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Chateau Heartiste

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Take The Midnight Tran

February 1, 2008 by CH

Sometimes when you date a girl she drops hints that send up red flags.

“I usually need to get to know a guy before I have sex.”

“I don’t drink.”

“Ew, you’ve done it in there?!”

“I missed my period. Oh, and I’m pro-life and my dad’s a paternity lawyer.”

So it was with some trepidation that I dated this one girl who joked a few times about being a tranny. On our first date I mentioned I liked her artsy shoes and punk makeup and she said “Yeah, I bet you think I dress like a tranny.” OK, that got me concerned. I looked more closely at her shoes and face and wondered if it could be true. She didn’t have a low voice but I’ve read about cosmetic vocal cord surgery for old people who want to sound younger.

The second date we were making out and groping and I reached down and ran my hand under her skirt and near her pussy, hoping to put my worries to rest. She gently pushed my hand away, smiled, and said “Are you checking if I’m a tranny? Naughty.” Now I was really freaking out on the inside. When people blurt out weirdness more than once it is a sign of them hiding something. Could she really have been a man in her past? Was I going to have a crying game moment? She didn’t look like a tranny, but with the state of medical science these days you can’t take anything for granted.

Between the second and third dates I dwelled heavily on the possibility that she might be a guy with one operation to go, or a former guy with a butchered fake vagina constructed out of sheep intestine. A few sleepless nights passed. I googled “transsexual dead giveaway” for information about warning signs. I contemplated not calling her back. Nope, I had to see this through.

On the third date, sex was the farthest thing from my mind. I was concentrating hard on inspecting her head to toe for traces of maleness. Again, she let slip with an awkward “joke” involving the word tranny. Mentally, I was a mess. I thought about how she walked with this loping bouncy gait. And how she had these exaggeratedly feminine gestures in the way she sat down and crossed her legs very slowly, and how she carried her purse dangling off her forearm with her elbow bent at 90 degrees and her hand turned upward, palm out. Oh my fucking god, that’s what trannies do! Then I remembered… she was always paying me blatant compliments about my physique. Girls never do that on the first couple of dates, even when they are completely into you. 100% tranny. 100%.

The squirrel in my head was running frantically on his wheel.

Still, she looked pretty good, so I started french kissing her. Gradually, I moved my mouth down and kissed her neck. I began probing her throat with my tongue. This aroused her suspicion. 

“What are you doing?”

Think. “Mm, I love kissing your neck. So smooth.” Like a giraffe reaching out for the highest succulent acacia leaves, my tongue pressed around the area where her Adam’s apple would be if she were a man. I detected nothing. Phew! Or did she have it surgically removed? I pulled back for a visual examination. No scar. Phew again!

Occasionally, I would stop and stare deeply into her eyes, but what I was really doing was getting in close to see if she had the shadow of a mustache or a missed spot of stubble. I wondered if an entire beard could be lasered off. No, her face was hairless and of an even coloration. Another test passed. I glanced at her forearms. Also hairless. So far so good. I gripped her hand; she gripped back. Not too strong, it was an appropriately weak girly grip. Feeling better. I moved my hand under her shirt and burrowed under her bra. This was the first major test. I squeezed and kneaded like I was giving her a breast exam. Then I pushed aside her bra and pinched a nipple. It got hard and pointy. There’s no way a fake tit or hormone replacement could do that. I was confident enough to move to the final stage.

In the bedroom, I lit a small candle. I would need some light to work by. Best to get this over with quick. I maneuvered my hand up her skirt and placed it on her crotch. Her panties felt thick, padded. A rush of fear. Was s/he tucking? For the first time in my life I prayed that a girl I was about to fuck was on the rag.

This was it. Crunch time. No turning tail now, I had to know. But the risk was huge.

Other than blowing out my ass with explosive diarrhea in public while wearing white linen pants, I can’t think of a more psychologically scarring scenario than reaching into a girl’s panties and grabbing a schlong. I had already made up my mind to soldier on because I calculated that the regret of giving up sex with a girl was worse than the regret of having near sex with a man.

