My Trainer, Bobby - Part 2

"Do you want me to ask you to do more?"

"Yes." I said softly

"Will you do anything I ask?"

"Yes," I said in the same voice.

"Good.  Then we have only started."

Bobby reached into his pack and brought out a bag.  He handed it to me.  I opened the bag and looked in.  At first, I didn't get it.  But as I pulled the various pieces out, I figured out one - it was a bottle of lube of some sort.  I figured it was for jacking off.  I had read about it and heard about it, but had never used any.  It made me blush again, remembering what I had just done in front of Bobby.  

To jack off and show him doing my most intimate thing was so beyond me.  But it hit a chord in me and made me hard and shook me to the core of my being.  I had fantasies of being naked in front of someone, but to actually do it was so out there.

Also in the pack were a dog collar and a weird shaped plastic piece.  I mean it looked like a plug of some kind, but had no clue.  

"Put the collar on.  It is to remind you that you are mine, to do with as I wish.  I will determine when you have to wear it."  My hand shook as I reached up and put it around my neck.  My cock throbbed as I put the end through the buckle and cinched it tight.  

"So what are going to do with that?" Bobby asked me looking at the plastic.  

"I don't know." I said honestly.  

"It goes in your body."  It clicked and I blushed, he meant for me to put it up my ass!  "Have you ever had anything up your ass?"  

My face reddened so much I could feel a flush on my face.  "No," I said, completely aghast by the suggestion.  

"Not even your finger?" He asked incredulously.

"No!"  I said again, still not imagining this.  

"Well, you will now.  Take some of the lube and put in your fingers and then insert your finger up your ass."  He said it so simply, like this is what everyone does.  "Sit right there and look me in the face, while you insert your own finger up your ass.  Spread you legs and slide forward a bit.  Show me what you are doing."  

I was still shocked.  I was quaking all over as I slid forward on my chair.  My cock was sticking straight up towards my stomach and dripping as I spread my legs.  I squeezed out some lube onto my index finger of my right hand.  I had to fight to keep looking at Bobby as proceeded.  It was so humiliating.  I knew where my hole was, I had wiped my butt enough, but I had never had to put my finger up it.  

I reached up and spread my cheeks apart and insert a finger at my hole and began to work the finger in.  It was not easy; I was grimacing.  "Relax.  Push out like you are taking a dump and your finger will just slide in.  And that is a nice hairy ass you have there."  

That made me blush even more - here was a guy looking at my ass as I did this to myself.  I worked the finger in, following his instructions.  It did go in easy as I pushed out.  

"Now work it around in there.  See if you can find your prostate in there.  You will know it when you find it.  Slide down a bit more so I can see what you are doing."  He continued to speak in the soft authoritative voice.  

I forced my finger in farther and wiggled it around until suddenly I hit something and wow!  My cock jumped and my whole body twitched as I hit this spot inside my ass.  I was again struck with what I was doing and wanted to turn my head aside.  

"Now, lube up two fingers and insert them up there and wiggle them around."  

I followed his instructions as if in a trance.  I wanted to feel it, but I didn't want to do it.  I was at war with myself.  My cock was winning.  My hole was so tight as I tried to wiggle the two fingers around, hitting that spot again and again.  

"See if you can get three up there.  Man, can you believe this, you are so low that you are sticking your fingers up your ass and stimulating yourself in front of another guy."  He said it without any hatred or rancor, but it ripped my soul to release what I had stooped to.  Nothing could be lower than this.  I worked on trying to fit three fingers in and could not quite get them in.  It was really beginning to hurt.  

Bobby must have seen the look on my face.  "That is good enough for now, we will continue to work on that."  That made my hole clench up, we were going to continue and we were going to work on it.  There was a we in there and a continue in there. I couldn't imagine more.

"Lube up that plug and work it into your ass.  That is the smallest one to begin with."  There it was again.  'To begin with,' implying there would be more.  

As I lubed up the plug I looked at it and was that it flared and then narrowed near the end.  I looked back at Bobby and he had his camera out and the red light was on, as I spread my legs and ass to work the plug into my ass.  My leg was shaking as I worked the plug into my ass.  I had to push out to get my hole to relax enough to insert it.  It looked only 3 or 4 inches long and about and inch or so in diameter, but it felt like a 2 X 4 was being forced into my ass.  I know I squeezed my eyes shut at one point from the pain, but then it hit my prostate and my eyes flew open and so did my mouth and the plug slide into the hilt.  

