I was your typical small town girl, pretty naÔve, and with two options open to me
after high school: work a crummy job and live with my parents, or marry a local
boy and make lots of babies. Neither appealed to me, so at 19 I moved to the big
city for fun and adventure. After six months I had a cheap little studio
apartment and a job as a waitress in a run-down diner. It wasn't so bad; the food
was excellent, the tips were good, and we got one free meal a day. Connie, the
owner, mother-henned the four of us, watching out for me and the other young
girl, and cutting the two single mothers a lot of slack so their kids wouldn't be
neglected. Sometimes we'd go out together, but mostly my life consisted of split
shifts and TV dinners at home alone. Some adventure!

I met J at the diner. He was a regular who would always sit in my section, and
since he left $20 tips I was always happy to see him. J was a wealthy businessman
in his late 50's. He had the life: gorgeous home in an exclusive suburb, perfect
corporate wife, successful adult children. What I did not know was that he was on
the lookout for a mistress and had me in mind. He loved his wife and had no
intention of divorcing her, but he was bored and wanted a young plaything. From
the moment he saw me, he was determined to make me that plaything.

I was 5'10" with an hourglass 40-27-39 figure. I hated my huge DD chest that all
the boys ogled and was always trying to hide it. All through high school I'd
wished I were petite like the cute cheerleaders instead of a big lumpy basketball
jock. I slouched in a pathetic attempt to make myself small and flat-chested. But
through my slumping shoulders and ugly pink polyester uniform, J could see the
sensual possibilities of my voluptuous, statuesque, firm young body. I was shy
and insecure, perfect for the compliant girl he wanted. The more he saw me, the
more he wanted me.

After about a month of regular visits and those big tips, he asked me to dinner.
I was bowled over by him. He was older than my father, yet somehow it didn't
matter; I said yes. The restaurant he chose was nice, but not overly fancy, so I
was not too uncomfortable. J was a perfect gentleman and made me feel special.
When I confessed I felt fat, he told me that if this were the 50's rather than
the 80's I'd be the model of perfection, and that I was the most beautiful girl
he'd ever seen. When I lamented my inability to acquire the coveted golden tan,
he compared my white skin to rich cream and fine porcelain. At the end of the
evening he walked me to my door, asked if he could see me again, kissed my hand,
and left. After years of fighting off teenage gropers in remote parking areas, I
was enchanted!

It wasn't long before we slept together. I'd had wham-bam sex with two sweaty
boys; little had I realized it could actually be a pleasant experience. J was
attentive and gentle and adoring of my body. He took his time, caressing and
sucking my breasts. My embarrassingly large nipples enraptured him. No one had
ever licked my pussy, but he gave it probing attention before entering me and
fucking me long and slow. I did not cum-I never had-but I loved the new feelings
he stirred in me. I felt grateful and hopeful; within a few weeks he
propositioned me and I agreed to become his mistress.

I finally had what I'd always dreamed of! He set me up in a lovely apartment;
sent a housekeeper in twice a week; taught me how to dress sexily but with class;
sent me to a good beautician where I learned about makeup and had my light auburn
hair styled tastefully; enrolled me at a health club; sent me to a masseuse. He
said he never wanted to see my gorgeous breasts sag, so he had several good
support bras custom-made for me. I was required to wear these at all times,
except when we were at home together, when he insisted I be nude. When we were in
public I was forbidden to wear underwear. He wanted to be able to fondle me, and
occasionally he would discreetly expose me, delighting in people's reactions. I
never told him that I got secret pleasure form this-I could barely admit it to
myself!

