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  1. #1

    How old were you when you started cross dressing

    I started putting on my mothers clothes when I was around 13, even when I was younger I liked to pretend I was a girl but not in a sexual way. I still like to put on my wife's panties occasionally, just for my own entertainment.

  2. #2

    Re: How old were you when you started cross dressing

    Quote Originally Posted by Beddibi View Post
    I started putting on my mothers clothes when I was around 13, even when I was younger I liked to pretend I was a girl but not in a sexual way. I still like to put on my wife's panties occasionally, just for my own entertainment.
    I was young -- certainly under 10, but don't really know what age I was. The earliest recognition of my desires was a strong attraction to women wearing nylons. I wanted to touch their legs, and, eventually, to wear them myself. It's so much a part of my sexuality that I wear panties and pantyhose virtually all the time these days. (unless I'm nekkid!) For me it's both about sexuality and expressing my feminine side.

    Aside from all of that, I've lived the life of a typical man, worked in a traditional man's occupation, with a strong mechanical aptitude and athletic ability. I'm a fairly ordinary husband, dad, uncle, grandfather. And now, at this late stage of my life - a bisexual with a fondness for sucking cock.

    Just your average guy next door...

  3. #3

    Re: How old were you when you started cross dressing

    Around 12 I used to try on my grandmother's and aunts underwear then around 16 I had a friend who was a jehovahs witness and he would go out to service every Thursday night and his sister would leave her bathing suit and lingerie on the clothes line. After they left I'd go in the back yard and put her clothes on in their shed.one day a neighbor saw me in a bikini and asked for a kiss before going back inside

  4. #4

    Re: How old were you when you started cross dressing

    I was 8. I had always liked girl things better and was confused about being a boy even before then. The first time I remember thinking I should have been a girl was before I went to first grade so I imagine 4 or 5.

  5. #5

    Re: How old were you when you started cross dressing

    I always wanted to be female more, the first time I actually tried something on was about 11-12 years old, my grade school girlfriend did the makeup..hehe I have to give kudos to the folks in the local area for being supportive because I actually won a church Halloween party costume competition. ..once puberty hit though it was just much easier to live with the factory installed equipment.. I am a lot happier in my skin now than I was back then, a lot of it had to do with not having very good male role models growing up - if being a drunk, abusive asshole is what it meant to "be a man" then I wanted to be as far away from that as possible...well that and I loved the way other guys treated women, not knowing much about adult life I was a little jealous and thinking the grass seemed greener on the other side. I finally met some supportive male friends of good character and learned enough about life to feel worthy just for being me. Of course women say the same thing .. they resent not having more freedom. There's definitely something there. I think it boils down to the idea that as soon as you put a label on something you set a boundary; nobody really likes to be labelled while they are still trying to figure themselves out and as far as I'm concerned nobody deserves to be a prisoner for life just because of their innate characteristics. Check this out.. http://www.patheos.com/blogs/dispatc...conservatives/ I guess at first I might be a little weirded out too, but from my own experience I don't think a trans person would be sexually attracted to someone of their own gender any more than any other person of that gender. To me a MTF person may (at least temporarily) have male genitalia but they are psychologically female..and there now professionally recognized medical tests to prove it. Of course try telling that to little Susie's mom. I guess the easy thing to do would be to erect a standalone unisex bathroom but they won't want to do that either. Gnostic thought deals a lot with duality and trying to find a way back to our original nature.
    Last edited by elian; Feb 1, 2016 at 7:40 PM.

  6. #6

    Re: How old were you when you started cross dressing

    Of course cross-dressing and true transgender feelings are two different things - some folks are perfectly happy to be 100% male but just enjoy wearing women's clothing (or vice versa) ..

  7. #7

    Re: How old were you when you started cross dressing

    I was a little late in cross dressing although I fantasized about it. I was nearly 40 before I dressed as a woman.

