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Lindsey - 1
by Tunefulbob (tunefulbob@yahoo.com)

***

This is a true story about my relationship with an 
extraordinary woman, whose real name might or might 
not be Lindsey. It's been my good fortune to have had 
several long-term relationships with women who were 
wonderfully sexy – but Lindsey is in a different 
league from them, a league where passion and intensity 
reach levels that were beyond my wildest fantasies. 
(MF, anal, fist, toys, rom)

***

Author Note: This is the first chapter of a true story 
of an intensely erotic love affair, with a wide 
variety of sexual activities.

***

Introduction

This is a true story about my relationship with an 
extraordinary woman, whose real name might or might 
not be Lindsey. It's been my good fortune to have had 
several long-term relationships with women who were 
wonderfully sexy – but Lindsey is in a different 
league from them, a league where passion and intensity 
reach levels that were beyond my wildest fantasies. 
Sooner or later, this story will include everything 
that has happened between Lindsey and me, right up to 
the present, from the quiet beginnings of our 
relationship to the current stage of our passionate 
lovemaking, including anal sex, fisting, insertion of 
a large vibrator into her pussy while my cock is in 
her ass, and penetration of her pussy by both my cock 
and the vibrator at the same time. But this story will 
not be told in the fashion that Aristotle described as 
ab ovo (from the egg). It won't start at the beginning 
and proceed in linear fashion. Instead, it will follow 
the sequence of my memory.

To give you an early taste of what Lindsey is like, 
here is an email she sent me recently:

My dearest Bob,
 
I'm finding it very, very hard to concentrate today. 
It seems as if all I can think about is having your 
cock deep, deep inside me. Thrusting in and out or 
sliding so smoothly that I want to cry out. Or lying 
next to you with your cock hard and pressing up 
against me while your fingers play with my pussy 
getting it all warm and wet. It feels so good when you 
touch me so gently. Softly playing with my clit and 
then putting your finger just inside and sliding it in 
circles. It makes me wet and so very horny just 
thinking about it. 

I loved having your cock so hard and swollen in my 
mouth yesterday and the feel of you coming and coming 
into my mouth, you tasted so good. I think I just came 
a little thinking about it.
 
I would love to be straddling you right now, 
pantiless. Right now I am so wet just thinking about 
you. Opening your pants and freeing your cock so that 
I could look at it and touch it and then slowly, so 
slowly slide on to it and have you fill me up so 
completely that I have an orgasm almost immediately 
trying very hard not to get any of my juicy wetness on 
your pants.
 
I want you to put my nipples in your mouth and have 
you suck on them and bite them just hard enough but 
not too hard, causing such ache and desire all the way 
down through my stomach and into my pussy. 
 
I want you to kiss my pussy and play with it with your 
tongue and gently suck and kiss my clit. And then I 
want to taste myself in your mouth as you kiss me deep 
and hard.
 
I want you kissing my neck as I wrap myself around 
you. I want your face between my breasts while your 
cock is deep inside me and I will move slowly up and 
down while my clit slides against your belly and then 
move a bit faster and harder until both our bodies are 
quivering with the excitement of exploding with each 
other. I love the feel of when your cock releases into 
me, emptying your balls, I can feel it pulsate and it 
excites me so much that I come at the same time, 
squeezing your cock with my pussy. I'm about to start 
playing with myself right now so I better stop.
 
I can't wait until we're together again. To think that 
we will have to wait all the way until Monday. It 
hardly seems possible. I wish I could steal you today 
after work but I have to go home because I have to 
pick Jake up from dropping off his car and I have a 
meeting after work tomorrow or I would beg you to meet 
me and then to fuck me. Your schedule is probably busy 
as well. I'm looking forward to Monday.
 
I'm sorry. I said I was going to stop and this wasn't 
very ladylike to begin with but to be honest with you, 
every time I look at you I am filled with overwhelming 
love and desire and just the thought of you causes 
uncontrollable and delightful, intoxicating thoughts.
 
L

Chapter One

My mind is filled with the memory of the first time I 
was able to push my entire hand into the inner cavity 
of her vagina. My glove size is large, to accommodate 
the breadth of my hand across the knuckles, though my 
fingers are rather slender. For some time, our love 
play had included the insertion of all four fingers 
plus my thumb into Lindsey's pussy; but the ring of 
bone around the top of her outer chamber had stopped 
me from pushing my whole hand into her inner sanctum. 
But on this day, with the help of KY, my hand suddenly 
pushed past that ring of bone so that it was buried in 
her to a point past my wrist. She yelped, and the 
pulsing of her pussy and quivering of her legs told me 
that the orgasm she was experiencing was especially 
strong. 