Off came her shirt. A muscular back. Stay focused.

I pushed her backwards onto the bed and pressed into her pelvis. Nothing rose on her to meet my erection. Do or die. I closed my eyes, grit my teeth, and ripped off her skirt and panties and in one mighty uninterrupted motion plunged my hand into her furrow.

Labia. Wet. Hole. Wet. Clit. Wet.

A wave of relief swept over me. I pried my eyes open and smiled warmly at the authentic vagina before me. A short sniff of my fingers confirmed the presence of natural juices. No lube.

Afterwards, she snuggled in my arms and belched. I dumped her a week later.

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Posted in Dating, Ridiculousness | 55 Comments

55 Responses

  1. on February 1, 2008 at 2:19 pm noxxy

    wow…

    LikeLike


  2. on February 1, 2008 at 2:29 pm mike says

    why the fuck would you go back for more if you thought there was even a chance of swordplay?

    “I had already made up my mind to soldier on because I calculated that the regret of giving up sex with a girl was worse than the regret of having near sex with a man.”

    No. No no no. Times are never that hard.

    LikeLike


  3. on February 1, 2008 at 3:09 pm Hope

    Sometimes when you date a girl she drops hints that send up red flags.

    “I usually need to get to know a guy before I have sex.”

    “I don’t drink.”

    “Ew, you’ve done it in there?!”

    Definitely some warning signs that indicate a player should stay away. Many have commented that women who don’t slut around, have one nighters, don’t drink/party/do drugs/smoke or engage in overly pornstar-like activities would make good long-term relationship/marriage material (except for David Alexander, of course).

    These are all things a 15 year old girl would say, to put it in Gannon’s words.

    LikeLike


  4. on February 1, 2008 at 3:12 pm DF

    This post goes down as one of your all-time best. Hilarious.

    Now I don’t know whether to admire you [for your determination] or make fun of you [for your morbid curiosity].

    LikeLike


  5. on February 1, 2008 at 3:19 pm Reggie

    Did you ever find out why she kept making repeated tranny references? That’s a strange joke for a woman to make. It would be like a man saying, “I’ll bet you think I’m a wife-beater, right? Ha ha!”

    LikeLiked by 1 person


  6. on February 1, 2008 at 3:30 pm Pagan

    Did you dump her because of the belch? Or because the novelty wore off?

    Forgive me, I’m new to your blog. I had to see what all the fuss was about.

    LikeLike


  7. on February 1, 2008 at 3:48 pm C.M.

    Dear God! You got the same thrill out of that as one would out of an extreme sport. I get the same feel out of that description as out of ‘I escaped death by a narrow margin’. You glory in this mad explicit description, don’t you?

    Oh, thank GOD those lines keep the men away. I like to throw in a strictly religious now and then, though I always fear some would view it as a ‘challenge’ or something equally ridiculous.

    I love me daily roissy updates; you’re spoiling us.

    LikeLiked by 1 person


  8. on February 1, 2008 at 3:53 pm Virgle Kent

    “Other than blowing out my ass with explosive diarrhea in public while wearing white linen pants, I can’t think of a more psychologically scarring scenario than reaching into a girl’s panties and grabbing a schlong”

    OH YOU ARE SOOOOO getting free shot and round of drink from me this weekend for one of the funniest lines ever written on a blog….. period

    LikeLiked by 1 person


  9. on February 1, 2008 at 4:07 pm TracyLord

    please say she was really hot…megan fox looks like she could be a tranny.

    LikeLiked by 1 person


  10. on February 1, 2008 at 4:30 pm Raleighwood

    Sounds like you may have dumped her because the excitement of her possibly being a man was gone.

    LikeLiked by 1 person


  11. on February 1, 2008 at 5:24 pm GJ

    Having been in a similar situation (which also had a happy, non transsexual ending, mercifully), I could barely bring myself to read this post. I kept scrolling down and reading ahead, praying it didn’t end in tragedy.

