I've been dating a guy

[Jesse69]

There she goes again. 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!

Well, I still live in Chicago and they call me a nerd, gay, or unpopular simply because of my crossdressing. Maybe the only acceptance you'll get is from gay people. Truthfully I don't have any gay friends because I don't want it to lead to gay encounters. So I find Chicago is not too accepting of crossdressors. But they won't bother you on the street.

I've never gone out in drag so I don't know how people would treat me. But I would want to be perfectly passable if I do.

I don't believe in promiscious sex and I am still a virgin too. I don't want to catch any diseases from anyone. And I'm a good Catholic except for my crossdressing fetish / fault.

I think crossdressing is a somewhat bad habit I should quit. But I can't quit. And I would never purge what I got now. I think I should just stop buying more clothes, dress less often, and date girls.

I think those of you who dress up and have sex with men are going to far. But that's your lifestyle and I'm not stopping you.

[Abby Lauren]

Windy
We all have fantasies and the biggest one is that we are women. We all seek acceptance as women and nothing connotes acceptance as a woman more than someone who wants to love us as women. I have always been heterosexual and consider myself a lesbian but, were I in your heels, I can actually believe myself saying yes. Like you, I would never have believed that possible and I am not looking for this at all. But, the way you so beautifully described it, the moment was magical and you found yourself giving in to a wonderful sensation. You have no prior experience with this and have no idea where this is leading nor do you know for sure where you want it to go. Therefore, don't be in any great rush to fulfill a preconceived notion of where this is supposed to lead to. Try to be comfortable with yourself each step of the way. But, if it continues to feel right, it probably reflects a side of you you never knew existed- but it does exist, girl.
Very interested in where this is going. Just feel comfortable.
Hugs,
Abby

[Rachel Ann]

I'm a good Catholic except for my crossdressing fetish / fault. I think crossdressing is a somewhat bad habit I should quit.

Have you ever considered talking to a psychotherapist about this? You seem to have a lot of self-hatred going on, and that isn't good for anyone.

[Shelly Preston]

Dear Windy

I hope you have a wonderful time with this guy

If it leads to something more then hopefully it will seem like the natural thing to do.
Just be sure in your own mind.
You can always say no

As for being gay well how may labels do we have to choose from gay, straight, bi sexual, metrosexual, multi sexual, crossdresser, transvestite, transexual and many more. so should we label anyone ?

[windycissy]

Where do I begin?

He was a little late (as usual) but that was fine because I took my time getting dressed, I wore a short (for me) gray skirt, black top accesorized by a Christmas scarf and my candy cane pin, black hose and flats. Mr. Right had on a dreamy sport jacket, and looked quite dashing! He is taller than me when I wear flats, and I took his arm as he led me into the restaurant, which was just amazing. He presented me with a single pink rose, held back my chair when I sat down, and ordered a Lavendar Cosmopolitan for me - a girlie drink if ever there was one. It was delicious! He had a Manhattan. We talked about everything - movies, literature, music - and the one time I brought up how weird the whole thing was, he gently steered the conversation back to other things.

After we split a delicious crab cake appitizer, he had salmon, and I had scallops. Then he invited me back to his hotel room for coffee and dessert....

My head is still spinning. Let's just say he rounded second base and I stopped him as he was steaming towards third - the American girls will know what I mean. He was a perfect gentleman as he escorted me back to my place, and we exchanged the perfect CD christmas presents: clip-on earrings for me (they are elegant!) and I gave him the jumper that I wore the night I made dinner for him (because he kept going on about how much he wished he had a dress like that).

There is only one thing wrong with this guy: he is the world's worst picture-taker! Or do you think maybe he was a little nervous? That blur you see is me in my Christmas outfit, holding my rose:



I may see him again before he leaves town....

Windy

[sherri]

Second base ... hmmm, I'm trying to figure out what that was exactly ...



Sounds like a wonderful evening, Windy. So how do you feel about the whole thing? What are your thoughts? What's the prognosis?

[Sweet Susan]

As an example of how amazing this thread is, this is the first multiple page thread ever that I have read each and every word of each and every posting. Simply a thriller in action. The suspense from page one where it all began and page three where we currently are has been fascinating. What we call in literature a page turner! What we call in baseball a cliffhanger, a hell of a game!

Cissy, I don't know where to begin but to say, 'you go, girl.'

