Panty Pleasures, Tranny Stories

Panty Pleasures, another hot tranny story

Chapter One – Nerds United

My name is Mickey Donaldson. For most of my 16 years, the kids have called me Mickey Mouse, because of my size and because of my shyness. I was only 5’3″ and at 115 pounds, very skinny. My best friend Jeremy Haskins and I were always the oddballs. Jeremy was a little bigger at 5’4″ and 120, but we weren’t being recruited for our high school football team. Chess team was more like it.

We were pretty much classic nerds. Shy. Picked on. Ostracized. Intelligent.

But we were still 16-year-old boys and our hormones were stirring. Boiling
actually. Jeremy and I were both virgins and hadn’t even really whacked our
weenies. The girls in our Junior Class wouldn’t even look in our direction.
We were below all their standards and believe me, they weren’t all
beauties.

Jeremy’s sister Alice was a cute 14-year-old babe who wouldn’t give me
directions out of an avalanche. Jeremy used to ask her for some
introductions to her friends, but Alice turned him down every time. She
said her reputation was at stake.

I often wondered how Alice could be so attractive as a girl, while her
brother Jeremy was so unattractive as a boy.

We seemed doomed to lifelong celibacy until the turmoil kicked up in the
Middle East again.

My mother’s younger sister Beth and her husband Hal were journalists. They
and their three cats had a nice two-bedroom condo in the good part of town
and were already doing well for themselves when they got the big call. A
cable television network wanted them to spend at least six months in the
Middle East reporting on the troubles.

That presented a problem for Aunt Beth and Uncle Hal and a life-changing
opportunity for me.

Aunt Beth told my Mom and Dad that it would be a good idea for me to “keep
an eye on things” at their apartment while she and Hal were gone. I could
drive over there every day (had my license), water the plants, sort the
mail for important stuff, feed the cats and spend some time with my feline
cousins, so they wouldn’t be lonely. I didn’t like cats very much, but as
it turned out, the requirement to “spend some time with them every day”
turned out to be my big break.

Since I had never given my parents a whiff of trouble, they readily agreed
to Aunt Beth’s request. Mom said it would help me become more responsible.
I was already drowning in good behavior. It was time to start acting like a
teenager.

Oh my. I would have access to my very own stabbin’ cabin! Only problem was,
there were no babes I could stab.

What to do?

Well. I decided to start off slowly. The first day that I went to Aunt
Beth’s, I figured that my duties would take me about 15 minutes of the
three hours I could spend alone and unsupervised each day. That left two
hours and 45 minutes for the worst kind of mischief, which when I first got
there appeared to be leaving a soda can on the counter instead of in the
garbage.

I was 16. Surely I could do better than that.

Oh my. They had a computer. My family did too, but it had so many
stranglingly strict parental controls that if the site didn’t have Disney
in the title, I couldn’t get to it. Plus, it was in the living room, with
the screen facing anyone who walked in. If I wanted to look at big-busted
babes making some tattooed guy happy, I was out of luck.

But my aunt’s and uncle’s computer was right here, with, I hoped, no
controls. And I had free access.

Maybe it was only a shell. I thought. Maybe it didn’t work. I turned it
on. It worked. I tried the Internet. On! A search engine for, let’s see,
“nylon babes.” Looked like 10,334,575 choices, but would I have access?
Double click on “Nylon Honeys.” It was thinking. I hope, I hope.
Halleluyah! There they were in all their nylon babishness!

I was getting very excited. The world’s porn was at my fingertips and I had
two hours and 45 minutes each day to explore it. My poor, virgin cock was
straining at my jockeys. I knew I must never mention this to my parents. Oh
no. It will be my secret. And Little Mickey’s, of course.

I patted the little guy and promised him better times ahead. But those
first hours, I didn’t even touch him. I was in such wonder at the
possibilities. And the babes.

An hour before I was to leave, I decided to log off and do more snooping.

Aunt Beth and Uncle Hal had obviously left a lot of stuff they didn’t think
they would need behind. Aunt Beth was a very pretty 32-year-old woman who
apparently loved to wear girlie things. Her drawers were full of lingerie
and stockings and her closets were full of minidresses, miniskirts and very
sexy shoes, none of which would have been appropriate on assignment.

She also had two big drawers stuffed with the prettiest panties – every
shape, style and color. I felt them with my hands and got very stiff “down
there.” I hoped this wasn’t an incestuous thing for my aunt. I didn’t think
so. But the sight of all her panties excited me horribly. Why? I didn’t
have a clue.

I held a pair of pink satin bikinis in my hands and lifted my shirt,
rubbing them on my skinny tummy. Odd. But it felt so good. I wanted to feel
them on my legs, so I pulled down my pants. Oh, they were so cool and
sensuous against my smooth thighs. My cock was twitching. I felt so dirty,
but I had to see what it was like, so I pulled down my white cotton briefs
and gently, teasingly rubbed the silky unmentionables against my red,
throbbing cock.

For the first time in my life, I felt the call of the wild. My stomach
lurched. I was a little frightened, but kept rubbing. My toes curled. I
could feel my nipples harden. How strange, the thought flashed through my
mind. A nanosecond later, my balls projected five, thick, hot, sticky
spurts of my virgin sperm into my silky tormentors. My knees buckled, but I
kept my balance. I trembled in an agony of release. I had heard about
orgasms, but the reality outstripped the hyperbole.

Oh, Baby! So this was what I had been missing.

And those panties triggered it all.

Even though Aunt Beth wouldn’t be back for six months, I took no chances. I
washed the thick cum from the little teasers and hung them to dry.

How do women walk around wearing those things? I would be cumming all the
time.

It was time for me to go home. Impulsively, I slipped two pairs of silky
prickteasers into my coat pocket, said goodbye to my cousins, and left.

Chapter Two – Panties for Mickey

As I drove home, I actually imagined that the panties in my pocket were
giving off heat. Having tasted forbidden fruit, I wanted the whole orchard.

Was I weird? Or gay? I hoped not. I mean if you rub a woman against you and
you cum, that’s not gay. So why would it be gay to rub a woman’s panties
against your boy pole until your goo leaped out?

It had felt so good when all that cream evacuated. And it was so easy to
do. It was as if the panties had some magic in them. Like Frosty the Panty
Boy. He put on the panties and his icy cock began to dance around.

When I came home, my mother was all smiles. She was happy to see me doing
something good for someone in her family. Plus she seemed really happy that
her sister now owed her. Debts and potential payback are always prized in
any family. And Mom always said my life needed more structure.

My life was connected to my cock at that moment. I wanted to see where this
sexuality thing took me.

As I lay in bed that night wondering what it all meant, the phone rang. It
was Jeremy asking how it was hanging. If he only knew.

“So Mick, that’s a pretty good deal for you alone in an apartment all
afternoon. We could bring girls up there, don’t you think?”

“If we had girls to bring,” I said sadly. “Plus, I’m not really supposed to
bring anyone in.”

“Even me?” my best friend asked.

“Technically no, but I’m tired of being a perfect kid. You can come
over. Just give me a couple of weeks to make sure the parental units aren’t
snooping on me.”

“Cool. Later.”

“Later.”

I wondered what Jeremy would think if he knew I had made a big load of cum
in my aunt’s panties that afternoon. I was tired, so I shut the light and
went to sleep.

The next morning after my shower, I decided to try wearing the
panties. Just to see if they fit. I chose a pair of silky, pink, string
taunters with a triangle in front and one in back. Oh, they felt good going
on. And they fit perfectly. My little guy was enjoying his new home and my
wrinkled little bag of grapes was smooth and comfortable. Could I stay
“dry” all day with them on? I didn’t have gym that day, so I risked
discovery to find out.

I never felt so naughty. All day I was wondering if people could tell I was
a panty boy. No one acted any differently to me. Which wasn’t very
good. They weren’t mean, but I was in the out crowd’s out crowd. And so was
Jeremy. At lunch, he chattered on happily about some new video game. All I
could think of was the games I would play with my cock when I was alone
with that porn-rich computer and 63 pairs of panties.

After school, I rushed over to the condo, fed the grateful cats and emptied
their stinky box, brought in the mail, threw out the junk mail and resumed
my snooping.

An equal-opportunity privacy violator, I looked through Uncle Hal’s
things. My expectations were much lower, but I was very wrong. Way back in
his closet, hidden under boxes of shoes, was a loose floorboard. I lifted
it up and found gold — a large stack of printed porn. Classic stuff and
new. I loved babes in stockings and apparently so did Uncle Hal. My cock
was rubbing hard against the pink panties. I was just about to attend to
that when I saw a second floorboard lower than the first. I pulled. It
gave. More porn. But very different. This was filled with beautiful women,
but they had something the women in the first batch didn’t have — cocks
and balls!

Was Uncle Hal gay? Women with cocks and balls? Beautiful women? Ohhhhhh. I
shuddered and came hard in my skimpy panties. How did that happen? I didn’t
even touch myself. Something deep inside me was profoundly affected by what
I had just seen.

I gathered the “special women” materials for further study and put the
“pussied women” stuff back in its place. Then I had to clean up the big
cummy mess I had just made.

