I've been dating a guy

I never in a million years thought this would happen, but I've started dating...as a woman. A few weeks ago, I hooked up with another CD'er who was visiting Chicago and we spent some time together en femme. We really hit it off, although we have very little in common except our crossdressing. I asked him if he would ever want to go out sometime with him as the guy and me as the girl, and he said okay.

The next time he was in town, he asked me out on a date! I know this sounds ridiculous, but I was so nervous putting on my makeup and deciding what to wear. I really wanted to look pretty for him. He may be a "plain Jane" as a girl,but he is a very good-looking guy and a well-mannered gentleman. After he picked me up, it was one thrill after another as he opened doors for me and told the waitress that "the lady will have...." I took his arm as he walked me home, which felt wonderful, and when we kissed goodnight, it seemed so natural.

He's been back twice since then, and last week I cooked dinner for him. You should have seen me in my apron setting the table and lighting candles. It is all so innocent: we haven't gone beyond hugs and kisses - we are both straight - but I am starting to like this way too much....

Usually I'm the one giving advice, but I could sure use some now. Should I break this off before it goes too far? Or just enjoy it while it lasts and see what happens?

Windy

Hey Windy,

I'd give every thing I own, to be in your shoes, sounds like my dream come true, only you are the dreamer, grab the bull by the horns and get ready for a long pleasant ride, maybe even one of those "Lived Happily ever after" stories.

I wish all of the best, good luck to you.

Ricki B

Windy

There is nothing wrong with exploring this but do be careful about getting caught up in your fantasies. I believe that both gender and sexual orientation are fluid so it is quite natural for bi-curiousity to turn into bi-sexuality. Dont fall into the trap thinking you are doing someting morally wrong.

I would suggest that you actually sit down with him and have a forthright talk about this. After all he is a CD too so there is no need to hide anything. You need to ask each other where would this lead to? Could there be a realistic future for this relationship? Or is it just best to stay friends and take turns being the gentleman for each other?

Don't panic! Just continue to take your time and see how the friendship develops. Be honest about your feelings, that you're nervous about where this may lead as it's new territory for you. He obviously likes you, and will understand if you need time to explore your own feelings about this.

Chances are you may be experiencing guilt, shame, and confusion about this friendhsip as a 'straight' guy, so try to focus on what makes you happy. There's really nothing wrong with discovering this side of your sexuality. If he makes you happy, then it's right for you.

Remember: don't panic, take your time, be honest.

You'll know in your heart what is right for you.

Good luck,

Assuming both of you aren't involved with anyone else, why not? As Helena said gender and sexuality are more fluid than the either/or way society typically views.

As both Adele and Helena said, it's probably good for the two of you to talk about how you feel now, where you think it might lead and how you feel about where it might lead.

Windy hon, you are a big girl. I know that you are having the time of your life and you deserve to be treated as the lovely lady that you are. If spending time with this gentlemen makes you happy then continue to do so. Don't let your concerns about bi-sexualty get in the way of what could be a wonderful friendship. You can explore the relationship and enjoy all of the pleasures of being "his" girl just by being close friends. If things in the sexual department develop, let yourself enjoy the total experience and don't be hung up by labels and pre-concieved notions. Enjoy yourself and trust your instincts. You have a good head on your shoulders.

Love,
Theresa

It sounds like you're doing fine following your heart, Windy. Don't let your head get in the way. :)

Windy, I think you have received excellent advice here. You need to think about what you really want and what you are prepared to do given the situation. I also think talking it over with him is a necessity. You would do this before anything else happened if you were dating anyway. You need to know a whole lot about him and his background.....married, HIV status, interests, etc...

I agree with the other ladies.

One thing missing from your post, have these dates all been him as a guy and you as a girl?

If so, how does he feel about that? Does he feel his fem side is being oppressed?

Do you think you two could reverse roles if he needs to express his fem side?

