From alt.sex.stories.tg Thu Oct 24 16:47:22 1996

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~From: Ricky <rhunt29@mail.idt.com>

~Newsgroups: alt.sex.stories.tg

~Subject: TG: The First Time

~Date: Sun, 20 Oct 1996 21:55:02 -0700

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You know the drill, if you are under 18 you need to ask your mother if

you can read this because it has sex and other adult stuff in it.

-----------------------------------------------

The First Time by Ricky

I suppose it's rather trite to say your first time with a woman can

sets the pattern sets the pattern for your whole life. I know it was

true for me, but the pattern included more than sex, it changed my

whole attitude toward women and life. I was 18 and very green, having

grown up in a rather conservative family, and had only dated a few

times since entering college. Away from home and despite the normal

adolescent male longing to find out what was under those feminine

clothes I had never even come close to finding out. Then Mary came

into my life and it was never to be the same again.

We met in a small theater production at school, both of us aspiring

actors. She was an "Older Woman" of 20, and I was flattered and

excited to be with her in public. I was staying over spring break as

home was too far away to return for a week, and she lived in town. I

tried my best to be John Wayne or Clint Eastward flirting through

dinner and a movie, trying to impress her with my manly demeanor. To

my amazement she suggested we go back to her place at only a hint from

me. I was horny and amazed and readily agreed, and when I found out

her family was gone for the weekend and we were alone the fantasies

flamed in my head. Hindsight tells me she was gently but firmly

leading me to the bedroom with great finesse, but at the time I could

hardly believe how forceful and macho I was to seduce this vision. I

tried hard to be cool and experienced while undressing her, but the

infamous bra hook almost defeated me. We were soon in her bed where

she slowed my raging passions as she taught me how to pleasure her. I

fear I erupted in her hand when she first touched my rigid cock,

putting quite a dent in my image as macho seducer. But she joyfully

milked my juices and in time her loving touch and friendly

understanding were able to revive me to fill her hot cunt with my

manhood. It was comic and passionate and a wonderful way to learn

about sex.

Well, at least until we heard a car pull up in the driveway and a

cheerful whistle walk up the sidewalk. The stark terror of being

caught soon washed away the languid feelings after our mutual

pleasure. There was no way out of the small house, my car in the

drive clearly told her parents she had company and the back door was

opening before we could remove the bedclothes, let alone get dressed.

I have to hand it to Mary, she was cool under fire and quickly grabbed

two nightgowns from her dresser, put one on and handed me the other.

"You're a girlfriend from college that dropped in unexpectedly, just

get under the covers and fake it!" I quickly put on the nightgown,

stuffed it strategically with my shirt and pulled the covers over me.

My inability to raise a beard and long hair were unexpected assets,

but could we get away with this? We had barely hidden my clothes when

her mother knocked at the door to explain their plans had fallen

through and they would be home for the weekend after all. Mary coolly

introduced me as Jan and lied six ways from Sunday. Feigning

sleepiness I mumbled something in a high voice and we were soon alone

again.

Then the realization set in, I was going to have to spend the night

with Mary! She rolled over and gave me a hearty squeeze and we nearly

asphyxiated trying to smother our laughter. Soon I felt her hands

lifting the hem of my nightgown and caressing my crotch. I felt my no

longer virgin cock begin to rise in response to her delicate fingers,

but she surprised me by burrowing under the covers and placing her

mouth around my cock. I had heard about this, but never dreamed I

would get a blow job the first time I was with a woman. She really

knew her stuff, at first I felt just the tiniest sensation at the tip

of my pecker. She was flicking the tip of her tongue lightly over my

hole, and I felt my entire body contract. Then came an indescribable

feeling of warmth as her soft lips began to cover my rod, sucking and

nuzzling me. She slowly worked down my shaft and then back up and I

moaned with the feelings. She removed her mouth long enough to remind

me to be quiet and returned to work. She licked me up one side and

down the other, sucked first one ball and then the other, and finally

took both my aching balls in her mouth at once. I couldn't believe

how good it felt, the fire that was burning in my groin. I threw back

the covers so I could watch and was entranced by her blonde hair

sprang up and down as she slid along my aching cock. I realized I was

still wearing her nightgown but the slippery fabric seemed to caress

me as tenderly as her luscious lips. She played me like an enchanted

instrument, coaxing forth my cum as she licked my glans, then backing

off to nibble at the root of my cock until I gradually relaxed, then

hungrily engulfing my whole member with her greedy mouth and sucking

deeply. All too soon I felt my cum rising past the point of no return

and she happily swallowed my load as I strained to hold in the

triumphant cry I wanted to let out. Shaken, I lay there and once

again was aware of the nightgown I wore, and couldn't believe that I,

who had so recently been gloating over my macho way with women, could

enjoy being passive and receiving, not macho at all.

