Date: Fri, 03 Mar 2023 12:44:22 -0600
From: Timi Darlington <sweett53@zohomail.com>
Subject: The Railroad Crossing

Tranny Tales
Stories of an amateur cross-dresser's fantasies and true adventures

The Railroad Crossing

I scheduled a week long seminar series connected with my business that
brought me to a large city in Texas.  So, I had a wonderful opportunity to
try out various outfits from my girlie wardrobe collection, sample the
local gay scene and maybe enjoy a man or two!  Although flying would be a
chore, the distance justified a plane and renting a car. And, for a little
extra cash I could rent a candy apple red Mustang convertible!  A dream of
mine has always been to dress up and cruise with the top down!  Yes, it was
on my bucket list, something to do before I retired from cross-dressing! It
was early spring and the weather was warm but comfortable.  So, I brought
various blouses and skirts that I didn't have a chance to wear during the
winter.

I booked a room at an inexpensive easy -in, easy-out motel some distance
from the downtown convention center where the seminar would be held.  But,
it was very convenient for dressing up and visiting the local bars and sex
shops.  The motel was just off the highway that went downtown and
paralleled a railroad track. In order to reach my motel, I had to turn off
the highway and cross the track.  The railroad crossing was under repair
that resulted in lane closures and was further complicated by a traffic
light that took forever to change!  So, each morning and late afternoon I
would depart to and return from downtown in my red Mustang as a typical,
rather boring looking business-man.  But, later that evening I would leave
and return as a rather attractive and seemingly very female brunette.  Of
course, I had to have the top down so that other drivers, especially truck
drivers, would have a nice unobstructed view of my legs under a very short
skirt!

I soon realized that others were enjoying the view, including the railroad
workers repairing the crossing.  Apparently, there weren't too many blazing
red Mustang convertibles driven by a hot "girl" in that part of town!  Two
men in particular seemed to take more and more interest in my daily
departure and return as a male and another departure again in the early
evening as a female.  One, was a giant with long reddish hair and a long
scruffy beard.  He was perpetually smiling at me.  The second man was much
more serious.  He preferred giving me that "I'm going to fuck you!" look.
He wasn't quite as big but very muscular, well-groomed and with a dark
handle-bar moustache.  I quickly gave them both nicknames; Big Red and
Moustache! They appeared to be supervisors with hard hats, phones and
clip-boards as they inspected the workers during the day and inspected me
each evening!  The traffic light and heavy traffic gave them plenty of time
to inspect!  At first, they watched me in silence and I tried to avoid
their stares.  But, as the week progressed, I started hearing whistles, cat
calls and "other" compliments. Being a bit of a cock tease, I found myself
looking back at them and smiling, but only when I was dressed up.  I
started to look forward to each day hoping I would see Big Red and
Moustache.  My spirits would lift if I saw them during the day and sink if
I didn't.  I reasoned that they had inspection work elsewhere and I would
only see them sporadically if at all!  But they were always present on my
evening excursions when I was dressed in something very sexy.



I was having lots of fun dressing up and getting out and each evening with
something different to wear! The local sex shops and bars contained plenty
of men.  Some were nice looking and interesting and some interested in me.
But, I couldn't get my mind off of Big Red and Moustache.  By the fourth
day, my seminar was winding down and the railroad crossing work had moved
over to the other side of the street.  In another day I would be going home
and their work would be winding up. I realized that I wouldn't be seeing
them anymore which made me want them even more! Oh, I wanted to give myself
to them, both of them!  Yes, I wanted to be taken by them at the same time!
It had been some time since two men had me for sex and no two men would
likely compare with these two ultra-alpha males!  Oh, but how?  I knew they
were interested by the way they looked at me.  But, I wasn't sure if they
were just having some fun with me or if they really wanted me!  There would
only be one more night to find out!

