From my extensive library of humiliating tranny chasing stories

From my extensive library of humiliating tranny chasing stories

>See tranny pornstar on FetLife (don't want to say her name because she lives in my neighborhood and is big enough to fuck me up)
>One of the offbrand ones, not a big name, in thirties
>Chat her up and arrange to meet up at this drag queen bar
>Get there and she's like 15% as hot as in porn
>Looks like Steve Buscemi in a blonde wig
>Need beer
>Standing at U-shaped bar talking to Steve, waiting for bartender to notice
>Look over to other side and this PAWG I used to fuck (with a vagina) is sitting there next to the guy who stole her from me
>They notice me and notice Steve
>They are both giggling
>Don't let them know that I've seen them
>Retrieve beers and retreat with Steve to a dark corner
>Discover Steve is not only Steve Buscemi but also has PTSD
>Get very drunk
>Evade PAWG all night
>Say goodbye to Steve when it isn't completely rude to do so
>Go home
>Look at Steve's FetLife profile again
>Says she's a lesbian
>The night I triple-cucked myself

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>post ad in m4t on Craigslist
>start chatting with latina qt
>she agrees to come over
>when she shows up she's all freaked out because some guy on the bus stalked her all the way to my apartment
>she's also extremely nervous
>has never fucked off the internet before
>after like twenty minutes we start making out finally
>fuck her
>cum fast but stay hard, her ass is phenomenal and way more womanly than most ts girls
>fuck her furiously
>dick mostly numb so last until I run out of energy
>dismount
>smell hits
>walk calmly to bathroom to discard condom
>little shit on condom, nothing that weird, throw in trash
>washing hands, notice smell again
>look down to see a halo of shit ringing from my belly button to my thighs
>"Hey I'm going to take a quick shower!"
>shower furiously
>go back into room and wrap it up politely
>after she leaves I notice my comforter has been visited by the shit fairy
>remove all bedding from bed, stow in corner
>few hours later, walking out of bedroom and I see a strange spot on the wall
>shit torpedo somehow made it all the way across room
>have to launch a thorough shithunt through entire room to ensure complete shit containment
>one of the reasons I don't fuck trannies anymore

>shit torpedo
fucking kek

>live in Las Vegas
>find OKCupid profile claiming to be Sarina Valentina
>I don't believe it's really her until she starts asking me to take her on luxury shopping trips at the casino malls
>tell her I'm broke and she bails
>flatter her back into the conversation and she gives me her phone number
>text for a while
>I have enough money to just barely cover lunch at this restaurant on the strip
>we make plans
>the day of, I take my good shirt to the dry cleaner's to dry clean the good shirt so that Sarina Valentina will fuck me based on the cleanliness of my shirt I guess
>text her
>she bails with some excuse
>maybe it wasn't actually her (it was)
>go to Craigslist dejected
>fuck a filipino tranny in an abandoned room at a nursing home instead

>chatting with tranny from Craigslist
>looks like if an exceptionally handsome Mexican day laborer had giant tits and nice hair
>I have trabajo for her
>she sends me an address to meet her at
>drive twenty minutes to a sketchy part of town in the middle of the night
>the address is in a strip mall
>she tells me to park in the parking lot so I park across the street instead
>text her and don't get a reply for like fifteen minutes
>finally she texts back
>"babby do u see party world"
>look into strip mall and notice there's a party supply store
>"Yes. Meet you out front?"
>"babby door open u come in ok"
>There are no lights on in Party World
>"You want me to come into Party World?"
>"yes bb come"
>Many minutes pass as I consider going into Party World
>She gets irritated at the delay
>"R U COME????"
>I am not going to enter Party World after all, reason wins the day
>I tell her this and she is furious
>I drive off into the night

