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Penetration
I had known him for several years, and in that
time we had become quite good friends sharing
many common interests and enjoying time spent
together alone and with friends. It was because
of our closeness that I selected him as the
first to take my ass.
This was a much considered decision on my part
as I had mixed feelings about having a cock in
my ass at all. On one hand I had heard all the
horrible things, mostly of the pain, that were
associated with someone getting fucked in the
ass. At the same time I had heard of the vivid
pleasures many receive from that very same
action. My dilemma was intrigue of the pleasure
but fear of the pain.
Some others I knew told me that in their
intimate time with him he was always gentle,
caring, and considerate when that was required,
but when the need was for rough, pounding,
insensitive fucking he was willing and capable
of providing that also. Whatever was needed by
his partner he gave willingly before he
satisfied his own carnal needs. The one thing
each of those people agreed on was at the end he
always reverted to his gently, caring, and
considerate ways.
I knew he was the right person to approach about
taking my anal virginity; an occurrence I had
resisted for many years. Some may ask why now,
and I can not fully explain because I do not
fully understand the signals from my psyche. It
came as if a cloud was lifting that suddenly I
was very curious about this aspect of human
sexuality I had passed by.
He was caught off guard when I approached him
with my request. Over the years he had on
occasion tried to initiate a more intimate
relationship with me and I had always refused. I
explained as best I could and he thought about
it for a few days before giving me his answer. A
caveat he applied was I must fully place my
trust in him and have total faith he would try
his very best to provide me a painless,
pleasurable experience.
The table of being off guard was turned when he
asked me: "What do you know of anal sex? I mean
what is the image that enters your mind when you
say ass fucking or similar terms."
I had not thought of it in those terms and was
unprepared to answer his questions. In a very
forthright manner, neither judgmental nor
condescending he spoke: "Until you have a clear
image in your mind of what you expect it is not
a good idea to proceed. Go investigate and come
back when you are ready."
For the next two weeks I pursued what avenues I
could to find the answers. I spoke with friends
of their anal experiences. Some loved it while
others said they would never do it again. No one
said the practice was wrong; those with negative
opinions simply said they did not find it
enjoyable. Another source of information was
written in the forms of journals and literature.
A last vehicle was popular pornography.
I again visited my friend telling him I now had
answers to his questions. To the first I gave a
detailed explanation describing the challenges
involved to prepare the anal sphincter to accept
the passage of a penis initially moving in the
wrong direction. I explained the need for
lubrication, and how if done correctly did not
have to involve pain or discomfort.
To the second question I told him of my desire
to avoid pain and how I wanted this event to
prove only enjoyable. "You will have exactly
that. Remember I am the guide. Arrive here
Saturday evening ready for a new experience, and
when it is time do everything as I instruct."
When I departed he handed me written
instructions on how to clean my bowel. "You may
want to do it differently in the future, but for
the first time let us not complicate matters
with your feces." On the way home I purchased
the enemas and other bowel cleaning substances,
and on Friday evening after reading the package
directions began the regimen he had directed.
I walked up the sidewalk to his house with an
empty bowel and what I thought boded poorly; a
raw anal opening. The enemas and laxatives had
done a thorough job, but at the cost of multiple
cleanings of the sensitive membranes guarding
the entry to my ass.
When we were seated in his living room he spoke
in a gentle reassuring manner: "Tonight is for
your ass. I will focus solely on actions and
techniques to bring you pleasure there. I will
not touch any other erogenous area; maybe in the
future, but not tonight. Are you ready? .......
Stand, take off your clothes, then follow me."
I arose and began to disrobe. As my body was
exposed he complimented me and commented how
long he had wanted to view me in this natural
state. When the last piece fell to the floor he
guided me to a room I perceived immediately was
solely for sex in all its shapes and forms.
"This is my play room and while there is much
here that may frighten you please do not be
alarmed. Sex has many dimensions; too many to
address without the proper accoutrements. In
that corner we will find what we need for this
evening."
In the corner, atop a large soft pad was a very
unusual appearing ottoman. It was carefully
constructed to provide the person lying over it
complete comfort while at the same time, so it
proved later, positioned the receiver at the
ideal height for his member to enter their body.
"Before you take your position do you want to do
this bound or unbound? You may find it easier to
relax if you are bound. If it makes you feel
uncomfortable I will release you." I thought for
just a moment then indicated bound. "Lay across
extending your hands as far toward the floor as
possible." Once in position he applied shackles
to each of my extremities locking me in this
vulnerable position.
