A Submissive's Journey Pt. 05

This was the sort of thing that kept running through my mind in every class that I took that morning, that and the knowledge that there was at least one person out there that knew what I was getting into, the mysterious man that was going to meet me with the odd phrase 'sissy gurl'.

Those words brought up images that I did not like to assign to myself, usually some very masculine looking guy in too much makeup wearing a big gaudy frilly dress and sometimes even a diaper. How was that sexy? I got the idea that it was humiliating for him and therefore a way for other guys to get off on being dominant. That was the idea I guess that I would respond to those words that they chose in a submissive manner and would be put into my role. The game so far had been kind of fun, even if I wasn't ready to accept it myself yet, so why not.

All morning I had been looking around for whom the prospective mystery man was. It was like playing a spy game. There was very little chance that it was a fellow student so I ruled them out quickly. More than likely it was someone that wasn't even associated with the college at all and the man would approach me between classes or on my lunch break.

Regardless of my deductions, I still eyed most every male that I met with a sort of curiosity. At first I would kind of look to see if they were paying attention to me and thus be a possible suspect, which I had started calling in my mind the 'new boss'. And then with some of the guys, especially if they were quite a bit larger than me, I would take a surreptitious second look to see if I would want to kneel. There was a certain art to not looking but using the corners of my eyes to inspect packages.

The whole thing had me feeling quite slutty I must say and probably with good reason, for who but a slut would go around all morning checking out men's packages. I forgave myself in the fact that I was also playing this little game of spotting my new companion who could hardly be classed less of a sex fiend than myself for preying on a new young college student for his sensual needs.

It occurred to me that this 'new boss' might not have any idea what my schedule was and I was playing this stupid game and getting all worked up for nothing; that he would simply show himself to me as I was walking back to my dorm where he was sure to know I would end up.

The day wore on, past lunch where I was almost certain that he would appear and onto my afternoon literature class, my last class of the day. It happened to be my favorite class for reading was one of the great joys of my life. To a boy like myself who wasn't very social, the characters in books were like constant companions that couldn't judge you or have any expectations, much like I imagined some people felt for their cats.

There had been a small assignment that I had missed on Tuesday when I was playing hooky so at the end of class I went up to the podium to ask the professor if could have a copy. Several students surrounded him and I waited patiently as was my nature, avoiding any conflict by having to maneuver in line.

Finally, the professor was alone and I asked him for my assignment. He seemed lost in his thoughts, perhaps troubled by something a student had just said. At any rate he didn't seem to be paying a lot of attention to me. I asked him again if I could have a moment of his time for I had missed the previous assignment.

He glanced up at me over the top of his reading glasses then slowly looked around the whole room, which by this time was almost deserted wondered for a second and then turned back to me.

"Your attendance has been good young John so I wont berate you. However, you must stay on top of your schoolwork. If you let it slip too much you will fall behind, a most awful thing to do in your freshman year. Remember this is the year that most students drop out. So persevere and you will be sure to succeed." The elderly gentleman sifted through his paperwork as he spoke.

I hadn't really wanted a lecture, just the stupid homework so I could get away from classes and back into my little world. The man was sure to meet me on my way home or there might be a message on my answering machine.

Professor Mason found the paper he sought and held it in his hand as he looked again slowly around the room.

Mystified as to why he would be doing that I followed his gaze. We were alone now in the room.

"Here is your paper young John. Please return it next Tuesday for credit," He said holding out he paper, which I snatched lightly and turned to go.

"Oh, John one last thing," Said the professor, "I must say I feel rather odd asking you this, but I didn't exactly pick the words myself. What would you say if I called you a sissy girl?"

My jaw dropped. I hadn't even thought about Professor Mason when playing my little spy game. Maybe it was that he was older than I would have expected someone to be to be in a group like that o Mr. Silver's. I hadn't even looked at him in my naughty little game of would I suck him. For some reason I thought older people were just non-sexual.