    Hall of fame post.

    LikeLike


  12. on February 1, 2008 at 7:44 pm T

    You do know that trannies now have lubes that simulate the feel and scent of natural vag and stay moist all day long, right?

    Nah, just playing.

    LikeLike


  13. on February 1, 2008 at 8:57 pm finefantastic

    “Other than blowing out my ass with explosive diarrhea in public while wearing white linen pants”

    You promised you wouldn’t tell anyone about that….it was ONE TIME.

    LikeLike


  14. on February 1, 2008 at 10:43 pm Topshelf

    I can’t stop laughing. This blog is supreme. Praise to Roissy!

    LikeLike


  15. on February 2, 2008 at 12:40 am johnny five

    time for the new math:

    I can’t think of a more psychologically scarring scenario than reaching into a girl’s panties and grabbing a schlong
    plus
    because I calculated that the regret of giving up sex with a girl was worse than the regret of having near sex with a man
    equals
    wtf?

    i’m a bit nonplussed, roissy: you don’t seem like the type who’d accept high risk without high return. and if sex with a girl who gives you that much heebiejeebieage is high return, methinks there must be a drought on the pussy farm. (or at least was, at whatever time you wrote this)

    i mean, if a piece of chicken kept making salmonella jokes, i wouldn’t eat it if there were other skewers lying around. just sayin’

    LikeLike


  16. on February 2, 2008 at 1:53 am Peter

    Like a giraffe reaching out for the highest succulent acacia leaves, my tongue pressed around the area where her Adam’s apple would be if she were a man.

    Classic. Truly classic.

    LikeLike


  17. on February 2, 2008 at 2:24 am dchero

    hahahahah, this is some quality shit

    LikeLike


  18. on February 2, 2008 at 2:52 am hexedit

    Whoa….that was a sad story.

    LikeLike


  19. on February 2, 2008 at 3:31 am alias clio

    Whoa nellie. It’s a long time since I ran into a male member of our species who knew what “nonplussed” meant. Not to mention “heebiejeebieage”.

    Is Roissy being bested on his own turf?

    LikeLike


  20. on February 2, 2008 at 3:51 am TracyLord

    roissy – $10 on nonplussed…

    LikeLike


  21. on February 2, 2008 at 4:53 am cjm

    at least it wasn’t a 31 year old 😛

    LikeLike


  22. on February 2, 2008 at 5:10 am anonymous

    For the life of me, I can’t figure out why anyone would want to pursue anything with that much trepidation going in. Isn’t that always a recipe for things turning to shit?

    LikeLike


  23. on February 2, 2008 at 5:22 am anonymous

    Yes, it’s me. The trouble maker. I love this story of roissy’s. It’s by far the dumbest thing I’ve heard all day…maybe all week. I actually went to a funeral today and I realize more than ever how people don’t really have time to waste on b.s. like “overcoming one’s fear of tranny’s” in order to get laid. Was it worth your precious time, roissy? I mean you pumped and dumped again. So what? This is amusing? Yeah, I guess it is!

    LikeLike


  24. on February 2, 2008 at 3:42 pm suicide_blond

    i think it would have made for a better story..if she HAD been a tranny..:-(…
    well..maybe not better for you…. but better for me.. and ….really…everyone knows im a narcissist…
    xoxo

    LikeLike


  25. on February 2, 2008 at 4:30 pm Reggie

    Also, you said in a previous post that you couldn’t achieve a full erection with a woman over 30, but here you seemed to have no trouble with a person who may have been a man. Interesting.

    LikeLike


  26. on February 2, 2008 at 4:55 pm roissy

    she didn’t look like a man. she was a decently attractive woman. my paranoia was triggered by her tranny jokes and odd gesticulations.

    why i decided to close the deal:

    sex was a sure thing. all i needed to do was stick it out for 3 dates. zero cost to notch her. when the pussy is that convenient the low risk of surprise penis is outweighed by the reward of easy sex with a new conquest. variety is the spice of life and contributes to the value of the reward.

    also… i had to put my mind at ease. if i had stopped seeing her before finding out her true gender i would have spent the rest of my life in a state of unpleasant flashbacks remembering how i made out with a possible man. when i discovered that she had a real vagina i was free to dump her unencumbered.

