Whose lingerie have you tried for the first time?
We all would have started started crossdressing somewhere. I was just curious on knowing Whose lingerie have you tried for the first time?
- Mom/Step Mom
- Sister/Step Sister
- Aunt or other relatives
- Neighbours
- Lady Friend
- Friend of Mom/Sister
- Your own
- Others
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Topics: 0Replies: 0Has thanked: 0 timesBeen thanked: 0 timesOf course as a child I spent the most time in my mother’s underwear drawer, but I have used more women’s bras and panties than I can remember. Some notable ones include:
1. Aunts – my mother has four sisters all of whom are heavily built. Their underwear fit me better than my mother’s and I loved their bigger bras. I remember holding up my mother’s 34a next to one of her sister’s 38dd and being amazed by the difference.
2. Norma – neighbor who I used to housesit for. I had trouble finding more than one bra in her dresser, but she did have great lingerie.
3. Arlene – mother of a friend. I was visiting once and in her laundry room I found bras and panties, so I helped myself.
I both cherish these and regret these and many more memories becuase I understand how hurtful it can be to use somoene else’s clothing like that.
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- Registered On: January 24, 2023Topics: 1Replies: 39Has thanked: 102 timesBeen thanked: 132 times
I started with bralette type of tops and them I bought on a shop and after that step by step into bras. Total change was when I discovered Victoria’s Secret’s 38B and XL fit excellently.
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- Registered On: February 19, 2022Topics: 2Replies: 30Has thanked: 34 timesBeen thanked: 132 times
I was attracted to feeling feminine from a young age and I think it came from my mother’s beauty, style of dress and sweet smell of her perfume. My siblings and I were all expected to do work around the home as my mother worked as a PA to the CEO of a metal works and she wore the most femine attire and looked amazing each day. Having to fold the washing I got to feel the softness of her lingerie, nylon stockings/pantyhose and dresses and I eventually had to feel and wear these things in private. As I matured this became quite sexually stimulating too and I could not resist the temptation and opportunity whenever it presented. This progressed to wearing my sister’s lingerie, her best friend’s, and her aunt and mother’s fine things. A beautiful, curvy neighbour wore the most fine, full cut briefs which she displayed on their clothes line most days and, while I never got to wear them, I am sure that is why I adore wèaring them to this day. I often fantasised about seeing her wearing them with a matching bra and pantyhose. She wore tight, fitted clothes and you could see her lingerie lines and waistband of her pantyhose, high on her waist and the seam running down her tummy. She really caught my attention in my early teenage years as she also wore lots of makeup and I thought she was the most feminine woman. I have a lot to thank her and my mother for in my tastes in women’s attire.
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Registered On: February 20, 2018Topics: 4Replies: 16Has thanked: 130 timesBeen thanked: 149 timesThanks for a detailed write up Inga. It did bring back my experiences to my memory. In fact, showing the lingerie lines through the clothes is most sensual thing for me and that was one of key inspirations for my journey. I follow the same even today!! Thanks for sharing your experience!!
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- Registered On: September 27, 2016Topics: 4Replies: 299Has thanked: 207 timesBeen thanked: 1346 times
Beautifully written. Your memories brought back my own and that wonderful time of youthful discovery of not only the sensuous nature of lingerie, but also the sexual awakening that eventually followed and, for me at least, endured.
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- Registered On: February 19, 2022Topics: 2Replies: 30Has thanked: 34 timesBeen thanked: 132 times
Thanks Kimmie. I am pleased that my recollections resonated with you. These were very formative times that we cherish and I think create the strong feminibe urges, sensitivity and sexual freedom we enjoy in our lives. My wife and I have become much more connected once we appreciate the feminine traits we share. Life is good if we choose to embrace who we are.
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When I was in my early to mid teens I baby sat for a couple that were on my paper route. One time I noticed a pair of pink silk bikini panties and had this urge to try them on….by the time I stopped baby sitting for them I had tried on several of her bras, panties, garterbelt&stockings and silk nighties.