He stood there waiting for my response. Maybe he was afraid that his friends had played a joke on him or that he had the wrong person. More than likely I could just say something offhand and leave, blowing the whole thing off, but the whole day had been spent building up to this moment so I just said meekly.

"I was supposed to hear that today. I am sorry I didn't know it would be you, umm, Sir."

My head bowed a bit and my posture took on a more passive form. I wasn't sure that I really wanted to have anything to do with this man sexually. I mean he was old, probably about sixty. The one guy in the booth yesterday I had thought was old, but this was going a bit too far.

"That's good John. Be a dear and lock that door for me. Yours is my last class of the day. That's right make sure the shades are drawn tight too."

I walked slowly over to the door. The whole thing felt kind of surreal. I had been prepared all day, but this had totally caught me off guard. A sudden urge to run came over me, which I almost succumbed to, but in the end I just turned the latch, locking myself in and sealing my fate for the next couple hours.

"That will do young man. Now come here. Next to me."

The professor was standing behind the chair of a large oak desk, which was covered with papers except on the right-hand side where he had evidently cleared a space for me. I walked over, standing in front of this area.

I placed my hands at my sides and then clasped them in front of me not sure exactly what to do. My confusion was short lived. He grabbed my right forearm and placed my hand palm down on the desk then repeated with the left.

Reaching around my waist from behind he unfastened my belt, unbuttoned my pants and ran the zipper down. A hand crept in and started massaging my groin.

It was the first time that I had actually had someone play with my penis. In all of my previous encounters I had been the one pleasing the other man. It was confusing for me to be the one accepting the pleasure right now.

"Excuse me, Sir," I stammered, "but I thought I was... I mean... I was the one to please you."

"Shush, boy." he said gently, "You are to do as you are told. I am taking it on myself to teach you a special lesson today. Be silent and let me have my way with you and you will be richer for it. I promise."

My penis was now fully erect and Mr. Mason stroked it slowly, sometimes stopping to squeeze my balls or the head of my cock gently, sending shivers up my spine. At times he would go lower than my scrotum and even farther back almost to my anus and press up, making little circles almost like girls I saw in videos frigging themselves off.

When he did this my member would pop up slightly as if stimulated, but I wouldn't really feel much. It also had the effect of making me notice the entrance to my rear more. He wasn't actually touching it but something in there was moving around and activating the nerves in the area.

He alternated between massaging that spot and stroking my cock for about five minutes. For some reason this simple act had me feeling more of a lack of control than anything except Rikki fucking me the other night. When I was sucking, even when I was getting face fucked to a degree I had some sort of way of changing what was happening, but with the hand coming from behind me I had no idea what was going to happen next. All I could do was just stand there.

Prof. Mason pulled back and grabbing my pants and underwear pulled them down, ordering me to step out of them. At that point all that I had left on was my socks and my polo style shirt.

He turned away from me for a bit and was messing around in some sort of cabinet. Then I heard that familiar popping sound. Even now if I am in some normal circumstance out in the world and someone flips open the plastic lid on a bottle of something and it sounds just right, my cock will jump in my pants in anticipation.

When I heard the sound this time I instinctively arched my back a bit and pushed my ass out. He had decided on a better position for me, however, and proceeded to pull each leg about one foot backwards and spread them about another foot. My hands were moved to outside of my shoulders on the edge of the desk, which, in turn, forced my head down to a few inches above the desk. The professor balled up my pants and stuck them under my face as a cushion, on which he rested my chin.

All of this had the effect of creating the maximum exposure for my anal entry. My legs being spread so far apart forced my cheeks open. At any second I expected to feel something moist and slippery going up inside of me.

The seconds ticked by: five, ten, twenty. Around me was complete silence. The position wasn't the most comfortable. I could maintain it. But the lack of any sound or any sensory input whatsoever when it was so expected was unnerving.