    LikeLike


  27. on February 2, 2008 at 4:58 pm roissy

    reggie – the sex was not good for me. but the denouement was.

    alias: Is Roissy being bested on his own turf?

    all your roissy are belong to us.

    LikeLike


  28. on February 2, 2008 at 5:03 pm jaakkeli

    What’s the big deal? If a chick I was getting it on with turned out to be a guy, I’d likely just burst into laughter and decline the dick. No reason to be all Woody Allen about it.

    My theory is that this is why some of you guys have to learn from “pickup artists” and internet gurus: you have some strict belief that having sex with a man is “degrading”. If you didn’t, you really wouldn’t care about it if you accidentally fooled around with a man (or an ex-man or whatever). Women are magnificiently intuitive creatures and they can smell it on you that you’d judge them for having sex with you, so they’ll make you wait until you’ve fooled yourselves into believing that you have some connection (or whatever it is that makes it OK for a girl to have sex with you in your mind).

    Maybe you guys should forget those silly magic tricks and start working on getting rid of silly sexual insecurities.

    LikeLike


  29. on February 2, 2008 at 5:10 pm alias clio

    “all your roissy are belong to us.”

    I’m sure this means something but don’t know what it is. I can’t tell whether it’s got a typo or else some obscure allusion or piece of slang that an Old Lady like me can’t get.

    LikeLike


  30. on February 2, 2008 at 6:27 pm Sockless Joe

    Alias Clio – “All your roissy…” is an allusion to the moronic internet phenomenon “All your base are belong to us.” That phrase is part of a really bad script translation in some obscure video game. If you google “all your base” you will more than have your answer.

    LikeLike


  31. on February 2, 2008 at 7:21 pm bully for you

    What a man.

    LikeLike


  32. on February 2, 2008 at 7:34 pm inquiring mind

    I really want to know, roissy, if you ever seriously spend any amount of time and energy examining your self in relationship to women. Do you not ever find that doing the same thing over and over and over and over and getting the same result is a bit disappointing? How many more of these types of stories are you going to spew out for our supposed enjoyment? I mean, what was your childhood like? Was your mother abusive?

    LikeLike


  33. on February 3, 2008 at 12:30 am Rain And

    A very similar story happened to one of my friend’s loser white trash cousins. Except in that story, when the panties came off there was no wet lady hole… only dong.

    And jaakkeli would be proud, after a brief period of disgust, he started routinely cheating on his ugly, handicapped wheelchair girlfriend with the more attractive and non-disabled tranny.

    LikeLike


  34. on February 3, 2008 at 7:16 am mq

    Jaakkeli nails it. A lot of weird insecurity in this post.

    LikeLike


  35. on February 3, 2008 at 8:17 am johnny five

    Is Roissy being bested on his own turf?

    i’d better watch out, lest roissy precipitate my demise, and then celebrate the decreased competition that would ensue (a la heath ledger).

    $10 on nonplussed…

    when i was a stripling, big words were worth a shiny new quarter, and the tooth fairy only brought 10 cents. am i that old?

    LikeLike


  36. on February 3, 2008 at 9:08 am johnny five

    #19 alias clio a male member of our species who knew what “nonplussed” meant.

    yeah, you wafer-eaters aren’t as smart as some of ’em, i guess. ha!

    LikeLike


  37. on February 3, 2008 at 6:25 pm alias clio

    now, johnny five, where did you get the idea that I based my assessment of men’s vocabularies on Catholic men?

    LikeLike


  38. on February 3, 2008 at 7:34 pm ruby_tuesday

    Well, this was an interesting read. Your sarcasm is entertaining, and you sound intelligent, but you don’t seem to be at peace… When you desperately look for flaws in women you are bound to find them. It sounds like you’re looking for a perfect creature or you’re trying to prove to yourself that there isn’t one. Either way, you can’t win. You know this, of course, so it makes you bitter.

