how many of you CHB deviants have slept with trannies/shemales/whatever?


  • Plenty

  • Just once. I swear.

  • Never in a million years

Results are only viewable after voting.


Bosomus Maximus
Jun 14, 2012
I remember Hillary Duff was like the "All American white girl" poster girl for the early to mid 2000s. I didn't realize she had an ass like that though.
She didn't, and my nieces who watched her when they were kids call bullshit on any suggestion it's a natural endowment. That was actually part of her original appeal, that like her cultural predecessor Melissa Joan Hart (in Nickelodeon's '"Clarissa Explains It All"), she was NOT "hot," but an "average" and "normal" girl. (Young girls were entirely their fan base. Boys had posters of Jennifer Love Hewitt, NOT Duff or Hart on their bedroom walls. Selma Blair was the one they wanted blowing them though.)

Melissa Joan Hart appears to have matured naturally and been presented differently for Sabrina and her Maxim magazine spread, but not in a way I haven't seen girls change in real life. (I'm not saying MJH hasn't had surgery done, but looks as though it's possible her appearance and change in presentation were achieved in ways not involving anesthesia.) For Sabrina, MJH lost adolescent baby fat, her belly flattened, and she was exercising and watched what she ate. Later, she packed on over 40 pounds and then lost it in a way that we often see with childbearers.

There's been speculation that Duff either had work done, or that pregnancy and motherhood somehow inflated her body like puberty usually would. I vote for surgery as the reason for her current physical appearance. We've seen girls inflate during puberty. No physical transformation like that happened to Duff over the course of Lizzie McGuire by the time that series ended.

What she looks like now was purchased as an investment in her career, standard operating procedure. (I'm not sure Miley Vyrus has ever gone under the knife BTW. She's talentless and disgusting with all her tattoos, piercings and antics, but she's still basically just an older Hannah Montana physically.)

One of my nieces has giant boobs but a flat ass and narrow hips. Another niece of mine has a big butt, but is flat chested and is looking to get a boob job before her wedding. They both tell me what other ghetto bootied girls I've worked with in the past have said. Giant boobs may or may not sprout at puberty, but they either always had a butt, or they didn't.

MJH has broad hips, but her ass never ballooned like that. Jessica Simpson has big boobs which she complained were shrinking when she tried Atkins, but she had to (yes, this is an absurd way to describe it...) work her skinny ass off to build her ass up to fill out a pair of Daisy Dukes for the Dukes of Hazzard movie.

No way Hillary Duff somehow grew her rear trunk naturally AFTER puberty. Jessica Simpson showed the limits of using exercise to grow one, and Melissa Joan Hart showed where post partum pounds go on a broad hipped white chick.


Bosomus Maximus
Jun 14, 2012

And @Duo quoting the fuck out of @PityTheFool :rofl
Carles, you evil, manipulative son of a bitch!...

@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
@Duo quoting the fuck out of @PityTheFool :rofl
Do you realize what's going to happen if you cause him to return to this thread?. Do you know how RAW and emotionally VULNERABLE this thread has made him?? (I blame YOU, cause I'm a lazy and irresponsible asshole...):

Reactions: techks and Carles


Freedom Fighter
May 14, 2013
Castle Duckula.
Just think of this, one day you could be fucking a tranny, and then you find out after that it was some guy you knew from years back, like someone you didn't like from high school, or someone that used to post on esb.

Pretty sure that's a Eminem song....Come to think about it, his name was you, damn.


Friendly Troll
Jun 4, 2013
@Duo, you're really trying to end up on Pity's ignore list lol. If he comes storming back I'm not gonna be one fellate him for appeasement. I was already your booty call. You're on you're own dude.


Top tier
Jul 26, 2012
If it's some disgusting man with a wig like this thing.....Hell fucking NO... No one wants to date you not because your a tranny it's because you sound like a guy and look like a fucking creature.....

Now this on the other hand... I'll plow the fuck out of it....

Reactions: nuclear


Breakin it down.
May 16, 2013
The tree outside GABBY'S room
You're all up in the tranny mix now, officially an involved party. Relaaaax. Yeah, I agree though as I prefer my women to be women and men to be men too, but one can't deny the greatness that comes of some of these threads; which poster was it in that other one who came with:

While smashing she started calling me daddy, I randomly thought to myself "this used to be some poor dudes son"

Then I nutted


And I would never diss my boy @ScouseLad...

And why is Duo of all fucking people the most prominent poster in this thread? Fuck I shouldn't even be surprised. :lol:

I remember@anut posted some tranny pic back on ESB. Guys fell for it too until someone pointed out it being a trap due to the "brazilian" watermark in the upper corner.

I said I didn't see the watermark until I wiped the spooge off my monitor.
Reactions: ScouseLad


Bosomus Maximus
Jun 14, 2012

I remember@anut posted some tranny pic back on ESB. Guys fell for it too until someone pointed out it being a trap due to the "brazilian" watermark in the upper corner.

I said I didn't see the watermark until I wiped the spooge off my monitor.


