Date: Mon, 3 Oct 2005 08:53:59 -0700 (PDT)
From: Jen Anders <jenanders2001@yahoo.com>
Subject: John to Jen

John to Jen by Jen Anders
jenanders2001@yahoo.com

This is a work of fiction. Any similarity to real persons, places or events
is strictly incidental.

My name is John Anderson and I wanted to tell you a little about my life
and me. When I was about 13 I started getting really interested in
girls. Only I wasn't interested in them in the same way as other boys my
age. You see I have an older sister Julie, who was 15 at the time, and was
always wearing very pretty, feminine clothes. I also have an older brother
Jim, almost 17 at the time, who always seemed to date the most beautiful
girls in school. And all I could do was envy the attention lavished on the
girls, my sister included, by my parents. I felt like a disappointment to
my folks.

The problem was that I was small and skinny and not very good at sports or
school, unlike my siblings. My parents were always going on about Jim this
and Julie that. After a while it seemed that no one even knew I was
around. In fact, most of the time I could do anything I wanted.  Especially
when Jim or Julie had something going on at school. My parents often left
me at home as I showed no interest in these activities. That's because my
favorite activity was right at home.

You see, I had discovered my sisters clothing. She and I were close enough
in size that I could wear almost all of her clothes. Whenever I was alone I
would spend as much time as possible playing dress-up in my sisters frilly
panties, bras and dresses. I cherished my private time and eventually began
to wear some of her panties to school. I even started growing my hair out
to shoulder length.

I was always very careful to keep my secret, as I knew that I would
probably be beaten up if any of the other boys found out. The bad things
about secrets, is that eventually someone finds out.  This happened in the
most predictable way. After gym class one day I was the last one back to
the locker room and saw Tim Andrews sitting in front of my locker. He said
that he mistakenly opened my locker, which is right next to his. Apparently
I had forgotten to lock it up before heading out. I was mortified! He asked
me if the panties inside were mine. I was so terrified I started to cry.
The next thing I knew he was hugging me and said, "It's ok. I understand."
He let me go and pulled open the fly on his jeans to show me his own lacy
white panties! I was stunned to say the least! The next thing I knew he was
asking if he could come over to my house after school. I was still a little
out of sorts, but agreed. He gave me one more hug and left me alone to get
dressed.

After school, we met in front of the gym for the short walk to my
house. When I got home it was empty, as usual, what with Mom and Dad still
at work and Jim at football and Julie at Theater practice. Tim and I went
up to my room and sat on the bed and talked about school for a bit.
Finally he asked, "So... do you always wear panties?"  "Not always." I
replied. "But I do it quite a lot when no one else is home. How about you?"
"Every chance I get" he said. " I also wear my Mom's dresses now and hen
but they're too big for me yet." I told him I liked wearing my sister's
clothes. He immediately wanted to try them on saying he had always admired
the way she dressed so feminine.

We were in my sister's room in a flash. I picked out my favorite, a flowery
dress she got for her 14th birthday party. Tim chose a bridesmaid dress
from my aunts wedding. It was a little longer than knee length and had a
pair of matching 3" heels. I "borrowed" a couple pair of pantyhose and a
pair of my Mom's white heels and we dashed back to my bedroom. I dressed
first and Tim helped me zip up the dress. I loved the feel of the nylon and
lace swishing against my nylon clad legs. The heels I borrowed from my Mom
fit perfect and had a sexy 4" heel. As I spun and modeled for Tim he sat
speechless. After a bit he said that had he not known it was me, he would
have thought I was a girl, a pretty one at that. I blushed and said thank
you.

Now it was his turn. The fit was a little snug, but not bad. And the shoes
were a little tight but he said it was comfortable enough. Once he was
dressed I was impressed with the way he moved in the dress. Very natural
and feminine. I suggested a little lipstick and soon we were sitting at my
Mom's dressing table primping and making kissy faces at each other. "I
wonder what it would feel like to kiss a girl?" I said. This was something
neither of us had done. Tim suggested we kiss each other. "After all, we're
both wearing lipstick so it shouldn't be much different than kissing a real
girl." Actually the thought was kind of turning me on, so I agreed, but
suggested we go back to my bedroom.

