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From: johndoe1999@my-dejanews.com
Subject: It happened! (MF, anal)
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Like every other day she labored at the office, sitting at her desk,
thinking about the upcoming holidays she had been looking forward to.
She sat there wondering what the afternoon would bring, she would finish
at 4 and then head over to a friends house, whom she occasionally had
sex with and then head home to her husband.  This had been going on for
a year or so, maybe once a week whenever possible.
Lately, it has been harder and harder to get together, but they still
managed at least once a month.  Today was the first day in a month she
would be heading over to his house and as usual thoughts were going
through her head of the afternoons coming encounter.  As 4 approached,
she began to get more and more interested in the coming encounter.  She
knew that he would have been thinking about it all day as well, and she
wondered which interested her, what he had in mind today.
John was always thinking of what he would do, or wanted to do whenever
he met with Jane, but seldom ever went as far as his imagination had
taken him before her arrival.  Some days he wanted to have sex with her
the minute she walked through the door. Other's he would picture them in
different places around the house, or outside in the yard or maybe some
form of bondage.  Today he thought, let's try something we hadn't done
yet...but what.
Jane arrived at 4:10 after work, she was her usual tired, but spoke of
her day at work.  She told him that she had to leave by 6:30 to go home
for dinner.  For about a half hour they worked at the computer and then
it began.  Slowly at first, Jane was wearing a skirt which had found
it's way up her thighs, aided by his hand.  It was a thin cotton skirt,
and John could feel her through it very easily, almost as though she
wasn't wearing anything.  That is one thing John liked about skirts,
they are usually very thin and leave a whole bunch to the imagination,
never mind what is at the top of one.   John was slowly working his way
up her thigh as they worked.  Jane didn't seem to object, she watched
the computer and reclined into the chair.  This made John's efforts that
much easier.  John had worked his way up to her her panty line, he was
slowly rubbing her through her panties now.  Jane had closed her eyes
now and was not watching the screen any longer, but focused on what was
now happening to her.  The computer still hummed, but neither of them cared.
John was still rubbing Jane through her underwear and had found that
they were now getting moist and definately warm.  John continued working
his hand under her skirt, and then shifted himself so that he was
kneeling at the foot of the chair, right in front of Jane.  Her skirt
was right at her crotch now, barely covering her.  Occassionly John
could catch a glance of her underwear. and keep see the dampness forming
where he was rubbing.  Jane's breathing had increased and was enjoying
the rubbing, but she wanted more.  John was now fully under the desk,
Jane was still able to read the computer when she opened her eyes, which
was now happening less and less frequently.
John while under the deck, had pulled Jane's underwear aside now and was
rubbing her directly with his hand.  Jane wanted more and was pulling
his head closer, and down.  John found this somewhat erotic, Jane was
essentially fully clothed and yet he was rubbing her skin.  The clothes
were on, but not in the way.  John was ready to kiss Jane, what she
wanted.  John lowered his head to her crotch and could feel the warmth.
John began to lick her and found her extremely moist more so than he
could remember.  She had once told him that she enjoyed to surf and
masterbate, so maybe this was even more pleasurable, surfing while
having someone lick her.  She was moaning now, but occassionly John
could hear the mouse click and the hard drive read, she was still
surfing.  John had worked a finger into his oral sex, he continued to
lick and penetrate with his tongue, but was now using his finger to
please her.  Jane was excited and John sensed this and inserted a second
finger.
John and Jane both knew each other like it a little rougher than normal,
so John was getting a little rougher with Jane and she could sense it.
After only a few minutes, John had worked another finger into her, it
wasn't easy, and it hurt a little, but the hurt was good and John knew
that.  Jane began to squirm a little more, she was enjoying the tonguing
she was receiving but the three fingers she was also receiving concerned
her.  It felt good, but in a painful kind of way.  She wouldn't want
this to go on for very long but could take it for now.  After a minute,
it felt very good, she hadn't been filled like this before and enjoyed
the unusual sensation.  Three fingers were working inside her
rythmically now, and John continued to lick and suck her genitals all
over, She began to sense a familiar feeling growing deep inside.  Her
breathing continued to intensify and John could feel her growing
excitement.  Jane was entereing into her orgasm and was holding John's
head and encouraging him to lick faster and suck harder through her
breathing as her orgasm built.  John slowly inserted a fourth finger for
the las minute of Jane's orgasm.  He knew the second it was over he
would have to remove his fingers, as she grew sensitive.  But for now,
even Jane was enjoying this pain mixed with orgams and finally came,
sqeezing John's head and holding him place.
