A submissive incorporates her Master to introduce anal sex to her girfriend.

You are in the pool, lazily floating. The conversation drifts to last weekend when you and Sue were in the steam room. She mentions seeing the barely visible marks on the underside of your breasts. Hesitating, you fluff it off as a tryst with your lover. She pushes on; you say it is a visible mark of his love and your commitment to him. The conversation drifts around on many subjects, and then she asks you if you have ever had anal intercourse. A warm flush washes over you as you remember all the sensual encounters with a cock up your ass. Your complacent response to yes does not fool her. Questions, like a teenager exploring, hammer you. You try to instill the experience, but know that words won’t convey the way it really is.

Then the words spill forth from her mouth. She has always wondered, but was afraid to try. Her husband was out of the question, and as far as her lover, well, what if he really liked it and she didn’t, then what? Thoughts race through your mind, what if, no, well maybe. You contemplate the thought of asking your master if he would perform the task. Deciding that this needed more serious thought, you let it rest.

Master had summoned you for a whipping, of course you had hinted at the need for it, conjuring up false needs for disciplinary actions for imagined acts of disrespect. Strapped to the cross-ties, ass in the air, the whip lashing your buttocks while you beg for a harder lash, your mind drifts back to the dilemma of your friend. The pain is at a high, the whipping ceased, you feel hands spreading cheeks, then the thrill of a hot cock penetrating deep into your inner core. The thrusting, the urgency, then the tingling of hot cum splashing deep inside you, and then your own release.

Muscles slowly calm from their cramped orgasmic intensifying contractions. With your cheeks still burning from the desired whipping, the orifice tingling from the assault of his cock, you think back to the virgin ass of your friend and the desire to enjoy what you are so lucky to have. After sucking him to another orgasm, you mention the plight of your friend. He asks if he could deflower her virgin ass and then she could choose from there. You say that you will ask her. You are so happy; it has progressed as you wished. Tingles go down your spine thinking of watching the deflowering of a virgin hole. His cock is big, but you know he can be compassionate too, and will make it as painless as possible.

Not wishing to be overzealous, you wait until she contacts you, then in normal conversation you relate that he will oblige her in introducing her to the pleasures of anal intercourse. Calendars are checked for openings on those dates that he is available. Finally a date is picked when all are available. You get second feelings, you have mentioned your bizarre fetishes, but not in detail, will master go the full route with you, how will Sue take this? You decide that master will do what he feels is best and not to worry about it.

The big day arrives and the jitters return. You pick her up and drive to his house where all the props are readily available. Walking inside, you are startled to see him standing there nude. He explains that if he was to bare himself first, it would help ease the tension of the situation. With him already nude, the two of you disrobe comfortably.

He sets your friend down on a chair and while massaging her shoulders and upper arms, explains that anal intercourse can be very sensual, but if not administered properly, very painful. He assures her that he will make it as pleasurable as possible. After much attention and relaxing exercises, he leads her to the table that has been used for a variety of encounters with you. Gently helping her, he positions her in a position of bent over and resting on the table. Her arms are folded and head rests on a pillow that her arms enfold. He asks if she is comfortable which she assures him she is. It is quite a difference from your own experiences on this table. But then again, she is a virgin in that area and with your help will learn of the joy of being penetrated from behind.

Having placed her in position, he commands you to prepare her opening. You hadn’t expected to actually take an active part; you thought you would merely be an observer. With trepidation, you take the jar with the heavy grease, and scooping your finger into it, begin the preparation. Spreading her cheeks, you touch the small wrinkled rosebud. A gasp from her indicates she is aware of what is going on and what will happen next. With the tip of your grease covered finger touching the tightly contracted opening, you apply a slight pressure. Shivers of fear course through her body and the sphincter clamps tighter. Twisting and pushing, you manage to gain a small advance into her anal passage. You stop and rest with barely the tip of your finger penetrating the virgin hole.

Once having gained entrance, all the contractions she can make can not prevent further penetration. You slowly work your way in, reveling in the feel of the soft inner tissue. No wonder master enjoys fondling you this way. You can feel shivers running through her as you massage the orifice. In and out moves your finger, twisting slightly, loosening and lubricating the tight opening. Your mind wanders as you work; you make your finger respond as you like to have a finger move when plunged in your own anus. Withdrawing, you re-coat your finger with the slippery grease, and then ease it into the now receptive hole. Moans are escaping her lips as your finger does its work. Pulling out again, you start in with the middle finger, and then place the tip of the index finger alongside it. Gently pushing, the relaxed orifice accepts both with minimum resistance. Slowly you delve deeper until both are in the full depth. Gently twisting, you work on enlarging the orifice, actually not enlarging it; rather make it comfortable for penetration. As you work your fingers in and out, you feel the tension leave the sphincter muscle, it is becoming relaxed and enjoying the ministrations.

