Date: Thu, 19 Mar 2009 12:37:09 -0700 (PDT)
From: Fred Gingerman <gingerfred2005@yahoo.com>
Subject: Pretty Boy (transgender, high school)

Pretty Boy
by Gingerfred Man


Chapter One -- Too Pretty


What do you do when you're a boy and your genes made you pretty? Not
handsome. Not boyishly cute. Pretty.

It wasn't bad when I was a small boy. My mother would dress me
androgynously and everyone would compliment her on her beautiful
daughter. Sometimes Mama would correct people. Mostly she wouldn't. When I
was old enough to know what was happening, I was very embarrassed. I was a
boy, after all. And I wanted to be a boy. I played with trucks and Army men
and got into fights and played and followed baseball.

But it was difficult. I suspect Mama always wanted a daughter. Dad left her
for the pizza delivery girl when I was around two. Fatherhood was too big a
challenge for Dad. He couldn't deal with a kid when he was still one
himself.

I was teased for my looks, of course. Some of the bullies in school saw me
as an easy target. Until I rearranged some dentistry. I was no pushover and
no wimp. Just pretty.

Thank goodness for Dennis Matthews, my best friend since sixth
grade. Dennis was the one guy I knew who didn't care that I was pretty. He
just treated me like Sam Burns, regular guy.

Not every male treated me with scorn, though scorn would have been
better. There were a substantial number of males of all ages, who wanted to
get me in the sack and do sex things to and with me. And I don't mean gay
males. These were straight men in whom my looks and, I guess, personality
triggered some deep, primeval instinct. They saw me, processed what they
saw, and their instinct told them to get me into the sack.

I wanted none of that. I was heterosexual. They could just keep their
stiffies zipped up.

I had no real girlfriends all the way through high school. And
surprisingly, I didn't mind. Dennis had enough for the both of us. And a
platoon more. Dennis and I were complete opposites. He was the most macho
stud in school. I was considered a sissy. Just because of my looks.

Dennis and I were friends despite, or maybe because of our differences. I
was always delighted to see Dennis. A little thrill gripped my heart when
he looked at me. I got sort of tongue-tied when he praised me. Sometimes he
would even bring me little presents. That's how friends act with each
other, right?

As Dennis and I entered our senior year of high school, we celebrated our
mutual 18th birthdays with pizza.

We were two days apart (I was older) and had just missed the cutoff, so we
were the oldest kids in our class. I told Dennis that I was going to see
about securing a girlfriend this year.

In his easy manner, Dennis said, "You don't secure girls, Sam. You woo
them. Do you know how to woo girls?"

"Of course I do. No, I don't. How?"

"Listen to them. Girls love to talk. And complain. Nod and agree a lot, but
only offer your opinion under threat of your life. Girls don't want to hear
your opinion. They only want to vent." (How true. You are certainly an
astute observer of the opposite sex)

Fascinating.

He went on. "Certain girls, probably the sexiest, you'll never get near
because you don't have an eight-inch-diameter tattoo or even better, a
Class C felony conviction. Most girls like the bad boys. They also like to
be treated like shit, left pregnant, then abandoned."

Wow. "Why?" I asked.

"Regis himself couldn't answer that one, even with three lifelines,
Sam. But remember, there are more of them than there are of us. Plus, some
guys are gay, some don't want relationships, and some are too scared. The
odds are with you."

As always, Dennis had made me feel better. And all funny inside too. Dennis
knew so much about girls. I was proud that girls liked my friend. But maybe
a little jealous too. I wondered why.



Chapter Two -- An Odd Mom

If you're reading this, you've probably read a lot of stories where a young
crossdresser hides his appetites from the world, and especially his
mother. I had a very different situation.

>From the age of 13, I was encouraged by Mama to "try on some pretty
things." We fought pitched battles over it. I wanted no part of girl's
clothes, but Mama tried to convince me that it was best for me.

She was convinced that I was too pretty to be a man and would be unhappy as
a man. She never insisted, but she pushed. Each year for Christmas and my
birthday, she would buy me normal presents. But she would also give me
several items of girlie things. Makeup toned for my coloring. Lingerie,
skirts, shoes, tops, extraordinarily high heels. Panties and nighties were
the most common gifts, along with sexual aids, which I'll tell you more
about later.

All that five years worth of stuff was in a box buried deep in my closet. I
couldn't throw it away. Mama would have my head. So I just pretended it
wasn't there.

Of course we all have periods of curiosity. Now and then, over the years, I
did pull out the odd nightie and try it on. It felt heavenly and when I
looked at myself in the mirror, I looked as pretty as any girl I had ever
seen. It was disgusting! In a strange, wonderful way.

A couple of times, trying to be nice to my mother, I modeled some of her
presents for her. You know, the odd pink nightie or two. She was always so
over the top with her praise of my beauty that I was beet-red with
embarrassment. Sometimes the head of my tinkler was beet-red too from
seeing myself like that. But I couldn't help that. So at around age 15, I
refused to model any more.

Mama wasn't totally obnoxious about it, but I heard things like, "Oh, Sam,
this 13-inch mini would look darling on you! You have such gorgeous legs."

I would cringe hearing stuff like that. But she was right. I did have
gorgeous legs. I couldn't wear shorts in public. Seeing the legs that went
with my pretty face would be way too much for the men of our town. They
would either wank themselves into a dehydration coma or try and force sex
on me. Yuck. Did I mention I also have an ass women would kill to have? A
perfect bubble butt, plump and girlishly sexy.

