Big slut from small town

I was your typical small town girl, pretty naļve, 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
c******n. 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-yes…” 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,
three…and 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 f****d 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!”