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I Im a Crossdresser Who Has Used Tampons

Personal Stories, Advice, and Support 509 People

    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 26-30 1 Response Jul 26, 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 first tampon and napkin when I was very young.  They both made an immediate impression on me.  The three girls across...
    JackieWould JackieWould 41-45 2 Responses Jul 24, 2009

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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 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 46-50 Jun 7, 2011

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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 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 31-35 1 Response Apr 29, 2011

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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 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

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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 friends I was using her bathroom & opened the cupboard for a new roll of tp & noticed her tampons. I thought about it...
    HighheelWendy HighheelWendy 41-45, M Oct 17, 2013

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

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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 believe in any lifestyle except theirs. i`m just learning how to use a computer.i stumbled into this website [thank...
    wannabeelady wannabeelady 36-40 Apr 23, 2011

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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 some water up my *** so they get big.I give a tug on the string and it makes me hard .I give it a tug were ever...
    Berrney Berrney 56-60, M 1 Response Sep 6, 2009

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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,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

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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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    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 56-60, M 36 Responses Oct 27, 2008

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    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 4 Responses Jan 18, 2010

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    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 36-40, T 4 Responses Feb 5, 2011

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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 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 13 Responses Jul 25, 2010

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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 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 26-30 4 Responses Apr 12, 2012

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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 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

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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 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...
    VickyKotex VickyKotex 56-60, T 5 Responses Apr 28, 2009

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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 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 2 Responses Nov 7, 2012

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    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 36-40, T 3 Responses Feb 6, 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 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

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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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    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

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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 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 51-55, T 1 Response Jun 30, 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 had some time by myself to be honest with everyone.  This morning I sit here wearing nothing but panties and a...
    prettydar prettydar 56-60 11 Responses Nov 8, 2008

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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 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 3 Responses Nov 25, 2009

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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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    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

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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 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

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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 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 9 Responses Nov 13, 2010

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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 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 6 Responses Jan 10, 2009

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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 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 29 Responses Oct 20, 2012

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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 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

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    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 56-60 11 Responses Dec 13, 2008

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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, accepting, knowledgable wife who has taught me all the traits to emulate women, from presentation, to walking, standing, sitting...
    deleted deleted 26-30 3 Responses Oct 14, 2011

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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 relationship. Back in May of this year She rang me at work one Wednesday evening and told me that I needed to go and do...
    Risky19634 Risky19634 46-50, M 6 Responses Aug 3, 2009

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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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    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 31-35 7 Responses Jul 8, 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 worry or not
    xdpaul xdpaul 56-60, M 3 Responses Jun 5, 2011

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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 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 6 Responses Jun 21, 2010

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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.com. 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

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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 what a real woman feels during this time.  Oh how I dream of having a menstrual cycle, to be granted the power...
    deleted767 deleted767 46-50 9 Responses Nov 4, 2008

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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 what a sissy **** I am...
    ppaulllmmm511 ppaulllmmm511 41-45, M 3 Responses Aug 10, 2012

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    Wow

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

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    Tampons In My Man-*****

    It makes me feel so much closer to being a woman when I squat a bit and put in my tampon. There is just something that makes me immediately hard feeling filled with the soft cotton plug.
    LittleLisa LittleLisa 61-65, M 5 Responses Aug 15, 2009

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

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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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    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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    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 cause the most horrible, wonderful cramps, so you get more accurate sensations than just wearing the pad or...
    tonytoni tonytoni 31-35, T 2 Responses Feb 26, 2013

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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 mother had. She used Tampax supers in the large blue box. One day I came home from school and noticed that my mom...
    Roxsanne Roxsanne 51-55, T 2 Responses Oct 28, 2011

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