Reluctantly, I set the educational material down and washed the panties,
replacing them with a pair of lacy black girliepants. Mmmmmmm.

I spread a few towels on the bed, removed all my clothes except for my
black panties and lay down.

There must have been forty books, magazines and comics. All with very
feminine people sporting masculine pubic areas.

About half was stuff about she-males. I had never heard of such people, but
many were as gorgeous as any woman who ever lived. Big, tasty boobs, slim
waists, wide hips, pretty faces and mostly large, usually erect, always
pretty cocks. Many appeared to be Brazilian or Thai, but there were
she-males of European and African heritage as well.

I began to stroke my pantied crotch. Ohhhhhh. I was very excited. I locked
eyes with a Brazilian doll with a sweet face and a huge, wet cock, skinned
and hard and curved like a banana. I wanted to kiss that cock so badly. I
wondered how it would taste. I had never tasted cum. I would take all of
that cutie’s cum in my mouth and……Oh….Ahhhhhhhhhhh. I arched my back
and messed my panties very badly.

I lay there breathing hard and rubbing the cum puddle through the
panties. I skinned the little wispy things down just below my balls and
looked at my red, drooping cock. It was slick with cum, but it appeared
very happy. I had no idea when the next gusher could occur, but I decided
to find out.

I gathered up the cum in the fingers of my right hand and massaged it
lovingly onto the tip of my little boy. He liked it a lot. Even my soaked
panties felt good on my thighs. Blushing from the naughtiness, I licked
some cum off two fingers, tasting the salty ambrosia for the first
time. Yum! I liked it.

With my left hand, I picked up a book randomly from the stack. It was not
about she-males. It was called “Panties for Peter” and said it was an
illustrated TV novel. TV? Oh, yeah. Transvestite.

Only I would look that closely at a time like that, but I saw it was
copyright 1969. A classic. It was the story of a young man named Peter
whose mother decided to make him into a young girl named Petra. The
illustrations were very detailed and very stirring.

Peter was a pretty young fellow of about fifteen who was led step by step
into feminine joys. He resisted at first, but when he surrendered, he
became a beautiful young girl who was worshiped by young men
worldwide. There was no sex in it, but don’t tell little Mickey that. The
picture of Peter sitting at a vanity, with his blonde sausage curls,
applying mascara to his long, lush lashes made me shudder and spurt a quart
of my precious cream.

Good golly it was intense. Why did that happen? I looked at more of the
pictures, while continuing to rub my exhausted cock. Peter was wearing tiny
bikini panties, a bra, and a peignoir. His face was heart-breakingly pretty
and he was looking over his shoulder to check the seams of his sexy black
stockings, which were held up by the laciest garter belt. He had very
high-heeled pumps on. I thought, that could be me. And even though my
little guy was still soft, he blew another load all over my soaked
tummy. Oh, mama.

Those were gay thoughts. I didn’t want them. Away. Icky bad.

I toweled myself off, cleaned up, stashed things away and went home,
dreaming dreams I had never dreamed before.

Chapter Three – Discovery

I was a troubled boy over the next 21 hours. I needed answers I couldn’t
get to until I went back to the condo. The Internet was the Rosetta Stone,
I knew it.

I did my duties first, then looked up transvestites on the Internet. I
learned that transgendered person or TGs were the preferred terms. And I
learned that I apparently was not alone.

Many, many people had transgendered feelings and desires. In fact, a German
psychologist named Manfred Ginger (rhymes with “finger”) believed that all
men were part woman, based on the presence of their X chromosome.

Still, if I went to school one day and showed my panties, I doubt if
quoting that Ginger guy would help.

It was amazing, though, to see the transformations. Boys and men became
gorgeous girls and women. I only had about an hour left, so I decided to
take a little test run of my own. I rooted through Aunt Beth’s lingerie
drawer and found a gorgeous blue babydoll nightie and matching bikini
panties. I removed my clothes and put the nightie and panties on. Looking
in Aunt Beth’s full-length mirror was an eye-opener. My hair was short, my
legs were bare and I had no make-up, but I looked h-o-t-t hot!

I turned and posed, teasing myself “down there” as I marveled. I had
observed women’s movements long enough to know some mannerisms, so I
imitated them. I tossed my head and turned this way and that. I bent over
and pulled my panties down to expose my nicely turned ass, which, despite
my skinny frame, had a pleasing plumpness.

I was very excited looking at myself like that. A little scared too, but
mostly excited. I pulled my panties back up and touched myself through
their soft silk. Seeing a girl in the mirror who was me. All hot. And
cute. And….oh. I felt that little tingle that meant the Big Visitor I had
come to adore was on his way to my balls…Ah….He was getting
closer. Eeekk…..He was in the driveway and…….SLAM! in the front door
and wrenching cum from my little tee tees, through my little-girl clitty
pole and into my tiny panties. The cum was drooling from either side of my
silky little girliethings and cascading down my thighs.

I loved cumming so much! But why was I starting to talk like a girl?

The next day, I decided to see what this make-up thing was all about. Aunt
Beth had a millennium’s worth on her vanity table. I guessed our coloring
was similar, so I got some instruction from the Internet and tried some
foundation. Not bad. I brushed on some blush. That brightened things up a
bit. The eyes were more difficult, but I was persistent and what I saw
after 45 minutes of trial and error was darned pleasing. I was pretty! With
some work, I could be quite pretty. It was so exciting. I wanted to try on
some stockings, but the Web site I had come to trust said I should shave my
legs first.

My cock was hot and throbbing the whole time I shaved my legs. It was just
such a feminine thing to do that it excited me no end. I finally had to
stop and massage my cockhead until all that cream left my balls and gave me
a little peace so I could finish shaving.

I dried off and took a doughnut-rolled, black stocking in my hands. I
touched my right toes with it, idly thinking how much better my toes would
look manicured and painted. What was happening to me? I rolled the stocking
slowly, ever so slowly up my smooth, shaved leg. Every pore of my leg
strained to feel its silkiness. I was breathing heavily when I snapped its
stay-up top to my thigh. My cock was hard and aching yet again. I rolled
the other stocking up my left leg. Mmmmm. How do women do this every day
without cumming in their panties? My cock was dangerously agitated. I
padded over to the full-length mirror with my made-up eyes drinking in the
sight of me in panties and stockings. Too much. Blooey! My cock sprayed the
mirror with hot goo. I shook like a wet dog.

I was looking at a flat-chested but very hot girl. With gooey, bulging
panties. And a very pretty face. Oh man, I thought, I’m not an ugly
duckling any more. I’m hot. All the girls will…….The girls will do
nothing. What straight girl would want me like that?

I blinked. And had an evil thought. But the boys would. Would I want the
boys? Not the ones I knew. Except for one.

Chapter Four – The Exception

In days to come, I perfected my make-up, worked on my mannerisms and
learned to walk in heels. In four-inch heels, I was a statuesque five-foot
seven.

After three weeks, I told Jeremy I thought the coast was clear and he could
join me at the condo that afternoon.

He was right on time, arriving just as I had done my cat duties. I got him
a Coke and showed him the incredible stack of non-cocked female porn I had
found.

“I’ve been jerking off to it, Jeremy. Have you ever done that?”

Jeremy blushed and said that he hadn’t.

“That’s OK,” I said. “I’ll show you how.”

Jeremy squirmed a little, thinking I was going to whip my weenie out and
give a jerk-off demonstration. But that was not my plan.

I shucked my pants, being careful not to let him see my lacy white panties,
then asked that he remove his. Jeremy was nervous, but excited.

“My aunt has so many pairs of panties you won’t believe it. I just look at
these magazines and rub my cock with her panties and the next thing you
know, I’m cumming. Have you ever cum, Jeremy?”

Poor Jeremy decided to tell the truth to his best friend. “Not when I was
awake.”

“Then you need my help.” I handed him the sexiest book in the large pile,
opened to a cum-stained page and sat next to him.

Jeremy didn’t expect that. Nor did he think I would wrap a pair of Aunt
Beth’s pink panties around his very stiff cock and begin to wank it
expertly.

Jeremy looked at me with fear and lust. I acted as if what I was doing was
perfectly normal.

“Aren’t those pictures great, Jeremy? Look at those legs. She’s so
pretty. And her pussy is so hairy and wet. Do you like the feel of the silk
on your cock, Jeremy?” He grunted and looked at me with eyes desperate for
me to continue.

I stepped up my efforts. “Imagine putting this nice hard cock right in that
hot, wet pussy. She would be moaning for you, begging you to fuck
her. Deeper. Deeper. Oh, Jeremy. I think you like this. Oh.”

Spurt after spurt of Jeremy’s virginal cream exploded into the lacy pink
panties. His eyes filled with tears and he looked at me in helpless
gratitude as I milked him dry.

“I’m glad you liked that, Jeremy,” I said. “I think I’ll look at some of
these magazines now.”

Much to Jeremy’s amazement, I grabbed a skin book, sat on the other end of
the couch and began to massage my cock with the same panties that were
filled with Jeremy’s cum. His cum was still hot and it felt wonderful. Cum
is the world’s best lubricant. My excitement was intense, especially
knowing that I had grossed out and delighted Jeremy in equal parts. I was
soon cumming into the sperm-drenched little garment, making little
delighted squeals that had Jeremy hard all over again.

