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What came first chastity or crossdressing?

Discussion in 'The Powder Room' started by secretlife, Jun 16, 2017.


Which came first, crossdressing or chastity

  1. Crossdressing lead to chastity

  2. Chastity lead to crossdressing

  1. Was wondering what all you started with? Was it crossdressing that led to chastity, or the other way around.

    i've typically considered myself a "manly man" all my life. Shortly after my Wife and i moved in together, She playfully one evening asked me to put Her panties on before we got intimate. i guess that's what started it all for me.

    Things progressed from there. i admitted my fetish for nylons, and soon after i was wearing my first pair. i started shaving my underarms and chest. Started wearing panties nearly every day, and now my legs are smooth as well. That was about 6 years ago.

    Chastity came up while i was browsing toys online. i showed it to my Wife and She was interested, so we ordered the CB-6000, then later the MM Jailbird. i've now been locked/teased/denied since December of 2016. Although as of writing this only 6 days 24/7. For personal reasons i took a few month break and we're just getting back into the chastity routine.

    Long story short... crossdressing lead to chastity for me!
    Chief256 likes this.
  2. You may be assuming that more than just a few of us are into crossdressing. Some of us may have worn panties for a short time just for fun but the serious CDs usually start off with CD and then add chastity. The ones I knew started CD when they were young and chastity had nothing to do with it until much later in life. Just an add-on to their fetish. I was into BDSM for a few decades and chastity only started a few years ago. The majority of guys who wear chastity devices are single and/or using the devices in a larger fetish like CD, cuckolding, Sissy play, BDSM, FLR, Femdom, etc.. Few of us just do chastity and even fewer do just chastity with no D/s except the power exchange over orgasms. I am the dominant one in my marriage but my wife gets to control our sex life just as she does the running of the household. We all have our areas of responsibility in our marriage based on who is best qualified and not who is most dominant. I do not think, but I can be wrong, that sissies consider themselves as cross dressers since they do not view themselves sexually as men who wear woman's clothes but rather in-between a man and a woman. At least that is my understanding having had a good friend who was into CD and what he told me.
    Tinytina and Mash2214 like this.
  3. In the third-ish grade I became fascinated by bondage after watching a Three Stooges TV episode, didn't even know the word "bondage" existed. After the show I went to my bedroom and tried to tie my hands behind my back........thank goodness my mother didn't catch me! :eek:

    In the sixth-ish grade I became fascinated by lingerie when I saw one of my mothers bras in the laundry hammer and tried it on, didn't even know the word "crossdresser" existed. :D

    Even though I went to Catholic grade and high schools I didn't stumble upon chastity until (before there was the internet) reading about chastity belts in Penthouse Forumn magazine.

    My long story short.... my progression was bondage, crossdressing then chasity. This year I can add butt plugs and penis plugs as well to my kink resume.......woohoo! :p
    Tinytina likes this.
  4. I've known any cross-dressers and transgender folk, both mtf and ftm.

    In general I find I fancy ftm transmen because I respond to what's still female about them, which soon becomes a disastrous misunderstanding that will blow up any kind of relationship, so I steer clear.

    I can and do respond sexually to cross-dressers and transgender women as well as ciswomen (i.e. 'not trans').

    With transgender women, if it is going to get physical I prefer they 'tuck' to avoid my wandering hands finding a cock.

    Which damps my ardour pretty quickly; if all other cues are in place I can treat them as a woman, but that blows it.

    But with cross-dressers I prefer them in a chastity device; otherwise they will masturbate, then lose interest.

    But to address the original question, amongst both cross-dressers, transgender women and other variations, the dressing comes first, chastity later.

    I suspect that it only happens the other way around in a Female Led Relationship or gay, when the Dominant iposes or encourages cross-dressing.

  5. I only acted on crossdressing after exploring chastity. I love skirts and panties. I never tried a bra
    Mash2214 likes this.
  6. Definitely crossdressing first for me. I started wearing female clothes in my early teens (over 50 years ago!) and it has stayed with me on and off since then.

