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I Want to Be to Be Crossdressed and Tied Up

Personal Stories, Advice, and Support 1,253 People

    Being Silly

    I told a story about how my HS girlfriend dressed me up totally for the first time but wait there's more. A week or two later she had me try it again. This time she brought me some silky nylon panties an lacy bra. The same pair of black shaper pantyhose and the same heels. She...
    deleted deleted 26-30 8 Responses Jun 17, 2011

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    Another short story about my fantasy s I

    wanted to come home from work one day. Have a shower. Then get dressed like a secretary , but was not sure how my wife would react. It might be a little to far , so the night before I started to tell her. I wonder what it feels like just to sit around on the sofa , and make a...
    glenn56 glenn56 36-40 Mar 21

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    I remember a day we were out in Greece ,

    my wife told me she was going for a long walk along the beach with her friend , ok I said how long will you be , I'm not to sure it's a very hot day. Ok I said no problem. She left the house at 12.30 , it was around 6pm when she came back. I said you have been a long time...
    glenn56 glenn56 36-40 Apr 4

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    This happened a few years ago ,

    I took a week of work but my wife didn't , so she asked me if I could pick her up at lunch time so she could come home for a hour just to get away from work ok I said no problem ,, which then got me thinking ,hmmm so I asked my wife if I was to pick her up at 12.45 pm lunch time...
    glenn56 glenn56 36-40 3 Responses 6 days ago

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    I remember a time my wife tied me up ,

    one Saturday afternoon , she told me to wear my pink bra and pink knickers , white stockings and suspender belt , navy blue pencil skirt and white shirt / blouse with a black tie , and my back short wig. And then to go into our upstairs attic room if I wanted to be tied up and...
    glenn56 glenn56 36-40 1 Response Apr 18

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    She Tightened The White Cloth Gag More And As I Heard Her High Heels Click, She Said .. PART I

     As I sit here, tied tight to a high back chair totally en femme, I ponder the processes that lead up to this moment. I am all en femme in white school tennis pumps, tiny white cotton sport socks, honey colour support nylon tights running up to my white polyester tennis skirt...
    stacytiedandgagged stacytiedandgagged 41-45, M 7 Responses Feb 8, 2013

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    I Wish I Was This Lucky

    I wish that I was this lucky to have this happen to me, to get all dressed up in one of my best looking dresses get my hair done do my makeup all pretty like and put on my favorite pair of tights and heels and play a helpless damsel in distress. But unfortunately its just another...
    glasscitycd90 glasscitycd90 22-25 5 Responses May 18, 2013

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    Debutante In Bondage

    My favourite tied-up fantasies involve being a woman of wealthy background, or good family, kidnapped and tied up by ruffians from the lower orders, for example pirates or bandits, or ruffians who lurk for the unwary. One recurring fantasy, inspired by the book Miss High Heels...
    Silkendreams Silkendreams 46-50, M 6 Responses Sep 27, 2010

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    I remember. One sat night asking my wife

    if she would tie me up when it was time for bed after our weekend drinking. Session. She agreed. I had bought a few items over the previous weeks of the Internet. , a ball gagg and latex zip and tie gimp hood and blindfold. It came to around 10 pm and my wife said listen...
    glenn56 glenn56 36-40 Mar 5

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    I remember a few years ago begging my wife to

    tie me to the wooden single bed upstairs in the attic for a few hours. Which she agreed , I got dressed. In purple silk suspender/ belt. And purple knickers then black stockings with a pattern and a purple satin bra , then a leather skirt , and decided. I with shirt which I...
    glenn56 glenn56 36-40 1 Response Mar 5

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    Hi. This happened on sunday afternoon ,

    a sort of test run for this weds , I asked my wife on sunday if she would finish tying me up if I did most of it myself , while she cleaned and did our sunday dinner , yes she replied but not in here , downstairs in our friends part furnished appartment. Take it or leave it...
    glenn56 glenn56 36-40 2 Responses Jun 9