Back I my bedroom we sat on the edge of the bed and looked at each other. I
was starting to chicken out when Tim reached up and stroked my
face. Suddenly, I wanted nothing more than to kiss him. I leaned in and
gave him a little peck on the lips. The look in his eyes after that kiss
convinced me he had enjoyed it as much as I had and was and was eager for
more. Soon we were lying on the bed and making out with abandon. Our hands
were rubbing all over each other and our legs were rubbing against each
other. My cock was harder than it ever had been.  Unfortunately, we had to
get back into our boy clothes before my family got home. That night I
rubbed my little cock until I came all over myself.

Tim and I did this at least twice a week for the next few years. Though we
never went any farther than kissing. Shortly after my 16th birthday my
parents went to Europe on vacation and I came home to find my sister
sitting in my room. She asked me to come in and shut the door. Once inside
she came straight to the point. She asked me how long I had been wearing
her clothes. I denied it, of course. That's when she opened my bottom
drawer and uncovered my secret stash of panties I had stolen from her over
the years. While standing there thinking of a response she reached into her
purse and showed me some pictures she had taken of me. Apparently she had
hidden a camera in my closet. I was busted and I knew it. I blushed and
admitted to everything.  Except Tim. Then she showed me pictures of Tim and
I kissing. She was sneaky this sister of mine.

"So... why do you do it?" She asked "Are you gay?" "I don't know." I replied
"Maybe. I still like girls though. Maybe it's just that girls don't like
me. Maybe when Tim's dressed like a girl I can forget he's a boy and
pretend he's my girlfriend. Maybe I want to be someone's girlfriend. I just
don't know." Then she suggested that I dress up for her. I was skeptical
until she said that I could be her pretend little sister. So we went back
to her room and she helped me try on several of her outfits and I helped
her change into some of her sexier clothes. All this dressing up was
starting to get to me I must admit. And my sexy sister getting changed with
me in the room didn't help.  After deciding on an outfit for me, a sexy
mini-dress and heels with a matching garter, stockings and bra. She chose a
similar outfit and then sat me down at her dressing table to apply makeup
and do my hair. It didn't take very long and I was completely
unrecognizable as a boy. Only one thing was wrong. I had no tits! She
solved this by stuffing some extra pantyhose into my bra. Now we were a
couple of hot babes ready for a night out on the town, so to speak. To my
horror, I was right!

Just then the doorbell rang and Julie grabbed my hand and pulled me to the
door. She explained that her boyfriend had a cousin visiting from out of
town and had to find a date for him at the last minute. None of her friends
were available tonight and I was the only solution to her problem.  Tonight
my name was Jen and I was 18. Before I could object she opened the door and
let in her boyfriend and his cousin. Luckily Brad, her boyfriend, didn't
seem to recognize me and his cousin, Dave, was actually cute.

We were going to a local club for the night. I was terrified! All the way
to the club I didn't say a word. Once there we found a table near the dance
floor and Julie and Brad immediately hit the dance floor. After a few
minutes of total silence Dave asked if I wanted a drink. I agreed, thinking
maybe I could just get intoxicated enough to lose some of my fear. Sure
enough, after 3-4 stiff drinks I actually agreed to dance a few songs. Dave
was a good dancer and very nice, so I soon felt very at ease with him.
Then a slow song came on and as we danced I could feel his strong hands on
my back and occasionally caressing my ass. I looked up at him and as we
gazed into each other's eyes I suddenly wanted him to kiss me. He did. Very
softly and tenderly. I was hooked. All I wanted was to kiss him. He made me
feel so desired.

After the song, my sister excused us for a trip to the ladies room. Inside
she asked me if I was enjoying myself. "Absolutely!" I gushed. "Dave is so
nice and cute! Your friends really missed out." "Well, I have a favor to
ask." She said. " Brad wants to go make out in his car. Do you mind?" "No."
I said. "But what about Dave and I?" "Well, Dave wants to take you out to
the car, too. I guess he REALLY likes you." I blushed. After all, it's not
everyday a "girl" hears such a nice words.

