I’ve been into Japanese Animation for years, starting
back in college when I was a member of the campus anime
club. I’ve always been fascinated by such incredible
art, and the different perspective on things that the
Japanese use. So I should have been ready for something
strange when I went to this last convention.
I’d booked a room at the con this time instead of
offsite. Offsite is nice for being discrete, but when
the music’s pumping at 2 AM, and the drinks have been
flowing all night, it really sucks to have to get a cab
to your hotel. The parties tend to get loud and sloppy,
since most of the people there are college age or
below. I’m a little older than most, but since I’ve
been an otaku for so long, everyone accepts me into
even the youngest gatherings.
So, it’s 3 AM. The dance is starting to wind down, and
I’m outside having a smoke. The wind is nasty, and it
really sucks having to head outdoors in winter for a
quick hit of nicotine, but what are you going to do.
I’m sucking down the last of the cigarette, when out
walks a vision. Now, I’ve been drinking pretty heavy
all night, but even so, she was definitely worth a
second look. Dressed in a sailor suit schoolgirl
uniform, she bounced out the door and asked if I could
give her a smoke. I pulled out my pack and lit one up
for her, watching as she expertly sucked on the little
round stick.
I didn’t know if I should try for her or not. After
all, a lot of the girls here are definitely jailbait,
and I’m to pretty to go to prison for 5 to 10. The
cigarette isn’t a clue anymore because you never know
these days, but then she pulled a beer out of her
backpack, dropped to the railing, and started sucking
on a cold one. Now, I know the only alcohol allowed in
the place was from the hotel, and they insisted on
having a real bartender and security. Not one of those
half assed “security guards” that cons like to use,
usually 15 year olds that are working for a free badge
to the events, but real off duty sheriff deputies. So I
figure I’m pretty safe, since she probably had her ID
checked by at least 2 professionals tonight.
We start talking about anime, going over various
favorites. Mostly she seems to like the YAOI stuff,
like Fake, or Fruits Basket. I can take that stuff or
leave it, I’ll watch or read anything once, but I’m
more into GTO. I can understand a man that becomes a
teacher so he can look up schoolgirl’s skirts. While
we’re chatting she starts to shiver a little. Pitching
my butt in the ashtray, I say, “Isn’t it a little
chilly to be out here dressed like that?”
“I don’t have a lot of choice,” she replied, with a
sexy little laugh. “After all, this sort of party is
much more fun if you’re in full cosplay mode!”
This makes my heart skip a beat. Most of the girls I
know that are into cosplay are also into just about
everything else if you know what I mean. Casually, I
asked, “Would you like to head up to my room? I’ve got
a place here at the hotel. We can smoke there if we sit
on the balcony, and I picked up something a little
tastier than that crappy Budweiser you’re sucking on
now. What do you say?”
She gave that little evil laugh again, and said, “Is
that the only thing I’ll get to suck on if I head up to
your room?”
At this point, my heart went into overdrive. I’m 29,
and this girl was maybe 22 tops. She was definitely
cuter than most, and we were into the same sort of
things, or so I thought. I picked up her bag and held
the door for her, gesturing for her to enter ahead of
me. The lobby was pretty well cleared out, since most
of the young ‘uns had gone to beddy bye already, and
the older kids were up at the con suite, racking out
for a little R&R. We quickly hopped on the elevator and
took a ride to my floor. I was going to try to get a
room right on the con floor, but I had figured I might
not get any sleep if I pulled that, so instead I was 2
floors further up. We popped off the elevator and
quickly made it to my room. I swiped open the door with
my card and we quickly slipped into the room.
I like to be prepared, even though I hadn’t really
expected anything much to happen tonight. I had already
grabbed a bucket of ice, and I had a couple of bottles
I had picked up at the liquor store sitting on the
desk. One nice thing about the room I was in was that
they included a full sized coffee pot in each room. I
quickly started a pot brewing, and grabbed a couple of
cups from the credenza. While the coffee brewed, I pull
out everything I needed to make sure we had some fun.
Bushmills whiskey, sugar, cream out of the minibar
fridge, and a can of whip cream. Her eyes lighted a
little when I pulled that out, but I laughed. “It’s for
some Irish coffee honey. Nothing warms you up quite
like it!”
I set about whipping us up a quick set of drinks, going
heavy on the whiskey. After all, if she was planning on
driving anywhere she wouldn’t have had the beer anyway.
I handed her a mug, and sat down in the chair by the
desk. She sprawled face down on the bed, her legs
kicking at the air and a pillow under her breasts as
she licked up some of the whip cream. All of this was
driving me wild. I love the Japanese schoolgirl look,
especially when she has beautiful red hair and huge
green eyes that you could just sink into. The room came
with a DVD player, so I pulled out one of my purchases
from the con and slipped it into the player. “Tell me
what you think of this one.” I asked her as I hit play.
