Date: Fri, 22 Oct 2004 14:36:59 -0400 (EDT)
From: Twonight <twonight@excite.com>
Subject: World's Hottest T-Girl - Part 7

The Next Step

In my last semester of high school, I persuaded my mom to help me find a
doctor to discuss a real transition to a more feminine form.  I was tired
of having no breasts and all that body hair was a pain to keep shaved.  The
first two doctors would not even discuss a partial transition and insisted
on a very prolonged process including 3 months of therapy, 18 months of
living as a woman, then hormones and surgery.  I finally convinced the
third doctor that I didn't need therapy because I had essentially lived as
a woman, albeit a bisexual one, for a very long time.  He agreed to begin
hormone treatments and I got electrolysis for a quick solution to the hair
problem.  The breasts would have to wait a while.  My mother refused to pay
for that - she couldn't bring herself to take that step while I was still a
student.  My father had left me an education trust that would pay for an
expensive private university, but if I got scholarships, I could keep the
money.  I had already cinched over $30,000 in scholarships with my 3.9 GPA
and my 1455 SAT score, so I knew I could eventually afford the breast
implants.  What I didn't tell the doctor was that I did not intend to ever
finish the job.  My goal was to become a woman in every way except for
removing the penis.  I had to maintain a fully functional cock.

Judy and Heather noticed the changes in me before anyone else.  They loved
the softening effect, the lack of body hair, and the change in my voice.
They started dressing me and taking me to places normally reserved for
women.  I was excited to see that no one paid any attention except the men
who hit on me.  Heather was pissed when a gentlemen she had her eye on
asked me out.  I told him I was in a relationship so Heather finally got
her man.  Based on her accounts, she got her man three times, then shared
him with Judy..

My last semester, I couldn't wear dresses, but they didn't complain about
the undergarments anymore.  I still got some harassment, but that slowly
subsided.  Jaden stopped getting grief for hanging around me and he and I
continued to have the occasional roll in the hay.  Carson had not had sex
with me for months since I spent so much time with Howard and the girls.
One day I went to see Jaden, actually hoping to see my favorite lady, Jane.
Neither Jane or Jaden was home, but Carson was there, cleaning out the pool
house which had gotten some water damage in a storm.  When he saw me, he
gasped.  He couldn't believe how feminine I looked, especially with my
short skirt and a man's shirt unbuttoned and tied, exposing my sexy tummy.

He kissed me deeply and squeezed my ass, causing us both to harden down
below.  He told me that Jane and Jaden had gone to Boca Raton to help
Jane's mother move some things into a storage unit.  Carson had stayed
behind to work on the damaged pool house.  I was surprised when he told me
that he had company coming by.  He was hesitant to tell me that it was a
new male lover he had found.  I assured him that I was not jealous and was
happy that he was able to find a way to meet his needs for male sexual
contact.  He told me that he had gone to a club in South Beach, while Jane
was out of town, and had met Greg in the restroom.  They danced for a while
and things got hotter.  Greg kissed him and stroked his cock while they
danced and then went to a hotel with him for a few hours of hot sex.  I
told him I was very happy for him and assured him I would vacate before his
lover arrived.  Suddenly, he had a brainstorm.  He wanted me to watch them
while they had sex, like I had done with him and Jane.  I told him that I
didn't feel comfortable with it anymore.  Then he came up with another idea
that I did like.

When Greg arrived, I was watching from inside the main house.  He was tall,
with dark hair and a fairly muscular build.  Carson had told me that he was
28.  His ass looked great in his tight pants.  Carson hugged him and led
him inside the pool house.  I went to the pool house window and peeked
inside.  They talked briefly, then Greg undressed revealing a thick,
circumcised, six-inch cock.  Carson went down on him and adjusted their
position so I could watch him suck and he could see me watching.  He was
really working on Greg's cock, deep throating him over and over again.

Suddenly Carson, jumped up and pointed at the window, yelling something
that I couldn't hear.  He ran out and grabbed me dragging me forcefully
inside.  Greg was freaking out and Carson screamed "You little peeping tom
bitch, what do you think you're doing watching other people's private
affairs?"  Greg was scared of what Carson might do and said "Maybe we
should let the cops deal with her, Carson."

"Exactly what would I tell them Greg?  She was spying on me and my male
lover?  Are you crazy?"

