I Have Worn Lipstick

Personal Stories, Advice, and Support 2,864 People

    Question To Women: Have You Experienced Lipstick On Lipstick Kissing With A Tranny/crossdresser?

    Lipstick looks and feels wonderful on the lips. The sensation of kissing or making out with someone while both are wearing lipstick is incredible. I have kissed women while we both were wearing lipstick, and loved it. The women kissing me back seem to have enjoyed it as well...
    BizSuitStacy BizSuitStacy
    51-55, T
    8 Responses Mar 25, 2011

    I Have Worn Lipstick

    A few days ago I did something I’ve never done before – I stole my wife's makeup kit, closeted myself in my office on a holiday, applying a burgundy lipstick on my full mouth. I felt all through the day and whenever the phone rang in my office, i viewed myself on the...
    padmalayam padmalayam
    36-40, M
    Dec 21, 2009

    A Learned Thing

    My mother taught me very well while I was growing into the woman I am today.  From that first day that she started to feminize me on my eighth birthday, she had two rules that she stood firm on.  One was whenever she had dressed me up, which was at least once a week and more as...
    betty3100 betty3100
    51-55, T
    4 Responses Apr 3, 2011

    Getting Used To It

    Hello hope everyone is doing great. I have been wearing lipstick more and more around the house but the kick I used to get is lessening. I don't know if I'm getting used to it or what. Sometimes I use lip gloss as well to enhance the look. Anyways I hope I don't lose the thrill...
    sarahgirlelizabeth sarahgirlelizabeth
    36-40, T
    20 Responses Jan 13, 2013

    Lipgloss Is My Fav!

    Of course I wear lipstick when I am all dressed up, but I also like to wear lipgloss when I am in guy mode.  I get soo excited when my lips are shiny and glittery.  I love the look and the taste of Lipgloss, I apply it often!   Wet and Wild Brilliance is my...
    denisegurl2 denisegurl2
    46-50, T
    3 Responses Mar 15, 2010

    Yes and It's Wonderful

    Wearing lipstick makes me feel good. It makes me feel feminine. It makes me feel like a woman. If there is one item identified with women, their icon so to speak ... it would be lipstick. Feminine. Womanly. Delicious. Oh, so good!
    Josie06 Josie06
    56-60, F
    6 Responses Sep 23, 2008

    I am a 15 year old sissyboy I secretly steal

    some my sisters cloth she's 17 I wear panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans bras but honestly I'm a beginner in make up but I love lipstick
    deleted deleted
    26-30
    Jan 9

    Lipstick

    I remember when I was little, I'd watch my mother putting on lipstick and I'd ask her if I could have some on and she would put a little on my lips. I love the feeling and taste and smoothness of it. so feminine!!
    Julie4728 Julie4728
    51-55, M
    1 Response Feb 19, 2011

    Lipstick

    It feels and looks better than chap stick.
    ilkskrts ilkskrts
    56-60
    1 Response Apr 20, 2011

    I tried on some of my mom's

    as a kid, just to see what it felt like. No big deal.
    Hobvin2884 Hobvin2884
    41-45, M
    Jan 8, 2014

    Ooh I love wearing lipstick

    but I used to get it on my teeth a lot, then I saw this tip where after you put it on, suck on your finger real quick and it takes all the excess of so it keeps your smile whitee 😬😃
    Selphira Selphira
    18-21, F
    1 Response Sep 16, 2014

    I to have worn lipstick also I've worn make-up,

    even dresses and heels and I loved it so much I am taking feminizing hormones
    deleted deleted
    26-30
    2 Responses Aug 28, 2014

    I wear lipsticks. I have the colors red,

    dark purple, black, and brown. I mostly wear red or dark purple.
    lorrena19 lorrena19
    18-21, F
    Feb 23, 2015

    I love wearing lipstick.

    It's just so lovely and awesome, and I find it makes kissing wonderful too.
    AnyaGirl AnyaGirl
    26-30, F
    1 Response Feb 22, 2015

    Just lipstick? Come on boys at least 2 of my

    men let me put a full fledged face of makeup on them
    anjay813 anjay813
    26-30, F
    7 Responses Apr 9, 2014

    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted
    26-30
    Dec 30, 2015

    I Love Wearing Lipstick

    I love wearing lipstick, especially the sun colors. I also really love the ones I've seen advertised a lot on glamour magazine lately from Clinique.
    pfc8273 pfc8273
    46-50, T
    1 Response Jun 12, 2012

    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted
    26-30
    Dec 11, 2015

    when I'm all dressed up I love wearing lipstick

    probably the best type of make up for me I love mac , cos , and naked
    deleted deleted
    26-30
    Apr 8