The room temperature was comfortable and without
drafts. To aid the ambiance he had soft
instrumental jazz playing on the stereo at a
volume neither harsh to the ear nor difficult to
hear. The sweet scent of ripe peaches permeated
the room; a scent he knew I was particularly
fond of. My position on the ottoman was not
completely comfortable with my head hanging low
and when I told him he provided a padded stand
on which I could rest my head and upper body.
After I was repositioned he again shackled my
wrists. All was ready.
"This is the last I will speak to you. From now
on my touches will convey all that is necessary.
You may speak as you please."
I do not know what I expected, but it certainly
was not what I received. A soft, wet, warm cloth
began at my left ankle and moved upward washing
me. He did an area at a time never allowing me
to experience a chill and at the same time
relaxing me. I needed this caring attention
because despite my outward appearance I was very
tense. His awareness did much to ease my anxiety
and increase my confidence in him.
He washed and dried my entire exposed backside
with one exception; he did not approach my anal
opening. As his next task he began to lightly
caress my lower legs with his hands. Not too
hard and not to soft; the touches neither
scraped nor tickled. He ran his hands along my
legs feeling each surface, curve, and bend.
Nothing escaped his touch, and as he moved
toward the bottom of my buttocks his hands
stroked deep to the inside of my thighs, but not
deep enough or high enough to touch any other
sexual part.
Upward he continued massaging each buttock cheek
with firm, powerful strokes, but then he backed
away leaving me wanting. Where had he gone and
why? In a moment he returned drizzling warm oil
on to my back. The oil was so close to body
temperature I almost missed its presence, but it
was there and the passage of his hands on my
back was smooth; almost without friction.
From top to bottom and side to side he massaged
the tension and stress from my back. I have no
concept of how long he kneaded my muscles just
as I can not identify a point in time where he
again squeezed my butt cheeks. The transition
was effortless and unalarming, but this time
there was a difference as fingers on each hand
stroked the length of the crease between my
cheeks. If this was a normal massage such an
action would have no significance, but this was
not a normal massage. Instantly I became acutely
aware of his every move, but he proceeded as if
nothing had changed and continued rubbing oil
onto my backside.
Once again at my legs he applied the warm oil to
each and every surface first moving down one leg
then down the other with creeping slowness at
each progression. As he completed the second leg
he immediately began to move upward in the same
manner. I was so comfortable I am sure I napped
through most of his actions as I have no memory
of what he did until again his fingers moved
along my butt crease, but this time my
relaxation was such I did not flinch or react in
any way.
One more time he stepped away to gather warm oil
that he poured directly onto my buttocks. It may
have been moments or maybe hours that he pressed
the oil into my skin, I could not tell you, but
then another change occurred; his fingers began
to massage my anus. Gently, softly,
unobtrusively his fingers found their way to my
ass and with direct contact prepared it for the
next step.
I might have tensed a little bit, but it was
momentary as I quickly perceived no threat of
pain or discomfort. His index fingers alternated
in rubbing directly over the aperture pressing
slightly downward as they passed. It was never
deep, but it was deep enough that I recognized
the difference and I welcomed it. So much so
that as his fingers passed I tried to elevate my
buttocks and force the digit deeper. I was
beginning to crave penetration.
He knew my need better than I; just as he knew
how to heighten the sensations and increase my
desire. The progression was slow as he gradually
involved more and more of his fingers. Now as a
unit the four fingers on each hand rubbed across
the anal opening. Sometimes slow, sometimes very
slow the fingers passed feeling the different
texture of the skin and the tightness of the
ring beneath where it had begun to loosen.
A finger unit began its downward pass but then
stopped over my opening. It did not try to push
inward, but neither did it move onward. The hand
shifted slightly and a wonderful event happened;
one oiled finger slipped past the sphincter. One
of his fingers was able to feel the inside of my
bowel. The sensations were many including
interesting, pleasant, strange, but among them
was neither uncomfortable nor painful. The
finger was still for just a moment then instead
of withdrawing as I expected he began to move it
in a circle slightly opening the gate a little
bit each time around.
The invading digit seemed to swirl within the
confines of the anal band applying almost
imperceptible pressure to gradually enlarge the
opening. It swirled and swirled and felt so very
good and then it was gone. He slipped the finger
from its warm borders and almost instantly
replaced it with something totally unexpected. I
sensed his face near my bottom then his lips
encircled my asshole and his tongue penetrated
as deep as it could into the dark void. The
feeling, for the few moments it lasted, was
exquisite, but then like the finger it was gone.