Why me?



Chapter Three -- Phil

I've always heard that you never see the car that runs you over. I never
saw Phil Winslow until he was deeply involved with Mama.

Mama was only twenty when she had me. So she was only 38 my senior year in
high school. She was, by all accounts, a very beautiful and sexy woman. I
knew that adults, even mothers have needs, so I never begrudged her her
boyfriends. Until Phil.

Phil was good-looking; I'll give him that. But very arrogant. He was the
first of Mama's boyfriends who seemed to be calling the shots. Mama liked
that. And Phil was just enough of a bad boy to really appeal to Mama.

Mama was always very discreet about her men, until Phil. I'm sure she was
getting her ashes hauled by someone or other over the years, but she kept
it out of the house. Until Phil.

"You're a man now, Sam," she said to me one day. "I'm sure you'll
understand if Phil and I express our affection for each other in our home."

I didn't understand. Why did Mama think it was all right to have screaming
sex in the bedroom next to mine? I hadn't even really thought much about
sex and had never even masturbated. Even when I was wearing those awful,
silky nighties. Now sex was in my face.

Three or four nights a week, Phil and Mama would light up her bedroom all
night. And they were loud. Mama was letting all her inhibitions go at once.

Of course I had to see Phil now and then. It was so embarrassing for me to
know what I knew and know that he knew I knew it. But it didn't bother
Phil. He spoke to me in a friendly enough manner. But I'm sure he knew I
wanted him gone.

At least I thought I did. After about three weeks of my first second-hand
experiences with carnality, the strangest things began to happen.

I began to get very excited by listening to my mother <blush> fucking her
lover. My little willie was stiff the whole time I listened to them. I knew
that you could make good things happen to yourself if you rubbed it. Even I
knew that. So I sort of rubbed my cock and listened to them grunt and
squeal and scream in orgasm.

It was wrong to fantasize about making love to my mother. Please. I knew
that. That wasn't what I was doing at all. I'm embarrassed to tell you
this, but I was imagining that Phil was making love to me, not Mama.

Sick, huh?

I couldn't explain it, but it was clear to me. I wanted to be under Phil,
taking all of his hot cock into me. How did that happen? What kicked in
with my chromosomes?

Oh. I was smothered by guilt. I was evil. I was cumming so hard I almost
blew my head off.

Every night that Phil was with Mama, I would lie in bed and pleasure myself
using the gayest, most evil, most vivid thoughts of Phil dominating
me. Making me his sex toy. Making me cum over and over. I wanted to discuss
it with someone who could help me stop. But I was even ashamed to tell
Dennis. Even though I was sure he would understand. He was always so sweet
and kind to me.

Worse, one afternoon alone, I opened the forbidden chest of girlie things
in my closet with some intentions of trying out whatever I found. I wanted
to find some things that might have made me more attractive to Phil. If he
ever saw me in them. Which he would definitely not.

I was so depraved. Fighting my nature and my desires, I compromised. I took
out only a pair of pink, nylon, bikini panties.

I was trembling when I stripped to the buff and tried them
on. Ohhhhhhh. They were exquisite. They tortured and rubbed my hair-trigger
cockhead and caressed my pretty pink ball bag. It was...I
was.....Oh......That was the end of those pink panties. I came so hard that
I fell to my knees. The panties were sopping with cum.

What was I doing? Had I lost it? I was through with this panty business. I
was going to take a shower, get into proper boy's clothes, and go out and
find a girlfriend. Right after I tried on those wispy, black thong panties
with the lacy pouch for my cock and balls.

Oh, did they feel good. What would the girls in school think if they saw me
like this? Their eyes always pass right over me. What would the boys think?
I checked myself out in the mirror. Good golly! The boys would be attacking
me in packs. They would be lined up around the block just to rub against
me. I was H-O-T-T!

What would that no-good Phil think? I knew he was hot for Mama, but could
he resist my forest-fire-hot body? No man could. I was irresistible. If
Phil saw me he would run over and kiss me, making me weak with pleasure. He
would stroke my pantied butt as he kissed my neck. He would take my clitty
(did I say clitty?) between his thumb and fingers and twiddle the head,
teasing me evilly, until I was gasping and then I would CUM! Just as I
really was from the thought, ruining a second pair of sexy panties in seven
minutes. Oh. It was intense!

Why was I so gaga over this gigolo? This loser? This bad boy? Why was I
thinking about any man?

Three pair of cum-soaked panties later, I was no closer to an answer.

I washed the panties by hand and hid them in my closet to dry. I prayed
Mama didn't find them and ask a lot of embarrassing questions, like, "So,
what do you think about when you're tossing yourself off in your panties."

Mama would ask a question like that too. Believe me.

Thank goodness, I was undetected, but the next afternoon and every
afternoon for three weeks, I was a slave to orgasm. I counted fifteen pairs
of panties in my sissy chest and every one of them received several hot
loads.

And so did my twelve pairs of sheer stockings.

I figured I might as well try them on too. I was glad I did, since the
cool, sensuous feel of them rolling up my shaved legs made me cum even
before I got my panties on. Cum would drool down my stockings and
sometimes, very naughtily, I would lick it off my hand. I was becoming a
cummy little tramp. In my own mind, at least.

