The Mentor

I suggest you read the earlier chapters of this story first

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“Oh god,” I thought, “I can’t believe this.  Where is it going to end?”

Here I was, bent over the back of the sofa in Professor Susan Bascom’s hotel suite, naked from the waist down, with Susan’s graduate student Laura standing nearby watching me.  And to my horror, when Susan opened the door to the bedroom of the suite, I couldn’t believe who walked out.

“Yes, Bob, we both decided that you needed a little more training in the appropriate way to treat women, didn’t we, hon?” Susan said to the newcomer.

I just stared at the two of them, unbelieving at what I was seeing.  The incredulity must have shown in my face, because I  heard Susan say, “What’s wrong, Bob?  I thought you’d be happy to see Sarah here.  Don’t you miss her?”

Yes, I missed my wife, but the last thing I wanted was for her to be witnessing this.  All I could think was, “What the hell is she doing here?”

Sarah had a little smile on her face and hadn’t said a word yet, but continued to stand next to Susan who had an even bigger shit-eating grin on her face.

I finally managed to mumble, “Sarah, what are you doing here?”

Before she could say anything, Susan answered for her.  “Well, Bob, after our little encounter in the women’s room the other night, I decided that you really did need more training than I had provided to you.  What you need is what we call in the academic world, better ‘mentoring’ – somebody who can help you learn appropriate mores and etiquette, the right way to act around your superiors, especially women.”

She turned to Laura and asked, “You understand these things, don’t you, pet?  You know the right way to act around me because I’ve been a good mentor to you, haven’t I?”

Laura quickly answered, “Oh yes, Professor Bascom, you’ve mentored me very well.”

“Good, pet, and I’ve figured out that it is exactly that kind of training that Professor Arnold here needs, right Bob?”

I stared over at her and Sarah, still not believing my wife was standing there as a party to this encounter.

“I said, right Bob?” Susan said to me in a slightly louder voice.

“Yes, Su – I mean, yes Professor Bascom,” I replied.  As I said this, I saw Sarah cock an eyebrow for a second.  I’m sure the shock of her seeing me almost naked like this on the couch was one thing, but hearing my verbal subservience to Susan was another.

“That’s right, Bob, and Sarah is going to help me to train you.”  With that she grabbed Sarah’s hand and the two of them walked over to me.  I looked back over my shoulder at Sarah.  She was wearing a pair of gray slacks and a plum-colored silk blouse.  She too was somewhat plump, not unlike Susan, and her blouse nicely showed off her ample breasts.

As they stood next to me, I began to rise up from the couch, but before I got too far, I heard Susan say, “No, Bob, you can stay right where you are.”

But this time I chose to ignore her.  I had had enough, with Sarah here in the room I knew I had to bring the whole thing to a halt.  “No, Susan – I am getting up, I need to talk to Sarah.”

As I continued to rise up, I felt a hand on the back of my head, pushing me back down.  I was about to swat Susan’s hand away, but as I glanced that way, I saw it was not Susan’s hand that was pushing me down, but Sarah’s.  Surprised and confused, I allowed her to push me back down so that my head was again resting on the back of the couch.  “What’s going on, Sarah?” I asked her.

“I’m sorry, Bob, but I agree with Susan.  I want you to stay there and listen to me,” she said.  I didn’t say anything, signaling my acquiescence.

Sarah continued, “When Susan called me the other evening, and explained to me what had happened, at first I didn’t believe her.  She told me everything, from how you followed her and Laura into the bathroom, to what happened when she discovered you there, to what she did to you.”

As Sarah started to describe her conversation with Susan, I became a bit wary.  Sarah and I had a very active sex life, and we had engaged in numerous types of roleplaying, including some dominance and submission play.  And we had been on again and off again swingers, so we certainly weren’t prudes in any way.  But never had we – or I – done anything like what had happened to me in that women’s restroom in the hotel two nights ago.  So I was not quite sure how she was going to react to what she had heard about.  I was also surprised at what was turning out to be a level of familiarity between Susan and Sarah that I hadn’t known had existed.  I knew they had occasionally e-mailed with each other, and had met a couple of times when Sarah accompanied me to conferences, but didn’t think it went beyond that.

