First time in heels. Tell me about it

This topic contains 39 replies, has 35 voices, and was last updated by  Anonymous 5 months, 3 weeks ago.

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  • #113854
     Anonymous
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    hi ladies and guys; I brought my first pair heels yerestday. they black platform sandals, with 4.5 block hees with a 1.5 inch platform. I tried them on the the payless store, the sale lady was so nice to me. she even pick out a couple other pairs to try on. its was so excited for me, and lady understood me. I even asked how they look on me, then she there a mirror over here, see how they look on you. she was friendly, I was so surprised she was so nice to me. love mark

  • #112510
     Anonymous
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    I bought and wore my first pair of heels today. 4 inch stilettos and omg they feel and look amazing. Walking is going to need some practice though. Yes that’s them in my profile picture. Xx

  • #112408
     georgia gaetz 
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    The first pair I got was 3 ” heels and when I put them on I was in heaven.

  • #111955
     Jamie Noir 
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    Oh man. I was donning heels, stocking and ddresses since about 10 or 11. Our basement had tons of old clothes for me to pplay in. Some my moms and some my sister’s.

    SShe had stuff left over from the lates 60s that included wigs and shiny stockings. I was a mess.

  • #106268
     Anonymous
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    Ive worn heels for some time now,quite comfortably,just like wearing and walking in any shoes “confidently”..However recalling of my experience The first time I put on a pair of High heels i recall fondly : it was purely exhilarating,exciting to finally see my own feet in a beautiful pair of feminine shoes,I enjoyed my reflection and tried to match them to a few outfits..oh the mistakes of bad fashion choices I had back then..such a lifelong trial…I knew back then,it wouldn’t be long before I’d have to try walking in high heels too, my first attempt looked like I had just dismounted from a day spent on a saddle riding a horse crossed with weak knees/ankles and definately no helpful advice-long before youtube and online tutorials, even before Windows was a thing..

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  • #105071
     Sassy Stacy 
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    My first time was when I snuck into my elder sister’s heels when everyone except myself was out of the house. I had wanted to try it for weeks before I got the opportunity. Since that time I would always take the opportunity to try them when I could 🙂

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  • #104584
     Roberta Hall 
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    I wear high heels all the time and if you wear them all the time you get used to walking around in them. I love wearing a bra and panties when I get home.  I throw on a pair of Jean’s and a shirt and put my high heels on and do my house work and everything else well I am dressed.

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  • #101316
     Margarita Gaitan 
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    First time wearing heels was while still living in Colombia, they were a sister’s kitten heels—it was great until a relative’s voice yelled “Miguelito!”, turned around and was knocked to the ground told “Gaitan males don’t wear female clothes”, shortly afterwards moved into a seedy whorehouse (not unlike the family home). It was a bittersweet experience.

  • #95140
     Anonymous
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    The first time I wore heels, I was early teens with an older sister with the same size feet. She had a pair of 5inch slingbacks which looked amazing. I had  a couple evenings a week where I was home alone so I snuck into her room and slipped those shoes on. I nearly broke my neck first time but they felt wonderful! A few weeks sneaking practise on them here and there and I was owning that walk! Unfortunately I kept growing and it wasn’t long before it wasn’t worth even attempting to wear them 🙁 it took me me maybe 5 years after that to get my own pair that fit me, simple 3 inch courts but first time I put them on I was walking confidently in minutes. Had so many pairs of shoes over the years (along with clothes)but purging won until now, only have a couple pairs for now, along with some pretty clothes to go with them, slowly rebuilding that collection!

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  • #95086
     Edie Majeski 
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    My first heel were only two to three inches and usually wide heels. Buying a taller or a spike heel in my size was simply impossible in my early feminine days. When I finally was able to buy a five inch spike heels, I was thrilled and then nearly fell flat on the floor trying to walk across a carpet. They did encourage me to finally learn how to walk like a woman.

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  • #94620
     Roberta Hall 
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    Heels love them.  I have a  pair of 5 inch heels and I wear them all the time.  I wear them with my pants and my long lengthwise shirts . I look so sexy and love the way I look wearing my clothes and my lingerie with my heels.