So basically, you were skinning your monitor lizard...
Reactions: Icemmann
Jun 22, 2013
I've probably only seen about 3 trannies in real life. It really is crazy how the media blows this shit out of proportion.


CHB NYC Delegate
Jun 5, 2013
New York City
As promised here is my story:

About 6 years ago I was just coming out of a long term relationship and within a few months I met a girl named Julie, a pretty 23 year old university student and we hit it off quickly and started seeing each other in a FWB type of deal. One night after a couple of months of seeing each other we started discussing fantasies and she revealed to me that one of her biggest fantasies was to participate in a threesome with a man and a t-girl.

She asked me how I felt about helping her fulfill this fantasy of hers and I told her that since I was straight I had no interest in fooling around with another man, but then she asked me well what if this person looked so much like a woman that she would put a lot of real amd actual women to shame.

I laughed and told her that I don't think it would be possible for that to happen and jokingly said if you know anyone like that let me know and we'll take it from there, and the moment I finished my sentence she said that she did have a friend like that and asked me if I would be comfortable meeting her over drinks.

I was a bit taken aback by this but told her fuck it if it makes you happy go ahead and set it up but you better keep your expectations extremely low. Anyway fast forward two weeks later and I show up at the bar we're supposed to meet at and she's already there with her classmate Paola this hot Colombian classmate of hers I had the hots for, we had already met and spoken/flirted playfully a few times and we got along really well.

I asked Julie how come she was here with her since we were waiting for her other friend to arrive and Paola said she was gonna be leaving soon anyway, so I said fuck it ordered a drink and I sat down and we all started talking. After about 20 minutes I asked Julie if her friend was gonna arrive anytime soon and what happened next I'll never forget:

Julie looks at me with a devilish grin on her face and tells me that this friend of hers is already here, in the bar, and that she's just waiting for a sign from her to introduce herself. At this point I'm like in that case tell her to come over as soon as Paola leaves and we can get it over with, and that's when Julie looks over at Paola, who then looks me dead in the eyes and with an equally devilish grin on her face says “well honey, do I look like a woman enough for you?”

It didn't register in my mind at that moment what just happened and I replied “of course you do, what kind of stupid question is that?!” and then BAM!, the moment I finished my sentence is when reality hit me like a kick in the nuts and my reaction must've looked something like this:

Now at this point I was kind of freaking out, and I excused myself to go have a cig outside to gather my thoughts and try and make sense of this revelation, because I just had to wrap my head around what I just discovered. So it turns out that all this time Id had the hots for Paola, who I thought was a woman with her waist length black hair, big dsl lips and fake tits and small waist with wide hips that most biological women would kill for,, but was actually a man. I asked myself those this make me a fag? It can't though since I didn't know, I mean she looked like a woman after all, so I felt like I'd been tricked, deceived if you will, and I was feeling upset and confused.

But then I thought to myself, considering the amount of dicks that I'd seen having been a swinger, participated in numerous orgies/gangbangs over the years and fucked mens wives in front of them in cuckold scenarios and never once been remotely inclined to engage in any kind of sexual activity with a man, that I couldn't possibly be gay.

But the thought still kept nagging at me, and then out of the blue I felt a tap on my shoulder and turned around to see Julie standing there and she asked me if I was alright. I told her what was going on in my head, and that I was upset with her for revealing her friend to me in this way and she apologized and told me that she felt this would be a more subtle way of introducing her that would help to put me at ease.

I didn't quite get that logic but I told her to just go back inside and let me have another smoke and I'll come back inside afterwards, so off she goes and I start trying to figure out what my next move here is gonna be. I tell myself well I did find Paola attractive, very much so, before I knew she was actually a he, I knew from what Julie told me that she had the hots for me, and that she was willing to do whatever we wanted to her and be our sexual slave.

So now I start thinking more with my dick then my brain, and at some point Im like ok, I'll go back in, sit down and steer the convo in a more sexual direction and see how I feel about things and I'll go with the flow and see where the current takes me. So I finish my cig, head to the bar to order two shots of whiskey that I down immediately, then back to the table I go to join them.

To wrap the story up I decided to take the plunge and give it a shot, so we head to the hotel that was literally right next to the bar and rent a room. All I'll say about what took place in there is that Julie started off by unzipping my jeans and going to work on my dick and within a few minutes Paola joined in and the moment she went like this with my cock while slobbering/gagging all over it

Is the moment I realized I was ok with this and at that point I just said fuck it and went along with it, and I have no regrets whatsoever and it was a highly erotic and satisfying experience for all of us. And in case anyone is wondering, no I did not play, suck or touch her dick at any point, that simply does not interest me in the slightest but I did fuck her as is she were a woman and made her my bitch.

So, this experience made me realize that I'm obviously bisexual to a degree, and I've come to accept that fact and am quite comfortable with it at this point. I still have zero attraction to men, nada, but I can find myself attracted to t-girls that look extremely feminine and want nothing more than to get on their knees to suck and then bent over to get fucked.

And that's my story in a nutshell.
Too coincidental. Sounds like they ran game on you and turned you out. They'd teamed up and done it to other straight males before you, no question...

Hope you used protection...