First time with GF suggestions? Anyone? GGs?

[StephanieCD]

Wow. So, as some of you may remember I told my GF and we had some weirdness about things... well, I found some of the weirdness was over some things going on with her in her own world - an issue but we are working through it.

Anyway - I'm writing because after sorting out the other stuff we just had a discussion about the CDing. So, she was way more supportive than I ever thought! She even told me "honey if the hair on your body disgusts you than ****ing shave it off!" and also told me that I have nothing to be ashamed of and, though she might be a bit uncomfortable at first, that she wants to accept all of me and that participating might even help her be less shy about sexual things...

I told her about all of you and how it's recommended among us to let the significant other kind of have control after "dropping the bomb" - she said that she's willing to try things and wants to take my advice to go one step at a time but doesn't know where to start. I'm pretty embarrassed letting this out at first so I suggested that I make a list of things that we could do to "ease into it" - and that I'd ask for all of your help :)

What things would you suggest she and I do the first few times to get comfortable with my dressing? I'm afraid to bring too much on at first - I'd definitely appreciate any input from the GGs on here... I don't want to expect her to accept me going full drag all in one night - and I don't have a "she" to introduce her to... I just like to dress - a lot of it is sexual, too. I want to put some really tame things on the list like read Glamour together to discuss what I like or watch Too Wong Fu but I also want to put some more forward stuff like buy panties or have a makeup night or something....? And I want to offer some fun aspect, too - she just wants a big list of stuff to look over to get a good idea of not only what I'm into but what we could do together - especially at first...

Any ideas? Come on, girls, I know you got some ideas! ;)

[Kaye_martin]

Steph: Take it slow at first, wear a skirt and top and have a nice evening watching a movie together at home. Get comfortable and then take it from there with a makeup evening and what have you. You should count yourself amongst the 'lucky ones' :)

Have fun, that's what it is all about :)

Kaye_Martin

[Koneko]

Well, when I first told my fiance, she was a little weirded out by it. ok, that's an understatement... but slowly she warmed up to it and even encourages me to buy nice girly things for myself instead of spoiling her so much.

It just takes time. I completely dropped the subject for a while and it was her that started warming up to the idea. I just occasionally kept wearing panties under my normal clothes now and then, and one day while we were shopping she grabbed a pair and said that I'd look good in them. Everyone is different, but give her some time to sort things out without pressuring her for a decision too early. I think that's good advice for any major breakthrough.

[Sandra H]

Hi Stephanie

I am only a GG in my dreams, but I did have a good relationship with my wife who knew about my dressing and helped me. I have also had no real problems with other girlfriends. In respect of my late wife, I will not say if what I am about to say was done with her or another girlfriend but it worked and we both enjoyed our dressing.

Many GG’s have a fantasy of making love with another woman, but like men having a fantasy of wondering what sex with another man would be like they never would try it when push comes to shove. So what we did was to start with my dressing by including dressing as part of our lovemaking. We did this by starting slowly. I shaved all my body hair off back, chest, arms and legs so they were smooth and fem like. Then we would get ready for some lovemaking. My GG would go to bed and I would get ready, I put on some make-up, wig, bra, panties and tights with a squirt of her perfume. To save embarrassment to both of us and to keep the fantasy I would enter the bedroom with the lights off and lie next to her. We kissed and caressed her and each other. What we were having was lesbian sex.

This way we both got a lot out of my dressing. As we both got used to the idea we could extend the amount of what we did. We did this by adding more cloths and allowing my GG to see me dressed. She helped me look more like a woman with my cloths and make-up; she also helped me buy a nice wig. Soon I looked great when I was fully dressed. By this time we spent the evening as Sandra and would have a meal and drink some wine as part of our night of passion. Sandra had by this time turned into my GG lesbian lover. As we went to bed she would start to kiss me and run her hand up my skirt and she took control undressing me as we kissed and caressed.

One rule we had from the start was I had to keep my manhood inside my panties as I performed oral sex on her as she ran her hands over my silky legs and bum. She had several orgasms as I kissed her and did what I needed to do to please her. After she had been pleasured I would go to the bathroom and take off all my Sandra things all my clothing and make-up. I was now back as her male lover. If I had been worked up during the lesbian lovemaking I would see to myself in the bathroom before going back to the bedroom as a man. When I got into bed she was still hot and ready for some real male to female lovemaking and WOW it was great. As part of her fantasy, she felt as if she was having an affair with a girl named Sandra and her male love was totally unaware of it.

This way we both got a lot out of my dressing. I was able to be Sandra as and when I wanted, we even went out shopping together. My GG enjoyed her fantasy without any guilty pangs, as she really knew that she did not have sex with a real girl. We both had the best of both worlds.

