From alt.sex.stories.tg Sat May 11 01:17:39 1996

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From: LabRat@i-link.net (Karen Mitchell)

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Subject: Story - Iwillif.txt (14K)

Date: Sun, 05 May 1996 12:31:56 -0500

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I did not write this and you must be 18 or over to read it as it may

contain a great deal of adult explicit sexuality. If this is

offensive do not read - delete file. For those of us who enjoy ....

enjoy! Please do not ask for files by e-mail - I can barely keep up

with what I have now.

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.

-------