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I WILL IF YOU WILL
by Donna Sawyer
October 1990
Years later, on a rainy Saturday afternoon when I was 18 and
my cousin was just 16, and Mom and Dad were out, Tommy and I
found ourselves in the attic looking through old records and
photo albums and came across the old clothes we used to
"Dress-Up" in. I found my old favorite dress of Mommie's. It
was her pink prom-dress and I used to dream of filling it out
like she did in the photographs in her album. The couple times
she modeled it for us she was devastating! A real knock-out!
Now, Tommy teased me into proving to myself that I could now
fill it out. Of course, I did. In fact, I overfilled it. My
mother must have been a 36-C at the time and I was already a
36-D. We spent several minutes just reminiscing and wanting to
"Dress-Up" again, but we were both a little shy about it. Then I
found the cocktail dress that we used to dress Tommy in and held
it up to him. It was a beautiful royal blue satin dress with a
very full skirt and there were a lot of crinolines to wear with
it. He was still about my size and it really looked like the
dress would fit him.
I teased him back, saying I would if he would. Well one
thing led to another and I took off my blouse and jeans right in
front of him and slipped into the prom-dress. He got a hard-on
seeing me in my lace-cup bra and sheer nylon panties and then I
asked him to zip me up. He did and I couldn't wait to get him out
of his pants and see that hard-on more clearly.
"Come on!" I taunted, looking silly with my bra-straps
sticking out of my strapless gown and wearing bobbie-sox and
sneakers. Tommy laughed and said he would if I took off my bra
and put on the merry-widow he found that Mommie had to go with
her strapless dresses, and if I put on a pair of nylons and
heels. I knew he wanted to see more of my tits and legs and
pussy; and I was willing to show them to him if I could get a
look at his bare cock once again. I hadn't seen his tool in a
long time.
I told him I'd put on the corset and nylons if he put on
nylons and heels too and wore my bra and let us see how he
"filled-out" the high-neck cock-tail dress he used to wear.
He took my dare and took off his jeans and tee-shirt. His
cock poked firmly at the inside of his jockey shorts, but he took
the dress and stepped into it, covering his waist. Now I had to
give him my bra. I slowly unzipped my dress just to my waist and
let the bodice of the dress fall from my breasts while the skirt
stayed in place. I stuck out my tits as I reached behind my back
to get at my bra-hooks. I'll never forget showing my cousin my
bra-covered tits once again in anticipation of putting the very
same brassiere on him. It was a white Bali-bra with sheer lace
bra-cups and I loved how it let my nipples show through. I still
wear that style brassiere sometimes. It gives a firm, high jut
to my bust which is out of style now, but, to me, is still very
sexy and sophisticated. I snapped my bra-hooks loose and let the
weight of my breasts make my bust surge forward, an impressive
sight for a guy who doesn't get to see it everyday like I do.
Then I took one strap down after the other but still held the bra
in place with my arms. Ever so slowly I let the cups slip away
from my tits and watched him watch my nipples come into his full
view.
Tommy was holding the merry-widow I was to wear and now, with
my breasts bared to my cousin and both of us half wearing our
mother's old formal dresses, the bra he was to wear was dangling
from my forearms. I stepped toward him and as our full skirts
pressed together, I let the tips of my breasts brush against his
naked chest. He winced, almost as if in pain, at the sensation of
my hardened nipples on his chest. "You like the feel of breasts
on your chest, don't you dear?" I asked. He just murmured.
Then I backed away and held out my bra by the bra-straps for
him to slide into. He let me put the bra on him as he had years
ago and I reached behind him to hook the bra-hooks and again
pressed my tits into his chest, this time through the cups of my
own brassiere, which he was now wearing. With his bra in place,
I found my mother's old falsies in the chest and put them in
place in his bra-cups. They didn't fill out my D-cups enough so
I put another couple pair of foam-rubber falsies in his cups.
Now his bust was a full D-cup like mine.
