Date: Fri, 21 Aug 2009 00:35:11 -0400
From: Andi <SissyAndi@Safe-mail.net>
Subject: Andi's Adventures Part - 24 (TG-High School)

Disclaimer: SissyAndi stories contain sexually explicit descriptions of
consensual and Non-Consensual sexual activity and are not suitable for
reading by anyone under the age of 18, or anyone offended by reading such
material. These acts include bisexual activity, cross-dressing and other
fetishes and perversions. The characters in these stories are fictional.
All Stories are the property of the Author.  Any feedback would be greatly
appreciated. Thanks.

Authors Note: The following story is part of the ongoing saga of Andi, a 15
year old, cross dresser who is 5'9" 130 pounds, long blonde hair and blues
eyes.  She has a set of perky 32B size Breasts.

While it is my hope that each chapter will be entertaining as a stand alone
story, I suggest that all new readers go back and read the "Andy And The
Team" series, as well as previous entries in the Andi's Adventures Series.
They contains a lot of back ground information that will help explain each
story.

Andi's Adventures - Part 24

I awake in a strange bed, the sun is just starting to rise, the warm rays
filtering through the window.  I look over and see a very handsome man
sleeping beside me, snoring lightly.

I am still wearing my black panties, garter belt and stockings. My little
black dress was no where in sight but then I remembered taking it off in
the living room.

Memories of the previous night come flooding back as I run my hand across
his muscular chest and down his nude body.
_______________________________________________________________________

It was Friday night and I agreed to go with Jamie to a local teen club.
Jamie's cousin was the head of security for the club so we got in for free.
I tried to talk Jamie into going to the club as a female but he said there
was no way he could do that because no one in his family besides his Mom
knew that he liked to cross dress on occasion.  If he went dressed up, his
cousin would recognize him and his secret would be exposed.

So I went as Jamie's date.  When we got to the club Jamie introduced me to
his cousin Tim.  Tim was a senior in college and worked at the club on the
weekend. While Jamie was a good looking guy who made a really sexy girl,
Tim was all MAN.  He must work out constantly to look like that.  He was
6'3", Short Sandy blonde hair, gorgeous blue eyes.

Tim was wearing tight jeans and a really tight black T-shirt with the word
security across his chest. All the young girls in the club were drooling
over Tim.  I know he made my mouth water.  I could not help stealing
glances at his crotch wondering how big his cock was.

Jamie and I found a table and order some soft drinks.  Most of the boys in
the club were dressed casually while the girls tried to look sexy in
dresses and short skirts.  The music was loud and upbeat.  Jamie and I
share a couple of dances.  One was a slow song and I rested my head on his
chest and felt his hands on my back, then my butt.

When we went back to our table, I noticed Jamie looking at this really cute
redhead.  I nudged him and told him he should ask her to dance.  He smiled
and said but I was his date.  I told him it was ok I didn't mind.

I watched as Jamie lead her out on the floor.  Jamie was not a bad dancer
but the red head was pretty good.  They made a cute couple.

I was sitting alone sipping my drink when Tim came by to see how we were
doing, I told him that it looked like Jamie was doing great and pointed to
the dance floor where the red head was grinding her hot young body against
Jamie as they danced.

That was when Tim told me he did not know what Jamie was thinking, he came
here with the hottest girl in the club and he left me sitting here to dance
with someone else.  I told Tim thank you but that Jamie and I were just
really good friends.

I danced with a few different guys through out the night, no one I really
liked enough to dance with a second time.  Jamie and the redhead came back
to our table and he introduced her as Sharon. She pulled Jamie closer to
her when she seen me.

We sat and try to chat over the music but it was a lost cause so we just
watched the crowd.  Since it was a teen club it had to close by 10:30.  At
about 10:15 Sharon who turned out to be 17 said she had to take her friends
home.  Jamie and Sharon traded a deep wet hot kiss good night and Sharon
told him to call her.

Tim came by again and asked Jamie how we were getting home and we told him
on the bus.  Tim told us if we wanted to wait he could drive us home.
Since I really hated riding the bus we decided to take him up on his offer.
Jamie said it was too hot in the club and asked him if we could wait in his
car.

Tim handed Jamie his keys and told him the car was parked around back
behind the club.  It was dark and kind of creepy back there.  Tim had a new
big SUV.  Jamie unlocked the doors and he crawled into the drivers seat.  I
got into the passenger seat.

Jamie asked me if I had fun, and I told him yea, but apparently not as much
fun then he did.  He laughed and said he did enjoy dancing with Sharon even
if she did leave him with a painful hard on.  We both laughed.

