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Thread: Advice for a New Crossdresser

  1. #1
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    Advice for a New Crossdresser

    Hi, I just wanted to say hello to everyone as a relatively new crossdresser that is still finding his way with this all. I first started experimenting about 2 months ago and after a brief attempt to stop I have found myself restarting again in the last couple of weeks and now see this as something I’m going to explore further.

    I had never really thought about crossdressing before but about 2 months ago I was housesitting for my aunt and uncle who had gone away for a few days. Whilst looking for a phone charger I inadvertently stumbled upon my aunt’s lingerie drawer. My aunt is a fairly conservative person and so I was slightly caught off guard by the sight of lace and nylon panties. During my time there, I tried on some of the panties and silky slips that I found and was instantly hooked. When I eventually left the house I took with me a pair of full cut black nylon panties with a lace trim, a hi-cut pink nylon pair with a lace trim, a silky white pair of panties and a plain white cotton pair. My aunt seemed to have a few pairs in these styles so I thought it would be less noticeable that they had gone missing.

    Over the next couple of weeks I would wear at home in secret during times when my parents were out. However, whilst I enjoyed the wearing I would experience feelings of shame afterwards. As a result, I then had a purge of the undies in an attempt to stop. However, the urge never truly went away and on a subsequent visit to my aunt I ended up taking a few more pairs of panties. On this occasion, I ended up taking a hi-cut lacy red pair of panties, two pairs of full cut black nylon panties with lace trim and a full cut lacy white pair of panties.

    I haven’t told anyone about my dressing and I anticipate that there would be a negative reaction from most people that I know. At this stage, I am still not ready to go shopping but would like to explore dressing further. It is therefore likely that my dressing will have to continue in secret for the foreseeable future. My aunt and uncle are due to go away again this weekend and will be giving my parents a key to their house so that the goldfish can be fed whilst they are away. I think this may enable an opportunity to take my dressing a bit further than just beyond lingerie and so as a novice was wondering if anyone had any advice on how to approach?

  2. #2
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    Yes, go buy your own clothes. Stop stealing your aunt's underwear and wearing her clothes. I guarantee she would not appreciate it, especially if you are an adult.

  3. #3
    Senior Member Majella St Gerard's Avatar
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    I agree with Vickie, snooping is one thing, trying on and stealing your aunt's panties is quite another. How would you feel if someone did that to you? Go buy your own stuff. With that said, welcome to the club.

  4. #4
    Gold Member Helen_Highwater's Avatar
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    If there's one way to raise suspicion you've found it. How many more items are you going to take before it gets noticed.

    I fully understand your reticence to buy your own. Buying women's underwear in drab is a daunting prospect. However there are many alternatives not least is online shopping. Buy through Amazon and you have the opportunity to have things delivered to a locker for pickup. Many other retailers offer click and collect or delivery to a local convenience store for collection. You have NO excuse for stealing.

    Also have you considered that if your Aunt notices things dissappear only when you're looking after the house, she may say something to her sister!! Alternatively she may start to suspect her husband? Think about where that could lead.

    You've, in your dressing, started into what we here consider to be a wonderful world of discovery. On this forum you'll find all the help and support you need. Just don't let your initial excitement take you down a path to family discord.

  5. #5
    Member nikinylons's Avatar
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    We all pretty much started in our mom's or aunt's lingerie drawer. Don't be afraid of who you are or what you want to buy. Just do it. Online CD/TG friendly shops are out there. For pantyhose and lingerie, I shop at Leggs online. Search it and order. Be a big girl and don't be afraid. We are living in the most accepting times of our lives.
    I'm half the man I used to be, and twice the person that I once was...and Nothing beats a great pair of L'eggs. Be all you can be ladies! WARNING:Any institutions or individuals using this site or any of its associated sites for studies, projects, or any other purpose - YOU DO NOT HAVE MY PERMISSION To Use Any Of My Profile Or Pictures In Any Form Or Forum Both Current And Future.

  6. #6
    Platinum Member Beverley Sims's Avatar
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    Yes.....

    Welcome to the forum and buy your own clothes.

    You were placed in a position of trust and all you did was steal underwear.
    Work on your elegance,
    and beauty will follow.

