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I Am A Crossdresser And I Love Lipstick

Personal Stories, Advice, and Support 959 People

    Lipstick And Smoking

    i like wearing lipstick and i love it when i am smoking a menthol cigarette and i see the lipstick on the butt of it xx
    georgiacd georgiacd 41-45 3 Responses Nov 11, 2011

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    I Sure Do.

    Back in the 60's (Only had Mom's) the only lipstick that I could get my hands on was red. I wore red for many years. Both of my g/f's in H S only wore red, so they put red lipstick on me when they would dress me. My wife caught me in full drag mode 1 month after we wed. Yes...
    sherrynpantyhose2k4 sherrynpantyhose2k4 51-55, T 3 Responses Apr 25, 2012

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    Lipgloss Is A Fav!

    I started using lipgloss in several different shiny colors.  My first choice is Maybelline Shiny-Licious, coral heat is my latest shade.  I just love the feel, the taste and especially the look on my lips!  I also like lip gloss that makes my lips sparkle!
    denisegurl2 denisegurl2 46-50, T 6 Responses Feb 10, 2010

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    The first time I tried on my Mother's lipstick

    was a huge disaster. I had discovered that I could make my lips red with watercolor and that it washed right off. That made me think that if I painted my lips with watercolor and applied lipstick over it the lipstick would wash right off with the water color. Stupidest think you...
    Robertredlips Robertredlips 56-60, M 1 Response Feb 27

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    Oh So Good

    There just something about grabbing a lipstick, twisting and putting it on that I can't explain. Its just feels so girly :)
    deleted deleted 26-30 2 Responses May 22, 2012

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    Crying For Lipstick

    When I was baby even before I was one, I use to cry at my mother when she wore lipstick-it took them a little while before the penny dropped that it was the lipstick that made me cry. As time went by I was at junior school and my mother had a cleaning job in a pub in the early...
    tubsy tubsy 56-60, M 1 Response Jun 21, 2013

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    Now, I Wouldn't Be Without Lipstick. Joy To The World

    A while ago, reading EP, I thought that wearing lipstick sounded like fun. Believe me, it is ! Bought some, went through the usual, with "BRIGHT RED" being the thing around the house. Eventually, I decided that I liked the silky feeling on my lips. ---And another thing...
    Moddle Moddle 61-65 3 Responses Mar 9, 2010

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    I Love Male To Female Makeup Transformation.

    Whenever my wife is not home, I trim my eyebrows, apply kajal and eyelashes, use cream concealer all over my face, apply a sexy dark red lipstick and wear a wig. Finally i wear her saree and jewelleries and her high heels. What a feminine feeling. I guess I look prettier than my...
    deep2502 deep2502 26-30, M 3 Responses Oct 11, 2012

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    So Many Shades, But We All Know What Red Is For...

    I just love to mix and match lipstick with my mood. But watch out honey when i am wearing red....
    swishykathy swishykathy 56-60, T 1 Response Dec 3, 2009

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    I look so great wearing bright red lipstick I

    have made it a part of my every day attire. Every morning I automatically put it on as part of my getting-ready routine. If I don't go to work that day I wear it to the grocery store and wherever and whatever else I do that day, and I feel terrific. On days I work I...
    Robertredlips Robertredlips 56-60, M 1 Response Sep 6

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    Lipstick Is So Feminine

     i love lipstick i remember as a you boy trying moms lipstick and loving it but not being sure why and as i got older i would borrow my sisters and by this stage i had figured out that i loved to wear female lingerie and clothes. so lipstick just went along with the cross...
    jarviscooper jarviscooper 36-40, M 3 Responses Nov 25, 2009

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    After my divorce my wife left behind many of

    her clothes and wigs and makeup. Soon I was using as much of her gear in private and it felt so special to be female. After a few weeks I bought a few clothes and shoes to supplement my wardrobe and went out on the streets as a woman. The feeling of the air round my legs and...
    deleted deleted 26-30 2 Responses May 12

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    i just love putting on some red

    or pink lipstick, best thing ever. soo girly :)
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 1 Response 5 days ago

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    Painting you.Their long embraceOf moistened

    lipsThe dance of tonguesThe sway of hipsHer perfect poutTransfers it's hueHoney,That colour,looks good on you!Let me paint themThe same as mineI know You'll like itIn a short timeCan I continueWith your face?You'll look so prettyMake no mistake.Look in the mirrorWhat do you seeA...
    charlie1960 charlie1960 51-55, M 3 Responses Jun 19

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    I love the lipstick on.