“Because I didn’t believe her,” Sarah continued, “Susan offered to e-mail me one of the pictures, and I took her up on her offer.  Needless to say, when I received it I was shocked to see that she was telling the truth.  I just didn’t want to believe you’d do something so risky, Bob.  So when I called Susan back after I got her e-mail, we had a long chat about how we should proceed.  She suggested that I fly out and join her here, and that the two of us could deal with it together.  So I did, and here I am.” 

With that she, gave me a little smile, and I knew that I was sunk.  Any thought that she would help me to talk sense into Susan’s head went right out of my mind as I realized that she was apparently in this just as much as Susan was.  I now had to deal not just with Susan’s wrath, and what she had planned for me, but now also had to worry about Sarah’s participation.

Now it was Susan’s turn to chime in again.  “Very well explained, Sarah.  So you see, Bob, that’s why your dear wife is here with us right now, so she can help me mentor you in the appropriate way to behave around women.  So are you ready to begin?”

I sighed, and simply answered, “Yes, if we must.”

Susan glared at me once again, showing her disapproval.  I immediately knew what she wanted, and quickly replied, “Yes, ma’am, I am ready to begin.”

Susan smiled once again, and said to Sarah, “See, dear, it really is quite easy once you have them trained a bit.  Now, let’s see, how do we want to start?”  She hesitated for a few seconds, and I just lay there over the back of the couch, fretting over exactly what she was going to do.

After a few moments, Susan said, “Laura, pet, come over here please.”

I turned my head the other way to look over at Laura as she came back toward me.  Susan saw me look, however, and as Laura came nearby, she said to her, “Do me a favor, pet.  Get my scarf from the bedroom.”

“Yes, ma’am,” Laura replied, and I saw her walk into the other room.

A few seconds later, I heard Laura pad quietly across the carpet to a spot behind me.  Susan said to her, “Okay, pet, now tie it around Bob’s head – we don’t want him getting distracted by watching everything.”

I felt Laura kneel on the couch, and then felt the cool silk over my eyes as she tied the scarf tightly around my head.  I was now enveloped in darkness, which only helped to heighten all my other senses.

“Okay, now we’ll get started.  So here’s what we’re going to do Bob.  To start your training in the appropriate way to appreciate women, we’re going to spank you.  And your job is to tell us which of the three of us is administering the punishment to you.  If you get it right, you’ll be rewarded; wrong, and you’ll be further punished.  Do you understand?”

I was so humiliated, thinking about what was about to happen, and especially by the idea of both my wife and Susan’s young grad student witnessing and participating.  But I knew I was sunk, and had no choice but to play along.  “Yes, ma’am, I understand,” I replied.

“It’s not just ‘ma’am,’ Bob – you have three women here who you need to be attentive to,” Susan scolded me.

I was stumped for few moments, not quite sure how to respond to this.  As I sat there, kneeling on the couch, naked from the waist down, trying to figure it out, I quickly felt a sharp slap on my left cheek.

“Ow,” I shouted in response, without thinking.

“What was that?” I heard Susan’s voice say.

I quickly replied, “I’m sorry, mistresses.”

“That’s better, Bob.  Now tell me – which one of us was it that just laid that blow upon your scrawny little ass?”

I thought for just a second, and realized the speed with which I was hit must have meant that it was Susan who inflicted the punishment.  There was not enough time for her to have signaled Sarah or Laura to hit me.  “It was you, Professor Bascom,” I answered.

“Oh, very good Bob – you’re doing just fine so far!” And with that, she lightly rubbed my ass, right over what was by now no doubt a very red spot on my cheek.  “Okay, ladies,” she continued, “why don’t the two of you come over here right next to me.  Remember to address us appropriately, Bob, and I don’t want to hear any whining or complaining.”

I continued kneeling there as I heard the rustling of people moving around behind me, and after a few seconds, Susan said, “Get ready, Bob, here’s the next one.”