Bare-breasted, I helped him finish putting the dress on. I
zipped him up the back and the dress fit perfectly. It fit his
waist and hips as though made for him even if the bust was a
little tight with my fully packed D-cup bra under it and his
fuller frame. The length was right too. He stepped out of his
sneakers and socks so he wouldn't look as silly as I did, then
looked at himself in the dusty old bureau mirror leaning against
the wall there in the attic.
He had become very serious and seemed to be having some sort
of experience. His lust seemed to be replaced with something else
and I wondered if I was making a mistake. He even seemed to lose
interest in my boobs temporarily. But whatever the experience
was, I could tell by the fact that his erection was now poking out
through his underpants and the heavy full skirt, that it was an
erotic experience. Mistake or not, I knew I lusted after that
cock. I knew I wanted his prick.
When he turned back to me I was afraid he'd want to stop
playing "Dress-Up" and get out of the dress. Here I was,
topless, my nipples as hard as diamonds, and I hadn't even seen,
let alone touched, his bare cock yet. I was beginning to feel
cheated when he came to me and held up the merry-widow I was to
wear. But more that handing it to me, he wanted to help me into
it. Somehow, I felt perfectly comfortable letting him. He
seemed to have changed into a girl.
As we stood there in the sunny attic, I let this "girl" in
the royal blue satin cocktail dress help me into the corset that
was a combination strapless-bra, waist-cincher, and garter-belt.
"She" handled my breasts carefully and lovingly; she didn't molest
me like a boy would have. She cupped them gently and helped me
with the long line of bra-hooks in back by leaning against my bust
and reaching around me. I laid my head on "her" shoulder and let
her take care of my brassiere. She unzipped me the rest of the
way and slid my dress down far enough to push my elastic garters
down inside my panties. (`This is a boy,' I had to remind
myself. `And he actually had his hands down inside my panties!)
"She" caressed my ass and my pussy, but only gently with light
finger-tip caresses. She finished with my bra and zipped up the
back of my dress. She led me to the mirror she had gazed at
herself in and I must admit, I looked fantastic in that dress. My
bust was absolutely stunning! My breasts jutted out in a high
horizontal rack of soft jiggling tit-flesh. My cleavage was deep
and long; not too tight, but curved and shadowy.
Then I led her by the hand to the trunk and found high-heels,
nylons, and petticoats for both of us. I also found a lacy
garter-belt and a pair of panties for my "sister". And I found I
found my mother's old black wig and put it on her. Between the
fact that the long dark hair was the same color as his and
complemented his complexion perfectly, and his naturally long
eyelashes veiling deep blue eyes, the transformation was
startling. Tommy really DID look like a girl. I showed him
himself in the mirror and he was as taken aback as I was.
"She" stood and raised her full skirt completely up and
waited for me to attend to dressing her in her underskirt
lingerie. The appearance of "her" cock snapped me back to
realization the he was indeed masculine, despite the dress. But
his masculinity was softened by the dress and I found that
immensely appealing.
First I knelt in front of him. His big erection inches from
my face. My heart was pounding as I lifted my hands to the
waist-band of his jockey-shorts in anticipation of pulling them
down and baring his cock. "Girl-cock", I thought. "Pussy-pole",
echoed in my mind. She was a girl with a cock! Oh! To be fucked
by such a girl! I wanted to make him feminine! Then I wanted him
to fuck me.
I pulled down the shorts and his boner sprung free and
bounced and bobbled in front of my face. It was quite hard, but
not rigid. I helped him step out of the shorts and in doing so
his cock grazed my hair. He let out a slight gasp at the
sensation, but he made no other reaction. I felt an electricity
flow from the unintentional contact with his prick, but also
restrained myself. I wanted desperately to touch it and feel it
and stroke it and suck it... I wanted to fuck that thick, young
man-shaft. But I didn't want to rape him. And the prospect of
seeing him fully dressed as a girl was thrilling enough to help
me hold back. I wanted this part of his manhood, but I wanted it
subdued into a feminine context. I could deal with him better as
a her. He didn't have to dominate me that way. In fact I could
maybe stay in control.