Much to my delight, Jeremy took the double-loaded panties back from me and
used them on himself to produce his own stunning cum.

Not to be outdone, I took the wet wankers back and dropped a forth cummy
load on the overtaxed lingerie. There wasn’t a dry spot on them, but they
had served their purpose well. I knew Jeremy would be up for anything I
proposed.

That was enough for the first day together.

Chapter Five – Out

The next day, I made sure I was ready for some different kinds of fun.

When Jeremy arrived at the condo, I had what I needed stashed in the
bathroom and a lot of magazines from the “special girl” group mixed in with
the mainstream porn.

Jeremy followed my lead by removing his pants and underpants. I suggested
that we try masturbating without panties wrapped around our cocks that
day. He seemed a little disappointed, but still very hot to trot.

Seated at the opposite end of the couch from Jeremy, naked from the waist
down and scarily erect, I watched him make his literature selections. As I
hoped, he was very interested in the she-male stuff, but wonder of wonders,
the first thing he took to stir his stones was “Panties for Peter.” That
was a very good sign. Jeremy looked down at me guiltily to see if I thought
he was gay for his book choice. But I pretended to be absorbed in a
magazine about crossdressers called “Ladylike.”

Jeremy got very aroused very quickly reading about Peter becoming a sexy
little muffin. And when he reached the picture of Petra walking high-heeled
and proud into her school, in full feminine beauty, with boys staring in
horny wonder, he whimpered and came hard, puddling on his tummy and chest.

I excused myself and went to the bathroom, where I quickly applied my
make-up, slid on my pink, seamed stockings, slipped on my pink babydoll
nightie, omitting the panties, and added a long blonde wig of Aunt
Beth’s. Fourteen minutes was all it took. I didn’t want Jeremy using up all
his spermy resources before I got any, so I was in a rush.

I slipped on pretty, pink, four-inch mules and sissied out to a new life.

Jeremy didn’t look up at first, so intent was he on discovering Petra’s
ultimate fate. When he did look up, it was a Daffy Duck double take, with
bulging eyes and tongue on a long roller. Well, almost. But he was excited.

I minced over to him, sat next to him and scooped up a tiny bit of the cum
that was a half-inch thick on his stomach. I tasted it and said, “Yummy. Is
there any more of that for me in there?”

Jeremy trembled with fear and lust. “Mickey?” was all he could say.

I kissed him. Then I looked in his eyes and said, “It’s Sarah now, Honey.”

He stared. I wet my hand with the cum on his stomach and used it to tease
his prick to a new hard stand.

He kissed me, adoring me with all the love we had as friends, now
transcended to that of lovers.

I gasped. It was so wonderful.

Jeremy reached for my little clitty. She was stiff and sore with need. He
kissed me as he skinned the fiery head. I moaned and that spurred him on. I
hadn’t cum that day and the excitement had me cornered. I was going to cum
all over his fingers. I couldn’t tell him because my mouth was full of his
tongue. I squealed very nicely for Jeremy and sprayed his fingers with my
girlish juices. Mmmmm.

Jeremy hadn’t cum yet, so I slid to my knees and took his cum-drenched
little guy in my mouth. Jeremy liked that, especially when I rolled my
tongue on all the good spots and felt his balls up really nicely. I had
become a cocksucker and apparently a very good one, because, despite
who-knew-how-many cums that day, Jeremy produced four delicious gobs of
cream and some nice sounds of ecstasy.

We had about an hour left when Jeremy returned to earth. “What just
happened, Mickey, I mean Sarah?”

“You just met a new girl who’s hot for your body. That’s not so bad is it?”

Jeremy hesitated, then said. “It was the best thing that ever happened to
me. But it was so gay.”

I smiled. “Love between a boy and a girl is never gay, Jeremy. And right
now, I’m a girl. A girl who would really like her clitty sucked just like
she sucked your cock.”

Jeremy looked at me briefly, considered his options and made the only sane
choice. He got on his knees took my stiff little girl in his mouth and
licked her lovingly.

Oh, that warm, wet mouth on my sensitive clitty pole! It was
fantastic. Jeremy was a natural. He even massaged my asscheeks as he sucked
me. That was a nice touch. When he put his middle finger at my tight little
hole and entered to the depth of his nail, I screamed and released all my
hot girlie cream all over Jeremy’s sweet lips and face. He was a bad boy to
do that! I wanted to hold off a little longer before I made a cum. That was
when I knew that my asshole was very sensitive and sensual.

I forgave Jeremy though, and helped him lick my cum off his face. Some of
it I fed back to him in a sweet series of kisses.

“How did you know to do that to my little tushie hole,” I asked sweetly.

“No parental controls on our computer,” my smart friend answered.

I kissed him some more. He kissed back.

As we were getting dressed to leave, Jeremy said, “I can’t believe we did
all that. Can we do it some more tomorrow?”

What a sweetie he was.

Chapter Six – In

The next day, I decided I was going to ask Jeremy to take my virginity. It
was getting in the way of some real fun anyway and I wanted to feel a cock
in my secret place. The girls in Uncle Hal’s books all took huge cocks in
their asses and smiled so sweetly that I figured it must be fun. My
Internet gurus recommended plenty of lubrication, however. I knew just the
thing — Aunt Beth’s vaginal jelly. It was slippery and smooth, just the
thing to ensure painless arrival of Jeremy’s big boy in my hot tunnel.

I told Jeremy at lunch in school that he could pork my little pooper that
afternoon and he almost fainted. He wanted to take me into a broom closet
or something and do it right then. Didn’t he know that that would be gay?
Gee. You have to know your rules about gaiety.

I flew through my cat duties that afternoon and was girlied up very nicely
when Jeremy arrived at the appointed time. I was wearing virginal white
lingerie – panties, stockings, garter belt, bra stuffed with stockings and
four-inch sandals. I sneaked a peek at my legs in the mirror. They looked
great — all toned and sexy. And the heels made my butt stick out in open
invitation for a good fucking. I hoped Jeremy would RSVP.

Jeremy’s eyes got real big when he saw my pretty face in full make-up. My
eyes were bedroom-strength and my lips were in full cocksucker mode.

He kissed and hugged me really sweetly, even slipping his right hand into
the back of my panties and massaging my soft cheeks. I purred more than my
cousins did.

I asked Jeremy to get naked and he did so post haste. Jeremy had a slim,
sturdy body, just like mine. I couldn’t help thinking that with a little
coaching from me, we would be two hot babes. But for then, I wanted a hot
cock, attached to a boy named Jeremy.

“I want you to fuck me today, Jeremy. I want your hot, hard cock to slither
in my tight hole and slide in and out, in and out. I want you to make me
cum, then cum into my ass with all your manly juices. Will you do that for
me, Honey.”

The poor boy was dragging his tongue along the floor.

We did some outstanding naked kissing — one of life’s great pleasures,
whether or not it yields fluids. We were teasing each other’s yummy poles
with our fingers as we kissed.

Jeremy and I discovered the joys of nipple licking as well. The sweet boy
lifted my bra and licked my puffy nipples ever so gently as he fiddled with
my clitty. The boy had real potential. We were in a major dither in about
20 minutes.

I ran into my aunt’s and uncle’s bedroom with Jeremy in hot pursuit. I
handed him the jar of vaginal jelly and explained its uses. Then I lay on
my stomach, stretching my small frame diagonally on the bed. I arched my
butt, giggled and gave it a sexy little wiggle.

Jeremy needed no further instructions. He lubed up the middle and index
fingers of his right hand, leaned over to kiss the back of my neck and
slowly, carefully inserted his middle finger into my very tight sphincter.

Ohhhhhh. It was very, very tight in there, but he relaxed me, working in
and out. It felt wonderful but I was worried what a larger object, such as,
say, a cock, would do to it. My enthusiasm waned a millimeter, then I felt
the second finger. That stretched me a bit more and it was a very pleasant
feeling. Mmmmmmm. Very pleasant. Stretching. Back there.

I was getting used to my two new friends when they left me. I made a pouty
face, but then realized that they were in the way of a friend I had met the
day before. Jeremy’s cock was poised for insertion. It was a nice four and
a half inches. Not bad for a guy our size. Mine was a teeny little weenie -
only about three and a half inches.

I felt Jeremy’s first inch enter me and my eyes filled with tears. It
wasn’t entirely pleasant, but Jeremy was being gentle and loving. Two
inches and I felt it *pop* through the ring. Better. Nice. I got to my
knees to give him a better angle. Three inches. Liftoff. I was being
fucked. It was outstanding. I looked back at Jeremy and gave him my blazing
smile of encouragement, which translated into, “Oh yeah, Baby. Fuck me
now. Hot and hard.” Or words to that effect.

Jeremy established a rhythm and I sang his tune. He was on top of me, his
chest to my back, which wasn’t the best position we later found out, but it
was getting the job done that day. I loved the warmth of his body. I loved
the friction in my butt. I loved the delicious feminine feelings I had as
my guy was penetrating me.

