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Dorothy's Story, Or We're Not in Kansas Anymore - 1
by James (jamesmc6243@yahoo.com)

***

This 14 part story is based on fact, the events really 
did happen. Dorothy – her real name – and I – James, 
had an affair that lasted almost seven years. During 
that time she became a very willing, a very active, 
and a very imaginative participant. She moved from 
"missionary sex" to "group sex" and on to "family 
sex." (MF, exh, voy, 1st, affair)

***

Author's Note: The above events happened in the late 
'80's and early '90's. I had written about the events 
as they occurred. Then about 5 years ago we had a 
house fire and I lost everything – narratives, notes 
and photos. So what you are reading is the best I can 
do at reconstructing things as I remember them. I have 
taken literary license but rest assured that this is 
not some fantasy. I do not encourage anyone to engage 
in any of the sexual activities I have related. If you 
would like to email me, please do so 
jamesmc6243@yahoo.com.

***

PART 1: The Beginning

Dorothy and I had an affair that lasted almost seven 
years. She was and is a very neat lady, we have 
managed to maintain some contact through the internet 
but currently we live at opposite ends of the country. 
When we first started seeing one another the objective 
was sex, pure and simple sex. She had had affairs 
prior to me and at first she was reluctant to discuss 
them but gradually became more willing to reveal 
particulars. As far as our sex it was relatively 
straight-forward. I mean to say, we fucked in 
different positions and we did engage in oral sex but 
beyond that it was pretty "normal". 

But after a few months of seeing her, I began to sense 
that she might be willing to try different things and 
that she might be induced to be more adventurous and, 
the truth be told, I was more than willing to indulge 
her. Dorothy was married and 37 years old when we 
started seeing each other. She was 5' 7", weighed 
about 145 pounds so there was some substance to her, 
she had smallish tits, 36 C's, a nice firm well filled 
butt, and was very attractive with dark brown hair and 
eyes. Her tits were firm enough that she could go 
without a bra and most people would not notice. All in 
all, she was a very pretty woman who would, over the 
period of our affair, came to love sex in all its 
variations. 

As I said, she had revealed that she had fucked ten 
other men in addition to her husband. He was something 
of a "cuckold" because, according to Dorothy, he knew 
of five or six of her affairs and had done nothing to 
interfere. In fact, she once told me, he seemed to 
enjoy the fact that other men were fucking his wife. 
His name was Jack and they had an 18 year old son – 
Gregory, and a 17 year old, soon to be 18 years old, 
daughter – Kathy.

Some examples of her "signs" included a greater 
willingness to discuss her other affairs. I knew a 
couple of the other fellows but never discussed her 
with them. In addition to the discussions, another 
sign was her increasing desire for me to play with her 
asshole. Several times I had managed to slip a finger 
into her asshole and she always moaned indicating to 
me that she enjoyed it. Eventually I was able to 
convince her that having her butt fucked was truly 
enjoyable and, as it turned out, she ended up agreeing 
with me and became a lover of anal sex. If you read 
the additional chapters you will find out that her 
first experience with anal sex had been a rather 
painful one. But, with the proper preparations, she 
soon enjoyed it so much that she even presented her 
asshole to her husband on one occasion to fuck and he 
refused. However, he eventually became a big advocate 
of butt fucking. 

Another example of her signs happened one day when I 
kidded her about shaving her pussy. When we met the 
very next time, she had shaved her pussy bald. I had 
also commented to her that I thought it was very sexy 
for a woman to go around without panties and, sure 
enough, when she and I would get together she would go 
without panties. So, as I was interpreting things, she 
was giving me encouragement to expand her sexual 
horizons.

What happened one afternoon as we were driving on the 
belt line around Raleigh was the event that tipped the 
scales for me and led her to a more adventurous sex 
life. I told her that I would really like for her to 
give me a blow job. I was driving and we were in a 
Dodge van so there was leg room between the two front 
seats. Dorothy grinned at me, turned in her seat, 
reached for my crotch and began to fondle my cock. She 
soon had hard and she started to undo my slacks. 