I did, however, sit back on my high-heels and admire the
sight of his throbbing member when he stepped out of his jockeys.
He knew I wanted it and was as curious about it as he was my tits,
ass and pussy, so he just held his skirt up and let me look at
him. Finally I felt he was awaiting some sort of judgement, so I
looked up at him and said, "It's gorgeous!" in a very serious
way. He smiled and seemed relieved.
I disciplined myself to be as serious as he was and reached
for the garter-belt to put on him. I again leaned toward his
crotch as I reached behind his waist under the skirt to fasten
the bra-hooks of the garter-belt. Again his cock caressed my
hair, but I made only fleeting acknowledgement of it, allowing my
cheek to touch it and my fingers to dance over it as I withdrew.
I tried to be as respectful of his sex as he was of mine when he
put my garters down through my panties. I realized that it would
be easier to do that if I thought of him as a her.
I chose to put "her" nylons and heels on next, leaving the
panties 'til last so I could enjoy "her" naked sex as long as
possible. He seemed to be a girl again now and despite the cock,
and my eagerness to play with it, my mental game was working.
To put her nylons on, I had her sit in an old rocking chair,
pull up her skirt, and let me kneel in front of her between her
spread legs. I gathered the seamed nylons in my hands one at a
time and let her put her foot in them, then caressed them up her
thighs and fastened the front garters. Fastening the garters was
a task that was greatly distracted by her immense tool bobbing in
my face, but my restraint prevailed. With both stockings on, I
asked her to stand and turn around so I could straighten her
seams and fasten her rear garters to her stocking tops. She
stood in front of the mirror and continued to hold her skirts up
around her waist, baring both her big girl-cock in front and her
cute round bottom in back. I knelt behind her and worked on the
sensuous feel of nylon-clad legs and looked past them at her
image in the mirror. I could see her balls dangling between her
legs from the rear and her cock bobbing in front of her in the
mirror. In straightening her seams I was sure to let the edge of
my hand caress those heavy oval nut-sacs as I adjusted her
stocking-tops and then fastened her garters.
I tightened her garter straps, stretching her stocking-tops
into taut inverted V's and adding a gleaming highlight to the
fine denier gossamer beige nylon. In adjusting her front
garters, I again grazed her girl-cock, as fleeting and respectful
as he had been in touching my pussy.
With her nylons in place and adjusted, I stood beside her and
let her watch as I raised my own skirt and adjusted mine. All
the while she continued to hold her skirt up.
Next I slipped her into a pair of 4" spike high-heels. I
chose white leather ones for her and she and I both thrilled at
her appearance.
Next I chose a crinoline and petticoat for her and helped her
into them. She helped me into the mine.
At last I had only her panties to help her on with. I had
chosen a pair of lace-adorned bikini panties like mine but I now
knew they wouldn't be big enough to contain her girl-cock so I
went back and got a pair of plain full-cut sheer nylon briefs
from Vanity Fair. She again raised her skirt and I helped her
step into them then glided the whispy nylon up over her legs and
finally encased that luscious cock in them. There was no choice
but to capture the thick jutting tool in a upward pointing
position. Her balls snuggled into the panty-crotch and the
underside of her rod pressed into the front panel of the sheer
panties. The nylon caressed it with lovely sensations and she
moaned with the pleasure of not only the feel, but also the sight
as she continued to hold up her skirt and we gazed at her legs,
thighs and pussy.
I could no longer resist and ran my palm up the nylon-encased
length of her hard shaft. She shuddered and sighed as pleasure
shot through her. And I was immediately addicted to the feel of
cock in nylon.