"Ok, calm down Carson"

"No Greg, I think I'm going to teach this little cunt a lesson that she
won't forget."

"Carson, I won't be involved in beating up a teenage girl."

"Shut up, Greg.  I'll handle her."

Turning to me he yelled "Get on your knees, cunt."  He was very convincing
and I followed his lead.  "Unzip me and take out my cock you little whore."
He said forcefully.  I was getting hot and had to work hard to appear
scared.  "Ok" I said and pulled out his cock.  "Call me master, you little
cunt." he barked.  "Yes master" I responded, "What are you going to do to
me master?"  "I'm going to do what I please, slut, now suck my cock."  "Yes
master" I said and began to blow him tentatively.  "Take it all, cunt" he
said and grabbed my head shoving his cock down my throat.  I pretended to
gag and I could see Greg's cock beginning to harden.  Carson got on his
knees and continued to feed me his cock very forcefully.  He turned to Greg
and said "Get behind her and fuck her pussy."

He looked scared and said he couldn't do it.  Carson yelled "You do it you
cocksucker or I'll never see you again."  "Good bluff" I thought to myself
as Greg moved behind me, stroking himself.  "Lift her skirt so I can see it
go in." Carson ordered.  "Tell him you want that cock, cunt." he barked.
"Please don't look under my skirt master" I begged, trying not to laugh.
"Why not?" Greg said curiously.  "Please don't fuck me, master." I moaned
pitifully.  By now Greg was very curious and raised my skirt for a peek.
"Oh my God, Carson.  This she is a he."  "Really?" Carson asked and looked
for himself, feigning surprise at my large package.  "That's even better.
Fuck the bitch's ass" Carson said to Greg forcefully.  Greg was now hard as
a rock and slipped on a condom.  When he started fingering and lubing my
ass, I pretended that I couldn't take it.  "Please stop, master.  Don't
shove that thick cock up my tight little asshole.  I can't take it." I
begged.  By that time, he was too far gone to care and he placed the head
at my entrance and pushed.  I squeezed my muscles making it very difficult
for him to penetrate me.  It finally slipped in and he started working it
up my steamy tunnel.  I slowly stopped squeezing and he kept pushing.
Before long, I was fully mounted and he started a steady rhythmic fucking
motion sliding almost out then smoothly back in, slapping me with his
balls.

About that time, Carson yelled "Take my cockjuice you cum-swallowing
whore." and shoved his cock in to the limit spewing semen in my mouth and
throat.  I was really getting off on this scene and Greg was giving me a
great assfucking.  He held my hips firmly and "stirred" my ass with his
sweet sausage.  Then Carson surprised us by moving into a 69 position with
me.  "Clean up my cock, bitch while I taste your big clit." he ordered.  I
was happy to oblige and Greg started moaning as Carson licked my balls and
his cock.  Greg started panting and grunting as his orgasm approached.
Just before Greg blasted my ass, Carson pulled his cock out, ripped off the
condom, and took Greg's cock in his mouth.  Greg humped his face and
showered his mouth and face with thick, white semen.

Next, Carson laid me face up on a workbench he had set up and my legs and
head hung over each end.  Carson asked Greg to suck him hard again and Greg
obliged.  Then Carson rubbered up and slipped his cock in my ass to the
hilt.  Greg walked around and shoved his still-dripping cock in my mouth
and said "Suck it, boy toy:".  He was really getting into the spirit now.
I let him use my mouth as a fuckhole, milking the shaft as he fucked my
face.  They got a good rhythm going and took turns calling me "cunt",
"slut", and "whore".  It was kinky, but fun for me.

Greg pulled out suddenly and climbed on top of me, slipping a rubber on my
cock.  Then he faced me and sat on my big dick, slowly sliding down my
shaft and rocking to loosen his tight hole.  Carson had a great rear view
as he continued to pound my boycunt with his big prong.  He fondled my
balls as Greg rode my fuckstick.  I can't imagine a more sexually-charged
environment and we all were feeling it.  Greg leaned forward and forcefully
stuck his tongue in my mouth tasting the mix of his and Carson's cum that
remained.  The scene was so erotic that I started to cum.  Greg jumped up
and removed my condom and ate my cum as Carson pumped my load in his mouth
with his right hand.  Then Carson and Greg moved around and pumped their
second loads into my open mouth.