I put my hand on her hand and stopped her 
ministrations. "You know what I would really like," I 
asked her? She shook her head "no." "Well," I replied, 
"why don't you unbutton your blouse and take off your 
bra." She smiled and willingly complied. "Pull your 
blouse wide open," I told her and she did fully 
exposing her tits to me. I reached up and tweaked both 
of her nipples which were hard. 

"Now," I commanded her, "keep your shirt open like 
that and when I pull up alongside that semi up there, 
I want you to turn in your seat and flash the driver 
your tits, okay?" 

She stared at me for a moment and then said, "Does the 
idea of someone else seeing my tits turn you on?" 

"Uh, huh," I replied, "it sure does. Does it turn you 
on too?" She nodded her head and if her grin could 
have gotten any wider it would have. 

I accelerated and moved nearer the truck and then 
matched speeds with it so her window was alongside the 
trucker's door. Dorothy turned around; faced the 
window, then leaned forward so that her tits were 
fully exposed to the driver. 

"Is he looking at you," I asked her? 

In a breathless tone she said, "Yes, he is!" 

"Cup your tits for him, bounce them in the palm of 
your hands," I told her. She did as instructed. 

"Is he still looking," I asked again? She nodded her 
head and said, "He obviously likes what he sees since 
he is grinning and making the 'okay' sign!" 

"Okay," I said, "wave bye-bye to him!" When she had 
done that, I slowed down and moved to the right so I 
could exit the highway. As we approached the exit, I 
told her she could put her bra back on and button her 
blouse.

Dorothy was smiling and her face was flushed as we 
turned on to the surface streets. She had finished 
putting her bra on and buttoning her blouse and 
settled back in the car seat. 

"Did you like doing that," I asked her? 

"God," she replied, "I wasn't sure about it at first, 
but I got so turned on doing it, I swear my pussy was 
leaking like a sieve." 

"Hmmmm," I commented, "so it would be safe for me to 
assume you might like to do that again and maybe even 
show more?" 

She looked at me, smiled and then slowly nodded her 
head. 

"Would you be willing to show your pussy?" She nodded. 

"Maybe even put on a show for a couple of guys?" She 
nodded again. 

"I kind of thought you might like that and I am glad 
you did enjoy it. Maybe the next time we are out and 
about, we can have some more fun," I told her. 

She nodded and then said, "You know, you never got 
your blow job!" 

I laughed and replied, "Yeah I know but how about I 
take a rain check?" 

She was quiet for a moment and then said, "Are you 
busy at lunch time tomorrow?" I shook my head 'no' and 
she said, "How about we have lunch tomorrow and maybe 
take a little extra time, okay?" We were approaching 
her office and I said "Sure, about 11:30 in the 
morning until about 1:30?" She put her hand on my cock 
and said, "You have a date." 

After I dropped her off at her office, I must admit I 
spent the rest of the afternoon and a good portion of 
the evening planning some "shows" for her. My 
imagination was running wild but I knew I had to take 
things a little slowly otherwise she might balk and 
that could be the end of things. Right near the end of 
the day, I called her and told her that I would like 
her to wear something sexy but especially to make sure 
she was wearing a garter belt and nylons. She giggled 
over the phone and assured me she had been thinking 
along the same lines and would dress as I had asked. 

***

The next day, as we had planned, I checked out of my 
office at 11:30 and drove over to pick her up. She 
came outside and I saw that she was wearing a fairly 
short skirt – not a mini skirt as that would have been 
inappropriate for her office but a short one never-
the-less. She was also wearing a silky dark blue 
blouse. As she got into the car, I caught a glimpse of 
white thigh above her black nylons and it was plain 
that her nipples were very hard. Once in the car, she 
turned slightly in her seat, checked to make sure no 
one was near and lifted her skirt revealing black 
nylons, black garter belt and a bare pussy.

"Hmmmmm," I said, "you look delicious!" 

"What are we going to do," she asked. 

"Well, we are going to do some shopping over in 
Durham, I think you will like that." 

