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I Im a Crossdresser Who Has Used Tampons

Personal Stories, Advice, and Support 490 People

    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...
    mzdivine mzdivine 56-60 9 Responses Dec 13, 2008

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    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...
    angelicamae1 angelicamae1 46-50, T 6 Responses Nov 3, 2009

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    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...
    lachicacarla lachicacarla 31-35 1 Response Apr 29, 2011

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    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...
    deleted deleted 26-30 1 Response Jul 26, 2012

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    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...
    prettydar prettydar 56-60 11 Responses Nov 8, 2008

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    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...
    melissa42 melissa42 31-35, T 6 Responses Jun 21, 2010

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    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...
    lvpntys69 lvpntys69 41-45, M 12 Responses Jul 25, 2010

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    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...
    aksapdopnopmat aksapdopnopmat 36-40 Jan 5, 2013

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    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...
    deleted767 deleted767 46-50 9 Responses Nov 4, 2008

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    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...
    VickyKotex VickyKotex 56-60, T 3 Responses Apr 28, 2009

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    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...
    JoanConstance JoanConstance 46-50, M 6 Responses Jan 10, 2009

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    Tampons - once a month I share the same time of the month with my wife I must wear a tampon and maxie pad be carefull what you wish for
    cdden4 cdden4 46-50, M 7 Responses Sep 17, 2011

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    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...
    wannabeelady wannabeelady 36-40 Apr 23, 2011

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    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...
    xdpaul xdpaul 56-60, M 3 Responses Jun 5, 2011

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    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...
    brandilesalle brandilesalle 31-35 7 Responses Jul 8, 2011

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    I Like Tampon S - I have been useing pads and tarpons for years
    rebar123 rebar123 36-40 1 Response Apr 14, 2012

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    I Love Tampons - I have been using tampons since i was 13 If no one was home i would go to the bathroom and find were my sister kept her tampons and i would put one in then i would...
    billie42 billie42 41-45, M 10 Responses Aug 6, 2009

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    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...
    BarbieB BarbieB 56-60, M 36 Responses Oct 27, 2008

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    I Do - EVERY DAY I TAKE TAMPONS I GOT A PERIOD SOMETIMES
    deaftranny71 deaftranny71 36-40 Apr 23, 2011

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    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...
    cdMartineBeds cdMartineBeds 46-50, T 19 Responses Oct 20, 2012

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    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...
    JackieWould JackieWould 41-45 2 Responses Jul 24, 2009

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    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...
    countrycasuallady countrycasuallady 51-55, M 9 Responses Nov 13, 2010

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    Trying A Tampon - I am a 41 yr old straight crossdresser & I have stomach problems & had surgery. Ever since my surgery I go to the bathroom several times a day. One day at a...
    HighheelWendy HighheelWendy 41-45, M Oct 17, 2013

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    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...
    northerngirl2 northerngirl2 56-60, T 1 Response Feb 11, 2013

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    Tampon Training - In the past I had inserted a tampon and wore it for between 30 minutes and 2 hours. I had mentioned this to my girlfriend / Mistress in the early days of O/our...
    Risky19634 Risky19634 46-50, M 4 Responses Aug 3, 2009

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    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...
    redlace redlace 61-65, M 3 Responses Dec 14, 2011

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    Wow - i am trying playtex 360's ..supers...what a nice feeling
    northerngirl2 northerngirl2 56-60, T 2 Responses Mar 20, 2013

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    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...
    deleted deleted 26-30 4 Responses Apr 12, 2012

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    After... - 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...
    ppaulllmmm511 ppaulllmmm511 41-45, M 3 Responses Aug 10, 2012

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    The String - I love to put tampons in.The feel of it going in and the tube stays in your hand.I like to see the string hanging out.Some times I even wear them to work.I like to put...
    Berrney Berrney 56-60, M 1 Response Sep 6, 2009

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    My First Tampon - I remember the first time I used a tampon or should I say tried to insert a tampon I was about 12 when I first tried to insert a Tampax tampon from a box that my...
    Roxsanne Roxsanne 51-55, T 2 Responses Oct 28, 2011

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    Ice - 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...
    tonytoni tonytoni 31-35, T 2 Responses Feb 26, 2013

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    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...
    SusanWren SusanWren 56-60, M 2 Responses Nov 25, 2009

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    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...
    deleted deleted 26-30 3 Responses Oct 14, 2011

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    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...
    actorman actorman 61-65, M 7 Responses Dec 20, 2008

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    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 MyMonthlyCycles...
    sammi11 sammi11 41-45, T 15 Responses Sep 4, 2010

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    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...
    Ninawetspot Ninawetspot 36-40, T 8 Responses Feb 6, 2011

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    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...
    mielcaliente mielcaliente 61-65, M 2 Responses Feb 25, 2009

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    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...
    saracd4 saracd4 51-55, T 1 Response Jun 30, 2012

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    To Feel Complete - I use both panty liners and tampons at the appropriate time to make me feel the complete experience of being a women.
    pele333 pele333 51-55 3 Responses Jan 9, 2009

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    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...
    mielcaliente mielcaliente 61-65, M 3 Responses Feb 11, 2009

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    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

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    God I Love Them - After giving myself an ennema find the need to insert tampons so I don't leak everywhere.
    Rweistii Rweistii 31-35 Aug 2, 2011

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    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...
    Juilleett Juilleett 51-55, M Oct 9, 2012

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    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...
    tammyie11111 tammyie11111 46-50 Jun 7, 2011

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    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...
    analogguy analogguy 41-45, M 2 Responses Nov 7, 2012

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    I Finally Tried It. - I just enjoyed my first experience of a tampon inside of me. I enjoyed the little string dangling out the end, and feeling it each time I sat down to pee. It...
    Rosabella3 Rosabella3 56-60, M 2 Responses Jan 30, 2013

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    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

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    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

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    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...
    myuser6969 myuser6969 36-40, T 2 Responses Mar 2, 2012

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