My First Night Out
story by Otter
I started cross-dressing in private with my older sister’s clothes when
I was about twelve years old. As a teenager I found I could pass as a woman if
I took the time to dress and apply my make up properly. I also found I could buy
beer and liquor dressed as a woman without ID and even passed myself as a substitute
teacher on at least three occasions, going to school on Halloween dressed as a
woman. I was even reprimanded by the principal once because my skirt was shorter
that what he deemed appropriate for a teacher. As a young man I kept my cross-dressing
to myself, and even purged my wardrobe a few times.
When I was in my early
twenties, my favorite radio station had a Halloween costume ball at one of the
cities’ better hotels. I wore suntan pantyhose, a lace up corset, black five-inch
sandals with straps that wrapped around the ankles and buckled together. I wore
a black bra with foam inserts, a long sleeved turtleneck sweater dress that came
about eight inches above the knee. I had a gold anklet on my left ankle, a small
gold watch, clamp on earrings that hung three inches below my earlobes, and a
light brown wig about eight inches below the shoulder. My friend’s wife applied
some acrylic fingernails and make up, and tweezed my eyebrows. I looked perfect.
I arrived at the costume party and signed in, someone even commented that
I was supposed to be in costume, I was thrilled that I could still look that good.
I sat at the bar drinking Pepsi and noticed a couple of guys checking me out,
one guy paid very close attention to my legs as I sat on the stool with my legs
crossed and my dress almost up to my crotch. He came to sit next to me and we
talked, he bought me a drink and carefully moved closer to me every time he got
the chance. Then he kissed me, the look on my face must have tipped him off, “What’s
the matter? You looked surprised.” “I am!” I replied. “I wasn’t
expecting that!” “I’m sorry, I couldn’t resist.” He told
me, and leaned in and kissed me again. Almost involuntarily my lips parted and
let his tongue touch mine. He had his hand on my right thigh and as we kissed
he slid his hand up the inside of my thigh under my dress. We shared a long passionate
kiss and I pulled back thinking that it wasn’t as repulsive as I had imagined
it would be. He thinks I’m a woman. I’ve always been straight and found
kissing this guy somewhat unique.
I wasn’t willing to let this progress
much further, but found myself kissing him again. Each kiss becoming more passionate
than the last, he slid his hand up under my dress all the way to the cotton crotch
of my pantyhose, I had my dick tucked under my ass and it was straining to be
released, if he felt it he didn’t react. We kissed again and I told him I
had to leave. I was starting to get turned on and I didn’t want to go any
further. He backed off and said, “I’m sorry! I’m moving too fast,
right?” “No! It’s not that!” I told him. “I’m just
not ready for this!” “Can I walk you out?” He asked me. “I’m
staying at the hotel.” I lied. “I have a room too!” He told me.
I got off my stool and felt a little lightheaded, I’d been drinking Pepsi
and I shouldn’t feel like this. I opened my pocket book and tried to focus
on my wallet. My newfound friend dropped a twenty on the bar and said, “I’ve
got this, let me help you, sweetheart.” I looked at the bartender, wondering
what was making me feel lightheaded. I got no reaction from him. I swayed a little
as I stood in my heels and the man I’d been kissing took a firm grip on my
arm. He led me to the elevator and we waited for it to arrive.
We boarded
the elevator and he punched a button, I could walk well enough, but something
wasn’t right and I asked him what he’d given me. “You probably
had too much to drink.” He told me. We got off the elevator and he steered
me down the hall, we arrived at a room and he pulled out his key card and slipped
it into the lock. The lock clicked and he pushed the door open. When we walked
into the room I noticed three other guys sitting in the room watching television.
He steered me to the bed and told me, “Sit and relax, you’ll feel better.”
Taking my pocket book and dropping it on the table. I sat on the bed and he pushed
me back and started to kiss me again. “I need to get going!” I told
him. “Sure, sweetheart, just relax for a minute.” He told me and we
kissed. I noticed the other three guys were watching us and I tried to get up.
He pushed me back and continued kissing me. “Relax! We just want to have
a little fun!” “Forget it!” I told him and tried to get up, looking
at my purse on the table. “I need to leave.” “You’re not going
anywhere until you suck us off!” I was told. I tried to get up and the others
came and grabbed me by my arms. My wrists were lashed together behind my back
with a piece of cord and the guy from the bar pulled off his trousers and underwear,
exposing his hard on. He pressed himself against me and kissed me and I tried
to resist. I could feel his dick against me and he pushed me down onto the bed.