Since I had already tried the panties and stockings, I figured it couldn't
hurt to see what else was in my sissy chest. Mom had bought me lots of
nasty little toys over the years. I held up what she had bought me on my
thirteenth birthday. I was humiliated to receive it and it was still in the
package. "The Cherry Popper," the label called it. It was a relatively
short and slim, dark red, semi-hard-gel object shaped like a circumcised
cock. It used batteries and vibrated when you turned a switch. The label
said it was a "beginner's introduction to anal sex."

After five years without it, I decided that the device was just right for
me to pop my cherry. I had never had anything in my tiny hole before, and
the thought of even putting my fingers in there was scary -- and very
exciting. I followed the label directions, lubricating it thoroughly. The
five-year-old battery didn't work, so I found a new one.

Gently, I pushed the head against my tight sissyhole. I pushed again and
gasped with pleasure as the head penetrated the fortress. It was
wonderful. Even with that little, 12-year-old-size cock vibrating in my
butt, I felt stuffed and sexy. I dared to stroke my cock as the little
penis did its duty and built quickly to an orgasm. As I came, my ass
clamped on the "Cherry Popper" and I wasn't spurting my cream! I panicked
for an instant, then almost doubled over with the intensity of the delayed,
strained ejaculation. Was this what anal sex was like? Oh my!

In a couple of days, the Cherry Popper seemed too tame for me, so I went
back to the sissy chest. This time, I found the "Shower Buddy" that Mom had
bought for me on my 14th birthday. It was a 50% bigger, semi-hard-gel cock,
blue, angled strangely and attached to what appeared to be a large suction
cup. I read the directions and took it to the shower with me. I used the
suction cup to attach it to the shower wall tiles, then stripped and turned
on the warm water. I soaped my body, and then shampooed my hair, lathering
up really well. A lot of the lather, I applied to my little hole with two
probing fingers. Then I backed into the well-placed Shower Buddy, inch by
inch. Ohhhhhhh. It was incredible. I rocked back and forth on it, cumming
twice, then a third, desperate time. I used the Shower Buddy so often that
every time I went out in the rain, I got an erection

But there was more in that chest. I found my fifteenth birthday present,
the "Tasty Boy." It was a big, seven-inch, lifelike, candy cock, intended
only for sucking. How they did it, I'll never know, but every lick tasted
like cum. Sweet, delicious cum. Mom had bought me a dozen of the Tasty
Boys, and I licked four of them down to slivers that first week. My
cocksucking technique advanced rapidly, but a warm, real one was what I
wanted. Phil's.

I hoped that I hadn't tipped Phil off that I was spilling quarts of hot goo
in his honor. I tried to act like a sullen teenager around him, as
always. He couldn't tell what I was thinking, could he?

It got worse. I started to experiment with cosmetics. And the effect was
startling. I went from pretty to the-cover-of-Glamour beautiful. The hetero
part of me got stiff just looking in the mirror.

I began to wear panties to school. I couldn't be away from them.

I thought about wearing stockings to school too, but then it happened.



Chapter Four -- It

One Friday, I got home from school and saw a note from Mama: "Phil will be
at the house at four. He and I are going out at four-thirty. Please let
Phil in if I'm not home yet."

Rats! I was dreaming all day about cumming six or seven times right after
school. Well, if they were going to be going out, I could prance around the
house most of the night, cumming in every room. I laughed at that. I
stopped laughing when I heard the bell. It was Phil.

I let him in. He greeted me semi-politely. I was sullen, while sneaking
looks at him for details that I would use in that evening's fantasy
entertainment.

I offered him a beer. He thanked me and took it.

Then the phone rang. It was Mama, asking to speak to Phil. They spoke. He
hung up. I looked at Phil.

"Your mother's stuck at work. She won't be home for about an hour."

OK. I would just go to my room.

But Phil said, "You're different, aren't you? I mean you try to act like a
nasty teenager, but you're not. You're a nice kid."

How did he know that? I blinked.

"Your mother adores you, you know. But she thinks you're different too. Of
course, she can't see in you what I see."

I was trembling. I had to know. "What do you see?"

"Pure lust. You're one of the horniest people I've ever seen. And it's much
more than just being a teenager. You have sexual needs."

Oh. I didn't like the way this was going. But my poor stiffie was rock
hard. "You're wrong," I gasped.

"I don't think so. In fact, I think you're hard in your panties right now."

Oh no! What did he know? I felt as if I would cry. I wanted to deny it, but
I couldn't.

Phil said, "Let me see your panties."

I stood at the edge of the cliff. I pulled back. "But I don't have any...."

Phil knew better. "Let me see your panties," he insisted.

I started crying. He didn't move to comfort me. He just stood there,
waiting for my inevitable compliance. He knew I wanted him to see my
panties more than anything. How did he know?

I sniffled, but unbuckled my belt. Then I undid and unzipped my pants. He
sat down in an easy chair, as if to watch the show. I eased my trousers
over my hips, revealing a flash of pink. I looked at him to see if that was
enough. It wasn't.

I pulled my trousers down to my thighs, then to my knees.

Phil said, "Step out of the trousers."

No "please." Just, do it. My cock was throbbing and standing
sentry-straight.

"Now the shirt."

He was a beast. What did he expect? What was he going to do? I was in his
power. Oh my, was I excited!

I stood before Phil in my panties, shoes and socks. Trembling. Hot and
bothered.

"Off with the shoes and socks."