JOhn could sense her orgasm had died down and knew she would need a few
minutes to calm down, She baceme very sensitve after an orgasm.  John
then threw a surprise at Jane, he stood up and moved her to the floor,
Jane couldn't figure out what John was doing.  He pushed her face down
and was kissing her back, she still had her dress on, but it was around
her waist and she could feel that John was very hard even through his
shorts.  Jane reached around and began to rub at John's now erect penis.
She was still lying on the floor with John on top of her, but she was
now comfortable.
John was now, moving and kneeling up behind Jane, he reached over and
placed a pillow under Jane's stomach.  She couldn't figure out what was
happening.  She then heard, the familiar sound of the jar she kept in
her purse opening.  She had it in there, after a conversation she had
with John, she had condom's and KY jelly.  John must have found the KY,
and brought it into the computer room.  Jane lied face down on the
floor, still holding John's pulsing member, she had a thought of what
was about to happen but couldn't believe it, she thought it would happen
in some other way, maybe a quiet hotel room, but here on the
floor...should she object?  John had moved down Jane's body now, and was
slowly licking her ass, he was kneeding it with his hands, pulling it
apart and squeezing it as he licked up and down her crack.  Jane had
anal sex with her husband, but never with John, she did however
recognize the foreplay was leading towards this.  She and John had
discussed it but never really said much about it.  John, was now licking
an sticking his tongue into her hole, she realized that although she was
scared and nervous, she was enjoying the hell out of this so far.  John
was easing his tongue into her and she was wet, she knew that, she was
also able to reach around and play with her self, and she knew that John
also liked that.  She had a renewed excitiment now, the sensitivity from
earlier had worn off.  Jane could now hear John dipping his fingers into
the KY, she wasn't sure how far he would go with this at this time, was
he only going to place a few fingers in her or try and fuck her.  She
was excited and afraid but didn't say anything, she didn't want to know.
John had slowly worked a finger into Jane, he could sense that he needed
to go slow.  Before he even pushed his finger in, he thought to himself,
nothing could ever fit in there.  He had placed his fingers there
before, while they had sex and realized to his enjoyement that she liked
it.  He just wasn't sure how much.  Was she only tolerating it, or did
she actually like it too?  I guess we'll find out, he thought.  Jane was
comfortable, she knew that John would soon be inserting a finger in, so
she worked on herself rather vigourously, she was excited and thought
this rubbing would help in case of pain.
John was easing his finger into her now, a centimetre at a time, he was
using his pinky and  it was only a couple inches long and 1/2 inch
around.  He knew from before that he had to go slow, but after about a
minute, this finger was lodged into Jane all the way.  He held it there,
not moving it at all, just letting her get used to the fit.  She was ok,
and indicated so, the KY had made all the difference, previously they
never used any, this made it feel much better.  Jane was feeling
comfortable but still nervous on what lay ahead.  John slowly withdrew
that finger and re-inserted it several times Jane's butt was now totally
used to having something in there.  It stayed the right size until the
finger was reinserted.  After a few minutes of this Jane could feel a
second finger at her opening.  She quickly rubbed herself to offset the
pain, but it didn't work, she felt the second finger at the opening with
one finger still inside.  She was anticipating the wave of pain to come,
it had been awhile since there was anything in there.  She could also
hear the KY as it was slopping around back there, that was a familiar
noise, reminding her of her husband as he was the only person to go back
there...til now.  John slowly inserted the first few centimeters into
Jane, she squirmed, as there was already one finger in there.  But it
fit, and John didn't dare move for what seemed like an hour, he was
trying to let her get used to this new intrusion.  Jane had other ideas,
she moved back, the constant rubbing of herself, had elevated her
excitement beyond what John was thinking.  She wanted more, and took it
upon herserlf to push back ever slow slightly to take another few
centimeters inside.  Now John realized that a simple repositioning of
his fingers would allow him to place them side by side inside.  John
struggled to do that, but the tightness proved difficult, after all he
didn't want to hurt her.  Jane was lying on the floor, still except for
the rubbing she was doing on herself, she didn't say anything, it is if
she was just waiting for something to happen.
After another minute of resting his second finger inside, he began to
move it in and out in unison with the first finger, Jane was lightly
moaning, obviously.  The pressure was pretty good, but still difficult
John applied more KY to his fingers.  Afterwards John could feel Jane
was more comfortable and in fact was moving back and forth on his
fingers, she was ok with two fingers.  John knew that this was his
chance, he began to lather up his dick with KY.  It was twice as
lubricated at his fingers and began to kneel up more.  Jane was still
rubbing herself but was aware that John just shifted and knew what was
coming, she was tense.  She could still feel the two fingers in her ass,
but didn't know what having John dick in there would do for her, it's
different she thought to herself.
