Your First Time Dressing For Your SO?

[HayleyGG]

Hey ladies!! Hayley again. So Calvin and I think we're ready to explore his dressing together later today. Since this is my first experience with this, and his first experience with a girlfriend finding out the way I did, I was hoping you girls could give me some advice as to what the heck we should do..haha.

We originally thought that perhaps we should get a few drinks in us and start slow with him maybe just throwing on some fishnets. Then we got some great advice from a good friend here who said that I probably shouldn't see "my boyfriend in fishnets," but that I should see the whole package of Callie to disassociate Callie from my boyfriend. We feel that was great advice, because now that I think about it, it would probably be more weird seeing my boyfriend hanging out with me in a tshirt, boxers, and fishnets. Right? So I think we should start off with the full deal.

But what I'm wondering, is what we should do after he dresses so it isn't completely awkward for either of us? Do we just watch tv like normal ignoring the fact that anything is different, do we just lay in bed talking, do we play Rummy? Haha. I don't know. I don't mind being out of my comfort zone, but I do want him to be comfortable and not embarrassed.

So to help you understand a little more about him/us to help formulate your amazing advice, I thought I'd tell you a few things. He has told me that he doesn't feel like a separate person when he dresses, he just feels like him...in women's clothing. He doesn't feel the need to be called "she," "her," or by his femme name. So it seems like Callie is not another entity, and I appreciate that. His femme side doesn't have another personality, and there's no other person that I need to get to know. It seems like his dressing is very basic. Just simply dressing, with no other attachments.

So with that said, since "getting to know Callie" is out, what do you think we should do to minimize awkwardness when we're hanging out today? Thanks a lot!!

-Hayley

PS-Just an edit/update: He's never actually left his home dressed, so going out together is likely not an option. So, I guess we're looking for indoor things.

[Shari]

He should be fully dressed. I'm sure that's what he wants anyway and probably you do too.
Why not spice it up by you getting sexy too? Put on your slinkiest, sexiest outfit then just allow nature to take its course and I think you'll both quickly reach a "comfort" level.
Just let go and enjoy!

[Katie Moore]

Without knowing either one of you, I'd say do girl/women things together. Like SHOPPING, lunch, movies, pedicure etc. but only if you are both comfortable going out. If going out is an issue than maybe an at home makeover, special lunch or dinner. Really do just about whatever you would do with your girlfriends. Just have some fun. Glad to see you are willing to try this with your guy. Keep us posted.

[Kittyagain]

. . .

So to help you understand a little more about him/us to help formulate your He has told me that he doesn't feel like a separate person when he dresses, he just feels like him...in women's clothing. He doesn't feel the need to be called "she," "her," or by his femme name. So it seems like Callie is not another entity, and I appreciate that. His femme side doesn't have another personality, and there's no other person that I need to get to know. It seems like his dressing is very basic. Just simply dressing, with no other attachments.

So with that said, since "getting to know Callie" is out, what do you think we should do to minimize awkwardness when we're hanging out today? Thanks a lot!!

-Hayley

In the above quote, you answered your own question. He has not changed, he has only changed clothes so do what ever you would normally do.

My guess is though as Shari posted, be ready for a high level of passion.

Now one more piece of advice. Sometimes new dressers have a squid vision of what is proper. Bad color choices, overly bold makeup, that kind of thing. Don't laugh. Smile, hold her hand, then say lets go try a little different look. Then you have bonded.

Hope this helps.

Kitty

[linda allen]

I suggest that you dress him. Well, help. Hand him the clothes and help him if he needs help like hooking the bra, adjusting the wig, etc. And help him (now "her") with her makeup. Be part of the transformation.

Once you're done with the makeover, do whatever is comfortable for both of you. Go for a drive (you should drive), walk in the park, a movie, go to the mall, a nightclub, whatever you are both dressed appropriately for.

[tinalynn]

Do whatever you would normally do. Wait until you're both comfortable with everything before going out, having sex, whatever - there will be some awkwardness, especially the first time. I think he's similar to me - we both like dressing, but don't really have a second personality with it. When I dress at home, wifey and I just do what we normally would. Be normal about it because it doesn't have to be anything special. Don't plan on doing anything 'special', but if you both feel like doing something then do it. Just don't have any pre-concieved notions about what you're going to do. Like fantasies that come real, reality is often different than the outcome you plan on. So just let him dress, watch him if you wish, and go with the flow... If something happens, it'll happen. If not, so what? The big thing is that you are comfortable with the way he looks, whether it comes to anything, or not. He'll be happy just being able to dress knowing you're okay with it.

