Chubby Jamie driving me crazy
By: Date: 2023.03.19. Categories: Sex Stories Tags: , , ,

I was 20 years old and living in my first apartment for
almost a year. I had graduated from high school about 2
years prior and had immediately landed my first position
in the business department of a large lumber corporation.
There was a company branch site in my hometown, a large
metropolis in the South, so I began working from home
soon after graduation.

About a year later I moved into my little apartment, on
the other side of town from where I grew up. I was very
proud of that apartment. What a bachelor pad! Okay, so
the apartment itself was kinda small: it had one bedroom,
a den, a kitchen, a bedroom, and a closet, all of which
were more or less cramped for space. However, the rent
wasn’t so high, and there were a lot of extra benefits at
the apartment complex.

For example, we got a satellite TV hookup in the main
room, and Ethernet was free. In addition, a community
pool, exercise room, and bar were available at no entry
fee to occupants of the apartments. I liked to keep fit,
so the exercise room was a big plus too.

Also, I did enjoy the good drink every once in a while,
so I frequented the bar after work hoping to get someone
to hand me a glass. (I was underage at the time.) That
bar was where, about a year after I moved in, I met
sweet, red-haired Jamie.

Jamie had just left high school herself, although in
retrospect I don’t believe I asked her whether she had
actually graduated or not. She was living in the
apartment complex as well and was supporting herself by
working as a secretary for a travel agency a couple of
blocks away. She was surprisingly alert and seemed
intelligent for a girl of her age. I would say that she
had more common sense than I did; she seemed to be very
worldly and able to take care of her own needs.

Jamie was quite a specimen of youthful beauty at the ripe
age of 18. Red hair decorated her head in long straight
strands ending in large curls, perfectly crafted. Jamie
had very white, creamy skin with no impurities anywhere
to be found on face, body, or foot. Only a few post-
adolescent blemishes adorned her sexy figure here and
there, reminiscent of her years of blossoming. She had a
very thin waist and was very slender overall, weighing in
at about 105 pounds, I would have guessed.

Jamie loved to wear deep red lipstick to show off her
wide, sensuous smile, and it contrasted her pure white
face amazingly. She was not unfamiliar with short, tight
skirts (mostly black ones), which seemed to be made
exclusively for her full curves. Her legs were long and
curvy as well, and were always closely shaven. Jamie’s
breasts were of a smaller size than the average, but she
definitely was not flat.

Finally, her small, cute feet and hands were almost
always painted red as well, to accentuate and complete
her perfectly rouged appearance. I liked this girl
tremendously. We seemed to hit it off almost immediately.
Jamie and I liked to go walking around the town, stopping
for ice cream or to play a game at a bowling center or
laugh at the silly people walking by over a light lunch.

Unlike most teenagers, Jamie was very sure of herself and
every action she took: if she was ever hesitant about any
decision, it was not at all obvious to me at any time.
Her persistent smiles communicated her confidence, and
that made her all the more attractive to me. When we
started to fool around, I was having a lot of fun. Jamie
liked to move slowly, like most girls, but never left me
unsatisfied. Jamie wanted to do most of the work herself,
but she perpetuated my pleasure and enjoyed studying my
intense looks of ecstasy, which she created.

Thus, she loved giving slow handjobs, moving slowly
enough so that I hardly progressed at all toward my own
orgasm but quickly enough so that the pleasure never
ceased. Jamie also liked to be stimulated with the hand,
and although she enjoyed mine, most of the time she chose
to use her own hand. I gathered that this, too, was
because she liked to see me turned on the most, and she
knew that me watching her pleasure herself really got me

I was always sure to have several condoms on me whenever
I was going to meet Jamie, especially once we started
fucking regularly. I was not, of course, a virgin, but I
didn’t want to catch an STD, and I certainly didn’t want
a screaming kid at all, but certainly not at my age.

Anyway, I knew that Jamie was also on the pill. (She
popped one of those things daily right in front of me.)
It’s not that I was suspicious of Jamie. I knew she had
had sexual encounters in the past, but she looked and
acted very healthy and I trusted her when she told me
that she was clean. It’s not like I could just go up to
her and demand that she get tested for every STD out
there anyway: that would be awful of me.

However, it was the threat of becoming a father that
scared me the most. I just simply never cared for kids,
and the prospect of taking care of one for 20+ years
financially, emotionally, and energetically never
appealed to me at all. So, I opted to use the condoms
anyway, even though I knew Jamie was on the pill. Better
safe than sorry. Even so, sex with Jamie was always
wonderful. She would always bring me up, ever so slowly,
toward my release using her hand, and then, when I was
getting close, she would slip a condom on me and I’d ride
her until I came in her very hard.