That is when he looked at me with that crooked smile of his, "Ah Andi,
could you help me with that.  please?"

"Oh so you leave me sitting so you can be with another girl and when she
will not put out you come to me for help."

He started to apologize until he realized I was just teasing him.  I
reached over and rubbed the bulge in his jeans.  Jamie moaned and reached
down and unzipped his pants and fished out his hard cock.

I started working my hand up and down the shaft and heard Jamie let out
another low moan.  Jamie reached behind my head and pulled it down toward
his cock.  I resisted but Jamie continued to force my mouth toward his
erection.

I heard him say "Come on Andi, suck it for me, I need to get off really
bad."

I opened my mouth and took the head between my lips.  Jamie was still
applying pressure, forcing more of him cock into my mouth.  I felt the head
hit the back of my throat and I knew I had the entire length in my mouth.

Jamie eased up and let me pull back some then he forced my head back down.
Sharon must have really turned Jamie on because I had never seen him this
aggressive.

I finally managed to pull my mouth off of Jamie's cock and I gave him an
annoyed look.  He looked amused.  I just sighed and went back to sucking
the head of his cock.  I squeezed his balls while I started working my
mouth up and down the shaft again.

Jamie had decided to let me work at my pace and not his.  I knew I needed
to hurry though because Tim would be coming out soon, so I started to work
my magic.  I would vary the speed at which I sucked his cock.  I would bob
my head up and down quickly, then I would slowly and lovingly work my lips
up and down the length of his cock.

I felt the head of Jamie's cock enlarge and I new from experience that he
was about to cum.  I pulled back and sucked hard on the head.  Jamie thrust
his hips forward and started cumming in my mouth.  I swallowed quickly and
was proud of myself for not losing a drop.

I was wiping my lips off with some tissues and Jamie was zipping up when we
seen Tim coming around the corner of the club.
_____________________________________________________________________

On the drive to Jamie's house I noticed Tim kept checking out my legs.  I
turned to talk to Jamie in the backseat and I let the hem of my dress slide
up a little showing off more of my legs and the top of my stockings.

I felt the car swerve and Tim's eye went back to the road.  I just assumed
that Tim would drop us both off at Jamie's house and I would take the bus
home but Tim said, "Now what kind of gentleman would I be if I left a sweet
young thing like you to fend off perverts that ride the bus late at night."

After we left Jamie at his place I scooted over close to Tim and gave him a
kiss on the cheek.  I let my hand linger on his arm as I thanked him for
giving me a ride home.

Tim said it was still early and it always took him a while to wind down
after work.  He asked me if I had a curfew and did I have to go straight
home.  I told him that my Mom was away on a trip with her girlfriend and
that I was suppose to call her and tell her I made it home ok.  With that I
pulled my cell phone out and dialed Mom.

I was a little surprised when Jillian, my Mom's boss and lover, answered
the phone.  Jillian told me that Mom was a little tied up at the moment and
laughed.  I heard mom moan in the background.

I asked Jillian to tell Mom I made it home ok and I would talk to her
tomorrow.  Jillian told me she would let my her know and the phone went
dead.

"There, I am covered for the night, so to answer your question, no I don't
have to go home right away."

Tim smiled again, "lets go back to my place and hang out."

"Ah Tim, we need to talk about something before we go any farther."

Tim looked at me and seen the serious look on my face so he pulled into a
deserted lot and parked.  He turned the Car off and turned to give me his
full attention.

I did not really know how to start bet decided that honesty was best.  "Tim
I feel an attraction between us but I do not want to mislead you.  Ah, I am
not what you think."

Tim keep his eyes on me and asked "What exactly does that mean?"

"Tim I am not a girl."  I seen the look of confusion on his face. "I mean
not technically.  I was born a boy but I never felt right as Andrew.  My
Mom and I talked it over and we decided that I was meant to be a girl.
Just over a year ago She took me to the doctor and he started me on
hormones."

To his credit Time never looked away.  The he smiled.  "There is a picture
in Jamie's room of him and a blonde guy, I was going to ask you if it was
your brother.  That is you in the picture isn't it?"

I just nodded.

"I have to ask, have you had surgery yet or do you plan on having it in the
future?"

"No Tim I have not had THE surgery yet and right now I am not really
considering it, maybe in the future.  I have talked to my Mom about having
breasts implants someday."

Tim surprised me, "Why?  I think those perky little breasts of your are
awesome.  I would not change a thing."

That made me smile and I relaxed a little.

