful!

    Eventually I started borrowing moms dresses and wearing them outside late at night. I don’t recall when I bought my first dress of my own but every time I buy a new dress I get that feeling of bliss all over again.

     

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  • #239537
     RandiL 
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    It was at a church thrift store that has nice stuff. They reject things that are too worn out. Mostly older lady volunteers who run it, but they are very supportive. I just went in, browsed, and took some things to the minimal dressing cubicle. When I checked out, a couple of the ladies were complimenting my choices, “Oh, I wish I could have that one.”

    On another trip there, I ran into a couple of women from work, one volunteering and the other buying clothes. We had to switch off seeing ourselves in the one mirror. No negativity from either one, although the volunteer did ask me why I was buying those things for myself (an honest question, not negative).

    I find knits work best in dresses, since I’m a 14 on top and an 8 on the bottom.

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  • #238917
     Daisy Marie 
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    I’m still choosing my first dress, when and where to buy, but if it happens outside internet world, I reckon I’ll be a mix of all these three feelings. On internet shopping, I wouldn’t be nervous, but surely I’ll take more time to choose (many many cute options).

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  • #238874
     Brittney Andrews 
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    I bought my first dress at my local super grocery store. It’s a blueish purple long sleeved knee length wrap dress. I was excited and a little nervous. I folded up the dress as small as possible and carried it against my side while holding the price tag in my hand. I used the self check-out and the moment of bliss hit me when I got out to my car. I’ve bought a few more dresses and skirts from the same place.

  • #238802
     Sheryl Johnstone 
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    Almost 50 years ago, the first dress I bought was from a thrift store in another town 50 miles from home.

    It was a lovely dark floral patterned, short sun dress with elastic waist and neckline and not only did it fit just fine but a few years later my new wife also wore it a few times while working in the yard or washing the car.

    I’m pretty sure that I have that dress stashed away in my  collection and it would still fit me.

     

     

    Sheryl

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  • #238680
     Morgan Staar 
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    I spotted the dress on the display rack at walmart. A cute cotton summer mini dress..perfect for summer walks…I was 15…a couple of quick passes up and down the aisle and once I convinced myself it would fit I scooped it up and headed for the self check out aisle. I also picked up some pantyhose on the way…In and out without interacting with a single human.

    The dressing is more deliberate these days now that I am confident of not being immediately outed.  And thank God for internet shopping…yay

    Morgan

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  • #238665
     Roberta Thomas 
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    I was about 36 and had been a crossdresser for 24 years before I bought my first dress.Prior to that I wore my mum’s dresses when I lived at home and my wife’s when I got married.I went to the Debenhams store in my capital city in the U.K..It was just a few weeks before Christmas.I chose a formal type dress.When I took it home it didn’t suit my body shape at all.It wasn’t in my preferred style either.I had bought in haste.Bought the dress with money saved from my office savings Christmas club.At that time my wife had no idea that I was a crossdresser.As I was too embarassed to take the dress back,I had to pretend to my wife that the dress was for her.Luckily,she believed me,told me the dress wasn’t her cup of tea.God bless her she took it back and asked for a refund.I had made so many attempts trying it on at home,the dress was showing slight signs of wear.They queried this but agreed a refund.I had a much nicer experience a year or too later.Just before Christmas again I went into a high end chainstore.I fancied a lovely red dress.The Salesgirl saw me looking at it.I asked her if she had it in a size 16.which is my dress size.She said the smallest was a 14.Sensing my dissppointment she said “Sorry about that,and you one you liked too”. I am sure that she read that it was for me.Had there had been one in my size I am sure she would have been very accommodating.

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  • #237879
     Cynthia Hughes 
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    I bought my first dress on my second trip out shopping by myself.  I had gone to the store with all the links on my phone so I was able to show the people behind the counter pictures if I could not find them myself.  After searching up and down the aisles I was unable to find the particular dress I was looking for so headed up to the counter to talk to the service reps.  The rep checked the computer and said that the dress was no longer in stock.  She shot around from the back of the counter and headed over to the rack and proceeded to pick out another dress and asked how I liked this one.  It was not what I really wanted but it was nice.

    It was never implied that it was for me,  nor did the clerk even as who it was for.  I paid for my dress and headed out.  Great time.

    Cynthia

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  • #237827
     Paula F 
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    I checked all 3 for the very first time I actually spent cash, by myself, for my first dress.  I had shopped with another person before, safety in numbers and all, but was on emotional roller coaster on my first solo shopping trip, elated, nervous, shy, excited, worried, and once I received my change at the register, blissfully happy that the world didn’t open up and swallow me.