Life with J soon settled into a comfortable routine. I quit waitressing of
course; my job now was to pamper and spoil him and make sure he was satisfied.
During the day I went to museums, took massage and art appreciation classes,
exercised at the club, shopped. We'd often meet for lunch at the diner and I'd
make sure he always dropped a twenty. Three or four nights a week he'd come over.
I'd usually fix a simple dinner; his favorites were mashed potatoes and tapioca
pudding, which he would spread on my breasts and lick off. Sometimes we'd just
sit and talk, him lying across my lap and suckling my long nipples, pretending
they had milk. Sometimes we soaked together in the spa, sipping champagne and
making love. Sometimes I'd draw a bubblebath and wash him and shampoo his hair;
then give him a massage; then sit astride him and lower myself onto his cock.
This was his favorite position because he could play with the titties he loved so
much. Sometimes I'd lie on the massage table and he'd content himself with my
pussy, licking it, fingering it, and inserting fruits, vegetables, and an 8"
dildo. I enjoyed this yet found it embarrassing. In general the sex was
satisfactory but not what either of us had hoped for. I was so inexperienced, and
considering my prudishness it's a wonder I ever agreed to be his mistress at all.
I continued to find sex pleasant but be non-orgasmic and squeamish. Once we tried
it anally, but I squealed in agony after slight penetration and was afraid to try
again. And I refused to fellate him; it was too disgusting to contemplate. He was
patient with me, but after three months he hinted that if things didn't change
soon our arrangement might end. That was the last thing I wanted! I was desperate
to please him but too scared to try.

J arranged for a doctor friend to give me birth control pills. My appointment was
at 5:30 p.m. After asking if I'd ever had a gynecological exam and learning this
was my first, the doctor called the nurse into the room and told her she could go
home. I remember how embarrassed I was when he had me disrobe while he sat there
watching, me trying unsuccessfully to retain some modesty. "Now dear," he said in
a fatherly tone, "don't be embarrassed in front of me. I've seen thousands of
women, you know. Put your arms down by your sides please and stand up straight."
I did so and he exclaimed, "My my! J said you were beautiful, but you really are
an outstanding physical specimen! I know you just want pills, but first I must
examine you for any diseases or physical abnormalities. Turn around please." He
ran his hands lightly over my back, then pressed along my spine from neck to
tailbone. He followed the contours of my buttocks, squeezing them firmly,
checking for lumps. "Bend over and touch your toes, dear," he said, and walked
around me, examining from every angle. He placed a low stool behind me and sat
down. I felt his breath on my thighs, then wanted to disappear as he placed his
thumbs on either side of my anus and tried to open it. It spasmed shut repeatedly
and he said, "Excellent muscle tone." Moving to my vagina, he spread and held it
open for some time before inserting a finger. My vaginal opening closed up,
trying to expel the intruder. "Very good, nice and tight. Now stand up and face
me." As I turned he stood up, placed his hands under my breasts, lifted them up,
and bounced them a few times. They didn't move much. "Nice and firm, very nice my
dear."

"J bought me some special support bras and makes me wear them all the time," I
explained.

"That's good. We fellows like our girls' breasts to be as firm and high as
possible! Alright dear, lie down on the table now." As I lay there he stood
gazing at my breasts. "See how your nipples point toward the sky? That shows how
delightfully ripe they are. Be sure to wear those bras so they stay that way. Now
I'll check them for cancerous lumps." He pressed around the base of each breast,
then over the entire breast from bottom to top. Placing my arms behind my head,
he repeated these motions. Then he held one breast in both hands and squeezed
firmly from base to tip. He repeated this a few times on each side. "Now I'll
check your nipples; they're especially susceptible to cancer." Working on both
sides simultaneously, he placed a fingertip on the nipples and pressed straight
down into the breast very hard. I winced from the pain, but he quickly released
and I felt my nipples spring up. Next he rolled them between his fingers along
the entire length. I could feel them growing and turned red; I hated that they
were nearly an inch long!

"Doctor, my nipples are so huge. Is there something wrong with them?" I asked,
obviously worried.

"Oh no dear!" he reassured me, stretching and releasing them several times. "I
stretch them to check their elasticity. Tell me dear, when I touch them this way
does it feel good?"

"Y-yesÖ" I said hesitantly.

"Does it make your vagina tingle?"

"Yes sir," I answered in a whisper.