It always happened that she came first; her other hand
knew exactly what she liked. It always got her very
excited when it rubbed all around her clit and labia
before I mounted her. Sometimes we would do it doggy-
style or with her legs out to the side, but we liked good
ol’ missionary the best because it made us feel closer
together. I got maximum penetration into her with that
position, and for some reason, it always seemed to make
Jamie smile even more than before when I came on top of

I had only known Jamie for about four months or so when I
received word that the local company where I worked was
downsizing. I had to move to a different site out of
state in order to keep my job. If I was willing to make
the move the lumber company would give me a raise in

I thought about it for a long time, but in the end I
decided to move away. I thought it was the best decision
as far as my career was concerned, and I felt my life
should move on away from my hometown for at least a
little while. It was certainly a difficult decision to
leave my hometown, where I grew up, but it was even
harder to leave Jamie, whose company I had come to really

When I told Jamie the news that I was leaving, she was
very distraught. “Why’re you leaving me?” she asked, her
eyes pleading with me.

“It’s not because I don’t want to be with you or that I
hate this town,” I explained somewhat fruitlessly. “I
have to follow where my career leads me, and right now,
if I don’t leave, it would be a stupid career move.”

“When are you going?” she inquired.

“In about month,” I replied. Although I expected her to
say more, she didn’t, but she seemed to swell up, and
then tears came. All the time, she looked right at me
with her gorgeous green eyes. Finally I grabbed her and
held her, thinking about what I might do about her.

But both Jamie and I knew she couldn’t come with me out
of the blue. Her family was far too proud to allow her to
drop her entire life, including her job and apartment
just to follow some guy who she’d practically just met.
Jamie wasn’t tied down by her family, but she respected
them too much to disappoint them.

I thought about marrying her, but I was very hesitant
about walking down the aisle with someone I’d met only
four months ago. It was just too early in our
relationship, and we were too young.

That night I took her to the movies to get our minds off
my move. After a few days of emotional instability
between us, things were seemingly almost back to normal
in our relationship. It was very odd: despite the fact
that we only had a short time left together, we were able
to laugh, play, and touch each other just as we had
before. Those days were wonderful, just like before the
news of my move. It was a wonder that we were able to
forget about it and just concentrate on each other in the
remaining moments, savoring the time we had left to

We even had sex a few times in that last month. (We were
thwarted much of the time because I was very busy at work
packing up and getting ready to leave, in addition to the
fact that we were both somewhat depressed.)

About five days before I was to leave, Jamie and I were
once again spending the evening together, this time
lounging by the pool. Jamie was a knockout in her
favorite string bikini, nothing but white flesh exposed
everywhere, dressed in red from her cute curls, nails,
and tempting lips. She was smiling at me all evening, and
it was driving me crazy.

When the sun went down, we got our things and went to my
apartment. As we walked to my front door Jamie rubbed up
against me and swung her hips in front of me so I could
get an excellent view of her round little bottom. I
grabbed her flat tummy from behind with both hands and
began exploring a little.

She enjoyed that and responded by stopping for a moment
and squeezing my hands. Then she turned her head and gave
me a beautiful, devilish grin. “Wow,” I thought. “I’m
very glad I put those two condoms in my wallet today
before I came home.”

We entered my apartment, and Jamie ran to the bathroom to
take a quick shower. I could tell that she was very
horny, and that was making me hotter and hotter by the
second as well. The two of us hadn’t had sex for about a
week, and I already had a lot of tension built up.

Jamie emerged from the bathroom wearing her bikini again.
(I guess she assumed she wouldn’t be wearing it for much
longer.) I kissed her on the lips, then I told her it was
my turn in the shower.

“Don’t take too long; please hurry!” Jamie exclaimed as I
entered the shower.

I was hard in the shower and was thinking about Jamie’s
body the whole time. I couldn’t wait to touch her and
make her feel wonderful. When I left the bathroom, I
couldn’t find her so I opted to put on some boxers and an
undershirt in lieu of walking around naked. Right when I
had concluded that she must have left for some reason.
Then I heard her calling me from my bedroom. I found her
already buried under the covers. “Funny, I was just in
here,” I noted to myself.

I noticed her bikini top hanging off of a nearby chair.
That was a signal to me that she was naked underneath the
covers except for possibly her tiny bikini bottoms. The
realization brought a big smile to my face and made my
cock jump with anticipation.

I climbed under the covers to join her. My hands roamed
all over her body, her tummy, legs, inner thighs, outer
thighs, and breasts. I stopped to attack her neck,
planting long kisses below and behind her ears. I then
rubbed my palm slowly across her shoulder blades, down
her arms, and then I grasped both her hands.