I returned from the seminar early that day seeing them once again at the
crossing.  I gave them a smile and a wave.  Big Red nodded but there was no
response from Moustache.  Of course, I wasn't dressed up yet. But, I soon
would be and looking as beautiful and alluring as possible.  I cleansed and
lubed thoroughly hoping that my pussy would find some dick that night!  I
then trimmed and shaved what body hair I could, rubbing my smooth body with
a soft, sweet smelling lotion.  I put on a garter belt under my black
corset, applied my make-up, put on my favorite, long and thick black wig
and then my pink bra, matching panties and scarf.  After attaching my thigh
top fish nets to the garters, I selected a tightly tailored light blue
blouse that matched my eyes very nicely.  For a skirt, I opted for my
prettiest print skirt that was very short and complemented both blue and
pink. I added my usual accessories including pretty earrings, bracelets and
a belt that cinched me tightly at the waist.  I'm not one to be overly
vain.  But, I had to admit I looked gorgeous and sexy in the mirror and
knew I would be irresistible. After a little powder touch up and some sexy
perfume I grabbed my purse and proceeded to my chariot, my lovely red
rented Mustang convertible.

My heart was pounding as I quickly reached the railroad crossing.  The
traffic seemed heavy and the traffic light seemed even slower than usual.
I would be waiting for several minutes before I could make it to the
highway leaving plenty of time for Big Red and Moustache to see me.  At
first I didn't see them and my heart skipped a beat.  Were they already
gone?  But, as I approached the intersection, I saw them emerge from their
trucks and approach the street, approach me, almost close enough to get
into my car!  Maybe they were on the lookout for me!  They acted like they
didn't even notice me at first until Big Red let out a whistle and grabbed
his crotch.  Moustache, always serious, lowered his sun glasses so that I
could see his eyes and his intensity. Yes, I had their attention!  But,
where would we meet?  As I inched along in the traffic, ideas on where to
meet passed through my mind and evaporated.  Suddenly, I couldn't think of
a single place!  Then, as the light turned green and I had to turn, I said
"Pickles"!  It was a local beer dive that wasn't too far away. As I turned,
I couldn't tell whether they heard me or not or if they even wanted to
pursue me.  Just like that, a fleeting moment, my chances of getting laid
by two men hinged on one word probably lost in the traffic noise.

As I pondered this, I drove on to my usual bar and sex shop locations
enjoying the local clientele one last time.  One cowboy type came on to me
and I was tempted to give him my motel room number for a midnight "rodeo".
But, I was holding out for my two studs that I hoped might meet me.  The
evening was wearing on and I already had more than a few beers.  All I
could think about was "Pickles".  So, I decided that I would finish the
evening there with or without two nice cocks to service!  The bar was near
my motel and I passed the railroad crossing which was now very quiet and
dark except for the blinking detour lights.  My men had probably gone home
to their wives or girlfriends.  So, I hoped Pickles had a rugged cowboy or
two!

Pickles was one of my favorite stops and I was becoming a regular and
welcomed as a tranny.  It was aptly named as it was mostly men mixed with a
few lesbian couples and what appeared to be a straight couple or two.  I
parked in back and walked around to a side entrance as I had done before.
But, when I came through the door, several of the regulars turned around
and gawked at me and whistled as the bar tender brought me my beer of
choice, looked me all over and asked "Are you on a man hunt tonight,
gorgeous?"  I nodded, feeling myself blush and several men chuckled.  But,
I hardly noticed as I proceeded to the restroom.  After having a few beers
already from my first stops, it was time to "give some back".  Once done, I
checked my make-up in the one grimy mirror provided and took a seat at the
bar where I found not one beer but two!  I inquired about the second beer
with the bar tender who just shrugged his shoulders. Maybe I had a secret
admirer and hoped he would declare himself!

