Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Love My Sissy Boobs

Personal Stories, Advice, and Support 293 People

    How I Ended Up With 38c Boobs

    LET ME START MY STORY BY SAYING IVE ALWAYS WANTED BREASTS THAT WOULD FILL A BRA DURING PUBERTY I HAD BREASTS THAT WERE LARGE WITH AUREOLES THAT WERE SO LARGE I WAS EMBARRASSED TAKE MY SHIRT OFF. IT WAS AROUND THIS TIME THAT I TRY ED IN MY MOTHERS LONG LINE  BRA I DIDN'T FILL...
    HIPPILOTTA HIPPILOTTA 66-70, T 2 Responses Nov 3, 2010

    Your Response

    Cancel

    About Time

    At the age of 60 i had a scare. i felt a lump growing in my right booby. Six years ago i had a kidney removed along with the cancer inside. No needless to say, a boob mass was not a comforting sensation. Finally my insurance authorized an ultrasound which led to my first...
    redlace redlace 61-65, M 10 Responses Sep 6, 2010

    Your Response

    Cancel

    Wanting My Boobs To Grow!

    I have dressed off and on for many years. I have enough fat to make some great cleavage with a good push-up bra and have decided I want real boobs. I've started taking pueraria mirifica and using their breast cream. Not sure how far I'll be willing to take it but I can't wait to...
    julietvslut julietvslut 61-65, T 1 Response May 25, 2013

    Your Response

    Cancel

    Nipples

    Years ago I had very small nipples that didn't jut out at all. Not inverted, but I really couldn't reach down and get a good hold of one. They weren't sensitive at all. I decided I wanted to get them pierced as that was the early days of nipple piercing. I did and my girlfriend...
    onefourfun4u onefourfun4u 61-65, M 5 Responses Oct 31, 2012

    Your Response

    Cancel

    I Do Love Having Boobs

    I have taken estrogen several times over the past 25 years the first time the doctor had given my wife a years suppily of birth control pills which really upset her stomach so she threw them away so before throwing the trash out I stashed the pills which I took twice a day untill...
    marlene223 marlene223 56-60, T 1 Response Jul 3, 2011

    Your Response

    Cancel

    Noticed My Small Breasts.

    I have noticed recently that I have small breasts. They were never noticeable before but one of my wife's friends commented on them. I then noticed they are a good hand full and I have not been taking anything for them. Not that I am a wear of at least.
    confinedhubby confinedhubby 41-45 2 Responses Dec 30, 2012

    Your Response

    Cancel

    I Luv Having Boobs

    i have always wanted them and when my mother in law stoped her HRT she gave me her remaining script of estradiol wich ran out after 3 and a half months. it worked pretty well and fast. it was enough to get the girls going but i ran out before reaching my goal of a 40dd. i am a 40...
    DeeDee1966 DeeDee1966 41-45, T 10 Responses Jun 22, 2011

    Your Response

    Cancel

    I Hope They Grow Bigger

    I just love my sissy breasts, too. They are starting to get big enough that they are getting more than obvious under a t-shirt. I wear padded bras to accentuate their shape. I am 64 and I think their growth must have to do with BP meds and being a little overweight. My wife...
    sissyallison sissyallison 61-65, M 1 Response Aug 26, 2012

    Your Response

    Cancel

    Gettin There

    I have been wearing bras off and on since I was 12. I never used to have much to fill them with and hated stuffing them because I love the way the feel on my *******. My wife shares my massive bra fetish with me. She makes me wear a bra all the time. Because of this, my...
    deleted deleted 26-30 4 Responses Mar 7, 2011

    Your Response

    Cancel

    Secret Ritual

    I have been consistantly crossdressing since i was 12 years old. I got my first experience at an even younger age when i put a pair of silk panties on and realized that I really liked the feeling. I then would try to put on dresses and all other female clothing. It wasnt until...
    Kristi74 Kristi74 22-25, M Jul 13, 2013

    Your Response

    Cancel

    I Would Love Some

    I dont have any boobs yet but I am planning on growing mine to a 40 c I plan on takeing some natural suplments.  but right now I use breast forms and I love them but they are troublesome at times and I swet behind them in the summer 
    deleted deleted 26-30 1 Response Mar 14, 2013

    Your Response

    Cancel

    Just Love Having Feminine Looking Breasts!