Jamie returned my caresses by roaming her hands under my
shirt. I kissed her breasts all over, finally sucking her
small erect nipples softly, then more vigorously, making
her close her eyes in pleasure.

She reached for my hard cock, and rubbed it slowly, “Get
these clothes off right now!” she suddenly demanded.

I removed my shirt while she pulled at my boxers, then
raised myself and the covers up so I could look at her.
She was amazing; her body was a perfect. I could see her
entire body from pretty red hair and lips all the way
down to cute little arched feet. Only the bikini bottoms
impaired the view of her little snatch.

As always, I couldn’t believe that I was about to fuck
this girl. It was clear that we were both so hot that we
didn’t need any more petting to get us going. We both
wanted release.

I quickly hopped out of bed and grabbed my pants. I
opened my wallet and searched for one of the condoms, but
to my surprise, I couldn’t find any! That was really
strange. I knew, I was absolutely sure, that I had put
some in my wallet just that day. Still, maybe my mind was
playing tricks on me; I had a lot on my mind lately.
“Jamie, I don’t seem to have any protection on me. I’m

Jamie didn’t seem to be the least surprised or
disappointed, and continued to smile at me. “Come here.
Come back here,” she insisted. I returned to bed, and
Jamie quickly placed my hands on her waist. She seized my
thumbs and put them under her bikini strings on each
side. Then she curled my fingers around over the top of
the same strings, and made a motion for me to pull her
bikini bottom down. I hesitated.

Jamie leaned up to me and whispered, “Pull them down.
Pull. Don’t you want to pull them down?”

I could tell that Jamie was extremely horny now.

“But I don’t have protection, Jamie. Shouldn’t we stop?”
I asked.

“We don’t have to go all the way, I just want to be naked
with you,” she replied.

After convincing myself that would be okay, I began to
slowly pull Jamie’s bikini bottom down. It was a long
journey to slide them down her sexy legs all the way to
her beautifully formed feet.

Now totally naked, Jamie reached down and pulled me back
up to her. She immediately began fondling my cock and
balls as she usually did. I systematically went into
contortions. Her light caresses were driving me insane.
Then she grabbed my cock between her thumb and fingers
and began stroking me as she liked to do.

I was in heaven, but I craved more like weary desert
traveler craves water. My orgasm was starting to build,
and I pulled Jamie’s hand away. “Jamie, I don’t know. Do
you have any protection with you?”

Jamie stared at me for a few moments, keeping her
intoxicating smile all the time. Then she then quickly
moved her head back and forth to say, “no”.

I was mad with desire, “Well, I guess that’s okay. You’re
on the pill, right?”

Jamie then looked into my eyes, and stared at me briefly
in silence. Then she responded once again by rapidly
shaking her head from side to side to indicate “no”

I was in shock. “I thought you were on the pill all this
time!” I said.

“Um, I quit using the pill about a week or so ago,” she

My mind snapped back to reality. Then in a flash I knew
what was going on. Jamie had planned this encounter. She
stopped taking her birth control about a week ago,
knowing that it would quit working by tonight and that
she would be unprotected. Further, she must have hidden
or destroyed the condoms that I had placed in my wallet
today. Now she was making me so incredibly horny that I
would want nothing more than to fuck her.

Jamie had already found my hard-on again and was stroking
me up and down. For a moment, I let her, lost in the
pleasure she was giving to me. But then I snatched her
hand away once more. “Jamie, we can’t. It’s not safe. You
could get pregnant,” I insisted.

“Oh John, I’m not worried about that. Let’s not worry
about that right now. Let’s just have some fun,” Jamie
responded. “Don’t you want me?”

I hesitated, but had to concede that I most definitely
did want her.

“Look at me, John. Look at my body,” she demanded. Jamie
moved the covers down over us to the bottom of the bed so
that we were both exposed. Then she began cupping her
breasts with one hand, tweaking her nipples and wincing
with pleasure. She slowly spread her legs, and with the
other hand, she rubbed her clit and hole like she always
loved to. “Look at me, John,” she repeated. “Do you like
my legs spread like this? Don’t you want to fuck me?”

Indeed I did. The only thing I wanted at that moment was
to stick my angry, pulsing cock into that hourglass
figure. But I knew that was suicide.

Jamie grabbed my member and began stroking it again. I
moaned out in pleasure, and she moaned back at me,
rubbing her body against me like a cat in heat. Then,
with her eyes locked with mine, she slowly drew my cock
closer and closer to her waiting hole. When my tip
touched her moistness, I knew this was the last chance to
retreat. I hesitated even while Jamie grabbed my behind
to draw me into her.