    I didn't want to :( someone at a slumber party

    years ago put it on me while I was asleep.
    AfterFall AfterFall
    22-25, F
    1 Response Feb 23, 2015

    Wearing Lipstick.

    one of my favorite things is putting on my lipstick.thats the final touch after putting on my makeup.its also one of the most feminine parts of being a woman.phylisanne
    phylisanne phylisanne
    70+, F
    2 Responses Oct 7, 2008

    The following is true I wore lipstick

    before I was allowed. I was a child, thinking it would make me look more grown up. It didn't. It made me look like a child playing at looking grown up. Once again mom was right. Once I got old enough to be allowed to wear makeup, I realized I actually looked better without it...
    Serenitree1 Serenitree1
    70+, F
    Dec 30, 2015

    Love Wearing Lipstick

    I have been wearing lipstick for as long as i can remember, My earliest memory ( when I was about 3 or 4)is going into my mother's room and sitting at her vanity and putting on her red red lipstick, I loved it and could not understand why my mother got mad at me. I just love...
    missytiger missytiger
    61-65, T
    5 Responses Nov 15, 2010

    I would probably only wear it

    if I was feeling really fancy :P Mostly it's just chapstick or lipgloss for me. A bit low key since I usually draw attention to my eyes instead of my lips.
    ErraticSarcastic ErraticSarcastic
    31-35, F
    Dec 7, 2015

    I Was Five...

    I was five years old when I was forced by a couple of girls to wear lipstick; I was over at their house while my parents were away, work and other things and had to be baby-sat. The girls' mother was asleep, and they took advantage of that time to make me do that to myself. I...
    amytheinvalid amytheinvalid
    26-30, T
    Oct 13, 2012

    i put on lipstick today

    but had a lil stubble so no photos . i put on my wig .. n did stuf . n .. o-d while staring in my own eyes in a mirror . i look like a whole other person . it was crayzee . im gona do it again ! ..
    cdwishimatgurlCalandraBelle cdwishimatgurlCalandraBelle
    36-40, T
    2 Responses Feb 7

    I saw an old picture of my young self wearing

    lipstick. I had look funny. LOL
    mother1983 mother1983
    31-35, F
    2 Responses Dec 7, 2015

    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns skinny jeans heels lipstick and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted
    26-30
    Dec 5, 2015

    Makeup And Men

    how many men actually wear or want to wear makeup. i use lipstick regularly, and love it
    deleted deleted
    26-30
    6 Responses Sep 2, 2012

    Glow It

    I can't imagine stepping out without a lipstick or lip gloss. At night and in parties i wear lipstick with a UV glow. I love watching it glowing.
    swisss21 swisss21
    18-21, F
    Nov 11, 2012
    macherxo macherxo
    26-30, F
    Jan 7, 2014

    Yeah in like forever ago

    and there is no desire either jeez i went to rich *** school wearing no makeup , no manicure No jewelry and walmart clothes that were a buck a shirt , i must be seriously depressed i guess :((
    anasteel2 anasteel2
    41-45, F
    Sep 17, 2014

    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted
    26-30
    Nov 24, 2015
    bloodyzombie19 bloodyzombie19
    16-17, F
    Dec 7, 2015

    T-girl Loves Lipstick

    My first expression of my transgenderedness was trying my mom's lipstick. I love to wear it and m favorite color is red. I have all the make up any girl would have but am a sucker for lipsticks, I buy new ones all the time. I miss the ones that had a slightly perfumey taste.
    Genivieve Genivieve
    56-60, T
    2 Responses Sep 30, 2011
    xxalicerosexx xxalicerosexx
    18-21, F
    1 Response Oct 19, 2014

    Only for special occasions

    but I love lipstick and the way it makes my lips look (:
    taylor468 taylor468
    18-21, F
    Nov 30, 2013

    Next Door Neighbor

    My next door neighbor had caught me in her clothes one day while I was house sitting for her and she taught me alot about make-up. She told me if I was going to dress as a woman, I should look like one too! My favorite experience was when she was applying lipstick to my lips, I...
    allwrappedupinit allwrappedupinit
    51-55, M
    4 Responses Apr 27, 2011

    I love lipstick, and I have soo many different

    colors... I especially love black, purple, and silver.
    JusticeTargaryen JusticeTargaryen
    31-35, T
    1 Response Sep 16, 2014

    What I'm Wearing Out In Public Currently...

