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I Im a Crossdresser Who Has Used Tampons

Personal Stories, Advice, and Support 481 People

    Being Girlie Boy

    after my mom caught me in her things she told me I am going to learn what a girl goes thru and she said one thing a girl goes thru is having a period every month and your first month is now (at age 13) I had to use a tampon and pads for one week and every month for one week...
    angelicamae1 angelicamae1
    46-50, T
    6 Responses Nov 3, 2009

    Dressing Up And 'sharing' Menstruation With Siblings

    I was started back into dresses when I was just turning 14, and my mother and stepfather made sure that my sister and stepsisters were aware, it was not to be a secret in the house. About a year into this life, my sisters were complaining to my mother that I got to have all the...
    analogguy analogguy
    41-45, M
    3 Responses Nov 7, 2012

    I Do

    deaftranny71 deaftranny71
    Apr 23, 2011

    Today Was My Period And I Used A Tampon For The First Time

    today i used a tampon for the first time to day i used tampax pearl Regular Unscented and ky jelly i left it in for the maxim time it seed pn the instrshons. then i changed it. the felt so felt so good i c** so bad i loved it to night i puting in a over night tomarow im...
    bigboy90000 bigboy90000
    22-25, M
    3 Responses Oct 26, 2010

    Two For One

    something happened last evening. it caught me by surprise. my wife was changing my tampon when suddenly it felt bigger. i told her it felt different but she said it was my imagination. when she finished i turned around. my wife was smiling and holding two applicators. can you...
    mielcaliente mielcaliente
    61-65, M
    2 Responses Feb 25, 2009

    Being All Girly

    i got my first pads and tampons for my 13th b-day mom and sis took me shopping and i got to be a big girl i loved it
    sissykrisb sissykrisb
    51-55, T
    1 Response Dec 25, 2012

    My Limited Experience In Crossdressing

    I live in a small community that i grew up in and information on this is nonexistent here . they don`t believe in any lifestyle except theirs. i`m just learning how to use a computer.i stumbled into this website [thank...
    wannabeelady wannabeelady
    Apr 23, 2011

    Lession Learned

    One day I came home pissed off about something. I started bitchin to my wife chewing her *** out. That went on for a little while. Then she walked over a took my hand and took me to the bathroom she was acting all sexy and such. She took my pants down and (I did'nt see her get it...
    deleted deleted
    2 Responses Apr 12, 2012


    Here's a little trick I learned for your male visits from Aunt Flo. Slide and ice cube up inside, followed by a tampon. The tampon with absorb the water and the ice will cause the most horrible, wonderful cramps, so you get more accurate sensations than just wearing the pad or...
    tonytoni tonytoni
    36-40, T
    2 Responses Feb 26, 2013

    I Like Tampons

    I have driven to work wearing panties tights and having inserted a Tampon. Then when at work I would wait for about 4 hours before going to the gents and changing my Tampon.  It feels so feminine to use Tampons hat i wish I was able to use them more often...
    SusanWren SusanWren
    56-60, M
    1 Response Nov 25, 2009

    I Cant Sleep

    to all sissy how uses tampon im haveing a hard time using tampon when i go to bed i use pads at night but i want to use tampon at night can any one help me
    bigboy90000 bigboy90000
    22-25, M
    Apr 22, 2011

    Do It For Your Partner

    Hi all U sweeties : I wear and enjoy wearing tampons , the bigger the better for me. There R so many ways to enjoy them , putting them in and taking them out is one thing, having a little pink bow or a pompom of nylon crinoline tied to it is wonderful as it just hangs next to...
    tammyie11111 tammyie11111
    Jun 7, 2011

    The Real Deal. Or As Close As It Can Get.

    The is a true and brief story about my best tampon experience I ever had.  I was around 6 when I first got interested in women having a period.  It fell by the way side until I was about 22.  My friend and I rented a house ans his sister Lisa was a room mate as...
    sissyfootboy sissyfootboy
    31-35, M
    3 Responses Jan 18, 2010

    I Love The Feel Of Tampons

    Just cane back from the store with abox of tampons going to start my period tonight and see how long I can wear a tampon. I usually get very horny and pull it out right away but I'm going to try to keep it in overnight at first then wear them during the day for a full 5 days wish...
    Ninawetspot Ninawetspot
    41-45, T
    3 Responses Feb 5, 2011

    Finally Did It

    I was minding my own business and exploring EP and came across this group. Since I had not tried it I did not dare to join the group, for it is a group of gals who have tried it and are enjoying it. I read almost all the experiences by noon and got inspired to try it. So I...
    myuser6969 myuser6969
    36-40, T
    2 Responses Mar 2, 2012