As we drove the twenty minutes or so to Durham she 
relived the previous flashing she had done. As much as 
I would have liked to watch her flash another driver 
or two, I remained committed to taking things slowly. 
She told me that she had dreamt about flashing the 
trucker and had woken up having an orgasm. She 
admitted that this had never happened to her before 
but she hoped it would happen again because, as she 
said, "…it was a wonderful way to wake up…" Dorothy 
was very animated as she talked and it was obvious she 
was excited about the prospect of doing whatever it 
was I had planned for her.

I knew about a small shoe shop near the downtown area. 
I had come across the place quite by accident but had 
learned that it was a quiet little store. As I parked 
the car, I asked her, "How do you feel about shopping 
for some shoes?" 

She smiled and replied, "That is something I really 
enjoy doing." 

Before we got out of the car I explained some of the 
ground rules to her. I had her turn in her seat to 
face me and began to stroke her thighs. I asked how 
she would feel about being told to do things, things 
she might not ever had considered doing. 

She asked me for some examples and I mentioned putting 
on a show for a group of men and having sex with me 
and one or two other men. 

She went quiet for a moment and then said, "You know, 
I have thought about doing wicked things but couldn't 
figure out how to set them up. So yes, I would be 
willing to do whatever you wanted me to do." 

I smiled at her, "That is why you have me, I have some 
experience in these areas and know how to get things 
done." 

Then I told her I would never put her in any kind of 
danger. I suggested some kind of code she could use – 
we decided she would hold up two fingers in the "V" 
for Victory sign – whenever she felt she was getting 
in over her head. I assured her that when I saw the 
sign I would put a stop to whatever was going on and 
we would leave. 

As it turned out she never used that code even with 
all of the things I eventually had her do. Then I 
said, "Given these precautions, are you willing to do 
whatever I tell you to do? Understand, I mean if I 
tell you to do something you will HAVE to do it." 

Dorothy was quiet for a moment and then said, "You 
have me so turned on right now, I would be willing to 
do anything and everything you want me to do." 

I smiled at her and said, "Good, then let's go do some 
shopping." We got out of the car and, as we walked 
toward the front door of the store, I patted her on 
the ass.

As we walked inside a little bell over the door 
tinkled announcing our presence. It was cool and a 
little dark and we were the only customers. As we 
looked at the different styles of shoes on display, 
the owner of the store came out from the storage room. 

"How can I help you folks today?" he asked. 

It was at that moment that I spied a pair of four inch 
black high heels. I picked one up and asked, "Do you 
have these in white and in, what is your shoe size 
honey?" 

Dorothy was caught a little unawares but then 
stammered, "Seven and a half, regular." 

The owner had been looking at her feet and said, "Yes, 
that is the size I would have guessed and I do have 
them in white. Let me get them for you." 

He walked back into the storage room and I maneuvered 
Dorothy so that we were sitting in the row of chairs 
closest to the storage room and facing away from the 
front door. As we sat down, I pulled a foot stool over 
in front of her and whispered to her, "Put your foot 
up on the stool and pull you skirt up higher." 

She did as I had instructed her. Then I placed my hand 
on the inside of her thigh right at the top of her 
nylons.

The owner came out, was opening the box and was 
speaking as he was walking, "My name is Steve and I am 
sure we can find something the lady will like." He sat 
down on the stool in front of her. As he leaned 
forward to help her take off her shoes he finally 
noticed that he could see up her dress and was staring 
at her naked pussy.

He kind of stammered a little but then a large grin 
broke out on his face when he realized that my hand 
was on her thigh. As he slipped the shoe on her foot, 
Dorothy spread her legs farther apart letting him see 
more of her pussy. He glanced up at her face and then 
his eyes dropped back down to her tits. Her nipples 
were pointing like small arrows out of her blouse. 

She lifted her other foot, further spreading her legs, 
so he could help her put on the other shoe. 

"Why don't you try walking in them," I suggested. 

Dorothy stood up and walked away from us. She 
commented on how comfortable the shoes were and 
wondered what it would be like to walk in shoes that 
had even higher heels. 

As she was walking around, I leaned toward Steve and 
whispered, "How would you like to see more of her?" 