Now, I'm not a heavy drinker.  But, I can handle beer without getting too
tipsy.  But, my bladder is entirely another matter! Too much beer
automatically results in too many trips to the john and I could already
feel the urge to pee again!  As I fought the urge, I casually surveyed the
crowd hoping one or both of "my" men would show.  I realized that thinking
of them as "my" men meant that I already had expectations that could only
be satisfied with a man, any man, tonight!  Some looked promising.  But
each seemed to be paired up with another man, one of the few single and
"real" women, or were waited for friends to arrive.  Oh, it might turn out
to be a lonely night for me.  But, at least I had my dildos to enjoy as I
fantasized about two handsome hunks!

I was well into the second beer when I succumbed to the need to pee and
returned to the restroom.  As often happens, once I start drinking beer and
pee that first time, it seems I can't stop for the rest of the night! I
tidied up, checked my make-up once more and returned to my seat finding not
one but two more beers!  I protested to the bar tender who motioned toward
the door and there they were; Big Red and Moustache who promptly raised
their beers!  I must have turned three shades of red and my heart was
pounding!  Yes!  They were here!  I felt a certain tingling in my panties
and my nipples perk up as they walked over to me and stood right up against
me with Big Red on my right and Moustache on my left.  I stood up to greet
them and touched their beer bottles with mine.  I knew it was going to
happen, I was going to have sex with "my" men and I could feel my pussy
pucker with anticipation.  I was confident, maybe a little giddy and
totally willing.

We sipped our beers, exchanged names (Big Red's name was Sean and
Moustache's name was Richard) and engaged in small talk consisting of where
we lived, work, families etc.  But, they weren't there for small talk as
they pressed against me with roaming hands that discreetly caressed my legs
and squeezed my ass.  Inevitably, questions as to what I liked "to do" for
a man and where I liked to "do it" came up.  They really didn't need to
hear what I liked doing for a man, not the way I was dressed!  I offered up
my motel room for our "party".  Instead, Richard said he knew of a place
where we would "really" be alone.  It was obvious that they had a plan all
worked out knowing I would come.  After another round, my bladder was about
to explode.  So, we agreed to meet outside after I made another trip to the
restroom and they paid the tab.  I took extra time to check my make-up and
freshened my lipstick.  My hands were shaking as I contemplated leaving
with these men!  I knew each was man enough.  But, was I "woman" enough to
take what they were going to give me?

We met out front and Richard instructed me to follow Sean with Richard
right behind me.  We left the bar turning left onto the highway following
the railroad track for a few miles with Richard on my tail, closely on my
tail.  The evening was cool and comfortable and I loved feeling the breeze
flowing through my long wig as we sped down the highway!  Then, Sean slowed
and made a sudden right turn on to a county road and then a quick left turn
on a seldom used road that closely followed the track. It must have been
used for track maintenance.  The ruts and holes were deep as we bounced
along the road and it wasn't helping my bladder!  Yes, with all the beer I
already needed to pee again!  We finally stopped at an open, graveled area
between two small shacks that must have been used for maintenance equipment
and were dimly lit by security lights. In between were stacks or railroad
ties, rail and old railroad crossing equipment.  Sean pulled off to the
right.  I pulled up next to him and on his left while Richard parked behind
me. Now I was trapped by their trucks, a shack to my left and a deep ditch
in front of me with no means of escape, at least by car!

It was obvious that we really would be alone!  But, I never felt afraid or
threatened by either of them.  If anything, I was perfectly calm and ready
to "play"!  But, first, I had to answer nature's call!  I emerged from my
car as Sean and Richard emerged from their trucks.  As they approached me,
Richard said "Ready to play sweetheart?"  "Yes," I responded.  "But, I need
to take care of a little business".  "Oh, does sweetie need to pee again?"
Sean asked.  "As a matter of fact, I do."  I said, smiling as I looking for
a little privacy.  "We want to watch you pee." said Richard.  "You've never
seen a girl pee before?" I asked.  They chuckled as I hiked my skirt up,
pulled my panties down and squatted to pee facing them with the driver's
side car door supporting me from behind. From their vantage point, they
couldn't see my little penis.  So, I guess I really did look like a real
woman urinating.  What they could see was a small stream of urine flowing
between my heels before soaking into the gravel.  While they watched me, I
watched them playing with themselves, unzipping their jeans and pulling out
their dicks, stroking, pulling and seeming to be teasing me, the way men
can do!