Master also notices the willingness in penetration. He motions you to withdraw and to coat his cock with the lubricant. You scoop out a large amount and begin readying his cock for the task at hand. Starting at the bulging tip, you cover the bulb and start working your way towards the base. As your hand slides along the shaft, it is all you can do to keep from taking the glistening head in your mouth. To aid in staying to the command issued, you minutely examine the skin where your hands are applying the grease. You gather more grease from the jar and starting at the base begins working your way back. Making sure all the skin is covered; you notice that some has gotten in his pubic hair and on the sac holding those lovely balls you like to lick. Figuring too much is better than not enough, you continue. Besides, if he doesn’t approve, he will make you lick it off which you are hoping for, maybe even a stroke or two with his belt. Then you remember, this is a subdued encounter for Sue’s benefit, not yours.

Having thoroughly covered all parts of his cock several times, he motions that it is ready. You clean your hand off and as you await the event, he tells you to climb up on the table straddling her back, and place your hands on her buttocks. It will be your job to spread the buttocks for access, plus additional pulling will open the hole to aid in the penetration. This is better than you hoped for, your head will be over the puckered hole and you will see the deflowering in detail. You rest your buttocks on her back to keep her still, then slipping your fingers in the crack almost all the way down to the anus, you spread her cheeks.

As the throbbing coated head approaches what appears to be a way too small of a hole, you pull harder on the cheeks resulting in the orifice opening slightly. The blunt end of his cock covers the area. Your breathing quickens at the sight, it is way too large to enter such a small orifice. He begins applying pressure, the head is squeezed down trying to enter, and then it will collapse no more. You watch in fascination as the skin stretches around the head. Wrinkles are gone now; color is fading as the tissue stretches. The head is still too big and the surrounding tissue starts folding in as penetration advances. Then there is slippage, the head is entering and moans can be heard from your friend. As the head reaches maximum diameter, you wonder why there is no tearing of the tightly stretched orifice. Then the head pops in and the sphincter relaxes on the smaller diameter between the head and the shaft. A groan of relief is heard from the panting mouth of Sue.

He rests for a moment, gathering his strength as well as allowing your friend to become accustomed to the invasion of the tight hole. He nods to you and once again you stretch the cheeks, giving some relief to the constriction on his cock, though not nearly enough to allow easy penetration. Your eyes are glued to his cock as he pushes in farther. The movement is slow and the sphincter is scraping the grease off the shaft, building up a ring around it. After just a short gain, it comes to a stop again, having reached the internal restriction just past the anus. You shiver thinking about it, this is the most painful part, but once past the restriction, the pain ends quickly. You hear Sue grunting in fear, almost a scream. Master reaches down and places each index finger on the bottom of each of your nipples. Then he places the thumbnail on the top. You have a feeling of what is coming, pain, pain for you, and pain for Sue.

Suddenly his nails dig into your nipples, it is far worse than what you imagined it would be and a scream erupts from your throat. What you don’t see because your vision is blurred from the pain, is that he rammed forward at the same time and penetrated the constricting valve in her rectum. Your senses return in time to hear the trailing off of her combination moan scream. Eyes focus and you can see that his cock has gained further penetration.

Everything has come to a halt, everyone resting for the moment. Now your hands are spreading the cheeks not so much for additional help in the penetration, but so you can watch the completion of the deflowering. With no further resistance other than the stretched sphincter, his cock starts a slow unimpeded entrance. With you holding the cheeks spread, he is able to bury his cock to the hilt. Now you can’t see anything, but can hear the moans of pleasure escaping from her mouth. Then showing the compassion he is capable of and which you love him for, he starts making short strokes in and out, not enough to withdraw the skin of his cock, just movement within his sheath as if her ass was jacking him off. You know what she is feeling, an internal massage like she has never felt before, filling and then emptying the deepest part of her bowel.

As this continues, her moans become louder. He reaches below her with his hand and states that she is wet. This is what you have been waiting for, now the ass fucking begins. He pulls out until only the knob is left in, producing an exclamation of surprise from her lips. You watch in fascination as the cock comes out, the first inch pulls the wall of the bowel with it part way until the friction is lost and the orifice returns to normal allowing the shaft to retreat. Then the opposite occurs as he pushes in, the flesh starts to fold in along with the cock, then gives way and allows entrance.

Now he has established a steady rhythm of thrusts, in and out, the filling and collapsing of the bowel, the slight burning of the friction with the sphincter.

You are getting very aroused watching, your cunt is filled with liquid, throbbing for want of an orgasm. The pace is quickening, the thrusts more powerful, sounds of pleasure coming from both Master’s mouth as well as Sue’s. With a final thrust, he remains buried deep in her ass and you see the contractions of his anal muscles signifying his orgasm.