He was laying on me, kissing me, and I couldn’t move.
The others were
pulling off their clothes and he pushed his dick into my mouth, forcing it down
my throat. I started to gag, then swallow, trying not to puke. I was pulled up
to sit on the side of the bed and they took turns shoving their cocks into my
mouth and I sucked them dry and swallowed their cum. I figured it would be safer
for me to do what they wanted until I could get away. I sucked all four of them,
and was hoping I could go soon.
“I want to fuck her!” One of
them said, and he stuck his hand under my dress to tear out the crotch of my pantyhose,
pushing me back. Another one grabbed an ankle and was kissing the inside of my
leg. Then both of my ankles were being held up, that’s when the one who said
he wanted to fuck me tore out the crotch of my pantyhose and found my dick. “You
picked up a faggot!” “What?” The guy from the bar asked. “She’s
got a dick!” I was rolled onto my stomach, “Get on your knees, bitch!”
I got my legs under me and was kneeling on the bed with my wrists bound behind
my back and they took turns fucking me in the ass. I tried to clinch my ass and
resist, someone pushed a finger into me and then a cock. They forced it into me
dry and it hurt like hell. They weren’t gentle, taking turns on me, fucking
me in the ass and filling my ass with cum. I lost count how many times they fucked
me, each time taking longer and longer to cum. After they were done with me they
decided to leave, one asked the others what to do with me. The guy from the bar
said, “What’s he going to do? Call the police? You’re not going
to call the police are you faggot?” “No.” I mumbled, with my face
buried in the pillow. “You’re going to go away and forget this ever
happened, aren’t you?” He asked. “Yes, I’ll go away.”
“Tie his ankles together so he doesn’t go anywhere, housekeeping will
find him in the morning. Is that okay, Sweetheart?” “Yes, Thank you.”
I said. They left me, with my wrists and ankles tied behind my back, I felt wet
and didn’t know if it was blood or cum I could feel dripping from my ass.
“We’ll be seeing you, sweetheart.” The one from the bar said as
they walked out. “Count on it!” I replied.
I was lying on the
bed in the hotel room, with my ankles and wrists tied behind my back. I even managed
to get some sleep. I had plenty of time to think about what had happened and what
I planned to do about it. I knew I’d be able to find out who rented the room,
I’d find out everything I needed to know, this wasn’t over, not by a
long shot. I heard a knock on the door and a voice announced, “Housekeeping.”
I waited for the door to open, I knew if I said anything she’d leave. I heard
the lock click and the door opened slightly, "Housekeeping.” I waited
for her to come in. “Untie me, Please.” “Oh my god! What happened
to you?” The maid asked. “I was attacked last night during the Halloween
party. Please untie me.” I pleaded. “I’m going to call the police!”
The Maid said. “No! I don’t need the police, I need to be untied!”
The maid fumbled with the rope, trying to untie it and not succeeding. “I
need to call for help! You just lay still!” She told me. Like I had a choice.
“There’s a knife in my purse, is my purse still on the table?”
I asked. I could hear the maid rummaging through my purse. Then I heard the click
as she opened the blade of my pocketknife. A moment later she touched the blade
to the rope and my legs and arms were released.
I hurt. I hurt, bad. My
shoulders, hips, knees, ass, back, I’d lost track of time, I must have been
tied for eight or ten hours. I had to piss. I lay there thinking, as the feeling
slowly came back to my legs and arms and I hurt even more. I rolled off the bed
and tried to stand up, and fell because my feet were still numb. I sat on the
bed and unbuckled my sandals, or tried to, my fingers were still numb too. The
maid helped me get the sandals off and got me on my feet. I headed for the bathroom,
she helped me, and I pulled my pantyhose down and sat on the toilet and pissed
about a quart. “I need to call the police!” The maid said. “You
poor thing, how long were you tied up like that?” “About ten hours,
just a little less than eternity.” I told her. “I don’t need the
police.”
I stood up and straightened my dress. Then I looked at the
maid, she was pretty, and I kissed her. “Thank you!” I kissed her again.
“What happened?” She asked. I gave her the Reader’s Digest version
of the events while I washed up and checked for damage. Re-applied my lipstick,
and checked my purse. I still had everything, the assholes never went in my purse.
I carried a spare pair of pantyhose and changed into them, put on my sandals and
checked the mirror. I still looked good, with a baby face, and light hair, I didn’t
even appear to need a shave. “Is there anything I can do?” She asked.
“Give me your name and telephone number, and keep this to yourself.”
I told her.