I curled my fingers into a fist, then rotated my fist 
inside of her and felt both the pulsing and the 
quivering increase in speed and strength. My knuckles 
were pushing against her cervix, which made her moan 
loudly and seemed to give her great pleasure. Somehow, 
I could feel her mixture of pleasure and pain, and 
experience with her the sensation of the endorphins 
flooding her brain. 

Her reactions, and my sensations of how it felt for 
her, transfixed me, excited me, enthralled me. After a 
few moments, the pulsing and the quivering stopped and 
she pushed her hand against my shoulder, which I took 
as a signal to pull most of my hand out of her pussy – 
she grabbed my arm before I pulled it all the way out. 
So I rotated my fingers and thumb within her outer 
chamber, sliding them in and out a little, catching 
her clit and dragging it into the opening – and she 
started to come hard again. And then she raised her 
hips off of the bed, grabbed my forearm and pulled my 
hand into her, urging me to stretch her inner chamber 
again. 

I was happy to oblige, and again pushed my whole hand 
into her, again causing her to yelp in mixed pleasure 
and pain, again curled my fingers into a fist, again 
rotated my fist within her, all the while pushing it 
against her cervix. And again her pussy pulsed, her 
legs quivered and she moaned loudly with the intensity 
of her orgasm. We repeated this sequence four or five 
times, then I pulled my hand out of her, thrust my 
cock into her hard and was astonished to hear her yelp 
with the same cry of pleasure and then to feel her 
squeezing my cock with her pussy as she came, though 
my cock is markedly smaller than my fist. 

I had expected that her pussy would be stretched out 
so that, at least temporarily, I wouldn't feel the 
tightness around my cock that creates such delightful 
sensations for me. My cock spasmed with a limited 
orgasm, without ejaculation. Lindsey felt my cock 
pulsing within her and started another long and hard 
orgasm, with her pussy pulsing in what seemed to be 
the same rhythm as my cock.

Let me take a moment to describe my darling, my 
beloved Lindsey. She is of medium height, with light 
brown hair, cut to medium length, and blue eyes. She 
has an athletic build, lithe, graceful and strong, 
with large breasts and slim hips. Her face is lovely, 
with intelligence and good humor gleaming from her 
eyes. 

She is old enough to have two daughters in their late 
teens, yet she looks no older than her early thirties. 
When I tell her she is beautiful, she laughs it off 
and tells me I am biased. Yet I remember the first 
time I saw her, walking in the middle of a small group 
of women. Lindsey immediately caught my eyes, looking 
sexy and lovely, someone special. The situation 
reminded me of the song – "I took one look at you, 
that's all I had to do; then all at once my heart 
stood still."

It was months after that before I had a conversation 
with her – and was able to confirm that her 
intelligence and charm were as striking as her beauty. 
Talking with her was instantly easy, as if we'd known 
each other for a very long time. I had been sort of 
provisionally in love with her since the moment I saw 
her; my real and abiding love for her dates from that 
first conversation. 

We occasionally had lunch together. And then we 
started meeting for glasses of wine after work. It 
wasn't long before we began capping off our glasses of 
wine with more intimate conversations and sessions of 
intense making out in one of our cars. My desire for 
her was practically uncontrollable. It took all my 
self-control to keep myself from pushing her hard to 
embark on a sexual relationship. Both of us were in 
marriages that lacked passion and romance; but it was 
hard for her to go against every rule about marriage 
and relationships that she had ever held.

One evening, in her car, our making out got especially 
intense. She had allowed me to unclasp her bra and to 
caress, kiss and lightly nibble on her lovely, dense 
breasts. While my mouth was occupied with her breasts, 
I moved my hand to her tummy and caressed her there, 
then gradually to the tops, then the insides of her 
thighs, about halfway up from her knees.

She was wearing pants with a belt. When I began to 
unbuckle her belt, she put her hand on mine to stop 
me, but then relented, and placed her hand on my neck, 
holding my mouth to her breast. I loosened her belt, 
undid the clasp at her waist and pulled the zipper 
down. I eased my hand under the elastic of her panties 
and found the spot where her external pussy lips 
covered her clit.

Without inserting my fingers, I began caressing her 
clit through the layers of her skin, squeezing her 
pussy lips together between two fingers. My reward was 
a gasp of pleasure that came unbidden from her. Only 
then did I slide one finger, then two, between her 
external labia, savoring the feel of the creamy 
slickness within. I slid my fingers up and down, 
lightly caressing her inner labia and her hooded clit. 
She began to moan and to breathe heavily – it was 
clear that she was close to coming.

