Date: Thu, 1 Nov 2007 19:27:13 GMT
From: "teresawood1@juno.com" <teresawood1@juno.com>
Subject: A Tragic Beginning (A TG story submission)

A Tragic Beginning
by: Teresa Ann Wood

Of course I felt guilty; the opportunity of a lifetime had come to me and
even if it turned out to be better than even my wildest dreams that wasn't
the way I had wanted it to happen. I never wanted to profit from someone
else's tragedy.

My name is Josh Benning and I have been a closet crossdresser for most of
my young life; living out of the clothes hamper of my female relations and
those of my few friends. I was never caught, not once, in all those years
of dressing up but that was mainly because I was so cautious. I never once
left the bathroom, not even when I knew that I was home alone. I was a
coward but with good reason; I'd seen what my father did when my older
siblings broke his rules and none of them had ever done anything that would
be as bad in my father's eyes as a boy wearing girl's clothing. I wanted to
dress up, but I wanted to live too.

Anyway I kept my secret all the way through high school and did my best to
live a `normal' life in public. I asked out some girls only to be turned
down as I was small and apparently completely unattractive to them. I
didn't know why their negative responses were such a relief to me. I
thought that I was just scared of going on that first date; I wouldn't know
what to do, how to act, but it reality I just didn't want to date a
woman. Even then I was gay; I just hadn't admitted it to myself.

My family was poor but I had good enough grades to earn a scholarship to an
in-state college. It wasn't a huge school with tens of thousands of
students, but it had enough to maintain most of the major sports teams like
football, basketball, baseball, and even soccer. They offered sports
scholarships but most were not full scholarships; leaving most of the
students to come from very wealthy families. They had a gymnastics team,
the only sport I could compete at, and so I had intentions of trying out
for it when I got there. My dad wasn't crazy about it but he was mollified
that his `sissy' son was at least going to be competing in a college
sport. None of my behemoth brothers had accomplished that.

So off I went, moving from my small rural high school to a community that
was just barely large enough to qualify as a city. Lendersville had a
population of around 35,000 people, most of which had jobs that were at
least indirectly reliant on Lender College. It was a college town, that's
for sure, and all incoming freshmen were made to feel right at home. I
certainly was, at least until I met my roommate.

Trent was a conceited jerk, no question about it. In his heart he knew that
he was incredibly handsome and the wet dreams of every young woman he
met. He was an athlete at Lendersville on a basketball scholarship. At
six-foot-three he may have been tall for a point guard, but his
ball-handling skills were superb. He had offers from bigger schools but
chose Lender College because his family had some sort of legacy there;
every one from their family had attended Lender for a hundred or more
years, apparently. Trent wasn't necessarily a cruel guy, but he realized
right away that he was the dominant male between us and he simply expected
me to do what he said. The worst part of the whole situation was that Trent
was every bit as dreamy as he believed, and for the first time I could not
deny my attraction to another man. He was mouth-wateringly gorgeous!

As I was planning on trying out for the gymnastics team, I had to arrive at
school several weeks early. Trent was already there and before the first
week was up I was the one responsible for cleaning our dorm room. I tried
to make the best of it and would try to do it when he was gone, so I could
slip on a pair of panties (the only female attire I owned and all I dared
to keep with me) beneath my regular clothes and pretended to be a woman
cleaning the room for myself and my boyfriend (I had it so bad for
Trent). I really enjoyed picking up his dirty clothing, particularly his
jockstraps, and before long I was doing both our laundry too. In some ways
I didn't mind too much but in others I did; but one peek at his
half-clothed body would drive that away. Just about anything was acceptable
if it kept us living together; he was so hot! Before long I found myself
masturbating daily thinking of him, but unfortunately had never had a
chance to catch a peek at his cock. I couldn't take the chance that he
might catch me looking.

Anyway I went out for the gymnastics team, just like I planned. I worked
hard for three weeks but in the end I was the last one cut; I had the
ability, the coach said, I just didn't have the experience of the other
guys. This was devastating to me since I had really wanted to make the
team; not only did I want my father to be proud of me (I'm not sure why)
but since Trent had convinced me that I was, in fact, truly gay, I enjoyed
the sight of the other male gymnasts dressing or showering after practice.
This led to another epiphany for me; I was pitifully endowed.

My dick is tiny, no question. I knew it was smaller than average from some
`research' I had done on the internet but I had convinced myself that those
men were on there because they were so much larger than normal. Perhaps
they were, but even average is apparently far bigger than me. I've begun to
think of my dick as `the smallest in captivity', as even at full erection I
can easily jack-off with two fingers. None of the other gymnasts could
match the monsters of the internet, but then again even the smallest of
them made an easy three of me. I made sure they didn't see mine even as I
took cautious peeks at theirs.

Needless to say I was really downhearted about not making the team, and
dreaded having to tell my parents as I knew my dad wouldn't take it well. I
didn't have to worry about that, because by the time I went home that next
week to break the news; he had died of a massive heart attack. This was
devastating to my whole family, even to me; my dad and I didn't always get
along but I knew he only wanted what was best for me in his eyes. Our
determination of what was best simply varied too much. He had loved me in
his own way, I know that.

I returned to school right after the funeral not because I had to, classes
still didn't start for a long time, but because I wanted to. Home was too
depressing, particularly with mom grieving like she was, and I wanted to
get back to Trent. Not that he had missed me; he only knew I had been gone
because the room hadn't been cleaned; his days were filled with pickup
basketball games and chasing various unattached women. Once I had told him
about my dad, however, he became nicer to me and listened as I talked about
my grief. It's amazing what will strike a cord within someone. His own
father had died not long before, and that was part of the reason he had
came to Lender. He comforted me that first night, not in his arms like I
wanted, of course, but we talked most of the night. I loved him all the
more for it.

One positive side of my father's death was that I no longer had to worry
quite so much about doing some things that I wanted to; such as letting my
hair grow. I had let it grow as much as he would allow before leaving for
college and hadn't touched it since I got here. I was intending to cut it
before going home but his death caused me to forget. Now I wouldn't have to
cut it if I didn't want to; mom wouldn't care. It grew pretty quickly
anyway and so I hoped that by the New Year it would be long enough to reach
my shoulders. It was a secret dream of mine to have hair long enough to
wear in a ponytail. Certainly it was a feminine hairstyle and yet I could
get away with wearing it in public! For me, that was a very brave plan. Who
knew if I would ever have the guts to go through with it but I could at
least let it grow for awhile to feed the dream. Another positive aspect
came a day or two later when I read a notice concerning cheerleader
tryouts. There were no scholarships for the cheerleaders so the tryouts
were completely open. My heart almost stopped when I realized that I could
tryout for the cheerleading squad.

What was stopping me? My dad was gone, he would never have allowed that,
and in college there were male cheerleaders all the time. It didn't carry
nearly the stigma that male high school cheerleaders did. Not that my high
school would have ever have allowed such a thing. Perhaps I couldn't make
the gymnastic squad, but those same skills just might get me onto the
cheerleading squad! Tentatively I mentioned my idea to Trent, who thought
it was a great idea.

"You get to look up the cheerleader's skirts all the time; and they sit
right on the palm of your hand when you lift them up in the air," He
chortled. "I would love to be a male cheerleader; they're bound to get laid
all the time if they're not all queer."

Trent's comments emboldened me even as I worried that they were hitting too
close to home considering the `queer' comment. He had given me an obvious
excuse as to why I wanted to be a cheerleader but even so I was amazed that
I had the guts to even consider it. Despite telling myself that I would
never go through with it and that it was simply a nice little dream to play
around with I found myself in the gymnasium on the first day of tryouts.