Kissing me, I could taste the salty flavor of my cum on her lips, and

she asked me to return the favor. Perhaps it was my newfound

appreciation of being receptive, I wanted to give her as much pleasure

as I could, but I didn't know how. I amazed myself by admitting to

her I had never had sex before and I didn't know what to do. She

laughed and hugged me, and gently pushed my head to her crotch. She

pulled up her own nightgown and spread her legs, brushing back her

golden bush to reveal moist, pink cunt lips that were dripping with

moisture. "Just start licking and listen to me, I'll tell you what

feels best."

So that's just what I did. Her fragrance was divine, musky and sweet,

and I gingerly outlined her exposed folds with my tongue. She sighed

in obvious pleasure and I got bolder, working my tongue into the slit

between her cunt lips, and sliding up and down. I soon learned what

she liked, and every time I neared her throbbing clit she made a soft,

low growl of happiness. Within minutes I had worked a finger up her

soaking vagina and was eagerly running my tongue over her cunt,

sucking her clit and wiggling my finger deep in her warmth. As she

began to move her hips I concentrated on her clitoris, as that seemed

to be the most sensitive spot, and soon she was bucking and strangling

her cries of pleasure so as not to be heard outside the room. At last

she gave a convulsive heave and I knew she was coming, I held on as

best I could and sucked for all I was worth as she gave in to wave

after wave of orgasm. We curled up together and slept the rest of the

night in each other's arms.

We woke late in the morning to the sounds of the rest of her family

moving about. In the light of day Mary's ruse began to fray a bit.

How was I going to get out of the house when her family thought I was

a girl? I didn't want to get her in trouble, not after last night,

but I couldn't live in her bedroom forever, could I? With a curious

grin she said there was only one way out - if I was a good enough

actor. She dug in her bureau and handed me a bra and panties, telling

me to put them on while she found something for me to wear. My

severely bruised macho reared up, but as I was standing there in her

nightgown at the time I was pleading a rather weak case even to

myself. So after a shower and a shave I donned her rather too small

underclothes (she had to help me with the bra hooks), stuffed the cups

with stockings and slid into the college uniform of jeans and baggy

sweatshirt. A little makeup and nail polish and the result was

amazing. I stared into the mirror and saw a casually dressed college

girl staring back.

How I managed to make it through breakfast that morning is beyond

recall, but I summoned all my acting skills and pulled it off. I

tried to keep conversation to a minimum, but her family kept asking

questions and I had to answer. Mary just grinned and winked at me,

enjoying my discomfort at this impromptu performance. I got a small

taste of her audacity and impulsiveness when she asked her folks if it

was all right for Jan to spend the break weak with them. I nearly

swallowed my tongue at that, but what could I do? I swear that

diabolical woman just grinned wider and loved every minute of it. As

soon as we finished eating she excused us to go shopping and I eagerly

escaped to my car.