why the fuck didn't you go to party world man didn't you read the sign

kek

>go to the big tranny bar in my city
>first time there
>wretched hive of scum and villainy
>half the crowd is tweaked out of their fucking minds, the other half are old crossdressers, and 1.3% are actually hot trannies
>talk to this one who looked like a fucking sex angel compared to the Jeffrey Tambors
>invite her out to my car for some reason
>extremely fucked the fuck up at this point in the night
>we sit in my car listening to Norwegian metal for a while
>the angelic halo has dissipated a bit
>I somehow did not notice inside that she is fat
>"Can I tell you something personal?" she asks
>"Yeah sure," I respond, expecting something about how she doesn't really trust guys or blah blah, whatever
>"I'm possessed by demons."
>Silence
>I look over and she's completely serious
>"I am possessed by the demon Beelzebub, who is the lord of flies" (delivered in the same offhanded tone you'd use to explain why you settled on a Ford instead of a Toyota)
>"Uh, I'm an atheist."
>"Oh that's cool. Totally cool, I'm cool with that."
>What the fuck man, head is spinning
>My head has transcended spacetime
>My head is in the astral plane
>"Hey do you want to go back inside?" I say.
>"Yeah sure cool totally."
>I give her the metal CD we were listening to as a gift before I split
>Least I could do considering the possession
>Cry in my car for like half an hour wondering what the fuck I'm doing with my life

>won't go to party world
>doesn't want to fuck a demonically possessed shemale
>doesn't want to fuck steve buscemi
>won't go shopping with sarina valentina
>can't appreciate a good ol fashioned shit halo

seriously op what the fuck is the matter with you

Someone needs to screencap this thread. Fucking gold.

If this becomes a screencap then at least I will have sucked all that dick for something

And you should keep sucking for more stories to come.

>meet a really, really hot tranny on OKCupid
>minor pornstar just then getting her name out
>again will not name because she could probably fuck me up
>she sends me pics of her getting fucked by Christian
>pick her up
>drive around awkwardly, unsure if I can just ask to fuck right away
>wind up at a city park, nighttime by then
>sitting on a bench and I make a move
>start blowing her for a second but she wants to move to somewhere that's less lit
>go into middle of a field where there aren't any street lights
>blowing her
>it's still only like 7:30 so there are a couple people way in the distance
>suddenly I freak out because someone shines a flashlight right at us
>look up, terrified expression, one hand still on her cock, to see a father ushering a child away
>mfw this nice dad took his kid out for an evening stroll and the sweep of his flashlight revealed a terrified man sucking off a he-woman in the darkness

>met up with same tranny many times afterwards
>one time I brought her back to my apartment
>we went into my bedroom to fuck and her purse was still in my living room
>got done fucking, got dressed and went into the living room getting ready to leave
>she checks her phone
>"hey do you know who Jim Norton is?"
>"Yeah, the comedian?"
>"Yeah, he followed me on Twitter"
>Jim Norton followed the tranny I was fucking while I was fucking her

hhahhahaaaa

you're trying to say u shagged Bailey jay?

Jim?

male jews suck the best cock

Really now? heh I'd love to fuck a hot tranny!

Your mental illness has some funny stories to tell

youtu.be/7oxqVC2rZHs

This
youtu.be/7oxqVC2rZHs

Mega-lol'd. Would read again

seriously they were bred to smoke pole
you could not last 1 minute with a male jew they have been trained since they were toddlers ny a rabbi how to please a man
hence the sterilize with spit rabbi's use

>one of the first trannies I ever met off the internet
>her pics made her look like a nine
>drove to a 7/11 to meet her
>she shows up looking nothing like pics
>looks like a straight up Star Trek villain
>her skin is stretched tight as FUCK for some reason
>dark skinned Asian but has bright purple contacts in
>her gaze pierces my soul as she gestures across the street towards her apartment complex with a gnarled ancient finger
>tell her I'll meet her over there
>get in my car
>warp factor eleven back home

>lesbian

steve could have skipped a few steps here

HAHAHAHA

>warp factor eleven

>chatting with qt on Grinder late at night
>looks really good
>quick layup, she's coming over
>messages ten minutes later saying she's here but can't find my place
>walk out and look up and down the block. Only a slightly hunched-over middle aged man walking while texting across the street
>oh no
>ohno
>Unfortunately she notices me before I can escape and walks over
>not exaggerating for story
>face of Edward James Olmos
>imagine EJO with two huge braids like a Mortal Kombat character
>now imagine an actual Mortal Kombat character
>paralyzed by politeness, I invite her in
>she looks extremely unimpressed by me
>immediately asks if she can fuck me bareback
>no
>gathers her things and leaves without comment
>I got catfished and then was too ugly for Shao Khan

Your penchant for banging the mentally ill is going to get you murdered one day :/

OP I love it.Live your life man.