I was surprised to see fourteen guys trying out for the four open spots on
the squad. There were twice that many girls trying out for only three
openings on the girl's side. At least half the guys were there for the same
reasons that Trent had given; they just wanted to get their hands on the
girls and so they were quickly weeded out. My tumbling skills got me
invited back for the second day but by then it was obvious to me that I
simply did not have the strength to do what they needed. I had to be able
to lift the females and hold them over my head; it was they who needed the
gymnastic skills not the men. Somehow I was invited back the third day with
four other guys; I had an eighty percent chance of making it, but at the
end of that day the cheerleading coach took me aside and gave me the bad
news; I had been cut.

"We'll keep your name on file, though," she said, patting me on the
shoulder. "If we have an injury we might use you to fill in for the
alternate we activate."

Great. I couldn't even make it as a full-time alternate. I thanked her and
gathered my stuff, delaying as much as possible in the hopes that the other
male cheerleaders would come in to shower once more before I left, but I
was disappointed in that regard. Most of them were gay just like Trent had
joked but for whatever reason those guys didn't really appeal to me. Not
like Trent or the other straight guys did, anyway. When I looked at him, I
was immediately aroused. When I looked at the obviously feminine-acting gay
men I felt absolutely nothing. At least with women I had some interest in
what they were wearing.

I sulked as I left the locker room; apparently college was to be no more
successful for me than high school had been, at least not outside the
classroom. Most of the gymnasium we had been working out in was empty, the
door to the track stood open so they must have been outside running but I
noticed one figure sitting near the top of the bleachers on one side. The
noise from outside was too loud for me to hear anything but I could tell by
the way she was sitting that she was crying. Without thinking too much
about it I made my way up the steps to her, approaching quietly so as not
to frighten her. That was almost funny to me; no girl was ever frightened
of me; I'm smaller than them more often than not. I sat nearby but not
threateningly close. I wanted to help but if she didn't want to speak to me
then I would leave.

I recognized her of course; she had been trying out for the cheerleading
squad as well, though they had scrupulously kept the men and women apart
during most of the tryouts to discourage the horn-dogs that were there just
to get a peek up a few skirts. She was quite pretty with red hair and a
petite build; she was barely taller than me which was saying something. She
had a nice, athletic body and I had thought that she was a shoo-in for the
squad. I guess that showed how much I knew. I sat for awhile and was just
about to leave when she finally spoke.

"I guess you were cut too," she sobbed, never once lifting her face from
her hands.

I said that I had been and tried to ask her the same question but of course
it came out all messed up. Thankfully she was merciful and didn't take me
the wrong way.

"Yes, and it's not fair! I deserved to make the squad!" she grouched,
finally lifting her face and looking at me, daring me to disagree, I
supposed.

"I totally agree, you were great," I said quickly, not wanting to have
`beaten-up-by-a-cheerleader' attached to my already weak reputation.

Mollified she calmed down a bit and we began to talk about the unfairness
of her plight. I really did agree; she was easily as good at cheerleading
as any of the girls that made the squad, and so she found some comfort in
my presence. I actually felt better about my own failure as well, just by
helping her. That seemed odd to me at the time but I understand it now.

"Do you know why she cut me?" the girl, her name was Debi, demanded at one
point. I said no. "Because she's a lesbian and she only wants girls with
big boobs!" she explained, tugging her t-shirt tightly to her body to
expose the outline of her breasts. "Do you see anything wrong with these?"
she demanded again, glaring at me as if daring me to say that I did. She
certainly had the temper to match that hair.

I dutifully looked at the small mounds on her chest, noting that they were
likely B-cup unless her clearly visible sports bra was messing with my
judgment. Certainly not huge breast but I would love to have them myself.

"No, of course not, they're great," I stumbled, looking away from her chest
in embarrassment. Had I really thought that I would like to have breasts
like hers? "But how do you know that's why she cut you?"

Debi laughed once, very sharply. "It's a well-known fact that she's a
lesbian. She was almost fired two years ago for dating one of her
cheerleaders.  This is my fourth time trying out, and I've been the last
one cut every year. Now I'm a senior, and this was my last chance. It's so
obvious that she only wants girls with big tits on her squad; if you pay
attention to the ones who make the team you'll see what I mean..." she
hesitated, looking a little closer at me.

She suddenly moved closer on the bench, staring intently at me. Not in a
threatening way but just very intent. Catching my eyes she also caught my
own gaze; I was staring eye to eye at her without the least ability to look
away. She was looking into my soul, that's how I see it now, but then it
was very disturbing to say the least. Even in her sorrow she wanted to help
me in return.

"You're gay, aren't you." She stated matter-of-fact. My gaze was still
captured by hers and I was the only one of us who was surprised to hear my
voice say that I was. Perhaps some people might have suspected but no one
actually knew. I was mortified over what I had just done!

"Don't worry, I'm not making fun of you," she said quickly as she scooted
even closer to me on the bench-style bleachers. "I know it had to be tough
on you to be cut as well. I can imagine how much you were looking forward
to showering with all those cute guys."

She was teasing me, and for the first time in a life filled with teasing it
didn't hurt; it even felt good. Tearing up myself I shared a little laugh
with her and within an hour we were the best of friends.

We spent the next several hours drinking coffee at a little diner and then
went back to her dorm until I and any other men visiting had to leave. Then
we walked for a while around campus just talking; it was a wonderful
evening and completely new to me. I'd never had a close friend and Debi was
wonderful. We talked of our disappointments and I talked of being gay and a
virgin. She told me about her past boyfriends and her desire to be a
cheerleader. Debi promised not to tell anyone about my being gay and for
the first time in my life I was able to unburden myself completely. By the
time I went back to my own dorm she knew everything there was to know about
me; even my desire to crossdress. We agreed to meet for lunch the next day
and I could barely sleep I was so excited. Scared and excited. I had told
her everything, all my secrets, and if she had been playing me for a fool
everyone one campus would soon know. By the time I drifted off to sleep I
was frantic with worry. How could I have been so stupid?

But she met me for lunch just like she promised and within minutes I knew
that she hadn't told anyone about my secrets. Indeed I felt that she would
never betray me that way and by the time we finished lunch it was almost
time for dinner and she had shared such intimate details of her own private
life that I knew that my secrets would always be safe with her. Whenever we
were alone she started calling me `Jill' but never forgot to call me `Josh'
when someone else could overhear.

After dinner we went back to her dorm again, her roommate had not yet
arrived for fall classes, and she showed me a smooth plastic dildo she kept
locked in her makeup case. She told me about her sexual encounters and
confessed that she used the dildo `more often than she had to' because she
had never had trouble getting a boyfriend. She told me about giving head,
she didn't enjoy it but had done it a few times for guys she really liked,
and told me how wonderful it felt to have her pussy stretched wide by a
nice, thick cock and feeling it rubbing against her clit. Naturally this
sort of talk turned us both on and after sharing these sort of intimate
conversations all that next week it seemed only natural for her to use the
dildo on herself in front of me as she explained what felt the best. By the
third or fourth time I was even helping her; working the dildo in and out
while she played with her clit or cupped her breasts. Sitting through these
sessions without even getting hard was the last straw as far as removing my
last denial about being gay. I never got excited until she offered to let
me try her dildo for myself.