They left me on the table and sat down to rest.  Carson had another
brainstorm and used a curtain pull to tie me up with my legs spread, feet
on the floor, bent over with my stomach flat on the workbench.  He said I
would be their fuckhole for the evening and they began working on the pool
house.  They would work for a while then one or the other would see me, get
horny, and come fuck my ass.  They each fucked me twice more, then 69ed
each other to orgasm right in front of me.  I had cum twice while they
fucked me and Carson gave me one final blowjob.  It was getting late and
Greg was starting to come back to his senses, worried about what I might
say.  When Carson broke down and told him the truth, he was angry and
relieved at the same time.  He started to apologize for the harsh
treatment, but I told him it was sexy knowing that Carson would not let it
go too far.

Greg invited us both to a party being held for Gianni Versace (such a
tragic loss) the next night at someone's home in South Beach, but Carson
could not go.  I accepted eagerly and went with Greg as his date.  Elton
John was there and I got to meet him.  It was exciting as hell and the
large crowd was very eclectic.  There was great food and wine and a lot of
sexy men and women.  I went dressed as a woman and was surprised to find a
hot-looking woman goosing my ass on the terrace.  I asked her how she knew
I was a man and she said that she didn't, but that would eliminate the need
for me to wear a strap-on.  I told her that I was there with Greg and she
told me to bring him along.  I found him and told him what had happened.
He had met another sexy guy and brought him too.  The first two bedrooms we
found were occupied with other people having fun, but the second group
invited us to join them.  It was a sexy couple and things got very wild.
However the wildest part was when Julianna, the girl from the terrace, took
off her thong and revealed a gorgeous seven-inch uncut cock.  I almost came
when I saw it.  She had beautiful tits, a pretty feminine face, a hot ass,
and a beautiful cock.

The sex that night was great.  Rona, who turned out to be the only real
girl in the bedroom, ended up getting fucked in every orifice repeatedly
and she loved every minute of it.  I got my share too with every cock
finding its way into my mouth and ass.  After Rona and her date Garrett
left (both with a mouthful of cum and sore asses), the others started
passing me around taking turns reaming my ass.  I fucked Julianna once and
I loved reaching around to rub and squeeze her tits or stroke her big dick.
I came like a firehose in Greg's mouth.  We didn't leave until 2 AM and
when Greg dropped me off at home he sucked me off in the car before I got
out.  When I came, it was almost painful.  He was almost as insatiable as
me.

Graduation was almost a welcome relief.  I was accepted at a medium-sized
private school in Coral Gables that has a great football team (no more
hints).  That summer was a bit of a sexual blur.  Between Howard, Jaden,
Carson, Greg, and all of Greg's friends, I was very satisfied.  I was also
happy about staying close to home so I could continue to see my sexy
companions.  Since freshman were required to stay on campus, I was assigned
to a dorm - a male dorm.  Things got dicey immediately.  My new roomie
freaked out when he realized I was going to be living as a woman.  He asked
to have me removed and the university was at a loss as to how to handle it.
The situation was resolved quickly when another student volunteered to room
with me.  I insisted on meeting him and was pleasantly surprised to find a
very nice, attractive, seemingly intelligent senior business major (like
myself).  He was quite wealthy, coming from a well-to-do family and having
inherited a great deal of money when he turned 21.  Because he was a
senior, and school contributor, he had a special room with two separate
bedrooms, a private bath, and a small living room.

During the fraternity / sorority rush period, I was surprised to receive
two rush party invitations.  The first was from a sorority, when a member
saw me on campus and thought I was a woman.  This sorority was known for
its attractive women, so I was very flattered.  Of course I declined.  An
informal gay fraternity also approached me and I accepted their party
invitation.  I had visions of interesting fraternity parties.  When I
arrived at the party I was only mildly surprised to find that my new
roomie, Gary, was a member.  The party was a bit subdued, but everyone was
nice.  I realized that many of the members were either recently out of the
closet or firmly entrenched in public.  Most of them had had very little
sexual experience.  Also, they did not want to call attention to the small
house for fear of harassment.