    Once you found out that she was a real woman you decided to break up with her. Why? Because she belched or because you started to like her? (there’s also a possibility that a man who’s sabotaging his relationships with women would prefer another man, but something tells me you’d take this as an insult. So, let’s say you’re not gay. Anyway, I don’t think you are. )

    Maybe you’re not ready for what you really want, and there’s nothing wrong with being single and enjoying occasional sex with amusing strangers, (just use condom, ok?) but judging from this story, you’re not really having fun. Your fear of women/commitment/love/ending up with a broken heart spoils it.

    I have a question for you, but you don’t have to answer to me, as long as you’re honest with yourself: What kind of relationship with what kind of person do you want (someday) and how do you perceive yourself in that relationship? It’s simple as that, but if you know this what’s stopping you from getting there?

    I hope you’re not offended by my comment. I only wrote this because I recognise some of my “old self” in your experiences. Believe it or not, many women could identify with your stories.

    ruby

    LikeLike


  39. on February 4, 2008 at 5:05 am anonymous

    38 ruby. I’ve tried to shock roissy into changing his behavior towards women. I’ve tried to insult him into it! I’ve tried to tell him how stupid it is to keep doing the same thing over and over and over. He prefers to listen to pickup artist losers like Mystery. Pump and dump, pump and dump, pump and dump… He doesn’t listen to me (naturally as my approach sucks) but you have a nice assertive manner about you. Maybe he will listen to you. But judging from his latest atrocity…I mean post…he still hasn’t got a clue. He makes the guys I know look like saints, but then I think he likes the negative attention and doesn’t really know how to get positive attention from women. He seems to have to dupe women into giving him any attention at all. And aside from the occasional disgruntled feminine type, most women who post here seem more interested in being his intellectual ‘equal’.

    LikeLike


  40. on February 4, 2008 at 5:30 am roissy

    Either way, you can’t win. You know this, of course, so it makes you bitter.

    funny, i don’t *feel* bitter.*

    *name that pop culture reference.

    Once you found out that she was a real woman you decided to break up with her. Why? Because she belched or because you started to like her?

    you’re overcomplicating things. i just didn’t like her enough to want to pursue anything more than a tryst. and there is the fact that once i’ve suspected a girl of being a man, even after being proven wrong, i never quite see her in the best possible light.

    What kind of relationship with what kind of person do you want (someday) and how do you perceive yourself in that relationship?

    you seem to be under the impression that i don’t have what i want right now in my relationships with women. there is no end goal here. i meet women all the time, date them for periods ranging from one night to many years, and occasionally fall deeply in love with some of them. as for how i perceive myself in these relationships, your question smacks of spreadsheet analysis — as if i should be doing this and this in order to enjoy the fruits of a successful love life. that is not how i operate. i am who i am, which is very good, and that is enough to bring to the table. women are very turned on by men who know themselves and don’t seek approval from external sources of validation.

    LikeLike


  41. on February 4, 2008 at 8:31 am johnny five

    #37 alias clio
    now, johnny five, where did you get the idea that I based my assessment of men’s vocabularies on Catholic men?

    that was a sad attempt at a joke, wherein ‘your species’ = wafermunchers.

    it gave me a nice internal chucklerumble to type it, even if you were bemused rather than amused.

    LikeLike


  42. on February 4, 2008 at 9:59 am HughRistik

    jaakeli said:

    What’s the big deal? If a chick I was getting it on with turned out to be a guy, I’d likely just burst into laughter and decline the dick. No reason to be all Woody Allen about it.

    You know what, I would have the same reaction as you. I really don’t get Roissy’s reaction either. But since I don’t get it, I wouldn’t be so quick to judge it. Just as there are men who are turned on by other men, and men who are sexually neutral to other men (no attraction; no repulsion), there are also men who are quite turned off by other men. I don’t think that either of those preferences are necessarily invalid.