  • #92623
     Maria Troup 
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    It wasn’t the first time I War heels it was the second time walking up a steep hill now that was hard

  • #92619
     Steven Andrews 
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    Like most I needed a larger size. Size 11 womens. since your don’t find that all too often where I live I was delighted when I scored a near new set of of 11M pumps at Goodwill. They fit perfect and wow did they make me feel great. Suddenly I felt an extra boost of Femmey Confidence  and Empowerment. And wow did they make my legs look great. Wifey is jealous of my legs now.

    That extra Femmey Confidence boost is what we all need. Amazing feeling I’ve never felt in the Man world.  So I always get a “boost” when I wear heels now and a nice little reminder of those good feelings.   🙂

  • #92336
     Kelly Terry 
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    Don’t remember first time(s) I did wear heels but I do remember that in high school it was a girl 2 grades up that did wear black pumps most days and I tried to get a peak of them all the time and wished I could wear them.
    Now I’m at 4″ or higher all the time (well, when I can have something that shows that is) and feel so strange whenever I have take them off, feels strange to walk heel less.

  • #85666
     Stephanie Flowers 
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    Heels  what an emotional experience . Dressing in whole or in part has been a daunting task  over the past year finally came the day when I actually ordered some heels. That day I fully dressed and on came the heels and omg! ! Staring into to mirror ,it became apparent an unexpected feel came over me. An xhilaration from my head down to my pretty toes. That first walk around that house, the clacking of heels up and down the hardwood floors ,the swinging of my dress and a twirl or two. It was heaven, a moment that I realized I’m feeling and now looking the person I always dreamed of becoming. 3 more pairs later, open toe ,strappy and a  beautiful 4 inch reds, never felt so feminine and in time I’m looking forward to the day to really put the mileage on them when the time to venture out. Love my shoes as now it seems to make me feel more of a woman  I’ll never thought I could never have  ever been . 🌹

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  • #85649
     Sara Marie Franklin (SMF) 
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    Tried my moms on when I was young and could fit in them, I loved them.  But my wife’s were way to small she is a size 6 1/2 and I’m a size 10.  LOL  But the first time I got a pair I could wear as an adult was my friends wife threw out a pair of heels that were my size.  I grabbed them with out them knowing and I wore them cute sling backs about 3 inch heel not a great color kind of gray green but I felt in heaven wearing them and did until I broke the heel.  Since I have bought many pairs and love them all even the 5-6 inch heels though hard on the feet.  : )

    Now when ever I go out I do not feel very feminine unless I am wearing a pair of heels or wedges.  Though I have some womens flats and heelless boots I almost feel not fully dressed when wearing them.

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  • #84399
     Sa·man·tha 
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    I love heels, the way they make me feel, what they do to my posture, what they do to my walk.  Love it.  I’ve always had really good balance and some grace about the way I move, so heels came easily to me.  Hell I’ve ran in them no problem although not like long distance or anything.

    As an aside, my first experience with heels was when I was 8 or 9.  I wore a pair of my grandma’s, she had about a hundred pair.  We used to call her “Imelda Marcos”.  She wasn’t home but grandpa was.  It disturbed him to see me doing this and he began trying to dissuade me in his characteristic gentle and friendly manner.  I loved Grandpa dearly but seeing him get so disturbed made it even more fun.

  • #84166
     Katie Thomas 
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    The first time I wore my wedge sandals was the best.  Had my toes painted red, black skirt and tan pantyhose, I was in heaven.

  • #84142
     Tanya 
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    I used to try to squeeze into my wife’s heels but it never worked.  A few years ago I brought my own heels in my size. When I put them on it was awesome, everything just  seemed to come together. I don’t think I ever dress now without wearing heels.

  • #83579
     Paulette Gibson 
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    I tried many times to wear my ex-wife’s stiletto heels. Even though I knew they were too small. I wanted very much to know what it felt like. And what it looked like to have your leg muscles made taut and accentuated by heels.

    When I finally figured out the man to woman transition in sizes and bought the first pair of heels that fit me! My God, what a feeling that was. I nearly broke an ankle walking about the house for so long wearing them. But I couldn’t get over how they made my legs look and feel, especially wearing hose. I didn’t want to take them off. Even now my preferred heel is a 4″ spike. I wish I could spend as much time wearing 6″ but just can’t master it yet.

    But I’ll keep trying.