"Why thank you.  So I take it you are not freaked out about me?" I asked.

He said no and that he still thought I was the hottest girl at the club
tonight.

I thanked him again and took a chance and gave him another kiss on the
cheek.  Tim turned his head and lightly kissed me on the lips.  before I
knew it I felt Tim slip his tongue passed my lips as he started exploring
my mouth.

We made out for several minutes until Tim broke the kiss.  "So do you still
want to hang out at my place?"

I kissed him again and said I would love to.

Tim had a really nice apartment, he had a room mate but Tim said he worked
late and they rarely seen each other.

Tim told me to have a seat as he went to and got us something to drink.
When he came back he handed me a glass of wine.

He excused himself and said he was going to change clothes and would be
right back. While Tim was gone I slipped off my bra and put it in my purse.
When Tim came back he had on a lose fitting pair of shorts.  I loved the
way his muscular legs looked.

Tim sat beside me and I snuggled up close to him, I rested my head on his
shoulder as we talked.  Tim tilted my head up toward him and started
kissing em again.  The kiss became very passionate and I felt his hand on
my right breast.

He started pinching my nipple through the thin material of my dress.  I was
moaning into his mouth as we kissed.  Tim reached behind me and untied the
top of my dress, sliding it down exposing my breasts.

Tim broke our kiss then kissed my lips lightly.  He then kissed my cheek,
my neck, he even nibbled on my ear.  I glanced down and seen the impressive
bulge in Tim's shorts.

I moved my hand to his crotch and touched it lightly, that made Tim moan.
I started rubbing his cock through his shorts as he started kissing,
licking, sucking and even biting on my sensitive nipples.

Now it was my turn to moan, I threw my head back and closed my eyes.  I was
loving the attention Tim was paying to my breasts and he sent shivers
through my body when I felt his hand starting to caress my thigh.

I stopped Tim's hand and pushed his mouth away from my nipple.  I stood up
and let my dress fall to the floor.  I stepped out of it and laid it across
the back of the couch.  Then i stepped between Tim's spread legs and leaned
down.  I blew my hot breath onto his cock and watched it jump through his
shorts.

"Baby take off your shorts, I want to see that beautiful cock." I cooed.

Tim quickly lifted his hips and slide his shorts off.  OH MY GOD, I thought
to myself.  It was only 8 inches long but big around.  It had a big
mushroom head and a red vein that ran underneath the shaft.  He squeezed
the shaft and i could see the whole cock throb.

I could not resist, I leaned down and kissed the head as he instinctively
raised his hips trying to force the head into my mouth.  I asked Tim if we
could go to his bedroom just in case his room mate came home.

Tim stripped off his T-shirt as he lead me into the bedroom.  Before I
could react he came up behind me and took me into his arms.  I was facing
away from Tim as he started kissing my neck again.  Tim reached around and
started mauling my breasts again as I felt him start grinding his cock
against my ass.

Tim was pushing me to the bed the whole time.  He pushed me face down onto
the bed.  I felt him get on the bed behind me.  I expected to feel his cock
head against my ass but was caught off guard when he pulled my panties
aside and I felt Tim start kissing my ass cheeks.

He spread my cheeks and I felt his wet warm tongue start to dart in and out
of my ass.  It felt incredible and I caught myself pushing my ass back
trying to get him to push his tongue deeper into me.

Tim started swirling his tongue inside my butt. I was grinding my little
clit against the bed and felt an orgasm starting to build.  I was
disappointed when Tim quite tongue fucking my ass.  That is when I felt his
cock pressing against my butt.  OH god the head was big and it was
stretching out my ass.

Tim let out a low growl as the head of his cock popped into me.  He slowly
pushed forward.  Tim was taking his time enjoying the feel of his cock
sliding into me.  Soon I felt Tim's pubic hair tickling my butt and knew he
was completely in me.

He stayed there letting me get use to having his cock in my ass.  When he
felt me push back against him he started slowly pulling back.  He went slow
at first and it was driving me crazy.  Suddenly Tim rammed his cock into me
and started picking up the pace.  That sent me over the edge and I emptied
my cum into my panties.

By now Tim was working at a steady but rapid pace.  He was fucking me deep
and hard and I was loving every second of it, he really knew what he was
doing.

He would fuck my ass until he was on the verge of cumming, then he would
stop and let his cock settle down, then fuck me hard again.  He was driving
me crazy.  The last time he stopped, trying to prolong it, I decided to
take things under my control and I started pushing back hard against his
cock.  I was squeezing my ass together trying to milk Tim's cock.

