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Jessica =]
06-08-2011, 12:24 AM
hi everyone, im pretty new here, i think this is my first post, im not much of a talker but i LOVE reading through what everyone has to say there are so many interesting stories and awesome advice!

basically a bit of bacjground about me..im a 19 year old male (20 in a few days) but ever since i was a young age i always loved dressing up in real tight fitting clothing. i guess this all started from when i was younger i did gymnastics and we had to wear the really tight leotards. i just lived the feel of the silky smooth lycra all over my body. i used to love wearing it even when i wasnt doing gym, just wearing it under my clothes.

things got a bit restriced tho i couldnt really wear it during summer so i had to cut down and wear smaller things that still felt really nice and gave me a bit of a thril. this is when i found my mums lycra g-string. i always used to steal that and wear it as much as i could until one day my mother figured out what i was doing and hid it so i couldnt wear it again.

as i grew older i always had a bit of a thing for womens linngerie. mainly the underwear tho. i absolutly loved wearing thongs and g-strings but NEVER told anyone about this. i had 'borrowed' a few of my girlfriends underwear that they had left behind when they would come and stay at mine and i would normaly ear those whenevr i could and just tell my gf's that they didnt leave anything behind so i could keep wearing them.

when i moved out of home at the start of last year thats when i fully had some privacy to do whatever i wanted. this was when it got to the next level.
i started ordering things (underwear etc) online because i could and my girlfriend at the time was living in another city and would only be able to visit on the weekends, so she would leave a bag of her clothes at mine. she was also really into kinky costumes like the school girl outfit etc. this was when i started exploring more into dressing up. at first i would just sit in my room and do my study in underwear but then i found a few mini skirts that i thought id try on for a laugh and found i really liked the look of them on me when i checked myself in the mirror. i experimented with more and more of her clothes and she never found out for over a year and a half. i started having dreams of me fully dressed in heals and everything and going out to have a night in town. but i never had the courage to do anything like that, i never had the courage to even talk about this let alone letting someone see me dressed up.

so as time went on i developed more and more of a need to dress up and wearing underwear under my mens clothes wasnt enough.i put together a shopping list of what i wanted but i couldnt really go out and get it because i didnt want to go into a womens clothes store and start trying on clothes (im quite a well defined and muscly guy so its very hard to find anything that fits around my shoulders and also i dont look feminine in the slightest so it would be a little awkward if i went shopping for womens clothes by myself, i was always worried that someone might get the wrong idea about me). so this became a big problem because i wanted my own clothes and i also wanted to be able to pass for a woman in public and go for a walk about fully dressed up and to hear the clicking of my heels on the pavement but could never get any of it.
this was when i started looking online for ways to become a crossdresser without coming across to people as someone who has problems. and i came across this site and it has probably been the biggest help to me. it has given me advice on lots of things but mainly to have confidence in my gf and that i can actually talk to her about this, so i decided to give it a go but very gently.

so one time when me and my gf were out drinking i started bringing up the idea of her dressing me up in her clothes and what would she think. also i mentioned the idea that it would be real funny if we dressed up as each other and tried to get into town. it would be funny because everyone would know that we were joking and thats not normally what we do. (except for me it would be my dream come true and i would be out in public dressed up and loving it and noone would have a problem with it). she liked this idea so that was a good sign for me. we talked about how we would do this and what clothes we would wear etc for probably a month or two. then we went shopping and bought me a lovely short dress and a top that would cover my back and shoulders perfectly and some nice tights/leggings (i dont really know what anythings called, im VERY new to this but absolutly love it) and some HUGE heels. i made a bit of a mistake on that part. i just went looking for the sexiest heels i could find and i did. however i didnt consider how hard it was going to be to try and walk in them. i think the heel is probably 5 or 6 inches and woa is it tough to try and walk in them! i looked like a right fool when i put them on and tried to walk around my room. my gf was laughing at me the whole time but i was enjoying the fact that i could do these thigns and she still like me.