Completely dressed, I led her downstairs and made up her face
and brushed her hair. Eye make-up, an arch to her eyebrows,
foundation and pancake powder, blush and a carmine red lipstick
completed the job. Then I made up my own face in a similar
vintage 40s style. Frankly, we were beautiful, my panty-boy
cousin and I.
by Donna Sawyer
October 1990
Years later, on a rainy Saturday afternoon when I was 18 and
my cousin was just 16, and Mom and Dad were out, Tommy and I
found ourselves in the attic looking through old records and
photo albums and came across the old clothes we used to
"Dress-Up" in. I found my old favorite dress of Mommie's. It
was her pink prom-dress and I used to dream of filling it out
like she did in the photographs in her album. The couple times
she modeled it for us she was devastating! A real knock-out!
Now, Tommy teased me into proving to myself that I could now
fill it out. Of course, I did. In fact, I overfilled it. My
mother must have been a 36-C at the time and I was already a
36-D. We spent several minutes just reminiscing and wanting to
"Dress-Up" again, but we were both a little shy about it. Then I
found the cocktail dress that we used to dress Tommy in and held
it up to him. It was a beautiful royal blue satin dress with a
very full skirt and there were a lot of crinolines to wear with
it. He was still about my size and it really looked like the
dress would fit him.
I teased him back, saying I would if he would. Well one
thing led to another and I took off my blouse and jeans right in
front of him and slipped into the prom-dress. He got a hard-on
seeing me in my lace-cup bra and sheer nylon panties and then I
asked him to zip me up. He did and I couldn't wait to get him out
of his pants and see that hard-on more clearly.
"Come on!" I taunted, looking silly with my bra-straps
sticking out of my strapless gown and wearing bobbie-sox and
sneakers. Tommy laughed and said he would if I took off my bra
and put on the merry-widow he found that Mommie had to go with
her strapless dresses, and if I put on a pair of nylons and
heels. I knew he wanted to see more of my tits and legs and
pussy; and I was willing to show them to him if I could get a
look at his bare cock once again. I hadn't seen his tool in a
long time.
I told him I'd put on the corset and nylons if he put on
nylons and heels too and wore my bra and let us see how he
"filled-out" the high-neck cock-tail dress he used to wear.
He took my dare and took off his jeans and tee-shirt. His
cock poked firmly at the inside of his jockey shorts, but he took
the dress and stepped into it, covering his waist. Now I had to
give him my bra. I slowly unzipped my dress just to my waist and
let the bodice of the dress fall from my breasts while the skirt
stayed in place. I stuck out my tits as I reached behind my back
to get at my bra-hooks. I'll never forget showing my cousin my
bra-covered tits once again in anticipation of putting the very
same brassiere on him. It was a white Bali-bra with sheer lace
bra-cups and I loved how it let my nipples show through. I still
wear that style brassiere sometimes. It gives a firm, high jut
to my bust which is out of style now, but, to me, is still very
sexy and sophisticated. I snapped my bra-hooks loose and let the
weight of my breasts make my bust surge forward, an impressive
sight for a guy who doesn't get to see it everyday like I do.
Then I took one strap down after the other but still held the bra
in place with my arms. Ever so slowly I let the cups slip away
from my tits and watched him watch my nipples come into his full
view.
Tommy was holding the merry-widow I was to wear and now, with
my breasts bared to my cousin and both of us half wearing our
mother's old formal dresses, the bra he was to wear was dangling
from my forearms. I stepped toward him and as our full skirts
pressed together, I let the tips of my breasts brush against his
naked chest. He winced, almost as if in pain, at the sensation of
my hardened nipples on his chest. "You like the feel of breasts
on your chest, don't you dear?" I asked. He just murmured.
Then I backed away and held out my bra by the bra-straps for
him to slide into. He let me put the bra on him as he had years
ago and I reached behind him to hook the bra-hooks and again
pressed my tits into his chest, this time through the cups of my
own brassiere, which he was now wearing. With his bra in place,
I found my mother's old falsies in the chest and put them in
place in his bra-cups. They didn't fill out my D-cups enough so
I put another couple pair of foam-rubber falsies in his cups.
Now his bust was a full D-cup like mine.
