First Kiss

[Debs]

I want that first kiss so much now, Shall I let him touch me as well ?, I go out regular to bars and clubs, but ive never done any contact in anyway, might be a girl, i dont know, but started to dream about a kiss, silly I know but going to let it happen ? any of you girls got advice ?

[Beverley Sims]

Take care, assess the situation carefully and and be truthful of your intentions if you wish to go further.

[Lori Ann Westlake]

I have no experience in this area, Debs, since I've never sought such an encounter. However, Beverley's advice seems sound common sense. I'd say it's strongly advisable to think this through in advance, anticipate, and be prepared. How do you plan to respond in such-and-such a circumstance? What will you do if a guy wants a lot more than a kiss? What exactly is he likely to want anyway, and how do you feel about that? And if he wants to go further and you don't, how are you going to handle that diplomatically to avoid getting in trouble? That kind of thing. And don't forget, the reality may turn out quite different from the fantasy!

Oh, and I meant to add: Never promise anything you can't deliver. That can be dangerous!

[Helen_Highwater]

Debs,

The closest I've come to it was a few years ago when I'd met up with someone from the forum.

We were sat at a large rectangular table in a quiet LBGT friendly pub chatting, sat at the other end of the bench seat was a solitary guy.

Anyway he got talking to us and the evening passed pleasantly and then it was time to leave. Coats on, handbag sorted, we gave each other a friendly hug and a goodbye kiss on the cheek.

Didn't feel strange, really the natural thing to do so I guess for you I'd say if it feels right, that your spider senses say all is good, then let it happen. Don't force it, you'll know if the time is right.

[Julie MA]

Debs, Only kiss someone because you want to. Not because you are dressed. I am bi so have kissed both men (while dressed and not dressed, wink wink) and women. If you are not bi or gay the first kiss of a man will be unusual. I prefer women, so kissing them is always better. Beards and stubble just aren't as enjoyable, for me. Julie

[Sandi Beech]

Hey Debs, the only advice I have is if you are planning to kiss anyone, get you some liquid lipstick because it dries and will not smear all over the place. One time I was in a bar and this woman tried to kiss me on the lips when I had cheap wax lipstick on, and I had to turn my head really fast to avoid the lip smear. Whew. You can Google for kiss proof lipstick and get some hits on favorites. I use the Est?e Lauder, but I am sure there are other good ones. I keep mentioning it because I can not believe how much better the liquid is. Note: it does require a little more effort to clean off your lips.

Good luck.

Sandi

[MonicaPVD]

That first kiss can and will be magical but you have to take a few things into consideration beforehand. There are very specific types of men who are into crossdressers. Some of these can be quite undesirable. Others can be wonderful. Your goal is to end up with one of the latter. Stay far away from a guy who sees you as a sex object or fetish. Simple. Run fast in the opposite direction. Otherwise, have a blast and tell us all about it.

[Kris Burton]

At risk of sounding ridiculously naive, how would you know?

[MonicaPVD]

Kris, not sure if your question was directed at me but, in case it was, you would know because the guy will sexualize the conversation right away. He may start by letting you know that he is turned on, that he has a thing for CDs, and that will quickly turn into him saying that he would like to engage in certain activities with you. Basically, he will sound like a horny to pervy teenage boy talking.

Contrast this with a man who simply finds you attractive and can sustain a normal adult conversation without telling you how many CDs and trans he's been with, or what he did with them, or that you are so sexy, etc etc ect.

[Krisi]

Keep in mind that you ae still a guy, even though you are presenting yourself to others as a woman. If you kiss a guy and he later finds out that you are another guy, things could turn ugly very quickly. Crossdressers have been killed for this. Seriously.

Secondly, even though you are presenting as a woman, sex with another guy is gay sex. If you are gay, that's fine. If not, don't think that strapping on a pair of boobs and throwing on a wig is going to change this. It's still gay.

Do what you want, of course, but think it all out first and be sure you understand what you are doing. And avoid alcohol, it clouds your decision making ability.

[Rhonda Darling]

And by all means, keep control of your drink! Can’t say it strongly enough. Many a girl/woman or TG has succumbed to a roofie.

Be safe above all else.

[mbmeen12]

Beards and stubble just isn't as enjoyable Or is it lol?
You can keep dreaming or make it happen Debs...Be safe and enjoy life with no regrets....My worst nightmare, Im in a nursing home and looking out a window, living in regret.

[GraceH]

I've kissed men a few times in my life, but never had much desire to. However, kissing another woman while both of us are wearing lipstick is a really interesting sensation. Stay safe and do what feels right, and good luck.