Take it here it leads you. If you both want to go there, go. There is NEVER anything wrong, morally or otherwise about two people showing some love and affection for each other. And if some physical pleasure come from it even better. My first male experiene was with a childhood friend. Growing up he was the the kid picked last for sports, mama's boy yhr whole thing. Not quite a sissy, but not a "boy". We became friends mostly due to our moms being friends, he was a couple of years older, I guess I kinda looked up to him. I was in college aswas he but he was out of state. he came back to town cause his momwas sick and we spent a lot of time catching up. He didn't know about Brenda, and I didn't know it but he was Gay. We were talking and as it looked like his Mom wasn't going to make it. (she did), he came out to me, and asked if he should tell her. we talked about that and a lot of things when he admitted to having feelings for me. I kinda dodged it and said the usual "It's ok, i'm not like that, but I don't maind. I'll always be your friend etc." But for a couple fo days it stuck with me. I found myself thinking abot him while dressed, and haveing the most intense sexual response to it. Once his Mom was out of the woods I called him and told him that i had something to share with him, could I come over the next day and he agreed. I called up my friend form school, a girl who knew about Brenda and asked her to help me. she gave me a total makeover, bought a new outfit, jewelry makeup the whole deal. She drove me to his house and left. when he answered the door he was speechles, as was I. The rest of the night was simply magical, while I had relations with a women , it was the most intense and passionate experience in my lifeto that point, I guess because it was with someone I had genuine love for.
OOOPS. My big mouth again. Someone needs ro teach me to be quiet I guess. Sorry ,Girls. So yes...follow your heart. don't ignore your head, but every once in a while tell it shut to the F**k up!

Be Happy
B.

Windy I'd say go with your heart. leave your head out of it. It realy sounds like you are having a great time so just go with it.

Windy, I also feel you should follow your heart. Sometimes in life, situations and opportunities arrive and our minds over rule our hearts. Sadly then, those opportunities are lost forever. Life is too short.

I agree with the other girls, I think you both need to have an honest and sincere discussion about your relationship. That way, there would be less chance of either of you being hurt emotionally, if things don't work out.

Kim

Hello Windy :)I reckon be honest with yourself and be honest with him, but most of all just enjoy, it sounds like you are both having a great time ;)


love mand xxx:)

Hi Windy,

I would say just enjoy yourself and see where it goes. He sounds like a real gentleman and treats you well. Go for it.

BrendaChristine, I'll second that!

And to you Crissy, good luck and enjoy yourself

Hugs,

Tammi

WindyCissy:

Go for it!

kaye_martin

windy the answers your looking for are in your thoughts and in your heart... just keep in mind that someone else has a intrest and feelings in this too ..
explore and enjoy to whats comfy with you ....but do so be mind full of your
"dates" thoughts and feelings too....all too often we forget that we are not the only one ......that might get hurt .....

Hi Windy

Hey, I hope you have a great time. I figure you're an adult, and you have a good head on your shoulders, and you don't have to answer to no-one. Go for whatever makes you happy, that's what life's all about.

GypsyKaren

also take into consideration that he may want to be the girl sometimes.... it may not be what u think.... BUT talk to him about it.... if you are bi-sexual, in my opinion, it is not morally wrong.... you are who you are.... i am openly bi-sexual and proud of it.... i dont flaunt it around people, but they do know so i dont push it on them.... but talk to him.... if he wants to be ur boy toy, go for it! lol

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Originally Posted by windycissy

and when we kissed goodnight, it seemed so natural ... but I am starting to like this way too much....

Usually I'm the one giving advice, but I could sure use some now. Should I break this off before it goes too far? Or just enjoy it while it lasts and see what happens?

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I'm going to out on a limb here and speculate that if you liked it when he held you and kissed you, you may be ripe for more. To me, kissing a man is kind of a litmus test. If your reaction is "Ewww!", then you're probably not wired that way. But if your reaction is "Mmmm, that's nice", then ... well, you know.

A thornier problem for me would be switching roles. First scenario = "Mmmm". Switch = "Ewww". Not because of her being en femme, but because I wouldn't like the male role. Make it two fems and I'm back to "Mmmm". When I'm a guy, I am hetero.

At least I think I am ...

Windy...
What do you mean by go too far ? Why not ? If you are into kissing, holding each other and you both feel good about it, then why not. Don't "Break it off", girl, I have been there and done that, and have felt sorry about breaking it off ever since....