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  • #83240
     Taryn Michon 
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    I finally figured out my size after buying a pair of black suade pumps; I had a difficult time at first but I got the hang of walking in them after about a week or two.

  • #82111
     Paulette Gibson 
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    I don’t remember the first heels I wore – probably too small and too uncomfortable anyway! But I remember my first pair of 4″ stilettos with stappy toe and ankle strap that really fit! I’ll never forget the feeling of my feet after I had walked to the bus stop and back for the very first time. Throbbing and aching and oh so proud! I still love those heels, especially after wearing them for the day downtown and kicking them off when I get home. You have to love wearing your favorite heels.

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  • #81617
     tricha polling 
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    my first heels arrived today, 3″ pumps and thank god I didn’t get anything taller, they feel great though, I have about an hour to try to break them in, and I will have to narrow my toe nails as I can feel my toes squishing together and the nails are cutting into each other

  • #81547
     Jennifer Schmidt 
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    the first time I wore heels out I went to the grocery store and I had a pair of   jeans on and they were mule heels I also was wearing pantyhose as I walked up the aisle I somehow slipped and fell and my one heel came of luckly no one saw me and I got up off the floor and checked out and got in my car that was some day I will tell you and no i didn’t get hurt and did have fun

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  • #81525
     Holly G 
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    I will never forget how excited I was to FINALLY find heels in my size!  I am 6’2″ and have size 12 mens shoes, so finding heels that I can smash my feet into was a major challenge.  One day at Ross, I found a pair a black strappy 4″ stiletto platform heels in size 12!  The open front meant that they would fit my clown feet!  I rushed home (after putting them on in the car…I just couldn’t wait!) and when no one was home, put them on to strut around on the hardwood floors…OMG Heaven!! Yes I was and at times still are wobbly in them because I do not get too much practice time these days, but suddenly my super long guy “chicken legs” looked like sexy runway model legs with opaque tights, a short tight black skirt, and platform stilettos…to this day they are still my favorite shoes!

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  • #81524
     Angela 
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    Thank you for sharing Stella!

    My experience has been heels are the only shoes I will wear while en femme. I only have 5″ pumps and boots at this point and LOVE the look and feeling of walking in them both!! I plan on buying a shorter pair to “fit” in better while in public, but have no problem going anywhere in my 5″ heels. Makes me feel more like the woman I truly am!!!

    Hugs,

    Angela

    Angela

  • #81457
     Julie Marie Dosier 
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    It wasn’t my first time in heels by a long shot, but I just had to let you ladies know about the most comfortable pair of high heels I have ever worn. Tonight on my usual en femme walk I wore my new MIA Debra booties with three-inch wedge heels. They have just the right amount of cushioning, the foot shape is just right (not too pinched), and the heel to toe slope and grippy soles made the three-mile stroll exquisite. Most of my “walking” heels are comfortable, but these take comfort to a new level. And I got them for just 20 bucks on Ebay!

  • #80903
     Patty Phose 
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    The first rime I wore heels they were a sexy stiletto I just had to have to dress for a Halloween Party. When I put them on it was horrible. I could barely stand in them and my feet hurt. Forget about walking. When I saw my legs in them though with my short dress and shiny pantyhose, I was amazed at how beautiful and sexy my legs looked. I knew I was going to wear them no matter what.

    I wore them in the house all the time. I had to sometimes support myself as I walked around. After a few days I could get around in them pretty good but my feet still hurt. Everyday though I walked better and my feet hurt less. After a couple of weeks they were very comfortable and natural. Then I would wear them because I wanted to.  With the shoes, my pantyhose and short dresses I just loved my legs.

  • #80785
     Isabella Closet 
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    I have used many many different types and sizes of heels in my life. I am not a pro at all, so I still walk sexier and more confident on chunky heels, even if they are 5″.

    I love stilettos, but I still have some difficulties. I am sure I walk on them better than the average woman, but not a supermodel catwalk yet. My highest was 6″ on stilettos, super hard, but super sexy.

  • #80660
     Elise Michelle 
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    Since I’m already over 6 feet tall, I never purchased high heels until this fall. Then I saw a pair of suede boots with 3 inch heels that I just had to have. I must admit, I never feel more powerful than when I’m walking in those boots.