Scared, embarrassed, and surprised, I declined her offer but she wanted to
do something for me and so the week before her roommate arrived she finally
convinced me to allow her to dress me up completely as a woman; makeup and
all, just so I could get the full experience. I was so nervous I almost
passed out but I showed up when she told me to, fully shaved from eyebrows
to toes, and enjoyed a glorious evening trying on her clothes. We were very
nearly the same size, even her bras fit me perfectly though I couldn't fill
the cups, and I must have tried on every outfit she had twice over. I
adored her stockings and when I left that night she insisted that I wear a
pair of pantyhose home `just to get used to them,' she giggled. We did this
every evening until her roommate arrived and I graduated to wearing her
panties full-time. Not easy to keep out of Trent's sight but I managed it
well enough. That last weekend we went shopping together, me dressed as a
man except for my panties, and she bought a lot of clothing for me as her
family was wealthy and she had her own charge cards. She kept the clothes
in her dorm for me but with her roommate due to arrive soon we both knew
that my dressing opportunities would soon end. That was when she got the
news.

Lender College had a mascot, like all colleges I guess, and ours was a
Puma. It was a big, angry looking feline with a trademark LC ball cap on
its head. Naturally images of it were everywhere on campus, complete with
such statements as `Puma Pride' and `Go Pumas'. Debi's roommate had arrived
and classes were only a day or two away from starting when Ms. Chlebowski
came to see Debi and offer her a place on the squad. She wasn't nearly as
excited as I thought that she would be.

"The mascot?" she grouched. "I don't want to wear that stuffy old costume,
that's not real cheerleading!"

"Yes it is," I argued, sipping at my coffee. The diner had become our
regular hangout now that her roommate was there. "It may not be the same as
having some guy's hand up your butt all day but you're still cheering your
team on to victory!"

That at least made her giggle and eventually she accepted the position. It
certainly wasn't her dream but finally she agreed that it might be fun but
only if I agreed to attend every game that she did. I agreed, what else did
I have to do? Study and watch her was about it. I still had no social life
that didn't involve her. Trent thought we were dating as it was.

So Debi became the new Lender College mascot, dressing up in that ratty old
puma costume and practicing for hours each day as `Lendy'. Fall classes
began in mid September but the first football game was more than a week
before that. She had to attend all the home games for football, basketball
and soccer for both the men's and women's programs and had to at least make
three appearances each for softball and baseball in the spring. That was
far more than the regular cheerleading squad had to do, as they were only
required to attend home games for football and basketball plus their own
`cheer' tournaments. Being such a small university, we didn't have varsity
and JV cheer squads, nor a pep squad and the like to handle all the
sporting events, and only one mascot suit as well. By halftime of that
first football game, we lost something like 37-17; I knew that Debi enjoyed
being Lendy a great deal.

Now Debi had more demands on her time but she still made room for me. I
came over and helped her with her homework, even though she was a senior
and I was a freshman, I was a better student that she was. I didn't always
know as much about her subjects but my research skills were
impeccable. Whenever her roommate Abby would leave on a date Debi and I
would talk about men and clothes. She agreed that Trent was a total cutie,
and she would always offer to dress me up. I wouldn't, afraid that Abby
would return unexpectedly, but Debi would still find ways to help me by
practicing her own makeup skills while I watched and asked questions. She
would also insist that I wear the `proper' underwear while visiting,
helping me put on a bra to go with the panties I always wore now. Feeling
that sweet tightness across my chest while Debi and I talked about the
cuter guys on campus is one of my fondest memories. She would occasionally
urge me to `come out' and offered to introduce me to some other gay friends
but I always refused. At heart, I was still just too much of a coward
despite the thrills these conversations gave me.

My life became very busy as well now that classes were in full swing and I
still had to keep my dorm room clean while doing mine and Trent's laundry
(I always thought of it as `our' laundry) along with most of his homework
with my own as well as being there for all Debi's appearances as Lendy and
visiting her as often as possible. Debi only came over to my dorm a couple
of times but decided to stop when Trent started hitting on her. She said
that while he was hot she would never steal a man away from one of her
girlfriends. Debi always knew what to say to make me happy.

Wearing that mascot costume was hard work, particularly in the fall once
football and soccer were in full swing. Neither sport had really slacked up
very much when basketball was starting up so Debi and Lendy did not make
every game, sometimes she had to prioritize, but she made a great effort at
it. Several times she had to attend multiple sporting events on the same
day and she would always come home exhausted. I was at every one that I
could be at and gave her long massages afterwards to ease the cramps in her
muscles. Obviously she was in great shape to maintain that sort of activity
and I enjoyed rubbing the kinks from the muscles of her nude body.

I always wore a minimum of panties and bra when I did so and it was fun and
easy to pretend that I was her girlfriend. If Abby wasn't around I would
sometimes use Debi's dildo on her, she didn't have much time for dating,
and by now I knew just exactly how to tease her clitoris to ensure that she
had a good orgasm. She would occasionally again offer the dildo to me for
my own use but I continued to refuse. Not even when she offered to do me by
hand would I agree to masturbate in front of her. I was both ashamed at my
smallness and by the fact that I wasn't a woman like her but she persisted
until the weekend before thanksgiving when she caught me in a truly
vulnerable moment.

Abby had gone home for the weekend, so I had allowed myself to be dressed
completely for the first time since the semester began. I was in heaven as
Debi and I sat together, giggling over boys and trying on various dresses
and outfits. I should have realized that something was up when Debi pulled
out a stack of brand-new magazines, bought just for me and that occasion I
later found out, that were dominated by pictures of nude, handsome men. Two
were recent issues of Playgirl and two others were Club magazine. The
Playgirls were nice, the men were certainly hot, but their cocks were
always soft. They stirred the imagination but didn't really turn me on as
much as the other mags did. The Clubs were primarily full of naked women
but there was one blazing hot pictorial in each that featured a woman or
women with a rock-hard stud busily working to fill their mouths and
snatches. I was mesmerized by the pictures, just as Debi planned, and when
she started making her offers I soon gave in.

Lying back on her bed she had me hold the magazine open to a particularly
torrid picture showing a tight close up of an amazingly large and erect
cock. To either side were the lips of two women, their tongues plastered to
the sides of that beautiful dick, captured in mid-lick. Debi handed me her
dildo, insisting that I kiss and lick it while imagining that at least one
pair of those lips licking that magnificent cock were indeed mine. Lifting
my skirt, Debi talked about how wonderful the guys said that I was at
sucking cock, particularly Trent who had told Debi that I, Jill, was the
best cocksucker he had ever known. All patently false but the fantasy
worked like a charm and she barely had to squeeze my miniature cock through
my panties twice before I erupted in the best orgasm I had ever had.

That night was amazing. Debi convinced me to hide in her closet when the
dorm monitor checked the room and then I spent the night in bed with her
dressed in her sexiest nightgown. I used the dildo on her twice, I even
licked her clit although I really didn't enjoy it, but she said that I
could pretend that it was a little bitty cock. That didn't really work but
I didn't mind doing it for her. She jacked me off twice more by morning and
I was amazingly happy all the next day despite being exhausted. Debi added
to my happiness by convincing me to wear a complete set of women's
underwear beneath my clothing; a girdle, slip and stockings to compliment
my usual bra and panties. She explained that since I didn't have classes on
a Saturday and it was cold enough to wear a thick jacket that no one would
ever know. They didn't, but I did, and I was both frightened and
exhilarated all day. I didn't dare go back to my room dressed that way, but
otherwise it was fantastic. When I did get back that evening after changing
into a more modest pair of only panties beneath my jeans, even Trent
commented that I seemed to be in a better mood than usual.