Oh, no. He would see my painted toenails! I was almost peeing myself in
fear. And excitement. I did as he asked.

He didn't act surprised or smug or anything when he saw my pretty
toenails. He just said, "You're very beautiful."

I was standing there almost nude in front of a lusting, unpredictable man,
who could ruin my reputation and maybe my life. But all I thought of at
that moment was that compliment. He thought I was beautiful.

My cock was outrageous.

"Come here," Phil said.

I did.

"Don't be afraid. Sit on my lap."

Oh. I was almost fainting from excitement and fear and shame and delight. I
sat on his lap.

Phil considered me.

"You could be a fashion model. You're a stunning beauty!"

I squirmed with pleasure. He hadn't even touched me and I was almost
cumming.

Then Phil put his hand on my bare back and drew me toward him. I thought he
was going to kiss me, but instead, he kissed my right nipple.

Electric shock! Shudder. Cum hard in panties. Tremble. Begin to cry.

"As I said, you have sexual needs," Phil repeated.

I was so humiliated, but I wanted him to pull my panties down, flip me on
my stomach and pound his pork into my butt.

Instead, Phil kissed me. He kissed me for a good ten minutes. All the air
left the room and I was gasping and panting. And kissing him back. I wanted
him to pull out his cock and let me worship it with my mouth. But I could
never have initiated that. He held my naked upper body in his arms and
kissed me. Then he began to rub the front of my sopping panties. He didn't
pull them down or reach in. He just rubbed. And rubbed. And I got bigger
and harder. Still kissing. We did that for ten more glorious minutes and I
began to feel another, bigger orgasm storming its way toward me. I
flinched, I whimpered. I moaned. And I almost croaked when I heard my
mother's car turn into the driveway. I wanted to run and hide, but my
orgasm was almost there. Phil knew it too and he kept kissing and
rubbing. Mama opened the garage door and began to pull in. I felt the first
spurt of sticky cream leap into my drenched panties. Mama turned off her
engine. The second spurt.
 Mama opened the driver's door. The third spurt. She closed the driver's
door. The fourth spurt and a rush of fear and adrenalin. Mama put her hand
on the doorknob to the kitchen from the garage. Phil stopped kissing me and
looked amused as I jumped up, scooped up my clothes, and tore upstairs. I
ran to my room and just got in as I heard Mama sexily greet Phil. I peeked
out of my door and saw her sit in his lap, right where I had been moments
before.

I was jealous. How could I be jealous of my mother? But I was. And
scared. Phil played a dangerous game with me and didn't flinch. Was I that
brave? Had I made a wet spot that Mama was sitting in?

I was a mess. Especially in my sopping, sticky panties. But oh, baby, was I
sexually excited. Phil wanted me!



Chapter Five - What I Thought I Wanted

Most of that night, I lay in my bed trembling in wild surmise.

What the heck had just happened? And even worse, what would happen next? At
least a dozen times, I almost reached for the phone to call Dennis. But
what would I have said? "Uh, Dennis, remember that Phil guy my Mama likes?
Well he just kissed me and made me cum in my panties. Twice. And now I
really want to suck his cock and have him fuck me.

That would have gone over well. Telling my best friend I was a simpering,
cross-dressing faggot. Why didn't I just go up on the roof and jump off?

Well that no-good Phil was just going to get his tires rotated elsewhere,
because that was it for me. No more sex with him or any male. No more
dressing. I pulled the covers over my head and went to sleep.

I actually kept my promise to myself for the next week and, surprisingly,
Phil seemed to notice and honor my new resolve. We treated each other as we
usually did, which was mostly to ignore each other. Phil gave me no clue as
to what he was thinking and that was just fine with me.

But my insides were burning. Having opened the box to my true nature, I
found that the darned lid just wouldn't close. The following Friday, after
Mama and Phil had gone out, I put on a pretty pink babydoll nightie that
Mama had just bought for my 18th birthday. I looked completely edible!

Of course, after a week of abstinence, I was frothing at the mouth
sexually. So I looked in the sissy chest for new friends. I found the "Anal
Amigo" that Mama had given me for my 17th birthday. It was like the other
fake stiffies, but with a key difference. When you had it fully inserted
into your warm place, you pushed a button and the head and three inches of
shaft pistoned in and out. Ohhhhhhhhhhhhh. It was rubbing on my prostate
and I was in heaven. What made me think I could give that up?

The Anal Amigo took me to paradise five times that night and I fell asleep
with it in my butt. My stomach was drenched with my own goo.

I awoke to hear Phil and Mama come in around midnight, then listened to
them make tickles a little. But I fell back to sleep.

A warm, soft kiss and the feeling of a rough beard on my tender cheek
awakened me

It was Phil! In bed with me! For some dumb reason, I looked at the clock --
3:17 and pitch dark. What was he doing? What if Mama woke up?

But that kiss was all I really cared about, even though I was in my pink
nightie, caked with dried cum, with my Anal Amigo under the covers with me.

Still, I gasped, "But, Mama."

"She's a heavy sleeper, Sam. Especially after sex."

True. Oh.

"Would you like to suck my cock, Sam?"

Oh, again. I nodded.

Phil lay back and showed me what he had. It was beautiful! Long, fat and
uncut. With ridges and dark blue veins. And at that moment, very soft.