I went home, took a long shower, and started plotting my revenge.
In the next two days I found out everything I needed to know about the four guys
who raped me. Their names, where they were from, I got it all. They were mechanical
contractors, working on an installation here for a couple of weeks. They were
staying at the hotel sharing two rooms. I went shopping, work allows me some freedom
to travel, and I bought what I needed while I was on the road over two hundred
miles from home. I visited a hardware store, sporting goods store, gunsmith, wig
shop, I bought a nice light blue blouse, dark blue skirt and jacket suit, a pair
of black leather pumps with five inch heels and detachable ankle straps. I wanted
to look good, like a businesswoman, not slutty.
Friday night I went to
the hotel and sat in the bar, I was wearing suntan pantyhose, black pumps, light
blue blouse, and dark blue suit with the skirt well above the knee, and a peach
scarf. My wig was about eight inches below the shoulder in dirty blond, gold anklet,
gold watch and gold earrings. I looked good. They were sitting in the hotel bar,
drinking, all four of them. I was sitting at the bar, drinking Pepsi, my skirt
was almost up to my crotch and I had my legs crossed. I watched them for awhile
and the one who had picked me up on Halloween seemed to be checking me out. He
came to the bar and took the stool next to me, moving it closer as he sat. He
ordered a drink and asked if I wanted one. “I’ve had enough.” I
told him. “I’m a bit tipsy now.” He moved closer and we made small
talk, I giggled at the things that were supposed to be funny and he had his left
hand on my leg. I touched him from time to time and his hand moved up my leg a
little at a time. I kissed his check a couple of times and he turned into one
of my kisses and our lips met. I kissed him passionately and he didn’t have
a clue we’d met a week earlier.
He told me his name was Dave, which
I knew was a lie. “Do you have a room here, Dave?” I asked him. “Yes,
I’m staying here for a couple of days.” He told me. “You want to
go back to your room?” I asked. He signaled his co-workers when he thought
I wouldn’t notice, then paid our checks. His friends got up and paid, and
headed for the elevator. I stood and leaned on him like I’d had too much
to drink. I kissed him again, we went to the elevator and his friends were on
their way up. Dave pressed the up button and we stood there kissing until the
door opened. When we entered the elevator I kissed him again and he pushed me
up against the wall. He ground his hard on against me and I lifted my left leg,
wrapping it around him while he pulled my thigh up and ground his dick into my
crotch. I gave his ass a squeeze and sucked his tongue into my mouth.
He
steered me down the hall to his room and inserted his key card, the lock clicked
and we went in. His co-workers were sitting in the living room watching television.
“Can I use the bathroom, please?” I asked. Dave pointed at the bathroom
and I went in, closed and locked the door. I pulled off my press on fingernails
and put them in a baggie. I put on my latex gloves, pulled my compact Glock out
from the back of my skirt, and screwed on the suppressor. I pulled down my skirt
and pantyhose and sat for a quick piss, when I was done I took off my jacket and
draped it over my right hand to hide the Glock. I unlocked the door and opened
it an inch to listen.
Dave was telling his friends that I was drunk and
he didn’t need to put anything in my drink. “What are you doing in there?”
He asked. “I had to pee, and take off my fingernails.” I said as I opened
the bathroom door. I walked out with another button on my blouse open showing
some of my bra. “You didn’t tell me you were going to share me with
your friends. Who wants to be first?” I asked. Larry, Curly, and Moe all
raised their hands. I moved away from Dave and said, “Get undressed.”
Dave unbuckled his belt and lowered his trousers and underwear and sat on the
bed. I swung my jacket away from the Glock and started double tapping from left
to right. Double tap to the heart on all three of the stooges, then I turned toward
Dave. He was staring at me in shock. I single tapped each of the three stooges
in the head, then went to Dave. I dropped the empty magazine and slammed in the
full one. I had fired nine rounds from a ten round magazine, now there were eleven
rounds in the pistol. “What are you going to do?” He asked. “I
just double tapped each of your co-workers in the heart, then single tapped them
in the head, what the fuck do you think I’m going to do?” “You’re
going to kill me?” Dave asked. “Yes, I’m going to kill you!”
I told him. “Why?” “You don’t remember last week? Halloween?
You brought me up here and made me suck all of you off? Then you took turns fucking
me in the ass?”
“You’re the faggot I picked up?” Dave
asked. I cracked him across the bridge of his nose with the Glock. “I’m
not a ‘faggot,’ I was at a Halloween party dressed as a woman, you drugged
me and tied my hands behind my back and shoved your cock in my mouth, and shoved
it up my ass. I don’t seem to recall having a choice in the matter!”