As the semester wound down the football and soccer seasons ended, we didn't
have a winning record and so no post season in either sport, leaving only
basketball still going on. Trent and the men's team were doing fairly well,
they had at least won more than they had lost, but the women's team was
something like 0-12 going into conference play. Debi had gone to the
football homecoming with a football stud named Darren and had continued to
date him through December. I was more than a little jealous but then she
gave me a picture of his cock at full staff and I forgave her. It was
really nice and I certainly couldn't deny her that kind of pleasure. I hid
the picture well, but I couldn't help taking it out when I was alone and
pretending that it was Trent. Everyone was preparing to go home for
Christmas break when the tragedy struck.

It was a typical college party; too much drinking and a bunch of people too
young to handle it. Darren and Debi had double-dated with Abby and her
latest boyfriend, she was a real slut it seemed, and Darren had drunk
entirely too much alcohol. Abby called me from the hospital, babbling about
Darren driving like a crazy man and hitting a tree. Debi was the only one
who died.

The campus mourned, of course, but not like I did. I called home and told
mom what had happened, she knew about my close friendship with Debi and
likely believed that we were dating. I told her that I wouldn't be coming
home for Christmas; I really needed to stay here and sort out my
feelings. She gave me no problems about it and I just lay sulking in my
room for the first several days. When the dean of the college asked me to
box up Debi's things to send home, I couldn't say no.

Abby had taken Debi's death hard as well, and had not only gone home but
withdrew from Lender College as well. They had roomed together for four
years and done a lot of crazy things together. She had packed a few things
but had left a lot of her stuff behind, and all of Debi's remained where
she had left it. Naturally I couldn't very well send home everything;
Debi's dildo for instance, nor the magazines that she had really bought for
me, so I was careful about what I packed. I was about halfway through and
starting to look through Abby's stuff when I found a letter from Debi's
parents. They asked that Abby send a few specific things home to them and
then donate all the rest of Debi's things to whatever charity she
wished. They were too distraught to handle very much and wanted only a few
cherished keepsakes. Unsure what to do I continued to pack up everything in
the room, including the clothes that really belonged to me, and simply
stacked them up in the closets. I mailed the things that Debi's parents
wanted but the rest I left in the boxes. I had no idea who to donate them
to and wasn't sure that I wanted to. The dean said that he understood the
problem, or at least thought that he did, and that I shouldn't be in any
real hurry to get rid of the clothes. I had until the next fall to find a
suitable charity to donate them to as the dorm room would remain open until
then. The hardest part of the whole process was finding a present addressed
to me on Debi's top shelf. I very nearly lost it then.

I stopped wearing panties for a while. It was just too painful because all
that I had had been given to me by Debi. I sulked around for days, spending
all my time in Debi's room, just lying on her bed and crying. When Trent
came back after the holiday, he found me there. He sat beside me on the bed
and even put his arm around my shoulders. I leaned into him and cried some
more; not even turned on by his touch I was so miserable. After crying for
what seemed hours, I realized that I had unconsciously wrapped my arms
around his waist as I wept; but he hadn't said anything. What a wonderful
guy he could be at times.

When classes started up again I had developed a new routine; I now spent
most of my free time in Debi's dorm room. No one bothered me; the girls
there simply looked on me with sympathy as I mourned. They didn't knock on
my door, they didn't throw me out at night, I almost lived there. Once each
day I would go back to my old room and do a quick clean up, washing mine
and Trent's laundry as always but I never stayed for long. Eventually I
decided to unpack a few things at Debi's, and put everything back where it
belonged and also began wearing panties again; while folding them and
putting them away the urge had simply became too much for me. I knew Debi
would want me to have the clothes and Abby apparently didn't want any of
hers either. Finally, about the second week of January, I opened my present
from Debi.

Breast forms. They were as realistic as could be with nipples and an
adhesive to attach them to my chest. They were `B' cup, the same as Debi. I
cried again all night.

The next night I dressed completely for the first time since Debi's
death. It was sort of a celebration of Debi's love for me. My new breast
forms completed my look and I began to realize just how much I looked like
a real woman when dressed. In honor of Debi I took out the magazines and
her dildo and, with the help of a tube of lube she had, I slid it into my
backside for the first time.

What can I say? Flashes of light burst in my brain after I got past the
initial discomfort. Staring at that same cock picture and pretending it was
Trent that was sliding in and out of my `pussy' caused me to come as I
never had before. I had been born with only one testicle and rarely did
anything come out when I masturbated but that night must have been really
special, because I left a large stain on the front of my blue silk
panties. I lay there on Debi's pink comforter and shook through two orgasms
before taking the dildo back out for cleaning. I needed no more urging
after that; I was hooked!

It was the very next day that my life changed again; at least it was for
the better. The cheerleaders had gotten together and demanded that I be
Debi's replacement inside Lendy. Ms. Chlebowski wanted another female to
wear it but all the cheerleaders were aware of how close me and Debi were,
so they thought that it was fitting. Everyone knew that I had been the last
person cut from the male side of the cheerleading tryouts, so I was
obviously qualified. I was reluctant to accept, but the thought of a
complete stranger wearing the costume was simply too much; and so I agreed.

The girl's basketball team had a game in a few days, so I had to go to a
couple of cheerleading practices and convince everyone that I had the
routines down. No one was surprised that I did as they had all become
accustomed to seeing me there watching Debi do them. One surprise I had was
where I had to dress; in years past the person wearing Lendy had sometimes
been a male and sometimes female, so there was a separate locker room just
for whoever was wearing the costume. Debi hadn't mentioned that. I was
shown to the small room by one of the other cheerleaders and once I had
shut the door found myself facing a large locker fronted by a wooden
bench. Inside the locker was Lendy.

It was rough, I tell you. I shed yet a few more tears for my dear friend as
I stared at the head of that fake puma. One of the custodians had cut the
lock off for me so that I could get to the costume and when I finally
managed to pull it out I was surprised to see what was hanging behind it.

It was Debi's cheerleading uniform, given to her when she made the team as
Lendy. She had never gotten to wear it but had kept it nonetheless. Perhaps
she had worn it underneath the costume. Perhaps not. She had told me just
how warm it could be in there. Hands shaking I removed it from the locker
and hung it nearby. Further exploration of the locker allowed me to
discover a small bag containing makeup and things for the shower. The
locker room had a private one of those. A clean towel was discovered in a
gym bag at the bottom along with a pair of white silk panties, a sports
bra, a pair of white socks and some pink tennis shoes.

I put everything back except the costume but by the time that the next game
rolled around, the thought of that cheerleading outfit simply would not
leave my mind. Arriving well before game time I locked myself in my little
closet and then stripped completely, utilizing the single shower to shave
away the stubble of my body hair using Debi's toiletries. I even used some
of her perfume, figuring anyone that smelled it would think that it was
simply clinging to Lendy from earlier uses. Afterwards I sat shivering on
that cold wooden bench and stared at the outfit, wondering just how
wonderful it would feel to wear it.

Debi had never brought it back to her dorm, so I had never gotten to try it
on. I was certain that it would fit me; all of her clothing did, but wasn't
certain if I should or not. Finally I convinced myself that it would be ok
to try it on, Debi wouldn't mind, but there was no way that I could dare
wear it out of the room; not even under the costume. Hurrying now so that I
could try it on before having to change for the game, I slipped on the
panties she had in her gym bag along with the bra. I had my breasts forms
with me, a hint that my subconscious had already made the decision even if
I didn't realize it yet, and soon I was sliding that glorious garment onto
my body. Grateful for the room's mirror, I admired myself for a long time;
my shaved legs looked fantastic beneath the short skirt and my breasts
forms pushed out the top quite convincingly. With my hair back in my
fantasy pony tail (it was short but doable) I looked and felt more feminine
than ever before. My pleasure was almost orgasmic!