[suchacutie]

Since for us Tina IS a separate individual that we are both (my spouse and myself) trying to understand, any parallel ideas I might have are, well, mechanical.

We usually plan Tina's outings so there is some structure. We don't stick to it obsessively, but at least we start with a framework. The two of you could simply ask each other, "so what shall we do tomorrow evening?". As the evening progresses, you can be inventive if the mood strikes you both!

Now, this one is personal and is something the two of you should decide beforehand: Is Callie comfortable being seen in transition? If yes, then I agree that being a part of the transformation could be terrific fun! If not, let Callie transform completely and then join you in the first planned activity (dinner, making dinner, or whatever).

Lastly, there has to be a moment of transforming back. Likely Callie will want a shower or whatever (makeup and nail polish has to be removed, etc) and again this might be private or not as you decide, but I suggest you decide this beforehand as well.

You've already come a long way knowing if she is a separate person or not, what name to use and when, etc., so I expect the rest of the details will be pretty easy!

Beyond this first time, expect change. You are on the ground floor of an exploration of a special and previously protected part of his being. As you both become more comfortable, the thoughts of today might not be the thoughts of tomorrow

Have such fun!

tina

[Sophie86]

I recommend dinner, drinks, a movie, and some chit chat. Make him talk. Don't let him go into his belly button, and get all self-conscious.

Good date movie recommendation: Zerophilia. (You can watch it online via Amazon.)

And please, please, don't give him the same "compliment" my wife gave me the first time she saw me completely dressed. She said: "You don't look as bad as I thought you would."

[Tina B.]

An evening at home, let him go off and dress, then join you for drinks, dinner, and a movie. The first time, don't get involved in doing a lot, just work on being, as in being together, and getting used to the new look of your boyfriend. after that, what ever the two of you can enjoy together, do that.
Tina B.

[HayleyGG]

And please, please, don't give him the same "compliment" my wife gave me the first time she saw me completely dressed. She said: "You don't look as bad as I thought you would."

Oh my, that's terrible. You made me laugh, though. I will definitely keep that in mind. He is pretty hot in his main picture on here, so I already know he doesn't look that bad. Thanks for the advice.

[xristy]

I think he should get dressed up from head to toe. That way you can see everything and not just a half dressed person. As for what to do, I think you should just talk first and see where that goes. You never know how each other will feel when dressed and together. It may be awkward, it may not be. I wish the the best and hope to have this experience with my SO some day.

Xristy

[SamanthaS]

Watching television sounds good. Whatever you two do together is a good start.

[Alberta_Pat]

It all really depends on what you both want to do.

From your introduction, it seems that Callie "dressed" for sex. If that is your objective, then dressing for a "quiet" evening seems right.

Both of you could dress to enhance that aspect.

Fully dressed in attractive outfits with the unwrapping of your "presents" to each other would be my suggestion.

Let this first time be a discovery of each other. Explore, discuss and just revel in the others presence.

Take some pictures to be discussed at a later time. Share, bond and enjoy.

[Sophie86]

He is pretty hot in his main picture on here

Ah. Yes. Yes, he is. Hope you guys have a great time.

[kendra_gurl]

I cannot agree more with the others who say let him transform alone by himself unless he ask for your help. His first time to show you will be a very nervous yet exciting time for him.
No matter what your first impression is laughter will destroy him. Most of us in the begining started dressing for the mirror in more of a fetish way and in doing so we learned to ignore the parts of our reflection we did not like focusing only on the parts we do like.

I'll never forget years ago the first time I dressed for my wife I had just gotten a new latex breast device. It was before silicone forms and was an all one piece thing and really huge. I knew it was way too big but tried it on anyway after spending lots of time with makeup and hair and clothing selection. My wife could only see these huge breast and started laughing so hard she hard tears in her eyes. Looking back I see it was all my fault for putting this thing on in the first place but my heart was broken and it took months for me to attempt showing her Kendra again.

