Date: Tue, 3 Mar 2009 18:04:27 +0200
From: Sissy Whore <munanlutkuttaja@hotmail.com>
Subject: A trip to hell part 1

-Not suitable reading for people under 18 years old!-
If you would like to send me feedback, send it to munanlutkuttaja@hotmail.com

INTRO

I have been dating now for 3 months, she is the first girl I have ever been
with, she took my virginity and she has shown me so much. I used to be the
sad, pathetic nerd of my school but ever since she came up to me and asked
me out and started to date me, I have become the biggest rumour of the
school. You see, I am not a jock, I am a small, blond, no muscle school
nerd, I study hard, I dont really have many friends, other than other nerds
of the school and I am totally inexperienced with girls, well I used to be.
I turned 19 last month and believe it or not, my girlfriend is 27 years
old, which is the cause of the rumours, why does a beautiful girl choose a
person like me. I still cant believe how lucky I am, she came up to me, she
was the one that took the initiative and still to this day she is the one
who knows more about relationships so I listen to her and I take her
advice. I would do anything for her, because she has done so much to me,
and basically she made sex available to me, and boy, do we have sex alot!
She likes it all, she takes it in the mouth, she likes me to go down on
her, she likes anal sex and everything! And always she compliments me for
it, calling me a stud and all I can do is devote my love to her. She also
likes games and sometimes when we play cards, the one who wins gets to take
the charge and I usually lose. The most fun experience she made me do once
was to give her oral sex the whole time she was making food, I was licking
her for more than an hour and boy, was eating food a hard job after that,
my jaw had a hard time chewing or even moving but I enjoyed every moment of
it.

It was three weeks ago when we decided to take a trip together, it was her
idea, as most of these good ideas are. One evening when we were watching a
movie together, and for the most time we had been cuddling she said that we
should do something spontanius, I jumped up at that idea because at first I
thought it was about sex and then it became alot better. She suggested that
we take a trip together and I said something along the lines of a bus ride
to the other side of the town and her response was calling me a silly boy
and she said lets go to brazil. My jaw dropped and I was of course more
than happy to go to brazil with her!

PART 1
The airport

I never have gotten over the fact that she is older than me, she cares for
me, for who I am and that she is actually taller then me. It is every boys
dream to meet a hot chick who knows how to please a man and is spontanius
and likes to adventure... I had all that! I love her, I love Jessi! She was
holding my hand and guiding me thru the crowds of people and I was
following her lead, holding her hand and watching her golden hair move as
we headed to the right place to board our plane. We stopped at the gate and
she turned to face me, she kissed me and she said "See you on the other
side." And with that, she turned on her heels and headed to the door that
had the text "Staff only." She looked professional and I enjoyed every
moment of watching her tight ass sway in her skirt as she walked thru the
door. She had been working as a stewardess for 4 years now so this flight
was practically free for us. I stood still for a moment infront of the gate
to board the airplane, I imagine how much fun, how much sex we were going
to have in Brazil and everything else. My last thouhgt before boarding the
aircraft was "How perfect is my life!"