Windy,
Not that one would get a deep insight into who our other sisters are by this site and each others posts and responses, but from all my observations - you have been one of my mentors as a CDer. So effem, composed, knowlegeable,experienced. (not to add pressure to your situation). Allow me to add the fact there are a few recent posts raising the question about sex with a man as a CDer. When I read those posts, I couldnt answer that question immediately. (if asked now - I would revolt at the thought of having any relationship with a man as a CDer -I am not in a total woman mode) I always wanted to hold off on an answer to that question because I knew as full CDer - when I got into that grove as a woman - not a CDer - but as close to being as a woman as I could - thinking like a woman (am I a man in a womans clothes verses the real persona of being a woman, to both dress, looks, mannerisms, feelings, desires, and even - sexual desires), would there be that womanly desire to be total woman? Total. Not just be accepted by GG's (who I adore)but that desire of all GG's and that is to be suitored by men. Pleased by a man. The right man of course. Understanding. Caring. Romantic and makes me feel like a woman? Windy, just to think of you dressed as a woman, preparing dinner, apron, lighting candles, waiting for him to arrive - is my picture of being totally efem both mentally and (almost) physically. And the key being with a totally accepting guy - a marvalous guy, for the night. Wendy, I think my panties would of been wet.
I know all about the 2nd thoughts, what if.....Don't go past the night. As all of us CDers know - you have to enjoy the moment and do not expect anything from tommorrow. Every day as a CDer is a risk. Sometimes you win, sometimes you lose, but most of the time it is what you make it and only by risk.
Windy, I percieve you to be very much a CDer and woman at heart. And definately not a novice at this. Enjoy the chance of being a woman. If it ends with a wonderful evening as a Windy and He - you have been more of a woman than I have. If it goes further - sexually - be a woman (as you and I want to be) and I am confident you will know when it is to call it a night and a relationship. Dont think like a man -think like a woman. Carpe diem.:angel:
All my love,
Stephanie

Quote:

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Originally Posted by windycissy

I never in a million years thought this would happen, but I've started dating...as a woman. A few weeks ago, I hooked up with another CD'er who was visiting Chicago and we spent some time together en femme. We really hit it off, although we have very little in common except our crossdressing. I asked him if he would ever want to go out sometime with him as the guy and me as the girl, and he said okay.

The next time he was in town, he asked me out on a date! I know this sounds ridiculous, but I was so nervous putting on my makeup and deciding what to wear. I really wanted to look pretty for him. He may be a "plain Jane" as a girl,but he is a very good-looking guy and a well-mannered gentleman. After he picked me up, it was one thrill after another as he opened doors for me and told the waitress that "the lady will have...." I took his arm as he walked me home, which felt wonderful, and when we kissed goodnight, it seemed so natural.

He's been back twice since then, and last week I cooked dinner for him. You should have seen me in my apron setting the table and lighting candles. It is all so innocent: we haven't gone beyond hugs and kisses - we are both straight - but I am starting to like this way too much....

Usually I'm the one giving advice, but I could sure use some now. Should I break this off before it goes too far? Or just enjoy it while it lasts and see what happens?

Windy

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Dear Windy
Once again, a passable and very CONVINCING CD women enforces what I have been saying for so long. I am a male admirer, a gentleman who adore being out and about in public with a CD women who enjoys the magic of the moment to the nines. I have said it so many times that their are many CD women who will, given the opportunity, swoon and just be lifted to a new level, new heights in CDing when out and about with a "gentleman" escort. The feeling, the excitement, the thrill of it all just overpowers you and the experience is breathtaking. I know just how you feel because I have seen this happen on many of my CD friends who have gone out with me in the general public and just enjoyed being a women totally. Yes, make it go as long as you can because it will be for the time being..heaven on earth.
Jerry

Thank you all so much for your uplifting messages of encouragement! The big lesson I am taking away from your thoughtful responses is, go with my heart and stop thinking so much!

Many of you have weighed in on behalf of my man. Let me tell you, he is a few years older than I am, very worldly-wise, and unbelieveably sensitive about the turmoil I am going through....yes, we have been very open and candid about our feelings for each other. Our exchange of emails has been more erotic than anything we have done during our fleeting moments together. He has a good head on his shoulders, and is very protective of my feelings. Is this guy perfect, or what?