My asshole was very sensitive indeed and it was sending urgent signals to
my cock and balls that the cum should stand by to abandon ship. It was a
little thing that set me off. Jeremy gripped my hips and caressed them just
right. I felt my orgasm in my entire body. My eyelids orgasmed. But the
biggest jolt was in my butt, not my clitty. It was as if my anus ring had
been clasping a jackhammer. It turned me inside out. And Jeremy hadn’t even
cum yet.

His witness to my pleasure gave him the jolt he needed to evacuate his own
balls. Though Jeremy’s first cum had been only 24 hours ago, he was well on
his way to being an excellent lover who loved excellent loving.

I felt the first hot load my little butt ever experienced and my eyes
filled with tears. Happy tears. I was a nerd no more. I was about to have
more great sex than the cool crowd ever dreamed of.

After, Jeremy and I lay on our backs, snuggling. His cock was limp and
drooling little globs of cum. Boygoo was slithering from my gaping ass. I
was so happy. I told Jeremy he was a very good lover. That made him stiff
all over again. Jeremy and I had lived a life starved for praise. It was
good for us to have each other.

I told Jeremy that I would lie on my side if he thought he wanted to put
that big stiff boy to work again. Jeremy smiled a very unnerdy smile and
spooned up next to me. He entered my ass slowly and I gasped with joy. It
felt incredible. No pain. All gain. We stretched our loving that time to
twenty minutes. The rogue frigged me beautifully and made me cum into his
soft hand twice before my ass muscles sent him on the midnight train to
paradise.

I wondered if those in-crowders on the football team were enjoying their
afternoons as much as we were.

Chapter Seven — A Change in Plan

Over the next three weeks, I was fucked more than a bride on her
honeymoon. Jeremy was insatiable, the bad boy. He had shed his nerdishness
like an unneeded skin and had become a smooth, confident lover.

I loved when he had me on my back with my legs up in the air and was
plowing my little butt. I felt so helpless and girlish. He was my
master. The master who was emptying his endlessly replenished cum bag four
or five times a day.

I was able to convince my mother that it was OK to have Jeremy over on
Friday and Saturday afternoons and evenings, because she knew we were good
kids and would only watch TV and stuff. We did watch TV now and then, but
only to give our balls time to recharge.

We would spend an unhurried seven hours on Friday and ten on Saturday
loving each other to the fullest. We took soft, soapy baths together in my
aunt’s and uncle’s deep tub. I was naked, of course, and was worried that
it would seem too gay to Jeremy. But he was blind to all but his love for
me.

I counted during one Friday and Saturday. I came twelve times and Jeremy
came eleven.

I loved sucking Jeremy’s cock. I would lick his precum and use his cockhead
to slather it all over my made-up cheeks. He told me I was the prettiest
cocksucker on earth. I tickled his balls and even squeezed them gently from
time to time. Jeremy moaned a lot and praised my beauty and skill. I always
knew when my boy was going to cum. I felt a little rumble in his gut and in
less than a minute, blooey!

Sometimes I liked to try and swallow it all, but mostly I liked to take his
big load right in my face. I would lick his cockhead furiously as his
orgasm approached, then close my eyes and squeal with delight as he blew
big, sticky gobs of his cream on my pretty face. He said I was the
prettiest when I had a faceful of his hot goo. All guys say stuff like that
so you’ll keep taking it between the eyes.

Jeremy loved to suck my little titties. <Giggle>. They were really only
puffy nipples, but he called them my titties. He worshiped them, just as he
did my tender balls and my tiny clitty, with its long, brown foreskin
concealing my pink jewel. Jeremy became an excellent clitty pleaser,
kissing and licking me to furious orgasm at least twice a day.

My other eruptions came from being lovingly and enthusiastically
fucked. Jeremy was a terrific lover. He was a natural talent and was always
intent on bringing us both pleasure. As he filled me with his love, Jeremy
would frig me sweetly, kiss me and tickle my balls and sensitive nipples to
distraction. Sometimes I would cum twice just during the extensive foreplay
we always began our love sessions with.

His only fault was that he was a bit indiscreet. I told him that we
couldn’t have any of our fun at school, but he seethed with lust every time
he saw me. I hoped no one noticed. They probably didn’t, since we were
usually ignored. But he always wanted to take me into the boys’ room or an
empty room or corner and kiss me. He even sucked my clitty a few times
right in school. It was very bad and dangerous. But very exciting
too. After a while, I stopped thinking of it as gay.

One Saturday, after some proper warm-ups, we began with a slow, loving,
on-my back fuck that lasted almost an hour. After that, Jeremy told me that
he loved me. He was so cute. I loved him too, and said so. Then I ruined
the mood by telling him that in four months, the good times could be over.

That sobered my man up a bit. He said, “Then I’d better not waste any more
time. Sarah, would it be OK if I tried on some panties and other, you know,
things, too?”

Wow! How did I feel about that? I didn’t know. I loved having a
boyfriend. But even if he dressed all the way, we could still have sex as
girlfriends. I asked, “Why do you want to do that, Honey?”

“I need to know if I’m, you know, like you. I see you being a beautiful
girl and the thought excites me. A lot. We can still make love no matter
what I wear.”

“Of course, Sweetie. There are more than 60 pairs of panties here. Which do
you like best?”

Jeremy blushed. “They’re all so exciting, but I like these.” He held up a
sweet little pair of flesh-colored, silk, bikinis, trimmed with white
lace. They were adorable!

I worried that they wouldn’t fit. They were just a teensy snug, but that
only made the poor boy’s cock very excited, which made them really snug.

I kissed him sweetly and rubbed the front of his little panties. He filled
them right away with a big, cummy mess. He liked those panties.

He was whimpering softly as he came. I asked, “Are you all right, Honey?”

“I’m just scared, Sarah. What does this mean?”

“I don’t know, Sweetie. Would you like to find out?”

He gulped out a yes.

I took his panties off, licked him clean, then gave him a fresh pair of
blue boyteasers. The licking and the pretty panties had him all stiff again
and I wasn’t able to get them on, so I gave him a nice paralyzing blowjob
to relax him a little.

He looked so cute in those little sweeties that I gave him a big hug. I
wondered if he liked his nipples licked, as we girls did. So I gave a
tentative tongueteaser to his right nippie. He arched his back and got hard
all over again. Wow! I slipped my hand down the back of his panties and
entered his anus with my finger. I doodled around back there and began to
kiss and lick his left nipple. He blew another big load. Oh my. At that
rate, we would be all out of clean panties in another 14 hours.

Jeremy was trembling with the emotions and sexual excitement of the past
few minutes. I asked if he would like to try on some stockings. He nodded
meekly and I led him to the bathroom for some shaving. The overexcited
sweetie came again during the shaving. Of course my licking and kissing his
cock several times during the process may have been contributory.

Shaved and in his fourth panties of the day, Jeremy sat as I rolled each
black stocking up each smooth leg. Jeremy quivered with excitement and was
once again hard as Gibraltar. I hooked a black lacy garter belt on him and
escorted him to the full-length mirror. He gasped with delight. And he
didn’t even have make-up on. Well, I fixed that, seating him at the vanity
and dolling him to perfection. I fitted him with the two-inch heels I wore
the first day, slipped one of Aunt Beth’s blonde wigs and pink nighties on
him and helped him sissy to the mirrors once again.

Jeremy was enthralled with his own image. He appeared to be a very pretty
and cute young girl.

He moved this way and that, almost believing that it was a trick and that I
had hired a real girl to stand in an empty “mirror” case and mimic his
movements. Like a Marx Brothers movie. As he became convinced of his beauty
and femininity, I stood behind him and reached around his hip. We both
looked in the mirror as I extracted his cock and balls from their silky
confinement.

“What a pretty girl you make, Honey,” I said to my best friend. “Look at
those beautiful eyes.” His cock was throbbing in my tender grip. “And look
how good those legs look in stockings and pretty heels. You can wear higher
ones later. When you walk down the street all the boys will look at your
legs and ass and gorgeous face. They’ll all want to kiss you.” I rubbed
Jeremy’s cock harder and it twitched. “Then they’ll want to lift your
skirt, pull your panties down and put their big cocks right here.” I
entered his anus with two fingers and he blew the biggest load of the
day. Where did it all come from? He was whimpering and trembling with the
impact of the release. And the mirror was going to need some attention.

The poor guy was exhausted. I led him to the bed and kissed and hugged him.

“Do you want to see what it’s like as a girl for a while when we’re here at
the condo, Sweetie?” I asked.

Jeremy nodded meekly. It was as if he were already a girl. And a submissive
one at that.

“Do you have a girl’s name in mind?”

“I like Kristen, or Krissi,” the sweet little girl said. And she fell into
a contented sleep.

Chapter Eight – Two Hot Girls

Well Krissi turned out to be the girliest girl of all. She was an A number
one sissy. She adored wearing the frilliest things and made a big cummy
mess almost every time she put on panties.

Of course she started wearing panties and stockings to school and
everywhere else. It was a link between the false lives we had to lead
whenever we weren’t in the condo and our real lives as two hot girls.