The airplane took off, and it had been an hour before I saw Jessi and we
were half way to Brazil already. The food had been served and Jessica came
to sit next to me, she said that she wanted to play cards, same rules as
always, winner gets to make the decisions. I was blushing slightly as I
thought that other people might be hearing us talk about sex games. The
game was poker and for the first time in poker, the game ended a draw. I
was suprised in this and I had already decided that if I win, I will get
oral pleasure in the airplane toilet. I was snickering slightly as we
decided to determine the winner by one draw, bigger card wins. I took my
card first, it was a jack so I was feeling pretty confident. Jessica smiled
at me and she drew her card and looked at it. She smirked devilishly and
whispered in my ear "Follow me to the staff section of the plane and lets
show our cards there to determine the winner, hm?" I nodded, already
sporting a semi hard on with my 6" dick. I followed her to the back of the
plane and a small set of stairs down to the staff compartment, it was a
small space where they had all the coffee machines and food supplies but
the most important thing was that we were in private and there was a door
separating us from the rest of the plane. Jessi closed the door as soon as
I had entered and she dared me to show my card first. I was very excited
and I flipped the card from my pocket, proudly showing my jack. Jessi
smiled and said "Uh-oh, looks like wittle Sam is at my mercy again." And
with that, she flipped an ace to her forehead, bathing in her victory,
giggling slightly. I knew I had lost and I did what I had been doing for a
while now when I lost, wich was actually every time, I kneeled in front of
her and said "I am at your service but next time, it will be my turn" I
winked at her and she brushed my cheek with the back of her hand and
smiled. "Okay, Sam, this time I have something very kinky in store for
you." She went to a shelf and behind some boxes she took a plastic device
and it looked frightening because it outlined the shape of a small
penis. My first reaction was surprised and a little frightened but it soon
turned out be just plain horny. She commanded me to lower my pants saying
"I want you hornier than ever once we get to that hotel room, so I am going
to make sure you are more than that. Now, I know you like anal play but
this time we are going to turn the tables." I was puzzled as she produced a
weird looking device, I had no idea what it was or what it was for but it
looked remotely like an insertable device. Next to the plastic cage, this
was starting to look very kinky, almost too much for me but she reassured
me. "Now, this is going to stay between and there is nothing gay about
this, it is just a game and I want to play with you, okay?" When she said
the word gay, I became nervous and she could easily see that from me. She
reassured me and asked me again to drop my pants, which I did. She kneeled
in front of me and said "Trust me." Which I did, I closed my eyes, kept my
hands to my sides as she pulled down my boxers and started to massage my
cock which was painfully erect now. She rubbed my dick for a while before
guiding it to her mouth and ever so slowly started to suck me. I tried to
rock back and forth because I was yearning for release and she immediately
stopped me with her hands so I stayed still. Her hands went to my butt
cheeks as she was giving me slow oral pleasure and soon I felt her hands
between my cheeks, I became worried but I enjoyed it, and her mouth felt
even better because I was as nervous as I was when I was a virgin. Her
hands touched my rosebud and I immediately tightened up, I didnt like where
this was going but I trusted her and from previous experience, I trusted
this was going to feel good in the end as it always had. Her hands left my
butt and for a moment I tried to feel where they where as my eyes were
closed and they returned to my butt as I feared. This time however, they
were slick with some gooey stuff and her fingers were very slippery, they
easily went between my butt cheeks without any friction. Again, my rosebud
was touched and I tightened and immediately after, her finger slipped
inside me! I gasped loudly and I was surprised that it didnt hurt one bit,
there was only very intense pressure. As her finger was invading me, she
started to suck my dick and I felt like my knees were going to give
out. Her finger started to do this back and forth motion, every time
pulling back as far as just outside my spincher and then back in which
caused my dick to twitch every single time. My butt felt very slippery, her
hand was coated with some form of lubricant. I felt like my dick was full
of nothing but blood and sperm and I was ready to beg for release. Jessis
finger left my butt and I felt relieved because to my surprise, it also
eased my almost too strong feeling of cumming. I was confused how her
finger had affected me so much and I didnt know what to think, I wanted to
try it again but dared not to ask because she was in charge and it might
seem gay if I did. Her head was doing wonders to my dick as her suction
increased, her movements still were so painfully slow that there was no way
that I would cum from it. Then, her finger touched my butt cheeks again. At
least, I thought it was her finger but it wasnt, it was something slightly
larger and round. I felt it tickle me as it passed my cheeks and rubbed
against my lubricated cheeks until it met my spincher. I knew what jessica
was doing and I decided to go thru with it, for her. I didnt know what it
was that she was going to insert into me but as she again increased her
suction and started to work her tongue violently on my dick now, I knew she
wanted me to go thru with this. I moaned and I think she took it as a sign
because the the intruder in between my butt cheeks started to press in. I
moved my hips forward to escape the intruder and Jessi places her other
hand onto my stomach to hold me still and the pressure was increasing in
both my dick and my spincher. Soon, I felt defeated as the round object
passed my spincher and it was shaped more narrow towards the length so it
felt like my ass was eating this object more inside now and slowly it sinks
in me until I feel it plop inside me and again as my spincher is without
pressure my dick twitches violently. I leak a steady stream of pre cum into
Jessis mouth and I am ever present with the intruder in my ass and it feels
like it is going deeper in my ass, slowly but surely. Then, something else
touches my butt cheeks, at first I hope it her hand but no, it is a round
object like last time, this time slightly bigger. It too, makes it way to
my spincher and I feel like crying, what is she doing to me?! Whatever it
is, it feels good but also very embarrassing and humiliating, my dick is
painful now, her tongue assaulting my purple head so badly. This new