I inspected it carefully, including his long, wrinkled bag. I was shaking
with fear and arousal. Then I got next to him on my knees and kissed the
tip. He moved and groaned. Inexplicably, I giggled softly. I did enjoy
giving a man pleasure.

He began to harden. I licked the tip, and then took the head in my mouth
for a good sucking. But something was wrong; it didn't taste like the
"Tasty Boy." I looked at it, then at Phil.

He gave me a wicked smile and said, "You're tasting your Mama's pussy,
Baby."

That was when I knew that Phil was evil.

But at that moment, so was I. I resumed, swirling my wet tongue all around
this bad man's velvet mushroom. I wanted his sticky cream and I was going
to earn it. I soon had Phil moaning and writhing. Nature seemed to have
made me a natural cocksucker too. At least Phil seemed to think so. After
fifteen glorious minutes, Phil's balls contracted, his nipples erected, and
he blasted his manly goo onto my pretty face. I was ecstatic! I had made a
man cum -- given him pure joy. Phil looked at me. He considered kissing my
cummy face, but just thanked me and left the room.

Was that how our relationship would be? Slam, bam, cum in your face, ma'am?
Why did I want this loser anyway? I wasn't even really gay. Or whatever you
call it when a guy is a girl and likes guys.

I had to steal him from Mama. How? Then how would Mama react? Was it worth
it? My mind said no, but my genitals said yes, yes, yes.



Chapter Six -- The Week

Of course, the next morning I swore off Phil and sissying forever. I even
made a point of eying down some babes at school. Not that they noticed. But
Dennis did.

"What's going on with you, Sam?" Dennis asked. "You've been a bit whacked
out lately. Now you're sizing up girls?"

"Yeah, so?" I said, petulantly.

"It's just a different you," he said. "And I'm your friend."

He was right. I managed a smile. "Sorry, Dennis. Maybe I finally reached
puberty."

That broke the tension. I ached to tell Dennis, but my fear was enormous.

That night when I got home, I looked forward to a relaxing, non-Phil night.

Phil wasn't there, but it wasn't relaxing.

I kissed Mama. She smiled sweetly, but was troubled. Did she know I was
sucking her man's cock?

No.

"I have to go away for training," Mama said. "For a week. Beginning
Sunday."

That was in two days.

"I know you're 18, Sam, but you're still in high school and I don't want to
leave you alone. How would you feel about Phil staying with you?"

All the air left my body. I turned many colors.

Mama innocently misinterpreted the signs as my anger.

"He would only be here in case you needed anything. He won't boss you or
anything. It could be a way for the two of you to get to know each other."

Sweet goodness! There was no question of that. I gathered my wits and said,
"OK, Mama. If he stays out of my way."

I went to my room, lay on my bed and considered the possibilities.

On Sunday, Mama said goodbye and Phil drove her to the airport. Should I be
in a babydoll, stockings and heels when he came back? Would he want that?
Would I?

I staggered up to my room for a good cry. When I entered, I saw a brand new
pink baby doll with matching panties and stockings, laid out on my bed. And
a note from Phil. "I'd love to see you in these. And make-up."

I shook with fear and excitement. He's going to fuck me tonight, I
thought. And every night this week. I made a delicious little shiver of
anticipation.

When Phil returned, I was in full babe mode. I wore Phil's gifts, adding a
white garter belt and some pink, high-heeled mules. My make-up was
stunning, accenting my now-welcome beauty to near perfection. Only my short
hair diminished the effect. But very little.

I stood before him. A little virgin trembling before a big, hairy
stud. Offering myself to him. Body and soul. He accepted.

Even Phil was moved by my beauty and innocence. On four-inch heels, I was
nearly as tall as he. He kissed me, really seeming to enjoy it.

When he stopped, I said, "Thank you for the clothes."

He smiled. "You're welcome. No one ever looked better in a nightie."

I blushed. He was a flatterer too. Or I really was spectacular. I decided
to believe him.

In my smallest voice, I asked, "Are you going to fuck me tonight?"

He laughed. Then got serious. "Do you want me to, Sam?"

I thought about it. "Yes," I said. Then remembered how big he was and got
scared. But it was too late. And, I really did want his pork in my pooper.

"I never disappoint a beautiful woman. I'll fuck you tonight and every
night this week, if you want. But one step at a time. Let's go upstairs and
get on your mother's bed."

There was something evil about that too. And sexy.

I minced up the stairs in front of Phil, making sure he got a good look at
my panties. He still hadn't seen my bottom or my privates. That was about
to change.

He kissed me again, and then asked me to lie on the bed as he undressed. It
was a great show, looking at his body unfold, and I was very hot, stiff and
dripping, when he was totally naked. My panties were very crowded.

Phil looked at me, lying there in almost total submission and I began to be
afraid. My mother wasn't even in the state to protect me from this, this
man. With a big, hot drooling cock. What would I do if he were mean to me?
Could I run? How far would I get running down my street in a pink nightie,
panties and stockings? And how fast could I run in those heels. I was
helpless to defend myself too. He was so big. And hairy. Did I mention that
his cock was big, hot and drooling? Well, it was.

All I could do was submit to Phil's disgusting needs. You know what they
are, girls. Cumming in our pretty bottoms. Cumming on our pretty
faces. Cumming in our slurping mouths. Cumming on our feet and nipples and
legs. Cumming.

So, I decided that was what I would do. You know, submit to him. So I just
sort of lay there on my back, looking up at Phil submissively, with my arms
in an "I give up!" pose.