I knew he could not hold out forever and Tim growled and shoved the entire
length of his cock deep into my ass.  I felt blast after blast of hot cum
shooting into me and when Tim was done he collapsed on top of me.

We laid there for a long time, each of us trying to regain our strength.
Finally Tim rolled off of me and went to the bathroom, I rolled over onto
my back and was dozing when Tim climbed back onto the bed.

Before I knew it Tim had put his hands under my legs and lifted them into
the air.  He was already hard again and he had no trouble slipping his cock
back into my already used ass.  This time he was not worried about making
it last.  He started fucking me hard, deep and fast.

Tim leaned down and kissed me.  He pointed my legs straight up into the
air. As Tim worked his cock in and out of me I felt him run his hands up
and down the back of my stocking covered legs.

I heard Tim moan "Oh god I am gonna cum again!!" Instead of cumming in my
ass a second time he pulled out and shot his second load all over my tummy
and chest.  I lay there panting trying to regain my breath as Tim laid down
beside me.  I had to smile because he looked exhausted.

As Tim got sleepy and started fading in and out I slipped from the bed and
went to the bathroom and cleaned up.  When i returned and climbed back into
bed, Tim put his arm around me and pulled me close to him.
_______________________________________________________________________

Feeling Tim's hard cock throbbing in my hand brings me back to the present.
He must be having a naughty dream because as I grasp his cock it is already
rock hard.  I slowly work my hand up and down and I heard him moan as I
squeeze the head.

I could not resist, I leaned down and kissed and licked the tip.  That
brought a groan from Tim.  It dawned on me that I did not get a chance to
suck Tim's cock at all last night and I had an overwhelming urge to deep
throat all 8 inches of it right now.

I heard Tim mumble, "Oh hell" as I felt the head of his cock hit the back
of my mouth.

As he started running his fingers through my hair, I knew Tim had come wide
awake.  "Damn I thought it was just a wild dream, but I guess last night
really happened."

I just smiled up at him and continued sucking his cock.  I squeezed his
balls and was milking his cock with my lips.  Tim must have recovered from
last night because before long I was rewarded with a delicious load of cum.

Without thinking I raised up and gave Tim a deep kiss knowing he was
tasting his own cum on my lips.  He did not seem to mind as we made out
while Tim squeezed and groped my ass.

Tim pushed a finger into my ass which caused me to grind my panty covered
crotch into his cock.  Tim was a wild one as I felt his cock start to get
hard again. I sit up straddling Tim's waist.

I wiggled my butt on Tim's cock as he reached up and was squeezing my
breasts and pinching my nipples.  I got up onto my knees and reached back
spreading my ass.  I lowered my still sore ass down onto Tim's cock.  It
slide into me easily.

I started raising and lowering myself up and down his hard cock.  I was
going slowly and I guess Tim got impatient.  I felt his hands around my
waist and he started lifting me up and slamming me down onto his cock.  Oh
wow, in this position Tim was able to get his cock even deeper into my ass.

After twenty five minutes my knees and my ass was starting to hurt.  Tim
groaned and slammed me down onto his cock one more time and he came again
time in my ass.  I really liked this guys stamina.  I collapsed onto his
chest again and fell asleep.

It was almost noon when Tim woke me.  He told me to get dressed and he
would take me home.  i got out of bed and started looking for my dress and
remembered it was in the living room.

I walked out wearing only panties, garter belt and stockings to come face
to face with Tim's room mate.  Oh my, He was a tall, broad chested, well
built black man.  The room mate stood there with his mouth hanging open as
I grabbed my dress and slipped it over my head.

Tim thought both of our reactions were hilarious. When he quit laughing,
Tim introduced me to Nathan his room mate.  Nathan turned to Tim and
jokingly said "She is gorgeous, You are a God."

I found my purse and heels and asked Tim if he was ready to take me home.

Tim was quiet on the drive to my house.  when he pulled into the driveway
he commented on what a great house.  I told him that My mother worked for
the owner and she allowed us to live there.

Tim leaned over and gave me a kiss, then he told me, "Andi I had an
incredible time, but I don't want you to think I was just after sex.  I
want to get to know you better, I was wondering if you would go out with me
on a real date?"

"Oh Tim I would like that, I think it would be fun", I dug in my purse and
scribbled my cell phone number onto a card. "Call me any time."

Then I kissed Tim again.  We made out for a while and then we both decided
it was time for him to leave before we had sex right there in the driveway.
______________________________________________________________________

More to come, especially if I continue to get positive feedback.