  8. #8

    Re: How old were you when you started cross dressing

    I was around twelve when I first tried om my older (16) sister's panties. The sexual thrill this gave me was amazing and I have been wearing panties when I can ever since. I also like most any lingerie. I dont want to be a woman but wearing panties still turns me on. I also love wearing them when having MM sex and love it when my sex friends also wears. It's a great fetish for those who get turned on by it. It's not a must and I have had many MM sex when not dressed.

  9. #9

    Re: How old were you when you started cross dressing

    Quote Originally Posted by silkyhoselover View Post
    I was young -- certainly under 10, but don't really know what age I was. The earliest recognition of my desires was a strong attraction to women wearing nylons. I wanted to touch their legs, and, eventually, to wear them myself. It's so much a part of my sexuality that I wear panties and pantyhose virtually all the time these days. (unless I'm nekkid!) For me it's both about sexuality and expressing my feminine side.

    Aside from all of that, I've lived the life of a typical man, worked in a traditional man's occupation, with a strong mechanical aptitude and athletic ability. I'm a fairly ordinary husband, dad, uncle, grandfather. And now, at this late stage of my life - a bisexual with a fondness for sucking cock.

    Just your average guy next door...
    you have a sexy body and a grt cock, how big is it. im 7x5 cut, i'm 5'6 140 lbs, always wanted 2 dress but married to a vry straight woman

  10. #10

    Re: How old were you when you started cross dressing

    hai i like u any type sex cal +917806991444

  11. #11

    Re: How old were you when you started cross dressing

    hi I was 12 started with mums panties only child just me and her

  12. #12

    Re: How old were you when you started cross dressing

    I was around 12 or 13 Mom's slip and hose. Been at it happily ever after.

  13. #13

    Re: How old were you when you started cross dressing

    I was in my late teens when I tried on my sisters bathers but it wasn't until after I turned after I turned 40 that I got more into in. I am perfectly happy being a man but enjoy dressing like a women occasionally. I like wearing bikinis, bra's, panties, lingerie and dresses. I find it both a turn on and also quite relaxing.

  14. #14

    Re: How old were you when you started cross dressing

    I did a bit of dabbling, when I was young, especially with sexy girl's panties, lingerie, and bikinis. I guess I was 12 when I first went all in and dressed like a girl make-up, undies, clothes, wig, shoes, and accessories. I'm not much of a crossdresser now but I did have an "Uncle" who loved to see me dressed up as a sexy gurl. It really, really turned him on so I dressed up for him. That was back when I was a smooth passable twink. Just dabble every now and then since.

  15. #15

    Re: How old were you when you started cross dressing

    Well yeah, that was pretty much it - when I was young I was very passable, I would confuse the telemarketers on the phone and a few folks in public and they would be so apologetic (and I would secretly be like, "Yes!") ..but once puberty hit it was just easier to live with the factory installed equipment. I became a lot happier as myself once I met some nice male role models.

  16. #16

    Re: How old were you when you started cross dressing

    Quote Originally Posted by elian View Post
    Well yeah, that was pretty much it - when I was young I was very passable, I would confuse the telemarketers on the phone and a few folks in public and they would be so apologetic (and I would secretly be like, "Yes!") ..but once puberty hit it was just easier to live with the factory installed equipment. I became a lot happier as myself once I met some nice male role models.
    Are you going to get a sex change, get fake tits, and chop off your balls and cock or keep them and be a shemale?

  17. #17

    Re: How old were you when you started cross dressing

    Quote Originally Posted by pole_smoker View Post
    Are you going to get a sex change, get fake tits, and chop off your balls and cock or keep them and be a shemale?
    I can attest, elian is quite masculine enough. Not defending him only interjecting a
    thought. He's competent enough to defend himself. That he doesn't speaks volumes.