    Chastity has been a fairly recent thing for me and came about as spin-off from my BDSM tendancies. I am very much into self-bondage and wearing a cage just seemed logical as it allowed me to extend my sessions beyond the normal few hours.
    boisub likes this.
  7. Woooooooooooooooooo, NEVER tried a bra?!!

    Please know that I'm not trying to give you a hard time, I'm just surprised thats all @zebra@zebra.

    If you are truly into CDing you really need to give a bra a try. The first time I tried on one of my mothers bras that I found in the laundry hamper I was "hooked" (excuse the pun) for life!! :D

    Most lingerie websites have a page on how to determine your bra size. In my case my true size is 40A and my size when I use my breastforms is 42D. :rolleyes: Yes I know my username is bob40B..........I was a natural B cup until I lost weight. :(

    Most of the time at home and when in public I wear my true bra size. :) When I'm feeling frisky I'll wear my breastform size. :p

    All this fun adds another reason for being locked in a cock cage. Without the cage the resulting tent pole under my shorts/pants would not be good when out in public! ;)

    Attached Files:

  8. Very nice @bob40B@bob40B , but you need take care of getting rid of the chest hair and it would look soooo much better.
  9. You are absolutely right xcitedsissy, before my leg was amputated I kept everything below the nose completely shaved and loved it. Besides shaving was necessary for my legs to look good/right when in public with pantyhose under shorts.

    However, after my leg was amputated I lost all interest in shaving. Its hard enough to keep clean much less shaved so I just stopped shaving. :(

    I actually tried (one) thigh high stocking and even tried using (one) stocking and a garter belt with the right leg garters removed but wearing shorts was not possible with either. It gets wayyyyyyyyy to hot here in Texas to not wear shorts!

    Attached Files:

  10. In my case, I was was fascinated in my early teens by stockings and was incredibly naive. I was really triggered by a 12 year female in one of my classes in 6th grade. She was rather well developed for her age and dressed rather risque for the time and place. The specific event for me was her demonstrating a Ouija board at school. She asked me to try it with her. I know I had to have blushed when she told me to pull my legs up against hers so the board would work. I hesitated and she reached under the table grabbed my knees and pressed them quite tightly against her fishnet clad legs and told me quite firmly to leave then there. I did. I've had a stocking fetish ever since.
    A couple years later, I was at home alone and, like bob40B, I found my mother's bikini in the hamper and got caught by my Dad when I couldn't get changed quickly enough when he suddenly came home.
    Years later, in my middle 40's I learned about chastity devices and made one similar to what was called 'The Bird Cage'. The situation didn't work out due to my selfishness causing me to irritate my wife.
    Fast forward to about 13 years ago. My interest in cross dressing returned. I broke down and asked my wife if I could start wearing panties which led to about 4 years later me starting my complete cross dressing and own wardrobe.
    Then the chastity thing crept back in. I've had an on-going online then real-life relationship of sorts with a C/D Domme and one of her slaves. The one I know best has be self-locking for several years. Guess what piqued my interest? Toward the end of one of our get together parties, Goddess had Gigi handcuff me then they proceeded to put a chastity device on me and sent me nearly 200 miles home with no key.
    May 10th this year made the end of a year long lockup. Ms K/H (my wife) let me out and let me decide when to lock back up which she knew without saying so that I would. Just as I was about to, she asked me if I was wearing my device. I answered no but asked her how long would she like to keep me locked this time? The keys were in her hand shortly. So, I'm due to be unlocked July 1st for time to clean and shave. She's graciously allowing me to play with some of my other devices since I asked her if I could rivet one / glue the lock on it until my vacation which is in mid August and my Birthday is on that last Saturday. What happens after that is going to be entirely up to her. I'm planning a complete surrender to her.
    So TL,DR, yes, in my case, cross dressing led to my chastity.
  11. I started after a few years in chastity my wife wanted me to start wearing panties .I never had any idea I would like it but now panties is all I am allowed I think my wife is bringing out the true me maybe .now I have shaved legs (winter only unfortunately)and painted nails she now has me wearing stockings to work under my business clothes and a nighty to bed ....the the thing I am surprised about is that I really enjoy it ...alot .it has surprised me and delighted my wife I am always looking for more ways to feel more feminin she has even bought home heels that I love wearing around the house
    As I said I never knew but I am so enjoying
    danijean001 likes this.
  12. My journey began with a visit to a Pro Domme who was into "forced Fem" and that was the first time I ever experienced seeing myself fully dressed and made up as a woman. After that, I began to fancy wearing panties in secret until one day when my wife of 32 years caught me in my panties. She challenged me to go for a bra fitting and after I did that, She has continued to feminize me, little by little for the past 5 years. We agreed a couple of years ago to do chastity on the honor system, which worked fine for 3-4 months, until I was "dishonorable". She bought the cages and since then, I have been locked up a whole lot. (I am enjoying it tremendously!
    danijean001 likes this.
  13. In my case its definitely chastity came first as I have no fetish related to any women clothing at all or have any desire to wear them. With chastity I think one gets more horny and kinky so crossdressing is more appealing and arousing. Also being lock up and have to sit to pee kinda makes you less of a man, thus its almost like a natural progression esp when pegging is involved as well.
    danijean001 and Chief256 like this.
  14. This could be lengthy, but I'm at work and I'll make is short. I've had a fetish for panties since I was a teenager and then I would wear a little makeup from time to time or paint my toenails. Once I met my GF who's now my wife of 12 years, one day as a joke I decided to throw on a pair of her panties, to my surprise she loved it. So, since then I've always wore panties. We or I didn't find chastity until earlier this year, we both fell in love with it. My wife has now taken it upon herself to have me wear certain things that are hers especially to sleep in. She likes for me to wear one of her tank tops (Nike, Under Armor) and a pair of shorty shorts of hers. She also likes the idea of me wearing her bra and just recently she wanted me to try on her swim suit. Dressing completely like a female, I seriously doubt that will happen. As for now it's some subtle things in my opinion.
    jack-ie, danijean001 and gary170 like this.
  15. My wife wanted to try chastity s part of her understanding that I am a transwomen. It actually helped her undertsnd the difference between a transwoman and a crossdresser. Clothes may make the woman, but they aren't a fetish for me, they are just what I wear everyday. As you can tell from the picture, after 8 years on hormones, they look kind of natural. And yes, I'm in chastity at the moment, primarily because my wife likes the psychological effects, erections are far and few between, regardless of the steel device.

    danijean001 likes this.
  16. @Chief256@Chief256 It appears to me that you have just enough interest in wearing feminine things that you are ripe for being feminized! I was caught by my wife wearing panties about 5 years ago and,taking advantage of my fetish, She began to feminize me, little by little. While I still don't go out fully dressed very often, I am usually in lingerie (and cage) around the house when my wife is at work. (She lays out my assigned lingerie each morning!) If you are like me, with the casual interest that you seem to enjoy, you will be helpless to resist your wife's feminization efforts! Enjoy the journey, girlfriend!
    jack-ie, danijean001 and Chief256 like this.
  17. I'll be sure to keep you updated! ;)
    danijean001 likes this.
  18. i had been dressing and living as a girl ages and ages before i meet Mistress and i had never hear of a little cage that went went over a willy. When Mistress tooked me to Lady Delias and i meet Her maid well he had got one on so i ask Mistress and that when i had one on.
    danijean001 likes this.
  19. I have been crossdressing since my teen years which increased in my late 20's and chastity devices were always in mind however its not until around 10 years ago I discovered them. I am now 55
    I am now wearing one almost all the time.