The title was a hot little hentai number. The main
character looked kind of like her, although I liked the
one in the room better than the one on the screen.
After all, this one was warm and slowly getting
intoxicated. I sat down beside her on the bed and
started working on her back, massaging her through the
shirt. She purred, and snuggled into the pillow a
little harder, as I worked down her taut back in to her
ass and legs. Teasingly I ran my finger from her feet
to her ass, feeling her thong panties under her skirt.
She clenched her legs a little tighter, so I started to
worry that I had gone too far, when she placed her
empty mug on the bed beside her and grabbed my hand.
“Hmm…” she moaned, “I’ve always wanted to try
that…” I glanced at the screen as the girl in the
film was forced to take a huge cock in her ass. “Let me
get you a little wet and see if we can do that!”
She pulled me in front of her, and pulled me closer to
the bed. Using her finger, she scooped up a little bit
of the left over whip cream from her cup as she undid
my jeans. I never wear underwear, so my hard 8-incher
sprang right out in front of her. She squealed, “Oh,
what a big one it is!” and used the finger to trace the
whip cream down my hard dick. The feel of her inch long
nails running down my pecker was enough to make me
almost come right there, but I really wanted to make
this last. She stuck out her tongue and began to lick
up and down my shaft, paying special attention to where
the whip cream was quickly melting off. As she slopped
on my dick, it was all I could do to stop myself from
ramming it right down her fucking throat. This was one
of my best fantasies, a hot schoolgirl uniformed chick
sucking me off! I couldn’t believe this was happening,
but I knew that more was yet to come.
Her nails tickled my dick and balls while she slurped
on my tool, and I could feel the fingernails sliding
around to my ass. I was going to be marked when this
was over, but boy was it ever worth it. I even spread
my legs slightly as she ran her nails lightly over the
skin between my balls and my asshole, tickling me in a
most erotic way. I pulled away and told her to sit up.
When she did, I pulled her sailor suit tunic up over
her beautiful breasts and buried my face in them. I
loved the feel of the nipples against my face and
tongue, and I really enjoyed the slight hint of
muskiness from where they had been trapped during her
partying at the dance.
I worked my way up her neck, biting and kissing my way
to her mouth, where she immediately started probing for
my tongue. As we dueled with our mouths she grabbed
hold of my balls and gave a little tug. “I want you to
fuck me in my ass. Just like in the movie. Fuck me up
the ass, right under my skirt.” I reached down as
though to tug off her little panties and she said, “No,
leave them on. Just pull the thong aside and fuck me
while I’m still wearing them. It will make me SO
hot…”
Now I’m not a man to leave a woman in a desperate
situation so I decided it was time to start quenching
the fire this little girl obviously had in her little
bottom. I placed her over the edge of the bed, with her
cute little ass in the air. I got down behind her and
began to lick and bite her ass cheeks. She giggled and
shivered, but when I finally took my first lick at her
gorgeous brown eye, she moaned. “Don’t play around, I
need you!” she panted. As my tongue darted into her
cute little ass like a hummingbird into a flower, she
moan again. “Do it! Do me now! PLEASE!”
I placed the head of my slicked up dick at her tight
little hole and started to shove. The angle was almost
right, but not quite, so I slide the pillow down under
her hips, raising her slightly. Now it was perfect. I
started to slide into her ass. It was like a pussy at
full ripeness. Obviously this wasn’t the first time
someone had been up there and I was sure I wouldn’t be
the last, but it was still tight and hot and moist.
No matter how used an asshole has been, it’s always
going to be tighter and hotter than any pussy can ever
be. I mean, don’t get me wrong, I like fucking a girl
regular too, but using her ass I can feel every ripple
in her tight dark channel as my dick works its way up
her chute. I started working my way up, stopping when
she tensed up a little at the half way mark. “It’s so
big…” she sighed, with that fluttery little catch in
her voice. “I don’t know if I can take it all!”
“Well, we’re gonna find out sweetheart, cause I don’t
plan on pulling out now!” And with that, I continued
plunging into her abyss. Soon I felt the skin of her
ass against my crotch. I shave because I love the
feeling of that skin to skin contact when you’re fully
inside her. I started to pump, slowly at first, a
little at a time. I would pull out a little then plunge
right back in. Then I started pulling out further,
leaving just the head inside until she begged me to ram
it home. In and out I plunged into that hot little ass.
The whole scene was made even more lewd by the sailor
skirt thrown up over her ass cheeks, the thong scraping
along the edge of my dick each time I pulled out. I
couldn’t believe how hot this had gotten me. I’ve never
had anything quite like this, I thought, and made a
mental note to make sure to pre-register for next years
convention. I leaned over her back, on my elbows,
pulling at her tits crushed under her body, biting her
neck and ears. “I’m fucking you. I’m fucking you. I’m
fucking you like I’ve never fucked anyone before. My
god you’re hot. I love the feel of your ass against my
body. I love the feel of your hot little asshole. Can
you make me come? Can you bitch?”