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- Registered On: February 19, 2021Topics: 1Replies: 72Has thanked: 1696 timesBeen thanked: 414 times
My first time was when I was 11 or 12 and I tried on one of my mom’s bras I found in the clothes hamper. After that first time, I would regularly check the hamper to see if there were any of her bras I could wear. One day she caught me trying one on, but didn’t make a big deal of it. I of course was hugely embarrassed, but not enough to stop.
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Always had an interest since I had three older sisters and a mom and one bathroom. But it was my grandmothers panties and silk nightie. I was staying at her house and came across them while putting sesay clothes. I was 12 or thirteen. I slept in then but then had to handwash them and return before anyone caught on.
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My mums, I must have been about 13 when I was old enough to be left in my own, I used watch her dress through her half open bedroom door, when she had gone out I would go through her lingerie drawer and put on her pink corsellettes and nylons and feel wonderful, I did this till I was about 20 until I could but my own lingerie, I don’t know if she knew I was trying them on, but she knew i was going though her lingerie because told me to stop going into her clothes drawers, but I never stopped I couldn’t help myself, this was in 1961 and still crossdressing in 2021
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- Registered On: April 20, 2019Topics: 68Replies: 254Has thanked: 5520 timesBeen thanked: 2140 times
I first remember playing with other girls and we all put on skirts and that was such a thrill, then I started sneaking in to my mothers drawers to get her panties and stockings. That went on for several teenage years. Next I remember visiting my wife’s friends house while she was away and trying on all the lingerie. Then a long dry spell until I started buying panties and wearing them about 10 years ago. Two years ago Jennifer came on full force. Good thing my SO is supportive.
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the very first item of girly clothes I wore was a very pretty lace trimmed half slip of my Moms.
I was 5 and just Loved wearing it, to a 5 yr. old, it fit just right.
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- Registered On: September 26, 2020Topics: 5Replies: 58Has thanked: 21 timesBeen thanked: 307 times
I think the first time I tried on any article of women’s underclothes was when I tried on a pair of my mom’s pantyhose in either high school or the early college years, when I was still living at home. Either way, it was too small for me and I ripped it a little trying to put it on so I ended up panicking and throwing it away! I don’t think she ever noticed… but then again, she only really wore pantyhose to church or to fancy dress-up type occasions and neither of those were really part of her life after she got divorced.
Aside from that, the first thing I ever wore was a pair of leopard print panties that someone abandoned in the laundry room of an apartment I had in college. I guess that would count as either “someone else’s” or “your own,” depending on just how abandoned they were. 😅
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- Registered On: October 3, 2019Topics: 14Replies: 174Has thanked: 624 timesBeen thanked: 1291 times
Yes. I wore my Mom’s lingerie first in the my teens. We were the same size. It was a huge thrill to sneak into her room and borrow her things. Like others I ended up wearing all her clothes. It was so exciting because it was new and fun and sexual. I so love those early years of exploring my feminine side.
hugsRosiebeth.
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About 8 or 9 I used to sneak my sisters panties into my bed, hide them under the mattress, then pull them on at night. The feeling was amazing! Later her bras, and in my early teens my mum’s tights, bras and petticoats.
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I was very attracted to a couple of my friend’s mothers and it was an incredible thrill to wear their panties, hose and slips. I felt very connected to them that way.
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Like most of us ‘girls’ started with mum’s and a few times with my sister’s and also the girl next door ,I would dress in their girdles ,panties ,stockings and slips but one thing I never tried on were their bras ,now of course the bra is the number one item ,I wouldn’t dress without a bra .
Michelle xx13 users thanked author for this post.
- Registered On: January 2, 2021Topics: 13Replies: 963Has thanked: 1492 timesBeen thanked: 3303 times
Suchi Sweetness…
A little somewhat bizarre story…
When I divorced my Swedish wife I began to live alone in a small apartment in a small village. So far, so good. The village had a container dump on the edge of the village from which I was able to furnish my apartment with antique furniture!