John was now at the right level, he was moving his dick around on her
butt, and he still had two fingers inside her, he slowly placed his
penis at the opening to her butt, and met his fingers.  Jane was still
rubbing herself and some of the KY was finding it's way down there so
she was feeling pretty good.  John was moving his fingers in and out of
her rather well now, she had adjusted to the second finger quickly.
John was thinking got to do it soon, or she is going to get sore from
all the action already.  So he withdrew his fingers on one of the out
strokes and placed the head of his well lubricated dick in it's place.
Rather that insert it though he just let it sit there against the now
open butt.  Slowly he was able to position his dick in the exact place
it was needed to enter.  Jane was waiting anxiously, to see what
happened next and could only think, go slow...it's been a while.  John
eased his penis into the hole, so he thought, it was really only pushing
at the hole, not entering.  Jane was really holding her breath now as
she knew that there was a little bit of a push required to gain
entrance.  John realized this as well and eased a bit of the head of his
dick inside, Jane now realized there was something inside, just barely.
John had pushed about 5 centimeters into her, still hade several more
until the head would pop in, and thought once it did things would be
more comfortable.  Jane was still rubbing and trying to relax, John
threw more KY into things and tried to push more in, But it was hard and
he could hear Jane groan, mostly pain, but maybe some pleasure he
thought, but he wasn't sure.  John moved back and allowed jane to catch
her breath, and john pushed a finger inside, this was relaxing for Jane
and much smaller, after 30 seconds, John removed this finger and tried
to push himself into Jane again.  John's hands were covered in KY and he
attempted to massage her whole butt while still pushing himself inside.
It worked a little better this time, Jane was able to take nearly the
whole head of his penis, John rested for a second and then said, to Jane
that he was going to just push a little once she was used to this new
thing, and get ar least the head inside.
John was ok, but Jane was tense, she was breathing hard and trying to
pull herself apart while still rubbing herself, trying to create some
pleasure, and she was successful on both fronts as the whole head pushed
in.  Jane felt some relief  but was still getting used to the size in
her ass and it was hard, John couldn't believe the tightness, and feared
moving or else he would come.  This was the case whenever they had sex,
John found Jane tight vaginally and couldn't control his self the way he
wanted, expecially on his first orgasm.  This time however it was really
tight, but exciting and his heart was pounding.  Once inside John was
motionless allowing Jane to set the pace, if she wanted more or less she
would move.  After a minute, John thought it time to try some rythym.
He began to move ever slow slightly in and out, barely moving on the
whole and inch.  Jane was moving on the floor and seemed in some pain,
but also enjoying it.  John reached around and found her hand still
moving on herself, so he moved up and found a breast.  Jane was stil
wearing her dress, which John found erotic, it covered her back right to
her ass.  He was able to reach into the buttons on the front and unclasp
her bra, something she would never really let him do especially in the
almost full light of this room.  When he reached forward to play with
her breast he moved up and into her another few centimetres.  She
reacted with a deep breath, but not with as much pain as before.  She
was finally getting used to his size.  John was now moving his hands
from breast to breath, her nipples were fully erect and he was easily
able to play with them and she enjoyed this, and John could sense it.
John was finally able to move within her somewhat freely, when he pulled
back he always left the head in, to avoid any unnesessary pain, but he
was also re-lubing himself with KY every minute or two.  John could now
fell he was going to cum.  He did was to however go all the way in at
lease once, before stopping.  John was now able to pump in and out of
Jane, it was rough and tight, but it worked.  After halfway in, John
could feel some tension, but he really wanted to go all the way at least
once, so he slowly on each down stroke, pushed into this barrier each
time he did he could hear a breath escape Jane.  Finally he was 3/4 of
the way in and couldn't hold back much longer, and he knew it, it was
just too tight and too much friction.  So he pushed in sending Jane all
the way to the ground, there was not where to give except inside, so she
did.  He lied on top of her for a minute, full weight, all the way
inside.  A tear formed in her eyes but she knew it was almost over, and
she rubbed herself trying to cum, slowly she could feel herself having
another orgasm, she could also feel John beggining to twitch.  Then it
happened, John exploded in a huge orgasm, he felt the cum shoot out of
him with a huge relief and even bigger force, it was oozing out of
Jane's ass.  Jane while John was still buried all the way in her,
started to have her own orgasm, something she didn't think would ever
happen from anal sex, but it did.
After a minute, John started to get up, and ease himself out of Jane,
she moved to help, not much was said.  Jane's dress was soaked in sweat
and this turned John on again, her back was drenched under dress and her
ass sitting there was glistening in the dew.  John was fully out of Jane
and they lied side by side on the small patch of floor they had.  He
said, surprise!  they kissed and didn't say much for the rest of the
night until she left.  Jane turned to John before she left and said, I
guess we've added something else to our repertoire now!  See you Tommorrow!

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