“I’m sorry!” Dave said. “I’ll bet you are! Get on your
knees! Face the headboard!” Dave did as he was told, he knew he was going
to die and I didn’t want to take any chances. I couldn’t give him an
opportunity to make a grab for me, or the gun. “Put your hands behind your
back!” I put a heavy-duty tie wrap around his wrists, then pushed him down
on his stomach. I took some nylon cord and bound his wrists together. “On
your knees!” Dave got his knees under him, kneeling, facing away from me,
with his face on the pillow. I pulled the pipe bomb out of my purse and started
to shove it up his ass, dry. He cried like a pig and I picked up his underwear
and stuffed them into his mouth. I didn’t bring anything to lube the pipe
bomb, KY lubricant, Quaker State, anything would work. I gave it a twist and shoved
it into him, making sure it was all the way in and his asshole closed around the
fuse. I policed my brass, counting every piece, checked the hallway, I tossed
an earring on the floor, and tossed the back of it near the door. The kind of
earring for pierced ears, not clamp-ons like I was wearing. Then I planted some
long blond hairs. I removed the suppressor from my Glock and put it in the baggie
with my fingernails and spent casings. I double-checked everything. Then I pulled
his underwear out of his mouth. “When that fuse burns down to your asshole
it’s going to hurt.” I told him. “For how long?” Dave asked.
“For the rest of your life! Moron!”
“One thing, before
you light the fuse?” Dave asked. “What?” “Kiss me, Please?”
“Are you out of your fucking mind?” I asked. “Please?” He
whimpered. “You’re so hot! Please?” I couldn’t believe this,
I was about to blow his ass off, literately, and he wanted me to kiss him. I could
understand him kissing me when he thought I was a woman. Now his last wish is
to have the guy who’s going to explode a pipe bomb in his ass kiss him. I
twisted him around and turned his head toward me. I laid on the bed next to him
and let him rub his dick against my leg, I kissed him, like I really meant it,
passionately. I reached down and took his dick in my latex gloved hand, it was
rock hard and I stroked him a few seconds. He smiled and I figured “What
the hell! Who’s going to know?” I turned around and pressed my leg against
his face, he kissed my thigh, trying to get his face under my skirt. I took his
cock in my mouth and sucked him in. Stroking him and sucking his shaft. It only
took a minute for him to cum, I swallowed it, pumping him dry, being careful not
to let a drop escape, I didn’t want a drop of his cum on my face or clothes.
He was rubbing his face against my crotch and I could feel my dick starting to
get hard. I turned around and kissed him again, deeply, passionately. I got off
the bed and he looked at me and said, “I love you!” “You’ll
get over it!” I told him. I stuffed his underwear back in his mouth. I lashed
his ankles together and ran the cord around the lashing at his wrists, then pulled
his ankles up and bound them to his wrists like they had done to me. I checked
the hall again, then wrapped the fuse around his cock and balls and lit the fuse.
I kissed his cheek and walked out leaving the “Do not disturb” sign
on the outside door handle. I walked down the carpeted hall silently, stripping
off my latex gloves, straightening my skirt, and tucked my Glock in the back of
my skirt, wondering why I had bothered to suck his dick.
When I got home
I went into the garage and stripped the Glock, I lit the acetylene torch and burned
the barrel into six pieces, cooled them in the sink and dropped them into the
baggie with the fingernails and spent casings. I went in the house and stripped
out of my suit and showered in my pantyhose. Stripping them off in the shower.
As I dried off from my shower the telephone rang, I looked at it and saw it was
my boss calling. I picked it up and said, “Hello.” “Your lucky
night, Kid!” My boss told me. “Sir?” “Get down to the Crown
Plaza Hotel, find a Metro PD detective by the name of Gloria Johnson, she needs
our help on a quadruple homicide.” “Yes sir! I’ll be there in forty-five
minutes.” I hung up the phone. I put on jeans and a dress shirt, slipped
into my deck shoes and headed into the city.
When I arrived at the hotel
I found police everywhere. I went to the room that I was told was the crime scene.
Gloria was a very cute blond woman, standing by the door to the room. “Gloria
Johnson? Metro P.D?” I asked. “That’s me.” She said, offering
a firm handshake. I showed her my ID, “Special Agent Bill Smith, ATF. We’re
partners on this one.”
Story posted by Otter
on Saturday, October 13, 2007 @ 12:41:49 PDT
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