Bare-breasted, I helped him finish putting the dress on. I
zipped him up the back and the dress fit perfectly. It fit his
waist and hips as though made for him even if the bust was a
little tight with my fully packed D-cup bra under it and his
fuller frame. The length was right too. He stepped out of his
sneakers and socks so he wouldn't look as silly as I did, then
looked at himself in the dusty old bureau mirror leaning against
the wall there in the attic.
He had become very serious and seemed to be having some sort
of experience. His lust seemed to be replaced with something else
and I wondered if I was making a mistake. He even seemed to lose
interest in my boobs temporarily. But whatever the experience
was, I could tell by the fact that his erection was now poking out
through his underpants and the heavy full skirt, that it was an
erotic experience. Mistake or not, I knew I lusted after that
cock. I knew I wanted his prick.
When he turned back to me I was afraid he'd want to stop
playing "Dress-Up" and get out of the dress. Here I was,
topless, my nipples as hard as diamonds, and I hadn't even seen,
let alone touched, his bare cock yet. I was beginning to feel
cheated when he came to me and held up the merry-widow I was to
wear. But more that handing it to me, he wanted to help me into
it. Somehow, I felt perfectly comfortable letting him. He
seemed to have changed into a girl.
As we stood there in the sunny attic, I let this "girl" in
the royal blue satin cocktail dress help me into the corset that
was a combination strapless-bra, waist-cincher, and garter-belt.
"She" handled my breasts carefully and lovingly; she didn't molest
me like a boy would have. She cupped them gently and helped me
with the long line of bra-hooks in back by leaning against my bust
and reaching around me. I laid my head on "her" shoulder and let
her take care of my brassiere. She unzipped me the rest of the
way and slid my dress down far enough to push my elastic garters
down inside my panties. (`This is a boy,' I had to remind
myself. `And he actually had his hands down inside my panties!)
"She" caressed my ass and my pussy, but only gently with light
finger-tip caresses. She finished with my bra and zipped up the
back of my dress. She led me to the mirror she had gazed at
herself in and I must admit, I looked fantastic in that dress. My
bust was absolutely stunning! My breasts jutted out in a high
horizontal rack of soft jiggling tit-flesh. My cleavage was deep
and long; not too tight, but curved and shadowy.
Then I led her by the hand to the trunk and found high-heels,
nylons, and petticoats for both of us. I also found a lacy
garter-belt and a pair of panties for my "sister". And I found I
found my mother's old black wig and put it on her. Between the
fact that the long dark hair was the same color as his and
complemented his complexion perfectly, and his naturally long
eyelashes veiling deep blue eyes, the transformation was
startling. Tommy really DID look like a girl. I showed him
himself in the mirror and he was as taken aback as I was.
"She" stood and raised her full skirt completely up and
waited for me to attend to dressing her in her underskirt
lingerie. The appearance of "her" cock snapped me back to
realization the he was indeed masculine, despite the dress. But
his masculinity was softened by the dress and I found that
immensely appealing.
First I knelt in front of him. His big erection inches from
my face. My heart was pounding as I lifted my hands to the
waist-band of his jockey-shorts in anticipation of pulling them
down and baring his cock. "Girl-cock", I thought. "Pussy-pole",
echoed in my mind. She was a girl with a cock! Oh! To be fucked
by such a girl! I wanted to make him feminine! Then I wanted him
to fuck me.
I pulled down the shorts and his boner sprung free and
bounced and bobbled in front of my face. It was quite hard, but
not rigid. I helped him step out of the shorts and in doing so
his cock grazed my hair. He let out a slight gasp at the
sensation, but he made no other reaction. I felt an electricity
flow from the unintentional contact with his prick, but also
restrained myself. I wanted desperately to touch it and feel it
and stroke it and suck it... I wanted to fuck that thick, young
man-shaft. But I didn't want to rape him. And the prospect of
seeing him fully dressed as a girl was thrilling enough to help
me hold back. I wanted this part of his manhood, but I wanted it
subdued into a feminine context. I could deal with him better as
a her. He didn't have to dominate me that way. In fact I could
maybe stay in control.