We proved we were hot girls in love sessions that were more spirited than
when Jeremy was pretending to be a boy. I thought that Jeremy was
passionate, but Krissi was insatiable.

I even <blush> fucked Krissi. Once or twice a day. My little clitty
couldn’t have felt like much to her, but she either really enjoyed it or
was faking extra nicely. I don’t think all those earth-shaking cums she had
when I was plowing her pasture could have been faked.

It was a lot of fun putting little Sarah into Krissi’s warm place. I lubed
her up each time and that alone had her gasping and panting. Often, she
came hard before I even entered her. I must have been sexier than I
thought.

Making love as girls was different, but still lots of fun. One Saturday, I
brought out two of my Aunt’s tiny nighties that had lacy openings where the
boobies were supposed to be. All we had were our puffy nipples, but
exposing them like that was very exciting. We reversed on each other in bed
and worshiped each other’s nipples until we came three times each and
almost fainted.

One day, I brought out two pairs of satin gloves and we rubbed each oher
all over with them. My gloves had three big cummy loads on them at the end
of the day and Krissi’s had four.

But Krissi and I had to admit at the end of a month, that we wanted to feel
boys on top of us, rubbing us with their hairy chests, putting their big
cocks in us all the way to our throats. Mmmmmm.

I suggested one Wednesday that we begin by venturing forth babishly that
coming Saturday. We would shop a little, get a make-up makeover/lesson and
visit our city’s art museum. The important thing was for us to get out and
visit the world as Sarah and Krissi. If we ran into any boys, that would be
a bonus.

Krissi eagerly agreed, but began to fret about what she would wear. The
next two days, our orgasms were slashed in half as we made clothing
selections. Krissi settled on a pretty white dress with blue polka dots,
white stockings and pretty blue, four-inch, stiletto sandals. She did look
scrumptious in it! I wore a lovely red dress with black stockings and red
stiletto sandals. We looked very hot!

When we emerged from the condo at noon on Saturday, blinking at the
sunlight, we beheld a world we hoped was ready for Sarah and Krissi.

We got into Krissi’s car and she realized she would have to drive in
heels. That took a bit of practice, but we survived.

Getting out of the car, we were struck by how vulnerable we were dressed as
we were. Men and boys, who could not always control themselves, would want
our bodies next to theirs. The wind was unpredictable and could blow up our
short skirts, exposing our pretty panties. And our garters and stocking
tops.

Where’s that old wind when you need it?

We went to our first beauty parlor for the make-up lesson. We wanted to get
our hair styled and fingers and toes manicured, but we would have been
discovered. Our longish hair was in a girlie style and our nails were filed
and clean.

The ladies at the beauty parlor didn’t seem to have any idea that we were
still (but not really) boys. They just gushed at how pretty we were and
made a few good make-up suggestions and adjustments. When they were
through, we had never looked better.

With that huge boost to our confidence, we went to a department store next
to the museum, picking up a few personal items and enjoying all the lusty
stares from the men and boys. My clitty was stirring as I saw some of them
giving me bedroom looks.

Still, my Daddy always said, “If you lie down with dogs, you get fleas.” I
took that to mean, if you want to meet nice boys, hang out at nice places.

Thus, we walked back to the car, put our packages in the trunk and strolled
over to the museum in our big heels. We were easily the femmiest people we
saw that day. The women and girls we saw were all in jeans or khakis. And
there we were flashing flesh. Our egos expanded with every lusty stare.

We paid our admissions and perused the paintings. Krissi and I loved art
and it was so enjoyable to be there. Being there as our true, girl selves
made it a perfect experience.

I couldn’t help but notice that two fine-looking young men seemed to be
taking a stronger interest in Krissi and me than the paintings. I nudged
Krissi and she nodded.

They were a little older than we were – seniors I would have guessed – and
very handsome, in a clean, nice way. I was such a bad girl. My little
pooper was tingling with the thought of entertaining one of those beautiful
creatures. They probably had big, hot, stiff cocks with thick blue veins
and long foreskins. And big heavy balls the size of peaches, filled with
hot cream. Ooooooh. My teeny clitty was leaking very badly, wetting my
little panties. I was so naughty. If one of them fucked me, would it hurt?
Would I be walking funny for a week? What beautiful thoughts.

The boys sort of drifted in the general direction we did. I was sure they
were sneaking little glances at us, but couldn’t catch them directly. The
dark-haired one disappeared for a few minutes, but came back soon after.

It didn’t appear that they would make the first move. And we weren’t trampy
enough to do so, although I did consider hanging a sign on my butt that
said, “Big cocks wanted. Inquire within.”

At around 4:30 we decided to give up and go back to the condo, consoling
ourselves with a few life-threatening orgasms and planning the next
venture. We went out to the car and when we arrived, disaster had stricken!
The left, rear tire was almost completely flat!

What would we do? We couldn’t change a tire in Aunt Beth’s pretty dresses
and all our other options were just as bad.

I was just about to cry, when I heard a deep voice say, “Can we help you
ladies?”

It was the boys from the museum! Oh frabjous day! Calloo, callay, as Lewis
Carrol said in Jabberwocky.

We shyly introduced ourselves and thanked them for any assistance they
could provide. Their names were Matt, the sandy-haired and oh-so-cute one,
and Greg, the dark-haired and only-a-9.9 one. They were both so tall — six
foot one — and so broad-shouldered, that we must have seemed like
munchkins to them. In our big heels, we barely came up to their chins.

They set to work and told us how they were seniors at LaSalle Academy, the
Catholic High School on the other side of town. They admitted to noticing
us and shyly asked for our phone numbers.

When they finished, we thanked them with big lipsticky kisses, with lots of
tongue. Matt was mine. Maybe we were just a tiny bit trampy. They responded
with some excellent rekissing. Mmmmm.

I said we could do better than phone numbers and told them about the
condo. Whether they wanted to come over or not depended on their reaction
to our “little secret.”

Krissi agreed beforehand that any boys we met and selected for
heart-stopping coitus would have to know the truth first. Sex with a
particular boy wasn’t worth getting beaten to a pulp for.

“We’re special girls,” Krissi said.

Greg smiled and said, “We already knew that.”

“No,” she persisted, “I mean we were born with boys’ bodies and we still
have our cocks and balls. Do you still want to make love to us?”

The boys considered us, realized we weren’t kidding, and looked at each
other. Silent agreement passed between them. Matt said, “We’re smart
guys. Why would we let a little thing keep us from making love to the two
prettiest girls in town?”

Oh, Matt. I hugged and kissed him, rubbing my tiny body against his
rock-hard cock. Krissi and Greg were in a deep clinch as well. They broke
it and got in Krissi’s car, Matt and I in his car.

As we drove, I wanted to remove that nice piece of meat from Matt’s pants
and give it a full inspection. Patience, Sarah, I told myself.

We got to the condo. The boys washed up the tire mess from their hands and
I fed the cats. Then Krissi and I went to the bathroom, fixing our faces
and plotting our next moves.

When we came out, the boys were sitting on the couch expectantly. I stood
in front of the door of the master bedroom. Krissi was in the door of the
guest room. On cue, we leaned over and slid our panties slowly down our
legs, all the way to our pretty heels. We stepped out of our panties one
leg at a time, then straightened up, holding our panties by one finger. We
looked at our boys, then at each other and dropped our panties to the
floor. Then we entered the bedrooms, leaving each door ajar.

Microseconds later, Matt appeared. He kissed me, smiling broadly. He was a
great kisser! I turned my back to him and asked him to unzip me. He did so
eagerly.

I removed my dress and hung it carefully. After shimmying off my slip, I
was standing there in a black cami, very sheer black stockings with
matching garter belt and big heels. My little girlfriend was painfully
erect and sticking up her entire three and a half inches. I sissied over to
the bed and lay on my back.

“Like what you see?” I asked.

Matt nodded, almost drooling.

“Can I see you now?”

Matt rapidly ditched his khakis, blue polo and teal jockeys. He stood
across from me with his rippling muscles and proud package. His body was
spectacular! All my dreams come true. His cock was almost exactly twice the
size of mine and very thick. It was leaking sticky goo, so I knew I was
exciting him. And his balls were fat and heavy with hot cream. Yummy!

I asked him, “Is that all for me?”

He smiled and said, “Every inch and drop, Sarah.”

Matt lay to my right on the bed. I felt his hot breath on my cheek as he
kissed me softly and explored my body with his right hand. He loved the
feel of my stockinged legs and the bare thighs above them. I knew he was
straight, but the boy seemed fascinated by my clitty. He said it just
looked so foreign there, like a guy at a bridal shower. He stroked it very
nicely as he trailed kisses down my shoulders and arms. He lifted my cami
and pulled it up over my nipples. I was clearly flat-chested, but Matt
licked and sucked my nipples as if they were the world’s tastiest ice cream
cone. It was so intense and erotic, I couldn’t hold back. I squealed once,
then gave a little eeky scream. Then I made a big cummy mess all over
Matt’s strong hand. The big doll smiled and told me how happy he was that I
liked him. I decided to show him how much.