Telling myself that I would try on the costume over the outfit just to see
how hot that it indeed was, I didn't even hesitate once the head was in
place but marched confidently out of the locker room towards the gym. No
one would ever know what I was wearing beneath the costume and even if I
took the head off during a break no one could see anything below my
neck. It was perfect!

I sounded really brave but believe you me I was scared to death when I ran
out with the other cheerleaders. I just knew that everyone in the stands
knew what I was wearing beneath that fake puma fur. Somehow I managed to
get through the game, I think we won but I'm not certain because of
something that happened just before halftime that truly blew my mind. We
were doing the `Lender' cheer where the cheerleaders use their bodies to
spell out the name of our college. The mascot was the last to run onto the
floor and it was my job to be the `R'. It was while standing there being an
`R' that I happened to look towards the seat I had always sat in when
cheering for Debi. Sitting in `my' seat and smiling to melt a frigid heart
was Trent.

What was he doing here? He had never been to a girl's game before, I was
certain. Not only was he sitting there he was waving at me! Flustered
beyond belief I stumbled through the rest of the half and scampered to my
dressing room as soon as the halftime show was done. This would be my only
chance to take off the head and cool down; you weren't allowed to take it
off where any kids might see, even though there were no more than three
hundred people in the stands and probably not more than a dozen kids in the
whole gym. Just as I reached the hallway before my dressing room and
reached up to pull the head off, I heard someone calling my name.

"Josh, wait up," said Trent, trotting up behind me. "I've been yelling your
name," he said as he caught up, smiling at me in that way that I loved.

"Sorry, I guess I couldn't hear you through the head," I gushed, trying to
understand why my beautiful roommate had followed me down here, or even
came to the game for that matter. My heart was pounding as I looked up into
his baby-blues. To him I might be a scrawny boy in a fur costume but at
that moment I was imagining myself as a girl dressed in my cheerleading
outfit. For me, that fur costume had ceased to exist. I was patently aware
of every stitch of female clothing I was wearing and consciously pushed out
my pert B cups as far as possible, wishing that they were real and that he
would see me as I wanted to be.

"Yeah, I don't hear too good when I'm getting head either," he laughed. A
typical Trent joke.

Trying to be witty and return his with a cute remark of my own I blurted,
"I didn't say when I'm getting head, I said I couldn't hear when I was
giving you head..."

I was shocked into silence for only a moment before trying to fix my
error. Talk about your Freudian slips! "I meant when I was wearing the
head... the costume head I mean," I stammered, knowing that my face was
brilliantly crimson.

Trent smiled all the more. "You're not too good at those comebacks," he
laughed.

I smiled, grateful that he hadn't teased me more than he had. "What brings
you down here? I didn't think you liked watching the girl's games?" I asked
after a short and uncomfortable silence. Uncomfortable for me, anyway.

"I don't. Tall girls do nothing for me. I like `em short, about your height
is perfect."

Still blushing I filed that bit of information away for future
fantasies. "I suppose you like them big breasted too? EE's or bigger,
right?"

Again that laugh. The sight of his lips were making me weak in the
knees. How I would adore kissing them!

"Nah, not me," Trent chuckled. "I like breasts, don't get me wrong, but
those big floppy ones? Nah. C cup is good, but give me a good old B cup
anytime and I'm just fine."

My heart almost leapt from my bra at that comment. If he only knew what he
was doing to me! If he said one more thing like that I just knew I was
going to cum in Debi's panties.

"Actually I just came to see you, I mean watch you. Gotta support my roomie
after all," Trent said, blushing slightly for the first time since I'd met
him. He suddenly leaned closer and sniffed. "You really smell nice."

"Well..." I began, flabbergasted by his statement. "Thank you for that,
Trent. I don't know what to say." I hoped I wasn't going to cry again. Had
I thanked him for coming to watch me or because he said that I smelled
nice? I was so confused; thinking straight seemed to be impossible since I
had mentioned giving him head.

"No problem, glad to be here, I'm really enjoying the show... well, guess I
better get back out to my seat. Break a leg and do a cheer for me when you
get back out there," he said, turning away. I really didn't want him to
go. I wanted to drop that costume there on the hallway floor and shout
`See? I'm a woman! Your woman, Trent'! Of course I didn't. I watched him
for a moment, his butt looks nice in jeans, and then turned with a sigh
back to my locker room.

"Uh, Josh?" he asked, turning and coming back towards me. I gladly waited
for him; every second spent talking to him while wearing what I was wearing
was pure bliss for me.

"Yes Trent?" I asked, my voice as soft and feminine as possible. I knew he
wouldn't notice; my voice is not exactly masculine at the best of times.

"I just figured that I should tell you that... well the costume is kind of
torn... I mean, there's a rip in it, right here in the back," he said,
turning me and moving quickly before I could stop him.

My heart had stopped in fear. How bad was it? What had he seen? Before I
could turn away or run for the safety of my dressing room he was behind me,
lifting the puma's tail in reaching in to place his hand directly on my
butt cheek. His hand was beneath my skirt but the bottoms of my outfit
barely covered my panties. He was touching me directly on the skin of my
ass.

"It happened when you did the splits, there about halfway through the half?
I believe I was the only one that noticed, you can't see anything except
when you do a handstand or cartwheel or whatever," he said, slowing
withdrawing his hand from my backside. "But maybe you shouldn't do any more
of those, if you don't want anyone to see what you're wearing," he
finished.

My heart had stopped again. I was torn between fear at being found out and
desire for him to put his hand back where it had been. I stumbled out a
thank you and nearly dived back into my dressing room.

I was mortified with having been found out, and by my roommate no less! My
life was truly over, at least at this college. Even as I sobbed my heart
out I was shedding my feminine clothing and wondering if my scholarship
would transfer to another university. By the time I came back out for the
second half it was nearly half-way over, one of the alternate cheerleaders
had to be sent to get me and Ms. Chlebowski was furious with me. I mumbled
something about having lost track of the time and she eventually forgave
me. I was doing a better job than anyone else she could have gotten midway
through the year since I knew all the routines already, so she really
didn't have any choice. I finally stumbled back onto the court wearing my
boring old sweat suit; I had even removed my panties, beneath Lendy's furry
exterior.

Despite my change of clothing I was still wary about doing cartwheels in
the costume. I wasn't certain what all had been revealed but at the very
least the hem of my cheerleading skirt had to been visible for Trent to
have recognized it. I'm glad no one could see my face because the mixed
embarrassment and fright must have been a horrible thing to see. Who else
had noticed? Who else would be waiting to make fun of me after the game or
tomorrow? Trent wouldn't be in the stands anymore, I knew that, he'd be
back at our room packing or tossing my things out the window. I didn't
blame him; seeing his roommate wearing women's clothing must have been a
terrible shock. Seeing him sitting there in my old seat was almost more
than I could believe.

I'd never been so nervous and I can't believe that it didn't show. Everyone
said that I did a great job in the second half but I don't see how. Trent
sat and smiled at me, applauding my every move without paying any real
attention to the basketball game and my knees knocked in fear and
excitement. Only once did he show anything but support for me, and that was
just after my first flip of the half. I came up in the victorious, arms
high position they teach you in gymnastics to find him frowning. Something
had upset him, but what? Immediately after his smile returned as he
applauded me and I soon pushed any thoughts of the frown away; apparently
he wasn't mad at me. That made me feel a little better; perhaps his moving
out wouldn't be quite so dramatic after all. By the end of the game I had
resolved to be the one to move out just as soon as he brought the subject
up; I could stay in Debi's room after all; no one seemed to mind.