    A Tampon Virgin

    After reading about using tampons and replies from my friends. I now longer am a tampon virgin. My first experience today. I woke up this morning checked this sit emails and stories etc, went up stairs took my woman’s jeans off, pulled my panties and pad down, opened...
    JoanConstance JoanConstance
    46-50, M
    5 Responses Jan 10, 2009


    i am trying playtex 360's ..supers...what a nice feeling
    northerngirl2 northerngirl2
    56-60, T
    3 Responses Mar 20, 2013

    Feeling Complete

    Whenever I travel I put a panty liner in my panties and I carry a tampon as it usually is that time of the month or so I dream.  I feel a small part of what a real woman feels during this time.  Oh how I dream of having a menstrual cycle, to be granted the power...
    deleted767 deleted767
    8 Responses Nov 4, 2008

    My Period Day 1

    Slept with my tampon in all night was kinda uncomfortable but now that I removed it I'm missing the full feeling will pick up some pads for day and put in a tampon tonight also downloaded an app for my iPhone to keep track of my period. Please do it if you havent it really does...
    Ninawetspot Ninawetspot
    41-45, T
    2 Responses Feb 6, 2011

    I Like Tampon S

    I have been useing pads and tarpons for years
    rebar123 rebar123
    1 Response Apr 14, 2012

    Nothing Better!

    I just love the feeling of having a tampon up my sissy slutty *** hole! There's nothing better than parading around the house dressed in sexy lingerie, slutty CFM heels & a tampon up my ***! Makes me feel so naughty & fem! After I insert it, I fill an ear wax bulb-type syringe...
    saracd4 saracd4
    56-60, T
    1 Response Jun 30, 2012

    Yes I Wear Them.

    It started as a dare to myself many many moons ago. Of course it hurt but like everything else it gets easier with time and practice. I use them once a month for a week, I'm sure we all know what week. Love the feel of walking and sitting and getting a friendly reminder that...
    lachicacarla lachicacarla
    1 Response Apr 29, 2011

    God I Love Them

    After giving myself an ennema find the need to insert tampons so I don't leak everywhere.
    Rweistii Rweistii
    Aug 2, 2011

    Text From My Mistress

    I got a text from my Mistress this morning telling my period was to start today, so I had nice shower,put my enema attachment on the shower head and cleaned myself out fully. Found my super plus tampax in my sissy *****, dressed in my white regulation cotton gym knickers with...
    Juilleett Juilleett
    51-55, M
    Oct 9, 2012

    Love Tampons

    I am a crossdresser and when I am dressed in my bras and panties I always have a tampon up my ***. I figure that if I am going to dress the part, then I must play the part. Having a tampon up my *** makes me feel like the complete woman that I am emulating. I just love the feel...
    BarbieB BarbieB
    61-65, M
    34 Responses Oct 27, 2008

    Love The Feeling...

    I'm a crossdresser who has been using tampons since an early age (around 13-14 when I first tried). Although tampons with applicators are fun, I find it easier to use a brand like Lil-Lets that are inserted using just a finger, as they can be lubricated along there whole length...
    melissa42 melissa42
    31-35, T
    5 Responses Jun 21, 2010


    Love putting a tampon inside my sissy ***** after 5 or 6 (or more) men have ****** me and *** inside me...holds that hot *** inside so much longer I love it...reminds me what a sissy **** I am...
    ppaulllmmm511 ppaulllmmm511
    41-45, M
    3 Responses Aug 10, 2012

    Night 2

    I just put in my tampon for the second night it feels less uncomfortable it feels more natural. I should have one more night to my period,will be wearing my pad tomorrow to work.
    Ninawetspot Ninawetspot
    41-45, T
    8 Responses Feb 6, 2011

    Counting Down The Days

    I finally did it. I chose the first of September to throw down the gauntlet and commit myself. On 1 September I signed up on the website My first period is due on 15 September. I’ve booked myself into a totally secluded cabin in the mountains for the...
    sammi11 sammi11
    41-45, T
    15 Responses Sep 4, 2010

    Where Do I Start?

    I  absolutely LOVE the AGONY and the Ecstacy  of using a  TAMPON! The Agony,,,,,inserting the Tampon The Ecstacy?.......So good a feeling!!   All I want now is a wig!! Love you, girls!....Satire!
    mzdivine mzdivine
    11 Responses Dec 13, 2008

    My Period

    So here's my simulation of my "menstruation". It's fun to feel more feminine. I have a regular period every 28 days. It takes 5 days from Monday to Friday. Usually I wear regular pads or maxi pads. I use an average of 4 per day. In the hardest days I wear maxi pads but put a...
    deleted deleted
    Jan 5, 2013

    The Cost Of Discovery

    In the office suite in which I work we are blessed to have our own bathroom, one that is only used by eight people. It is nicely done room and includes a large vanity with storage underneath. Understandibly the women in the office quickly took to storing thier feminine products...
    deleted deleted
    1 Response Jul 26, 2012