So called ‘dumpster diving’ was quite fun actually as I rescued all sorts of things to on sell such as a two hundred book library of antique books in Latin.
One such visit to the dump netted me a suitcase of antique lingerie!!
Oh la la… corsets, silk stockings, panty girdles, brassieres et al.
Can you imagine the fun I had sorting through all of these lovely undergarments? Well, one thing led to another and of course… I had to try on some… no, all of these items! I was thinner then.Well… from then on I was hooked on ‘underdressing’.
Pretty Pantied Polly xxx
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it was definitely my mom’s, she caught me while I was going through her lingerie drawer had already had the bottom half of a two piece canary yellow baby doll on, instead of Flipping Out She calmly walked over and put the top half on my bare chest. it was at that moment about trying on her clothes that started my lifelong journey.
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- Registered On: February 26, 2020Topics: 6Replies: 198Has thanked: 1112 timesBeen thanked: 1244 times
Staci – You are so lucky to have had such an understanding mother. Did she continue to help you dress in her clothes after that or get you your own clothes to wear?
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Emily, she did start buying me my clothes which was very special as each time that we would go out shopping together she always presented me as her daughter but when I was younger that was easier to pull off as I got older it became much more of a challenge.
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She did …. she kept on started buying me training bras and matching panties and we would have a lot of fun dressing together
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- Registered On: October 13, 2015Topics: 6Replies: 865Has thanked: 4095 timesBeen thanked: 2730 times
Like most, i guess I was about ten, I put on my mother’s girdle with garters… some how I was able to fasten her sheer nylons to the garters .. I also found her satin slip… yup …. I have been hooked ever since… I have come a long way since that “first time”. Thanks for listening….Leonara
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- Registered On: December 20, 2016Topics: 55Replies: 509Has thanked: 1814 timesBeen thanked: 2025 times
My very first time was when I was in the 3rd grade, and I was about 9 or 10 years old.
I was digging in my moms dresser for change to steal, so I could buy candy at the candy store on my way to school. Mom always hide her spare change there. While I was digging I saw these super soft satin underwear. I was drawn to them like steel is to a magnet.
At that very moment I had to grab them and run to hide into the bathroom to try them on. I never took them off and went to school wearing them. From then on I kept on wearing till I hit middle school and the urge just seemed to disappear.
It reappeared shorty after high school
Hippie
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When I was 11, a neighbor gave me a pair of purple panties. I would wear them under my blue jeans and at night. I left them somewhere and my mother found them and took them away. I was given a long talking to filled with shame. I didn’t wear anything nice for another 10 years. I wanted to, but fear of another talk was too great.
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- Registered On: January 23, 2019Topics: 9Replies: 183Has thanked: 73 timesBeen thanked: 769 times
I guess I was about 6-7. At our beach club we shared a changing room / locker with friends who had a daughter about my age. One day I was getting changed and her one piece suit was hanging there. I wondered what it was like and pulled it on, it just felt so right then and there! I loved the way it felt and how I looked, just sad I had to take it off and carefully hang it back up. Needless to say that summer I got changed a lot of times.
S
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- Registered On: October 17, 2017Topics: 5Replies: 12Has thanked: 102 timesBeen thanked: 155 times
A little bit funny now some 52 years later but very unnerving at the time. Had tried on a few of my Mother’s undergarments, but only a pair of panties a time or too. While she ran out to run some errands I figured I had time to go further and try on more things. I put on a bra, panties, hose and had just pulled up one of her girdles when I heard our car pull into the drive. Assuming she had forgot something I ran into my room and threw on a t-shirt and pants. She came into my room just as I was dressed and told me she forgot she had to meet my aunt who lived in the next town. She said get my shoes on and grab a jacket, we had to go, cause she was late. No time to change so I put on my shoes and my jacket. As we left my mind was in a whirl. So I ended up spending the day fully underdressed. While being very nerve-racking, it was still a glorious day once I survived it. Always wondered if my Mom or Aunt suspected anything.