After collecting the guys we made our way out to Brad's car and drove to a
secluded spot in the country. All the way out Dave and I kissed. I
repeatedly had to stop him from grabbing my "boobs" or trying to touch my
"pussy". I didn't want to spoil his night or mine. After we stopped I was
having a real problem with Dave's hands. Julie had a heck of a solution to
that problem. Right before my eyes she started going down on Brad! After
all the making out Dave and I had been doing he was obviously ready. His
cock was making a very large bulge in his jeans. I started rubbing it and
soon had to see this monster for myself. As I unzipped his jeans and
reached for his cock he helped out by lifting his ass and sliding them
down. I gasped when I saw it. It was at least 8" long! Mine was a measly 5"
long so his was HUGE! As I stroked it Dave moaned and pushed my head
lower. I stuck out my tongue and licked the tip. Dave gasped and I stuck
his cock in my mouth. I had never felt so slutty. I LOVED it! I began to
savor the feeling of his hard dick in my mouth. I must have done something
right. Before I knew it he was pumping up into my mouth and spraying my
throat with his hot come. It was delicious!

As I sucked the last of his come off his wilting cock I heard my sister
say, "I never knew you were so naughty, Jen! Or so good at giving head. I'm
impressed!" I blushed and said, "Thanks, I'm just a natural, I guess." "I'd
say so." agreed Dave. I kissed him and soon Brad had Julie and I home.
Luckily for me, Jim had gone to bed already, so no one saw us come home.

Back up in Julie's room Julie hugged me and thanked me for helping her out
with Dave. "No, thank you, Julie! I had so much fun tonight!" "I guess. You
and Dave were obviously getting along great." She said with a wink. "I just
wish I could've gotten off too." I said. I'm kinda sore right now, if you
know what I mean." "Oh, does Jen have a case of blue balls?" she
giggled. "Yes, I do. And now I have to go back to my room and take care of
it." "No you don't." Julie said with a grin. "She pushed me back onto the
bed and lifted my skirt. Before I knew what was happening she had my cock
out and was sucking it with abandon. She was great at sucking cock! I was
deep into having my cock sucked when a voice said, "What's going on here?"
Julie and I looked over and there was Jim!

Jim strode into the room and saw everything. Julie started crying and I
hung my head in shame, my cock deflating instantly. Jim obviously didn't
know what to say, but his body knew what it wanted. His boxers were tented
something fierce! He knelt next to Julie and hugged her while saying he
wasn't going to tell anyone. Then he looked at me and said' "What's your
name?" I lowered my eyes and said "Jen." "My, what a pretty young lady you
are, Jen. I can understand how Julie would be attracted to you. I know I
am." I was speechless! Was my own hunky brother coming on to me? He stood
up and approached me as Julie composed herself. Before I knew it Jim was
kissing me and pushing me back on to the bed. Julie having recovered her
composure undressed then helped me out of the mini-dress I was wearing. Jim
stood back to take off his boxers and Julie got into a 69 with me on the
top. As I tasted my first pussy, I felt a warm, wet sensation around my
asshole. Jim was making me feel awfully good with his probing tongue, but I
was unprepared for what came next.

After he had gotten my tight little pucker all wet and slippery I felt
something HUGE pressing at my ass. I looked around and was stunned by what
I saw. Jim was as big as I was small. Easily 9" long and 21/2 " thick. I
later found out it was 9 1/2" long. All I knew then was it wouldn't fit in
yet.  Julie said he had a solution. She went to her dresser and came back
with a slim vibrator and some KY. Jim applied some to my ass and worked the
vibrator in to my ass. I was in heaven.  Meanwhile, Julie began sucking
Jim's cock and was fingering herself like mad.

After a few minutes of this Jim decided I was ready and pulled the vibrator
from my ass. Julie applied a fresh coating of KY to his cock and guided him
in. My ass may have been loser now, but Jim was a BIG boy. I thought he'd
never get it in but then the head went in with a slight popping
sensation. I never thought he'd get any more in. He had different ideas. As
he slowly pumped back and forth he kept going deeper into my ass. Julie
crawled back under me and we resumed our 69 with abandon, although I must
admit it's rather difficult to concentrate on eating pussy when you're
getting your ass fucked and your cock sucked. Soon, Jim was pounding his
full length into me and I had abandoned all pretense of eating Julie's
pussy. It wasn't too long before I felt Jim unloading into my quivering
ass. Almost simultaneously I came in Julie's mouth.  She swallowed as much
as she could, but I had a rather large load built up from earlier that
night and she got it all. I squeezed Jim's cock with my ass, milking it for
every drop of come. When he finally slipped from my abused asshole, I could
feel his spunk running down my leg. Poor Julie still hadn't come though. I
remedied that situation soon enough by diving back into her dripping
pussy. I soon had her screaming in orgasm all over my face. We all passed
out on Julie's bed that night, snuggled up into each other.