His head whipped back from following her to look me in 
the eyes. I know he was wondering if I was putting him 
on so he wasn't quite sure how to respond. 

"Really," I said, "how would you like to see more of 
her?" 

His grin spoke volumes as he nodded and said, "Yes, 
definitely!" 

"Can we go into your storage room then," I asked him? 
He again nodded. I turned in my chair and said, 
"Dorothy, Steve thinks he has another pair of shoes 
you might like in his storage room." 

She turned to look at me and I noticed that she was 
somewhat flushed in her face. She nodded, Steve and I 
got up and the three of us walked into the storage 
room. Once we were inside and away from the door we 
all stopped. 

"Sweet heart, why don't you take off your blouse," I 
said? She looked at me and then very slowly and very 
seductively began to unbutton her blouse. Steve's eyes 
were riveted on her hands as she undid each button. 
She pulled the bottom of the blouse from the waistband 
of her skirt and then unbuttoned the last button. She 
slowly slid her blouse down her arms as I reached 
behind her so I could hold it for her.

Steve was staring at her tits and Dorothy seemed to 
love every minute of this adventure. 

"Honey," I murmured, "why don't you take off your 
skirt so Steve can see your pussy and ass?" 

Dorothy surprised me and, as she told me later, 
herself when she said, "Steve would you like to see my 
cunt and ass?" 

Steve, for his part, was only able to nod his head 
yes. 

She reached behind herself, undid the clasp on the 
waistband of the skirt and then slipped the zipper 
down. She was holding the skirt by the waistband and 
then suddenly let go. The skirt fluttered to the floor 
and she was standing in front of me and a stranger 
nude except for her shoes, nylons and garter belt. She 
stepped out of her skirt and I picked it up, laying it 
on a stack of boxes next to us. 

Steve stared hard at her body and then, in a husky 
whisper, said, "You are one great looking woman!" 

Dorothy slowly pirouetted so that Steve was able to 
see her ass framed by the stays on the garter. 

At that moment the little bell tinkled and Steve 
started with a perplexed look on his face. "I'll get 
rid of them quickly," he said. 

I shook my head "no" and told him that we would stay 
in the storage room while he handled his other 
customer. I also told him that Dorothy would stay nude 
until he came back. His head bobbed in acknowledgement 
and he walked out to the show room. 

I whispered to Dorothy, "Are you okay so far?" I 
wanted to be sure she was still enjoying herself. 

She nodded and then reached for my hand, "Feel my 
pussy," she said. She spread her legs apart and I 
slipped first one and then two fingers into her very 
wet cunt. "Yes," she purred, "I am really enjoying 
this!" 

I continued to finger her pussy and then, as I slipped 
my fingers from inside her said, "Stand up, turn 
around and bend over!" Without any hesitation, she did 
as I had instructed her. I placed one of my cunt slick 
fingers on her asshole and then slowly and 
deliberately pushed it into her asshole. I heard her 
suck her breath in but she didn't resist in the 
slightest. I finger fucked her asshole for a moment or 
so and then heard the ringing of the cash register. I 
pulled my finger out as Dorothy straightened up and 
sat back down. 

As Steve walked back into the storage room, I said, 
"See, no change, she is still naked for you." He 
grinned at me and nodded. 

I decided to push the envelop a little farther. "If 
she lets you play with her tits, would you give us a 
discount on the shoes?" 

At that Dorothy looked at me with a bit of a 'deer in 
the headlights' stare, looked and smiled at Steve and 
cupped her tits for him. 

"No," he replied, "I won't give you a discount but I 
will give the damn things to you for free if I can 
play with her tits." 

Without any prompting, Dorothy leaned forward 
slightly, took his hands and placed them on her tits. 
Steve began massaging them and then rolled both of her 
nipples between his thumbs and forefingers. She let 
her head roll back and it was patently obvious she was 
enjoying his ministrations. 

After a couple of moments he asked, "Can I kiss them 
and suck them?" Before Dorothy could reply I said, 
"Yes, go ahead, kiss and suck her titties, she'd love 
that, won't you dear?" 