Sincerely Sara
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- Registered On: November 30, 2019Topics: 29Replies: 4897Has thanked: 72103 timesBeen thanked: 17180 times
Hi Suchi nice to meet you and was moms lingere to try on as a younger sister clothes were a little small but moms were a bit bigger as about 8 or so in age but fun never the less as mom cought me a few times in her undies we had a little talk and as i had to baby sit little sister most of the time so dad and older brother would not find out she would buy sister a few things for some funny reason would be a bit large for her and about my size ha ha so it was game on to speak was looked after by mom so we didnt get caught so little Stephanie and sister would have more girly time together never out side the home just in bedroom as us girls played ..
Stephanie Bass
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It was definitely my mom’s bra and panties I remember the color it was light blu abd and lace bra and lace trim panties around the leg area she always had gourgous lingerie I learned so much from her growing up and how she let me be a girl on weekends till I got older
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My fall down the rabbit hole was my aunt’s bra. I hooked it, slid my arms under the straps and places some socks in the cups. Putting on a shirt and seeing boobs thereafter just insured it. When puberty hit and I became a teen, I would wear my moms bras and panties when no one was at the house and occasionally, my sister’s.
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Mainly mom’s, sister’s and grandmothers. Grandmother solely because she had a lot of cool shapewear, which my mom and sister did not.
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- Registered On: December 22, 2020Topics: 7Replies: 162Has thanked: 673 timesBeen thanked: 691 times
When I was in my early 20s, my roommates, both women, dressed me in their clothes and took me clubbing a few times. From that point on, I would borrow their lingerie or dress up with them and go out. We had lots of fun (inside as well) and had a wonderful two years together. I met a woman who did not approve, but I wore her lingerie as well without her knowledge. Apart from a few short women I have dated (I am quite tall), I have worn panties (and occasionally bras) of every woman I have dated. It has been wonderful! As I get older, I am getting bolder, so enjoying it even more!
hugs,
Ginny
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Started at 11 with my sisters underwear… just bra and panties. Evolved from their, I discovered my mum had some stockings and suspenders so I used to mix and match. My mum had panty girdles and underskirts that I used to adore so more often than not I would dress in her bra, knickers, tights, panty girdle and underskirt… I didn’t start dressing fully until I was 16 and my sisters wardrobe was a crossdressers treasure chest. I never wore my mums outer clothes as they didn’t fit.
At the same time I started buying my own lingerie so my use of their dropped off. When I married I did wear my wife’s outer clothes but had my own vast selection of underwear
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La ropa de mi mama sus medias y despues la de mis ermanas
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Just a poll to see Whose lingerie have you tried for the first time?
When I was 13 I used my sister’s panties and clothes in my twenties when I was married I flat out wore my wife’s lingerie and loved it but not until my mid thirties did I wear it with my wife we had a blast she would make love to me no matter what I was wearing I think this turned her on as mach as me was some of the best sex we had💋💋💋
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- Registered On: October 6, 2020Topics: 91Replies: 125Has thanked: 1180 timesBeen thanked: 2086 times
A girlfriends I was in my early 20s my GF at the time lived in a converted basement and her mom lived upstairs. I was always trying to get my GF to dress sexy for me and she never would. One day I bought her a black thong teddy with garter and sheer stockings. She threw it at me and said if I like it so much I should put it in I said by god I will. I came out the bathroom and said look how sexy I am jut as i got around the corner the mom was coming down stairs. I jumped into the bathroom and put my guy clothes on over the lingerie. The mom asked if we want to go eat her treat the girlfriend said yea we love to go. Her mom said good looks like you kids are already dressed lets go. After we got done eating I was thinking thank god i can change the GF chimed up lets go see a movie and the mom agreed. When the night was finally over and we mad it back home.The GF gave me a kiss and said she was tired and going to bed.The next day I handed the lingerie to her she asked how did I get it did I take it home? Thats when i told her about wearing it under my clothes all night. She started laffing really hard and said she forgot I had it on.