His hand was all covered with cum. I offered him a towel, but he looked me
in the eyes and licked it off. Can I pick ‘em?

I asked Matt to sit on the side of the bed and I would make him really glad
he did. I got on my knees between his legs. His big boy was very ready for
some loving after a day of stimulation. I touched it for the first time. It
throbbed and spit a big sticky glob that almost covered the head. I
squealed with delight. He liked that.

I hefted his balls. Heavy! And loaded with something that was going to be
feeding me in the very near future. Matt liked the attention to his
balls. He got stiffer and his cock twitched. I ran my little hands all up
and down the veins that traversed his weapon. I decided to get moving here
or the first shot would be fired into the air and not into my hungry tummy.

I locked eyes with Matt, smiled sweetly and kissed his fiery cockhead. He
smiled back. At that moment, I knew this wasn’t just going to be a one-time
lay. We felt some thing between us. I was also pretty sure that he had sent
Greg out to let the air out of Krissi’s tire so we could meet. I was a
sweet little girl, but I wasn’t stupid.

I pulled Matt’s foreskin back, exposing one of the world’s most beautiful
sights, a pink, wet, excited cockhead, with pouting peelips and drooling
goo. I wet it some more with my mouth, replacing the goo with my
saliva. Just then, we heard a sexy scream in the next room. It sounded as
if Krissi was having her own fun. We giggled, then I went back to work. I
twirled my tongue in loopdeloops. I ran his cock all over my cheeks,
soaking them with his wet secretions. I kissed, frigged and skinned his
cock. I was very good. And in about five minutes, I got the girl’s big
reward. Matt grunted. His cock throbbed hard, twitched and erupted. I
wanted to swallow some and let Matt give me a pimple-preventer with the
rest. There was enough hot cum for a whole homeroom of girls. It felt so
good on my tongue, pallet, throat, cheeks and nose. I looked like someone
who had just come inside when it was raining cum. Matt was ecstatic. I
didn’t think any of his other
girlfriends had been half as friendly. Or skillful. Or giving.

He pulled me up for a big cummy kiss, which I loved so much. We ended up
toweling each other’s faces off and I went to fix my make-up and to be sure
I was all slick with vaginal jelly for what I hoped was the next round. I
put a lot of the stuff on, because I was worried about the size of that
monster in my little poopie-hole. It felt good applying that stuff. I
imagined how good Matt’s cock would feel.

More screaming and squealing next door. Hmmm.

I returned to the bed, kissed Matt and got on all fours, offering him my
best feature. He entered me with his fingers and worked me up to a slow
boil. By then, he was very hard again and ready for an anal lovefest.

Matt thought doggie-style was a little crude, I guess, because he put me on
my left side and spooned up behind me. I loved him taking charge. He
stroked my clitty and told me he would be gentle. My eyes filled a little
with fear, but lust was dominant. “I know you’ll be gentle, Matt. But
please, can I have your beautiful cock now?”

Not wishing to disappoint a lady, Matt paused at Heaven’s Gate. I felt the
wet tip of his cock against my tender anus. I quivered with fear and
desire. Then he pushed that whole, beautiful monster forward and entered me
with his big clubhead. Tiny pain. Big pleasure. Fair enough.

I was so full. He pushed more in. I was bursting. He pushed again. I was
being split in two! Give me more! He gave me everything. My world was
complete. My life had meaning. Fuck me!!!!!!

Matt did, and never forgot to kiss me or stroke my clitty. He was too big
for my tiny heinie, but my heinie got over it. I could feel his testicles
touching my bottom as he slapped his pelvis against my plump, wobbling
feminine buttocks.

There’s no orgasm like the one you have when your ass is stuffed and Matt’s
multiple assaults made me shake like California when the earth is angry. My
orgasm started in my ass and spread to my nipples, toes and clitty. My cum
seemed to be as blocked up as I was. It could only dribble out, but this
prolonged the feelings well beyond the usual best ten seconds of the day. I
spasmed for over a minute, which excited Matt so much, especially when I
was screaming as if I were giving birth, that he experienced what he later
told me was the best orgasm of his life.

He did say later though that the three he had later that evening were even
better. So were mine.

The boys reluctantly left us at ten under the condition that we would make
love with them every spare moment for the rest of our lives. That sounded
pretty good to me.

Krissi and I showered to remove the smell of raw sex, opening the windows
in a vain attempt to release the unmistakable odor of cum and carnal sweat.

As we emerged from the shower, Krissi realized that she hadn’t sucked my
cock all day, which, she said, was like a day without sunshine, so the
insatiable little sexpot got onto her pretty knees and drew moisture from
what I was sure was the desert. The boys were wonderful, but I would never
injure my relationship with Jeremy/Krissi for anyone. She still excited me
and the little teaser knew it.

Over the next two months, I came to the condo every day to become Sarah,
but apparently the other three members of our little club had actual
lives. Krissi was always there on Fridays and Saturdays, but at her
mother’s urging had joined some clubs that would go on college
applications. She kept her ball bag full on Mondays and Wednesdays, staring
at a chess club board instead of my clitty. That meant a vigorous ballbag
emptying on Tuesdays and Thursdays. Ouch!

The boys were attending to their princesses’ needs usually two or three
days a week, and not always together, so we had to discard jealousy and
love the one we were with.

On four occasions, Greg and I were alone in the condo. The first time, I
blushed like a virgin for him. I was nervous and so was he. Matt had given
him absolution to fuck me if I wanted him to. I wanted him to.

Krissi had told me that Greg was very oral, much more than Matt. He loved
sucking Krissi’s clitty and would often do so through two, even three
cums. He also knew how to massage a prostate as he was creating wet,
delicious friction on the glans.

I was eager to find out how much of this was fact and after some lovely
kissing, I lay back and let the young man work his mouth magic. Oh my
goodness, that was lovely what he was doing with his fingers back
there. Unnnnhhh. I didn’t know you could do that. What was he doing?
Ohhhhhh! I squealed “Gregggggg!” as he capped my clitty with his wet
mouth. He massaged my distressed prostate for 32 seconds longer as he
skillfully ran his tongue along the arrow-like underside of my sweet
meat. Then I dug my fingers into his hair, squealed like the biggest sissy
on earth and came. My eyes fluttered. My toes curled. My cockette twitched
and jerked as I spewed sperm and yelled bloody murder.

And Krissi said he did that two or three times in a row. He would kill me
if he tried that. Of course if I got near death, I could ask him to
stop. The bad boy’s fingers were still in my secret place. And moving. I
wanted to ask him to stop, but my prickie was hard again and I just
couldn’t form the words. Greg was licking my clitty all over with his long,
wet tongue. It was leaking sticky goo again, even though it had erupted
minutes before. Would I live through the afternoon? My asshole was sore and
tingling. My prostate was sending out cum alerts in rapid succession. Greg
concentrated his licking on the head, kissing and lubricating it with great
ardor. With his free hand, he stirred my little bag of grapes, squeezing
them gently. No one could resist that for long. I surrendered to his
attentions and my balls delivered another big, sticky load of love to
Greg’s eager lips. I shook and screamed, and still he massaged my prostate.

“Please,” I begged, gasping. “Fuck me, now.”

Greg smiled and mounted me. Covering me with kisses, then impaling me with
his burning rod into my impatient, eager ass. Aaaaaaaahhhhhh. My
nylon-encased legs and pretty feet with high, stiletto heels bounced on his
manly shoulders.

I was frenzied with lust and miraculously hard yet again. I dug my nails
into Greg’s ass, willing him to give me every millimeter of his cock. He
kissed my lips and told me how beautiful I was. I glowed with pride and
sexual heat. Oh, sweet goodness, I was going to cum once again, how was
that………… uuuuuuhhhhhhhh!!!!!!!

Greg was delighted that he had given me such pleasure and I could see that
his own ecstasy was approaching rapidly. The sweet torture slammed into him
and I grabbed him with all my 115 pounds, clutching him as he quivered and
flooded my tiny girlie pussy.

As we lay there after, my asshole drooling cum, I thought of myself as one
of the luckiest girls on earth.

It was even better on the days when the boys both showed up, but Krissi
didn’t. I was such a little cock hog. One Monday they each fucked me twice
in the ass as I sucked the other’s cock. Things were very good. Too good to
last as they were.

Chapter Nine – Changes

Two months before Aunt Beth and Uncle Hal were due to return, my mother
changed everything.

Mom’s best friend at work, Mrs. Dixon, was going back to work full
time. This meant that her 13-year-old son Danny would be a latchkey kid
after school unless Mrs. Dixon could find an alternative solution.

Mom, who apparently thought all I was doing at the condo was playing with
cats and watching TV, saw an elegant solution. Danny and I could keep each
other company at the condo every afternoon.

That, of course, was a disaster of humongous proportions, but I could think
of no suitable counter-argument except that it would leave me in boy’s
clothes with full balls. Greg, Matt and Krissi took it very hard. Krissi
cried. I felt awful. Maybe there was a solution.

I was not in the best mood when I drove to the Dixons’ on my first day to
“babysit” Danny. I was to pick him up at his house every day and drive him
to the condo. Surprise number one was when Danny stepped out of his house
carrying some cookies that his mother baked for us for that afternoon.