The next morning, I woke up last and showered. When I got down stairs Jim
and Julie were talking over breakfast. I sat down and they told me that
they were wondering if I felt ok after last night. I assured them that I
felt great. I loved them both and that I really hoped we could do it
again. That's when they told me they had already made plans for me for the
next two weeks until our parents got home. They had called Tim's parents
and arranged for him to stay over for the next two weeks. I was surprised
to say the least! Then they told me we had to go shopping.  Apparently I
was to get my own clothes! What a wonderful idea! I ran upstairs and
started getting into some jeans when Jim stopped me and said that "Jen"
would be shopping today, not John. I tried to object, neither Jim, nor
Julie would hear of it.

Julie led me back into the bathroom and proceeded to cover me in hair
remover. Before I knew it I was left with only a small thin patch of hair
above my small penis and that was it. Julie then led me back to her room
and helped me into a very pretty sundress and low heels.  Then a dash of
makeup and we were ready. I was as nervous as a cat, sure that the
neighbors would recognize me in the broad daylight. No one even looked
twice.

Our first stop was the beauty salon. I was to receive a full makeover and a
perm. Not to mention a manicure and a pedicure. Soon, I was looking
absolutely fabulous! I had long nails and my shoulder length hair was
perfectly styled. I felt radiant! And none of the ladies that worked on me
ever suspected I was really a boy.  Next stop, the MALL!

I was really starting to get into this. At the mall I walked past several
boys from my school and while none of them recognized me they all gave me a
good long look with lustful eyes. We went to Victoria's Secret and I picked
out several bra and panty sets, as well as numerous nighties and other
feminine undergarments. Next were a dress shop, a trendy clothing shop and
a shoe store.  I even got a bikini! Soon I was almost overloaded with
packages and Jim's credit card was nearing its limit. Once we got home I
saw what Jim had bought while Julie and I were at the salon. He had gone to
the local porn shop and bought a strap-on for Julie some breast forms for
me and a few other goodies. Including several butt-plugs.

Julie and I decided to put on our bikinis and lay out by the pool while Jim
worked out. Julie and I had a great time, chatting like girlfriends and
giggling. I eyed her body and commented that I had always thought she was
the most beautiful girl in school. She smiled and gave me a kiss. I rolled
over and rubbed her breast as she slid her hand down the back of my suit to
play with my asshole. I was getting pretty worked up when she told me to
wait. She skipped back into the house and was soon back wearing the
strap-on Jim had bought her. It was almost as big as Jim!  It's a good
thing we had a privacy fence. She strutted over to me, pulled me up and
bent me over the picnic table. With a generous dose of baby-oil she greased
up my tender ass and was soon pushing her new "cock " into me. I moaned and
wiggled my ass to get it farther into me. Soon she was hitting bottom and
was fucking me for all she was worth. I pushed back and we soon were coming
all over ourselves.

Jim had watched the entire show and he was applauding from the
doorway. "You handle that cock like you were born with it, sis." She smiled
at the praise and said, "You look like you need some help. Gazing at his
stiff cock, I grinned and motioned for him to come over to me. Soon I had
his cock buried in my mouth and was greedily sucking his cock.  All this
sex had my young cock stiff as a board so I pulled Jim down to the deck and
got into a 69 with him. He was reluctant to suck me at first but soon got
into it. Not as good as Julie, but definitely good. A shadow fell over us
as Julie knelt between Jim's legs and rubbed baby oil into his ass. After a
weak protest from him, Julie had a couple fingers in his ass and was
loosening him up nicely. He was wiggling his ass and was ready for
more. Julie lifted his legs and I helped her slide her tool into his
willing ass. Jim gave a grunt, but otherwise made no sound until Julie was
completely in his virgin ass.  After a minute for him to get used to it
Julie started a slow stroking rhythm as I resumed sucking on his raging
hard-on. He apparently really got into it because he started sucking me
with abandon. I didn't last long and he and I came within seconds of each
other. I couldn't drink it all and it started leaking out of my lips. I
saved some for Julie as we kissed. Julie pulled her sloppy dildo out of his
twitching ass. He looked well satisfied with my come on his lips and his
leftover cum dripping down his shaft. Julie quickly cleaned this up and
shared it with Jim.