As I said this I felt her start to clench and relax her
anal muscles, milking my cock like an automated milking
machine works on a cow. I groaned in her ear, thrusting
harder and harder up her tight little ass. “I’m going
to cum up your ass bitch. How do you like that? I’m
going to paint your insides with my cum. Are you ready
for it bitch? Are you ready?”
“Oh god yes! YES! YES!” she screamed, as my boiling
load started screaming up my cum tube. “Cum in my ass!
Cum in my hot little schoolgirl ass!” That was all it
took. I started blowing wads of scum up her chute as I
rammed myself repeated balls deep into her ass. I even
managed to keep going for a while, because I was still
hard even after coming. After a couple of more thrusts,
I felt a deep tearing sensation in my groin as I
delivered up the last of my pearly white cum.
I fell forward onto the bed and still lodged in her
asshole I rolled over, putting her on top of me. She
sat up, trying to keep me captured in her ass. I sat up
and grabbed her tits from behind, roughly working them
in my hands as I pulled her back down onto me. I rolled
her over into a spoon, and cuddled up behind her, still
inside her as we slowly stopped panting after our cum.
The alcohol and the adrenaline rush finally caught up
to us, and I started to drop off to sleep, holding her
in my arms.
About an hour later, I started wake up a little bit as
I felt her licking my cock and balls. I was still
exhausted from the last time, as I don’t know when I
had last cum that hard, so I just laid there and
enjoyed the sensation as she licked and sucked her way
from the top of my cock to the base of my balls. I felt
her playing with my back door, and shifted my legs
slightly to give her room. If she was able to get me
jump started again, I didn’t care how she went about
it. I was rewarded with the feeling of a finger
entering my own hidden hole.
I’d done this before of course. Who hadn’t? When you’re
not 18 anymore, you need to know the tricks if you want
to get back up again in a hurry. So I relaxed as her
warm spit covered fingers played with my anal opening,
first one finger then another working it’s way up my
brown eye, as she used them expertly to play with my
prostate. I could feel my body starting to respond to
the expert technique, and sighed as she pulled her
mouth away with a lewd little string of spit connecting
her lips to my dick. Still playing with my ass, she
worked her way up my body and began planting a kiss on
my mouth.
I felt the fabric of her skirt bunching up between us
as her fingers probed more and more expertly in my anal
passage. Then I felt an emptiness as she removed her
fingers and kissed me harder than ever. I felt
something knocking at my back door, and then realized
that it wasn’t a finger any more. My eyes got wide as I
felt her hard cock enter my virgin ass, pushing hard
through the sphincter holding it closed. The chick had
a dick! I could not believe this, but as she held my
arms to the bed and forced her way into my ass, I
realized that I didn’t have a choice but to believe it!
At first I was shocked and confused. I am not gay, and
have never had anything but a finger up my ass. I
couldn’t believe this was happening to me! But as the
pain passed, the hardness of my cock bunched into her
skirt was enough to let me know that no matter what I
had thought in the past, I really was enjoying this. As
she realized I was no longer fighting it, she quickly
took my hands and placed them on her tits, I quickly
started playing with her hard nipples as I felt waves
pleasure roll through my body.
Each thrust of her 6 inch tool rode over my prostate,
making my dick harder and harder. I felt wanton,
playing with these gorgeous tits while getting plowed
up the ass by a hot thick dick. As I felt her start to
cum up my ass, my own hard boiled cock suddenly started
spurting cum between us, all over her skirt, and I
pulled her down to me and kissed her hard on the mouth.
As soon as she came, I could feel her slipping out. I
tried to hold her in, but I wasn’t used to this, so she
slipped right out of my hard used ass.
She stood up, and the skirt dropped down again. And
there she was, again a beautiful woman, wanting to be
used. I sat up and we lit up a couple of cigarettes and
talked about it. She told me that she never did this
sort of thing, that she was actually fully in character
the whole time she was here.
This was the first time she had ever slipped like this,
and she hoped that I wouldn’t give away her secret.
Like I could, since then everyone would know I had been
fucked up the ass by this beautiful woman. I told her
that this was a first for me all around. We sat and had
a quick nightcap, then she kissed me again and said she
would see me later. With a wink, she disappeared from
the hotel room. I took a shower and hit the bed
exhausted and needing to be at the con early the next
day, I quickly fell asleep.
She came back the next night and we tried even more. I
still can’t believe that this happened to me. But next
year, we’re talking about sharing a hotel room at the
con, so we don’t have to sneak her into my room.