    My theory is that this is why some of you guys have to learn from “pickup artists” and internet gurus: you have some strict belief that having sex with a man is “degrading”.

    There are many reasons, good or bad, why men learn from pickup artists. This is not one of them.

    If you didn’t, you really wouldn’t care about it if you accidentally fooled around with a man (or an ex-man or whatever).

    I don’t think straight men need to think sex with men is “degrading” in order to want to avoid fooling around with men. Straight men don’t want to accidentally fool around with men because they are attracted to women, not to men, and are often turned off by men.

    Sexual repulsion towards men could be due to socially encouraged hysteria about homosexuality, and/or it could just be part of the normal psychology of very straight men, in which case it shouldn’t be pathologized.

    LikeLike


  43. on February 4, 2008 at 1:38 pm ruby_tuesday

    Maybe I am “overcomplicating things”. If that’s the case, I’m sorry. But reading this and some of your other posts I was left under the impression that you’re a restless, unsatisfied person looking for something he doesn’t believe exists. Maybe I shouldn’t have said “bitter”. But do you ever go back and read what you wrote, and try to see a bigger picture? Do you notice how your view of women shapes your experiences with them? What if you’re oversimplifying things?

    I don’t know how feminine the woman you dated looked or behaved, but to dump someone based on your own suspicions, which are later proven wrong sounds like self-destructive behaviour to me. It has nothing to do with the other person. I wonder if you’re at least aware of that? Yes, I agree you are who you are, but it seems like you’re running away from that person…

    I’m not trying to tell you what you should do or what the social norms are. All I really said was that you don’t sound happy for someone who does whatever he wants. Casual sex without attachment can be fun for a while (and educational) as long as both know what they’re doing, I’m not judging that. But to boast about a lifestyle without an “end goal” is quite self-deceptive. You are heading somewhere whether you like it or not.

    I can’t speak for all women, but as for myself and my closest friends I can say what we have in common is that we are turned on by confidence and turned off by arrogance in men. There’s a fine line between these two and yet they are worlds apart…. I also believe without any doubt that we all attract our own kind and in the end get a taste of our own medicine. Maybe you should think about that next time you “pump & dump“ a woman. There’s such thing as karma, or cause and effect, if that makes more sense to you.

    39. Anonymous: I think of time and consequence as two best teachers in life. *Nothing* beats that. All we can do is comment, criticize or ignore. Or if you have a friend like that, stand by them and hope they come to their senses. But you can’t change anyone. Depressing, I know.

    LikeLike


  44. on February 4, 2008 at 4:52 pm anonymous

    43 Agreed. We can only change ourselves and that takes a huge amount of courage. It’s so much easier to see the self destructive behavior in others. Here’s a picture of my personal role model couple. It pays to know what you want. This is a beautiful image to me. Like you said, roissy (and all of us) are going somewhere whether we know where it is or not. I prefer to go consciously, but rarely does anyone do much of anything consciously.

    http://www.people.com/people/keith_urban/photos/0,,,00.html

    LikeLike


  45. on February 5, 2008 at 3:08 am HughRistik

    ruby_tuesday said:

    I don’t know how feminine the woman you dated looked or behaved, but to dump someone based on your own suspicions, which are later proven wrong sounds like self-destructive behaviour to me.

    To me, it sounds like this woman created a negative association in Roissy’s by repeatedly joking about being trans. I love women with quirky humor, but that is just off the deep end, and would throw up a big red flag for me.

    What if you were dating a man, who repeatedly made jokes about being a sex offender? Would that form a good association with him in your mind, even if you were absolutely certain that he was not a sex offender? Of course, being transgendered and being a sex offender are different; the point is that someone joking about being those things is going to associate negative feelings with themselves in the other person.

    Once you start associating a certain feeling with someone, it’s hard to change that.

    I can’t speak for all women, but as for myself and my closest friends I can say what we have in common is that we are turned on by confidence and turned off by arrogance in men.