Like Sherri, I am baffled about rounding second, but stopped short of third, so I'm going to just say the hell with it and take a stab at what I think you meant, as well as speculate on what it all means. Please take no offense, and for those of you who don't enjoy a good game of baseball, stop reading now.

First base, based on your original post, must be the first date and the kiss good night. Not sure what the kiss good night could really mean, because I've had good night kisses that were just a peck, and I've had good night kisses that were tongue jobs that left me limp and full of desire. Anyway........

Second base would have to mean sitting on the sofa and doing some serious necking. Rounding second, but denied third is a bit confusing. Was he thrown out trying to reach third, or did he safely return to second? Was he caught in a pickle, made a mad dash and slid safely under the short-stops glove to second? Was it even a close play? Or did he simply round second, stop, look, and return to second. You mentioned that he "steamed toward third," and you stopped him, so I'm assuming he actually made a serious attempt at reaching third.

Regardless, it is safe to assume that since he reached second, he accomplished more than a pleasant kiss goodnight, which, as I see it, would be a mere bunt. In my mind, reaching second would have to result in serious erections all around. I only bring this up because it would play into the matter of you being or not being a "straight guy." Obviously, that is not the case. In fact, if you were straight, you would have not asked him if he would consider dating you with you being the girl and he being the guy. Nope, if you were a straight guy you would have kept it simple and simply met and dressed together. After all, straight is straight.

Third? Just what exactly is third base? I would have to believe that third is where most of us would like to get. Obviously a home run, whether it is an inside the ball park home run or a fence clearing blast, would be out of the question for many of us, but a delightful, bench clearing celebration for others. I see third as anything from, between, and to heavy kissing, fondling, nakedness, oral sex; the sequence beginning at heavy kissing and fondling and ending at oral sex, with any stop along the way. I would think that for your friend to reach third base would be an extremely good show of excellent base-running or a good clean hit down the sidelines that caused your outfielder to make a late defensive throw. After all, triples are hard to come by. (Then again, they might be easy to come by, depending on your expectation.)

Whatever. Cissy, I'm thinking that you are in this for what it brings, and it may bring a pennant. Who knows. Nonetheless, I think it only proper to remember your youth and what it felt like to be teased. Your friend is expecting to hit a homerun, and why shouldn't he. If you don't want any sluggers on your turf, then you need to think about calling the game because of rain, because I have to believe that while his intentions may be honorable, there are only so many pitches a batter can let go by before he unleashes a blast to bring the fans out of their seats.

[Darlena]

Good for you Windy! You are so very lucky. And he sounds like a dreamboat. Don't let the naysayers and homophobes decide for you and ruin your chance for true fulfillment. The ones who say "no" are just being anal anyway. Love & kisses,

[Linda-x]

It's tough to keep a score card, but I don't see any errors..LOL The urban dictionary is a little fuzzy on 2nd base, but it is generally fondling the breasts, but could be a little more, and third base is oral stuff. And I think we all know what 4th base is !! So you gave him a dress? Is he a CD'er too, or was it just fore keepsake?

[womanatheart]

Has this not been the post of all times! It has for me. Windy - thanks for putting up with all of us. You have had your own emotions leading into this special night/moment and then listening to the chatter of the 100s of friends who chimed in (onlookers). You have taken our peering so graceful. Which is exactly how I imagined you are. Quite a woman.

Pamela Girl: your comment about being "gay". It provoked me to think all day on that. My conclusion is: there are many examples when the mind will over ride the body; old person lifting a car in an emergency, POW actually visualizing golfing, basketball players improving free throws by only visualizing. My point; I believe a cder can actually mentally think oneself to be a woman. Gay? No. Woman? - Yes. Have desires of a woman? Yes.

Love,
Stephanie

[Abby Lauren]

I agree that this is a wonderful and unique thread and I, too, eagerly await the next installment. I'm also rooting for both of you, girl.

[Jesse69]

Have you ever considered talking to a psychotherapist about this? You seem to have a lot of self-hatred going on, and that isn't good for anyone.

Yes, I've gone to a Psychotherapist a few times. All he said was that it's ok to be gay & etc. Figures he'd say that when he counsels a lot of gay. I was made to go because of probation for punching someone. Otherwise, I would never have seen a psycho.

I don't hate myself. It's just that people hate me (for crossdressing).

I guess from this thread it shows where other cdr's stand on issues with dating a guy.