    .as red and bright as I can get it.. Then go thru a fast food drive thru.. Love it
    kysatinman kysatinman 41-45, T Dec 31, 2013

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    So Creamy And Sexy

    I really enjoy the creamy feeling on my lips when applying lipstick !!! Also enjoy the sexy look of my pouty lips after I'm finished !! Also like the sweet imprint they leave on the edge of a wine glass or on a cigarette !! Mmmmm !! Yessss !!!
    chrisg03 chrisg03 46-50, M 4 Responses Dec 25, 2010

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    Sexy Lips

    There is something truly sexy and sensual about finishing your make up with lipstick. Combining four senses (sight, touch, taste and smell) into a totally erotic experience. By the time I am putting on my lipstick, I am so aroused...Even though lipstick screams femininity, I...
    deleted deleted 26-30 3 Responses Aug 7, 2012

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    My Favourite

    Every since I was a young boy around the age of 4 I was always fascinated by lipstick, whether it be commercials advertsing make-up, magazine articles, movies with beautiful women, I always loved looking at their lips. One day when I was about 13-14 I finally worked up the...
    dodds44 dodds44 18-21, M Apr 23, 2013

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    So True

    love to put it on everydaylove it when I kiss my wife when I have lippy on.and so cool when in the gents and i am re applying my lippy, that gets the guys going.and at work too
    christinemelody christinemelody 56-60, T May 25, 2012

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    "i Am A Crossdresser And I Love Lipstick"

    "I Am A Crossdresser And I Love Lipstick" the feel of it on your lips such turn on especially if you are going to kiss another gurl or suck a **** love the taste and marks it makes!!!The first time i was dressed up by girl next door she put slutty red lipstick on my...
    mandiejune mandiejune 51-55, M 2 Responses Nov 26, 2009

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    Lipstick Makes My Day!.

    I adore the feeling and look of lipstick. I only crossdress about once a week, but I wear lipstick almost every night.I like maybelline moisture whip the best. I have many colors, and I use clasic red, pink,and wine and roses, the most. It goes on so smoothly, and it's so...
    sissyrachel48 sissyrachel48 61-65, M 3 Responses May 2, 2012

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    Maybe Just To Look Pretty

    Lip stick, chap stick, lip gloss, shimmer lip gloss. I wear them all ... daily. I usually find a color close to my skin tone and wear it every where. Lipsticks are made with various sunscreens and moisturizers as well as oils, cocoa butter and lanolin and such to keep ones lips...
    Josie06 Josie06 56-60, F 4 Responses Oct 15, 2011

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    One Of My Last Experiences

    I didn't start with lipstick till I was almost ready to pass in public.  The same with nail polish and artificial nails.  After that I was hooked.  I had five colors to wear with my five wigs.  Now I wouldn't go out with out lipstick and gloss to only get the...
    deleted deleted 26-30 Jun 21, 2010

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    Long Lasting Lipstick

    I wish someone would invent a lipstick which was at least semi-permanent and stay on for at least a week and not be removeable, It would be such a thrill to be tied and have this put on my lips, especially if it was a really bright colour xxx hmmm might not be able to control...
    AliceCornwall AliceCornwall 36-40, T 9 Responses Apr 21, 2013

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    I Love Lipstick

    Hey :) I just wanted to share this because im wearing lipstick right now. Lipstick is one of my favorite things i as a crossdresser to use, I just love the feeling i get on my lips, it feels like im coverd in it and i love it. I enjoy just the act of putting the lipstick on my...
    Mayaunder Mayaunder 18-21, T 2 Responses Feb 28, 2013

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    Why I Use Lipstick

    Why do I enjoy so much using lipstick? Is it like kissing another stick and feeeling it on my lips for hours? Or because I imagine I am inviting her to kiss me, lightly first, with tender love, and then with brutal abandon... Or because I hope to leave an imprint of my...
    Cigysub Cigysub 56-60, M 2 Responses May 5, 2010

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    Lipstick!!!!!!!!

    I think foundation is ok, rouge is fine, mascara is neccessary, eye liner good, eye shadow aluring, but with out lipstick you might as well through all the rest out. Lipstick is the absolute must for the feminine face. It sets off some bright color to an otherwise drab surface...
    bahli bahli 66-70, M 2 Responses Apr 24, 2013

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    I sometimes keep a small card in my wallet

    with a picture of sexy red lips. On the lips are the words "Penis Garage". I have an unbreakable rule that when the card is in my wallet I actually have "Penis Garage" tattooed on my lips. That forces me to wear red lipstick wherever I go to cover up the embarrassing tattoo...
    Robertredlips Robertredlips 56-60, M Aug 22

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    I Love Wearing And Putting On Lipstick

    Lipstick is what started me and a long road of dressing and purging. Wearing my Mabeline make me pink lipstick right now that my wife bought for me.  
    JeanW1 JeanW1 56-60, M Sep 25, 2013

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    Lipstick Love

    Lipstick is definitely my favourite part of a makeup session. It's the last thing you put on and is the crowning glory to all your hard work. I love to watch tranny **** and whilst blow jobs, anal, 69's are all great to watch my favourite thing to watch is when two tgirls are...
    debbiesucks debbiesucks 46-50, T 5 Responses Nov 29, 2012

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    I'm Always In The Mood To Wear Lipstick..