My cock was continuing to drip more and more onto my stomach as my ass throbbed with the plug in there.  Bobby was recording the whole thing.  My shame was intensifying as my hole clamped around the plug.  The flare was keeping it in my ass.  I would have to really push to get it to come out.  

"Wipe up that goo off of your stomach and lick it off of your fingers," Bobby instructed.  "No with the other hand, the one you had up your ass."  Heat suffused my face as I lifted my slim covered fingers to my mouth.  "That's it, lick your precum off of those ass covered fingers.  Suck them clean.  Can you smell your own ass on your fingers and you put them into your mouth."  

I nodded near to tears again.  This was too much.  

"No! Tell me!" he insisted in that same steady voice.

"Yes," I blubbered out, "I can smell my ass on my fingers."  Hot tears were rolling down my face.      

"What does it taste like having your ass and slim covered fingers in your mouth."  

"It tastes, . . . , uh, I don't know.  I taste the salty sweet of the stuff from my cock and I taste a tang which must be from my ass," I managed to whimper out.

"Does it make you hot to be sitting there naked in front of another guy, a guy who is fully dressed, a guy who has watched you jack off, a guy who has watched you finger fuck yourself, and lick ass and precum off of your fingers?  Does it?"  

"Yes!"  I said as I sobbed.  I couldn't lie.  My cock was so hard and I was so horny and full of lust.  I knew I wanted this and that only added to the humiliation.  

"Tell me what you said, earlier."  

I had to think, it was difficult in this situation, but then I remembered.

"I said I wanted you to do this and I said I would do whatever you asked."  Looking at him through the tears.  

"No matter, what?"

"Yes, no matter what," I said as I hung my head in shame.  

"And you like it?  Look at me when you answer.  Do you want this to stop?"  

"Yes, yes, I like it and I can't imagine it stopping."  

"Okay then ask me if you can pleasure yourself, while I watch.  You want to get off don't you?"  

"Yes! Please may I jack off," as I reached to encircle my cock.

"First, take you hand away from your cock.  Here are some of the rules.  You are going to let me move into your room with you.  You will be naked at all times in this room, whether I am here or not.  Whether you have people in this room or not.  You will ask my permission before you piss, shit or jack off.  I will tell you what you can wear outside of this room. I will tell you when you can eat, what you can eat and where you will eat.  You will do whatever I say, not matter where we are or who is around.  Any hesitation, any argument, any grumbling or complaining will be met with punishment.  You will bathe when I tell you to, you will shave when I tell you to, you will be mine to do with as I see fit.  I do this because you asked me to.  Do you agree?  This is your one chance to get out of this.

"If you say no, that's okay, but I will never visit your room again, nor will I work out with you again.  It will be as if our friendship never existed.  So this is it?  Do you agree?"

I rocked with shame and guilt and tears streamed down my face as I looked at him.  "Yes!" and began really racking sobs and crying.  

He got up off of the bed and walked over to me and wrapped his arms around me and patted my back.  "You are mine now.  I am going to make you go to your limits and beyond and it will blow your socks off.  But I am doing this for you.  You will learn things about yourself and me that you cannot fathom as this point."  I wrapped my arms around him.  He pulled me tight to him and my throbbing cock was trapped between us.  

He said no more, but continued to hold me until I had calmed down.  As I was calming down, I realized that I still stunk of piss.  So I released him and pushed back.  He looked me up and down.  

"You still want to jack off?"  

"Yes," I said as I wiped the tears from my face with the back of my hand.  

"Okay, then slip on some gym shorts, a tank top and your sandals and come with me," he instructed.  I started to ask him a question but remembered my agreement.  

I found a pair of shorts and slid them on trapping my cock in the waistband, and a tank top, and my sandals.  Bobby opened the door and led me out. I started to ask where we were going, but only got to the where when Bobby cut me off.  "No questions.  You will be punished for that, but later tonight."  

He said no more, nor did I as I followed him down the hall and stairs to the exit from the dorm.  I tried not to make eye contact with the guys from my dorm as I left.  I was sure they could tell I was hard and couldn't look them in the face.  It was also hard walking with the plug up my ass.  It made my cock throb and leak as I walked.  And I couldn't walk bow legged like I wanted to, people would really think something was wrong with me.  I know that my shirt was getting a spot on it and I was pretty sure my shorts were getting wet as well.  I had never leaked so much before.  