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I started with my sisters, but quickly moved on to my mother’s as well. As a teen and into college I tried on or borrowed stuff from aunts, cousins, friends mom’s and sisters, neighbors, friends of my sisters, female friends, basically whoever’s stuff I had a chance to try. In hindsight not teh most considerate thing to do but at the time it was quite the rush both seeing what different types of lingerie people had and getting the chance to try it.
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- Registered On: October 6, 2019Topics: 8Replies: 107Has thanked: 783 timesBeen thanked: 508 times
Same here, until I got married when my wife (after learning of my proclivity) allowed me to wear some of her panties.
I soon realised that panties that looked beautiful on her did not fit me too well and that I’d have to get my own.
Fortunately, she was a lingerie lover and a devoted ally people of alternative sexualities ( for want of a better expression).
We spent many thrilling hours in department stores and at markets browsing and selecting panties for ME!
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- Registered On: December 24, 2020Topics: 9Replies: 79Has thanked: 204 timesBeen thanked: 510 times
Mine was at around 10 y/o, I don’t have any sister and we lived quite a few way from any of our extended family so, it was my mom’s, I always loved feeling of the fabric when I was younger, but the first time I tired them on was at the age of 10, and I can remember the anxiety of getting caught just melted away and I felt more like me then I had in the first 10 years of my life.
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The first time was when i was about 8 or 9 years old, it was my older sisters lingerie i tried on first she was in her mid teens about 5 or 6 years older than me,
I was off school a lot with one childhood illness after another so i was at home alone and had nothing to do,
Well one thing led to another and i found some of her lingerie in the washing basket and my curiosity got the better of me,
I had to put some socks in the cups to pad them out to give me more of a womanly shape,
Now if i buy a bra with an A cup i don’t need any padding i sometimes wish i had a bigger bust but you never know what will happen in the future x
Hugs Rozalyne x
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- Registered On: February 11, 2019Topics: 24Replies: 1704Has thanked: 5251 timesBeen thanked: 5713 times
I started about 12 with my Mom’s for years, as I had no close aunts or any sisters at all. I have read stories of how some with slightly older sisters would borrow theirs, which would have amazing as well. That said I certainly enjoyed borrowing my Mom’s for a few years till the family situation changed and it made it nigh impossible to borrow them and dress up a bit.
Then later when the urge hit again I borrowed my wife’s, with her permission too. Though at times I had my own, as one Christmas I bought some sexy things for my wife, but they didn’t fit her so I kept them for me.
Next step was when my wife told me I should have my own bras, now I have so many more than my wife!
Amy
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My first were my mum’s, I was around 12. I had been touching her lingerie whenever I came across them in laundry basket in bathroom Fromm very early, I was nearly 12 first time I ventured to actually wear some, it felt wonderful, I was hooked. I started going thru her lingerie drawers and finding some beautiful silky slips and knickers. She also wore corsets and girdles,which I still have a fetish for. She did discover I was wearing her things,but that’s another story 💋💋
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first, mom.
second, cousin then aunts.
third was sister.
finally, my own.Jennifer
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- Registered On: December 15, 2020Topics: 0Replies: 48Has thanked: 32 timesBeen thanked: 180 times
Strangely, the first time I tried lingerie it belonged to my Mother in Law. I was married at an early age to a nurse and in order to save money for a place of our own she took a job abroad while I moved in with her mother a dominant but elegant woman. Gradually as I took over a greater share of the household duties I could not resist trying on some of her exquisite lingerie after having laundered it.She discovered my developing fetish and even encouraged it. My wife found a new, female, partner while abroad. The rest is history
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- Registered On: August 10, 2019Topics: 7Replies: 306Has thanked: 1772 timesBeen thanked: 1670 times
Sister’s while I was a young teen. Maybe 12 or 13? Not sure.
Primarily pantyhose 🙂
She did not know 😉
Used to read her Cosmo mags too, trying to pick up tips on how to be sexier 😉
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- Registered On: November 10, 2020Topics: 1Replies: 15Has thanked: 160 timesBeen thanked: 142 times
I’m pretty sure that in my teen years, when I was first learning about Stephani, there weren’t many women in my life that I hadn’t tried on their clothes! I was a regular “panty bandit” lol. I knew from the first Vanity Fair panties of my Grandmothers that I was hooked! My favorite was when I would be wearing the panties of who I was talking to, what a rush!