    These preferences are quite typical according to the research I have done.

    Maybe you should think about that next time you “pump & dump“ a woman. There’s such thing as karma, or cause and effect, if that makes more sense to you.

    What some women have trouble understanding is that men don’t necessarily go around with the goal of pumping and dumping women as much as it may look like from watching men’s behavior. The fact is that the subset of women that men find attractive is much larger than the subset of women that are also relationship material.

    A man can go out with the goal of meeting hot women, and seeing what happens. During the process of meeting and sleeping with them, he can decide whether he wants a relationship with them. For a man with a lot of options sexually, most of the time he won’t find her up to his standards for a relationship, and he will dump her or they will become just friends. (However, if a man is going out and automatically pumping and dumping no matter what and not even considering women for potential relationships, then I would say that his behavior is immature and that he is limiting himself.)

    Now, from the outside, it looks like such a man is just going around pumping and dumping. But really, all those women had a chance to have a relationship with him. They just didn’t turn out to be what he was looking for, which isn’t necessarily anyone’s fault.

    In some cases, women actively bungle their chances of a relationship, like this woman did with Roissy. Since Roissy has had relationships in the past, he does not automatically pump and dump; he is just being selective about the women he has relationships with. Is it worse for a guy to be a little selective, than for him to get down on his knees and propose marriage to the first woman that will go out with him?

    When men like Roissy and I learn game, we end up fulfilling more women’s standards of attractiveness. Now that we have more choices in women, women are going to have to work harder to be the ones we choose for relationships. They may have to put in some work learning about our psychology, turn-ons, and turn-offs (e.g. joking about being trans), like we have done with theirs. I don’t think this is unreasonable.

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  46. on February 7, 2008 at 4:00 pm anonymous

    ^ Hugh

    “Now that we have more choices in women, women are going to have to work harder to be the ones we choose for relationships. They may have to put in some work learning about our psychology, turn-ons, and turn-offs (e.g. joking about being trans), like we have done with theirs. I don’t think this is unreasonable.”

    It’s perfectly reasonable, but reasonableness is not the be all and end all of relationships. There must be a certain magic involved that goes beyond reason. Would you agree? If a woman is twisting herself into a pretzel to please you, and is taking great pains to avoid any and all ‘turn offs’ so she can ‘qualify’ to be in your selective company, she is fucked and not in a good way. I mean, wouldn’t YOU be?

    The moment we consider more how someone ELSE thinks or feels about what WE are thinking or feeling we are fucked. I mean seriously fucked! Not that one should be tactless, obnoxious, and tiresome in the process. But you seem to be saying a woman needs to go through some kind of test in order to be in your illustrious presence. It seems if that is your state of mind regarding romantic relationships, you are simply not ready for one. Period. I think you need a whole different mind set, or you know what will happen of course. You’ll end up with someone just like you. They will require YOU to bend and twist yourself into a pretzel for THEM. I mean, isn’t that what you’re finding?

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  47. on April 13, 2008 at 11:25 pm One Year Anniversary: Greatest Hits « Roissy in DC

    […] A ripping good yarn about my time dating a woman I feared was a tranny. […]

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  48. on October 1, 2008 at 4:56 pm Evil Baby Shower « Roissy in DC

    […] I saved my mental health by fantasizing what it would be like to make gentle love to a third trimester pregnant woman. This is a mountain I’ve yet to climb. It couldn’t be any more challenging than this. Or this. […]

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  49. on October 1, 2008 at 5:31 pm Kick a Bitch

    did you dump her b/c she belched? you seriously didn’t stop beating that hole up b/c she belched did you?

    LikeLike


  50. on October 2, 2008 at 3:51 am Henner

    Memento would be the pop culture reference…great movie.

    LikeLike


  51. on August 20, 2009 at 6:54 pm Jay

    10/10. Would read again. Epic lulz were had.