My legs had tensed and I had raised my ass in expectation, but now that I was going to be waiting a while I forced myself to relax. I steadied my breathing, and closed my eyes. Stifling the urgent desire to ask what was going on.

There was a sense that if I asked something severe would happen. There was something about the manner of this timid old professor that was in a way more threatening than the blowhard rocker from the night before.

Now a minute had passed or maybe more.

A cool moist finger ran around the edge of my hole. The coolness shocked me and I tensed up, gasping.

The finger retreated, more seconds passed.

Next was a gentle squeeze of my testicles. Again my gluteus muscles clenched up, I gripped the edge of the desk momentarily, letting out an "ooh", then release.

Then with the fingers of either hand he reached silently up behind my and delicately pinched my nipples. I had never even thought about that area in a sexual way before, on girls yeah, but for me it was kind almost off limits. If he had been rough it may have been different but his touch was so light to such a sensitive area that my hips squirmed.

Again the stillness filled the room.

Hard and firm came the slap on my ass cheek. It was his bare palm I could tell. The sound was tight, ringing clear throughout the room and reverberating off the walls the echo came back as the sound of chopping wood.

Now the waiting was over for he started in on a rhythm, slapping one cheek and then the other lightly, but hard enough I am sure that my cheeks were turning red. There was no pain associated with this, but I had a very definite sense inside of myself that he was taking his right. The smacks were a favor to me for being a good boy for if I were bad they might not be so easy.

Who knows what a person that may have been passing in the hall would have thought hearing the steady cannonade of whacking sounds. Even if they could guess there was no way that they convince themselves they were right.

Just when I started to get tender on my backside he relented and the waiting game was back on again.

This time for over a minute pure silence fell over the room. I could hear my heart beating heavily in my chest awaiting the anal assault that was sure to come.

The start was very gentle and much longer than I would have thought. Both of my previous encounters had been very much a wham bam thank you sort of thing, but Mr. Mason enjoyed taking his time.

First, he started in with something that was too solid to be his penis, maybe the thickness of a finger. It was cool and slick as he gradually inserted it up my in my nether region. He would take it in a bit hold it, gently wriggle it around inside of me and then pull it out. He seems to be concentrating very much on the act of insertion.

Next, he got something that was larger as it certainly stretched me more when he pushed it past the threshold. Slowly wider and wider it forced the opening as he got more depth. So stretched was I that I tensed for the pain, which in turn brought on a cycle of more pain and more clenching that seemed involuntary. A wave of anguish shot up my spine.

He pulled the love tool out to the tip waited a second and pushed it back in a measured manner, the lubrication allowing my sphincter to stretch and accept the foreign object into my loins.

This practice, for that was really what it was, of stretching me out and then me panicking and forcing the object out followed by the gentle insistence of another forward thrust, got me mentally used to the action of being penetrated while relaxing the hole itself for further use.

In time this tool was removed as well and replaced again. At first I thought it was the original thinner version, but this was much longer and had a sort of curve for when he pushed it in it did not go straight back, but instead seemed to press forward on the base of my penis in about the same place he was massaging me at the beginning of our session.

This caused a feeling quite unlike any that I had ever had before. The closest I could explain was that of a girl getting fucked and you hit her g-spot, because when it was inserted just right a strong jolt of lust coursed through me.

As with the nipple sensation this was one that I could tell would be very easy to overdo. I was just too sensitive. I think that I had felt something like this more so when Mr. Silver fucked me than Rikki, but the stimulation with this tool was far more direct.

The professor I think sensed that my edge was being reached with this tool. He held it in and, putting his hand around the shaft of my penis, stroked me. It was like he was milking me. I could feel the wetness at the tip of my cock.

He stroked me for a short time and then still holding my penis brought his other finger up around my face to my lips, rubbing the juice that he had collected there. I licked instinctively, letting out a "mmm" sound.