that was when i told her that i had actually been dressing up in her clothes for a long time and told her everything about what i had been doing. she was in quite a bit of shock but didnt seem to mind. she just asked straight away if she could dress me up. i was a little embaresed at first because i had never let ANYONE see me dressed up and here she was wanting to put me in fishnets, a tiny pink miniskirt, the gigantic heels and her bra with some stuffing in it and a really tight fitting top. my heart was racing with excitement at how much i wanted to put it all on but i was also extremly nervous. but i did it and loved it so much! she even said that i looked very sexy so that was nice. i stayed dressed up for a little bit but im now back at my parents house having finshed my course and i cant really walk around the house like that with my mum, dad and little sister, i would definatly be kicked out or at the very least laughed at and told to go put some normal clothes on. so i had to take off a few thigns but kept all the underwear on under my guy clothes. it was a thrill knowing that my gf knew i was wearing them and didnt mind.
we did have a talk about it a bit later on tho because we had a spa later on after my parents had gone to bed and i wore one of her bikinis, and she had a worried look on her face. so we had a talk and she is worried to losing me to a GUY. yea she thinks becuase im dressing like this i want to be a girl and therefore have sex with guys or be gay atleast. i tried convinving her many times that that definatly wasnt the case i just enjoy the feeling of dresssing up and there is a bit of a thrill doing something im not supposed to. however i have thought about it..but i definatly wouldnt consider myself gay in the slightest. more bi-curious. however the really strange thing that got me confused is that she said she would love to watch me having sex with another guy, as in me being the girl. so she doesnt want me to be gay but she wants to see me get f**ked by another guy...?

:straightface: so yea...if anyone could give me some advice on what to say and do in this situation that would be good lol because honestly i have no idea.
but i was very very proud of my gf for having to hear all of what i had to say and accept all of it and then take me shopping and dress me up. i absolutely loved it and it was the biggest thril of my life so far. however i am still in need of a wig which is proving to be really really hard, i cant really go out without one. also ill attach a photo of what i look like in man form and if anyone has any ideas on what sort of clothes or styles or even wigs that would really help me. as i said before im knew to this thing and have no idea what im doing but i just want to have some fun :D

just in the photos im the one on the left in the picture that has two of us. so yea u can see how tough its going to be for me to look fem in the slightest! however i do have the bonus of having some pecs so atleast ill be able to make some fake clevage there :) although finding a bra that fits around me is very tough

xd-tigger
06-08-2011, 06:43 AM
Wow that was a long thread. The first thing I will say is congratulations on coming out to your girlfriend and for having an understanding girlfriend.

As for the sex with a man whilst she is watching is an interesting twist on the situation.
My advice would be only do if you feel completely comfortable doing it. You really need to have a long chat to her about it.

Hope this helps and good luck.

Jessica =]
06-08-2011, 06:45 AM
haha yea i know ae for not being much of a talker i sure let it all out. i guess since its been build up for a few years i had to talk about it one way or another. thanks yea it was an awesome feeling! and now we are soo much closer as she now brings me back sexy clothes to wear. yea i dont think ill be doing that one any time soon, im not really comfortable with that.

Danni Renee
06-08-2011, 07:22 AM
I am happy to hear you have such an accepting girlfriend! Mine is very accepting too and it really helps. Like yours, my girlfriend does have worries about my sexual orientation and being completely honest with her has helped. I think she will always have those concerns but trust is built over time. My girlfriend does not have the same wishes as yours though so I am not sure how to advise you other than don't do anything you are not comfortable with.

As far as wig, I suggest a strawberry blonde. I also recommend something with bangs because the bangs can hide a masculine forehead. You can get inexpensive wigs off Ebay to try until you find the style you like. I am not sure if you still have the mustache or not but it could be a dead giveaway if you are trying to pass!;) However, there are others on the site here they keep their mustaches so to each her own!

For clothes - wear what you want. I prefer to wear half or 3/4 sleeves to hide my arms but other than that I think you could get away wearing anything you wanted.

Good Luck!