Our next date is in two weeks. I've been threatening to buy a little black dress so he can take me to fancy restaurant. Chances are, we'll have a long, chatty dinner together and wind up back at my place. I am just going to let things happen!

Windy

Windy. You sound like you've been having a great time and are comfortable with what's going on. If you've kissed a man and it felt right then there's nothing wrong with that. You have to go with how you feel not how other people will feel. If you're comfortable with it then let it happen and don't look back.There is nothing wrong or bad with what you are doing if you are not hurting someone else. You are doing what everyone has the right to do. Be yourself. Enjoy your life because it's very short. You only get one shot. Big hugs and you have my best wishes and support.:)

Love
Jeannie

Windy you are on course for something wonderful,I bet. Any girl born on St Patrick's Day can't go wrong. It's the luck o' the Irish, lass.

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Originally Posted by windycissy

Our exchange of emails has been more erotic than anything we have done during our fleeting moments together. He has a good head on his shoulders, and is very protective of my feelings. Is this guy perfect, or what?

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Oooo-ho! You didn't tell us about the emails!!! Sooo, the wild thang card is already on the table huh? You've been holding out on us darlin. :p

I recommend candles in the bedroom, maybe a little Van Morrison on the stereo.

Actually, he does sound pretty perfect.

Windy,
O my! Wendy! - girl! My heart faints at the emotions you must be going through. Thrill, happiness, excitement, anticipation and ..... All the thoughts of every woman - every WOMAN who has had the date of their life. This time you are the woman and you will do fine. Its in you.
What is going through my mind if I were you: lose weight, shave my entire body, perfume, hose, earrings, hose, that perfect black dress (just the thought is so efem), perfect heels, clean bed sheets, towels and woman's pajama's and how to be efem in the morning after????? I would probably be watching every movie made where a woman went out with a man - passionaltely - to study femine mannerisms. So much to do in 2 weeks. What torture!
Other than that I would enjoy the rare opportunity of being a woman - far beyond many of us other CDers her on cd.com would dream about. Girl, what a testiment of you being a woman - accepted by a man for another night!!:angel:
Love,
Stephanie

Hun, I would say that love is between two people. No matter what the actual gender. It does not matter what I say or anyone else does say. If your in love then this will be a wonderful year for the two of you. Lets us all wish you the best, and I so hope that things go well for you in your life my Sister.

Haley:)

omg.... need an update as soon as possible on how it's all going!!

This is so interesting: I'd love to be in your position, with a guy I trust who can accept and embrace the fem side in me. To be entirely fem, with a guy, for a whole day would be truley amazing, something I would relish and could probably never let go.

My thought is, remember the intimacy... I was always slightly envious of the girlfriend I got closest to, and envious of her ability to just fold up into my arms and feel protected. I WANT THAT!! Relish it. You have it.

Take care, and update us ASAP xx

Windy, being close to someone is the most treasured experience in life, well mine anyway. Good luck, I hope it works out like you dream!
Mona

windy dear....how i envy you...please let yourself go where it will...i would so love to have the opportunity to be wined and dined and treated as a total woman...as everyone else has said....if you enjoyed that kiss...well then enjoy more...oh to be a woman in every way possible you go girl!!!!...love ericalynne

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Originally Posted by sherribicd

I'm going to out on a limb here and speculate that if you liked it when he held you and kissed you, you may be ripe for more. To me, kissing a man is kind of a litmus test. If your reaction is "Ewww!", then you're probably not wired that way. But if your reaction is "Mmmm, that's nice", then ... well, you know.

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That was one of my biggest surprises. If you had told me even a few weeks ago that I could ever enjoy kissing another guy, I'd have said "No way!" For some reasons, my inhibitions vanished that night. Maybe it was the way he treated me totally like a woman. I remember during dinner, I thanked him for taking me out and told him what a good sport he was. I'll never forget his reply: "Windy, right now you ARE a woman, and you look better than a lot of the women I've gone out with...." I just melted.

The whole night was like a fantastic dream that I never wanted to end, and when he kissed me, it was soft and sweet. And I really did say to myself, "Mmmmm, that's nice!"