He loved it. Any man would have. They all love to play "Slave Girl and the
Emperor" and when we play along (as the slave girls) they go crazy for
us. Tgirls have always known that. Genetic women know it, but couldn't care
less.

Emperor Phil benevolently got next to his lowly slave girl and began
kissing me. My panties got even more crowded. Then Phil reached in and
extracted my stiff little dazzler. He seemed enchanted by it. Later, I
guessed that it was the first cock Phil had ever held (other than his
own). He rubbed my slick goo all around the head with his thumb and I was
ready to play any game he wanted. He kept kissing my lips and rubbing my
little dolly and the inevitable happened. I blew my sticky cream all over
the imperial hand, whimpering and bucking with the staggering force of my
rearranged guts.

The evening was going well as far as I was concerned, but it appeared my
deflowering was imminent. I looked at Phil's big, hard thing. Then I
touched my tiny hole. Something wasn't right with those proportions.

But Phil really seemed to want to disprove several laws of physics. He left
me for a few seconds, re-entering the room with every pillow in the
house. He put them on the bed, and then had me lay my stomach on them, so
that my bottom was horribly exposed to the man with the big cock and the
strong will. Ohhhhhh.

Phil rolled my panties down slowly, teasingly, to just below my sweet
globes. He stopped for a few moments to say, "Sam, you have the sexiest ass
I have ever seen on anyone. In person. In a picture. In my dreams,
even. That is some ass!"

Of course I blushed. And maybe relaxed a little. Phil rubbed my cheeks,
praising them and my beauty continually. I relaxed some more.

Phil then kissed my love pillows all over, making me squirm with
pleasure. The bad boy even licked all over the insides of my bottom
crack. Oooooh. Then he tongued my actual hole! Deeply! Double ooooooh.

By that time, I was ready to help him do that disgusting-needs stuff any
way he wanted. But Phil wanted to ensure I had virtually no pain. So he got
out a tube of K-Y jelly, put it on two fingers and slowly, achingly entered
my anus, then rubbed the goo all over the inside canal of the only pussy
I'll ever have.

I didn't know about Phil's disgusting needs, but that sure took care of one
of mine. I fired cum like a jet engine. And screamed in orgasmic release.

Oh. Oh. Oh.

Wiggling, lubed fingers in the butt would make anyone cum until they were
comatose. I was panting and gasping, thinking about what a hard cock would
feel like after the hors d'ouevres were over. How could it feel any better
than those two sweet wigglers that were onto my prostate and massaging it
slowly and carefully? I wasn't even stiff and I was feeling hot
rumblings. I looked over my shoulder at Phil and saw his expression. He was
smiling and knew exactly what he was doing. Driving me insane with animal
need. My poor limp doodle throbbed, quivered and drooled, not spurted,
about another pint of sticky cream. My gut pulled. My balls vibrated. I was
in sexual torment, then complete paradise. And I hadn't even been fucked
yet.

That, apparently, was next. But Phil was tidy. He removed the two fingers
from my ass and offered them to me for cleansing. I felt rectally empty,
but Phil could have sent me on a one-way mission and I would have gone at
that point. So I took those two raunchy fingers, soaked with lube and my
ass juices into my mouth and sucked them sensuously. I don't even remember
tasting them, so intense was my lust.

It was time. Phil rubbed my ass cheeks with his palms, got on his knees
behind me, and presented his stiff, gorgeous meat for my deflowering. I
began to weep, from both fear and need. He wedged his rammer between my
cheeks and rubbed my anus with the wet tip. It was heavenly. And scary.

Phil pushed. The head popped in. I gave a little shriek and actually bit
the pillow. It hurt a little. It was so big and I was so small. But I
pushed back for more cock. Phil gave me all he had, slowly. Maddeningly
slowly. But it didn't hurt. And that was a good thing.

So were the body-wide feelings I was getting from the first cock I had ever
had in my ass. I was a girl at last. I was being adored as a sexual
creature. And my pretty ass was being used for what it was designed for, a
cock and cum receptacle.

Phil seemed to be enjoying himself very much. It felt good to please
him. And each stroke on my tender prostate took me to never-never land. Was
I going to cum again? <Gasp, pant, sob, whimper, choke> Yes, I was. And
this one almost threw me off the earth's rotation. Every pore in my body
exploded in orgasm. I sent out cum blasts that soaked through at least
three pillows.

Phil grunted, "You are the hottest piece of ass I ever had!"

I felt proud. Then I felt squishy as Phil picked up the tempo and came,
snorting and grunting, into my formerly virgin bottom.

Unlike most 18-year-olds, I knew what I wanted to be when I grew up. A
buttfucked sissy. A frequently buttfucked sissy would be even better.

Well, I seemed to have made inroads to my ambition, because Phil was
stunned with satisfaction when he finished my anal initiation.

Phil was not a tender man, but he took me into his big, strong arms and
kissed and cuddled with me for a long time. I liked that a lot.

But I wanted more cock in my bottom. So I scooted away from Phil, got on my
knees, and fondled his cock slowly and effectively.

Then (I was such a little tramp), I took Phil's big meat into my warm mouth
and licked it all over. Phil may have been an old man -- at least 40! --
but his doodle sure got stiff when I did that. He had done so much work the
last time that I decided to help him. I faced him, straddled his hips and
slowly sat on his big boy. Mmmmmm. All the way down to the hairs.