    (M-x-Cargo-Bay-Dave)

  18. #18

    Re: How old were you when you started cross dressing

    I've thought about it, but it's just not worth all the hassle, I'd rather just be happy being who I am. Besides what some folks say is that the biggest struggle is the one for self-acceptance of what is on the inside.
    Last edited by elian; Feb 13, 2016 at 12:33 PM.

  19. #19

    Re: How old were you when you started cross dressing

    hi there would love to chat bout it with you I was 12 too when did you have first time with a guy

  20. #20

    Re: How old were you when you started cross dressing

    Quote Originally Posted by elian View Post
    I've thought about it, but it's just not worth all the hassle, I'd rather just be happy being who I am. Besides what some folks say is that the biggest struggle is the one for self-acceptance of what is on the inside.
    Exactly. Being secure in who you are is really all that matters.

    Not really one into, or appreciative of cross dressing myself, yet can
    appreciate those who are and do. I am more into simple country boy.

    Did wear a dress once complete with fishnets. I had lost a bet. Got told
    I looked good enough in the dress. It fit well enough but did not resonate
    with me. We're all free to like what we like, or not. Why it's called life
    and diversity.

  21. #21

    Re: How old were you when you started cross dressing

    When I was 16 I started going to parties and clubs in and around Los Angeles West side. I often dressed, with two girl friends helping and I looked pretty damn hot. I was thin, had great legs from skating and very long hair. I loved getting hit on, wearing super short skirts and thigh-highs. I'll look for some old photos.

  22. #22

    Re: How old were you when you started cross dressing

    Quote Originally Posted by elian View Post
    Well yeah, that was pretty much it - when I was young I was very passable, I would confuse the telemarketers on the phone and a few folks in public and they would be so apologetic (and I would secretly be like, "Yes!") ..but once puberty hit it was just easier to live with the factory installed equipment. I became a lot happier as myself once I met some nice male role models.
    LOL yes I was extremely passable as a younger teen, I was also a late developer and rather late and slow to puberty so I had a many years of cross dressing and passing as a teen girl before I grew too big or hairy to be passable anymore. It was a lot of fun confusing folks and having college age boys and older men hitting on me. Like I said one of my "uncles" loved to see me dressed so at first he was the main driver and instigator. Another of my uncles bet him that he couldn't get me to pass at a fashion show, well I got entered into the fashion show and no one knew I was a boy, uncle got a lot of compliments on what a beautiful niece he had and needless to say he won the bet. He got a kick out of it and entered me into more. after a while it got fun for me so I started dressing and going out with a girlfriend. We'd go to dance clubs and pick up men and college boys.

  23. #23

    Re: How old were you when you started cross dressing

    Started about 11 or so. Don't do it now, but I sure enjoyed dressing as a girl back in the day. Often wish I'd been one, but I'm not.
    .

  24. #24

    Re: How old were you when you started cross dressing

    Yeah, well I think that was the big turn on for me was watching guys getting just as excited for me the same as they would for a woman - no offense to the ladies but I used to get jealous of how easily they could attract men (duh)..

  25. #25

    Re: How old were you when you started cross dressing

    Quote Originally Posted by elian View Post
    Yeah, well I think that was the big turn on for me was watching guys getting just as excited for me the same as they would for a woman - no offense to the ladies but I used to get jealous of how easily they could attract men (duh)..
    Oh that's it! When I was made up to the 9's it was easy to attract men. Had to beat them off with a stick. That was to me the major appeal to the whole thing. I loved turning the men on and getting them excited over me. Then it was fun to pick the winners

  26. #26

    Re: How old were you when you started cross dressing

    I was about 12... "Borrowed" a pair of panties from a friends sister pink and silky. Never looked back.

  27. #27

    Re: How old were you when you started cross dressing

    A better question is when did I stop. I started at age 9 and stopped intermittently whenever I had a steady girlfriend. Finally, four or five years ago I stopped nearly completely. Nearly completely because I still wear women's "hi-cut" cotton panties every day. They are a whole lot more comfortable than nylon panties or men's jockies. For those of you who want to do the same, the best brand is Best-Fitting Panty.
    Last edited by DonLee; Apr 20, 2016 at 2:07 PM.