Dorothy murmured, "Yes, please do as James says." 

As Steve leaned in and took one of her nipples between 
his lips, I knew then that Dorothy would agree to do 
just about anything I might ask of her. My own cock 
was ridged and as hard as I could ever remember it 
being. I let Steve enjoy her tits for several moments 
and was surprised – although I shouldn't have been – 
when Dorothy had an orgasm.

Steve was sucking hard on one nipple as Dorothy was 
moaning her pleasure. Her knees were quivering and I 
could see her ass cheeks rippling as the orgasm moved 
throughout her body. As she started to come down, I 
told Steve that he would have to stop and he did. 

He stepped back, his face flushed and it was clear 
that he had really enjoyed himself since the bulge of 
his cock in his pants was very obvious. 

I leaned over, pushed her legs apart and fingered her 
cunt in front of Steve. "Now then, Steve, since you 
enjoyed her tits, would you like to taste her pussy?" 

With that, Dorothy lifted one leg and draped it over 
the arm of the chair. Steve didn't reply, he merely 
knelt in front of her and began eating her cunt. 

Since I knew her reactions, I knew it would only take 
a couple of moments for her to cum again. I watched in 
a kind of detached way as another man licked and 
sucked her pussy. Sure enough, after a very short 
time, she started cumming and reached down to pull his 
head deeper into her cunt. Again, her body quivered 
with sheer pleasure. 

She moaned, "Oh god, oh god, I'm cumming again!" 

Finally, Steve pulled his head back and sat on his 
heels. "That was amazing," he blurted out, "simply 
amazing!"

I looked down at him and said, "Well, we are glad you 
liked that but we are going to have to go. Could you 
put her old shoes in the box for us?" He nodded, stood 
up, took one last lingering look at her nude body and 
then walked from the storage room. I gave Dorothy a 
couple of moments to compose herself and then told her 
to get dressed. She stood up, wrapped her arms around 
my neck and gave me a deep, passionate kiss. She 
pulled back, I handed her skirt to her which she put 
on and then helped her put her on her blouse. Wearing 
her new shoes we walked out of the storage room. 

Steve was grinning like a love sick boy as he handed 
the shoe box to me, "I hope you will come back soon," 
he said. 

I smiled at him and said, "You can be sure of that, we 
shall be back in the not too distant future." With our 
package under my arm, we walked out of the store.

We got into the car, I backed out of the parking space 
and started the drive back to Raleigh. 

When we were on the expressway, she looked at me and 
said, "That was the most incredible experience I have 
ever had, I swear that my two orgasms were among the 
best I have ever known." 

I smiled at her. "Well," I said, "if that is the case, 
I am sure I can dream up some more exciting moments 
for you." 

She reached across and put her hand on my still 
engorged cock. "You could use some relief couldn't 
you?" 

I nodded as she worked my zipper down and freed my 
cock. I have to confess that I was so turned on that 
she only had to work on my cock for a few moments 
before I erupted in her mouth. 

She swallowed every bit of my cum, straightened up and 
licked her lips, "Hmmmmm," she said, "that was a good 
lunch!" We both laughed at her joke. 

After another moment or two, I looked at her and said, 
"Do you realize what you have just become?" 

She looked at me with a confused expression, "No, what 
have I become besides a wild woman?" 

"Well," I replied, "you took some monetary reward for 
sexual favors so I guess that makes you something of a 
prostitute, right?" 

She was pensive for a bit and then said, "What would 
my momma think of her little girl being a hooker?" 

As she laughed I said, "And what would your husband 
think of his wife who was now my whore?" 

At that she laughed even harder and said, "He wouldn't 
know what to think!"

We made it back to work on time and, as I dropped her 
off at her office, I told her that I had to do some 
training out of town the next day but would like to 
have lunch with her the day afterwards. She smiled as 
she got out of the car, "You, my dear, have a date!" 
Unfortunately I had to call her the very next day and 
cancel our "date" since found out I had to go out of 
town but I did get her to commit to a rain check.

Dorothy's story continues in Part 2 – The Theater 

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
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 76