    LikeLike


  52. on October 27, 2009 at 12:54 am Two Beautiful Black Women « Roissy in DC

    […] this post has tranny overtones, here is a classic from the archives about the time I feared the girl I was about to bang was a MAN, […]

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  53. on October 27, 2009 at 11:40 am JC

    Hahahaha nice. This is why i read your blog. Best writing ever. You should go Tucker Max and make a few bucks.

    LikeLike


  54. on October 27, 2009 at 1:15 pm Jean

    Ok, someone needs to chime in with a few details…
    Could be – might not be.
    1. Vocal chord surgery – very expensive, not very effective. Vocal therapy more useful, IE, training – which sounds like…
    2. Exaggerated feminine gestures – likely training, maybe to be extra-sexual, maybe to be uber-feminine, maybe because she was a he once.
    3. Scars fade.
    4. Hormones make nipples do interesting things – like get aroused – when the balance is Female instead of Male. Also make real breast tissue.
    5. Beard can be removed by laser or electrolysis. Permanent. Costly. ($100,00 or more sometimes.)
    6. Muscular back – not a dead give-away, depends on body fat %, exercises done, and time in gym. Very frightening experience: On Cardio deck, doink an elliptical, the treadmills were in front of me. Woman trainer gets on the treadmill in front of me – and I could pick out the muscle striations of her @$$ through her pants. Tight pants – scary sight.
    7. Height/weight/location/ waist:shoulder:hip ratios mean more.
    8. Skeleton is NOT genetically pre-determined. Put a pre-pubescent male on estrogen, he’ll grow up to look like a woman (and mostly think like one, and possibly commit suicide ’cause body doesnt’ match his mind. Assuming he’s “normal”, not transgender.)
    8a. Skeleton is formed pretty well by 14-18. Estrogen hardens the growth plates, making women shorter than men. Testosterone makes for heavier bones and more muscle, larger frame, V-shaped body. E makes for hourglass, and shoulders at about hip width, give or take, with a shorter lumbar spine and the pelvis shaped like a funnel.
    What we see as “hips” on a woman? They aren’t, those are the leg bones that have been pushed outwards by the shaping of the Pelvis, including the section of bone around the birth canal. Males have spikes there, BTW – to support our “(not so) Leetle Friend”… 😉

    If you go looking, especially at Thailand kathoeys, you’ll notice they look female. Only way to really find out if she wasn’t a she is to find pictures of her before the op; have obvious cues, such as shoulders wider than hips or facial hair; she gets wet from where you’ve seen her at “dry”; or she tells you. If she goes away dry and comes back wet – be afraid! 😉

    (Medicine was an interest of mine for years…)

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  55. on October 30, 2010 at 8:32 am NoisyBudgie

    Wow – you’re incredible. NOT.

    I remember a time not so long ago, when all manner of girl-variants received the same kind of caustic disrespect lavished with light floral scents you dish out on Transsexuals. Lesbians, female academic types with their “I’m a female academic” haircuts, kinky women, women who enjoy owning and riding motorbikes, all kinds of minority women. But of course, there’s always someone smaller to put down isn’t there? Hitler new that one.

    I work with a transsexual women and I mean a legitimate transsexual and not some Chick with a d*(&. We have become good friends and knowing her has enlightened me to the difficult reality of individuals who experience this condition. She enjoys a very typical life married to a loving husband. Theres no platform shoes and bad makeup. Together they raise their adopted daughter (she now 10 years old and delightful). Horror. Gasp. How normal.

    It’s very sad when a great writer (but would be thinker) jumps on the same transploitation dredge-wagon: The one that’s kept Jerry Springer in bad suits for years. The one that for so many centuries kept gays, lesbians, even feminists, in the closet (or worse). The same one that throws “get out of jail free” cards to murderers and thugs – because the frickin queer deserved it. Clearly you are on that train.

    I’m not going to wade through your vitriolic textural hate. What one says – says allot about them in which case you should really see a therapist about that insecurity of yours that sees you feeling good when you are cruel to those minorities you see as more minor than yourself.

    BLAH. UGLY

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