    I have this 'Healthy Rose' lipstick that I'm wearing right now, because this morning I felt a slight burn on my lips. Old man Winter is on it's way, and since I am out of lip balm, this works well. I dab it, and then with a napkin/tissue, I dab off just enough, so that a thin...
    amytheinvalid amytheinvalid
    26-30, T
    Oct 15, 2012

    I'm a guy, I'm bicurious

    and want to cross dress as a girl - I want a woman in my life who can teach and train me to be a girl through clothing and make up - I want to also experience having a boyfriend with myself as there girl... this fascination of all things womanly started with a tube of lipstick...
    eeesh eeesh
    22-25, M
    2 Responses May 3, 2015

    Lipstick And Cigerettes

    i just love getting all girly, put on fresh lipstick, grab my purse and stepping outside for a smoke! something about seeing my lipstick on that filter! tasting my lips mixed with the smoke, it feels so sensual!i don't know why i associate smoking with femininity, maybe because...
    JessicaMann JessicaMann
    41-45, T
    3 Responses Mar 16, 2012

    I Have Worn Lipstick

    I watch my wife putting on her lip pencil and lipstick every day, this really fanicates me. I have my own soft pink lipstick and pencil which  i wear around the house when I am alone.  My girlfriend enjoys playing with make up so we have fun and i get better at...
    mickann mickann
    41-45, M
    1 Response Feb 5, 2010

    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I'm secretly attracted to masculine tough hairy men I love red and purple lipstick
    deleted deleted
    26-30
    Feb 3

    Ex Gilfriend

    i have let my ex girlfriend put make up on me... i acted like i didnt want her to do it but inside i wanted to wear her clothes after it.. it felt a little good sitting there while she did my make up
    YoungFreeSingle1 YoungFreeSingle1
    22-25, M
    1 Response Jul 6, 2013

    My Lipstick

    I wear lipstick everyday. it protects they lips from chapping. and no one has ever said a word too me about it I have had a few womens too ask me if I had on makeup. I tell them yes. and they jusy grin.
    cdlisa1963 cdlisa1963
    46-50, M
    Apr 1, 2012

    Related Experiences

    I have worn these boots extensively the last few days, had to polish them and condition them:) DONE!!!!!!!
    JennyTom JennyTom
    41-45, F
    1 Response Apr 11
    I like pink lipstick but it look ugly like me. I stay away from hot pink, light pink lipsticks. I like picking them up and staring at it when I buy dark lipsticks. I think it's my...
    staystyleandsmile staystyleandsmile
    18-21, F
    1 Response Apr 8
    I love red lipstick it fits me I love purple pink black roo but red mo
    deleted deleted
    26-30
    Apr 8
    I love red lipstick it fits me I love purple pink black roo but red mostly
    deleted deleted
    26-30
    Apr 8
    So my best friend comes over last night, most of it is spent with him talking about his problems, which is fine, I didn't mind listening and talking about that. But when you spend...
    Redstar86 Redstar86
    26-30, M
    2 Responses Apr 7
    I do get very deep in my fantasies and i love sharing them with people who are open to accept them and even enjoying being in that moment! I love to create stuff which i have not...
    pleasuretobehere pleasuretobehere
    26-30, M
    Apr 3
    When I was in Junior High the whole class got it one at a time, for misbehaving substitute teacher. Our science teacher was strict and didn't tolerate talking or not doing what...
    davedexp davedexp
    56-60, M
    1 Response Apr 3
    My wife and have had many threes ones with her girlfriend but I would really like to try mfm. I've got a best friend that packs a 10" beast and I want to want her enjoy it. Not...
    Shootinone1 Shootinone1
    26-30, M
    1 Response Apr 3
    Call of Duty zombies dream, love this because I get to be with my two favorite characters Nikolai and Dempsey! I ended up on the catwalk in Call of Duty zombies Der Rise. I...
    CaptainDragoness CaptainDragoness
    18-21, F
    Apr 3
    Just got done downloading 78 solid color anime wallpapers. They are really nice to look at. I have them set on a slide show to change every minute. Can you believe that? 78...
    jasonBK1 jasonBK1
    18-21, M
    Apr 3
    Anyone else have one? If you do comment down below, don't be shy I don't judge
    unknown0726 unknown0726
    13-15, F
    4 Responses Apr 3
    My therapist lied to me. Instead of telling me that she had married months ago and was pregnant, so she couldn't take sessions, she told me that I was at fault because I couldn't...
    lonelylifeindia lonelylifeindia
    26-30, M
    Apr 3
    I can't wait to have kids , I know it's no going be easy but it's something I always wanted and I know when time is right GOD will allow to have one & I know it will be the...
    deleted deleted
    26-30
    1 Response Apr 3
    They don't scare me so much anymore. I realized I was beginning to overcome my fear when I was home alone at night watching a movie and felt something touch me after feeling it...
    thisisnotanexit thisisnotanexit
    26-30, F
    1 Response Apr 3
More Stories