Sorry for going on so long, but it worked for us. As in most things in life when there is equilibrium everything work smoothly. The very best of luck and I hope I have been of a little help without boring you too much.

[Celeste GG]

I like Sandra's approach. You really need to let your girlfirend be in control, so she can handle it. Some GG's love having a T-girl girlfriend non-sexual... some are the total oppostite, they love the lesbian love thing like Sandra's.

If you start as just two girls together as friends, then it's hard to make it sexual later.

Start slowly, but as a step to how you mean to go on.

[JoannaDees]

I like Sandra's approach. .

Uhhhh .... yeah!

[StephanieCD]

Sandra's approach sounds very much like I did with my ex - I like it a lot! That's where it's heading - someday. I was thinking a tad slower for the first time... like Kaye's - just a skirt and a movie or something. Or maybe just hanging out with panties she bought me under my clothes or something... she thinks she might be able to like it sexually but I want to get there gently, ya know?

Maybe strip and then get dressed poker ;)

[DonnaT]

watch To Wong Fu

A good movie from our stand point, put the sexual inclinations of Chi-Chi Rodriguez in particular may throw her off a bit.

Where to start. Paint each others finger nails. Then offer to do her toe nails and see if she offers to do yours. I she offers to do your, ask if you should slip into a skirt first so she'll have better access and you won't worry about pants falling onto the painted nails.

Have a little wine and crackers on hand to set the mood.

[StephanieCD]

Where to start. Paint each others finger nails. Then offer to do her toe nails and see if she offers to do yours. I she offers to do your, ask if you should slip into a skirt first so she'll have better access and you won't worry about pants falling onto the painted nails.

That's clever enough to have been mine ;)

(sadly, I have embarassingly gross pinky toe nails lol)

[StephanieCD]

Now that I think of it... I know she liked The Birdcage.

[Wenda]

Lots of good advice. I told my gf when I bought some lingerie, and we talked about it a bit off and on. She was a bit cool. I think she thought she was loosing me as a male partner (and she has had some bad luck with partners). As she became more re-assured about the stability of our relationship, she became more comfortable with the concept. We took a long weekend, near her birthday, and I gave her a very nice leather corsette. I had a black thong, black thigh-high stockings, a soft bra, and a little pair of A breastforms. We went to a mall, and I picked up a nice pair of ankle-hieight boots, and then bought a sexy pair of vinyl knee high boots for her. After that, she took over, and helped me buy a number of things. We went for dinner with me wearing the lingerie, and came back to the hotel and played cards with me as Wenda, and her character, Jaya, began to evolve. We have developed a pattern that when Wenda is with my GF, Wenda is submissive, and Jaya is dominant. Wenda has become very adept at pedicures, foot massage and body massage. Just try to be patient, thoughtful, grateful and, above all, honest. You are off to a good start. Like every relationship, the enjoyment has to flow both ways, and with sensitivity, you will find a marvellous new way to enjoy new aspects of each other. Best wishes. Wenda.

[StephanieCD]

Did I understand you correctly in that your female partner developed a "personality" to counterpart with Wenda?

[Tamara Croft]

Hiya Steph

When ~Tammy~ told me about her desires to dress as a woman I was in total shock. She got this little black skirt out I presumed was for me :p Then she said... ' I like wearing it'!! *bombshell* I can't really remember exactly when I started getting involved with her dressing, but I remember I used to like doing her nails and makeup. Eventually Tamara (not my real name) was created and she got more involved. I guess it's like having another personality really, but its so much fun. My advice to you is let it evolve naturally and make your feelings, needs, desires to each other perfectly clear from the start. If you don't like something or your GG doesn't like something, discuss it!! To me it's all a little bit of give and take and a little trial and error.

Have a girlie night, do each others makeup and nails, choose each others clothes to wear and take pics for you both to have a giggle at.

Tamara x

[Paula A]

I agree with Donna, get out the wine and cheese and snacks and do her nails first, then ask her if you can do her toes. she needs to be first. el numero ono, in command. If she in decides to your nails then let her. let her initiate the action. she might not be ready to see you in a skirt just yet. let her feelings direct what happens. Go shopping, Buy things for your GF, you know where it will lead, " i like that color or that skirt or those panties - whatever. just remember let your GF initate the action and you will be progressing at a pace she dictates or desires and can handle.
from your post it soulds like she might be a bit reserved in the bedroom, or have a few issues, whatever they are in there. If that is the case then I would not reconmend introducing her to stephanie in the bedroom, and if she has issues with lesbian sex make sure that after a night together and the mood strikes you both that you revert back to drab as to not alienate her more. Nails are one thing, a corset with thigh highs and a mini skirt is completely another. Many a long journey has been successfully traveled using small steps.
Good luck and have fun.