[Lori Ann Westlake]

...even though you are presenting as a woman, sex with another guy is gay sex. If you are gay, that's fine. If not, don't think that strapping on a pair of boobs and throwing on a wig is going to change this. It's still gay.

Although I have no practical experience in this field, I don't entirely subscribe to this view. At least, I see it as more complicated than that. Mainly, I wonder what the purpose of this reminder is, which I've seen expressed several times here before.

OK, technically and anatomically it is indeed "gay" sex. So is the purpose to remind people that any sex they have with a man is bound to have certain anatomical constraints? If so, fair enough! But is that something that anyone is likely to forget, even in the face of an overwhelming fantasy? Does anyone need reminding on that score?

How about what the male partner expects, and how he's likely to behave with a crossdressed partner? That's another matter, though it's something I know little about, except for the "obvious" things. Something I don't know, a key question in my mind, is what kind of man is attracted to crossdressers. We've been told that gay men usually aren't interested, who otherwise would be looking for "gay" sex. But I'm not clear why straight men would be interested either. Not unless they can sustain in their minds the illusion that they're having sex with a woman. I wonder if the men most attracted ro crossdressersare actually bisexual, and are seeking to enjoy the experience of sex with someone appearing to be both sexes at the same time: "the best of both worlds," so to speak.

Anyway what all that boils down to is how a male partner is going to "see" a crossdresser in his mind. Is he going to treat her as a woman, as far as possible, sustaining her own fantasy of "heterosex" in a female role? Or just as a "man in a dress" who's expecting "gay" sex, ruining his crossdressing partner's experience? So yes, a warning could be needed for that reason.

However, apart from those matters of what to expect in reality, there's also the question of how sex is subjectively experienced. Much of the enjoyment (or otherwise) of sex is in a person's mind, which can include whatever fantasies or illusions they're indulging at the time. There seem to be a number of crossdressers who wouldn't be caught dead having sex with a man while in a male role. The idea of "gay" sex turns them right off. Yet when dressed and "feeling feminine," the idea of sex with a man may be attractive. It's as if dressing really can effect a "personality change" for some, and as long as they can "see themselves" in the role of a woman, sex with a man can seem more natural.

I suppose being "properly dressed for the part" removes inhibitions against playing a female role, if one has the inclination. This doesn't seem surprising to me. After all, any of us can feel embarrassed or stupid if we're not "properly dressed" for some social role that involves interacting with others. Suppose we turned up to a "black tie" dinner in tatty jeans and a T-shirt. Or arrived for work at a construction site in an Armani suit and tie, where everyone else was wearing hard hats and steel-toed workboots. In either situation we'd feel awkward, stupid, "out of place," wondering what people were thinking of us. But if we're wearing suitable clothing for the role or occasion, we can "fit right in" comfortably.

"Clothes make the man," as they say, but they can also "make the woman." So I guess sex with a man is more possible and desirable for a crossdresser who's dressed for the part" in female clothing, a wig and the rest of it, while wearing male clothes would never work. The latter would just feel "all wrong," "too gay" entirely, while wearing women's clothes makes it feel "all right." There might even be a "chicken-and-egg debate" about this. Does the eroticism of wearing women's clothing arouse, in some, a desire to play the part more fully by having sex with a man? Or does a covert wish to experience sex with a man prompt some to "dress properly" for the part, in order to enjoy it freely?

Regardless of that, I imagine many crossdressers would not want to come away from a sexual encounter thinking they "just had gay sex," even if in objective terms they did. The subjective experience is all in the mind. From that viewpoint I would say that what they had was not "gay" sex, but TRANSEX! Sustaining that illusion as far as possible would be vital to the enjoyment of the encounter--which is the point of sex, after all. I'm sure nobody would want the illusion of Transex to be spoiled!

[Sometimes Steffi]

So, I've never kissed a guy. I'm not into men.

But, I did kiss a woman that I met at a bar, maybe even two or three kisses. Some alcohol might have been involved on her part but not mine. It was actually quite great. I was a little embarassed when I found out that the guy sitting next to her on the other side was her date. But he didn't seem to mind and she certainly didn't.

Then there was the CD I kissed (for about 15 minutes). It was surprisingly arousing. I won't say any more than that because good girls don't kiss and tell. And no, I'm not accepting the gay label just because of a makeout session with someone who is technically a guy. As Billy Joel sang, "She's always a woman to me."

[Kris Burton]

Kris, not sure if your question was directed at me but, in case it was, you would know because the guy will sexualize the conversation right away.