We went into the library.  He then walked up the stairs, that really made the plug move around and my cock nearly slipped out of the waistband of my shorts.  I had to put my hand up to keep it in place, but not be seen doing it at the same time.  He finally head down some stacks at the back part of the library.  We were in a fairly deserted section.  He stopped and turned.  He had his camera with him.  

"Okay, take out your cock and jack off."  My jaw dropped, but didn't say anything.  I looked left and right as I pushed the front of my shorts down, keeping my cock between him and I.  I wanted release so bad.  

"No, turn side ways.  Yeah, now start pumping."  He had the camera rolling as did as he asked.  I fisted my cock and gripped it tightly and started stroking.  He must have known that I was not going to last long cause he said, "And catch it in your hand when you shoot."  

My eyes were rolling up in my head as I pumped my cock.  I was all about the moment and the sensations in my cock.  It was cumming and I reached out to catch the cum.  A moan escaped my lips as I began pumping rope after rope onto my waiting hand.  It seemed I came for hours, but I know it was just for a couple of seconds.  As my breathing began to come under control, I remembered where I was and looked around.  I didn't see anyone, but I pulled up my shorts trapping my cock again.  

"Now lick your cum off of your fingers and eat every last drop of your own cum.  All the while thinking about the fact that you have just exposed yourself in a public place while a man watched you and you did your most intimate act, here in public, in front of another man and now you are eating your own cum."  

I didn't think I could blush anymore after everything today, but I did again.  And I continued licking the sweet salty cum off of my hand.  When I finished I looked over to Bobby, who had a smile as he continued to film me.  

"I never said you could cover your cock again.  So take off your shorts and walk down two sections of this stack and back."  

My mouth did drop, and again, I looked left and right, but did reach my thumbs into the waistband of my shorts and push them down to the floor.  I stepped out of them, took a deep breath and walked.  Of course, my cock had gotten hard again and I could feel it sticking out from under the tank top I was wearing.  I looked straight ahead and tried not to think about what would happen if someone saw me or entered the stack that I was in.  When I reached the gab between the section I was in and the next I wanted to sprint on past the opening, but didn't figuring that would draw more attention.  Besides, I didn't think I could take running with that thing up my ass.  

I made it to the end of the second section turned around and headed back, seeing that Bobby was taping the whole thing.  It made my cock swell and my upper body flush.  I made it back to him.  Thought about reaching for my shorts, but then didn't.  He smiled.  Filmed me for another couple of seconds and then told me I could put my shorts back on.  

As I bent down the plug in my ass moved and I realized that as I walked away from Bobby, naked like that, that the plug probably showed and he had it all on film!  I trapped my cock in the waistband again (would it ever be soft again?)

I followed Bobby out of the library, he didn't head back to the dorm, but over to a snack bar.  I was getting nervous about someone seeing me and then it dawned on me that I was still wearing the collar as well.  

He stopped at the counter and asked for 2 waters and Baby Ruth bar and Hershey's chocolate bar.  It was a college guy working there.  A guy probably not much older than I was.  While the guy was getting the stuff, Bobby moved close to me, then slid his hand down the back of my shorts.  I nearly jumped out of my skin.  He had never had such intimate contact with me as his hand ran down over my ass, then his fingers slid down my crack, until the found the plug.  Then he gave it a push and a wiggle, making it stimulate my prostate again.  I could feel the juice flowing out of my cock and was horrified the guy behind the counter was going to see the spot on the front of my shirt and probably the one running down the front of my shorts.  

Then guy did turn around and Bobby kept his hand in the back of my shorts.  He continued to play with the plug in my ass.  The guy told us how much it was and Bobby said, "Dave, pay the man."  

I had no money with me; I barely had clothes on.  I looked at the guy and then at Bobby and flustered said, "I don't have any money with me, I'm sorry."

The guy looked from me to Bobby.  Bobby looked from the guy to me and then said, "Well, maybe he will take it out in trade then."  I was blushing again and the guy was looking back and forth from Bobby to me.  "I mean, he might want to have some of this or use some of this."  And he lifted the front of my shirt with his free hand exposing my cock head sticking out of the waistband of my shorts.  At the same time he gave the plug in my ass a wiggle, cause my cock to twitch.  