All motion stops as he rests. You hear moans from Sue and wonder if she reached the peak. As his cock deflates, he pulls gently out of her, and you watch the opening close again to its original state. With her cheeks still spread by your hands, he takes a towel and wipes the excess lubricant from her anus. Heavy breathing indicates that she either hasn’t cum or is ready to again.

He motions you off the table and places you on your knees behind her. Then he tells you to finger her. You tremble, this is your friend, a woman, you have never done this before, yet inquisitiveness of the unknown makes it thrilling. You reach between her legs and slide your fingers along the flesh below the slit. The lips are swollen with lust and your fingers are drawn into her dripping cunt. Now all rationalization of what you are doing is replaced by a desire to make her cum in a manner you would enjoy. Fingers slip in momentarily, then retreat to explore farther up. As you move up, you spread the fingers, pushing the lips apart, and allow them to pass on each side of the sensitive clit. You know that in this highly aroused state, it could be painful to have direct stimulation. Pressing harder you furrow your way past the knob and to the top of the slit. Then releasing, you slowly draw your fingers down over the nub, barely touching the flesh until you reach the opening. Then you push two fingers inside and begin finger fucking her. Just as she is about to cum, you place your thumb below the clit and apply pressure upward triggering the orgasm.

He now gets on the table in your previous position and spreads her cheeks. Motioning to you and her anus, the meaning becomes clear. He wants you to empty her of his cum; tentatively you stick out your tongue and place it on the wrinkled opening only to feel it tighten more from the touch. You look up at him seeking help. He puckers his lips as if to fit over a hole, and makes a sucking sound. You pucker yours, place them around the wrinkled opening and hear her moan. Her sphincter is systematically contracting which feels erotic to you. Taking Masters orders, you apply a vacuum to the orifice.

Everything happens at once. You hear her orgasmic scream, feel the orifice blossom on your lips, and feel a bubble of cum explode in your mouth. The familiar taste of his cum coupled with the bizarre activity triggers a violent orgasm in you. The mood relaxes, but you still have unanswered questions about the pleasures you experienced with another woman, and the nagging thoughts of what if you were with a stranger, and could do anything you wished without the embarrassment of wondering what a friend would say.

He serves light snacks and wine; relaxation sets in as memories fade away. Soon the conversation returns to submission in a subtle way. Sue is inquisitive and Master explains in general terms, but not explicit so as to shock or discourage. Then he suggests that she observe a mild form of submission, an anal copulation of you. She is excited at the prospect of watching instead of being a participant, probably because of the newness and shyness. He crawls up on the table on his hands and knees and tells you to make him hard. Having done this before, you know exactly what he wants you to do. You coat your middle finger with Vaseline, insert it in his ass and feel for the prostate gland. Covering it with the tip of your finger, you start a gentle massaging, and then grasp his limp cock with your other hand. You really wish to put it in your mouth, but you know he wants a slow arousal to maintain the erection. You feel slight stirrings in his cock and the beginnings of firmness in the gland deep in his ass as you softly stroke the shaft of his cock.

You begin to get aroused just knowing you are being permitted to attend to him. His cock is slowly getting harder and the gland is responding as well. He notices Sue looking on with a quizzical expression on her face. Finally she asks what is going on. He explains about the prostate, its function, how it controls the veins in the cock, restricting them, preventing blood to leave the organ which causes an erection. Also that it produces the fluid for the ejaculate, the carrier for the sperm from the testicles, and its contractions cause the orgasm and resulting ejaculation. Disbelief is evident on her face. He tells her that she will be allowed to feel his prostate when he cums, feel the contractions deep inside him. You involuntarily flinch, this is something you have always wanted to experience, but have never been in position to because most of the time you are trussed and passive. Jealousy washes through you, and then you remember that it was your idea to educate your friend.

His cock is hard and ready now. He climbs down off the table and places you in position, laying on it with your hips against the edge, and your legs spread. He is talking to Sue now, explaining that there is little difference between pain and pleasure, and if handled properly, one could augment the other. Hearing those words immediately make you wet, you know that some punishment is coming, but also know it will be mild because of the present company, but you welcome what ever he wishes to give you.

Playing the role, your hands are outstretched gripping the edge of the table. You hear the whoosh of air as the belt descends, then the slap as it makes contact. Perfect, enough to convulse muscles, enough to make the juices flow, enough to make his point and startle the guest, but not nearly as hard as you would like it, however it is stimulating. Again it reigns across your buttocks, but not nearly hard enough. Perhaps the longevity will make it unbearable, make you moan and beg, make you wish fervently to be allowed to cum. But he stops after a few strokes in honor of the guest, and places his hands on your buttocks.