Danny was a living doll! Probably the most beautiful 13-year-old boy in the
world! And unless my eyes deceived me, he was sporting an enormous package
in those khaki pants.

Of course, sex with Danny would be robbing the cradle. But man, did I want
to get in that cradle and rock it with him. I wondered if all was not lost.

Danny was shy, but he wanted me to like him very much. He was so cute when
he offered me the cookies. He would have been cute doing anything.

When we got to the apartment, I left Danny in the kitchen to get some milk
and set off to do my cat duties. My head was full of possibilities with
Danny, even to the point of bringing him into our carnal circle. But if I
scared him……….and he told his mother……………who told my
mother………. I had too much on my mind as I bustled into the spare
bathroom to get the litter box and beheld – Danny. He was standing in front
of the toilet, with his very large cock in his hand. He was moaning with
lust as globs of sperm were flying from his big rammer. He had seen me
enter the room. But Danny was at the point in his orgasm where nothing
would stop him from cumming for any reason. We’ve all been there. His cock
was gorgeous! His body was gorgeous! But the most gorgeous things of all
were the tiny, blue, silky, bikini panties with white lace that were pulled
just below his buttcheeks. Danny was a panty boy!

What an interesting development!

My heart ached for him when he began to sob. He begged me, “Oh, please
don’t tell my mother, Mickey. Please don’t. I shouldn’t have done that. I
was just so………… I shouldn’t have done that.”

I knew the next few moments would be critical, but I didn’t have time to
strategize so I acted on instinct. He was sobbing, so I hugged him and told
him everything was going to be all right. At 5’8″, Danny was a giant next
to me, but he let me comfort him, since I was older and this was my
turf. Remember, his pants were still around his ankles and his recently
discharged weapon was still drooling gobs of cum. I ignored all that and
kept hugging him, rubbing his back.

I resisted a strong urge to fall on my knees and suck him to another
cockstand. Instead, I asked him to pull up his pants and come into the
living room. He did so, but was very ashamed.

I did the only thing I could to make him feel better. “Danny,” I said,
“There’s no need to be ashamed. Look.” And I pulled down my pants to show
him a white garter belt, holding up tan stockings and covered by cute,
little white panties.

Danny’s eyes got very big. The bulge in his pants began to grow again.

“I wear panties and stockings almost every day. Except when I have gym. Not
everyone understands. But you understand, don’t you, Honey?”

Danny sniffled and nodded his head.

I went on. “We wear panties because it makes us happy, right?”

Danny said, “Oh, yes. I adore wearing panties.”

“And other girlie things?” I asked.

Danny blushed. “I dream about it, but I haven’t yet.”

“I hope Krissi and I can help your dreams come true, Honey. Krissi is my
best friend, sometimes called Jeremy. My girl name is Sarah. Do you have a
girl name?”

Danny hesitated, then whispered, “Sydney.”

“That’s a pretty name for a pretty girl.”

Danny’s eyes flamed. “Do you think I could be pretty?”

“The boys will be lined around the block to ask you to go to the prom.”

This was so much for Danny’s young brain to process. His heart fluttered at
the thought of wearing a prom dress and being with a <blush> boy.

I asked, “Why were you masturbating in there, Sweetie?”

Danny decided to trust me. “I was so excited about being alone in an
apartment with a boy. I was imagining that you stripped me down to my
panties and kissed me all over.”

Wow! That sounded wonderful. But first, I wanted to give Danny what he
really needed.

“Come with me, Danny,” I said. I led him to the vanity table. I asked him
to strip to his panties. He blushed, did so and sat down. He was so
precious. I applied some basic makeup, then had him stand and slipped one
of Aunt Beth’s bigger nighties over his pretty head. I had found a whole
cache of Danny-sized stuff that must have been from a larger time in Aunt
Beth’s life. Then I asked Danny to face the mirror.

She was beautiful and truly Sydney for the first time in her life. Sydney
shook with emotion, cried, stared at herself, hugged me, stared at herself
and kissed me full on the lips. What a kiss!

I asked Sydney to look at herself for a while as I sissied myself up to
becoming Sarah. I stripped to my lingerie, then sat at the vanity to apply
my face. Sydney couldn’t wait. The little scamp had to thank me properly
for giving her the best day in her life so far. As I was primping, she got
on her knees in front of me and extracted my little peeny. To her credit,
she didn’t laugh. She said it was sweet and girlish, just like the rest of
me. Then she took the whole three and one half inches into her lipsticked
mouth and began to blow on it. I straightened her out about the misnomer of
a blowjob, then wiggled with delight as she girlishly sucked and licked my
little jewel to an earthquake-intensity cum.

The little doll almost choked as I gave her more juice than it appeared my
tiny balls could hold. At that moment, it occurred to me that my problems
were over. Sydney, if she was willing, could be the newest member of our
little sissy club and could even share our boyfriends. Strike that. Let her
get her own boyfriends.

I could see that not only her emotions were overloaded, but her clitty was
in DEFCON Four. I pulled her to her feet. Then I slipped on my four-inch
heels, so I could be somewhat even with her, and kissed her over to my
aunt’s and uncle’s bed.

I lay Sydney on her back and inched her panties over her large weapon. It
looked as big as Matt’s. I cuddled with her clitty. Then I reached into the
nightstand and extracted a small bottle of lubrication. Facing her and
straddling her hips, I lubed up both of our clitties, then began to rub my
oiled little teaser against Sydney’s big girl. I reached under her nightie
and played with her nipples as I rubbed cocks, telling her all the while
what a pretty girl she was. She adored every instant of it. Sydney was in a
proper lather when she finally came, whimpering and crying as six big ropes
leaped from her girlie stick. With my cock throbbing up against hers, I
felt each eruption travel its route. Seconds later, I joined her with five
hearty blasts of my own, mixing my goo with her ample girl juice on her
tummy and Aunt Beth’s pretty nightie.

We kissed for a sweet half hour, then I cleaned the oil off her clitty with
a warm wash cloth and showed her what a world-class blowjob feels like.

After that, I could have sent Sydney behind enemy lines and she would have
gone. Instead, all I did was suggest she meet my friend Krissi the
following afternoon for some lovely girlie fun.

Our sissy club was back in business. With a great new member.

Chapter Ten – Three Hot Girls

That night, I raised the abysmal spirits of my best friend Krissi by
recounting the afternoon’s delightful events.

“You have a charmed life, my friend,” she said.

It was about time, I thought.

The next afternoon, I picked Danny up at his house. This was the day Sydney
was going to be fucked and I think Danny sensed that. He was half scared,
half eager.

We arrived before Krissi, which gave Danny extra time to sissy into
Sydney. Already, she was improving her girlish mannerisms and glowing with
natural beauty. Krissi was going to love her. I left her in the spare
bedroom and closed the door, so it would be Krissi he met for the first
time, not Jeremy.

Jeremy was on time and eager. Fifteen minutes later I was Sarahed and she
was in full Krissi. I led Krissi to Sydney’s room and opened the
door. Sydney’s apprehension made her even more desirable. I wasn’t jealous
of Krissi’s drooling appreciation of the sight of Sydney, but maybe I
should have been.

They hit it off immediately.

We all hugged girlishly.

After a few minutes of small talk, I suggested that Krissi and I show
Sydney how we girls could have lots of fun. Sydney’s sweet eyes were wide
and her throat was dry, but she agreed. I showed Sydney how to lube a
girls’ tiny hole lovingly, running my fingers in and out of Krissi’s warm
place. It was obvious to Sydney that Krissi enjoyed it, especially since
Krissi’s cock had become perfectly outrageous. I kissed Krissi as I was
lubing her and she was very happy. Then I spooned behind Krissi and showed
Sydney how I entered Krissi with my little clitty. Krissi squirmed and
moaned appreciatively. Sydney was fascinated and horribly aroused. I
stroked in and out about ten times. Krissi squeaked and squealed.

I stopped. “Sydney, would you like to put your little girl in my tiny love
entrance while I’m stroking Krissi?”

Sydney nodded eagerly. The little doll longed to do so.

“Lube me up then,” I said. “Then enter me slowly.”

I stopped fucking Krissi for a while, but skinned her prickie lovingly as I
felt the novice, but eager fingers of our new girl in my tight spot. They
felt delicious there!

I groaned out, “That’s enough lube, Sweetheart. Now push it in one inch at
a time.”

Sydney scampered into position, aimed at the mark, pushed, missed, pushed,
missed, pushed and entered with about two inches and a large pop.

I groaned. Sydney was worried she had hurt me, but I told her that it was a
groan of pleasure. The girl had some cock! “Push on,” I said.

She did and when it all got in, I was stuffed and she was in a new kind of
heaven. She was so happy that she began to weep with joy. That was all very
nice, but I suggested she put her back into a little fucking. Sydney proved
quite adept at buttboring and the three of us grunted, squealed and finally
screamed out in a three-way paralyzing orgasm that left us all covered with
cum and presumed dead.