Windy

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Originally Posted by windycissy

That was one of my biggest surprises. If you had told me even a few weeks ago that I could ever enjoy kissing another guy, I'd have said "No way!" For some reasons, my inhibitions vanished that night. Maybe it was the way he treated me totally like a woman. I remember during dinner, I thanked him for taking me out and told him what a good sport he was. I'll never forget his reply: "Windy, right now you ARE a woman, and you look better than a lot of the women I've gone out with...." I just melted.

The whole night was like a fantastic dream that I never wanted to end, and when he kissed me, it was soft and sweet. And I really did say to myself, "Mmmmm, that's nice!"

Windy

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You are going to have to share this guy !!!!! He's too good to be true. Maybe cuz he dresses he's a great empathizer.

A cute black man kissed me once when I was dressed. He was so cool about it, he smelled great and his lips were so full and soft ... it was very nice. It's not always that way. Depends on the guy, I think.

BTW, if you'd like to talk about it, I'd like to hear your thoughts on switching. If it comes up, how will you feel, and how will you handle it?

Oh go for it, why not, im straight also, but if I had the chance I would go for it also.

Counting the hours till my next date with Mr. Right! He is taking me to a super nice restaurant, and I am in a tizzy over what to wear. On our very first date, I wore a simple skirt, sweater and flats. He took my picture, it is very fuzzy but can you tell from my body language how like a girl I was feeling?

http://im1.shutterfly.com/procserv/4...5108IatWLlw0aW

I will keep you posted as the magic hour approaches,

Windy

A good debater can argue both sides of an issue, so I'm going to argue the other side again.

A lot of crossdressers and other transgendered individuals often go though a phase of "gender euphoria." This is a time when the TG individual is fully engrossed in living as the other sex. This could be brought about by a change in circumstances, a more accepting spouse or SO, whatever. But whatever the reason, the TG individual feels much freer to express the other gender. During this time, the TG acts, with respect to his/her gender, with all of the insight, forethought, prudence, and experience of a thirteen-year-old. The euphoria of finally begin a woman (or a man) causes the person to go to extremes and do things that she (or he) would not normally do. Later, as the euphoria wears off, the person is left with many regrets for things said and done that were not well thought out.

I would caution you to therefore go very, very slowly. Dates are ok. Beyond casual dating lies a huge potential series of problems. Where do you go? Do you become a gay couple? Do you transition and live as a woman? Do you both live as women? What happens when the fling is over? Where do you go from there? What about your other interests, family, and friends. Will you tell them? What will you tell them?

Think first. It's easier to think first and leap second. It's hard to unleap. Which reminds me of an old, bad joke. What's the difference between a light bulb and a pregnant woman?

Warm regards,
Christina Nicole

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Originally Posted by Christina Nicole

What happens when the fling is over?

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Your points are well taken, Christina, but I think that Windy is in no great danger as long as safe sex is practiced.

Flings have happened since time began, and in this case, the other party doesn't even live where she does, so impacts on existing relationships are unlikely as long as she doesn't talk about it.

The important thing about a fling is to recognize it for what it is and not get unduly invested in it, emotionally or otherwise. If not for flings and affairs, those of us not in capital-R Relationships would be SO lonely!

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Originally Posted by Christina Nicole

What's the difference between a light bulb and a pregnant woman?

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That's ONE thing a Tgirl doesn't have to worry about. :p

Rachel xx

I think the euphoria thing is a common phenomenon, and the sad fact is that for a CD flings tend to be the norm rather than the exception, butwho's to say they can't settle into a sane long-term relationship. Windy may be a tad euphoric right now (I know I would be), but she has a good head on her shoulders.

To me, the biggest blip on her radar screen is the bedroom scene. Having no experience and not knowing how she will feel about it all, it should be interesting. Wish I could be a fly on the wall. :p

Sisters,

Methinks this conversation has taken place millions of times at slumber parties and sororities through the generations, without the twist;)

I know I am giddy over what's happening to me, in fact my boyfriend teases me about acting like a teenager. But we are both mature adults, so our hormones aren't exactly raging. Last night I reminded him of the old Frank Sinatra song:

"We're on the road to romance, that's safe to say,
But let's make all the stops along the way...."