Suddenly, she began pulling at my belt, undoing it, 
then opening my fly and pulling out my fully erect 
cock.  She slid down so that her pussy was beyond my 
reach, and then engulfed my cock with her sweet mouth, 
while grasping the base of it with one hand. She began 
pumping up and down with her mouth and her hand. It 
wasn't long before I exploded in her mouth, pumping 
spurt after spurt into her, perhaps a dozen or more. 
She swallowed it all and held her mouth on my cock 
until it stopped pumping and began to soften.

We kissed, open-mouthed. I couldn't taste any of my 
semen because she had swallowed it all completely. I 
said to her, "You did that because you were about to 
come, didn't you?"

She smiled, and said, "Yes. I'm not ready for that 
yet."

"Okay – you're ready to suck my cock but not ready for 
me to make you come. I'm not sure I really understand 
that."

But I actually did understand. Letting me make her 
come was a kind of surrender that she wasn't prepared 
to offer yet.

But there did come a day, months after we first 
kissed, and weeks after the marvelous encounter of my 
cock with her sweet mouth, when she agreed that she 
did want to try making love with me. We drove to a 
motel, and melted into each other's arms when we 
finally were alone in the rented room.

I was uncertain about how it would be for her. She had 
told me that she was capable of having multiple 
orgasms – but had also said that she had a hard time 
coming at all. I was hoping I could make her come at 
least once this first time that we were together – and 
was counting on having my skills as a lover at their 
peak on this special occasion. In the interest of 
saving time later in this narrative, let me mention 
some of those skills here: an ability to refrain from 
coming for long periods of time, a limited ability to 
come without ejaculating, which allows me to remain 
hard, and a limited ability to remain hard even after 
ejaculating so much that my balls are quite drained of 
all semen. (Those limited abilities have extended and 
improved over the two years that Lindsey and I have 
been lovers.)

Returning to that motel room, where Lindsey was alone 
with me in a safe, secluded place for the first time: 
we kissed passionately and caressed each other through 
our clothes for what was probably a couple of minutes. 
Then we began undressing as fast as we could – Lindsey 
was much faster than I was – and we climbed into bed. 
Now I was able to caress every part of her lovely, 
lithe body – and I took advantage of the opportunity, 
savoring the feel of her soft, smooth skin and the 
shape of the lovely curves on her body and her legs. 
Then I put my mouth over one of her nipples and began 
to suck it hard, as she had taught me that she enjoyed 
so much. 

I took her nipple gently between my teeth and pressed 
them together and was rewarded with a sigh of pleasure 
from her sweet mouth. At the same time, I took her 
other nipple between a thumb and forefinger and 
squeezed it hard, just the way she liked. After a 
moment, I slid my hand in a long caress down over her 
tummy and then around to cup and squeeze one cheek of 
her firm, shapely ass, and then reached further around 
her to give the other cheek the same treatment. 

Lindsey was sighing and softly moaning throughout, 
while holding my face against her breasts while I 
alternately sucked and lightly chewed on one and then 
the other. While I was caressing her ass, Lindsey 
moved her hand down to my cock, which was so stiff and 
hard that it was lightly pulsing in time to the rapid 
beating of my heart. She made pulling motions on my 
cock, signifying perhaps her impatience to have it 
penetrate her pussy. But my plans of making her come 
involved making her wait a while longer, perhaps 
beyond the point that she might feel she could stand.

I began caressing her thighs – tops, sides and backs 
in sequence, then lightly touched the insides of her 
thighs, about halfway down, and stroked softly 
downward toward her knees. There my hand lingered, 
just above her knees, on the insides, alternating 
between caressing each of her thighs in turn. The 
shape and the firmness of her thighs are so delightful 
that merely touching her in this way gave me immense 
pleasure. 

After a minute or two of such an enjoyable prelude, I 
began to move my had along the insides of her thighs, 
first on one then on the other, and then began 
caressing the insides of the tops of her thighs, just 
next to but not quite touching her pussy, again first 
on one side and then on the other. On the third or 
fourth pass from one side to the other, my fingers 
brushed against her pussy lips. Then on the next pass, 
they lingered lightly there for just a moment before 
moving back to her thigh. 