The hazing was somewhat predictable, childish stuff, until the final test.
The last night, we were forced to kneel blindfolded and naked in the living
room and perform oral sex on various vegetables and fruit, then identify
it.  When we got to the obligatory cucumber, it was about ten inches long.
I heard gasps when I deep throated it and closed my mouth with it inside.
Needless to say, I was quickly a popular member of the fraternity.  That
night, back at the room, Gary told me that the cucumber stunt had raised
some eyebrows and hardened some cocks too.  I reached over and rubbed his
and asked him what he had thought of it.  He said his reaction was pretty
much like the one he was currently having, a very stiff cock.  I asked him
if he would like a private demonstration and he responded by dropping his
pants and briefs, revealing a very thick, six-inch love log.  I removed my
skirt and top, leaving me in crotchless panties and a lacy padded bra.
When I took his cock in my mouth I realized that he was not experienced.
When I finally took it all the way down, he came in my mouth almost
immediately.

"Can you teach me to do that?" he asked earnestly.  "Certainly." I said and
proceeded to give him a cocksucking lesson, with my cock being the final
exam.  He did well after a few gags and coughs and the occasional biting.
When he got the hang of it, he really got into it.  He sucked me to a
roaring orgasm, then kept it in his mouth until it hardened again and
sucked another load out of me.  I was very pleased with my roomie.  We
slept in his bed that night and I let him fuck me (another first for him).
I sucked all of his cum from the rubber, and he was riveted by that.  The
next morning we showered together and he fucked me again, then sucked me
off.

After that night, things got more interesting at the frat house.
Apparently, Gary became a convert and went forth to train others.  By the
next big party, the gang had gotten a bit more daring.  Almost every senior
and junior member invited me to a bedroom for some private time.  I took
one guy up on it and we had a grand time.  My feminine undergarments got
him so hot that he let me fuck him then cum in his mouth.  We were gone for
about an hour and a half.  When we came back to the party, several guys
were naked and in various sexual groupings.  Some of the guys got scared
and left.  One guy was on his back, getting fucked, and asked me to suck
his cock.  I slid over him and got into a 69, taking his massive meat in my
mouth.  He was, by far the largest one there - over 9 inches and quite
thick.  He reminded me of Bobby and the night in the video booth.

He sucked me well and I deep throated him over and over until he shot the
biggest load I'd ever taken.  It poured into me and ran down my chin.  This
caused the guy fucking him to explode and I got some of his load too.  I
slipped around and took his place, fucking my new friend until his cock got
hard again.  Then I slipped a condom on him and sat on his giant schlong.
It was painful, but so worth it.  When I lifted up, his giant dick rubbed
my thighs.  Before long, I shot a load on his face and chest and he caught
a few drops in his mouth.  He continued stretching my anal cavity, sliding
in and out, squeezed by my tight boycunt.  I milked his stiff shaft and
started talking dirty to him.  When I begged him to "fuck me like a cheap
whore" he suddenly exploded in ecstasy.  I milked every drop into the
condom, then slipped off and drank it.  People all over the room were
oohing and ahhing over that.  His name was Gil and I decided he was going
to be a close friend.

About once a month we had a party like that and word spread to other
schools.  We eventually had a challenge football game and party with a
similar group from Florida State and a group from the University of
Florida.  The parties quickly degenerated into major sausagefests with lots
of good fucking and sucking.  I came up with a clever way to meet everyone.
I laid on my back on a table with my head hanging off.  Then the guys
formed a line and I gave everyone a quick deep throating.  There were over
thirty guys there that night and I got a taste of them all.  Three of them
were so excited they shot a load in my mouth.  After I gave Gil a few
sucks, I told him to fuck me while I sucked the others.  While I did the
remaining cocks, Gil reamed out my ass good then fed me his cum.

When I was done sucking, the boys brought out a surprise for me - a real
girl, totally nude.  It was supposed to be a joke, but she was a real "fag
hag".  She was very attractive and had huge tits.  She sat on my face and
sucked my cock like a pro.  Then she told me to fuck her ass like I would
one of the guys.  I gave her a very sensual fucking with lots of rubbing on
her tits and ass.  She moaned continuously.  When I got close, she put my
cock between those big jugs and titfucked me to an orgasm, most of which
she got in her mouth.  I found out later that she was a hired stripper.
She gave me her card and said I could have a freebie anytime I wanted.  I
got together with her twice after that and buttfucked her both times.

If you or someone you know has been with Tess, please email me at twonight@excite.com and tell me about it.  I am very interested to compare your account with her journal entries.

Check out my fiction stories too (The Awakening, Black Dorm, Star Cruiser,
and Olympiad), and my own true story (Shocking Encounter).