I had told Krissi the previous night that the first to get a stiffy after
the apocalyptic fuck we just experienced would get to drill Sydney
first. The thought of her sweet girlie butt resurrected me first and I
proposed that I show Sydney how it felt to be a wide receiver.

Seeing how much we all enjoyed it, Sydney couldn’t imagine it being
anything but fantastic. I did warn her that there may be some slight pain,
but since my yardarm was the size of a finger, she was probably safe.

I lubed her up and she wiggled as if she would explode before I even
entered her. Then she did explode, cumming in big jets and squeaking like a
little girl. Her pretty butt was apparently on a hair trigger. After she
came, her hole was nice and loose and I entered her tight, young, sweet
lovepit smoothly and lovingly. Sydney smiled over her shoulder at me like
the angel she was. Krissi saw my plump cheeks bobbing and took that as the
invitation it was. I stopped fucking Sydney just long enough to pick up a
four-and-a-half-inch passenger. Then the train chugged down the track to
Grand Cumming Station. Wooooo. Wooooo.

I reached for Sydney’s little girl, stroking its red head with a steady
friction. Sydney turned her head for a kiss. I entered her mouth with my
tongue. Our lipsticked mouths met. She spasmed and came into my hand,
clamping her butt on my clitty. I milked her until she was dry, then rubbed
the cum all over her balls. I felt the big one, increased my pace, then
BLEW cum globs into the prettiest little girl in town’s tender butt. Or
maybe Krissi blew goo into the prettiest little girl in town’s tender butt
when she unloaded into me.

Beauty is so subjective, but the facts were, I was not only having the best
time of my life – I was having the best time of anyone’s life.

Chapter Eleven – Things Get Even Better

Krissi and Sydney and I had so much fun that week, but Krissi and I didn’t
want to spook Sydney. So we didn’t ask any of the boys over until we asked
her first.

We had no need to worry. The thought of a boy’s cock in her butt had Sydney
leaping with joy. I called Matt and told him that he had to bring a date
for Sydney, because Krissi and I were jealous. He suggested his 13-year-old
brother Jimmy. I had seen Jimmy’s picture and he was a doll. Good choice.

When Saturday came, we three girls dolled up for fucking first, then we
were going to make the boys buy us dinner. A little out of sequence, but it
worked for us.

We had found a nice miniskirt, top and low heels for Sydney, but for the
fucking, she wore pink stockings and a pink nightie. This would be Jimmy’s
lucky day all right.

The boys arrived on time and Jimmy was as advertised. CUTE!!!! Sandy brown
hair, big blue eyes and tall for his age. I looked forward to making his
acquaintance at a later date.

Sydney batted her eyes shyly at Jimmy a few times and Jimmy was
smitten. Jimmy was a virgin, but ready to amend that condition at the
earliest opportunity.

We were all better at fucking than we were at small talk, so after around
fifteen minutes, the boys’ clothes had disappeared. Jimmy was even better
with his clothes off. I was such a cradle-robber.

Jimmy kissed Sydney sweetly and she purred. For some reason, we all stayed
in the living room, not minding our own business. We wanted to see the two
young lovers couple. Jimmy cupped Sydney’s bottom with his hands and stole
her breath with manly hugs and caresses. He was a natural. He also praised
her beauty, which delights any girl.

Sydney was hard and hot. We girls had greased each other’s bottoms before
the boys’ arrival, so only Sydney’s invitation was holding Jimmy back. She
gave it. He accepted.

Sydney sat on the couch and scooted down so that Jimmy could access her
pussy freely if he got to his knees. A good position. The four older kids
all stroked and caressed each other as we viewed the erotic drama.

Jimmy continued to kiss and adore Sydney verbally as he brought his excited
champion to her quivering hole. She was so small there and Jimmy was a good
six and a half inches. It was not lost on Jimmy that his new girlfriend’s
cock was bigger than his. He found it thrilling. Sydney was whimpering and
begging for his cock. Her pretty butt ring pouted for love. She reached out
and touched his cock and the worst thing happened. He lost his load before
he reached the depot! Jet after jet of Jimmy’s hot virginal cum doused
Sydney’s throbbing clitty and pink ball bag.

Matt, Greg and Krissi stared in horror at Jimmy’s embarrassment and
Sydney’s disappointment. It’s a good thing someone was thinking!

I stepped forward, rubbed Jimmy’s shoulders and told him there was plenty
more where that came from. Then I used my fingers to scoop Jimmy’s
still-hot boyish cream from sweet Sydney’s pubic area and used two fingers
to slather it with a piston motion on the inner walls of Jimmy’s lovely
butt. I told him what a good-looking man he was and how much Sydney wanted
him inside her. Sydney wiggled and squirmed provocatively and Jimmy’s cock
got the picture. It erected fiercely.

I kept fingering the lad’s lovely anus as he entered Sydney’s love pit. She
squealed with joy and reached around Jimmy to replace my fingers with her
own. Jimmy’s body covered Sydney’s and he mastered her the way she needed
to be mastered. Jimmy was a good one. I glimpsed about an inch of his shaft
as it pumped in and out of the little cutie. Their bodies slapped together
as the little angel cried and moaned.

Having relieved his anxiety with the hasty ejaculation, Jimmy settled in
for a long, slow, luscious fuck. Figuring Sydney was in good hands, Matt
and I and Krissi and Greg drifted off to the bedrooms for some wonderful
love. I was comforted by the sequential screams of requited lust I heard
from the living room all afternoon. Or maybe they were my screams. It’s
difficult to tell through the haze of carnal rapture.

Around seven p.m. we scrapped the idea of getting dressed to go
out. Instead we ordered pizza in. I’m sure the delivery boy could smell
what was going on in the condo, but he would only have been invited to join
in if it were a really bad porn video.

At nine, we had to ask the boys to leave. They were reluctant, but we gave
them a proper sendoff. We lined them up at the door, then got on our knees
and gave them each a full ball bath and took a big, gooey load in our
faces. Sydney, the bad girl, got two big facial loads from her Jimmy, then
kissed him a cummy good night.

When the boys departed, I had another stiffie. So did Krissi and Sydney, so
we got into a “sissy triangle” (a three-way 69) on the floor and drew out
the last drops from our exhausted testicles.

I was feeling very happy when I arrived home around 10:30 that
night. Generally, Mom and Dad were in bed by that time on a Saturday. I
wondered if they still “did it.” They were two good-looking people, both
small like me, though.

The lights were on so I stopped in the family room to say hi and good
night.

Mom said, “So, Sarah, did you and Krissi and Sydney and the three boys have
a good time?”

Fear gripped my body. I got a mega-dose of adrenalin as my “fight or
flight” options flashed through my mind. How did they know? What did they
know? Was my life over?

Dad said, “It’s OK, Sarah. We’ve known all along.”

Puzzlement. “You have?”

Mom said, “Of course. What kind of parents would let a sixteen-year-old
alone in an apartment more than 30 hours each week and not keep an eye on
things?”

I said, “I……”

Dad said, “Of course we approve. You and Jeremy, I mean Krissi are happy
for the first time in your lives. And Danny is too.”

A glow rushed over me. It was going to be all right.

“And Sarah,” Mom said, “Think about it. Weren’t there a startling number of
coincidences and circumstances that allowed all this to happen?”

What did she mean?

Mom continued. “Beth’s assignment was real, but your father and I worked
like dogs to make everything else happen. Think back. Your Aunt Beth was
not very girlie. Wasn’t it strange to you that she had all that incredible
lingerie and sexy clothes. And 63 pairs of killer panties?”

Embarrassed. “I guess.”

“Dad and I gathered all that stuff in the two weeks before Beth left and
seeded the apartment before you started going over there. We bought sizes
that we knew would fit both you and Krissi.”

“How did you know our names?”

“You really need to keep your voice down on the phone, Honey,” Mom
said. “Sydney’s mom had been telling me for some time that Danny was a
panty boy, so we got some clothes for her too and hid them in a separate
cache.”

I was in awe. “But the tgirl porn?” I asked.

Mom frowned at Dad. “Your father’s, I’m afraid. He’s always had a thing for
pretty girls with big cocks. He volunteered to donate his stash to help
make you happy.”

I smiled at Dad. He blushed a little, knowing that I had had to unstick
several of the pages.

“Did we meet Matt and Greg without your help?’

“Mostly, although Dad did help things along a little by letting the air out
of your tire that day.”

And I had blamed Matt and Greg. My Mom and Dad were guardian angels.

“Things worked out better than we could have hoped. We’ve been in on this
with Krissi’s and Sydney’s parents and we think you should all go full time
as girls. You can stay in your school if you like, or we’ll consider other
options, including home school. Oh, and Sarah?”

My head was aspin with wonder and joy. “Yes, Mom?”

“We’ve also been in contact with Matt’s and Greg’s parents. They’re eager
to meet you both. The boys are going to ask you to their senior prom in
three months. Let’s see if we can have pretty dresses and the titties to
fill them for you by then.”

I began to sob. I hugged Mom and Daddy.

Mom patted me and said, “There, there, Sweetheart. You deserve better than
what life has dealt you. We just want you to have a happy life.”

It certainly looked as if I would.