Lindsey was writhing with anticipation and desire and 
all the while was pumping her hand up and down on my 
cock, urging me to get through these preliminaries 
more speedily. Finally, after teasing her beyond 
bearing, perhaps, I inserted two fingers between her 
outer pussy lips and slid them up to her clit. A 
circular motion of my fingers against her partly-
hooded clit, lightly, lightly, elicited a soft moan 
from Lindsey, something that was intensely rewarding 
to me.

After a few more moments of pussy play, caressing her 
inner lips, inserting two fingers inside her pussy up 
to a couple of inches, exploring the slick entrance 
where I expected to experience even more gratification 
in a very short time, I rolled over on top of her and 
between her thighs, placed the tip of my cock just 
inside her pussy lips, and began rhythmically 
inserting and almost withdrawing about an inch of my 
cock into her pleasure chamber. 

Lindsey wrapped her arms around my ass and her legs 
around my legs and began trying to pull my cock 
further into her pussy. But I wasn't finished teasing 
her quite yet, and continued with my insertions and 
partial withdrawals, gradually increasing the 
insertion to perhaps three inches. Then I paused for a 
moment at a point of near-withdrawal – and finally 
plunged my full seven-inch length into her, reaching 
for the furthest point of the interior of her pussy.

This sudden insertion of the full length of my shaft 
elicited a somewhat deeper but still soft moan from 
Lindsey, followed by a sequence of panting and soft 
moaning that she kept up for the whole time that my 
cock was in her pussy. At first, I maintained my 
insertion to its fullest extent, moving my cock from 
side to side within her, pressing my body firmly 
against her clit, then rotating my body against and 
around her clit. 

After a few moments of this, I began partly 
withdrawing and then pounding into her rapidly and 
repeatedly. Then I pressed my cock firmly into her to 
its full length again, exploring the interior of her 
pussy. From time to time, I felt the tip of my cock 
run up hard against a slight protuberance at the 
fullest depth of Lindsey's pussy. I thought this must 
be her cervix – but she didn't seem to experience any 
discomfort, and perhaps even intensified her moaning 
and panting, so I began to seek that spot out for 
repeated bumps with the tip of my cock.

For a long time, I alternated hard pounding into 
Lindsey's pussy with times when I pressed my cock into 
her depths while pressing my body against her clit. I 
deliberately held off on coming, in order to try to 
make sure that Lindsey came. (If I told you how long 
this went on, you would think I was lying – so let's 
just say it was a long time.)

Throughout this entire long time, Lindsey kept moaning 
and panting continuously. So it seemed pretty obvious 
that she hadn't come. I was beginning to be exhausted 
from my efforts as well as somewhat disappointed and 
discouraged, so I decided to build up to an orgasm 
myself and then to postpone further attempts to bring 
Lindsey off to another occasion. 

The wonderful part for me was that I really was 
extremely turned on by Lindsey's beauty and the sexy 
way that she was moving while I varied the ways that I 
was thrusting into her. So coming for me was just a 
matter of loosening the tightness in my groin that I 
use to control my orgasms. It wasn't long before I 
began to spurt into her, continuing my thrusting in 
and out in time to the pulsing of my cock. When my 
spasms and spurts were over, I began to slow down my 
pace, and then stopped, with my cock pushed deep 
inside of her and still fairly hard. Her panting and 
moaning also slowed and then stopped.

With what seemed to be the last of my strength, I 
rolled over, pulling Lindsey on top of me without 
withdrawing my flagging cock. "My darling," I said, 
"I'm sorry you didn't come, though it seemed like you 
were about to the whole time."

She laughed and said, "Bob! I started coming the 
moment you thrust deep into me – and I never really 
stopped until just now. That was the most amazing 
experience I've ever had!"

"I wish I'd known that, Lindsey – though I might have 
stopped sooner. You really wore me out!"

She laughed again, delightedly, "I'm very sorry you 
didn't know, and sorry you're worn out – but I'm very 
glad you didn't stop!"

That day has lived on in my memory as the start of the 
most beautiful period of my entire life.

***

Postscript to Chapter One – When Lindsey read this 
first installment of our story, she wrote the 
following in an email message to me ("little bob" is 
her nickname for her vibrator: "I read the 1st chapter 
then spent about 5 -10 minutes with little bob and had 
3 orgasms. 

I still vividly remember the tantalizing torture you 
put me through, your hands on my thighs and skimming 
over my pussy and your fingers teasing. When you put 
the tip of your cock in, teasing and then entering me, 
it was like an explosion of my senses, everything 
stopped and blurred, my insides constricted and seized 
in ecstasy and then released making the universe a 
vast and glorious new realm to me and it didn't stop 
until you did. Sorry for your exhaustion."

To be continued?

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 75