     

    PaulaF

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  • #237774
     Britney Pardo 
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    My first dress I bought was a really cute white dress

    i was realky nervous because I was I my boy clothes nad I thought people would think I was a crossdresser (i am a crossdresser)but I want to keep my boy identity a secret

    So then I got back to my apartment and I just felt like a princess because I had all my make up on and a beautiful black hair curly hair vig

    well that’s my story

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    • #238319
       Rosiebeth 
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      Me too. Always dressed in men’s clothes while shopping for feminine clothing.  So far nobody cared and have been super nice.  The more I shop the less I get nervous because it’s alway a good experience.
      hugs

      Rosiebeth.

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  • #237663
     Anne Preuss 
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    My first dress is the red cocktail dress you see me wearing in my pics.  The red color was so bold and daring and I love how it sits off the shoulders.  I was so excited when I saw it on display at Penney’s that I knew I had to buy it.  So glad I did.  I feel so lovely in it.

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  • #237606
     Annie Potts 
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    The first dress I bought is in many ways my favorite.    Wore it the first time I went out in public.    Wore it for my makeover.   Looks cute by itself or with a jean jacket.  Love how I look in it.  Not too long.  Not to short.  Sooo comfy.

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  • #237558
     Heather Jameson 
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    I remember going shopping with my sister when I was 15 to by bras and panties, she was sick of me stretching her stuff. We were in la femme back then [late 70’s] and looking around and talking when the sales lady came over to see if she needed help. They started talking and the lady asked well is this for you or him and I said for me. She had a bit of a startled look on her face but said come with me. She took us in the back to a private room and started measuring me and brought in a few of each then motioned to a dressing room for me to try them on. I was so nervous my hands were shaking. I went in the room and tried on the first set and she said well lets see. I was petrified, I opened the door and she was right there and she said that’s not right and started adjusting my bra straps and explaining how it fits properly. I was in shock, then she said one more thing, leaves the room and came back with a pair of stockings, black sheer, thigh highs and gave them to me. I put them on and she asked if I liked it? I looked in the mirrored felll in love with stockings. I bought all of it, 3 sets of bras and panties and she threw in 3 pairs of stockings. She was wonderful and after that I’ve never been nervous going shopping again.

  • #237446
     Bettie Houston 
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    I remember my first time purchasing a new dress.  My wife had arranged for me to have a professional transformation to be followed with my first venture out in public in femme. I went to Lane Bryant and after a bit of searching a wonderful sales lady came and offered her assistance. Initially thinking that I was shopping for another, I explained that I was in fact shopping for myself and needed some assistance with sizing.  She took me to a dressing room, took my measurements and began to bring me various items to try on.  Eventually I settled on a wonderful black dress, she then brought me lovely black bra and panty set.  It was a wonderful experience and memory.  Additionally, I still have the dress

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  • #237427
     Leonara 
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    In my formative years of Crossdressing,when my wife was not home I tried on her dresses. Before I found CDH, another website ( thanks for the Internet) advised that it’s not a good practice to where another’s wardrobe. For years I purchased Christmas presents for Kathy in male mode, of course. As a husband, I had no hesitation to go to the ladies department to make my selection of skirts, dresses, sweaters, and tops for my wife…..five Christmases ago, it was my opportunity to buy clothes for Leonara and Kathy.
    Since Kathy is an 8 petite and I decided, since they were tight and short, a misses 10 would fit.
    When I went to the register the SA pointed out the selections were different sizes… I smiled and said “Thank you, Ma’m, I know”. She was very professional and to this day Macy’s is my go to store… I now buy online and pickup at the store.
    My last purchase were very feminine nightgowns and bras. One of our sister’s here on CDH mentioned the SA knows exactly what I purchased… Hmmm. Let’s keep her guessing lol !!
    Ladies, Thank you for listening… Leonara

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  • #237394
     Alice Underwire 
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    Buying my first dress was a very long time ago.  I think it was at a rummage sale at a local church.  It was just a dollar or two and I didn’t know if it would fit.  I answered excited to the poll because I was in drab mode but found this knit sweater dress and thought it would fit.  Later I found the dress was snug but I was able to get into it.  I hadn’t bought a dress before so had no concept of sizes.  I was thrilled to buy it.

    Alice

     

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  • #237365
     Danny Amone 
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    Registered On: September 30, 2019
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    Always excited.

    I don’t remember where I bought my first dress maybe Sears or Penney’s but I do remember buying my most expensive dress. It was at Torrid, I saw THE LIP dress in the window and just had to have it. I went in and asked about it, they had one in my size. It was $50, I also bought a pair of leggings to go with it. I will have to post a picture of my outfit someday.