Now we had to hurry and get ready, Tim would be here soon. Julie and I went
upstairs to fix ourselves up while Jim took a shower. I put on a sexy pair
of skintight hip huggers with a halter- top that showed a little tummy with
a pair of high-heeled sandals and Julie wore a slinky little mini-dress
with a pair of 4" heels. Jim was dressed in khakis and a polo. All of us
then put in butt plugs in anticipation of the fun we might have that night.

Tim showed up at 7pm and I was upstairs waiting for the proper moment to
re-introduce myself as Jen. Jim let Tim in and said I'd be down in a minute
and that dinner was almost ready. Tim asked where my parents were and Jim
lied and said they were out for a bit, but would be back.  Not really a
lie, but not really the truth. Julie came in and Tim commented on her
outfit. She said she had a night out planned but it wouldn't start for a
while yet. That was my cue. I came down the stairs as gracefully as I could
and almost laughed when I saw the look on Tim's face. Boy, was he
surprised! I walked over and kissed him deeply. And explained that both Jim
and Julie knew our secret and were cool with it. Jim then pulled out my
chair for me, Julie and Tim. Tim was obviously still a little uneasy with
it and didn't say much all through dinner. After dinner Julie and I took
Tim upstairs and began his transformation into "Tina".

Julie helped him with the hair removal just as she had done for me, and
then the makeup. Since Tim's hair wasn't long enough for styling we used
one of my Mom's wigs. I then helped him into the outfit I bought just for
him that day. A short skirt and a silk blouse with a matching garter, panty
and bra set. Once he was dressed he was stunning. I kissed him and told him
he was beautiful and that we had one more surprise for him.  That's when
Jim came in and asked if his date was ready. Tim stammered that he couldn't
possibly go out but then the doorbell rang. Brad and Dave had just arrived!
We all piled into my parents Lexus and went to the same club I had gone to
the night before. I knew what "Tina" was going through and squeezed her
hand. She smiled at me and then we were at the club. After a round of
drinks all of us went out dancing.  Dave said I looked even sexier than the
previous night. It's nice to be adored. He smiled and pulled me close. I
looked over at Tina and she wasn't comfortable yet, but was doing all
right.  After a few more drinks a slow song came on and Jim and Tina
followed us out on to the dance floor. Jim pulled Tina into his arms and
she leaned right in to him. The next time I looked over, Jim was kissing
her and she was obviously enjoying it. All of us girls then went to ladies
room to "freshen up". Once inside I mentioned that Tina seemed to be
enjoying herself. She said, "I am! I can't believe I'm out on a date with a
cute guy like your brother!" "Just wait," I said, "The fun is just
starting."

Once we got back to the guys we all decided to head home. Julie and I were
busy making out with our dates, but decided not to invite them in. After we
all got inside. I led the other girls upstairs to get into something more
comfortable. Jim meanwhile had poured some wine and brought it upstairs to
the bedroom. By the time we got to the bedroom he was already in the bed
waiting for us. Julie went to get some toys and Tina and I got in bed and
started making out. Jim started kissing Tina and I kissed my way down to
her cock. It was long and stiff and I sucked on it greedily. I soon worked
her into a 69 and she got into sucking my cock as much as I was into
hers. Julie had come back by then and had already donned her strap-on. She
climbed behind me and lubed me up. Then handed the KY to Jim. And he
prepared Tina by working the lube into her ass. She moaned around my cock
and soon had Jim's cock pushing into her ass. I had Julie fucking me in a
steady rhythm and Jim was almost completely buried in Tina. Soon we were
all getting into a good fuckfest. Before I knew it both Tina and I were
spraying our loads across each other's faces. We spent the rest of the
night fucking and sucking in every possible position and everyone ended up
sleeping in a pile on my parent's bed. We kept this up for the next two
weeks with Tina and I becoming more feminine every day.

I lived a double life for the next 2 years until I graduated and could move
out on my own. Tim moved in with me and we live as women full time. We have
many boyfriends, but always make room for Jim and Julie when they want to
visit.