  7. #7
    Call me Pam pamela7's Avatar
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    welcome "new wearer". as others have said, do not take others' clothes. It's a tough step, but a man can go into a shop and buy womens' clothes - sales assistants have seen everything, and it is very normal for a man to buy women's clothes. Yes it can feel embarrassing, so go shopping in early morning/late eve when there are less other shoppers around.

    One of your first things might be to choose a female name for us to use here.

    Depends where you live but people are tons more accepting now than they were. in some parts it's almost fashion for men to cross-dress. you might want to try more androgynous clothing for early outings.

    best of luck - it's an adventure
    https://www.youtube.com/watch?v=dJFyz73MRcg
    I used to believe this, now I'm in the company of many tiggers. A tigger does not wonder why she is a tigger, she just is a tigger.

    thanks to krististeph: tigger = TG'er .. T-I-GG-er

  8. #8
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    Hi all,

    I suppose buying will be a step that I eventually will have to take no matter how daunting it seems at this stage. Moving forwards, I certainly wouldn’t want to create discord between people so I guess my current approach cannot be a long-term solution. My aunt hasn’t mentioned anything thus far and so I am unaware if she knows anything at all.

    With regards to a female name, how did you select yours Pamela?

  9. #9
    Lisa Allisa's Avatar
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    How do you know there isn't a hidden camera? I know she has noticed her panties missing, you made a disturbance in the order.
    "you are a strange species and there are many out there;shall I tell you what I find beautiful about you ,you are at your best when things are at their worst" ...[ Starman]
    It may of course be a bit disturbing to sense that one is really not so firmly anchored to the gender one was born into.

  10. #10
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    I'm fairly certain there isn't a camera in place. However, even though I tried to be careful to replicate the order as best I could I guess that could be a possibility.

  11. #11
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    Dear New Wearer,
    You are on a road to trouble. Stop stealing your aunt's lingerie and go out and buy your own. Its fine to be a cross dresser but not a thief.

  12. #12
    Silver Member Sometimes Steffi's Avatar
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    Wow! You stole 5 pair if your aunt's panties and you don't think she'll notice. She may have a full drawer of panties, but how do you know that the " hi-cut lacy red pair of panties" that you stole aren't her favorite? She might be looking for them.

    She doesn't need a hidden camera; that's new technology. There are plenty of old school ways to find out. She could easily stick a small slip of paper on the side of the drawer that falls out when the drawer is open. This goldfish sitting job might just be a trap.

    In short, stealing panties is not nice, and you may be caught. And, your aunt won't ask you directly. She'll ask your mom (or dad) if they think that you could possibly be the one who's stealing her panties. Think about that.

    I'm sure that I'm not the only one here who started "borrowing" mom's panties. I did. But I very carefully place everything back exactly where they came from.

    So, here's my advice:
    1. Don't steal any more panties from your aunt
    2. If you still have any panties you stole, wash them and put them back; or put them in her dirty laundry to be washed.
    2. Learn how to cover your tracks
    3. If you must borrow, return everything back to where it came from in the same condition,
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

    Gender fluid (adj.) - Describes a person whose gender identity is not fixed. A person who is gender fluid may always feel like a mix of the two traditional genders, but may feel [more] like one gender some days, and [more like] another gender other days.

    Ref: https://www.lgbthealtheducation.org/wp-content/uploads/LGBT-Glossary_March2016.pdf

  13. #13
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    New wearer, wellcome to the forum.
    I would imagine you are heading for some embarrassing times ahead if you keep this up.
    You probably have no idea of the cost of underwear, but the items you describe don't sound like the everyday wear but more like either gifts or special moments items and due to their description I would suspect it would be noticed they are missing.
    Get your own then enjoy.
    How are you going to explain to your Mum when your aunt tells her that her underwear is going missing when you house sit.