I tensed up, awaiting the next blow to rain down on my ass.  It seemed like minutes of anticipation, but I knew it must have only been a few seconds – and then it hit me, a hard smack upon the other cheek from the first.  It took everything in my being to resist crying out in pain, but somehow I managed.  I thought for a second, trying to figure out which of the three women hit me.  I knew Susan was playing mind games with me, and I was trying to outguess her.  I quickly decided she would have had one of the other two land that second blow, and it seemed too hard for it to have been Laura.  I suspected she would be a little timid at first, and there was nothing shy about the hand that had just hit me.

“That was Mistress Sarah,” I said.

“Bravo, Bob – I’m very impressed.  You’re two for two.”

I sighed silently, hoping that my stellar performance would bring an end to it.  After all, Susan had said I’d be rewarded if I guessed right.  But before I could be too proud of myself, another shot landed on the same ass cheek.  This one did, in fact, feel lighter than the others, so I quickly said with great confidence, “That would be Laur - er, Mistress Laura.”

“Oh, I’m sorry, Bob, but you’re wrong,” Susan replied.  “That was my hand again, you’re perfect streak is broken.  And you know what that means.”

I steeled myself, ready for more punishment, but after waiting a few seconds, nothing came.

“I said, you know what that means, don’t you Bob?”

I quickly replied in defeat, “Yes, Mistress Susan, it means I will be punished more.”

“That’s right, my little worm.” And with that, she – or somebody – quickly hit me four more times, twice on each cheek in succession, and there was nothing light about these blows.  Again, I had to bite my lip to prevent myself from crying out in pain, but I somehow managed.  “That was you, Mistress Susan,” I mumbled under my breath.

“What was that, Bob, I can’t hear you?”

Having caught my breath, I spoke up.  “That was you, Mistress Susan.”

“Ah yes, you are definitely learning the feel of my hand upon your ass, you are doing much better now, my pet.  I think we’re going to stop here for a moment since you’re doing so well.”

I sighed again, happy to have a respite – no matter how brief – from the attacks that I knew must have turned my ass cheeks bright red.  I began to sit back on my ankles, but somebody tapped me lightly and I heard Sarah this time say, “No Bob, we’re not done with you yet.”

I was surprised to hear Sarah saying this, as I still saw her as more of a passive participant in this whole scene, following along with Susan’s lead.  But she clearly was playing a more assertive role than I had thought she would.  I pulled myself back up to a kneeling position, once again with my head and chest resting on the back of the sofa.

“I’ll be right back, ladies,” Susan said, and I heard her pad off away from the sofa.  I realized she must have gone into her bedroom, because I didn’t hear the sound of her shoes on the tile of the bathroom floor.  A minute or so later, I heard her footsteps approach again.  As she came closer, I heard my wife giggle, a sound that sent my mind spinning with questions about what Susan had in mind.

For about a minute nothing happened – no sound of walking, nor any other sound that would clue me in to what was coming next.  I was thankful that the spankings had stopped, at least for now.  But I was still nervously anticipating Susan’s – and I knew it would be Susan, because she was clearly in charge – next move.

I felt somebody’s hands on the inside of my knees perched on the sofa, gently easing them outward, causing me to spread my legs even further than they already were.  Even without any words being spoken, it was clear what the intent was.

And then I felt it – a cold, damp sensation at the top of the crack of my ass.  I wasn’t sure what it was, and strangely, my first thought was that there was some kind of leak from the ceiling.  But then I felt the sensation of something very viscous slowly dripping down the crack toward my rosebud.  And then I felt more large, cold drops of the same liquid dropped right upon the first spot, and they too dripped down my rosebud, past it, and down my ball sack where it felt like it was pooling in the hair there.

It was then that I realized it must have been some sort of lube that Susan had gotten from her bedroom, and she was now dripping it down my ass.  I was so embarrassed, thinking about what I must have looked like – my legs spread wide on the couch, my ass up in the air, lewdly exposed to the three women.  And now, some kind of lube dripping down my crack toward my balls.  I ground my head even further into the back of the sofa, wishing I could just disappear into it, never to be seen again.

Just as I thought I was going to die from shame, I heard the sound of somebody sucking in their breath, as if to try to catch it after seeing something unexpected.  I wasn’t sure which of the three women it was, but then I heard Susan say, “Yes, my dear, that’s quite a sight, isn’t it?  Professor Arnold crouched there, with his nether regions so beautifully exposed to us, so open to us to do anything we wish, aren’t they?”