The milking continued for several minutes. There was a few times when I felt that I was going to just explode right here and shoot all over he floor, but Mr. Mason would stop and feed me what he had collected.

The hand and sex toy were removed and I was left hanging again in anticipation. Surely now he would fuck me.

The bottle cap sounded off again and a light smile came across my face.

He started gently in on me, which may not have been all that necessary for my entrance at least was quite ready for him. I could feel him pass the zone that had caused me the most pain and anxiety and then I was being stretched anew around his glorious manhood.

There was no way for me to know just how long his penis was so when he started the fucking motion I thought that he was either rather small or the time he spent warming me up really had worked well. I could feel him rocking up in me but there wasn't the more extreme feeling of deeper exploration.

It turned out that he was just taking his time, with short strokes to start and at a low pace. He proceeded to push slightly further in unremarkable increments, keeping with his method of easy introductions to my anal passage.

But, as experienced and careful as the professor was, he was still a man. The tightness of my young ass constricting on his love tool and the decadent horniness of having a new young toy to explore sexually came over him and he began to thrust in me full strokes that stirred up the passions within me and took me away to a different plane of existence.

His belly smacked against my ass over and over as he plunged up inside of me. I rode each thrust forming myself around him. His hand reached down once more and stimulated the head of my penis rubbing on the underside causing the length of my cock to jump around wildly.

Little strokes on the shaft and then back to the head, all the while pounding his stiff rod up inside of me like some sort of machine. It seemed he would never cum.

I started moaning with every thrust like a young girl being deflowered, my voice somehow soft and high, as if his strokes had taken my very manhood itself.

Then his hands left my crotch and were placed firmly on my hips. He pressed down on me so that know I was almost squatting, while my hips were still set high. My back was arched so and he took to fucking straight down into me.

The head of his penis started to hit the same spot that he had been working with the love toy. Moans of ecstasy overcame me and from deep inside of me my cock pulsed hard three times, squirting my cum all over the drawers of the professor's desk.

Sensing my rapture he sped up and finished as well, filling my hole with a slippery wetness.

Spent, he rested on my back, keeping me impaled upon him and breathing heavily.

"Good boy," he whispered between breaths, "Now get down and lick up your mess."

So wrapped up in what had just happened to me I obeyed without thought. His gentle push on my back too my to my knees where I proceeded to lick the cabinet doors cleaning my cum off. The juice was now good and familiar, but I still felt dirty tasting my own in front of anyone, even a man who had just thoroughly fucked my ass.

He sat on the desk up above me where I had been resting my chin and looked down in satisfaction.

When I was finished I looked up at him. Inside of me I wanted to know if I had done. There was a pleading, longing look in my eyes. Above me his now soft cock and balls hung over the edge of the desk. Above his face smiled down at me gently.

Never again would I look at an older man and discard them sexually for his man had just opened me up. I knew that I would willingly serve him just to know that I was doing a good job and pleasing him.

As he seemed content I did what I now realize I wanted to do all along. I had missed the feel of a living cock in my mouth. Even though I had just been fed the day before by several men, deep inside me the seed of yearning for the taste of cock had been planted and was now spreading. I moved up between his legs, eyes on my prize and ever so gently started to lick on his balls and shaft.

There was a foreign taste that I assumed to be lube and another that I could tell was from me, which although I got no pleasure from it, it didn't bother me enough to worry much. There was also the cummy taste, but soon all would be washed away with the licks of my tongue.

Before long he reached a state of semi-hardness again, but he never came. I just knelt there gently sucking on his sweet cock for a long time, until he placed his hand on my head and told me it was time to go.

He gave me the toy that he was using to stretch me and some lube telling me that I should be gentle with it, but to use it once in a while to stretch my butt out and to work myself with it for about a good half hour before I showed up at the party on Saturday night. Otherwise I was to rest my ass until then and accept no more fucking, because I was going to be worked over Saturday night in my initiation.