The game finally ended and I fled to the locker room. My intentions were to
change as quickly as possible and hurry back to the dorm before anyone who
had noticed what I was wearing in the first half could accost me. I even
considered leaving in the costume just to save time but knew that
Ms. Chlebowski wouldn't like that. Maybe I could find a side door no one
knew about, and so avoid the heckling crowds. An easy escape was not to be,
however, as standing right in front of my dressing room door waiting for me
was Trent.

My shoulders sagged at the coming confrontation. He was being polite about
the issue, staying for the rest of the game was evidence of that, but there
was no way I could avoid discussing what he had seen with him. Could I
convince him to keep my secret as Debi had done? I doubted it. I just hoped
he didn't get really mad and beat me up.

"Hi Trent," I mumbled, pulling the puma head off and clutching it to my
side. "I hope you enjoyed the game." My `hope' sounded pretty weak and
depressed. I just wanted the bad part of this conversation behind us. He
smiled, even when depressed that sent a surge of pleasure through my
body. He was so pretty!

"I didn't really watch much of the game, I was just here to see you," he
said, placing a hand on my shoulder.

"Oh, well thanks," I murmured, unsure how to progress from here. Surely he
just wanted to tell me to get out of our room but he sure was beating
around the bush about it. I decided not to be the one to bring up the
subject. "I guess I did ok, I was pretty nervous."

"You did a fantastic job! As good as Debi could have," he bragged, bringing
another blush to my face. There wasn't anything he could have said about my
Lendy skills that would have made me feel better than that. But, he wasn't
done speaking. "Of course, I thought you did a better job in the first half
than you did the second."

Here it came; somehow he was going to swing the conversation back around to
what I had been wearing. Suddenly I decided that we needed to get out of
the hallway for this conversation; being alone in my locker room with him
might get me beat up but at least there was less chance for someone to
overhear. Ducking around him I motioned for him to follow me into the room
as I responded.

"I guess I was a little tired by the second half," I said, thinking to
myself that `tired' should have been replaced with `mortified'.

"Tired? Nah, I don't think it was that. You just seemed
more... comfortable, in the first half," he said as if thinking hard about
it. "You're movements were more confident; freer, in some way."

We were halfway through the door now when I realized my mistake. My
cheerleading outfit was scattered all over the place; I hadn't even
bothered to hang it up when I had changed. I had been in too big a
hurry. Everything I had been wearing was immediately visible to Trent, and
it was too late to distract him from following me into the room. Now he
would know that I had not only been wearing a cheerleading outfit, but all
the feminine underwear that went with it. Even my breast forms were
visible! I could have died, and even wished that I could at that moment.

He said nothing, just stepping around me where I stood stiff-backed and
closed the door behind him. I could see that he was looking at the panties
I had been wearing; they were laying inside-out across the end of the
bench. Next he stepped over to the locker itself and picked up one of my
breast forms from the top shelf. Cupping it in his hand for a moment he
smiled and said: "B cup, I believe."

That was all I could take, I collapsed onto the bench and began to sob. As
much as I had cried since Debi died I wouldn't have thought that any more
tears were possible but they flowed freely anyway. Surprise couldn't begin
to express my feelings when Trent sat down beside me and put his arm around
my shoulders.

"Shh, Josh ease up man," he said, hugging me to him with one arm. I wasn't
sure how to react so I simply sat very still, the tears flowing but the
feeling of his arm around me too wonderful to ignore. I tried to think of
some excuse for what I had been wearing; a lost bet, a hazing ritual for a
fraternity, but nothing that I sputtered made sense. Trent wasn't listening
to my babbling anyway.

"Look Josh, you like wearing women's clothing, that's ok," he said,
shushing me. "If it makes you happy, then I'm ok with it. I'm sorry if my
finding out hurt you but you have to believe me when I say that your secret
is safe with me."

I tried to choke back my sobs but it was difficult. Of course my secret was
safe with him. Now that I thought about it; he couldn't tell anyone for
fear of looking gay himself after having lived with me for all those
months. His soft voice eased my tension some, and the stiffness left my
body allowing him to pull me a little closer by my shoulders. I couldn't
think of anything to say so I just sat silently, miserable and yet elated
at the feel of him sitting so close, even through a puma costume his body
heat was palpable.

"It's not like I didn't suspect; a lot of people around campus think that
you're gay, but I didn't realize that you wanted to dress up in women's
clothing. I think that's great; you should do it if that's what you feel,"
he said, squeezing me closer again. He may have been doing that to show
support but he was seriously turning me on!

"Just because I wore women's clothing, it doesn't mean that I'm gay!" I
managed, looking towards him but not able to lift my gaze above his chin. I
was afraid that he would see the lie in my eyes immediately.

"I understand that," Trent said, reaching down and cupping my chin
gently. Lifting it up, he forced our gazes to meet before he
continued. "But you are gay, aren't you Josh?"

The tears were welling up again and I tried to choke out an argument but
all that came from my mouth was a sob and four whispered words.

"My name is Jill."

I cried really hard then. He took me in both his arms and held me close,
making those small `shh-ing' sounds that people do to calm someone who is
crying. I put my arms around his waist and buried my face in his chest. I
was miserable but loving it too. I even cried a little longer than
necessary just so he wouldn't let go. Finally my sobs eased and he pulled
away. Reluctantly I let him go before turning to the locker to find a
cleanex. It was a good thing that I wasn't wearing makeup; it would have
run all down my face.

Woodenly I began to strip off Lendy, my gray sweat suit plastered with
moisture and a distinct odor of sweaty body rising up from me. I stripped
the top off but stopped before removing the bottoms; I didn't want Trent
seeing me naked or even nearly so. I needed to take a shower badly but
couldn't so long as he was here. I sat with my back to him, suddenly
noticing the two red splotches on my chest where I had removed the breast
forms too quickly, looking only at my feet. He stood behind the bench
watching me, expecting me to say something, I suppose, but I had nothing to
say. My life was over; despite his claims I knew that the whole campus
would soon know everything about me. At that moment I really wished that I
could die; perhaps Debi and I could be together again.

"I never really noticed how attractive you are," Trent said, his voice soft
yet causing me to jump when he spoke. "I bet you're beautiful when you're
all dressed up."

I said nothing; my heart was pounding too loud and would have drowned me
out anyway. I wanted him to say that again but he didn't; he moved on to
something even more wonderful.

"As a matter of fact, I bet you look really nice in your cheerleading
outfit. I'd really like to see you in it, without the Lendy suit over the
top," he chuckled.

Somehow I managed to turn my head enough to see him. I wanted to see the
derision on his face; the proof that what he had just said was nothing more
than a cruel joke. I saw nothing like that; only sincerity and his
to-die-for smile.

My words were almost a whisper. "I... can't wear it home... someone would
see..."

"No problem," he said excitedly. "Just bring it home with you and you can
model it for me... Jill."

The woman inside of me leapt for joy at Trent saying my feminine name. The
tears in my eyes turned instantly from sorrow to happiness and it was all
that I could do not to jump up from that bench and into his arms. At first
I had no idea how to respond but finally something came to mind.

"If you want me to, I will Trent," I managed. "But I'll need some time
before you get there... I don't want you to see me change."

Trent's smile went from hot to panty-melting luscious. "No problem, I'll go
grab a burger and see you at our place in, what? An hour?"

I nodded happily as my mind replayed his words; `Our Place'.