Contrast this with a man who simply finds you attractive and can sustain a normal adult conversation without telling you how many CDs and trans he's been with, or what he did with them, or that you are so sexy,

I did not specifically direct the question to you Monica, but it was good of you to answer, keeping us all aware in no uncertain terms what to watch out for. I certainly understand the allure, and the ease in which we can find ourselves in trouble - so a good PSA for us all. As you say in another post though, if all is clear, have a blast!

[Steph7]

A good girls don't kiss and tell. But with my wife we enjoy our adventures.

[GretchenM]

Lori, I love your examination of this subject and I agree with it. It is a lot more complicated than it seems on the surface.

[AngelaYVR]

Everyone has mentioned to watch how you will feel but nobody has mentioned how the guy might feel. If he is new to doing this too he might have regrets after and possibly become violent. So keep your spidey senses turned to 11.

As for the assertion that gay men would not entertain the thought of being with a cross dresser, this is quite untrue. I have had two dyed in the wool gay men express their sexual interest in me. It is flattering if nothing else!

[Jodie_Lynn]

My first kiss, as a girl, was with a man who had a full beard and moustache. I LOVED it, because it made me ( as smooth as a china doll ) feel so femme in His arms as his tongue probed my eager mouth! Yeah, I felt soft, and femme, and putty in his arms!

The fact that HE was a hairy beast, compared to my smooth skinned, feminine presentation, merely brought home the fact that HE was the predator, and I was merely his ( ahem, willing ) prey!

[Kris Burton]

The fact that HE was a hairy beast, compared to my smooth skinned, feminine presentation, merely brought home the fact that HE was the predator, and I was merely his ( ahem, willing ) prey!

Or perhaps more powerfully, he the pursuer and you the pursued that has accepted his advances.

[Charlotte Haynes]

Yes. Make sure your breath is minty fresh.

[krissy]

My first kiss was with my wife her friend came over and wanted to do my make up my wife agreed .after she did my makeup i went upstairs to get dressed. i came down i felt so pretty her friend put lipstick on herself and my wife put some on too ill never forget that great soft gliding lips and the taste of lipstick.it was so hot and i cant get over how good it felt .and i kissed my crossdressing uncle on the lips it was ok but i liked the wife a lot better:daydreaming:

[Maria 60]

I've never kissed a man and wouldn't even think of it, but saying that I wouldn't want a man touch me. But if you read some of my older post I was in a situation dressed and a man was talking to me and put his hand on my leg. It sent a tingle up my spine, but I believe it was the feeling of his hand on my pantyhosed leg that made it feel great. But thinking about a man feeling my leg while in male mood wearing shorts I don't think it would be so excepting.
I guess we have to be in the situation but sometimes my wife's biggest worry is she sees my desire when dressed how I just act and move different and believes it would be more about a person exceptiing me as a women that may make me do something against my morals. Almost like thinking I'm passable or a man believing I'm a women. But the thought of a man kissing me in male mode, I wouldn't even think of it. My only advice is make sure it's something you want to do and the biggest thing is as the others said is to approach it with great caution.

[NaughtyMichelle]

Wear good quality lipstick, keep breath mints handy and let your consience be your guide. Observe how women kiss in public depending on the place and circumstance.

No matter how much you want to be kissed, don't let anyone be disrespectful.

[Debs]

Believe it or not was out last weekend, got pulled into a lesbian group, they was amazing, one of them but a big smacker on me by suprise, wasnt sexual, and just left me gobsmacked, lol, then said things to me that made me felt amazing

[Di]

Ok just going to ask because I am confused.

First kiss = as in first while dressed?
Cause I know you are married and said recently she has been more lenient since covid.
So it like a fantasy thing? ( Sher was always Sher no matter the clothing she had on)
You feel like a different person because you have different clothing on/ so again first kiss dressed ?

Does she know you are on a quest to be kissed?
Just asking because some wives have helped in that - having that experience ( have read here)

So from your post …..pulled into lesbian group and kissed ….is different?.

because you are dressed as opposed to being kissed by wife?

Was not going to ask but after your response I just am more confused…..so asking.

Mean no harm, just want to understand .


I just do not get it…….and I am trying to understand.

[Jodie_Lynn]

Backing up what Di is asking.

[Ilsa]

I can only fantasize of being held or kissed by a man and that man would be Cary Grant! Alas, that will never happen.

[LydiaL]

My first kiss while dressed was with another cross dresser. She was my host on a visit to Las Vegas. A kiss way more passionate than a mere peck on the cheek!