Jessica =]
06-08-2011, 07:54 AM
yes its very nice to actually be accepted by someone u really like so that made me happier. yea its a weird one isnt it, but theres no way im going to do something im not comfortable about so thats a no.
ok yea i was thinking that or medium brown, definately long hair to cover shoulders and boobs (or lack thereof) but yea havin bangs is a good idea. haha oh dam u mean i have to get rid of it?:) na i got rid of that a long time ago. yea i have two outfits at the moment and am trying to take some pictures and put them up on this site now so maybe half an hour? but yea my gf thought the same thing, 3/4 sleeves to cover the biceps. ill post a link to my pics when theyre up.
thanks for ur advise! :)

p.s heres the link with all of my two outfits lol
http://www.crossdressers.com/forums/showthread.php?154828-first-time-in-something-more-than-lingerie&p=2513713&posted=1#post2513713

hema
06-08-2011, 08:42 AM
wow... we do have some resemblance ... the start , the dress up , the body frame as well as letting our secret to our gf....
i m amazed , but he fortunate part in my side, is tat my gf has completely accepted and indeed enjoys and gets excited more than wat i actually feel about cding...
in fact, she was first curious about my orientations , but later managed and convinced her .... now she feels very comfortable over whatever i do, and in fact she helps me wit cding
initially , every gf feels awkward or surprised or annoyed , but convincin and bringin her into u and ur desires rests in ur trust, hopes and talents :)
don compel her too much , u can go in for occassional cding with ur gf,,, atleast u r lucky enough to ve a gf who has helped u in shoppin within a month of ur exposure or ur secret...
it took almost 4 months fr me to ask my gf to go shoppin for me ..... keep ur thoughts simple, don pester wit dress ups and feminine make over every time u meet...
be cool and let her cool...
once she s into the rhythm,, i bet u ll live ur dreams....
hey pilot, those magenta top are pretty and i wonder y u haven take a complete picture of u in tat dress...
are u tryin to hide ur identity ??? cuz ur boy mode pic is well above in this thread and the link rests here too :D lol ...
all the very best...
do share ur exp with us... enjoy

MsKimiko
06-08-2011, 08:52 AM
Wow that is great your Gf was so accepting and open to the idea of you dressing. You brought it up really subtly and it worked. I came out to my Gf and she took the absolute opposite reaction to it. Now I have to feel like I'm lying to her because I am hiding that from her :(

nvlady
06-08-2011, 04:52 PM
Back to the sex with a guy part.
If you're not attracted to guys you could tell her that there are "appliances" she could wear so that she could assume the male role.

PetiteDuality
06-08-2011, 05:00 PM
however the really strange thing that got me confused is that she said she would love to watch me having sex with another guy, as in me being the girl. so she doesnt want me to be gay but she wants to see me get f**ked by another guy...?

Man, she's testing you. If you were gay, you would have said "ok" immediately :-)

Jessica =]
06-08-2011, 05:35 PM
oh the resno for not having complete pics is i dont have a wig, but when i do ill def be putting pics up! woa that is cool how we have a lot in common.
yea i think my gf will warm up to the idea i mean last night we had a skype phone call and she wanted me to 'reverse strip' so that was fun lol.

Jessica =]
06-08-2011, 05:38 PM
yea i know ae i was soo relieved. i was planning on doing it all day and i finally managed to get the courage up just before we went to bed. so it wasnt easy but it was a great feeling to know she accepted it.
oh that sucks..yea i had to lie to her when she didnt know about how things mysteriously ended up in the wash or not where she left them haha.

and to reply to the other comments yea i know there are 'appliences' out there and im sure she does lol but i really dont want her to get one haha im not into that at all. i just said no not yet that not my thing and she said ok. but yea maybe you are right and she is testing me...good thinking :)

hema
06-09-2011, 01:56 AM
whew..... whatever ... ur gf is on ur side.... enjoy ur best and lookin forward for complete pics... :D

Jill Devine
06-10-2011, 07:17 AM
Man, she's testing you. If you were gay, you would have said "ok" immediately :-)

100% agree. It's a test. She is looking to see how you respond because most women assume that if you cd then you could be gay. She is testing her assumption.

Jessica =]
06-10-2011, 10:35 AM
sweet ok then so rather than go to try and please her 'fantasies' just tell her the truth and admit im not into that? that way she will undersatdn that im only cd'ing because i love it and not that i want to become a woman and all that comes with being a woman?

Jill Devine
06-10-2011, 05:14 PM
Correct. Never do something as drastic as that unless you are really onside. Speak up and tell her how you feel.

Cynthia Anne
06-11-2011, 06:21 AM
I agree this could be a test! It would be risky to follow through with her idea! Besides it would be cheating on her! I would drop it there! If she insist, then I would go with Nvlady's sugestion!