I leaned over and kissed him with my lipsticked mouth. He liked that and
put his tongue in my mouth. That excited me so much that I bounced on his
lovepole as I tickled his ball bag. Bouncy. Bouncy. Yummy!

Phil responded by skinning my little clitty pole most deliciously. I came
in less than five minutes, drenching Phil's right hand with the sweetest
juice on earth. Phil grunted a lot, but held on until I made another sticky
mess and an intense set of love spasms. That set off Phil's second go,
which he told me was even better than the first.

As he kissed me, he told me I was a perfect angel of love. The
flatterer. Of course I loved every word, because it was true. No man could
have felt any other way about me that night.

Phil and I made love twice more that evening and I woke him up at three
o'clock with a ball-busting blowjob. He liked that too. We had to go to
school and work the next day, so I woke him up at 5:30 and had him fuck me
on my back. I liked that the best. It was the deepest penetration and the
greatest feeling of helpless girlishness. I'm not sure, but I think Phil
was glad to get away from me. I believe the man was fucked out and needed
to recharge.

Phil was in fine fettle that evening and night. He fucked me on my back;
standing up, but bent over; spoon fashion; and on all fours. And I sucked
his cock twice. Phil came six times. I made gooies fourteen times -- five
times without even getting hard. Age eighteen is the sexual prime, you
know.

How would I ever live without that? My asshole was the center of my
thoughts and very existence. I wanted it stuffed with manly meat. And manly
juices.

The third night, Phil fucked me twice when he got home early from work,
then had me dress in a lovely little black dress he had bought for me. Phil
had made reservations at a very chi chi restaurant and wanted to show me
off. I was terrified, never having been dressed in public.

My fears melted when I saw how incredibly beautiful I looked in my dress,
stockings and high-heeled sandals. Phil glowed with what I hoped was
love. Or was I asking for too much?

Heads turned as we entered the restaurant. Male and female heads. Oh my. It
was almost better than sex. If such a thing were possible. I already moved
like a woman, tottering along on my five-inch heels. The absence of boobs
made me look even more like a fashion model and my short hair accented my
beauty.

It was a good thing I had given my little girl a tight tuck. She kept
threatening to tent my skirts. All the admiration was getting to me and
suddenly, in an amazing moment of clarity, I realized that I had
options. Phil could have been one of thousands of potential admirers for
me. Millions even. I began to think of Phil as the lucky one. More so than
me. A good way for a girl to think, if she wants to make it through her
life in one piece.

Still, Phil was the one paying for dinner and the one who would be cumming
buckets into my aching pooper in an hour or two. So I flashed my 1,000-watt
smile and giggled when he reached under my dress to stroke my bare thighs
above my stockings.

Being en femme in public was a totally exhilarating experience that I hoped
to repeat several times. Although it was not to happen that week.

As I was thanking Phil properly for the fourth time for buying me dinner, I
realized that he was jealous. He didn't want to share me with anyone. Even
to be ogled. Yet, he expected me to share my mother with him. Much to
ponder.

Phil kept me home and fucked me most deliciously until Saturday morning,
when he had to go to pick up Mama. I drained his balls so thoroughly the
last time that I didn't think he would have much left for Mama. We girls
are competitive, you know.

I decided not to wait for them to come home. I went over to see Dennis.

Dennis seemed delighted to see me, since I had been getting my bottom
porked all week and didn't have a moment for him outside of school.

His parents had gone shopping, so we had the place to ourselves.

We talked about school and stuff and then Dennis asked, "What's been going
on with you, Sam?"

Easy one. "I've been really busy, you know?"

"I've been your best friend forever. I think you should tell me whatever it
is."

I looked at Dennis. I wanted to tell him. I couldn't. Then I did!

"No judgments, no telling?"

"That's always been us, you know that, Sam."

I began to cry. Inexplicably, I put my head on Dennis' chest. And even more
inexplicably, he hugged and rocked me.

Softly, Dennis said, "It's OK, Sam. It's OK."

I felt so warm and protected in his arms. My sobbing eased and I said, "I
know I look like a boy, but I'm really a girl."

Now, Dennis, who had seen my willie many times at gym and camp and stuff
said nothing, but still held me in his strong arms.

I continued. "For a while now, I've been dressing as a girl, panties and
such. And masturbating. Dreaming I was a girl and that a man was making
love to me."

Dennis shifted in his seat a bit, but continued to hold me tenderly.

"I began to make love to a man two weeks ago and I loved it." I added
quickly, "But I'm not gay. I'm a girl who likes men."

Dennis added two and two. "Phil?" Small hint of disdain at my choice in
men.

I nodded. Dennis looked at me and then changed my life forever.

He kissed me. Softly. Lovingly. Thrillingly. Better than all my orgasms
with Phil put together.

I was transported to Venus, the planet of love. But I wasn't even dressed
as a girl. Dennis solved that little problem by removing every stitch of my
drab, boy's clothing.

As he did so, he breathed to me, "I've always loved you. I couldn't admit
it, even to myself. But I've always loved you. I've always thought of you
as a girl, my girl, but how could I tell you?"

Then he began to kiss and lick my nipples as he stroked my overjoyed
clitty. I had never been so happy. My true nature had been revealed to my
true love and he not only accepted me, he was totally in love with me.