intruder also starts to push inside me and I know what follows, a
wonderfully, yet embarrassing feeling of pleasure pulsing from my ass as
the slightly larger object goes inside me. And it also is shaped more
narrow along its length so it goes inside me as if my ass wants more inside
me, this object is considerably longer and I feel it make contact with the
first object, forcing it deeper. Both of the objects stop inside my bowels
as I feel the shape at the entrance of my butt, there is a widening of sort
that fits between my butt cheeks but does not fit inside my butt. There is
actually a tear running down my cheek as it feels too good, something so
wrong feels so weird and pleasurable. And then, my world come tumbling down
as Jessis mouth leaves my dick and still, I feel intense pleasure, I am
painfully aware where the pleasure is coming from. I open my eyes and I see
Jessi now standing in front of me, immediately closing on me, kissing me
VERY passionately, our tongues exchanging saliva and I part with her
kissing, embarrassedly saying "Jessi, Im sorry, I dont really like this, it
feels awkward." I was lying. Jessi smiled and said "Do it for me baby, and
besides, look at your dick, I dont think it has ever been that big.
Besides, Sam, there is nothing to be embarrassed about this, beacsue it you
and me and no one else, okay?" I nodded slightly and I did admit it, althou
not to her, it did feel good. Jessi smiled infront of me and planted a kiss
to lips, I felt weird, I didnt dare to move because I knew what it would
cause in my butt. Jessi looked at me and obviously was enjoying this. She
lifted her hand and was holding a very small remote with two buttons, she
said "Sam, in your butt, there is a small P-spot stimulator, I think it is
called aneros prostate massager if I remember correctly, just enjoy it
because many straight men do." With that she grinned wide and pressed the
button on her remote. With that every single muscle in my ass spasmed as I
felt an intense vibrating motion from the insides of my bowels. This time
my knees actually did give out and I kneeled onto the floor and took
support with my hand from Jennis leg. She was looking down on me and
giggling slightly "Feels good, right!" I couldnt utter a word as I felt the
vibration become more stronger as Jenni was rapidly pressing a button on
the remote "Just wait Sam, its about to do something wonderful to you!" The
pressure in my bowels felt like it was shifting, it was like, something was
heading towards my penis and with every single pulse, which were probably
many hundred in a second, a closing pressure was going thru my penis until
I felt something let loose inside me. I was relieved that it was my bowels
that let loose but it was an explosion of an orgasms, the feeling was
intense, at first nothing came out of dick, just a wave of pleasure after
another just like in a normal orgasm but it continued a lot longer! I was
spasming involuntarily the whole time and Jenni was standing next to me,
giggling the whole time. The pulsing continued and after a long time of
having a dry orgasm my penis leaked its sperm but it didnt come out flying,
it just poured out slowly. My eyes were tightly shut and as the intense
orgasm started to fade out, I felt the intruders in my bowels become ever
more present now, uncomfortable even. And when my orgasm was over, my penis
starting to o flaccid, the things in my ass, felt wrong, painful and very
uncomfortable. I reached with my hand to take them out but Jenni stopped me
"Nono Sam, I am not done yet. Come one, I can guess that it feels very
weird now but just hang tight Sam. Stand up." She offered me a hand and
helped me to stand up, right after which she kneeled infront of me and
cleaned my dick of any remains of sperm. The buzzing was still continuing
in my ass and I was trying to get used to it because it was everything but
nice. I was flushing red and I hoped that Jessi would allow me to remove
what-ever-it-is that is in my ass. I felt Jessi pull something around my
cock and I looked down to her curiously, trying to ignore the vibrator in
my ass and see what was she doing, it was a plastic ring that she
skillfully and without pain put around my dick and behind my balls. I was
puzzled and then I remembered the plastic device, she must be putting that
on me! Again, I was becoming slightly aroused and I felt myself become
again so much more aware of the vibrator in my ass but the uncomfortable
feeling fading away with every second and the embarrassingly and
humiliating feeling coming back as it started to feel good. Jessi was
working quickly as she could feel from my dick that I was becoming aroused
again. She placed my dick inside the plastic mold and I realized with that
moment that it was so small that I wouldnt be able to become erect. Jessi
giggled again and placed a small lock onto the device and sealed it shut
with it. My hands were trembling, the vibrator working inside me causing me
to blush and sweat heavily and my cock unable to become erect, I felt
violated, yet super horny. Jessi stood up in front of me and grinned "You
should see the look on your face, Sam!" She giggled and then helped me to
step out of my pants and boxers. I was puzzled and she produced a set of
strings that looked heavier than my previous ones, I asked her what were
they and she shushed me and said that I will see soon. She the boxers open
and I stepped in to them one leg at a time and Jessi pulled them up. The
boxers had a string inside them because as she pulled them to my waist, I
felt them being very tight in front of me, forcing my cage penis into a
small space and between my butt cheeks, I felt a sort of string sink
between them and touch the vibrator's base. And these boxers, once in
place, Jessi had pulled so up that they were above my hip bones and
tightened them from the waist and locked them in place. I was mortified, I
looked at her with a "What the hell are you doing?!" kind of look and Jessi
smiled some more and his two sets of keys between her breasts. The boxers
would be impossible to remove without cutting them open because they were
so tight above my hip bones. She kisses me on the lips "Sam, this is my
plan to keep you aroused thru the rest of the trip, to make it fair, I will
give you a remote that will control the Aneros buzzing inside me right now
so we can both control each other." She grinned and gave me an opportunity
to speak. "Jessi, please, ease it with the vibrator, its killing me." I
felt myself leak precum into my new cock cage and Jessi was smiling infront
of me. "Alright, go down on me and make love to my pussy with your mouth
for 20 minutes and I will consider making your state a little more
comfortable but first admit it, it feels good, right?" I blushes and nodded
sheepishly, admitting to her that it did in fact feel good in a sick way. I
kneeled infront of her and submitted to licking her pussy for the next
twenty minutes.


To be continued...