Frankie and His Gurl
Introduction:
1st-time affair of M2F crossdressing
by Julee Linn
[email protected]
When I was fifteen, I had a friend named Frankie who lived across the
street. Frankie was a couple months shy of his thirteenth brithday. He was a
little stocky and still sported some baby fat. He hard dark, curly hair. I
was taller and very slender, almost frail. I had dark blond hair, and it was
longish and fine. Every so often, Frankie would smile mischievously and say,
“You’re pretty.” I just smirked and took this as some preadolescent
silliness and let it ride. I had been called cute once or twice, but never
‘pretty’.
Naturally one of the subjects he had a growing curiosity about was sex. One
Tuesday evening, we were alone in his bedroom looking through some of his
dad’s porno magazines. They weren’t the typical Penthouse or Playboy
magazines, but cheaper more hard-core stuff showing explicit pictures of
naked women, leaving nothing to the imagination, mostly motorcycle sluts and
that sort of thing. My parents didn’t have that kind of magazine around, so
I managed to get off with catalogs that had lingerie sections showing women
modeling underwear. Being sexual with a female still seemed a far off
experience for me – I didn’t mingle a lot in school — so I fantasized about
what seemed more realistic: stealing a girl’s panties after she’d just worn
them and putting them on. But I didn’t have a sister and wasn’t bold enough
to do that to a neighbor, so that went on the back burner, too. I just
looked at the catalogs and masturbated.
After Frankie and I were halfway through the second crumpled magazine,
Frankie suddenly asked me if I jacked off. This wouldn’t have made me so
embarrassed if he had never told me I was ‘pretty’, but because I knew he
just might have some kind of an underlying attraction for me, this kind of
talk made me nervous. I guess I was afraid Frankie had some sort of
pre-adolescent sexual confusion that made him view me as a kind of girl
substitute. So I just nodded and said, “Yeah, I jack off,” and turned the
next page.
“Can you make white stuff?” he asked, his face almost in mine.
I nodded. “Yeah.” I gulped because of the direction the conversation was
going, and because privately a part of me wanted to go there, too. Only
three days before, I had been at my bedroom window and I saw Frankie sitting
on his front porch wearing nothing but short-shorts and sandals and found
myself staring at his smooth olive skin and the contour of his features. For
a fleeting moment, I wished I could see him totally naked.
“How do you do it so something comes out?” he said, whispering now. “Like
this?” He made a motion with his hand near his crotch as if masturbating.
“Well, something like that,” I replied.
“Can you show me?”
I grinned and blushed, shook my head. “I don’t know, Frankie. You have to
wait until you’re a little older. You can’t force it. Pretty soon it will
happen.”
We went back to looking at naked women. After a couple minutes, Frankie
asked me, “Could you show me how a guy and a girl do it?”
“Do what?”
“You know, have sex?”
“Well,” I said. “The guy lies down on the woman and sticks his penis inside
her. I told you that.”
“Then what?”
“They move together and he shoots inside her.”
Frankie’s excitement was growing. “Show me.”
“What do you mean show you? How can I show you?”
“Like if I was the girl, what would you do?”
He wanted me to demonstrate copulation. For some reason, even though I had
thought of Frankie in almost a sexual way last Saturday, there was nothing
arousing about what he was asking me to do. And in spite of those few
‘pretty’ remarks he’d made about me, I concluded that his curiosity about
sex tonight was that and nothing more. What’s more, we were both fully
clothed, wearing jeans, so I didn’t think much of it. It would be merely
clinical. So I had him lay down on his bed and I lay on top of him, rubbing
my pelvic area against his in small mechanical thrusting motions. I could
feel the small erection under his pants, and I felt a twinge of guilt having
liked it a little. I’m sure he liked it too. But we tried not to let on to
each other we did. We both stopped before it went too far, and I didn’t let
on that I was aroused. That was the end of it. He went out to ride his bike
and I went home.
Not long after that, on a rainy Saturday afternoon, we were looking at
magazines and he asked me to do it again. This time I had no illusions I was
teaching him anything new, I just wanted to do it for some reason. The
feeling was building up faster this time, and so was the guilt, so I stopped
after a few seconds, and Frankie seemed disappointed.
“Why’d you stop?” he said.
I just shrugged, hoping the red on my face didn’t show. Then Frankie sidled
up next to me and whispered nervously in my ear, “Wanna’ whack off
together?”
I hesitated, but thought why not, there would be no contact there, and I was
feeling horny. I said OK.
We unzipped our pants and took our penises out through our zippers. His was
short but wide, his glans pink, like a rosy mushroom. We stroked ourselves
watching each other while leaning back on the bed for a minute or two.
Suddenly, Frankie said, “Can I play with yours?”
His words came like a pleasant jolt. I was nervous, but horny, so I nodded.