[windycissy]

Has this not been the post of all times! It has for me. Windy - thanks for putting up with all of us. You have had your own emotions leading into this special night/moment and then listening to the chatter of the 100s of friends who chimed in (onlookers). You have taken our peering so graceful. Which is exactly how I imagined you are. Quite a woman.

It is I who must thank you and all the girls for your wonderful words of encouragement. To those who have expressed their misgivings, rest assured that the same thoughts have tormented me too. To those who have cheered me on, your support means more than you'll ever know. I have no clue where this will lead to, but it helps immeasurably to have this forum to share my journey with.

Mr. Right just called and asked me to have breakfast with him tomorrow at his hotel! I told him I would be taking a calculated risk to let him see me in broad daylight, but if he was game, so was I. So tomorrow morning, I will call in sick, put on a skirt and we will try to make small talk over coffee and newspapers....

I wonder if he will bring up last night? I am sorry if I was too opaque in describing our bedroom scene, I did not want to appear indelicate. What happened was this: we kissed, he started to get hot, then I had an inspiration and fondled him with my scarf. He loved it! I took off my skirt, what a feeling when he stroked me through my nylons! We were both getting pretty close, until I got cold feet and broke it off. Get the picture?

Virginity intact. Totally screwed up in the head. That about sums me up,

Windy

[Kimberly]

Awww, hunny.

Things are moving along, but take time over it!

Welcome to the world of a confused 19yr old

[Rachel Ann]

Second base ... hmmm, I'm trying to figure out what that was exactly ...

The urban dictionary is a little fuzzy on 2nd base, but it is generally fondling the breasts, but could be a little more, and third base is oral stuff. And I think we all know what 4th base is!!

Ummm, never heard of 4th base, Linda - but it sounds exotic!

First base, based on your original post, must be the first date and the kiss good night. … Second base would have to mean sitting on the sofa and doing some serious necking. … Third? Just what exactly is third base? I see third as anything from, between, and to heavy kissing, fondling, nakedness, oral sex; the sequence beginning at heavy kissing and fondling and ending at oral sex, with any stop along the way.

I suppose I’m showing my age here, but when I was in HS, 1st base was anything from her neck up, 2nd base anything above her waist, and 3rd base was anything below her waist short of a Home Run, which speaks for itself. His neck and waist may have figured in the stats but didn't count towards the outcome of the game.

Kids did it back then, it just wasn’t talked about except for locker room lies. Some guy once asked a smart-ass question about syphilis in “Boys' Hygiene” class and the teacher said that the word ought not to be in the vocabulary of a student at that school.

Rounding second, but denied third is a bit confusing. Was he thrown out trying to reach third, or did he safely return to second? Was he caught in a pickle, made a mad dash and slid safely under the short-stops glove to second? Was it even a close play? Or did he simply round second, stop, look, and return to second. You mentioned that he "steamed toward third," and you stopped him, so I'm assuming he actually made a serious attempt at reaching third.

Sounds to me like it may have been a rundown. I heard no mention of another base runner who might have been tagged for the third out.

Regardless, it is safe to assume that since he reached second, he accomplished more than a pleasant kiss goodnight, which, as I see it, would be a mere bunt.

I once saw Rickey Henderson get a double off of a remarkable bunt that made it well in to left field. Tony La Russa was furious, because Rickey was supposed to swing away, stop at first and steal second. But I guess actual baseball is a bit off-topic here.

[sherri]

we kissed, he started to get hot, then I had an inspiration and fondled him with my scarf. He loved it! I took off my skirt, what a feeling when he stroked me through my nylons! We were both getting pretty close, until I got cold feet and broke it off. Get the picture?

Boy do I! Love the scarf thing, that does feel good. But that poor guy, stranded on second with no one to bring him home! Sounds like he's cool though. Scoring a run is great, but the base running is at least half the fun.
So what kind of feelings are you having about the whole thing?

[Linda-x]

Ummm, never heard of 4th base, Linda - but it sounds exotic!

OMG !!! I didn't realize until now what I had written. LOL I am such a silly girl!
I meant home plate, or whatever !
Windy, let us know how breakfest goes !...

[windycissy]

So I got out of bed, and went for a long, long jog along the lake, lost in thought about what was happening to me....

Almost as if I was being pulled along by an invisible force, I showered, put on my makeup, did my nails, and got dressed. Normally this time of year I wear pants, but I put on a skirt and nylons for my breakfast with Mr. Right. Brrrrr!