She was serious, though, we did go shopping for clothes. For me. We

haunted the second hand stores and in a few hours she had assembled a

wardrobe to get me through the week. Bras, balloons to stuff it with,

panty hose, even a corset just for kicks. Dresses, slips, a nightgown

and such. I swear, by the time we were done I was starting to look

foreword to the week as a female, and not just for the challenge of

fooling her family. That night she had me model my new clothes, and I

was never more turned on in my life. The soft and slippery fabric

seemed to crackle with electricity as she touched me, smoothing,

pinning, and fitting to make the clothes fit my body. It wasn't long

before my erection made any kind of deception impossible, but she

simply dropped to her knees, took the pins out of her mouth and slid

my dick in. I was in heaven as I stood there in bra and slip while

she caressed my balls and sucked my dick. Once again I felt her lips

surround my manhood with a ring of fire, her cheeks sunken as she

sucked deep, coaxing my sperm to come out and flood her mouth. I

could just see her blonde curls bobbing past my bra, which was shaking

wildly as she sucked my cock, driving my hips back and forth with the

force of her suction. I could feel the cum riding in my balls and

pulled free of her embrace, grabbing at her jeans and pulling them

down. Pulling my slip out of the way I knelt behind her and drove my

dick into her sopping cunt, feeling her hot, young pussy surround my

aching member. With each thrust I penetrated her willing snatch as

deeply as I could, driving her foreword on her knees as she grunted in

animal passion. I could feel the weight in my bra snapping back and

forth with my thrusts, the feminine contrast to the masculine lust

driving me wild as I pounded into her. At last I came, blasting my

cum deep into her, filling her snatch with thick, white juice until it

began to drip on the floor beneath us. I was weak, hardly able to

stay upright as I held on to her ass cheeks for dear life. At last my

prick shrank and slipped from her pussy and we crawled to the bed,

pausing only to put on our nightgowns, and slept again in each other's

arms.

I will always remember that golden week together. She was a gentle

and loving teacher as she schooled me in feminine ways by day and

passionate sex by night. Within days I grew confident within her

family, to the point where we all went out to dinner together and her

father escorted me by the arm through the restaurant doors. I was

quickly able to do my own makeup, hiding my mercifully sparse facial

hair. We explored the town, two girls on a fling and going everywhere

together, even into the ladies room. In an amazingly short time I

felt I had been wearing a bra and panties all my life; they felt

right, somehow. They enhanced our lovemaking, there is nothing quite

like sliding stocking clad legs past each other, feeling the tug of a

garter belt as we fucked each other in as many ways as we could think

of. All the while her family accepted me as a girlfriend and were

none the wiser.

At last it was Sunday night, with school and normality looming in the

morning. I started to get undressed for bed but Mary stopped me. I

was wearing the corset and stockings as a kind of farewell to all

things feminine, but Mary wanted to enjoy the contrast of my clothing

and body one more time before it ended. Her hands began to rove up

and down my dress, caressing my body through the silky material. In

very little time her hands were sliding over the nylon of my panties

to trace the outline of my balls, and then sneaking under the elastic

and teasing my cock. I lay back, feeling the weight of my stuffed bra

against my chest, reveling as she stroked my cock and fingered my

balls. I could see my pecker standing proud and tall as I looked

through the cleavage of my bra, and was ready to bury it in her

snatch. But not quite yet. Sliding down on the bed I moved her over

and began to slowly unbutton her blouse. Sliding the strap of her bra

sensuously down her shoulder I exposed her tit and her deep brown

areola. I gently surrounded it with my lips, letting the warmth of my

mouth cover her breast, slowly moving my tongue in circles around her

nipple. I could sense her excitement growing and feel her nipple grow

and fill my mouth as I teased and flattered it with my tongue.

Reaching down I covered the warmth of her snatch with my left hand and

began to massage her clit through the covering of matted hair and

pantyhose. My hand slid carefully over her mound, teasing and

tormenting her with enough pressure to be tantalizing but not enough

to bring on an orgasm. I timed my sucking and rubbing so as my tongue

passed over her nipple I passed over her clit and pressed just a

little bit harder. I could feel her hips starting to move, her back

begin to lift from the bed as I worked her into a frenzy, Faster now,

and harder, I rubbed and sucked, reveling in the hot flesh of a

passionate woman moving beneath me. Still careful to control our

cries of passion with the family nearby I rhythmically sucked her

breast and rubbed her crotch until with a quiet grunt of ardor she

exploded in orgasm, driving her tit upward into my mouth and thrashing

her hips. Swinging her ass over the side of the bed I once again

lifted my skirt and slip, pulled down my panties and drove my cock

into her waiting muff. She forced her ass back at my engorged organ

and I thrust into her again and again, feeling the wonderful pressure

of my completely feminine outfit as I rammed my manhood into her.

Each thrust pushed her into the soft mattress and she sprung back to

cover my cock as I pulled back, our fucking creating waves of motion

in the bed. At last I drove deeper than ever as I felt a geyser of

sperm erupt from my pulsing pecker to wash the walls of her cunt with

sperm. I kept driving on and on as each pulse racked my body until my

cock was erect no more and I could no longer penetrate even her well

lubricated cunt.

In the morning I once again donned the ambiguous jeans and sweatshirt

to facilitate my return to masculine life once more. In my dorm room

I removed my bra and panties and felt somehow undressed without them.

That was 20 years ago now, and my wife Mary and I still laugh at our

audacious week together. Of course my in-laws know that Jan and I are

one and the same, and are very accepting however I am dressed when we

visit. Our sex lives are just as passionate as when we first

discovered each other and life is very good to us.