February 4th, 2016
. ***** You should stay at my place next weekend. Maxine
says there's going to be a great party with plenty of
Trannies for you to chase. *****
. That was the playful text that started my world
spinning in the opposite direction. I received it two days
ago and still haven't replied. At least I have an excuse. My
job as an audio engineer has kept me in a studio eighteen
hours a day for the last two days. I don't know what has been
worse, trying to make a low talent pop singer sound like a
diva, or feeling like I'm trapped in this no win situation
with Sarah. The mildly successful pop singer is paying very
nice money to get a mini album recorded in time for an online
release on Valentine's day. Every cheesy line of every overly
catchy love song reminded me that ten days from now was the
most commercially romantic day of the year. I never really
cared about it before. Even when I had a girlfriend, I went
through the motions, but I never really took it seriously.
Sarah knew she was asking me to stay at her place Valentine's
weekend. My last journal entry was all about the wonderful
night we had out, and how confused it left me about my
sexuality. What I didn't write about was the morning after
and why this Valentine's would either be the best or worst
day of my life. If I refuse to stay with her for the weekend,
will she forgive me? God knows I want to be with her. But how
can I, when I know there's a chance I might be gay? Gay... It
wasn't just the threesome with Maxine that had me daydreaming
about my next encounter with a penis.
. That night as we fell asleep, Sarah and I talked about
the bar and all the people we met that night. I was half
asleep when I admitting to wanting to take the bartender up
on his offer. I remember the sound of her humming softly as I
drifted off. Noon had come and gone before I opened my eyes
again. The first thing I saw was Sarah sleeping next to me.
Her red hair fanned out messily over her face and pillow. I
gently moved it from over her mouth and nose. She didn't so
much as stir. She was always a heavy sleeper and I slipped
out of bed to hit the head and make my way to the kitchen.
I felt bad about prying into the Olympics thing and wanted to
make it up to her with a nice breakfast. Her refrigerator
frustrated the hell out me. She had no sausage, no bacon, and
all of the eggs were pre boiled. I knew she took her training
seriously, but wow. At least she had some muffins. I took two
of them and put them in the oven. While they warmed I cut a
grapefruit and sprinkled sugar on it before peeling a couple
of her boiled eggs. I heard some water running and knew she
was up. As I took the muffins from the oven, my back was to
the hall and I didn't see Sarah enter the kitchen. Instead, I
felt her wrap her arms around me and rub my chest. I remember
being worried about how much it was starting feel like we
were in a relationship, but another sensation made itself
pressing. Sarah squeezed me, and I felt something strange on
my ass. It was hard and rounded and poked at my cheeks as she
wiggled her hips. I knew in an instant what it was.
SARAH
Good morning. Ready to have one of
your dreams come true?
With a click, the dildo she had pressed against my ass
started vibrating. It was a strong humming pulse that sent
shivers across my thighs. I turned to face her and my heart
raced as if wanted to jump from my chest. She was dressed as
a cowgirl... Well almost. She had the boots, the chaps, the
vest and the hat. Her hair was wet and pulled back under the
hat. She clicked off the vibrator and pulled toy guns from
her holsters, pumping them into the air as she danced and
twirled. Water dripped from her hair and her toned round ass
sparkled as she shook it side to side. That thing poking my
ass, it was the strap-on she was wearing. I watched it bobble
as she turned back to face me and replaced the guns in her
holsters. I laughed and blushed and asked her if she was
serious. She picked up a small bottle of lube from the table
behind her and squeezed a handful out. Rubbing the rubber
penis strapped to her hips, she answered me with authority.
SARAH (CONT'D)
Do I look like I'm joking?
I touched her on her cheek and tried to give reasons why this
was a bad idea. The truth is, I was dying to let her do this,
but I knew I couldn't. She was running. I told her that I
knew she was scared. She looked at me quizzically and stroked
the dildo.
SARAH (CONT'D)
I'm scared?
I gave her my serious face and held her hands. She began to
fret and tried to pull away, but I wrapped my arms around her
and held her until she stopped resisting and hugged me back.
. When she entered college, Sarah's father threatened not
to help pay her way if she majored in sports medicine. He
wanted her to major in business and accounting so she could
take her place in the family company. She refused, stating
that sports medicine would help her with her Olympic
endeavors and that she would find a way to pay for college on
her own if she had to. Her senior year, she was recruited by
Star Tech, a large company that provides nutrition and
fitness training for some of the biggest names in the NBA,
NFL, etc. She tried to run then. She moved back into her
parents house, apologizing for the past four years and
telling her father she was ready to go to work in the office.
It was her mom who eventually called me. I took Sarah camping
for the weekend and we made love for the first time. She
confessed to me how scared she was that she would meet all
the people she would need to know in order to help her dream
come true, and they would tell her she wasn't good enough. I
asked her if she remembered what I said to her when she
finally broke down and confessed that to me in tears? She
slugged me on the shoulder, then squeezed me tightly again.
SARAH (CONT'D)
You said I should thank them for
their honesty and train harder. I
forgot how much of an ass-hole you
are.