He took mine in his hand. A rush went through me; I had never been touched
there by anyone else before. He pulled gently on it a few times, then gave
it little strokes outward. It instantly rose and became stiff.
“Touch mine,” he whispered eagerly.
His was little and not quite erect at first, but it rapidly swelled and
stiffened in my hand. The skin was downy and sleek.
We fondled each other for a moment and then began stroking each other. He
fisted mine while I stroked his with my thumb and three of my fingers. At
first I thought I wouldn’t be able to cum doing it in front of someone else.
But I was turned on by his soft hand and by seeing his own excitement grow
as he pumped himself and stared down at my penis in his hand. This time a
climax was just around the corner! Then of all things at all times, we were
startled by the voice of Frankie’s mother calling us down for dinner.
Huffing, we stopped and quickly pulled up our pants zipped them.
We were alone in my room once after that, but too timid to start anything as
long as anyone else was in the house. We both silently knew we had to be
home alone.
A week later, Frankie’s parents went out for their anniversary dinner and
dancing. Minutes after they left I came over to his house. We hadn’t planned
anything, so I wasn’t sure it was still on his mind. But after a half hour
of watching boring TV, he finally signaled his intentions by briefly
touching me between my legs and giving me a faint , red-faced smile. “C’mon
upstairs,” he said.
We raced up the stairs to his room. This time we lowered our pants down over
our knees, and I could see more of him than I ever did before. I didn’t
think I could ever be attracted to a boy’s privates, but I was. His pouch
was small and almost flat against the base of his lower abdomen. His member
was flaccid and swaddled in foreskin. Though wider than before, it still
seemed pristine and innocent looking.
We fondled and stroked each other. Frankie’s quickly stiffened and eagerly
shed its layer of foreskin. He moved closer and fluttered the velvety tip of
his chanterelle-like tumescence over and around my organs. Each light touch
sent a tingling sensation throughout my groin.
After a minute we got bolder and brought our genitals together, randomly
poking and teasing and exploring each other’s forbidden regions. It was new
and exciting. We were gasping. We pressed closer. Our sleek members glided
together, and our pelvises met. A fire started down there and soon spread
between my legs, and then burned up through my stomach.
As if we knew what we wanted, we both went to the edge of the bed and sat
beside each other. We pulled our pants down to our ankles. He opened his
smooth legs and guided me to lie forward onto him. My heart went wild as I
lay over him, and it felt so good as my genitals and loins reveled in his. I
moved very slowly and in short thrusts against him. At first, I tried to
keep my penis pressed on his, but it slipped off to one side. I finally had
to settle for letting it lodge in the crevice between his genitals and his
leg, The skin of his small erection was slick, and his little pouch so soft.
I stopped before reaching orgasm because I knew how I really wanted to be
when I did. I reclined on the bed’s edge. Frankie climbed on top of me and
put his dick on mine. In short but hard thrusts, he rubbed against me. I lay
still and held my breath. I was too shy to want to orgasm, but I was pinned
beneath him and held hostage to his warm flesh and great feeling knob. He
held me while I lay supine beneath him, and his embrace grew steadily
stronger, as did the feeling between my legs.
The urge grew in a flash and was so strong I that I came in three squirts
while he kept rubbing against me. When he stopped he asked me if he could
rub some of the white stuff on himself. I let him smear my silky white cum
on his sex organs. He started on me again with his quick thrusts. He kept
going faster, grunting as he struggled to climax. Finally, he seized up,
arching his back. His tummy fluttered. I found myself smiling that I had
helped him reach climax. It was the closest thing to an orgasm he would get
for now, being still too young to discharge semen.
I thought about that experience almost every day after that. But nothing
happened between us until about three weeks later, when were swimming in the
above ground pool at his house and his parents were not home from work yet.
We were alone in the pool and talking about girls and sex and what it would
be like again. We both acknowledged we had gotten stiff, but of course had
to check it out for ourselves. We started fondling each other and stealing
quick teasing embraces with our trunks down. His skin felt slippery against
me under the water.
That was enough to propel us up to his room and pull off our trunks in a big
hurry. It was the first time we were completely unclothed together, and the
first time we were alone in his house.
His slightly chubby abdomen curved down to his pubic area, which was white
in contrast to the tan on the rest of his body. The sides of his underbelly
tapered to a curvy V-shape at the bottom of which dangled his budding
privates. They glowed with a youthful sheen. There was fuzz around the firm
scrotum. His member, no longer stiff and not much more than a button from
the cold water of the pool, made him look chaste and all but gender neutral.
Looking into my eyes, Frankie finally stepped closer, and his member began
to rise. I just stood still, steeped in mounting anticipation. He did most
of the exploring at first, gently running his growing penis under mine, up
my hard shaft, to its head, then back down, rubbing the side of his against
the side of mine. During al this, I got stiff, my cock pointing to my chin.