I did, however, sit back on my high-heels and admire the
sight of his throbbing member when he stepped out of his jockeys.
He knew I wanted it and was as curious about it as he was my tits,
ass and pussy, so he just held his skirt up and let me look at
him. Finally I felt he was awaiting some sort of judgement, so I
looked up at him and said, "It's gorgeous!" in a very serious
way. He smiled and seemed relieved.
I disciplined myself to be as serious as he was and reached
for the garter-belt to put on him. I again leaned toward his
crotch as I reached behind his waist under the skirt to fasten
the bra-hooks of the garter-belt. Again his cock caressed my
hair, but I made only fleeting acknowledgement of it, allowing my
cheek to touch it and my fingers to dance over it as I withdrew.
I tried to be as respectful of his sex as he was of mine when he
put my garters down through my panties. I realized that it would
be easier to do that if I thought of him as a her.
I chose to put "her" nylons and heels on next, leaving the
panties 'til last so I could enjoy "her" naked sex as long as
possible. He seemed to be a girl again now and despite the cock,
and my eagerness to play with it, my mental game was working.
To put her nylons on, I had her sit in an old rocking chair,
pull up her skirt, and let me kneel in front of her between her
spread legs. I gathered the seamed nylons in my hands one at a
time and let her put her foot in them, then caressed them up her
thighs and fastened the front garters. Fastening the garters was
a task that was greatly distracted by her immense tool bobbing in
my face, but my restraint prevailed. With both stockings on, I
asked her to stand and turn around so I could straighten her
seams and fasten her rear garters to her stocking tops. She
stood in front of the mirror and continued to hold her skirts up
around her waist, baring both her big girl-cock in front and her
cute round bottom in back. I knelt behind her and worked on the
sensuous feel of nylon-clad legs and looked past them at her
image in the mirror. I could see her balls dangling between her
legs from the rear and her cock bobbing in front of her in the
mirror. In straightening her seams I was sure to let the edge of
my hand caress those heavy oval nut-sacs as I adjusted her
stocking-tops and then fastened her garters.
I tightened her garter straps, stretching her stocking-tops
into taut inverted V's and adding a gleaming highlight to the
fine denier gossamer beige nylon. In adjusting her front
garters, I again grazed her girl-cock, as fleeting and respectful
as he had been in touching my pussy.
With her nylons in place and adjusted, I stood beside her and
let her watch as I raised my own skirt and adjusted mine. All
the while she continued to hold her skirt up.
Next I slipped her into a pair of 4" spike high-heels. I
chose white leather ones for her and she and I both thrilled at
her appearance.
Next I chose a crinoline and petticoat for her and helped her
into them. She helped me into the mine.
At last I had only her panties to help her on with. I had
chosen a pair of lace-adorned bikini panties like mine but I now
knew they wouldn't be big enough to contain her girl-cock so I
went back and got a pair of plain full-cut sheer nylon briefs
from Vanity Fair. She again raised her skirt and I helped her
step into them then glided the whispy nylon up over her legs and
finally encased that luscious cock in them. There was no choice
but to capture the thick jutting tool in a upward pointing
position. Her balls snuggled into the panty-crotch and the
underside of her rod pressed into the front panel of the sheer
panties. The nylon caressed it with lovely sensations and she
moaned with the pleasure of not only the feel, but also the sight
as she continued to hold up her skirt and we gazed at her legs,
thighs and pussy.
I could no longer resist and ran my palm up the nylon-encased
length of her hard shaft. She shuddered and sighed as pleasure
shot through her. And I was immediately addicted to the feel of
cock in nylon.
Completely dressed, I led her downstairs and made up her face
and brushed her hair. Eye make-up, an arch to her eyebrows,
foundation and pancake powder, blush and a carmine red lipstick
completed the job. Then I made up my own face in a similar
vintage 40s style. Frankly, we were beautiful, my panty-boy
cousin and I.