Much to my surprise, it was Laura’s voice I heard next.  “Yes, ma’am, it is quite a sight.”  I was surprised that Laura was the one who had reacted as she did.  I realized that she must have never been in this position with Susan before, Susan dominating somebody – especially a man – the way that she was doing to me.  I wasn’t sure whether Laura’s reaction was one of shock, disgust, or arousal, however; her voice did not betray what she was thinking.

“Come here, my pet, come closer,” Susan said, most likely to Laura.  “I want you to experience this for yourself.”  I heard Laura walk quietly from the side of me, where she had been, to position herself behind me, next to where I had been hearing Susan’s voice coming from.

I felt a hand on the back of my head, lightly tracing fingers down the back of my neck, then my back, and down right to the spot just above where Susan had dropped the lube.  “I want you to just relax, Bob,” Susan said in a soft voice.  “You are here for our pleasure, and you know that there is nothing you can do about it, don’t you.”  I lightly nodded my head, resigned once again to my fate.

“I want to hear your voice, Bob, I want to hear the confirmation that you submit to our dominance,” she said in the same quiet tone.

“Yes, Professor Bascom, I understand that I have no choice but to submit to your wishes.”

“And the others, too, Bob?”

I sighed and confirmed, “Yes, Mistress Laura and Mistress Sarah also.”

“Good, then we will continue.  Come here, Laura.  Take your finger, and run it up and down Bob’s well-lubricated ass.”

I gasped uncontrollably at the realization of what Susan was now doing.  Somehow, hearing her give the instruction out loud to her graduate student, made the entire episode that much more humiliating to me.  The thought that this student, who two days ago probably held me in some esteem based on my professional standing, was now standing behind me as I was crouched naked and lewdly displayed to her, ready to submit to whatever she chose to do to me, was just too much to bear.  I began quietly sobbing at my predicament.

Susan must have heard this, as did Sarah.  I felt a hand stroking my hair over the blindfold, and heard Sarah’s voice whispering in my ear, “That’s okay my love, just relax.  You need this; you need to be taught the proper way to respect women.  I promise you, no harm will come to you – I’ve gotten Susan to agree to that.  But you must endure your training.”

I did my best to fight back the tears, and lightly nodded my head in agreement.  All I could do was just hope that they would get this “training” over with as quickly as possible, and then Sarah and I could go on with our lives – hopefully never to talk about this horrendous experience again.

“Okay, Bob, are you ready to continue now?” Susan asked. 

I sniffled back the tears and replied, “Yes, Professor Bascom.”

I then felt a finger, Laura’s presumably, doing as Susan had instructed.  She ran it up and down my crack, and it moved very effortlessly because of the liberal dose of lubrication that had been poured down it.

After a minute or two of this, Susan said, “You know what to do next, don’t you my pet?”

“Yes, ma’am,” Laura replied, and then I felt it – a prodding finger upon my asshole, pressing lightly at first, then more strongly.  She was clearly trying to be gentle, but yet at the same time was tactically insistent on what she was going to accomplish.  Sarah and I had engaged in anal play many times, so the sensations were not totally foreign to me.  The setting, however, was, and it was hard to endure what was happening, but I did my best to steel myself for it.

Laura continued rotating her finger around, slowly easing it into my asshole, until the point where I realized she must have been in up to about her first knuckle.  Luckily, she was fairly slim built, and her fingers mirrored her body size, so it really was not very painful at all.  It was more the humiliation that was getting to me, knowing that this student was fingering me in the ass – and my wife and professional colleague were watching her do it.

And then, before I knew what was happening, the realization hit me that my body was responding to what she was doing.  I felt my cock stiffening as she slowly rotated her finger around, and then began pistoning it in and out of my ass.  No doubt, Sarah was not surprised; she knew about my submissive nature, and she knew how turned on I could get when she would dominate me anally.  But I was surprised at my body’s reaction in the face of being watched by these two other women.  But somehow my mind must have migrated into that subspace that it reaches when I am being dominated, because I was definitely getting aroused, and I knew my erection would betray me.