I responded in kind, toying with his taut sack with my tip and frolicking in
its childlike sleekness. Then he gripped my buttocks and pressed his
erection into the more supple flesh between my testicles, and began making
short little thrusts. He drew me closer until our bodies came together, his
dick resting between my legs, just under my sack where it grew warm. His lap
skin was so fresh from the water.
We swiveled slowly against each other, our breaths deep and revealing. The
inside of my legs grew hot, made even hotter by the burning from his.
We stopped, and I fondled his erection. It was wider and longer than last
time. It seemed darker, too. It curved upward, and the tip pointed nearly
straight to the ceiling.
Then Frankie suddenly went to his closet. He pulled out something hidden in
the bottom corner. He came back carrying a girl’s bikini panty in one hand
and a bra in the other. The panty was rosy pink, and the bra was beige.
“They’re Karen’s,” he said. Karen was his cousin who was staying with his
family for the summer. “I found them in the hamper.”
“You going to wear those?” I said.
“They’re too tight for me. You’re more her size,”
He handed them to me and they felt like clouds in my hand. Frankie’s cousin
was sixteen and pretty, tall and slender, and these things had chafed
against her most intimate, private areas. Just the thought made my heart
race. I heard my voice crack so shrilly. “You sure it’s…okay?”
His breath quickened as he gaped at me. “Put ’em on,” he said impatiently.
Flushed, I put my arms through the straps of the soft, shiny bra and lined
it up over my nipples. It still smelled of Karen’s heavenly scent. While
struggling with the hooks in back, Frankie gently gyrated his hard penis
against my behind. His panting warmed my shoulder blades. He finally got the
woman’s garment snapped in place but kept stirring lightly against me.
The bra was a little loose, but it fit. It tender coolness sent shivers down
the sides of my body. Frankie handed me the panty again. It was dainty and
trimmed with lace and was so soft and delicate to the touch. So feminine.
“C’mon, hurry up,” he said.
He seemed as excited as I was. But I was feeling as shy as I was aroused by
the thought of wearing it. “I’ll wear just the bra this time,” I said,
handing it back to him.
Frankie was anxious. “Why?”
“I don’t know.”
“Please,” Frankie said.
I sat on the edge of his bed and, my face feeling flushed. I lifted my feet
and Frankie pulled the bikini on me. I became so stiff it almost ached. It
popped out from under the scanty crotch, but I covered it again. It was so
sensual against my skin I could barely quell a moan.
I sat slowly back down on the bed’s edge, my hands resting close to my
maiden hips. I wished I could make love to myself. I looked at my long,
slender legs and knew what I needed, but I was too shy to say at first. My
mouth went dry.
“Do you have any of…her stockings?”
Frankie was looking at me and playing with himself. “Sure,” he said.
He left and came back with a purple satin camisole that he put on me. He
also had a pair of Karen’s dark nylons that he gave to me. I was nervous
putting on the stockings at first; once again it was something taboo. The
second one was much easier as I rolled it from the toe on up to my thigh.
The nylons had elastic bands and stayed up by themselves.
I closed my eyes and indulged in it all. I was inspired in new exotic ways
by the sheer caress of the nylons and the loving touch of the panty and bra,
and the way the camisole wafted lovingly against my stomach and waist. I
stood and looked in his dresser mirror, posing from both front and side. I
was lanky and just wide enough in the hips, and with my long, lithe neck and
delicate facial traits I made quite a seductive girl. I was turned on both
by the feeling of the female attire and by what I saw in that mirror – a
pretty girl who I wanted to rush to and embrace. The intrigue was enhanced
by the fragrant scent of Karen’s bra and camisole. I saw my reflection
shiver with arousal.
Frankie stood in front of me, playing with his erection and breathing
heavily. “You look pretty,” he said and sat down next to me. He kissed me on
the cheek, close to my lips, and rolled onto the bed on his back. Still
feeling funny, I lay down beside him. Instead of hanging off the edge with
our feet dangling like before, we were both all the way on the bed this
time. His thigh brushed against mine, and he fondled me between my legs,
through the panty while still stroking his cock with his other hand. I
sighed with my arms on the pillow behind me. I was so eerie. I felt fragile
and passive, overtaken by my feminine side. I wanted to be a girl to
Frankie.
With eager breath, Frankie got on his knees in front of me and patted the
inside of my thigh, gesturing me to spread my legs. They fanned apart
eagerly. Then Frankie sprawled over me, propped up on his forearms, and
wiggled the tip of his hard organ against me through the panty while giving
me brief, impetuous kisses on and around my lips. I writhed beneath him, and
I sensed how much it stirred him even more. His breaths were quick and
uneven, and I could feel his knobby thing swell as he finally poked it under
the silky panty. He stopped long enough to pull one side of the panty off my
leg and left the other side draped around my thigh. I remained passive and
coy, with my eyes closed, my palms open up, and my arms at my side.