    I started growing boobs after turning 60 and going on some meds which have gynecomastia as a side effect. My boobs are now over B cup size and feminine shaped. My wife loves my growing feminization, and so do I.
    terrifemme terrifemme 61-65 Nov 19, 2011

    Your Response

    Cancel

    "i Love My Sissy Boobs"

    I love everything about my sissy boobs. But my favourite is looking down at them held up and out in my 1/4 cup bras.In this manner Mistress L can easily access them, to touch kiss or her favourite bitting them until i groan like the little **** that i have become. L also loves...
    slavetoby slavetoby 56-60, M 2 Responses Dec 8, 2010

    Your Response

    Cancel

    Related Experiences

    oh yes i do love to admire them and play with them
    veryunusual1 veryunusual1 26-30, M Aug 7

    Your Response

    Cancel
    I am thankful for what I have and wouldn't change a thing!
    Nihnox Nihnox 18-21, F 1 Response Aug 4

    Your Response

    Cancel
    Boobiessssssssssssssssssss :)
    Heyababe Heyababe 18-21, F 6 Responses Aug 6

    Your Response

    Cancel
    I call them fun bags ... Lol...
    Mihkowakayios Mihkowakayios 13-15, M Aug 8

    Your Response

    Cancel
    Flat-chested, small, extra small breasted ladies are my poison! I keep wondering why the bloody hell ladies go for a boob job!
    Captain06 Captain06 41-45, M Aug 18

    Your Response

    Cancel
    They are Au Natural & 100% real!
    whatdreammaycome whatdreammaycome 56-60, F 4 Responses a week ago

    Your Response

    Cancel
    Mine are round and soft, and fun to squeeze and play with ♡♡ I like to stare at my tatas in the mirror. :)
    IEatzFriedChicken IEatzFriedChicken 18-21, F 2 Responses 5 days ago

    Your Response

    Cancel
    One day when I was at work over the summer before I went to college, there was a woman who, no lie, had breasts as big as her head, if not bigger. I just wanted to stand and look...
    iosefstalin19 iosefstalin19 18-21, M 1 Response 3 days ago

    Your Response

    Cancel
    Who doesn't? I thought I didn't care. I date a lot of tall and skinny girls, that is normally my type, but I hooked up with a girl yesterday with the largest and most beautiful...
    Carlsoncarly Carlsoncarly 18-21, M 1 Response Aug 9

    Your Response

    Cancel
    I love wearing all kinds of lingerie, and I especially like the kind that makes me feel like a sissy. I made this video when I was feeling a little sissyish. I hope you like it...
    VictoriaFredericks VictoriaFredericks 36-40, M 3 Responses Aug 12

    Your Response

    Cancel
    Yesterday was the fist day i spent with by master. I loved being all dressed up in really cute sissy clothes (he even made me lock my boy **** in a cage) and he made me service...
    bottomslut1 bottomslut1 18-21, M a week ago

    Your Response

    Cancel
    I am a sissy that wants to be taken and used by alpha males and turned into a sissy bimbo ****
    Sissyboitaylor Sissyboitaylor 18-21, T 8 Responses Aug 3

    Your Response

    Cancel
    I'm not Sure I took a Sissy quiz on a site called ProProfs and when I submitted it my results said... ??? I'm sorry. But this test was for men only not girls. So...did I pass...
    noahman97 noahman97 16-17, M 13 hrs ago

    Your Response

    Cancel
    I have extremely small boobs.. I basically don't have boobs... I was bullied in jr high and high school because I looked like a ten year old boy, but now I look at them and I'm...
    Angelwuvsyu Angelwuvsyu 18-21, F 19 Responses Aug 9

    Your Response

    Cancel
    Hey I'm in love with seeing my name on chicks boobs right now so if any one could send me a photo with jimmee written across there boobs that would be amazing
    jay4661 jay4661 18-21, M Aug 15

    Your Response

    Cancel
    hi im a 18 yr old sissy that loves to crossdress and turn all girly and naughty, i love being demanded to do things and i am looking for a mistress who can take care off me i can...
    stranger123456 stranger123456 18-21 9 hrs ago