  • #80152
     Sophie Roberts 
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    I decided to go with a classic pair of black 4 inch court heels.  Just loved the look of them.

    http://highheelsdaily.com/wp-content/uploads/2014/07/nine-west-flax-pump-replaces-barbe.jpg

    Looked daunting when I first got them but after a few uneasy sessions was able to walk in them.

  • #79879
     Martha Lou 
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    I had to practice a lot. But when comfortable in my heels I felt like a sexy woman.

    I have gotten my woman’s walk down well.

    I love now going out in my heels and being a real woman.

     

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  • #78584
     Stella De Laluz 
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    Tonight I was working in my studio and had the building to myself. I ventured out into the hallway in a dress and heels. I heard my heels on a hardwood floor for the first time. There’s something about that sound I find enchanting as well.

  • #77758
     Amy Vanessa 
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    The first time I wore heels out in public in the daytime, it wasn’t very far, just to cross a busy street to catch a bus while wearing my 2- inch black pumps, but the feeling was awesome!!!

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  • #77688
     Dame Veronica Graunwolf 
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    I had a lot of  trouble finding shoes in my possible size…pumps 5 inch heels. As a diabetic, my feet swell from time to time, and I got a SIZE 11 from Walmart. They are tight….think I will try to find a size 13. I did get into the 11’s and struted up and down the hallways here in my building. I amazed myself, the other side of my brain is definitly female, things like fastening/unfastening bra, garter belts and corsets was easy and felt I had being doing for years. NOW…the shoes…I didn’t fall, trip, or stagger once. Yea Me!  Then came the runway stroll…….perfect….except for kicking myself in the ankle a couple of times. Still too afraid to try running as they are too tight. My hip bothered me the next day, but settled down. Now if only make-up was as easy

    Lady Veronica

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    • #77708
       Stella De Laluz 
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      I had mine on for some time and was informed my shins would hurt the next day. I guess I’m lucky. No after effects and that may be because I run a lot and I work my legs hard to keep fit. I’m also borderline diabetic and my legs now retain water a bit. I ordered a size 11.5 and is a good fit. I could probably do 11’s.

  • #77648
     Anonymous
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    Most amazing feeling ever walking and seeing yourself in heels! I especially love mule heels with sexy stocking

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  • #77638
     BryonyPoole 
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    We had a local charity walk for men to increase awareness of cancer and raise money for charity. Women already had a walk for breast cancer, so someone suggested the men should walk a mile in heels to support the women. Well, why not I thought (even if going in my girly clothes was not an option).

    So borrowed a pair of mid-size heels which just about fitted but a bit tight, and entered the walk with a load of women and other men.  Well, standing was OK, and a few unsteady steps later we were off.  Not too bad, but wobbly, for maybe a quarter of a mile, but then very painful but managed the whole mile. Made me realise what women go through to look good in heels.

    Now of course, no problem and I love heels (the right size of course), and wear them when I am dressed and can walk easily.  But my first attempt still amuses me.

    Bryony

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  • #77572
     Anonymous
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    <p style=”text-align: left;”>I must admit to being a teenager and spending school holidays with an Aunt and my Cousin out in the rural countryside on a big property,where the nearest neighbour was like 5+km away..</p>
    At that time i had the same footsize as my female cousin and Aunty, and one evening after watching a Dame Edna Tv event, it was suggested I try walking in some high heels.. (i boasted i could do it easily,never having tried previously..)

    My first attempt thankfully I tried a pair of maryjane kitten heels,with a pair of tan pantyhose and a cute pinaphore skirt n white blouse..My Aunty suggested the cuteness of the outfit..It felt liberating to be,complimented n coached in girly etiquette,wearing a wig n makeup..and being accepted as a girl..that memory left an indelible mark on me after that..and many years later my Cousin showed me the 20+ polaroids taken of me during those holidays,cute as a button on a tartan skirt..!! Many years later after ordering my first pair of neon pink classic 4inch pumps..and being excited when the postie delivered them.That very real excitement was relived again and again and began an insatiatiable desire to cultivate a stylish wardrobe of Feminine clothing & gorgeous high heels of pretty colors,styles,heights that gave me feelings of elated beauty, divine femininity and tight toned long legs as well..

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