Suddenly, I heard him searching for something in the shelf behind the bed.
Then I felt something waxy and scented touch my lip. Frankie was putting
lipstick on me. I found myself more into all this and parted my lips to help
him. He also had a compact with rouge, which he used on my cheeks. When he
finished he put the mirror from the compact in front of me. I had tempting
cherry lips and sassy cheeks. With my less than long light brown hair, I
looked like an erotic, waif-like junior miss with a sort of a tomboy edge.
This boy-to-girl coupling agreed with us, although just minutes ago I had
been prudish about wearing the lingerie. We smiled at each other, having
found our true roles.
“You’re pretty,” he whispered.
I smiled and lay my head back down. I closed my eyes and wriggled
seductively. We both breathed heavier, and Frankie’s cheeks turned almost as
red as mine. He crawled atop me and lifted the hem of my slip, and, his
hands shaking with excitement. He began stroking my nipples through the bra.
After that he wet his index finger and made little circles between my legs.
Then he lowered his midsection down near mine.
He reached between us and arranged his hard penis so that it rested near my
own, in the crevice between my leg and scrotum. It felt like a burning
poker. Then he splayed his body over me, so that the warmth of our stomachs
and hips united. Frankie kissed me on the lips. The kiss was long and hard
and more skillful than before. He began stroking my breasts.
His lips still on mine, he began his thrusts, this time more brisk than ever
before. He writhed and twisted and gasped as I caressed his hips and
buttocks. Winded, he ended the long kiss and rested his cheek against mine.
As if steeped in female hormones, I whimpered meekly. His driving thrusts
became more vigorous. His high-pitched grunts grew louder, in time with the
rhythm of his sweaty cock. I could almost smell his pubescent hunger mingle
with the fragrance from Karen’s borrowed garments. I felt Frankie’s youthful
virility fuse with the bygone virgin deep inside of me.
That ‘girl’ inside me was burning her way to the surface. In my imagination
I fancied ‘her’ shaping and swelling the contour of my breasts to fill my
bra, smoothing the mound between my graceful legs, and puffing open the
orifice that would welcome Frankie’s young shank. I wished somehow he could
reach down between our moist bodies and ease his plump little organ inside
me.
Frankie’s humping got harder and faster. His body felt so good against mine.
Torrents of pleasure surged through and over me. I wrapped my legs around
him and brushed gently against his haunches with my stocking-clad ankles. I
dug my teeth into the back of my clenched hand but could not silence myself.
We both cried out, he with a horny boy’s groans and I with a shameless
girl’s moans. He reached under the back of my slip and clutched me and
pressed strenuously against me with all his might. His body bucked and
spasmed. Warm, silky fluid seeped gently between my legs. It was Frankie’s
first true ejaculation.
Frankie let out an intense orgasmic moan, as if wailing with both anger and
male pride. He lifted himself long enough to look at the little mess he had
made on me and cried, “I did it. I did it!” He moved his erection directly
on mine, proudly coating me with the semen still oozing from his young man’s
tool. I whined in soft tones and wriggled my hips beneath him while he gazed
at me with awe. Soon, an orgasm began welling up deep inside me, and sperm
surged up my shaft so fast I could almost hear it.
I finally exploded, and gobs of silky cream spurted forth, soaking his
snow-white organs and tawny belly. He kept heaving against me while he
silenced my girlish shrieks with a long, slow kiss. We kept going, until a
sticky froth built up between us and Frankie was out of breath.
We just lay there still and breathing hard until minutes later the need
arose in us again. I mounted him with my legs fanned apart and straddled his
wet loins. We both came again, this time at the same instant. It was
heavenly.
It wasn’t until a few weeks later, at his parents’ camp, that we it again.
We came back from the lake and Frankie’s parents had left with friends for
the day. Frankie had developed. His member was larger and more staminate.
The ripened sack under it was swollen and buff. The hairs around it were
thicker and darker.
He did my eyelids and makeup, guided by one of Karen’s teen magazines. He
had me put on a pair of clip-on hoop earrings he found, and dabbed my body
with perfumed talc. He brushed my hair down and had me put on a pink nightie
of Karen’s, a waist-length see-through peignoir with a matching thong.
I did things I never dreamed I’d do. I wrapped my lips around his penis
until it rose and got hard in my mouth. When he mounted me, I writhed gently
beneath him and stroked his back and neck with patient sensuality.
It’s now years later. I dress occasionally as a female, and I must say I’m
fairly sexy looking. Now and then when I get dressed to be with other males
and even females, I love it. But I still think of Frankie and my first time.
The End
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