Finally, the flow stopped.  But, before I could even stand to pull my
panties up and my skirt down, their dicks were in my face, each competing
with the other for the soft, wet warmth of my mouth.  "Suck it!" Richard
said. Sean joined in with "Let's see those pretty lips wrapped around some
dick."  It was hard to choose which one to suck first as both men caressed
my face with their dicks. I honestly don't remember which one I started
with as I sucked and licked each one repeatedly, enjoying the soft,
marshmallow heads on my lips and tongue.  In no time at all, each dick got
progressively thicker, longer and harder.  I progressed to deep throating
each one enjoying the size and girth.  Back and forth, I sucked each so
eagerly, maybe too eagerly!  They were both at least 7-inches and very
thick at the base and so ready to cum!

Suddenly, Richard grabbed my head forcing his dick deeper down my throat.
He held my head firmly against the car door behind me.  I had no option
other than to take it, take it all as he face fucked me.  He started
moaning and backed away letting Sean take his turn with me.  It was all I
could do to manage my breathing trying to time a breath with each stroke
and choking in the process.  They took turns allowing me to enjoy their
luscious man meat, the soft, silky smooth shafts, sliding through my lips,
ending in a forest of course pubic hair.  Their manly, musky aroma turned
me on and I moaned with delight loving this moment, these two men and their
two dicks.  "Mmmm, she likes it nice and rough doesn't she", Richard asked.
Sean replied with "Let's try her ass-pussy!"  "Yeah, let's get some of that
tranny cunt! You go first!" Richard said.

With that, Sean grabbed me under my shoulders and physically lifted me up
and carried me to the back of my car placing me on top of the trunk.  The
trunk sloped downwards and while it partially supported me, it allowed me
to slide down toward him.  While his body pinned me against the trunk, he
reached for my panties pulling them off and then spread my legs with his
massive frame between them.  He next unbuttoned my blouse and lifted my
38-C bra up grabbing my real, 38-A breasts squeezing them hard while he
kissed me, kissed me very hard.  I could feel his dick against my tummy as
he spit in his left hand and lubed my sphincter sticking one then two
fingers into me, pushing, grinding and hurting.  But, I was too excited for
what would surely enter me next to even think of complaining.  I moaned
softly as he continued to kiss me before lifting my legs up over his
shoulders spanking me hard.  I could feel my ass turn a nice warm pink!

He grabbed me again at my waist while his dick stroked the entrance to my
pussy before he entered me, slowly at first and then with one hard thrust
he was deep into me.  I felt pain and screamed as he thrust again and again
deeper into me.  I was trapped and helpless! As I slid off the trunk I was
pushed back up by his dick deep inside me with his strong arms holding me.
My screaming subsided into moaning as he fucked me, totally oblivious to
any pain or discomfort I might be enduring. I don't know how long he fucked
me.  But, the longer it went, the more I was enjoying it, feeling it slide
in and out of my tranny pussy! I was in another world, a sweet world that a
real woman might know, a world of pleasure and delight by being totally
taken by a man.  Finally, with one strong thrust, Sean let out a scream,
more like a roar as his cum spewed into the deepest recesses of my pussy.
He was finished.  He let me go allowing me to slide off the trunk and onto
the gravel.

While Sean was fucking me, Richard watched for bit and then went to his
truck.  I thought he was giving us some privacy.  But, in reality, he was
getting ready for his turn with me.  He returned at some point to watch
Sean finish.  He then came over and grabbed me by my left wrist and pulled
me over to the back of his truck.  The tail gate was down with some old
carpet draped over the end.  While standing, he told me to turn facing his
truck and bend over the tail gate.  With one of his knees he shoved my legs
apart. "This is how we fuck naughty girls back home!" he whispered in my
ear before biting me on the neck just below my scarf.  Not expecting to be
bitten, I screamed and was quickly silenced by a loud "shush" as he spanked
my ass hard.