    danijean001 likes this.
  20. Like a lot of people I started in my teens. It just kept growing adding more items, panties, bras, skirts and dresses, shoes and more shoes. My interest in bondage started at the same time, I think chastity is just the next step in the process. I think it's so erotic to be bound enfemme
    danijean001 and xcitedsisssy like this.
  21. historically cross dressing came long before the first chastity device barring chains, dungeons and towers. on the other hand eunuchs have been around for 4000 years but i have yet to read about one asking for it to be done until recent history.the desire for adventure, excitement and pleasure are strong driving forces. in this zeal for life i think it probably comes down to exposure and which one did you come across first. my experience with my puck we both filled out sex play slips rating each item 1-5. 4 was only if you really want to i will try to go along. 5 was no way not ever. he gave 5s to chastity,cross dressing and feminization. after much discussion i managed to get him to move them to 4s. since i knew it would be an up hill battle i bought the cage first.(plastic breaks, cuts and pinches.....and lots of blood). so when the metal one arrived he tried to claim his 5 but fair is fair and he did change it to a 4. between break in time, rejecting each for cause and finally realizing that super growers can escape anything i pierced him. one prince albert and one through the middle of the scrotum. 3 weeks heal time and 3 weeks for adjusting. almost a two year process getting him ready for the rest of his life. with a 54 chest with no breasts female clothes are hard to find so muscle removal became more important than the clothes. after finding out his coat size before the army i knew he had to and could lose at least ten inches of muscle. two years on estrogen got the lower chest to 43 and now i can dress him. still his all natural breasts are 54. weird thing is a 44 c is tight 44 d is loose and the charts say 44 g. the reason i went here is finding female clothes for a 6'2" 290 lbs lady is impossible . well tents work. at 205 18s and 20s fit even some 16s but the length is a killer. long corsets are 17" long 18" can be found. he needs 22".
    as much trouble i had with cages i thought clothes would be a cinch ( another subject unto itself) still working on his weight but 150 is the goal and a size 12 dress would be great(puck says a ten at 145). puck has pointed out many time that i need 8 inch heels and he wears flats to help him not stand out. for a lot of guys clothes are out of their reach. the cage comes first.
    Sub Dave and danijean001 like this.
  22. i love shoes as well and if i cud i wud have lots and lots and lots.
  23. I really hadn't thought that I cared that much for crossdressing throughout my life. My mistress and I got into chastity a couple of years ago and slowly as though it's trickled into my being I have a huge desire to live out my sissy fantasy. I don't care to be dressed as a girl just for the sake of looking like a girl (not that I'd be convincing) my desire moreso is in the form of pvc/satin sissy maids uniforms and being treated like a sissy maid.
  24. Well it started with Chastity (about 10 years) and now wearing ladies underwear. (but only recently)
    Not sure where I am in the spectrum of things.
    I have just strange thoughts.
    Is it Crossdressing, transvestite, exhibitionism. gender fluid, sissy .maid
    This is day three of wearing knickers. Yesterday I went out shopping, not to the local shops. Whilst out I was talking to the lady shop then I had the urge to turn around and bend down to look at the bottom shelf, there by revealing the back of my trousers and underwear waist band. She would then see it and consider “What is he wearing?” I did not do this but I considered it.
    I also later at home was alone and needed to do some ironing, Should I try on a skirt at the same time? But I did not.
    If my keyholder asked me to dress as a maid , I would.
    I am sexually excited by my wife, by females .
    If we where on holiday and she wanted me to dress as a female, I would
    I also was thinking about my smell, would I wear ladies perfume ? Yes if my wife wanted it , both for work and at home.
    Wear stockings ? Yes if she wants it.
    Would I swap my nightwear for ladies nightwear (but not obvious ) – I think I will

    My keyholder saw me clearly in my Spider man knickers, with my hairy legs. “do you want me to shave?” I asked. “No, I don’t want you to look like a girl”. She replied. My reply was “I would always love even if I did (shave) I would still fancy you”
  25. i rather has Superman i do. i don't like Spider-Man very much.

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