Funny shit man

>late night on Grinder again
>message tranny who's only like 4,000 feet away
>pics look amazing
>invites me over
>drive like two minutes, park, and tell her I'm there
>a window opens and I see her waving me over
>she tells me to climb in through the open window
>get inside
>dirty living room with a futon in it
>talk for a second on the futon and she says she's going to the bathroom
>while she's in bathroom I take shoes off and then notice a lighter on the coffee table in front of the futon that is clearly for meth
>she comes back in and then makes fun of me for not being completely nude already
>about to ask her about the lighter when someone knocks on the window
>she looks over and says "oh that's just Chris, hold on"
>she pulls curtain aside to reveal an extra from Breaking Bad
>she deals him drugs
>"sorry about that," she says casually. "By the way, I'm a drug dealer."
>Am I going to fuck her still?
>Am I going to?
>No
>"Sorry, dealbreaker."
>She shows me the window
>Walk back to my car in the rain

I don't do it anymore

also most of them aren't mentally ill

Keep telling yourself that

you can't have standards if this is what you're doing

check this out: you can

OP here. I have many stories but I think those are all the funny ones. Hope you enjoyed.

Absolutely worth it, many spaghkeks were had.

great thread m8

thank you user

dude jesus christ

these are fun to read but most certainly these people as well as you are mentally ill. I don't personally care but it already takes a bit of being off to meet these strangers then factor in the whole tranny and other shady behavior whether in a closed party city or dealing drugs etc

tell us the hottest one~

yeah cool insight bro thanks

This one actually almost made the cut for being a funny story as well

>post ad to Craigslist
>tranny responds who had responded a couple times before but I hadn't pulled the trigger on because the pics looked off
>this time it was extremely obvious that I had fucked up before
>she looked like a model. absolutely stealth passable, zero masculine features, almost too good to be true
>we chat for a while and I come to believe she's real and we make plans
>I drive down to her neighborhood to meet her
>message her and she responds "omg u didnt tell me u were coming"
>says she has to babysit her younger brother
>annoying but whatever
>expect to only wait like an hour
>go to CVS to buy condoms, then go to McDonalds
>sitting at McDonalds languidly chewing a burger, waiting for her to be free
>hour passes
>message her, she's still babysitting, tells me soon
>another hour passes
>I sit at this McDonalds for at least three hours total, nervous wreck, wondering if I'm going to get fucking robbed by this person
>eventually get fed up and just drive to a nearby bar to try to pick up a woman who doesn't have a dick
>as soon as I get there, she finally messages back and is ready to meet
>she wants to rendezvous at a gas station
>park my car at this sketch ass gas station, tweakers scuttling about
>"this is how I fucking die," I think to myself
>she finally appears
>holy fuck
>she is somehow even hotter than her extremely hot photos
>would NEVER guess that she was trans
>gets in my car
>strained small talk
>drive to motel
>get a room
>cont'd

>She's about 5'6, half middle eastern
>Long, real brown hair, straight
>Very slender, curvy ass, small tits, really pretty face
>We get into the room and start making out on the bed, her on top
>We start getting undressed
>Even with her shirt off she looks like she was born a girl
>We're sitting up in bed and I reach down to grab her crotch
>Hand encounters a mound of flesh roughly the size of the Rancor
>WHAT
>Move hand around
>Feel an enormous cylinder of cockmeat tucked aaaaallll the way back to basically her asshole
>It comes out
>dude
>dude
>oh my god dude
>it's not like Mariana Cordoba level but it's giant, like 9-10" and thicker than a red bull can
>keep in mind she had not mentioned this whatsoever before the reveal
>she laid on the bed and I blew her for an unknown amount of time - time just kind of stopped
>the fantasy that you have about sucking cock when you've never done it and you're watching one of those especially hot webms
>that was what I lived
>my entire world was just that cock
>have networked with many many cocks before and since and that one was special
>we 69 for a while
>she flips over and I fuck her about six times in a row before she stops me because her ass is sore
>her ass is slightly lean but her profile is pure woman, just amazing
>I am fucking in love
>she wants to go home
>but I love you
>on the drive I tell her I hope to see her again
>she said I definitely would
>ghosted
>even though I don't fuck trannies anymore I would drop everything for another round with her

>why those have $0!!?

don't assume gender you POS

You drove there and got completely shitfaced?

OH SHIT, no, I got fucked up at a bar up the street from the tranny bar, where I met this weird swinger couple. The guy was this cornball 2005-era PUA who tried to give me wise sage pussy getting advice and the whole time I was just thinking like, "I have seen things you people wouldn't believe..."

hot

I sent her like four emails after she ghosted trying to persuade her to de-ghost me. It was that life altering

has anyone screencapped this