  14. #14
    Gold Member Jaylyn's Avatar
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    If your aunt is anything like most women that are slightly older they have a rider for everything. You mentioned that she had several pairs that are the same color or style, she either found a package on sale and bought the whole package or she is fond of that color and style, now you think she won't notice? Every woman has a color she lives and those are the ones she'll probably start looking for when the pair she is wearing gets dirty and she wants another clean pair to wear. I would bet she may have already noticed that her drawers have been tampered with. I'm like the rest here jet buy your own and then if you are ready to purge you can do what you want with them. We all have purged at some point because of guilt. I'm a full time panty wearer now and I love it as I own my own panties. I have a drawer for them as you can see in one of the threads here where many wear them and took pictures of their dressers drawers full of panties.
    Also I would be taken aback by any lingerie you may have seen just because you think your aunt is conservative, what she does in her married life and the way she wants to dress is her business just like its your business to not steal, and be a good house setter. Many on here began from their own moms things ( I did ) by now I own my own dressing attire and makeup, wigs and even heels. Young man I would also like to advise you if you should start dressing get your own things. Then if you get a runner in your hose at least you can discard those and not the ones from a crime scene where you stole them. Remember dressing is fun so enjoy it but do it right by not stealing because then your probably going to get caught.
    Welcome to the site you can learn a lot from here. ( including ethics) lol welcome.

  15. #15
    Member Ariana225's Avatar
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    She will know that the panties are missing. Me and my wife have 100 pairs each and we are always asking each other if one of our pairs accidentally ended up in the others drawer.

    Your aunt probably already knows and doesn’t want to out you. Or is embarassed to confront you about it. But my money is on her knowing.

    I know it’s already been said, but get your own. Amazon is the best place to get your own because the box will say amazon on it and you don’t have to go to the store yourself and take the chance of someone that knows you seeing you.

  16. #16
    Silver Member Micki_Finn's Avatar
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    I’ve gotta agree with everyone else. Stealing is absolutely wrong. It doesn’t matter that she “hasn’t noticed yet”. Remember you are representing an already marginalized and misunderstood community and your actions reflect poorly on all of us.

  17. #17
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    Welcome to the forum. I do agree with the others. Do not steal your aunt's lingerie/panties. The vast majority of women will notice if the lingerie draw has been perused by someone. By your count you have taken at least eight panties. After many years she would be aware if your uncle was messing in her drawers. It is a safe bet she suspects you have been in private areas of the home. If you do not want to be 'outed' this is not the way to keep a secret. Get your own clothes. It is obvious you have a computer. That means you can peruse any website to figure out what you want to buy and where. Make a list and head to the store. You'll be the judge as to how far you want to expand your dressing. Living with your parents is going to be a challenge.

  18. #18
    Senior Member Asew's Avatar
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    Like everyone else said, don't steal. Initially I took clothes from my sister's discarded clothes so I understand the ease of getting clothes from a family member.

    But is is so much better when you get to pick out your own clothes. If I were you, I would focus on getting one outfit you love. This can be your go to outfit. It will let you experience and let you figure out more about this. Figure out your measurements (use a seamstress measuring tape or a piece of string against a straight measuring tape). If you are buying online many sites will give you precise measurements so you can compare them to the ones you took and don't have to worry about how stores have different sizes. If buying at a real store and you don't want to try them on then go for things with some give (a skirt with an elastic waistband or a shirt that is kind of stretchy). Thrift stores are great since they have low prices, are usually sorted by size and have a great variety (and if something doesn't fit you didn't waste much money). Also, measure your feet if you want heels and consider both length and width (in case you have wide feet like I do)

  19. #19
    Yeah Ok like whatever Tracii G's Avatar
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    Welcome
    You don't think she is going to miss 8 pair of panties?
    Lets be honest here the phone charger line no one believes and you had every intention to get into her panty drawer didn't you?
    Stealing is wrong and you know it.If it doesn't belong to you why do you think its OK to steal it?
    Your Aunt is going to know where they went and all the lies in the world won't hide what you did.
    If you still have them put them back if not then you have broken her trust and once thats gone you will never get it back.
    She WILL tell your parents eventually so be ready.
    You are all responsible for your actions so if you get in a huge shit storm its your fault .

    Buy your own panties and clothes if you want to dress.
    Head Executive Chief of the Dept of Redundancy Dept.
    Expert plumpologist

  20. #20
    Junior Member Jasmine Rose's Avatar
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    First, know that you have nothing to be ashamed of in regards to wanting to dress in women's clothing.

    Second, don't be too hard on yourself about the theft. Yes, it was wrong. Yes, you need to get your own panties. However, I think people are focusing too much on the past theft and not enough on what to do in the future.

    A large number of us here got started trying on relatives clothing. Many of those people made the mistake of stealing things instead of just borrowing them. I was one if them. Going forward don't take things that don't belong to you.