It's the same old dilemma all women face: I want to keep my self-respect, but I want him to ask me out again too. I do have an edge though: I know how many ways there are for a girl to please a man....

Windy

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Originally Posted by sherribicd

... the sad fact is that for a CD flings tend to be the norm rather than the exception ...

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What's wrong with that? Many don't want a committed, long-term relationship - or are already in one. :p

Don't want to sound like I'm bashing and I hope you don't take it that way however keep in mind we all enjoy crossdressing and pretending to be women, pushing the envolope going out trying not to be noticed, hiding who we pretend to be from our freinds and family. But when you cross that line you are then a homosexual. Period. All the clothes and makup aside you are a guy sucking another guys d***

And your point is....

For what it's worth there is such a thing as bisexuality and in fact studies show sexuality is spectrum that society pretends is a duality.

I detect a whiff of homophobia here ... TG phobia is a close relative.

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Originally Posted by Pamela girl

But when you cross that line you are then a homosexual. Period.

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Or bisexual. Or, just adventurous. Or curious. Or eager to please.

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Originally Posted by Pamela girl

All the clothes and makup aside you are a guy sucking another guys d***

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If you are a girl doing one thing, then you are a girl doing anything. There are many acts that may or may not take place between a Tgirl and a boy or another Tgirl.

Girls, girls....remember how you told me to stop worrying so much about what was happening to me, and just go with my heart and enjoy the experience of dating a handsome guy?

I promise that I am not scheming about how to get Mr. Right into the sack! I really like him, he treats me like a woman and makes me feel like one, and if we snuggle and have a little fun after he takes me home, is that so wrong? I am a totally straight guy, but when I become Windy I want to experience life as Windy....call me curious, call me confused, call me crazy, but I've never been happier.

Tomorrow will be so much fun! Today I bought a little candy cane pin to wear on my sweater. I've always envied girls who get to dress up for the holidays...now I'm one of them! He's picking me up at eight tomorrow night, and I just hope I can get some beauty sleep. Wish me luck!

Windy

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Originally Posted by windycissy

Girls, girls....remember how you told me to stop worrying so much about what was happening to me, and just go with my heart and enjoy the experience of dating a handsome guy?

I promise that I am not scheming about how to get Mr. Right into the sack! I really like him, he treats me like a woman and makes me feel like one, and if we snuggle and have a little fun after he takes me home, is that so wrong? I am a totally straight guy, but when I become Windy I want to experience life as Windy....call me curious, call me confused, call me crazy, but I've never been happier.

Tomorrow will be so much fun! Today I bought a little candy cane pin to wear on my sweater. I've always envied girls who get to dress up for the holidays...now I'm one of them! He's picking me up at eight tomorrow night, and I just hope I can get some beauty sleep. Wish me luck!

Windy

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Dear Windy
PLEASE tell us all about it and if you can.....take some wonderful pics of yourself.
Jerry

Windy, I guess I am the only member who wouldn't do what you have done. But I guess you can't help it if he's a real handsome guy. Would he permit you to post a pic of him here so we can see him?

Can you name the specific places in Chicago where you've gone out with him?

In all my life in Chicago I never saw a CDr out with a man in regular public places.

Well, if it goes too far I guess you have become gay ?

There she goes again. :loser: Jesse's got a track record of being pretty negative, Windy. Just take it with a grain of salt.

I used to live in Chicago so I know what a wonderfully accepting town it can be. I say more power to you, Sister!

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Originally Posted by Pamela girl

Don't want to sound like I'm bashing and I hope you don't take it that way however keep in mind we all enjoy crossdressing and pretending to be women, pushing the envolope going out trying not to be noticed, hiding who we pretend to be from our freinds and family. But when you cross that line you are then a homosexual. Period. All the clothes and makup aside you are a guy sucking another guys d***

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It amazes me that people even care.

Wow, Windy. That sounds like a dream come true.

Life is meant to be enjoyed. Don't worry if people think you're gay, crazy, or whatever. All that matters in the end is that you don't do anything that can hurt yourself or others. As long as you stay safe and honest with yourself and your new beau, I see absolutely nothing wrong with your situation.