I wanted to protest, but the fingers returned
again repeatedly passing slowly over the
opening. On each pass I attempted to lift my
buttocks to capture a digit and force it into my
butt, but on each pass I was denied. By way of
this denial he succeeded in making the point
that he was in charge, and when he was confident
I had learned the lesson he slyly slipped two
fingers into the gap moving them in and out
providing an entirely new sensation.
My asshole was relaxed and easily accepting the
digits when he inserted an equal number from the
other hand. I now had four large fingers moving
randomly in, out, forward, backward, and around
the sphincter. Sublime is a very accurate word
for the feelings I was experiencing. It was not
my most intense sexual experience to date, but
it was wonderful in a unique manner. The feeling
was amazing, but that changed to breathtaking as
he successively slipped one, two, three, and
finally the fourth of his remaining fingers into
my ass. I found it extremely interesting to
monitor the reactions of my body to this mammoth
intrusion. My primary reaction was bliss as
pleasure wave after pleasure wave wafted over my
body.
All this fun was too good to last as he rapidly,
but smoothly removed his fingers. I did not want
them to go, but sensed another step was nearing.
This time the step was focused by an object that
was hard, wide, cylindrical, and long. The end
of his cock bounced on my cheek as the moment of
finality arrived. I was on the cusp of no longer
being an Asshole Virgin, and the cusp was passed
as he slowly pushed his cock inward.
At the orifice opening his cock met with no
resistance because I was already stretched wide
by his fingers, but the hole was rapidly closing
and the passage was not without some opposition.
Inward the cock pressed not allowing the
sphincter to contract until the corona of his
prick was passed. Then, and only then, did my
anal band comfortably tighten on his penile
shaft.
With the head lodged in my rectum the passage of
the shaft was pleasurable and uneventful. I
could feel as millimeter after millimeter slid
through the ring making its way up my rectal
path. It was comforting to know he would not
encounter anything distasteful; there was no
feces remaining in my body. He pressed onward
until the front of his thighs mashed against the
backs of my legs. He pressed onward until no
more of his cock remained unsheathed. He waited.
After an eternity he began to withdraw his
sexual rapier. Slowly, so very slowly he
retracted from his thrust to the depths of my
body. The outward passage presented similar yet
at the same time different sensations. This
motion was much the same as passing a large turd
when it is pleasing to do so. He continued
outward until his entire cock was free. At the
end of his withdrawal he paused before checking
his alignment and again pushing inward. The pace
was notably quicker making the perceived
sensations more intense. A similar awareness
existed as he pulled his cock from my rectum at
an increased pace this time not fully exiting
but rather leaving the head on the inside.
With all the sensations hammering my senses I
mentally kicked myself for not participating in
this pleasurable experience earlier. It was
different than conventional sex. The feelings
were different coming from a different locus,
but they were as pleasurable and intense as any
I had ever known previously. The sensations
mounted as he picked up the pace and force of
both his inward and outer movements.
He must have sensed my growing passion. Maybe it
was the tenseness of my body or maybe it was my
yelling: "Don't stop! Don't stop! Oh, god,
please don't ever stop fucking my ass!"
Regardless of the reason he intensified his
efforts and I responded by attaining orgasm in a
manner I had never known before. That cum was as
intense as any I had ever previously
experienced. A cock moving in and out of my ass
had caused me to cum, and had in that moment
opened for me a new vista of sexuality.
The sensations went a step further as I felt his
cock grow in my ass then erupt shooting shot
after copious shot of his hot juices on to the
interior walls of my ass. As if reinvigorated I
attained orgasm again.
It was pleasant to lay there feeling his cock
soften. As the blood exited the shaft it grew
softer and shorter until at last it slipped from
my body. He didn't, but if he had walked to my
head I would have voraciously sucked and licked
all our combined juices from his now flaccid
penis.
He unlocked my shackles and helped me to stand.
When I attempted to speak he shushed me
indicating I was to say nothing. My clothes were
where I left them and he aided my dressing. As
we paused by the front door he took me in his
arms and passionately kissed my lips before he
said: "Good night. I enjoyed our time very much.
Wait at least three days if after that you
decide you want to do this again then you may
call."
This very gentle and perceptive man had invited
me to do in again if I wanted. There was no
doubt in my mind that in three day's time I
would pick up the telephone and dial his number.
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