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    My wife was going to tie

    and gagg me , and she leaves all my clothes set out for me to wear , but I asked if I could pick out my clothes this time , ok she says , so I decided I wanted to be a navy wren officer , so I put my white suspender/belt. And black seemed stockings , followed by white knickers...
    glenn56 glenn56 36-40 Mar 10

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    This happened just last night ,

    after 3 months of nothing. And also getting rid of lots of my old blouses and skirts. Getting a bit tatty , I asked my wife around 4pm if she minded if I tried to tie myself up sat on the chair against the wrought iron bed , you can do what you want but don't ask me. I'm not...
    glenn56 glenn56 36-40 Mar 18

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    Tied Up, A Friend To The Rescue Sort Of...

    Having crossdressed since I was 5 it was just a usual day when I would be dressed around the house. With 2 sisters and an accepting mother cding just became a way of life. Ater watching several TV shows and movies with women being kidnapped and tied up I started to play with it...
    femboy4u femboy4u 22-25 8 Responses Mar 27, 2011

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    Locked Up, The straitjacket style :D

    This is what I recently found out as soon as I bought myself several pieces of chain along with padlocks so that I could chain myself up. After being trapped in chains that were keeping my stilettos locked on my feet, cuffing myself up anyway I could think of (including the...
    lockedheels lockedheels 31-35, M 2 Responses Nov 29, 2013

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    So I was asked to take some pictures the other

    night to show off my new shoes. I have a pair of patent leather 4 inch stiletto pumps with locking ankle straps. I was told to get a pencil skirt so I did. I put on some black thigh high stockings with garters. Pencil skirt. Corset. A button down shirt. And a corset. My...
    Photogeek47 Photogeek47 26-30, M 2 Responses Jan 1

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    Sissy Fantasy

    This has never happened to me, but I would like it too. I used to work in a place where I had access to accomodation rooms, I would sneek in from time to time and take some women's tights from their drawers, this one woman was soo sexy and one day when in her room going through...
    andyhos andyhos 36-40, M 4 Responses Oct 14, 2009

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    One time my wife tied me up ,

    I asked her if she. Would go out and buy me a nice outfit to wear , which she agreed to do , but I didn't want her to tell me what it was she would buy , ok was her reply , that weekend she went shopping , omg I was so excited ,and coudnt wait , it was a week later on a Friday...
    glenn56 glenn56 36-40 3 Responses May 21

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    My Drawer Of Kinkiness :)

    Hi all, I just received some new items and would like to share with all of you what my "intimates" drawer contains. I am serious about bondage and crossdressing so my drawer includes both! This is the stuff that I have been able to buy so far in the country I moved into a few...
    lockedheels lockedheels 31-35, M 2 Responses Jul 30, 2013

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    I have always had a interest in being tied up

    and gagged like in the movies when a smart spy or women detective gets kidnapped. , my wife. Does tie me up but only around once or twice a month which is ok. Because I get very excited when the time comes around , plus she always promises to make it different and also very...
    glenn56 glenn56 36-40 1 Response Mar 15

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    Helpless

    I am lying on the mattress.  Although there is a slight chill in the night air, I am mostly lying outside the covers.  With my wrists bound I have been able to do little more than wriggle my feet and part of my calves under.  I am aware of the chill, but it is not...
    clairemeredith clairemeredith 46-50, T 13 Responses Sep 25, 2009

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    Another time I have had a great day tied up

    and gagged by my wife and wished I hadn't have asked her , I always want to try. Different ways to be tied up very tight so I can't move. I know my wife can do a. Great job of it to the high back chair but it gets a bit boreing just sitting there unable to move just looking. At...
    glenn56 glenn56 36-40 1 Response Mar 20