[Jodie_Lynn]

Or perhaps more powerfully, he the pursuer and you the pursued that has accepted his advances.

Indeed, a more correct expression! We did play the game of pursuit and capture, while I 'ran away slowly'! LOL

Way back in the day, I remember playing the same game, but on the other team. I also remember the doubts. "Is she...? "Does she...?" "Can I...?" Now though, I KNOW what his goal is, and that the 'pursued' has a lot more power than the 'pursuer'. You can shut him down with a sentence, or encourage him to pursue with a meaningful glance and a smile.

And, unless he is a misogynistic, violent, misanthrope, you can terminate the chase at any point. Luckily, I have the knack of evaluating people quickly, and the nasty ones get closed out fast and firmly.

- - - Updated - - -


I want that first kiss so much now, Shall I let him touch me as well ?, I go out regular to bars and clubs, but ive never done any contact in anyway, might be a girl, i dont know, but started to dream about a kiss, silly I know but going to let it happen ? any of you girls got advice ?

Never done any contact in anyway...

Honey, I'm hoping that you don't take this harshly, but.... GO SLOW! Don't just give in to the first man that chats you up. Yes, I KNOW how exciting that can be, and if he appeals to you, then go for it! Kiss him, get in the clinch with him, and see how YOU feel when his hands start to roam over your body. DON'T be afraid to stop when you feel you've reached your limits. Make sure that you are in a public, or populated locale so that he can't force you into a situation you aren't ready for. Don't be afraid to yell for help!

A lot of folk ( CD, Trans, and otherwise ) fantasize about things, but when they actually start to happen, find themselves overwhelmed and in a state of panic. And sometimes, fantasies are best left as fantasy. Reality seldom, if ever, matches our dreams.

[char GG]

And sometimes, fantasies are best left as fantasy. Reality seldom, if ever, matches our dreams.


I'm also trying to figure out how this works. So, out of curiosity, does your wife know this fantasy of yours? Do you think she may have the same fantasy for herself with another man or woman? Do you consider your marriage an open one? Do you consider yourself "another person" when you are dressed?

You probably won't have a hard time finding someone to fulfill a fantasy. Would your wife be broken-hearted if she knew what you were doing or looking for?

Wondering what the goal is? Does it stop at a kiss? Is there a goal? (Oh so many questions!)

Just try make sure that you don't bring any cooties home to your loved ones.

[TexasLegs]

Advice?

Sure. It is a slippery slope though I suspect you're already sliding down it.

Should you do it? It's probably inevitable so why not? I love kissing men when I'm dressed, as long as they have good hygiene. I love the feel of their stubble on my face reminding me of what I'm doing. It's exciting and passionate and taboo.

[Joni T]

L-o-n-g story short. I was enjoying an evening out dressed at a drag show in L.A. about 30 years ago. I noticed an older gentleman eyeing me. I went over to him and we had a nice conversation. We exchanged phone numbers and I went out with him a couple of times. On one occasion we wound up in his hotel room. We got as far as kissing--passionately. I felt dirty afterwards. We went no farther than passionate kissing. I never called him again. These some 30 years later I still feel dirty when I think about it. No thanks. This girl's had her fun.
Joni

[Rachelakld]

Having stubble touch my lips was a shock and I'm not a real fan of it, not far off a Liverpudlian kiss as far as I'm concerned.
You might find softer kisses further south (London).

[JuliaDLS]

Personally I love kissing men as long as they don't have a bad breath. I just don't understand people who aren't aware of how much their breath stinks.
I'm not passable as I'm tall with big hands and feet so I'm not worried about a man getting angry.
But then I just love a big, hunky man. Older, mature and beefy. Skinny guys do nothing for me.

[Ressie]

I used to wonder what it would be like to be kissed by a man. They have lips and a tongue right?

I can't explain the feelings I had the first time a man held me in his arms and made out with me. In a word it was "heavenly". It happened around 6 or 7 years ago and I've made out with several other men since. If you're curious about this, put it near the top of your bucket list! PM me if you wanna hear more about it ;)

[MonicaPVD]

If you kiss a guy and he later finds out that you are another guy, things could turn ugly very quickly. Crossdressers have been killed for this. Seriously.

Actually, no crossdresser has ever been killed for this. The men always know. Crossdressers and transwomen have been killed by men who already knew what the crossdresser was but were overcome by guilt, shame, or rage at the prospect of engaging in homosexual activity. This is particularly common immediately after intimacy in what some refer to as post-nut clarity.

This has nothing to do with a violent, unstable, insecure man being fooled by a crossdresser. It has everything to do with the man being violent, unstable and insecure in the first place. Know who you are dealing with before you go down that road and be ready to walk away.