    I love the feel of lipstick on my lips. Some days I leave the house wearing a pale lipstick that is hardly noticeable so I can wear it longer. I prefer red lipstick, matte, dark red, but most days that isn't practical. I love dressing up all the way with a wig, mascara...
    DanielleOAK DanielleOAK 56-60, M Sep 27, 2010

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    One day I came home from school

    and felt the need to wear women's clothing. I started with my mother's lipstick and got so excited that I automatically jacked off without even trying. The next day I was able to get fully dressed up in women's clothing, panties, pantyhose and makeup and even a wig. I was is...
    Julianne6969 Julianne6969 61-65, T 11 Responses Dec 20, 2013

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    Early Experiences

    When I was very young, maybe 3 or 4, I tried on my mother's red lipstick. When she saw me, she went berserk, drug me in the bathroom and scrubbed my face with a rough sponge. That has always stayed with me and I guess imprinted on my mind. When I was about 7, I was in the...
    redlips64 redlips64 56-60, M 2 Responses Mar 30, 2012

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    Must Have

    I dress in part most days now.wont be long til I go all the way.but in the meantime I love to put a bit of lippy o to go out, ot to et the bus to work.love the femme feeling and the looks I get cos outwardly I still appear male but inside I am so girly.love plum colous, much...
    christinemelody christinemelody 56-60, T 2 Responses May 11, 2012

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    Related Experiences

    Love putting on lipstick and taking pix :)
    xxalicerosexx xxalicerosexx 16-17, F 1 Response Sep 27

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    Lipstick always makes me feel better.
    Shannongirlyboy Shannongirlyboy 46-50, T 2 Responses Sep 23

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    A bold color of lipstick <3
    xxalicerosexx xxalicerosexx 16-17, F 1 Response Oct 9

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    I just started my MAC collection and I can't wait to get more. This pic doesn't include the new 5 lipsticks I got from the new Matte Collection
    atadas12 atadas12 18-21, F 3 days ago

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    I am looking to chat if anyone wants to chat with a guy/crossdresser with slutty lipstick on I would enjoy
    Yyntnt80 Yyntnt80 46-50, M 1 Response a week ago

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    I am a pantyboy lipstick on my knees sub male
    Yyntnt80 Yyntnt80 46-50, M Oct 7

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    I'm in my slutty panties and lipstick I hope I can please someone through chat I'm on my knees and ready
    Yyntnt80 Yyntnt80 46-50, M 1 Response 1 day ago

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    I just love wearing red lipstick! It look sexy and powerful, it goes according with my personality and when I leave lipstick when I kiss someone... Well I don't know, it's the best...
    elisasama elisasama 16-17, F Oct 4

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    A principal of a small middle school had a problem with a few of the older girls starting to use lipstick. When applying it in the bathroom they would then press their lips to the...
    fetish27 fetish27 46-50, F 8 Responses Oct 3

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    my result for the lipstick quiz" "you should wear bright red lipstick" In Your Face Sexy and Flirty Your look: Flawless Beauty Your signature lip gloss flavor: Cherry
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 1 Response Sep 27

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    I'm an European boy, not a "teen" anymore since I've already turned 20, but I think this is the best group to post my story. Crossdressing has been part of me since I was 13, and...
    Eurocd Eurocd 18-21, M 1 Response Oct 10

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    I wear lipstick almost everyday, I just love how it feels.
    Shannongirlyboy Shannongirlyboy 46-50, T 1 Response Sep 27

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    The red in the picture ^ but yeah, i love red lipstick.
    macibabyy macibabyy 16-17, F 7 Responses Sep 28

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    I absolutely love wearing red lipstick. It's bold and beautiful ;)
    deepaforeverangel deepaforeverangel 22-25, F 3 Responses 2 days ago

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    closet crossdresser since i was 10 years old looking to talk to other closet crossdressers
    tina1952 tina1952 61-65, M 1 Response Oct 13

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    Having fun with lipstick <3
    xxalicerosexx xxalicerosexx 16-17, F 2 days ago

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    Are there any girls from New Jersey that like crossdressers? I'd love to hear from someone and chat
    Lovethembig Lovethembig 18-21, M 1 Response Sep 28

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