And right on cue, I heard a clap, and Susan’s voice exclaim with glee, “Oh I just knew it – I just knew he was such a little subbie boy who loved having things stuck up his ass.  Look at his funny little penis.”  All three women giggled at Susan’s exclamation of surprise and excitement as Laura continued working her finger in and out of my ass.

She was right, and I don’t know if she figured it out on her own, or if she had been clued in by Sarah.  I was greatly turned on by having my ass played with, especially as part of dominance and submission.  It was an involuntary response, even in the face of the situation in which I found myself.

I felt fingers close around my now fully-erect cock, and felt the hand stroke lightly up and down the shaft.  I was not sure whose fingers they were, but then I heard Susan say, “Yup, no doubt about it – he likes this!” and I realized it was she who was working my cock.  I had to admit it felt good; the combined sensation of Laura’s finger in my ass, and Susan’s around my cock, was quite a turn on.

Susan released my cock, and then I felt fingers – presumably hers – joining Laura’s on my ass.  The fingers wiped up and down my crack a few times, and then before I knew what was happening, they closed again around my cock, this time stroking it even more fluidly than before because of the lubrication.

They both continued for a few minutes, Laura pushing her finger even further into my ass. I was afraid that they would make me cum like this as the arousal was building in my body.  My breathing became heavier as I was hunched over the back of the couch, but then I felt Susan’s fingers release from my cock and I felt a hard smack across my right ass cheek.  I yelped an involuntary “Ow!”

Susan said, “Tsk, tsk, Bob – know cumming for you, my pet.  You should know that you can only cum when we women give you permission.”

I resisted the temptation to put my hand back on my sore ass to rub it, and simply replied in a defeated voice, “Yes, Mistress Susan.”

“That’s right, and don’t you forget it,” she replied.  “Okay, Laura, you can stop that.”  And with that command, I felt her finger removed immediately from my asshole.  It felt very open and empty, much more so than it had ten minutes ago.

“But we’re not done with your training yet, are we ladies?” Susan inquired of the other two.  I couldn’t see how they reacted, as they did not say anything, but I presumed they nodded in acquiescence.  “Yes, we have much more to do.”

I once again heard and felt Susan step away from behind me, and it sounded like she was walking around in the living room of her hotel suite.  I then heard one of the other two women walk away, and then heard the sound of shoes tapping in the bathroom, and the sound of water running.  I assumed that was Laura washing her hand after she had been working my asshole so vigorously.

I heard both pairs of feet on the carpet as they approached me again.  There was no movement for a minute,  and then without warning, I sensed a flash through my blindfold.  This was quickly followed by two more, and I realized that somebody was taking pictures of me, prostrate over the back of the couch, all spread open for the world to see.  Just more evidence that I assumed Susan would be able to use against me in the future.

Much to my surprise, though, it was Sarah’s voice that I heard next.  “Now that will certainly make a pretty picture for us, don’t you think my dear?” she asked.  “Where do you think we should hang one of those – in our bedroom, where only you and I would get to see it?”

I mumbled to her, “Whatever,” which was followed by another, albeit lighter, slap upon my ass.  “Is that the proper way to address me, Bob?” she said.

“No, Mistress Sarah, I’m sorry.  I would rather you not put that picture anywhere, to be honest.”

She laughed, and said, “Don’t worry, I was just joking.  But it’s nice to know that I have it if I ever decide I do want to use it.  Or perhaps even share it with my friends here, right ladies?  It will make such a nice complement to the pictures that Susan took the other night in the bathroom.”

The three of them laughed about that, and then I heard somebody walk away again.  I heard something being put down on the glass-topped table, and I hoped it was the camera.

Sarah walked back toward me, and I heard her say, “What about this, Professor Bascom?  This could be fun?”

Susan replied enthusiastically, “Oh yes, it definitely could!”

I had no idea what they were talking about, but then I sensed somebody leaning over me.  I felt fingers on the blindfold, and it was pulled down below my eyes, but not off my head.  I blinked a few times as the bright light of the room assaulted my eyes.  As they adjusted, I realized there was something right next to my head.  I turned my head that way to get a better look, and my jaw dropped open when I realized what was there.

“That’s right, Bob,” Sarah said.  “Think it’s time for the next step of your training.”