He worked me up into a frothy state. In minutes, I was cumming and
screaming his wonderful name. I groped for his cock and devoured it with my
hungry mouth. It was a great cock, attached to a fine young man. Who was
this Phil guy anyway?

Dennis wasn't trying to dominate me. He wanted to love me. And I wanted to
be loved. Although we girls do like a little dominance in the mix now and
then too.

I fondled Dennis' hairy, heavy ball sack, then licked each round treasure
until his eyes began to water. Dennis liked it very much. And so did his
thick meat, which was leaking like the White House. Creamy pre-goo. Yummy,
sticky semen. I licked and licked. Dennis threw his head back and gave me
the biggest reward I could have ever wanted. All over my pretty, but
un-girlied-up face.

We cooed and kissed and swore undying love. Then Dennis ate my ass for a
good half hour, making me lose my girlie cream twice. I begged him to fuck
me. BEGGED FOR IT! Oh, how that fired my boy up. He spooned up behind me,
drove his big guy into me and moaned with joy. I squealed his name, then
gooied yet again. Dennis was a superb lover, kissing me and rubbing my
nipples with the copious cream that I had been avidly spilling in his
honor.

When Dennis blew the biggest gusher of his life into my marvelous bottom,
we both knew that nothing or no one would ever come between us. I would
just tell that Phil character that he could stick his Johnson elsewhere.

I picked up my clothes and got dressed, kissing Dennis with the fervor of
fresh, young love. We made litanies of promises to each other. Then I went
home.

When I got home, Mama was sitting in the living room crying. I was
reluctant to get too close to her, since I smelled like the men's room at a
porno shop. But she seemed so pitiful, I hugged her and asked what was the
matter.

"Phil is gone," she said. "He didn't even pick me up at the airport. He
went to the airport all right, but got on a plane to go to his new job in
California. It's all in his voicemail the coward just left me."

The utter rat! He was just using me for sex the last week he was in
town. And I let him. Stupid, stupid, stupid. I decided to never hurt Mama
by telling her about Phil and me.

I didn't think it was sour grapes when Mama said, "I don't know why I even
bothered myself with Phil. He was hunky, but guys like him don't commit;
they're just exercise."

Mama was right again. I stopped worrying about myself and comforted
Mama. She may have noticed the smell, but didn't comment, except to say,
"You're such a good boy, Sam. I'm so lucky to have you.'

I gulped and said. "But Mama, you've been right all along. I'm really a
girl. And let me tell you all about why Dennis is very glad."



Please tell me what you think at gingerfred2005@yahoo.com

My other stories on nifty:

"Acting Up" transgender -- control
"Panty Pleasures" transgender -- young friends
"Woodville" transgender -- tv
"Mothered" transgender -- control
"Panty Town" transgender -- teen
"Tradition" transgender -- teen
"Punished" transgender -- high school
"Panty Paradise" transgender -- teen
"Kevin and Molly Go to Camp" -- transgender -- teen
"Lovelife" -- transgender -- high school
"My Three Sissies" -- transgender -- tv
"Acting Out" -- transgender -- high school
"Explorers" -- transgender -- high school
"Pantied" -- transgender -- young friends
"Rebuilding" -- transgender -- teen
"The Au Pair" -- transgender -- surgery
"Birthday Girl" -- transgender -- teen
"Genes" -- transgender -- high school
"Brothers in Panties" -- transgender -- teen
"Coach" -- transgender -- control
"Intervention" -- transgender -- high school
"Winners" -- transgender -- teen
"Teased" transgender -- high school
"Irish Girls" transgender -- teen
"Finished" -- transgender -- teen
"Role Model" -- transgender -- high school
"Freedom" -- transgender -- high school
"Panty Fiesta" -- transgender -- control
"Experiments" -- transgender college
"One Fine Day" -- transgender -- teen
"Stiff Resistance" -- transgender -- teen
"Poker" -- transgender -- tv
"Panty Sabbatical" -- transgender -- high school
"Published" -- transgender -- tv
"Stripped" -- transgender -- high school
"Trained" -- transgender -- control
"Something Better" -- transgender - tv
"Fulfilled" -- transgender -- tv
"Private Matters" -- transgender -- high school
"Hard Times" -- transgender -- tv
"Girl Nights" -- transgender -- control
"Geography" -- transgender -- tv
"Somewhere" -- transgender -- high school
"Next Door Bride" -- transgender -- chemical (though I don't think it has chemicals)
"Service" -- transgender -- tv
"Test Driven" -- transgender -- tv
"Sissy Stepmother" -- transgender -- tv
"Slacker Moms" -- transgender -- tv
"Sissies and the City" -- transgender -- tv
"Paid in Full" -- transgender -- tv
"Alternative Education" -- transgender -- control
"The Boy Bride" -- transgender -- high school
"Stiff Competition" -- transgender -- teen
"Reservations" -- transgender -- tv
"Panty Pride" -- transgender -- tv
"The Panty Life" -- transgender -- tv
"Super" -- transgender -- tv
"Stocking Boys" -- transgender -- tv
"Panty Secrets" -- transgender -- tv
"Auntie's New Panties" -- transgender -- tv
"Good Riddance" -- transgender -- tv
"Generations" -- transgender -- tv
"Fully Fashioned" -- transgender -- tv
"Tommy's Summer Job" -- transgender -- tv
"Tuition Assistance" -- transgender -- tv
"Sweeties" -- transgender -- young friends