I must be beet red by this time and didn't know where to look.  The guy's eyes got huge as he looked and saw my cock.  "Dude, I am not in to whatever you are talking about.  I just need the money."  But he didn't take his eyes off of my cock.  I think even my cock was blushing by this time.  

"Are you sure?" Bobby continued.  "He is a great cock sucker and I am sure you could use a good blow job, right?"  

I wanted to crawl in a hole and die.  I just couldn't believe what was going on.  I had never even thought about sucking a cock.  

"Ah, no man. Not into that.  Just need the money."  He did take his eyes off my cock for a moment to look at Bobby and then looked at me again.  "He really gets off on this stuff?" he asked with wonder in his voice.

"Oh, yeah, he can't get enough of it.  Begs me for it all the time.  He likes to show off, perform for anyone, suck anyone and boy, you should fuck him.  Really tight hole.  It fact he has a butt plug in his ass right now, he can't get enough of it."  

My shame was overwhelming me.  Bobby was putting me on display, debasing me in front of a stranger.  But my cock was only throbbing hard and leaking more standing there on display.  Bobby pushed one more time on the plug and removed his hand.  "Pull down the front of your shorts and show him your cock."  

I knew tears were going to start any time, but I reached up and pulled down the front of my shorts, releasing my dripping cock.  I couldn't look at the guy.  

"No, I just need the cash.  But crap man, he does whatever you tell him to?  Can't believe a guy would do that.  Just drop his shorts cause another guy asked him to.  Damn."

Dave dropped my shirt, and reached in his pocket for the cash.  "Stroke it a couple of times, then you can pull up your shorts."  I looked at the wall behind the guy as I quickly stroked my cock and then pulled up my shorts trapping the head.  

"Yeah, he just loves doing whatever I say.  Don't you Dave?" he asked me.  I could only nod.  

"Tell the guy, what you just did in the library," Dave said laying the money on the counter.  

"I, ah, jacked off in the library," I whispered.  

"Yeah, but you also took off your shorts and walked around nearly naked, too, right?"

"Yes," the guys mouth was hanging open now.  

"And did you enjoy it?  Did you do it because I asked you to?  Did it get you hard?  And were you wearing a butt plug up your ass? And did the tape the whole thing?"

"Yes, yes" looking at my feet.  

"Damn, can't believe a guy would do that.  And just because you asked him to.  Man that is pretty low."  He was handing Bobby his change and the bag with the stuff in it.  

"Yeah, really low," Bobby said as he led me out of the place.  

Once outside, he handed me a bottle of water.  I open it and drank down about half of it; I hadn't realized how thirsty I was.  I looked at Bobby as my eyes filled up with tears.  "Why did you do that to me?  I thought you were my friend."  

Bobby opened his bottle of water but didn't drink any.  "I am your friend.  In fact I am your best friend.  I did that for two reasons.  One as part of your punishment for questioning me earlier and two because deep down, I know that you were totally turned on by that.  Isn't that true?"

I immediately answered, "No, why would I want to be treated like that?"

"Because you crave humiliation and debasement.  It makes your heart pump faster, your cock twitch and your asshole tighten up, doesn't it?"

I had to think on that, but then realized that yes, he was right.  It was very difficult to admit, but yes it did do those things to me.  "Yes."  

"Good."  He took the bottle of water and poured it over the front of my shirt and shorts drenching them.  It made the outline of my cock stand out.  Like a wet t-shirt contest for women, only now my whole body was on display.  He took the last of his water and poured it over my head.  "Finish up your water."  

He turned and started leading me across the lawn towards our dorm.  Fortunately, there was less light in the center of the lawn, so soon we were in the shadows, nearly invisible.  He stopped, turned and handed me his empty bottle.  "Fill it up."  It took a second or two.  Why was a being so naïve?  He wanted me to piss in it.  

"I can't piss when I am hard," I explained, "And I have a difficult time pissing with anyone else around."  

He chuckled, "Well, that is certainly going to change.  We can stand here until you piss in that bottle or we can go out into the light and have you try it there.  Which will it be?"  

"Here," I said quickly, not wanting the alternative.  I pushed down the front of my shorts (how many times had I done that tonight?).

"No, drop them down and step out of them."

I did as he said, standing nearly nude in the middle of lawn in the middle of campus.  

I took the bottle in one hand and my cock in the other.  Nothing was happening.  