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  • #237330
     Christinajane 
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    I count my first dress as when I walked into a dress shop in full drab and asked politely if I could try a dress on. No stories no excuses I just liked the look. I was so thrilled when it looked great I asked if she would like to see it which she declined – then while buying the dress she asked if I would like to join me their loyalty program I felt so accepted and happy. I have at other times bought clothes cause I was going to a party dressed up- for my cleaning lady and once when I bought quite a few items from a department store the lady at the checkout suggested I was buying them for my wife in hospital. I had to smile and nearly said “no they are for me”

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    • #237336
       Rosiebeth 
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      Glad you had a great experience right out of the gate.  That is most wonderful my dear.  Don’t you just love the look on a persons face when you say “ no, there for me”. Lol. Makes me giggle every time.
      hugs

      Rosiebeth

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  • #237326
     Bettylou Cox 
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    Not only was I nervous first time buying a dress, but before that, first few times buying leggings, shoes, panties, and even my first ladies’s tees. My outlook has changed so much in the past few months. Now, I can shop the stores with all the confidence of a GG, even in drab.

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  • #237282
     Ellie Hope 
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    Registered On: October 3, 2019
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    I am so fortunate. My two supportive daughters took me shopping to help with my first dress. We were at our local TJ Max. Their process required me to show a clerk stationed at the dressing rooms the items I wanted to try on, so there was no stealth mode possibilities. The clerk was very accepting and helpful for which I was so grateful. In fact we even began to joke about the endless stream of clothing candidates being rounded up by my “advisors” going through the racks. I lost count of the number of trips I made in and out. It was exciting, scary, inspiring, sexy, and, to be honest, tiring. But I would not trade those blissful hours for anything.

    My most scary and nervous event, however, occurred a few years earlier, when I went solo to Victorias Secert dressed in drab. This was the official beginning of my X dressing experiences. Upon entering, the first clerk I saw came right over asking if I needed help. I  am no good at lying, so I confessed my desires to dress as a lady, and my goal for that day was to buy a nice bra and some panties.  But being completely ignorant about these things, I requested her help to fit me correctly and offer some basic information. She seemed pleased to help and  was very encouraging. It was a class act. She measured me privately, explained about some of the options with their pros and cons, and offered her advise including personal opinions with regards to trade offs of various selections. She put me in a private dressing room away from the others and brought me several bras and panties to try on. She knew I needed help adjusting straps and was happy to come in a assist. It was done discretely and very professionally. I was on cloud 9 the rest of the day. Exciting, terrifying, blissful, humiliating, joyous and satisfying are some of the things I felt during that experience. Those two bras I purchased at that time are still my favorites, one very comfortable, the other absolutely gorgeous. That experience is one of the most positive things to ever happen in my life. To Anna, my clerk, I am forever grateful.

    Hugs to all

    Ellie Hope

    • #237284
       Rosiebeth 
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      Those both sound like wonderful experiences and to get that much input.  Most jealous. I am most glad hon that it all went so well for you on your first adventures out buying clothes.
      hugs

      Rosiebeth.

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  • #237273
     Amber Martinez 
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    Omg that was so long ago when I finally bought my first dress on my own .I was very very nervous of course but as time went on my nerves went away.

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  • #237253
     Rozalyne Richards 
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    I was very nervous when I bought my first dress, it wasn’t a new dress it was from a thrift shop i made a point of going early in the morning while no-one was around, it was great trying it on afterwards, it feels great when the dress fits you so well even though I’ve not tried it on x

    • #237285
       Rosiebeth 
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      I bought my first skirt also in a thrift store.  They are wonderful places to feminine clothes because they don’t mind because they just want to sell them. I’ve purchase most of my girl clothes at them.  They really do have some beautiful options at great prices.
      kisses

      Rosiebeth

  • #237242
     Giselle Reeves 
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    i bought my first new dress at a dressbarn location in the Grove City Pa. Mall

    i was nervous as can be and also bought two pairs of pantyhose there and when i

    showed them to  my wife(who had only known about Giselle for about a month at the time)

    she was not impressed, so i got the silent treatment for the next few hours.

  • #237224
     Kim Michele 
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    I was nervous, bought one and got out of Walmart.  It fit very well, just dumb luck though.

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  • #237221
     Kathryn Lynn 
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    Bought my first 2 dresses in 1999, none since 😣. But it was exciting, thrilling, nerve-wracking, and oh, so sexy! <sigh>

    Love, Lorrie

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  • #237214
     Danielle Silverfeather 
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    I was nervous, excited and frightened all at notice. It is the way each time I buy one as David. If I am Danielle there is no fear.

  • #237206
     Rosiebeth 
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    I just bought my first dress.  I just bought my first dress.  I am beyond excited.  I went to the ladies department and pick out a dress and tried it on and bought it.  I am soooo happy I could scream. Nobody cared.  I haven’t stopped smiling.   The rest of the day I am taking a bubble bath, shaving my legs and using lavender body lotion and slipping into my new dress.  I am so happy and excited and feel like I took a big step into Rosiebeth.
    kisses girls

    Rosiebeth.

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