  28. #28

    Re: How old were you when you started cross dressing

    I was around 8-10. I would put on my mom's skirts and heels at night and get turned on with how feminine I looked. I would also wear my big t-shirt and with just my underwear and look at myself with my legs crossed. I should have probably been a pre-op transexual. I don't crossdress now because I'm definitely not passable enough to pass as one or a dragqueen.
    I would definitely crossdress if I was passable enough, wear my miniskirt and heels to the adult theater, score every cock in there.

    I'm such a sexed up mess

  29. #29

    Re: How old were you when you started cross dressing

    I was 4 - 5; had a twin brother and older sister and she would dress us up as her living dolls and parade us up and down the street; we had to act like little girls instead of little boys, she'd put makeup and lipstick on us and 'adjust' our cocks in our panties so they'd stick straight up. Was a closet crossdresser ever since, my brother and I would get together every chance we would get to dress and play.

  30. #30

    Re: How old were you when you started cross dressing

    Is wearing only panties considered as crossdressing? LOL. I had oral sex with numerous men in mfmf 4somes and in mfm 3omes while swinging with my ex-hotwife. I was 45 when she and I split up and I was very keen on exploring my bi desires/cocklust 1 on 1 with men. As it happened 2 of the first 5 men I met for sex were married men who were into wearing panties. The first of them surprised me when he stripped down to reveal a pair of very sexy looking low cut french style laced panties. I was instantly aroused ! He had not known how I would react but was very visibly turned on when I told him how sexy he looked. We made out passionately and enjoyed some of the hottest oral sex I had ever had. The other of the two married men asked me first if it was OK to wear a pair of his wife's panties, explaining that it enhanced his excitement. I said "By all means! Please do !" We met again a few weeks later and he surprised me by donning sexy stockings & garters and spiked high heels to add his panty look.....man oh man did it ever supercharge the sexual excitement for both of us !

    I had never harbored any desire to wear women's things prior to that. But after I had been with those 2 men I was very curious as to what it was that turned them on so very much. I decided to try it myself. Sorry to you Vicky's Secret snobs (jk), but I found what I wanted at, yes, WalMart LOL. A 4-pack of pink, white, pale yellow and black low cut french style panties (nylon with no lace). I also bought a very slutty looking pair of black fishnet stockings to go with the black panties. I stripped naked when I got home, donned the black panties and fishnets and sat down to my computer to look for men online. I was so aroused and horny just wearing them all alone. The smooth, silky feel made me feel so sexy and I realized why my panty-wearing friends had gotten off on it so much ! It never became a fetish with me and I never had the desire to wear them except when I was all horned up and lusting after men online. It's been 17 years since I first explored panty-wearing and I have only ever worn them for or with other men 3 times and they worked their mutual erotic charm for me and my partner each time. There are many men who think it unmasculine and sissy to wear panties or be with a panty-wearing man, but it doesn't threaten my own masculinity at all. In fact it makes me feel more masculine to have the balls to do it. Nowdays I have to be in a special mood to wear panties but I don't think I've ever gone more than 2 months without slipping on a pair as I look for partners online and lounge around my apartment feeling horned up and sexy. I am a tall, beefy guy and would come nowhere close to looking passable as a CD. I would look ridiculous to myself, not to mention grossing out partners/lovers LOL if i ever donned wig, bra, makeup, stockings & garters and heels etc, so I never felt a desire to branch out and go full CD. If I knew I could be passable to myself dressed as a woman I would definitely go for it. Still I have been with a few more partially dressed CD's over the years, passable or not, and it has never failed to arouse and excite me and mutually enhance the experience. I've yet to be with a fully dressed CD, but it's one of my few unfulfilled fantasies !

 

 

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