"We can stand here until the sun comes up, but we aren't leaving until you piss in that bottle.  Either than or you can walk over there to the light, the way you are and try it there."  I told him here again.  "Okay, then relax.  Think of a rushing gushing stream.  It will happen."

I tried to relax and think of streams, but at first all I could think of was how my life had changed since this afternoon in the locker room.  I had been an average guy with some sexual fantasies, living pretty much in my own world, jacking off when I wanted to, not interacting with many people.  Now I was being humiliated and shamed and horny and lusting and constantly hard.  Hell, I had already come twice tonight.  And I was still hard.  I was on film doing all this stuff.  I had done stuff in front of a man and a stranger that I had never thought I would.  I had fantasies of course, but didn't think I would ever really do them and never to this extent.  

Somehow, not thinking about pissing finally got it going.  Piss started to flow out of my almost hard cock and I began filling the bottle.  I looked over and saw that Bobby was filming everything again.  I wondered how it was going to show up in such a dark place.  But that was his problem.  Mine was now that I knew he was watching and taping the flow was slowing down.  But I had managed to get a lot into the bottle.  I finished.  

Bobby took the bottle from me, held it up and looked at it.  It was about 2/3 full.  He handed it back to me.  "Now pour it over your head.  Cover yourself in it."  

He stepped back and raised his camera and began to film as I raised the bottle slowly over my head and began to pour the warm liquid over my head and body.  Before I finished, he told me to pour the remainder over my cock and balls.  I covered them and the bush around my cock.  

"Good.  Now squat down and push that plug out of your ass.  Yeah, now reach back and pull it out.  Feel good?"  I nodded.  "Feel empty?"  I nodded again.

He reached into his sack and brought out the Baby Ruth and unwrapped it.  He handed it to me and said, "Put this back in then."  My cock only twitched more as I reached and inserted the candy bar into my ass.  It slid in easily.  

"Okay stand up."  I did as he instructed.  "You nodded back there.  And you were told you always answer questions verbally.  Remember that because you will be punished again."  I flinched and my cock throbbed.  "Now pick up your shorts.  No don't put them on, just follow me."  

He led me down the lawn through the darkest part and as we got closer to the light, I became worried.  Was this how he was going to punish me?  But he stopped before getting to the circle of light.  "You may put your shorts on now."  Without a word, I followed his instructions, again trapping my rigid cock.  

I followed as he entered the dorm and headed towards my room. Again, I could not make eye contact with any of the guys in my dorm as we headed to my room.  I was covered in piss, hard, with a collar on and a candy bar up my ass.  

When we got to my room, I opened the door.  Thank goodness I had remembered my key.  As soon as I closed the door, Bobby stood looking at me.  Something was wrong.  Shit, I was supposed to get naked in the room.  So I pulled off the wet tank top, pulled down my shorts and stepped out of my sandals.  

"Good.  Now go over to you bed and lie down on your back.  Good now spread your legs.  Yeah.  Wider."  He had the camera out again and was filming.  "Now push that thing out of your ass."  I pushed like I was taking a dump and the candy bar starting coming out of my ass.  

"Okay reach between your legs and grab it as it comes out."  I did until it was all the way out.  "Okay, now sit up on the edge of your bed.  Good.  Now eat it."  

What's the big deal?  It is only a candy bar.  It had been in my ass, but that couldn't be too bad.  I had already licked my fingers.  I did as he said and at first only tasted the chocolate, nuts and stuff, but I did get a tang of that same sharp taste I had tasted before.  But not much.  When I finished, I had chocolate all over my fingers.  

"Lick them clean." I did.  

He turned off his camera.  "You know that it looked like, in the camera, that you took a dump into your hand and then ate the turd that came out?  That is what is it going to look like.  Now I am not into scat - that's what they call playing with your shit - but I wanted it to look like you had just eaten your own shit."  

I was shocked, oh shit; I couldn't believe that.  

"And you licked your fingers clean."  He chuckled.  "Are you ready to cum again?"  

I started to nod, but then remember and said, "Yes."

He smiled, "Yes, I haven't forgotten your punishment.  That will still happen.  I won't forget.  But for now, stand up, open up your pizza box and unwrap the chocolate bar."  

Were we eating or was I jacking off?  


To be continued - enjoy hearing your comments, suggestions, fantasies or experiences that you have regarding this type of story.  Send to [email protected]