"There, you see? Your nipples have normal responses to stimulation, and their
size is simply a delightful bonus for your lover. I bet J loves to suckle these
teats, doesn't he?" I nodded silently. "Too bad all girls don't have such long,
suckable nipples." Sighing, he moved to the foot of the table, grasped my hips,
and told me to scoot down to the end. Placing my knees in the special holders, he
slowly spread them as wide as they'd go. I lay there with my eyes closed, exposed
and mortified. No one but J had ever seen me down there. "I'm going to examine
you now," the doctor said. "Sexually active girls must be carefully checked for
diseases." He ran his ungloved fingers over my fluffy red bush and squeezed the
fleshy outer labia all over, then attached clamps to pull them back and expose
the inner area, explaining that he needed an unobstructed view. For some reason I
found the pressure of the clamps rather enjoyable. Gently grasping my inner
labia, he pulled them slowly in all directions, "testing their elasticity too,"
he said. Inserting two fingers into my vagina, he pressed up on the front of the
interior wall, explaining that this was my G-spot. The pressure felt good.
Suddenly he squeezed my clitoris with his other hand. "I'm testing your sexual
reflexes; can you feel that?" he asked.

"Y-yes!" I yelped as I nearly leapt off the table.

A third finger slipped in with difficulty. Releasing my clit but still pressing
inside, he reached up and pulled on a very erect nipple, then yanked it
repeatedly. "Is that pleasurable?" he asked as he switched to the other nipple.

"Yes sir," I whispered, red-faced.

After trying unsuccessfully to insert a fourth finger, he removed them all from
my vagina. He sniffed them and licked off my juices thoughtfully. "Excellent
vintage!" he declared, winking at me. I giggled. This surely was not what I'd
expected such an exam to be, but the doctor seemed pretty nice. He showed me a
long metal instrument. "This is a speculum," he said. "It stretches your vaginal
opening so I can examine you inside." He inserted it slowly into my vagina, then
opened it. My pussy stretched, not unpleasantly. "How is that?" he asked.

"Fine," I replied. He stretched it more, then still more, until I protested that
it hurt.

"Oh I'm sorry dear," he murmured, stopping for a minute. As the pain subsided, he
again stretched my pussy till I thought I'd rip apart.

"UUUNNHHH!!!" I screamed, and he quickly grabbed my nipples, squeezing them very
hard. Somehow that helped, and I gradually relaxed. After a minute he very slowly
closed and withdrew the speculum, my vagina clinging to it tightly. Again he
inserted his fingers-one, two, threeÖand the fourth was refused.

"Well dear," he chuckled, "your extreme tightness is wonderful for J, but makes
my job very difficult! I need a special lubricant to complete my exam. Excuse me
a moment." He left the room. I lay there a good ten minutes before he finally
came back. He removed a plastic cup from his pocket, poured out a white lotion,
and coated his hand thoroughly past the wrist. "This will lubricate my hand so I
don't hurt you as I examine your insides," he explained. This time the fourth
finger had no difficulty, but when he tried to add his thumb he again met
resistance. "Take a deep breath dear, then breathe out very hard." As I forced my
breath out the thumb slipped in and I felt a painful pressure. "Breathe again!"
he grunted, and as I did the pressure increased tremendously. My breath turned
into a scream and the pain was searing!. . .and slowly subsided. I realized his
entire hand was inside me! I marveled at how far my vagina could expand. Rotating
his arm very slowly, he poked and prodded all around; then he clasped my cervix
and squeezed it. "Can you feel that?"

"Yes doctor."

"How does it feel?"

"It feels nice," I answered truthfully.

"Good!" He curled his fingers into a fist and pressed rhythmically on my G-spot.
I was completely filled and the feeling was overwhelming. My clit was on fire.
With his other hand he rapidly squeezed and released my clit. "How's that
darling?" he asked in an odd tone. "Does that feel good?"