It was very daunting, walking into the lobby of his hotel. He put me at ease immediately with a peck on my cheek and a cheery "Hi, honey!" We went into the breakfast room, and he made them give us a nice table overlooking Michigan Avenue. We went to the buffet line, and he helped himself to a huge plate of bacon and eggs, while I worried about my girlish figure.

At first, the conversation was very stilted. I can't remember who broke the ice finally, but we started to talk about our feelings, and soon it was the best conversation with him I have ever had. It was our fifth date after all, so we know each other pretty well by now, and nothing was held back as we talked about our feelings for each other.

He says he loves me, and I have feelings for him, but we each have our "real" lives and who knows when we'll see each other again. We both agreed that it is a break that we live far apart, otherwise the inevitable trajectory would result in a forced, unhappy ending before either of us were ready.

I just re-read the above, it sounds so heavy! One amusing vignette: I discovered that he was staring at my legs, and took great amusement in crossing them and tugging at my skirt as I felt the power all women have over a man....

Girls, I truly have no idea where this is going, but we are having a lot of fun. When we left the restaurant, we each got out cigarettes, and when he forgot to light mine, I punched him in the arm. He got out his lighter and the look on his face said, "Women!"

Windy

[Rachel Ann]

My point; I believe a cder can actually mentally think oneself to be a woman. Gay? No. Woman? - Yes. Have desires of a woman? Yes.

Right on, Stephanie! I am ACHING to find someone hold me and take me - even though my "sexual preference" is still for GGs.

[Abby Lauren]

Oh Crissy
You write so well and so descriptively that I could well imagine myself preparing myself for my date and thoroughly enjoying the sensations on the date.
Mind you, I never ever had an inkling that I could feel this. So, it's a tribute to your writing and empathic abilities to evoke these feelings.
I'm actually sorry for myself that it has been at least temporarily suspended. Like a good novel, I will miss it. Please let us know if anything further transpires.

[KewTnCurvy GG]

Our little novella of sorts
Well, I think ppl get way too hung up over what's is str8, what is gay and what is bi. For whom do these labels really serve? I think it's more for the ppl who don't want to be indentified as something that is 'less' than whatever is considered socially acceptable (again, for whatever that means). Somehow I don't envision that 'gay ppl' went around saying, "what do we call ourselves?" "Gee, we don't want to seem unhappy or unapproachable, why don't we call ourselves 'gay'!" Seriously, kidz, think about it.
That is all, carry on............

[Janice Ann]

Windy--gawd I wished I had that problem

[GirlyGirl]

windycissy, you are living the dream girl.

GG

[RobynP]

Windy,

You should read Alice in Genderland: A Crossdresser Comes of Age, by Richard Novak, M.D., if you haven't already.... The description (from amazon.com) is:

Alice in Genderland tells the story of Dr. Richard Novic, Harvard-educated psychiatrist and crossdresser. No memoir like it has ever been published. Most of the time, he is a man at the office or a husband and father at home. But one evening a week, she is a woman about town, shopping, dining, dancing, and dating a man for over five years. And it’s all out in the open.

Robyn P.

[Christina Nicole]

My point; I believe a cder can actually mentally think oneself to be a woman. Gay? No. Woman? - Yes. Have desires of a woman? Yes.

When I'm Male I'm 100% Male and will kick Ass and Rumble, I work with a lot of tough mother*******, but when I'm Jenny I am 100% Jenny and if, as you put it I wish to suck someones **** then I will, and I'll make a good job of it! I will fullfill my role as a girl, for me its not Homo, But 100% hetero, he's a guy and I'm a girl so leave Windy to make her own choices as to how far she goes and Windy I am GREEN with envy Have fun girl be carefull but enjoy.
Love and Hugs.
Jenny.

Well there goes the argument that many CDers have used with wives and girlfriends. Now one can't say, "It's only clothes." Nor can one say, "What I wear doesn't change the person I am inside." Because, if a crossdresser says either one to his wife or girlfriend, she will "know" that he wants to date men and sleep with men. It says so right here on this forum.

In an oblique way, this also demolishes the argument that when a woman wears slacks, or a men's shirt, tee, etc that's she's crossdressing just as he is. It eliminates that argument because when she puts on that shirt, she isn't looking to be all the man that she can be by dating another woman and taking her to bed.

There are quite a few other CD/TG themes that I could deconstruct pretty effectively with this thread, but the point should be pretty clear. Threads like this make life a lot harder for the crossdresser with a non-accepting, or at least a questioning spouse or significant other.

Warm regards,
Christina Nicole