A good movie on DVD is always good to allow for some time to adjust and settle in on the whole experience before you start with much communication about if he would like your help to tweek his look or make suggestions.

While we all hope the evening goes well for you both and that you are careful about how you handle seeing him for the first time I would also say you should remain as honest as you can too. Sincere but honest. If there is something you really don't like or can't handle just find a nice way to let him know.

One more thing... Don't be suprized if everything you think you know, or what he has told you about his being the same while en-femme or in drab turns out to be totally the opposite of reality.

Crossdressers do not get all dressed up and stand infront of the mirror to show off our muscles or pose like the Incredible Hulk. We primp and practice our feminine mannerisms and check out our legs and butt just like you GG's do

Good luck always know you are a very special and amazing person too

[CallieH]

.. He is pretty hot in his main picture on here, so I already know he doesn't look that bad.

Thank you honey.. you will not be disappointed!

[xristy]

After seeing your profile pic, I don't think she will be disappointed....

Xristy

[dominique]

I would let him do every thing himself. The reason he wants to prove that he can dress for himself and not for any body else. Then have 'fun' if you want. But don't criticise him.

[Jane P]

As this is something I have never done , I don't know for sure . Sorry. I know one thing, I would be scared s@#Tless , but that's just me. I think if it were me I would like to sit at home and talk , about anything. Probably anything other than the fact I were sitting in front of my wife (or anyone else for that matter) trying to look pretty and feminine and wondering what the hell she must think of me . Maybe watching a bit of television or a movie that you could still talk through. Maybe some hugs of reassurance to show that she loved me . I guess try to have fun and try to have as normal an evening as you would otherwise. Good luck to both of you.

[CallieH]

Thank you everyone for all the tips and advice. We definitely have a better idea now about how to approach this. I want to make sure I don't make Hayley uncomfortable, she's a wonderful and supportive girlfriend and this is a truly amazing thing she is doing for me.

As this is something I have never done , I don't know for sure . Sorry. I know one thing, I would be scared s@#Tless , but that's just me. I think if it were me I would like to sit at home and talk , about anything. Probably anything other than the fact I were sitting in front of my wife (or anyone else for that matter) trying to look pretty and feminine and wondering what the hell she must think of me . Maybe watching a bit of television or a movie that you could still talk through. Maybe some hugs of reassurance to show that she loved me . I guess try to have fun and try to have as normal an evening as you would otherwise. Good luck to both of you.

I hear you, I'm nervous and scared, yet happy and excited too!

[AmandaJ]

The first time I ever dressed entirely for my girlfriend, we played strip poker and just hung out listening to music.

[t-girlxsophie]

My first time showing Sophie to my then gf was as nerve wracking experience as I ever went through,we had waited a few weeks after meeting (we chatted online 4 months) we both talked over how to approach this,and we agreed the best way was for me to disappear to my room and get dressed as I normally would,gradual introduction really wasnt an option either of us were comfortable with.

Well getting myself dressed wasnt like any other time,The nerves were unbelievable as I dressed,and as for makeup I had visions of lippy smeared over the face,poking my eye out with mascara etc I decided to dress pretty sexy but not overtly so Pink Vneck Sweater,denim miniskirt,tights and low heels,even tho she saw pics and we chatted I was aware she may have had second thoughts,But as I was wearing my big girl pants I just took deep breath and went for it.The result being she was brilliant with me,we hugged (it seemed for ages) and she said I looked great,we talked and talked and shared a bottle of wine,It wasnt awkward in the least.I really hope you both have the most memorable "First Date" possible

Sophie

[lynnd]

When my BF started dressing in front of me we would make it a movie night at home and rent chick flicks. He started out just partially dressing in womens things, he didn't even own the make-up, wig, and forms that he does now. Now he is fully dressed and I get to be the photographer. And now we go out to the movies.

[Shelly67]

Praps this will ease the situation . Set a time and date ........ have a fun night .... go slowly .

[Stephanie47]

If I were dressing for my wife (never going to happen) I'd present myself fully en femme with wig and makeup. I wouldn't dress one article of clothing after another. That smacks of losing a boyfriend slowly, while full presentation seems like the arrival of a new girl friend.