"Oh yes!" I exclaimed, feeling very strange. He continued this for a minute or
so; my heart was racing. Then he let go of my clit and raised my wide-spread
knees up toward my shoulders. He dipped a finger into the lotion. I felt a light
touch on my anus, then he slowly inserted it into my ass. Another shriek pierced
the room and I felt like I might faint. "I'm sorry dear, but I must check you for
colon cancer as well." I lay panting while he pressed his fist up and down and
slid his finger in and out for a full minute. Then, while slowly pulling his
finger from my ass, he carefully pulled his hand from my vagina. When he had
eased everything out completely, my ass and pussy felt suddenly, sadly, empty.
Giving my clit a last little pinch, he removed the clamps from my outer labia,
then gently massaged my mound for a moment. Standing by my side, he said with a
professional tone, "You have no diseases and excellent sexual reflexes, and your
breasts are very healthy. Abstain from sex for 24 hours to let your vagina heal.
J has found himself a lovely, healthy, sexy girl! One more thing," he said,
dipping his fingers into the remaining lotion. "This cream will keep your nipples
supple." He rubbed it in, then helped me stand. He bounced my breasts again
playfully. "I'm mighty Jealous of my old pal J!" he chuckled. "You may dress now,
my dear." As I dressed I was aware of him watching me. I was relieved to cover
myself, and my pussy and ass ached, yet I had an overwhelming desire to offer my
breasts to his mouth. I left reluctantly, confused over my conflicting feelings.

That night J placed me on the massage table, pushed my feet up to my crotch,
pressed my knees flat, and made me tell him every detail of his friend's
examination of me. While I talked he played with my breasts and stroked his cock.
When I got to the part about the doctor's fist being inside me, J moaned and
rubbed himself furiously, squirting his cum on my tits. He massaged it into my
nipples, saying it would keep them supple.

One night he announced we were going to a party. This was a first for us; usually
our infrequent outings were to secluded restaurants where other older men with
young companions eyed us knowingly. But this party was special; his friends would
be bringing their mistresses and girlfriends and he was anxious to show me off.
He had bought me a special outfit to wear: a leather micro-mini-skirt that hugged
my round ass, a thin silk sweater that clung to my protruding breasts like a
second skin, 4" spike heels, and elastic-top stockings which went all the way to
the tops of my very long legs. All were in a shade of rust slightly darker than
my hair but perfectly matched to my substantial bush; it set off my creamy skin
beautifully.  I was concerned about the shortness of the skirt, but I had to
admit I looked pretty hot!

We arrived at a beautiful mansion, curtains drawn and windows glowing warmly. A
valet helped me from J's low-slung sportscar, giving my legs an appreciative
look. I started to pull my skirt down to prevent him from glimpsing my auburn
fluff, but something stopped me and I got a secret thrill knowing he could see.
As I stood up I heard a low whistle. As we approached the front door J said,
"Before we go in. . ." and led me off to the side. On a hidden patio next to the
house, he raised my sweater over my head and behind my neck, then unzipped my
skirt, slid it down to my feet, and had me step out of it. The light from the
curtained door bathed my body in a soft glow. He turned me around and cupped my
breasts, caressing them, lightly pulling my nipples, coaxing them to their full
length. I chuckled to myself, realizing that besides just loving to touch me, he
wanted my nipples to be fully erect and pushing through the clingy fabric when we
arrived at the gathering. As he stroked me he told me how beautiful I was and I
closed my eyes, dreamily savoring my favorite sexual activity. I was lost in the
pleasure until I suddenly became aware of light and voices; I opened my eyes to
discover we were now inside the house! The floor had moved somehow! In a panic I
tried to squirm from J's grip, but he quickly tied my sweater tightly around my
upper arms, pinning them behind my back. I looked around and saw at least eight
men staring at my out-thrust breasts. The expressions on their faces. . .I
recognized the valet and the doctor. Behind them I could see a king-size
four-poster bed. Off to the side under bright lights was a gynecologist's exam
table with a segmented top that could be adjusted into many positions. The
stirrups had straps attached to them, and a low stool was nearby, on which was a
large tray containing many objects. I could make out two enormous dildoes and
much gleaming metal. Ropes hung from pulleys on the ceiling. I looked at the
table. I looked at the bed. I looked at the men-and realized I was the only girl
in the room! Pushing me toward them, J said, "Here she is boys! Enjoy!"