Penetration

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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 güvenilir canlı bahis siteleri 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 güvenilir illegal bahis siteleri 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 güvenilir bahis şirketleri 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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