Defeated, I leaned downward to Jamie’s face and kissed
her deeply on her shapely lips while I entered her
quivering nest. We both groaned in rapture at the initial
sensation as I penetrated her. Jamie was so wet that I
slid most of the way into her, and only had to push
myself in a bit further to make the penetration complete.

I couldn’t help myself, almost at once I began to move
slowly in and out of her, and with each stab Jamie dug
her nails hard into my back. She cried out as if she were
in pain, but there was only pleasure. Intense pleasure!

I moved my hands all over her legs, upturned and in the
air, on both sides of my thrusting hips. And I began to
pump her a bit faster.

“Oh god, what am I doing? What am I doing?” my mind
screamed, but my body did not listen as I continued to
drive my rod deep into her like an animal.

I looked down at Jamie, at her perky breasts, her white
skin, her visible rib cage, her flat tummy, and her very
narrow waist. I knew that in a matter of moments I would
ruin that hot little body. Once I came in her, that same
tummy would grow out very large and her waist would
stretch and her figure would be damaged permanently. I
was going to impregnate this girl, and I was powerless to
stop it now.

If only I could quit just for a moment, long enough to
allow my reason to return so that I could stop. But I
knew I couldn’t. The pleasure was too intense, to primal.

“Oh god, god!! Please don’t stop, John. You feel so
GOOD!! Whatever you do, don’t stop. Please..” Jamie
pleaded with me in ecstasy.

Pound after pound I drilled deep into her, knowing that
with each thrust I was coming closer and closer to the
demise of my personal freedom as a man. Jamie was trying
to entrap me before I left town. If I got her pregnant,
then I’d have to be tied to her forever, she knew that.

Perhaps she would make me stay, or would insist that she
go with me. She was after my freedom; she wanted my baby.
As she drew closer and closer to her orgasm, she began to
admit that very fact. “Oh yes, YES! Oh John, it feels so
good. SO GOOD! I love you between my legs, on top of me.
You won’t get away from me, John. You can’t leave me. You
can’t. Doesn’t it feel good? Oh John!! JOHN!!! JOHN!!!
JOHN!!! YES!!” she exclaimed as her orgasm overtook her.

I felt her open up very widely and deeply. All of her
screams of pleasure and her desire for me to continue
pumping her was bringing me closer and closer to my own
climax. I started pounding her very hard. I couldn’t help

Then, I felt my orgasm very near. God, my body wanted to
cum in her, deep into her unprotected cunt. But no! I had
to stop somehow. If only I could hold back.. “AHH
AHHHH!!!!” I yelled as I began to cum deep inside Jamie’s
prefect body.

She sensed that I was cumming and she grabbed my
backside, trying to keep me from abandoning my task. She
needn’t have worried, though, because I was far too lost
in my orgasm, the pleasure of her body, and the sheer
bliss of the moment, for me to stop.

“Knock me up! Knock me up, John! You know you want to! Oh
please! Don’t stop cumming in me! Give me a baby!!” she
yelled. I came, squirt after squirt, in Jamie’s vagina,
my cock head coating her cervix over and over again with
my overjoyed sperm.

When I finally finished filling Jamie up with my seed, I
collapsed on top of her in utter defeat. She caressed my
back and ran her fingers though my hair. I looked up at
her, and she was smiling as always, perhaps even a bit
more now. “SShhhhhhhhh…” she said. “Don’t worry. It
will be all right. I promise. John, you should know that
it is close to the most fertile time in my cycle. But
don’t worry.. Please don’t worry.”

When Jamie told me about 3 days later that she was
pregnant, I had already decided that I would “do the
right thing” and propose to her. I postponed my plans to
move for about a month so that we could make arrangements
for a wedding and get married as soon as possible.

I married her about 3 weeks later, and then we moved out
of state to my new location with the lumber company.
About 8 months later out daughter Tammy was born. She was
quite a handful, always crying, shitting all over the
place, and needing to be fed.

Jamie gained a lot of weight during the pregnancy that
she never lost. Nearly 40 pounds. She just kept eating
and eating. She craved something, so she ate it. Ice
cream, doughnuts, cake, steak, you name it. The baby was
her excuse to binge. Her stretch marks made from the
birth of our baby are quite large and unattractive, and
her continued weight gain makes her look like she’s
perpetually pregnant.

It’s been 7 months since Tammy was born, and now Jamie
wants to have another baby. I don’t want another child,
and Jamie and I haven’t even had sex for at least 2
months anyway. I’ve decided to divorce her. I know I’ll
be paying alimony and child support for the better part
of my life, but I can’t stand to be around that fat woman
or the little baby that I never really wanted, even
though I have tried desperately to care for her. I’m
taking the papers to Jamie tomorrow.

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