I reminded her that I also promised never to let her give up
on her dreams. She was the one who made me swear to it after
the first time we had sex; that as long as I was around, I
would stop her from doing anything that would mean giving up
on her goals. Even falling in love.
SARAH (CONT'D)
You did a shity job of it, you
moron?
She sniffled, and I realized she was crying. We held each
other in silence, until she pushed her way out my arms and
slugged me again.
SARAH (CONT'D)
You know How much I hate this mushy
crap, and admitting my feelings.
She went back to stroking the rubber penis she was wearing.
SARAH (CONT'D)
So now it's your turn to cry.
I asked her to do me a favor and give it to me rough. She
agreed and I said really rough. I told her I wanted to feel
the way she felt when Maxine's giant cock was splitting her
pussy open. I wanted to scream in uncontrollable ecstasy.
SARAH (CONT'D)
I'm going to fuck your virgin ass
til it bleeds.
. She walked around behind me, put both hands on my hips
and pushed me to the kitchen table. She pushed the rubber
cock against my ass, squeezed my cheeks and spanked them
hard. I resisted as she put a hand between my shoulder blades
and tried to bend me on to the table.
SARAH (CONT'D)
Looks like this stallion needs to
be broken before I can ride it.
She reached a hand around my waist and down into my boxers.
My penis hardened and grew as she tickled her way around it.
She grabbed my testicles and squeezed them until I yelped out
an ow. She pushed my back again, and pinned my chest to the
table. I felt my boxers being pulled down my legs and stepped
out of them when they hit my ankles. The next thing I knew
her teeth were sinking deep into the skin of my left ass
cheek. I clinched my teeth as I felt her bite down, then
moaned with relief as she gently kissed around the ringing
pain. The sound of lube squirting from the bottle came from
behind me, then I felt Sarah's wet fingers sliding between my
cheeks. Without warning, she thrusted a digit deep inside me.
"Aaaah!" spilled out of my mouth as she worked her finger
quickly in and out of my ass. It hurt like hell, but still
gave me an erection. It was the strangest sensation I ever
felt. Her knuckles slammed into my ass like a punch as she
drove her finger to into me, then she added another digit.
She pushed them as far into me as she could wriggling and
rotating them. Then she pulled them half way out and started
spreading my hole. I could feel how hard it was for her to
push her fingers apart with my ass clinching down on them. I
couldn't help it. The more I tried to relax, the tighter my
hole seemed to pinch around her fingers. She pulled them out
of me and I could feel lube dripping from my ass. I thought
the times I used a dildo on myself were going to make this a
walk in the park. When I felt her hands spreading my cheeks,
I held my breath with anticipation. The tip of her rubber
dong slowly started penetrating me...
SARAH (CONT'D)
Time to giddy up, horsey.
...and then I felt so much pain, that it made me cry out as
my penis went limp. She slammed her hips into mine, driving
the fake cock all the way inside me at once. She pounded me
and my ass felt like it was being torn open. I moaned and
yelped, as she hammered her toy into me over and over. My ass
was raw, but the penis grinding in and out of it began to
feel good. Then it felt better than good. I closed my eyes
and my own penis began erecting again.
Sarah was moving slower now. I felt my hole spread every time
she thrust into me. I breathed in deep when she pulled her
penis out of me, and sighed with pleasure as she drilled it
back in. Sarah stopped with just the head of the penis inside
my pulsating cranny. I gave her an "oh god, please don't
stop!", and she smacked my ass hard.
SARAH (CONT'D)
Enjoying this?
I gave a breathy "yes"
SARAH (CONT'D)
Good. Then let's take things up a
notch.
She clicked the vibrator on to full and my knees turned to
jello. She was pounding the dildo into me again only this
time I was yelling in ecstasy instead of pain. I reached
behind me and spread my cheeks yelling "deeper!" at her. She
grabbed my hips and drilled me so hard it started to moved
the table. My penis exploded shots of cum down my legs and on
the kitchen floor. She kept going. She fucked my ass until I
couldn't take any more. "Stop... stop..stop..." I cried, and
let my chest lay limp on the table. So many parts of my body
tingled with pleasure that I didn't want to move. She smacked
me on the ass again and the feeling swept across my back in
orgasmic ripples.
. She doodled on my back with the tips of her fingers
while I lay bent over the table panting. Finally I stood up
and the dildo made splirting sounds as it slid from my ass.
She wrapped her arms around me.
SARAH (CONT'D)
You do know, that you're cleaning
all this up.
With that, she let me go and quickly skipped out of the
kitchen down the hall. My ass throbbed and tingled as I
walked to the counter looking for a towel to clean up with.
. What the hell had happened that morning? My best friend
told me she was in love with me, right before intentionally
helping me realize that I'm gay? ...Gay... There's something
I never thought I'd say in my life.
It's not exactly a surprise that I feel this way; but
actually admitting it, even to myself... Is this the reason I
suddenly feel the need to keep a diary? All the years of
people closest to me; family, friends, teachers making it so
clear how wrong it was to even think about feeling this way.
All the guilt and shame... and fear. Now the woman who pushed
me past all that is in love with me. How exactly do you
respond to that in a text?
End.
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