He left, suddenly seeming as awkward as I ever was around someone I wanted
to date. Our goodbyes were perfunctory but I barely noticed, waiting for
him to close the door so I could jump into the shower.

I showered quickly, re-shaving my body despite having done it only a couple
of hours before. I needed to look my best after all. Once I was clean and
at least partially toweled dry I hastily put on a pair of panties, and to
my surprise, a clean bra for the walk home. I rarely wore a bra outside but
somehow this situation demanded it. There was still a chance that Trent was
setting me up somehow, perhaps bringing some of his jock friends over to
embarrass me once I was dressed, but at that moment, for the first time in
my life, I just didn't care. If there was even the slightest chance that I
could become Trent's girl then I was going to go for it. Once my drab male
outer clothes were in place I hastily repacked all my girly things and with
the cheerleading outfit safely stowed in my gym bag, rushed out of the
building.

Almost running I hurried home, stopping by Debi's place for a few things I
would need along the way. I reached our room with only thirty minutes to
prepare and flew through my routine. I know it was silly but I put on a
pair of sheer pantyhose along with a matching white panty-bra set that was
very lacey and almost brand new. The cheerleading outfit slid on as
dreamily as before and the little bottoms fit as snugly as they could have
on Debi. A pair of ankle socks with fuzzy little pink balls and Debi's pink
shoes completed my outfit, giving me only fifteen minutes to fix my hair
and put on my makeup. I made it but only barely; Trent arrived exactly on
time; not a second late!

It surprised me that he knocked; he lived there too, after all, but I was
glad that he did as it gave me a moment to calm myself. My hair was back in
its ponytail, I really didn't know what else to do with it, and at least
according to the mirror I looked as good as any real cheerleader could
have. Practicing my girlish walk, just as Debi had taught me, I minced my
way to the door as I struggled to breathe through my anxiety. Thankfully
the door had a peephole, so being able to see that Trent was alone helped
calm me somewhat. Finally throwing caution to the wind I threw the door
back and gave him his first look at Jill.

Was he surprised at how good I looked? He says that he wasn't but I could
tell that he was flabbergasted. He had brought me flowers (where had he
found them this late?) and never failed to call me Jill after he entered
the room. We talked for an hour, me sitting demurely on the edge of a chair
while he sat half-reclining on his bed. Eventually he convinced me to put
on a cheerleading exhibition for him and watched excitedly as I kicked my
legs and tumbled about the room. I could tell that he really liked my legs
and when I did a hand-stand he held his breath the whole time my skirt was
up; the crotch of my tiny cheerleader shorts completely exposed to his
gaze. Finally, out of breath, I allowed him to grab my hand and pull me
down to sit next to him on the bed. I looked at him, smiling with the joy
of showing off for him and found his lips closing in on mine.

We kissed.

It wasn't a mouth-open tongue-wrestling match, it was just a kiss even if
the world did stop rotating. Our mouths were slightly open, I know I didn't
breathe the whole time, and we probably only held it for about ten seconds
but I was immediately in love with that sweet man. When we broke away we
didn't look at one another for a minute or so; just sat looking away and
thinking about that kiss. My whole body was tingling; from my toes upward,
at the thought of what had just happened. My mind was spinning; perhaps
from a lack of oxygen but the kiss had contributed as well. I wasn't sure
if he was sorry we had kissed, but if he wasn't going to say anything to
ruin the moment I certainly wasn't. Finally I felt him turn towards me so I
looked his way as well; even if he was going to tell me that kissing me was
a complete mistake I wanted to watch his sweet lips as he said it. He had
kissed me!

Whatever he had been planning on saying was never spoken; we silently
drifted back together for another soft kiss. Another followed that one and
soon enough we were going at it hot and heavy; our tongues licking one
another as our lips moved softly together. We didn't break our lip-lock for
what seemed like only a few minutes but could have been hours. When I came
back to myself Trent was lying back on his bed and I was laying half-way on
top of him. His arms were wrapped tightly around me and my hands were
wandering across his muscular chest. We stopped for a moment to catch our
breaths and I took the opportunity to rest my head on him as well; it felt
as wonderful as I had ever imagined to be lying there in his arms. Soon
though I knew it would go further; there was no way I was going to let this
end here.

Trent excused himself to go to the bathroom and I freshened up a little as
well. When he returned I met him at the door and after making sure the
hallway was clear, gave him a long, lingering kiss. His hands slid up my
skirt and found only panties between his skin and my rear. I think he liked
that; he certainly gave my ass plenty of attention. Once the door was
closed I took his hand and led him back to his bed, mine didn't even exist
at that point; I had wanted to be in his with him for so long. I helped him
undress as we went; getting those tight jeans off was a chore but I loved
ever second of it. Finally came the moment I was waiting for; the removal
of his underwear. Trent wore briefs most of the time, and tonight was no
exception. I dropped to my knees when his `tighty-whities' were all that he
had on and smiled shyly up at him as I grabbed onto the waistband.

He smiled back, and I excitedly began to slowly strip him of his shorts. I
was desperate to see his cock but didn't want this wonderful moment to end
too quickly. Slowly, so slowly, I pulled down on the elastic, watching for
the first sign of his manhood to appear. I had no preconceptions of how
large or small he would be; I knew that he had to be bigger than me, and I
really had no idea what it would look like, my only experience with a
`live' cock was with my own, and that had never caused the sort of bulge I
had seen in Trent's shorts. I kept expecting to see the head of his cock
first, surely that bulge meant that he was already erect, but as the
underwear descended I continued to be frustrated. Where was it?

Suddenly it was there, but not the engorged cock head I had been expecting
but the thick base of a truly man-sized dick emerged from the crop of kinky
pubic hair. I couldn't believe how thick it was, or that it was apparently
still not hard despite the bulge, and began to pull his shorts down even
more slowly as my hungry eyes devoured each emerging inch. How big could it
be? I couldn't begin to guess but my mouth was already watering over what I
had seen so far.

Inch after glorious inch was revealed as I pulled the shorts down. It was
partially erect but protruded at least two inches straight out from his
body before it sagged downward beneath its own weight. He gave a sigh of
relief as it was freed; I guess it was pretty uncomfortable all bent up
like that. Finally, just as I decided that it might drag the floor before I
freed it, a complete exaggeration of course, the head of his cock slid free
of the restraining elastic, and I could finally behold the beauty that was
his dick.

Did I mention that it was big? It was, wondrously so. I don't know how long
exactly but it was certainly bigger than anything I had ever seen on the
internet. The head itself was thick and looked to be longer than my
thumb. It was the most beautiful thing I had ever seen, at least until it
was completely hard. I realized that I was holding my breath and let it out
quickly; it was so beautiful it was breathtaking anyway; no sense in
passing out now before I had even gotten to touch it!

Hands shaking, I reached out to grip Trent's massive member, smiling at his
groan of approval as the thick base was gently gripped in my palm. I still
couldn't take my eyes off it; it was so perfect with its thick ropey veins
and fantastic proportions. It immediately began to twitch once I had it,
and to my amazed sight began to thicken and grow. The head started lifting
with each twitch, rising from its downward-pointing position until it was
almost sticking straight out in front of him... and right directly at
me. Tentatively I leaned forward and licked it right on the very tip,
reveling in the salty taste of his cock. It was delicious! Opening my lips
I kissed it next, sneaking in a second lick as I did so and then grabbed it
with my other hand as well so that I could better admire the lipstick I had
left there.