While Sean was rough, I sensed Richard was going to be even rougher and I
was right.  He spanked me repeatedly as I screamed into the night realizing
why they took me to this deserted place where my screams would not be
heard. "If you can't shut up, we'll shut you up!" Richard yelled. "Sean,
get her panties!" Sean retrieved them from where he had thrown them.
Richard forced them into my mouth, undid my scarf and tied it around my
mouth to retain the panties.  He then took some rope, tied my hands
securely and stretched them out above my head and secured the other end of
the rope to a tie-down bracket somewhere in front of me.  I was now totally
at his mercy, their mercy as I wiggled and moaned to their obvious delight.
They could do what they wanted for as long as they wished.  And they
did....

Then Richard knelt behind me and licked my pussy.  Oh, I loved that and it
seemed to calm me down! But, then he bit me repeatedly while rimming me.
He seemed to be teasing me with pleasure then pain.  I was struggling with
how to differentiate between the two as he mounted me.  My pussy was
already well lubricated with Sean's cum and ready for Richard's entry.  He
had no difficulty penetrating me!  He wasn't as big as Sean but big enough
and thicker as he rammed it into me.  The carpet offered very little
cushioning against the hard, dirty surface of the tailgate and my pelvis
ached with each thrust.  He fucked like he was a machine with no desire to
reach orgasm.  Perhaps his real pleasure was watching me wiggle, squirm and
moan.  My only relief came when a train passed through.  A blanket was
thrown over me and Richard and Sean hid in their trucks.  The train crew
would see nothing unusual as they sped by.  As it disappeared, Richard was
on me again with renewed strength and intensity.  But, finally, he exploded
with a loud orgasm, and as he did, he grabbed both of my breasts and
squeezed them as hard as he could.  He stayed deep inside me, still pumping
me, mixing his cum with Sean's!  Tears welled up in my eyes as I continued
to squirm and moan. Finally, he stopped.

But, they weren't done!  Sean was once again aroused, apparently while
watching Richard fuck and spank me.  They each took another turn at me
while smoking and drinking beer.  Another train presented another
opportunity for me to rest.  By then I had finally stopped squirming and
moaning.  I was totally spent and at last, they were too.  Richard released
me and offered me a cigarette and a beer.  I declined the cig but grabbed
the beer and guzzled it right down not realizing how thirsty I was.  While
I slipped my panties on, straightened my bra, buttoned my blouse and
smoothed my skirt, they asked me if I liked it.  Did I like it?  I was
essentially raped by two very big and strong men.  My breasts ached from
being squeezed and surely they were badly bruised.  I wasn't even aware
until then that my wrists were cut in places where the rope had dug into
them. My pelvis ached and was likely bruised.  My sweet tranny pussy was
bruised and swollen from big rough fingers and large dicks. I couldn't walk
quite yet and I just leaned against the pick-up.  Did I like it?  Mmmmm,
Yes, I loved it!

I don't even remember driving back to my motel and awoke the next morning
to shower.  Yes, there were bruises and cuts.  But, oh, what a sweet memory
I have!  Now, railroad crossings always bring a smile!



Greetings all!

While my tranny name is Tricia Louise i go by Timi these days.  If You got
this far, i hope you enjoyed my story.  While i'm a little more into
"retirement" these days, i still enjoy "femming up" a little and visiting
friends, bars and sex shops occasionally.

Sweett53@zohomail.com

I'm married.  But, I have a nice Daddy friends who enjoy my services.  I do
enjoy corresponding with Men who appreciate us along with other like-minded
"demigirls".  You'll find me very responsive, caring, and friendly.  I love
swapping photos and stories and enjoy writing about my adventures,
thoughts, feelings and fantasies.

Please be safe!

Love,

Tricia/Timi