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    My wife ties and gaggs me at least

    once a month but she needs to go shopping at my expense while I'm tied up because she cannot stand being in the house at the same time , so I agreed On the day it came around she told me she had set all the clothes out on the bed and told me to get ready. But before I do to put...
    glenn56 glenn56 36-40 2 Responses Mar 3

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    alexiswcd alexiswcd 56-60, T 1 Response Jun 21, 2014

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    Hello , this is a sort of pre story ,

    this is going to happen later tonight all going well , let me give you the picture , My wife's agreed to tie and gagg me before she goes to bed tonight , we've agreed on the sun lounger on top of our bed in the spare room , it could be around midnight , 1am or 2am later the...
    glenn56 glenn56 36-40 Jun 10

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    Tied And ******

    I have a friend with benifits, she and I have been friends for some time now and have had many sexual experiences together.One night at her place, she knows of my crossdressing, she told me to go to the bedroom, she had things laid out for me to wear. She had said "don't ask...
    kattie2121 kattie2121 51-55, M 6 Responses Jun 21, 2013

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    She Tightened The White Cloth Gag More And As I Heard Her High Heels Click, She Said...Part lll Five Hours Later..

    It has now been five hours since I was by my own conviction and abidence put into extreme bondage, chairtied and already crossdressed in a sexy tennis outfit chosen by the very assailant / accomplice who crossdressed me many hours ealier and subsequently bound and gagged me so...
    stacytiedandgagged stacytiedandgagged 41-45, M 8 Responses Mar 9, 2013

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    Continued from last story ,

    So my wife's last words to me were I'm going to give you the option yes or no , stay or let you out I'm only going to ask the once , then I'm off back to my friends for a good night of dancing drinking , chatting , plus I have a little surprise for you if you do decide to...
    glenn56 glenn56 36-40 1 Response May 23

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    This is my story about the best bondage treat

    I've ever had My wife said to me early one morning over breakfast that she would tie and gagg me all day , if I give her £75 to go to town to buy a nice perfume she had seen , and that she would let me wear any of her clothes I wanted. ( my wife works has a pa at a law firm...
    glenn56 glenn56 36-40 May 3

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    Femme , Bound and Gagged Mmm

    omg its so hot to be dressed totally feminine and be tied & gagged.....have had this happen a few times when i was younger & still dream about it. bondage & crossdressing seem like a wonderful and erotic blend. wearing satin panties , smelling of perfume , leather & ***. you...
    tessa tessa 41-45, T 29 Responses Sep 18, 2009

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    Since Forever

    I've always loved watching these beautiful women on tv who always got captured by someone and where tied up. I have wanted to feel what that was like the wear a sexy dress pantyhose heel and be all tied up to a chair or something of that nature and experience the thrill and...
    glasscitycd90 glasscitycd90 22-25 5 Responses Oct 1, 2012

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    Serious About Being Helpless!

    I just received my latest kinky toy today. A pair of high quality lockable wrist cuffs made of durable hard rubber. They are a serious accessory for bondage enthusiasts. You can see then in the picture, they are adorable and really effective in keeping you restrained securely if...
    lockedheels lockedheels 31-35, M 5 Responses Aug 1, 2013

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    This happened the other night around 8.

    30 pmI asked my wife if she would tie me up and leave me all night tied up , she said she would. But first we had to nip out while she bought me a new bra , and some tape , which we did , she said she also had a good idea on the best way to tie me up , wow I couldn't wait , hours...
    glenn56 glenn56 36-40 1 Response Apr 10

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    One Saturday night me

    and my wife was watching tv after we had eaten our Chinese takeaway. And we were relaxing having a few drinks and watching tv. We were trying to watch a programme and our phone was ringing every 5/10 mins it was my wife's sister she was uptown. Celebrating her birthday. And...
    glenn56 glenn56 36-40 Mar 4

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    I remember one occasion a

    while ago. I asked my wife if she would once again tie and gagg me , her reply. What am I going to do all day with myself it's very boring knowing you are in the other room plus you know I don't like it. , ok I say why can you not go across to town ( my doesnt drive and the...
    glenn56 glenn56 36-40 Mar 7