His thumbs slip into your crack, viscously spreading your cheeks, and without warning or preparation, rams into and through your sphincter and buries his cock all the way into your ass. The penetration of the unprepared orifice, the bridging of the internal restriction without tenderness, and the slamming of your hips into the edge of the table top, cause you to cry out. Like a machine, methodically, without passion, he commences to fuck your ass hard. Slamming, ramming, brutally for his enjoyment only, he assaults you.

Then all of a sudden he stops. He tells Sue to put her finger up his ass, instructing her in where the magic gland is, then when she has found it, begins the final thrusts to satisfy himself. Your passion is gone knowing her finger is where you have always wanted yours to be, feeling him cum, helping him cum, extending his orgasm with gentle massages of his innards. It is without any feeling when you feel him squirting inside you; you are nothing but a receptacle.

He gradually goes soft and withdraws from your anus, then tells her to remove her finger from his ass. You sob at hearing him talking to her and avoiding you. A hand slaps you hard bringing you back to the present. He tells you to get on the table in the draining position.

As you squat down on the table, resting on your ankles with your legs spread, hugging your knees, you hear him explaining to her the reason for this procedure. “You were a virgin in this exercise; your bowels repelled the deposit of a foreign substance, your muscles worked to bring the foreign substance into a position at the opening of the orifice so they could be expelled. Marcy however, is very accustomed to being penetrated, having copious amounts of cum deposited in her, and as a result, her unconscious reflexes are satisfied to hold them deep inside without expelling them. Because of that, we have to assist the desire to expel. With her in this position, gravity plays a big part. I can help by causing additional stress to her bowels.”

You try to block out the impersonal discussion, the referring to you as nothing more than a prop for a play. You catch bits and pieces of the conversation, references to arousal, pain, and convulsions. Then you feel his fingers playing along your leg, working their way up to the junction of the spread thighs. Now your senses awaken, he is back attending to you. His finger touches your anus, lingers for a moment, and then drags across the small piece of skin to the bottom of your slit. As you await the touch that will release your orgasm, you hear his command, “Don’t cum”. You feared this, but aren’t surprised. Now instead of letting go and allowing the waves of pleasure to wash over you, you have to concentrate on preventing that which you so desperately want.

The cum is making its way down to your anus, the cramps are starting, the first process to make you expel the intrusion. Your arms tighten on your knees as you clench your teeth, concentrating on the discomfort in your anus rather than the hot electrifying passion in your pussy. You hear him tell Sue that pain will also expedite the process, the involuntary muscle contractions of the body will push the fluid down. His fingers leave your clit and a second later you see the small riding crop swinging up between your legs. The sting as it lands on your exposed flesh causes a scream to erupt from your mouth. The pain is intensified by the passion swollen flesh. Another blow lands, your whole body jerks and the desire to rid yourself of the collecting fluid at your anus is almost too much.

He instructs you to get down off the table and assume the position you were in before when he deposited the troublesome wad inside you. Your bowels are churning as you feel his thumbs spreading your cheeks; you don’t think you can retain it much longer.

What started out to be an enjoyable passionate exercise has turned into a gut wrenching uncomfortable test of control. Through the ripples of cramps demanding your attention, you feel something around the tightly clenched sphincter. You realize it is his lips, puckering as you did to Sue. Then an explosion of events takes place. As he applies a vacuum to the orifice, the pressure inside is uncontrollable, the sphincter opens, the inner bowel folds inward trying to exit pushing the bubble of cum into his mouth. The sensation is like nothing you have ever felt; you fight off an orgasm to enjoy the feeling.

He pulls back from your anus, grabs you by the hair, yanks you head back, and crushing his mouth on yours, transfers the cum into your mouth. You swallow and begin cleaning his mouth with your tongue, licking and poking quickly, waiting for his command to let you cum. Your entire vaginal region is on fire, you are shaking from the need to cum.

He pulls you back from the table, turns you around, lays you back on the table with your legs up, and says, “Give us a demonstration slut, show Sue how you can make yourself cum.” Your hand falls on the riding crop, you turn it around and jam the handle into the dripping dilated hole. Your hand pumps it furiously, fucking the neglected cunt, ramming it deep and releasing the thwarted orgasm.

You have collapsed and your body is like a spineless animal, unable to move. You start to remove the crop, but he pushes it deep inside and tells you to leave it there, you wanted it, so you keep it. He helps you up off the table, and then leads you around the room. Your tired cunt muscles are now required to keep the whip in place, the flexible end is dangling from your hole and slapping against your legs as you walk.

He grabs your head and turns you toward Sue. “Look, we have aroused your friend; it would be rude for us to leave her in that state.” He lays her on the table and holds her legs up in the air, then tells you to lick her. Straining to keep the crop inside you, you bend down and spread her swollen lips. The smell of her sex rises to your nostrils; reluctantly you stick your tongue out to perform the task commanded of you. Fear rolls through your mind, not only the fear of doing this to another woman, but the fear that you might like it.