    Crossdresser Who Wears Tampons

    Greetings and HIGH HEELSI'm a "newbie" in here so bear with me please..I'm a long time married crossdresser, with a very supportive, understanding, accepting, knowledgable wife who has taught me all the traits to emulate women, from presentation, to walking, standing, sitting...
    deleted deleted
    2 Responses Oct 14, 2011

    Even As You Read

    i learned about tampon use when i was 12,..i had been wearing panties and dresses for a while, then when i was 12, i was given a training bra by my oldest cousin,and after i put on my panties and my new bra to model a new dress for a girl two blocks away,my older sister handed me...
    northerngirl2 northerngirl2
    56-60, T
    3 Responses Feb 11, 2013

    Wife Chose For Me

    Once when my wife was in her time of the month, I was lounging in my panties and bra. She called me over and asked me if I really wanted to feel like a woman for the afternoon. I said immidiatly said yes. She asked me to lower my panties and to bend over. She inserted one of her...
    mielcaliente mielcaliente
    61-65, M
    3 Responses Feb 11, 2009

    A Loop

    What I enjoy doing is pressing the tampon out until it is about to come out giving myself some extra string to tie a small loop that I then tie around my **** before tucking it back and inserting the tampon. It takes some practice but when you get a little aroused and you feel...
    brandilesalle brandilesalle
    6 Responses Jul 8, 2011

    Full Filled

     There are times that I want to feel more in touch with my femininity, like now.  I wanted to write this entry a few weeks ago but needed to wait until I had some time by myself to be honest with everyone.  This morning I sit here wearing nothing but panties and a...
    prettydar prettydar
    11 Responses Nov 8, 2008

    Are Any Tampons Much Bigger Than Others?

    i am a sissy boi who like putting things in her boi-****. i also love the feeling of holding a 2 to 3 quart enema. Does anyone know of a brand of tampon that is large enough for this purpose?
    redlace redlace
    61-65, M
    3 Responses Dec 14, 2011


    I enema nearly every day, as I love feeling clean & fresh inside. I always use a tampon aftewards to prevent leaking & staining my panties. If I've done multiple enemas, I'll also use a pad.
    AshKat AshKat
    41-45, T
    4 Responses Dec 5, 2009

    Tampon Lover

    Using a Tampon in my sissy **** maked the wearing of panties more pleasureable!
    photousa photousa
    61-65, M
    1 Response May 25, 2012

    How I Started Using Tampons

    I was 13 when i experienced my first tampon, though i wasn't expecting it. My uncle had for some time snuck into my bedroom on nights he looked after me for his sister. While he thought i was asleep, he would slip my pyjama bottoms off and pull on a pair of nylon full panties...
    cdMartineBeds cdMartineBeds
    46-50, T
    25 Responses Oct 20, 2012

    I Should Have Known!

    As one of the others said: I was the not only to want this.  If you can think of it someone else has done it at least in this world.  I saw my first tampon and napkin when I was very young.  They both made an immediate impression on me.  The three girls across...
    JackieWould JackieWould
    2 Responses Jul 24, 2009

    Going Modern

    however I don't particularly like them. I am more of an old fashioned girl who likes the feel of a thick pad. I started on belted napkins and prefer them. Two years ago a freind was on her period and knew I was also. She asked if I had ever used a tampon and offered me one to try...
    deleted deleted
    2 Responses Apr 28, 2009

    First Time

    I remember the apprehension I had the first time I decided to try a tampon. I was about 16 or 17 and had decided I just had to find out what one felt like. Went to the bathroom where mom kept her supply, took one out and pulled off the paper cover. It was a supersize, and I...
    lvpntys69 lvpntys69
    41-45, M
    11 Responses Jul 25, 2010

    Only Once

    I have only used a tampon once up my man ***** as I always worry that the cotton thread will pull away from the tampon leaving it where it should not beam I right to worry or not
    xdpaul xdpaul
    56-60, M
    1 Response Jun 5, 2011

    I Thought I Was Weird !!!

    Here is silly little me thinking I was the only one to experiment with tampons. Yes it is a nice feeling and makes you feel more 'complete',when dressed. I would think that perhaps all who commentate on this experience are crossdressers. Lets stick together girls.. The only...
    actorman actorman
    61-65, M
    7 Responses Dec 20, 2008

    It Is Just The Right Thing To Do

    I have been using tampons for many years now. When I started, I experienced some discomfort, and bleeding, but it was worth it. Now, when I haven't got one in, I feel dreadfully insecure and, in some repects, almost naked. I would recommend tampon use to any other sissy...
    countrycasuallady countrycasuallady
    51-55, M
    8 Responses Nov 13, 2010
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