    There are many ways to purchase things. Ordering online can be an option. Many stores have a "ship to store" option so you can go pick it up instead of risking it being shipped to your house. This has the additional benefit of also not needing to be seen shopping for panties. If you feel confident enough, you can buy things at places like Walmart where there is a self checkout. If you do have to interact with someone, whether it is a cashier or someone else, just act like what you are doing is normal and people will generally not care.

    There are many tips and tricks available on the forum for how to go about buying things in a way that is unlikely to reveal your secret and also how to best find the right size and style for you.

    Good luck to you and have a great day!

  21. #21
    18 yo Girl <3 Chloe Triss's Avatar
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    Welcome to the forum new wearer.

    Wearing mother's or aunt clothes are pretty much Ohhhhhk but don't steal them.

    Try to cover your tracks, wash put them back, if you like those then try another time when you have the chance to house sit another time. When I was dressing into my aunt drawers, I would take a milky bath and buy some pads for the underwear.

    Washing and ironing is more work so I just put some pads or tissue in the panties and try not to sweat. Just stand in the mirror, sit, looking at myself and then put them back with a little ironing and there you have it, everything is back to normal in the closet.

    Also buy more stuff for yourself. People are more busy and concerned about what they want to buy. It's really ok to just waltz in the store look at panties and stuff CONFIDENTLY cause that will make people ASSUME that you are being ordered to buy or buying for your girlfriend and such. Be in the position where staffs won't come up and ask you what you want. You have to act like you know what you want. If you don't know what you want ask the staffs whether you want to know the sizes of yourself and the clothing, I'm sure that they will tell you and won't judge you directly since you're buying from their store. So good luck crossdressing.
    Chloe Out

  22. #22
    Platinum Member Teresa's Avatar
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    New Wearer,
    One pair may have been OK if you really felt the need but to keep going back after a guilt purge is looking for trouble , your secret isn't going to be secret for long if your aunt outs you by accusing you of stealing her underwear. If you want to come out go and buy your own and maybe buy some for your aunts and give them to her with an apology . It's a good chance she will be OK about it .

    I would suggest you don't go any further with her clothes , it's not very fair on her , you'll have to accept your CDing and move on to getting your own clothing items . Spoiling her clothes possibly damaging them or dare I say soiling them is not good and and will lead to a huge guilt feeling , possibly confusing the whole CDing issue for you .

    I understand what the clothes can mean to a CDer , the issue of stealing them is not the problem it's why you need to wear another woman's clothes is the underlying issue you will have to come to terms with , I admit at times it can be a problem and a confusing one at that .
    The real me ,no going back.

  23. #23
    Call me Pam pamela7's Avatar
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    Quote Originally Posted by New_Wearer View Post
    With regards to a female name, how did you select yours Pamela?
    I needed a name for this forum, and an old work project name just popped up. Once i checked out the etymology it felt perfect.
    https://www.youtube.com/watch?v=dJFyz73MRcg
    I used to believe this, now I'm in the company of many tiggers. A tigger does not wonder why she is a tigger, she just is a tigger.

    thanks to krististeph: tigger = TG'er .. T-I-GG-er

  24. #24
    Silver Member ClosetED's Avatar
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    Welcome to the Forum - it is a great place to learn, share, and get advice.
    Taking that many panties will get noticed. She may choose to not comment, but do not be surprised if you find a note from her next time you house sit. Or mailed to you. Consider your response, such as offering to pay for them.
    If you never hear from her, just work on buying your own. Buying one or two pairs, telling a salesperson that they are for a girlfriend can get you through the situation. Many start off getting sexual release, but often move past that. Ordering stuff online is another way to obtain your own. Pantyhose is often a favorite besides lingerie, and getting one pair at a local store may seem like you were sent to help a family member.
    You are not alone in this, and not likely to have it go away forever, but it does come and go.
    Hugs, Ellen

  25. #25
    I accept myself as is Gillian Gigs's Avatar
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    I would never in a million years think to look for a phone charger in a bedroom dresser drawer! I would think that finding panties and lingerie in a bedroom dresser drawer makes sense. So you found what you were looking for, now stop stealing and buy your own! By my count you have taken 8 pair of panties, I suspect they have been missed by now, unless she has a million pair.
    I like myself, regardless of the packaging that I may come in! It's what is on the inside of the package that counts!

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