    Your Response

    Cancel
    I love my big natural fat-girl boobs! 46H, A bit saggy, but still firm. Sensitive nipples. :) Great boobs.
    MrsApple MrsApple 26-30, F 12 Responses Aug 4

    Your Response

    Cancel
    I am trying to find a way to be noticed as a sissy by women, last night I went out back to a main road, and I wore just panties and shoes, and stood by the road, so many cars drove...
    sissyslut4training19 sissyslut4training19 18-21, M 6 days ago

    Your Response

    Cancel
    I'm young and would love to be an older guys little sissy b*tch
    notsoninjaninja notsoninjaninja 16-17, M 3 days ago

    Your Response

    Cancel
    wen i wore dress dat expose my boobs more sexyly..dat tym wen my dad started starring at boobs like succking it...i wish to hug my dad tightly and wanna **** him
    neethug neethug 18-21 5 Responses Jul 31

    Your Response

    Cancel
    In general I like all types of boobs but big ones are nice:) I myself have big boobs so I find that trait very attractive.
    xoxokendyl xoxokendyl 16-17, F 5 Responses Aug 2

    Your Response

    Cancel
    Gosh some of those online tests are absolutely worthless! LOL But, on the few that were actually worth the time to take... I passed the Sissy Test, with flying colors!
    curiositykillz805 curiositykillz805 46-50, M Aug 12

    Your Response

    Cancel
    Guys only like big boobs..and I have small ones What can I do ?! :( well what I hate is when ur close friends pick on u for small boobs. I hate it seriously. It makes me feel so...
    Bbygrlnene Bbygrlnene 13-15, F 3 Responses Aug 12

    Your Response

    Cancel
    how can i become some ones sissy
    gerommino gerommino 66-70, M 3 Responses Aug 13

    Your Response

    Cancel
    I'd never do this in real life, it's just a fantasy of mine. I'm a 100% straight guy but at night the thought of being blackmailed and turned into a sissy boi is one of my biggest...
    NightlockForever NightlockForever 13-15, M 3 days ago

    Your Response

    Cancel
    Sissy white boy. All I do is crave c*ck
    raelynnCD raelynnCD 18-21, T 2 days ago

    Your Response

    Cancel
    You Tell Me I can understand why some of my friends think I'm girly or even gay (which I am, but they don't need to know right? ^^; ). I’ll just compare myself to most of the...
    noahman97 noahman97 16-17, M 1 Response 1 day ago

    Your Response

    Cancel
    I am looking for mistress or master to nake me their sissy princess toy im from newcastle uk message me of youd like a new toy
    jamieleeaka jamieleeaka 18-21, M 8 hrs ago

    Your Response

    Cancel
    i love to expose my boobs while im going out......wish to wear dress without bra,,,
    neethug neethug 18-21 2 Responses Jul 31

    Your Response

    Cancel
    I love my neighbour big boobs
    ApxentMinded ApxentMinded 16-17, M Aug 17

    Your Response

    Cancel
    I was giving my boyfriend head recently and he was lasting for ages. We were both naked as well. He was playing with my boobs and hair while I was blowing him. He said he was close...
    AmyGirlAutumn AmyGirlAutumn 18-21, F 4 days ago

    Your Response

    Cancel
    And after the past 2 days of beyond stuffing! I woke up this morning to this..... So I got up after a good nights rest after 10pounds of food in one day I had to wait all morning...
    SherbertGainer SherbertGainer 22-25, F 2 Responses 3 days ago

    Your Response

    Cancel
    my boobs have always been small and I love them just as they are. I will never have anything done to them.
    smallboobs32 smallboobs32 31-35, F 19 Responses Jul 27

    Your Response

    Cancel
    the bigger the better they must be all natural it's so much fun to enjoy a woman's chest how I love kissing them and licking them and laying upon them when I want to rest.Let me...
    bignatbreastluver bignatbreastluver 46-50, M 1 Response Jul 30

    Your Response

    Cancel
    Can I see your boobs and I will give aiming back
    kooldude56 kooldude56 18-21, M Aug 15

    Your Response

    Cancel