When did you start wearing ladies underwear or clothing? What were some of the first things you wore?
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As a woman I have always but my husband has been enjoying knickers and stockings and suspenders for about 6 years
His first items were my older knickers but we soon started to buy lingerie for him 
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That’s the best way to go about it. Keeps the spice alive.
Do you go together to buy it or do you suprise him.
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I’ve written this before but it was down to a Rocky Horror party bought a black basque black underwear stockings and ankle boots . Pre the party tried it one and it triggered some thing.
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@ROGER_THE_DODGER
We generally buy lingerie together but I do buy lingerie for him for Christmas presents 
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A long time ago (20+ years) wore oh’s knickers during sex. Only recently has this become an important part of our sex life…my collection grows constantly 
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Back in my late teens,had wonderful access to a friends lingerie shop and have pretty much indulged in lacy silky loveliness to some extent ever since.All my serious partners etc in life have also been fine with it which has been a big bonus.These days i wear nothing else but lingerie as well as lots of ladies normal outer clothing too where possible.Letting my feminine side out like this feels awesome.
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@Pogo69
My first knickers were given to me by my first ever girlfriend as she knew I just wanted to be in them - I still got them after 40 years (I’m 53 now)
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First started trying on feminie underwear when I was in early teens, along with other clothes like blouses and skirts.
These were all clothes belonging to a slightly older cousin we visited every month.
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After 45 years of having this desire I finally outed myself to my OH in September this year and then acquired my first two pairs of new knicks soon after…
Check out the pic in the gallery: https://lovehoneyforum.com/t/lingerie-photo-uploads/257652/2213
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Errmm I bet it was my really early teens. I remember being obsessed with wrestling and during the attitude era, a lot of the female wrestlers would show off their thongs. Other than being completely turned on by that, I was also very curious what they’d feel like. Finally got to try one on and I loved it!
Fast forward a through my teen years I must’ve had a stash of 50+ female thongs. I remember having to hand wash them in the sink and hide wearing them under my boxers. Completely different now I’m in my early 30’s. Apart from every now and then when my wife tells me to wear her thong, I wear male thongs everyday. I wouldn’t say I give everyone a whale tail but I don’t hide that I wear thongs.
Over the last 6 or 7 years I have crossdressed more and more which I absolutely love doing. I’ve a little collection of PVC outfits and x3 pair of thigh high boots (hard to find with big feet). Only dared go outside whilst crossdressed a couple times and that’s always been with the safety of fancy dress. Rocky Horror was incredible!!! Can’t recommend that enough!!!
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hey am Claire bi crossdress edited by mod don’t ask me how or why it just felt right am now 48 still love to crossdress would love to hear your thoughts 
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I jokingly wore womens underwear many years ago to get laughs out of friends, which worked. Basic kmart stuff.
2023 though i have started wearing it for my own interest as I have learned im genderfluid leaning towards being a woman.
So I have started wearing random sexy lingirie you find on lovehoney that isnt crotchless and it feels so good 
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@satinclairexd can you remember who the clothes belonged to? I got in to it edited by trying on my older cousins bras and knickers, then her outer wear too. edited I would then wear my mom’s clothes and started with makeup then too. Now 55 and still love it!
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Like you, I started edited guiltily raiding my mum’s undies drawer. I have no idea what triggered it (but I’m sure a therapist may have some suggestions) but like you say, it just felt right. Many years on I’m still doing it but have my own collection of underwear and lingerie now.
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About 5 years ago, became super addicted to basques and Lovehoney sure deliver on that front.
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I feel so relaxed,happy and sexy in lingerie.My daily life feels wonderful dressed in knickers,bra and stockings.When i get home and put on a dress or skirt and become “Penelope” i feel complete.When i get ready for bed and wear a luxury satin or silk nightie the feeling is absolutely incredible.I still love and fancy my wife very very much and i am always in some sort of state of horniness which she loves.At first she was apprehensive but now she realises this is not only harmless but has a huge positive impact on our marriage.
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Recently with a new lady friend and with only one problem…I prefer women’s panties over any other underwear and be leave me I’ve tried them all …she appreciates me being well groomed and clean shaven but how do I get her to understand and accept my choice of underwear…Ishe is the first I ever seen that I sorta feel might have issues with that…
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Wear tame knickers (not too frilly) and I’m sure she will be fine - just make sure her knickers are better than yours
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I’m sorry but I don’t have a clue what a knicker is 