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I Love My Sissy Boobs

Personal Stories, Advice, and Support 292 People

    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

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    "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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    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 3 Responses Dec 30, 2012

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    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

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    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

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    Related Experiences

    I love my boobs....38E!!! I love just wearing a white tee 2 sizes to small.
    NIkki38E NIkki38E 36-40, F 31 Responses Jul 3

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    Nothing better than seeing a nice huge set of bo.obs, love em!!
    Wannalovelife Wannalovelife 13-15, M Jun 22

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    absolutely love em :D i used to date this girl who had the most beautiful pair of 36Ds <3 remember them to this day and i always will
    sholmes1990 sholmes1990 22-25 2 Responses a week ago

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    I used to crash at a friends house years ago she was sharing a room with another girl so I would bunk with her in this crappy single hold out bed but the one or two perks wear her...
    ApollosArrow ApollosArrow 18-21 1 Response Jul 2

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    I luv them a lot ❤️❤️❤️❤️❤️❤️
    mrbobby1909 mrbobby1909 31-35, M 2 Responses Jul 5

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    Well they don't have to be huge but yes this is true I do dig mammaries! 😋
    MrsGigalowJr MrsGigalowJr 26-30, F 6 Responses Jul 13

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    Lol I wanna see lol love rating boobs
    Rockman88 Rockman88 22-25, M 11 hrs ago

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    I love my boobs, I wish I had enough confidence to wear no bra wherever :), I love them getting sucked its amazing 😍
    annonymous1999 annonymous1999 16-17, F 9 Responses 3 days ago

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    I love being a sissy, even more than that I love playing with others. There's nothing better than licking down someone and ripping a hole in some nylon stockings thirsty for her...
    raelynnCD raelynnCD 18-21, T 2 days ago

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    To take me and to tell me that I am a latex sissy slave. I would say "I am your latex sissy slave". Take me and use however you wanted me as long as I am a latex sissy slave. That...
    Sissyslavekylie Sissyslavekylie 16-17, M 3 Responses Jun 22

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    This is very weird. My sister has big boobs and I really like them. I'm a male and I am just attracted to big round boobs, even on my sister. Sometimes it makes me feel terrible...
    tdotman97 tdotman97 16-17, M 2 Responses a week ago

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    I have really nice boobs. They arent too big and flabby but small and perky. I really like them. they make me proud - go boobs! *some people on here have nasty boobs, so be...
    Rltdancer Rltdancer 18-21, F 7 Responses 5 days ago

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    I got 100% Sissy on The Sissy Test, Found it on Google, now I am going to take the Inner Gender Exam or something, will goggle it and let you know my results and the name of the...
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T 1 Response 1 day ago

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    Well, I prefer small boobs. Unlike the world obsession for huge boobs - I can't stand big floppy boobs- or Rock hard implants, all disgusting. Give me a natural A or B cup any day...
    cumdrip cumdrip 56-60, M 2 Responses 3 days ago

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    I believe you are who you see you're self as and if that's a women even tho you're a man who the **** saids ? Religion ? Pfffft **** that be who ya want even if it does mean you...
    kerw94 kerw94 18-21, M 4 Responses Jul 7

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    Would love to meet a cool guy who was Dom and into a Sub Sissy Boi!
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T a week ago

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    i dont really have real man boobs their more like fat boobs. But I do really want them and really need help and advice but i dont have a ton of money to spend on this. can anyone...
    jasinskigainer300 jasinskigainer300 18-21, M 1 Response Jul 3

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    Never told this to anyone. The first time I saw boobs was when I was 15 and it was my aunt. She was like 40 years and had a firm pair of boobs. There was a small hole in bathroom...
    dadamoney dadamoney 31-35, M 1 Response Jul 12

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    I love boobs like who wouldn't
    shiney015 shiney015 13-15, F 3 Responses Jul 1

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                     Name:         Kimberly Sherrington ...
    BigCrow BigCrow 31-35, M 2 days ago

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    Well this is a group that I definitely needed to join.I adore massive bare boobs and the women that have them.Please add me as a friend here ladies if you like yours worshiped?
    bignatbreastluver bignatbreastluver 46-50, M 2 days ago

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    I am 13 and can't wait to get bigger boobs! I really hope they can hurry the hell up!
    Alex1272 Alex1272 13-15, F 3 Responses Jun 29

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    I really do like boobs but I hate how I have never touched any before! And I'm 19 basically all my friends have felt or grasped them before, except for me!!! I hate my life! I just...
    MilitaryHistoryNerd94 MilitaryHistoryNerd94 18-21, M 3 Responses Jun 30

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    I don't want mine to grow anymore. I hate the look of big boobs
    Cleanandclear Cleanandclear 16-17, F 2 Responses Jul 5

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    How can you wish to have small ones ? I've been teased about being a boy my whole life and I hurt wish I had some boobs
    JadenLangVageta JadenLangVageta 13-15, F 4 Responses Jul 6

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    I DONT like the look of them, I DONT like them, of they're natural that's okay, but giant boobs look nasty, just my opinion, I don't think they look right, I didn't think people...
    Bflyboo14 Bflyboo14 13-15, F 7 Responses Jul 12

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    I have natural boobs but I hate them, I think they look odd
    shannonnicole5189 shannonnicole5189 16-17, F 2 Responses a week ago

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    Worst nip slip in my life. I'm runing down the stairs and I had a bikini on and bikini slips off and my boobs fly right out in front of my 4 year old niece fml
    sexywetles sexywetles 18-21, F 2 Responses 6 days ago

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    Send your boobs ladies 😉
    brickguy67 brickguy67 26-30, M 4 days ago

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    Would love too! Anyone in ontario? Feel free to add and message me!
    jack4770 jack4770 18-21, T 2 Responses Jul 9

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    This is what I would truly love to find at some point!!!!!
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T 2 Responses Jul 12

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    I squealed like real Sissy my first time and many more times after
    boytoy66 boytoy66 46-50, T 4 Responses 5 days ago

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    I am trying to find this test however I can already tell you I am almost if not for sure 100% FEMALE honey! I just love being a pretty little doll and long for the day my Handsome...
    PrettySissyBoiTG PrettySissyBoiTG 26-30, T 1 day ago

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    I love my mom very much. She is still alive at age 76. We love to go shopping, eat out, and just chat with one another. I get my looks and boobs from her. She is a great lady...
    americanmarriedmom americanmarriedmom 51-55, F 1 Response Jun 26

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    I'm not sure if you have tried it but I do love it. Here is my story. About 1 year ago my Girlfriend Janna told me what type of Birthday cake I would like for my 18th, I wasn't...
    ReadorNot ReadorNot 18-21, F Jun 27

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