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I started wearing my mom’s lingerie and panties round age 12. Once I started I couldn’t stop, I would love when I had the house to myself and I could dress in a full teddy with garters and stockings. She had so many panties and sexy lingerie. I’d be able to take a couple pairs for good and hide them in my room in case I couldn’t get a pair from her room.
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Same as most it seems !! My mums lingerie was my first step , I just couldn’t get enough .whenever I thought I had the house to myself I’d run upstairs and find what I could
sonia xxx
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- Registered On: December 10, 2019Topics: 1Replies: 92Has thanked: 2180 timesBeen thanked: 500 times
As a young boy I recognized that my mom and girls didn’t wear what I had to wear but I so loved pretty girly things and wanted to wear what girls wore. Anyways, being a boy and told girls things were for girls and boys were for boys I resisted the temptation to try on girly things until I was 11 and there was a lovely silky pair of mom’s panties on the clotheshorse and…well…my crossdressing began and I have so enjoyed my girly fem side ever since. From that day on I was constantly looking and feeling into the clothes hamper and mom’s panty drawer and I’m sure she knew but we never chatted about it. I also sneaked into my mom’s sisters panty and slip drawers too years later…my auntie had the most lovely silky slips and panties and the prettiest nighties…I just could not help myself!!! As my crossdressing years passed on I got up the courage to buy my own panties and pretty things, sometimes from department and women’s clothing stores but my favorite place to shop for lingerie and dresses has become Thrift Stores. It just feels so extra girly knowing I’m wearing things a woman wore before me.
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I had many pleasurable hours dressed in a former teachers lingerie while babysitting for her.
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My moms from the hamper in the bathroom while I was filling the tub. Never took from my mothers drawer as she would have know because it so neat. On the other hand my older sisters lingerie drawer was a mess and she would never know, I was careful not to dirty them but if it did happen I hand washed them and then air dried them and replaced them the next day, never got caught doing it.
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I had the same experience my moms in the hamper. At the time women would also wear rubber griddles which were not easy to get on even though I was in grammar school and much smaller. Thanks for the memory. Joanie
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- Registered On: October 1, 2020Topics: 10Replies: 139Has thanked: 441 timesBeen thanked: 908 times
My own. When I was growing up, I wanted to wear skirts more then any other female clothing. It was only when I was in my 20’s that I started to realize that I probably should start looking at other items to complete the look, so I ordered my first panties online and immediately fell in love with them… so then I started to order more and more, and other lingerie.
…And now I’m hooked! 😜
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- Registered On: October 11, 2020Topics: 29Replies: 1007Has thanked: 5926 timesBeen thanked: 4273 times
My Aunts! She had the most awesome selection of heels, panties, stockings, garters, corsets. Nearly blew my little teenage head off when I found them while babysitting my cousin. And she had silk bed sheets! Some of my fondest memories as a teen.
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From the age of 9/10 it was always mother’s nightdresses and slips when she was out. I always loved the feel of them, still do today 50 years later.
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- Registered On: February 26, 2020Topics: 6Replies: 198Has thanked: 1112 timesBeen thanked: 1244 times
My first experience was playing dress up with my sister. She put me in a cute little dress, a pair of her panties, and a pair of her sandals. We were having a blast playing sisters until my mother caught us and told us to never do that again. Something stuck with me though and a year or so later I saw a pair of my sister’s baby blue nylon panties in our shared bathroom. I had an incredible urge to try them on. Once I slipped them up my legs, the feeling was unreal. From that point on, I knew that had had to wear nylon panties as often as possible. I quickly added slips, baby doll nighties, and pantyhose to my secret dress-up times as well. I continued to “borrow” my sister’s panties and other lingerie until I was old enough (and brave enough) to purchase my own.
Such great memories!
Hugs,
Emily
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