[Pumped]

Sometimes when I am in that "moment" I also wonder. Then I realize I think most men are gross and have zero desire to get that close to one. It would have to be the right guy and I would be extremely picky, so I don't see it happening.

I sometimes wonder what women see in most men! So many are way over weight, and personal hygiene ? Or lack of it? Real life is not like the movies!

[AmandaM]

You have to be careful here. Reality might not be the same as fantasy. I've tried it with a CD'er. We ended up in bed. But, after that, it just seemed so mechanical. Nothing like with women. Could I do it again? Maybe, with <long list of criteria of fantasy - see romance novel covers>, but other than that, no, not really. So, reality is never going to fulfill this specific longing.

[Marissa Q]

We got as far as kissing--passionately. I felt dirty afterwards. We went no farther than passionate kissing. I never called him again. These some 30 years later I still feel dirty when I think about it.

No disrespect intended, Joni, but -- by that same logic -- should we feign surprise if some GG SO's feel "dirty" kissing another CD/woman? "Dirty" works both ways.
I'd also like to say that none of us should feel any guilt/shame if we kiss or become intimate with a man anymore than with a woman. Only infidelity is 'dirty'; same sex intimacy isn't. Ever.


It would have to be the right guy and I would be extremely picky, so I don't see it happening.

I sometimes wonder what women see in most men! So many are way over weight, and personal hygiene ? Or lack of it?

That's easy. Most women simply stop being "extremely picky" and move on to building a relationship, for better or worse.
There are likely many of us here who are already the beneficiaries of such largesse.

[Felicia M]

Debs, totally get it and I hope you find what you are looking for.

Lori Ann - your reply on sex/Transex is a masterpiece. Thank you!

[Charlotte Haynes]

I have kissed a crossdresser while dressed as a man. I felt as if I were kissing a woman. Initially I was very aware that I was with a man but after that it all felt familiar. I have also had sex with men and other cross dressers while dressed myself. This always feels like I am kissing a man. It is not unpleasant.

[ReineD]

Secondly, even though you are presenting as a woman, sex with another guy is gay sex.

I agree with your basic idea that wearing women's clothing does not change someone's sex. A CDing male is still a man with male anatomy.

But does it matter what label we put on it, like "gay sex"? Although homosexuality is more accepted in our society than it was 50 years ago, the term "gay" still has negative connotations to a lot of people. I prefer to think of it as "same sex", which it is. That's not to take away from what goes on in people's minds when they have sex. All kinds of people fantasize about all kinds of things when they have sex, especially I suspect CDers and the men who go for them. :)

[valerie anne]

I have always shied away from sex with men, which is why I attempt to present as a soft & compliant woman, or as a "lady boy" such as they have in SE Asia.

Men can vulgar, coarse, aggressive, hairy & smelly.

I would much rather snuggle up to another CD or a natural woman, particularly as we would share interests such as lingerie, heels, makeup and clothes.

[Pumped]

I agree with your basic idea that wearing women's clothing does not change someone's sex. A CDing male is still a man with male anatomy.

But does it matter what label we put on it, like "gay sex"? Although homosexuality is more accepted in our society than it was 50 years ago, the term "gay" still has negative connotations to a lot of people. I prefer to think of it as "same sex", which it is. That's not to take away from what goes on in people's minds when they have sex. All kinds of people fantasize about all kinds of things when they have sex, especially I suspect CDers and the men who go for them. :)

I don't think "gay" is any better or worse word then "same sex" or "homosexuality". There is a three letter "F" word that is no good, that is definitely negative.
Kind of like I know some people that dress in women's clothing, but they are not CD'ers!

[AmandaM]

"Gay sex" is not a good description of us. That assumes both partners are men and only looks at the physical body, not the mind.

[docrobbysherry]

It sounds like most of u r naive and inexperienced when it comes to men! A have had a number of men and CD's come onto me. Even tho I told them I wasn't interested!:thumbsdn:

But, let me tell u, NONE of them were interested in kissing. Unless it was me kissing their male parts!:devil:

If u want to make out with someone? Try another CD! I've seen countless such acts at the many T events and clubs I've been to!:o

[Devi SM]

I would like to go deep asking you, why you want a kiss with a man?

Many, and it was my case, confuse gender with sexual preference.

To want to dress and be treated as a woman doesn't mean you should like men.

Be careful with it because in the search of an identity, teenagers make so many mistakes, and we as crossdressers, exploring our identity, commit so many mistakes too.