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    I wanted to try some self bondage ,

    so I asked my wife if she minded. She told me she didn't mind provided I didn't ask her ( she will only tie me up once or twice a month , she also told me. That I was not to do it in our apt but downstairs in the next block at ours friends holiday rental apt ( which is empty...
    glenn56 glenn56 36-40 Apr 15

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    My wife hates tying me up ,

    always I have to almost beg her , or promise her somthing , , I can ask her around 11/12 lunch time and she will say no no no , then when it gets late in the afternoon it's always the same. Ok then if you want me to tie you up and it means that much go and get yourself ready...
    glenn56 glenn56 36-40 2 Responses Apr 21

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    One of the first times I asked my wife to tie

    me up , was a few years ago , I asked her to tie me up and gagg me in the garage to the multi gym I owned at the time. She agreed but at the time she worked as a carer at a old folks home across the way , and didn't finish her shift UNTILL 10 pm , but she would do it then , wow...
    glenn56 glenn56 36-40 May 24

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    Dressed N Tied

     The last time i did this, i was dressed to the 9's. all the lingerie, heels, hose, panties, everything. and i had the house to myself. i got my ropes together. for the ankles, wrists, knees ... .i went into the spare bedroom, and closed the door. then tied my ankles, with...
    Nita427 Nita427 56-60, M 15 Responses May 10, 2010

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    My Brand New Skyscraper Stilettos (Locked On Of Course)!

    A few days ago I ordered a new pair of high heels. I already have one with a 5-inch heel but I have left these beauties back at my hometown, sealed and hidden at a very big abandoned camp, thousands of miles away from the place I live now. I had already started to really miss the...
    lockedheels lockedheels 31-35, M 5 Responses Nov 6, 2013

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    "I Want to Be to Be Crossdressed and Tied Up"

    Yes, yes, yes !!!!! I often tie myself up with ropes or chains and locks when I'm cross-dressing and the rush is unbelievable, but I just know I can get myself loose. I certain if I was secured by someone else the experience would be mind-blowing. Oh, I hope and hope for the...
    01Chrissie 01Chrissie 41-45, T 20 Responses Sep 18, 2009

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    My wife agrees to tie

    and gagg me but only once a month which we both agreed due to her not liking it very much but she knows I do , . so on Monday it was my time as I like to call it , but because it's only once a month I asked her to make sure 100% that when she did it that she would do a proper...
    glenn56 glenn56 36-40 Oct 1, 2014

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    My wife hates tying me up ,

    , and so came up with the idea that she would do it providing i wasn't in the same house when she does it. , she goes out , but the last time she did it she suggested. She does it in our friends apt. ,( they live in France ) and we look after the place for them. , its a 2 bed...
    glenn56 glenn56 36-40 1 Response Mar 4

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    My wife surprised me early one morning with a

    suggestion , that she would give me my best ever bondage session if I give her £75 to go to town and buy a bottle of perfume ,she liked , My wife's said if I agreed she would allow me to wear any f her clothes I wanted from her wardrobe ( wow I was so excited ) My wife works...
    glenn56 glenn56 36-40 1 Response May 3

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    A Littl Adventure

    I wasnt dressed by sombody else but i was deffantly dresed I wore suntan pantyhose a black likra pair of pantys with my **** back between my legs to hide any vestages of masculinty  next was a black slip with tons of lace a black longline bra i wore that over my new wast cincher...
    dawn40108 dawn40108 41-45 7 Responses Dec 8, 2011

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    Last Night

    Last night I was all alone in my house, so I decided to spice things up. I started by gathering everything I would need to have a fun night. That included a frilly thong, leather gloves, and a leather trench coat along with my nipple clamps, ropes, and binds and of course my...
    clarebythesea clarebythesea 18-21 3 Responses Apr 21, 2013

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