"Oh, yeah, Jill," Trent groaned, his thick cock now jutting proudly out
before him. I couldn't see how it could get any bigger but it was obviously
still getting harder and I adjusted my grip to compensate. Trembling with
pleasure I opened my mouth even wider and slid his glorious manhood inside,
carefully pulling my teeth back just as Debi had taught me and allowing it
to nestle on my tongue. Nursing gently on it for a moment with just the
head inside gave me a good taste of his precum as his mammoth dick hardened
even further inside my mouth. I absolutely adored the flavor. I pulled back
only for a moment, his groan of disappointment was too sexy to ignore, and
finally got to see him fully erect; and believe you me it was
magnificent. I slid him back where he belonged and slid it in and out of my
mouth for a while; so happy I could have died.

Rising to my feet I kept his cock firmly in my hand and gently led him to
his bed, turning him and pushing him so that he lay on his back before
me. He was all mine; his cock jutting firmly upwards with its need; a need
that only I could fulfill. Sighing in pleasure I knelt beside his bed and
with his cock still gripped in one hand, lowered my face upon it.

It was wonderful! I kissed, licked and gnawed at his beautiful beast,
trying to taste every glorious inch. I couldn't deep throat him,
unfortunately, but I did the best that I could. I quickly found the spots
he liked me to lick the best and all too soon I sensed that he was nearing
the point of no return. I wanted it to last longer, honestly I did, but I
just couldn't wait to taste his cum so I left off sucking his balls and
positioned myself so that my hungry mouth was right above him and then I
slid his wonderful cock back into my mouth and began bobbing up and down;
all the while stroking his meat with both hands as I urged him to cum in my
mouth. With a grunt and an `Oh, Jill!' he did just that; arching his back
as his sperm erupted into my waiting mouth.

All that I can say as that it was even better than I had ever imagined. Had
he cum a gallon, I would have wanted to taste every drop. As it was I ended
up wearing a lot of it, but enough made it onto my tongue that I was
satisfied for the time being. I sucked on it long after his orgasm was
complete, and he rewarded me by never going even a little bit soft.

"Can I fuck you, Jill?" he eventually asked once his breathing had eased. I
said nothing, just used my favorite handle, his cock, and urged him out of
the bed so that I could take his place. My `pussy' was already well
lubricated so I lay on my back with my legs spread wide; I couldn't wait to
feel however much of his cock I could take inside me. He didn't make me
wait but immediately crawled on top of me after flipping my skirt up. Once
his body weight was in place, that was really nice all by itself, I felt
him tugging my panties to one side and then, glory of glories, his cock
head pushing up against my opening. I shivered in a mixed state of bliss;
combining fear, anticipation, and a life of desire into one overwhelming
emotion. Trent moved his mouth to my neck where he bit lightly at me as my
attention remained only on that part of his body that was entering
mine. Then, after giving me a moment to gather myself, he began to thrust
his hips forward.

Yes it hurt; it felt amazingly wonderful as well. I couldn't take all of
himl but I did pretty well for a virgin. Trent was inside me, his big cock
pounding my little pussy as he drove me to orgasm after orgasm. Debi had
tried to tell me how good it felt to have a man inside you but she just
couldn't do justice to the act itself. My mind ran away on the waves of
repeated orgasms, reveling in the feeling of him sliding in and out of
me. Later I heard some of our neighbors congratulating Trent on the fucking
he gave that `slut' that night, so I know that I wasn't too quiet. I didn't
care; all I cared about was the pleasure I was getting from my man. Ten
minutes or six hours later, I couldn't be sure; I felt the warm spray of
his sperm inside me. We clung together for a while, whispering little
endearments until we fell asleep in one another's arms.

We tried to keep our relationship a secret and we were successful there;
however my crossdressing quickly became the best-kept secret that everyone
at Lender College knew about. One of the cheerleaders had also noticed what
I was wearing underneath Lendy that first game but didn't say anything for
a few weeks. She apparently had a brother who crossdressed and so was
sympathetic. Eventually she did tell her best friend and the two of them
decided to speak with me about it. Before long the entire cheerleading
squad knew about me and ultimately I was allowed to practice with them in
Debi's cheerleading outfit without Lendy. This led to my forsaking my men's
clothing completely; everyone knew about me already and wearing skirts to
class was thrilling. Before I began living as a woman I would never have
dreamed that revealing my feminine side could have filled me with such
confidence but it most certainly did. Being caught wearing panties and a
bra was once my greatest fear but now being seen in public as a woman is
something I look forward to.

When one of the girls from the squad twisted an ankle, I was allowed to
fill in as an alternate on the cheer squad. That only allowed me to sit on
the sidelines and shake my pompoms but it was still a wonderful
experience. There were a few nasty things said to me here and there but
with Trent's love and the support of my new friends I overcame them; being
a woman full-time was simply too fantastic to worry about that sort of
stuff.

Naturally my relationship with Trent became more difficult when my secret
got out. He didn't want to be thought of as gay and maintained that I was
all woman to him. I was thrilled with that thought and so I offered to move
out of our room and into Debi's to help preserve his reputation. That was
what I did but I still spent most nights with Trent; I still cleaned his
room and I did all of our laundry together. I also took care of his more
basic needs; that man's sex drive is insatiable! I am so thankful for
that. No one said a word to me about staying in Debi's room, I didn't think
that they would, and the other girls of the dorm welcomed me as their new
sister. I was even offered to pledge with a sorority for my sophomore year!

The next year flew by and so many wonderful things happened to me. Trent
and I are still together and as my transformation to living as a woman
full-time began we decided that we should move away from Lender College.
When that year ended I was beginning hormone treatments, how I desperately
wanted my own breasts, and Trent accepted a scholarship at a larger
university. I was able to transfer to the same school myself; apparently
the grades I make are universally accepted. By the time the new school year
began my name was officially Jill and so far as I knew no one at the new
university had any idea that I was once Josh. That took some creative
paperwork but I managed it. My computer skills are topnotch. We live in a
small apartment just off campus and some of our new friends think that
we're married... I love that thought. I wished now that I had legally
changed my last name when I became Jill.

I eventually told my mom about Trent, and she wasn't as supportive as I had
hoped but we'll work through it. I walked on to the cheerleading squad at
the new university and made the team... as an alternate (argh!). Still, I
get to practice with them and despite my love for Trent do enjoy having my
little body tossed around by those big strong men. Sitting upon their hands
while they lift me up in the air is pretty nice too; nothing like a good
grope to make a girl feel special, lol!

My breasts finally began to come in by the time my junior year began; I was
getting so tired of wearing those breast forms. My doctor says that I seem
to be destined for `big B' or borderline C cup. That's more than enough for
me, and for my Trent. He loves my breasts and spends a lot of time kissing
and sucking them. What that man can do with a nipple... wow.

I think this is going to be our year. After starring at Lender as a
freshman, Trent didn't have to sit out a year but still didn't play a lot
as a sophomore. Now, as a junior, he is starting and is one of his team's
better players. I think I can make the cheerleading squad for real this
year; not just as an alternate sitting around waiting for an injury, and if
not the dance squad is trying hard to recruit me! I've been to meet Trent's
family lots of times; they have all accepted me as a female and I'm not
sure if or when we're going to tell them the truth. Lately I've been
considering surgery to finish the deal and if that happens, maybe I won't
have to. It would be nice to have my very own vagina but I'm not sure that
I have enough `equipment' for the doctors to work with down there.

Thank you for listening to my story. I am happier now than I have ever been
but am more than a little sad that it all came about because of the tragedy
of another. I wish Debi could be with me and share in my joy but I will
always love her for what she gave me; a whole new life.