Chapter 5: Look at Me
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I met Sir once more that week. Again it was at the park & ride at night after work. Sir had me wear the cock cage earlier that morning which made me feel hopeful that I would get to meet Sir later that day which, thankfully, I did. So we were behind the boulder again, me on my knees with the blindfold on and Sir's huge cock in my mouth again. He was getting close to cumming when we heard voices of men heading our way. Sir had me stand up as he zipped his pants up. He had me turn my back towards him as he slipped my blindfold off my face. He admonished me to look straight ahead and not to look back at him. He pulled me close to him and hugged me from behind. We did this rather quickly that by the time the men had appeared from around the boulder, Sir and I looked like a couple posing for a picture. I secretly enjoyed his hug. His hardon pressed against me.
The newcomers were two middle-aged men, average build. One was wearing jeans and a black leather jacket while the other was wearing office clothes with a jacket over it just like I was. Leatherman was in the process of unbuckling his belt when they noticed us.
"Oh," said leatherman.
"Hey," Sir said.
"Didn't realize somebody was back here," office guy said.
"That's o.k.," Sir replied. "We were just about to leave anyway."
Sir moved his hands to my shoulders and nudged me to go. Leatherman was looking intently at us and just as we passed in front of them he called out.
"You know, you don't have to go. My friend here was going to give me a blowjob, I'm sure he wouldn't mind taking on two more."
"Yes, definitely. The more, the merrier." office guy said.
Sir was walking me a few more steps when I felt him pull me to a stop. I then felt the blindfold being slipped back over my eyes again.
"What's with the blindfold?" leatherman asked.
"The boy is not allowed to see my face," Sir answered.
"But you two were - nevermind, it's not my business." leatherman said. "You joining us?"
"Sure," Sir said as he lead me back a few steps. Sir told me to drop my pants. I obeyed.
"Can I?" leatherman said.
"Go ahead, he won't bite." Sir said.
I felt a pair of hands feel me up. Leatherman's, I gathered. He gave a few tugs on my balls.
"He's caged." leatherman said.
"And plugged too." Sir added.
Leatherman slid his hands underneath my shirt and lifted it up somewhat.
"Look at these six pack." Another pair of hands joined in - this I figured was office guy's.
"You've got a nice catch here. Where can I get me one these boys?"
"Oh, they're out there." Sir said.
"So, he does all you tell him and he hasn't seen your face yet?"
I guess Sir nodded his head cause I heard the guy say "that's hot." Leatherman gave my butt cheek a good sqeeze.
"On your knees, boy." Sir said.
I was ready, I parted my lips as I knelt. I heard zippers zipping and a cock breaking the treshhold of my lips. At first I thought it was leatherman's but quickly realized it was Sir's.
I heard some sucking sounds beside me, I guessed office guy is sucking leatherman off now too.
I felt like I had to prove I was better at this and really worked on Sir's cock with enthusiasm. Maybe a little too much of it.
"Easy, boy," Sir said.
I eased down a bit. After a few minutes of this, leatherman and Sir decided to switch places. Leatherman's cock was uncut and while it was not as long or as fat as Sir's, it was still big. It's mushroom head had a pronounced flared edge which felt good going in and out through my puckered lips.
I heard Sir moan.
"Mmm, you're an expert at this, buddy." Sir said.
I heard office guy mumble in agreement.
Not only was I feeling competitve now I was feeling jealous as well. I hope he chokes on Sir's big cock. but he didn't - he wasn't gasping for air like I often did. I put my best effort with leatherman's dick. pulling the foreskin down and working the head. Pushing it back up and sliding my tongue between the folds. Maybe if my man cums first, Sir would regret switching to the other guy.
By the sounds if it, Sir came first but even while Sir was moaning in pleasure, my guy started cumming as well. And he shot load after load. He kept on cumming like he saved a month's worth if it for this night. I swallowed it all though. I figure that's what a great cocksucker would do.
After they've zipped up and thanked each other (Leatherman thanked Sir, not me). The two left me and Sir alone again.
"Maybe I should start charging men for the use of your mouth. Make you earn me some dollars."
I said nothing - I was still swallowing the remnant cum inside my mouth. Sir had me stand up. When I did, he took out the cage then he also pulled out the butt plug. Then he was pushing it back in but when I felt that there was some resistance against my anal ring, I. realized that it wasn't the same plug but a bigger one. When it did slide in - I could tell there was lube on it - the feeling of fullness that I had initially felt with the first plug but had diminished a bit this past couple of days - had come back. I felt full and stretched again.
"Here, keep this." Sir pushed a ziplock bag into my hands which when I felt what was in it deduced that it was the cock cage and the smaller butt plug.
"You know the drill. Count to 100 before leaving."
And he left me once again.
I arrived at Starbucks ten minutes earlier than our scheduled meeting time of 9 a.m. I was excited, this was the Wednesday of the third week into my contract. Sir had me take a day off from work. He didn't mention anything about putting on the blindfolds - we were after all meeting at a busy public place during the day. I was excited; this may be the day I finally get to see Sir's face. I was starting to doubt that I ever will.
I scanned the crowd at the coffee house looking for someone with Sir's boots on or someone bigger than me which I deduced Sir to be. That didn't really limit the crowd that much as I am really not that tall or broad myself - a couple of old guys I could rule out which left me with four guys. Two were sitted by the couches looking at their phones and the other two were on line for ordering looking like they needed to be somewhere else - most likely at work. I figured I'll fall in line and get myself some coffee to give my fidgety hands something to do. By the time I got my coffee, no other guy had come into the shop. It was already 9 o'clock. I took a seat closest to the door so I could see everyone who enters.
I looked out of place in that coffee house as most of the customers were in office clothes or at least wearing pants, shoes, and shirts. Me, on the other hand, as per Sir's instructions, was only wearing nylon basketball shorts, flip-flops, a thick jacket, cock cage, and a butt plug. I kept my jacket zipped all the way up to hide the fact I wasn't wearing any shirt underneath. Maybe I shouldn't have sat close to the door as I was freezing from the cold winter air outside whenever someone would walk in or out of the store.
A guy walked in wearing a suit and tie and I considered for a moment that it might be Sir. He saw me looking at him but he just went on straight to the ordering line.
"I don't wear suits." Sir's voice said from behind me.
I turned around and this guy wearing a NY Mets hat was smiling at me. I had seen him sitting at the corner of the coffee house but dismissed him readilly cause he didn't look all that big where he was sitting and really cause he looked ten years younger than his supposed late thirties age. And yes, he wasn't wearing a suit but a hooded jacket over a white shirt. He had on jeans and sneakers - no black leather boots. A backpack slung over one shoulder. Standing there, evidently he was not the college dude I mistook him to be.
"Hi, boy."
"Sir?"
"Are you wearing a shirt underneath, boy?" he said in a voice that is not exactly loud but can be heard clear enough by people around us.
"No, Sir." I quietly said.
"You seem nervous. Would you rather talk somewhere more private?" I don't know if he said this because it's his naturally self-assured way or if he was talking like this to embarrass me further.
"Yeah, somewhere quieter would be better?" I mumbled.
"O.k. then," he said as he walked out of the door.
I quickly followed him, chucking my hardly drank coffee in the trash bin on the way out.
I followed him across the parking lot thinking we were heading to his car but instead he stopped in front of the passenger side of my car.
When we got in, I turned the heat on while Sir took off his jacket.
"Take your jacket off too."
I complied and felt naked since my car windows weren't tinted and there were some people walking to and from their cars. Looking at me, they might very well think I'm completely naked.
"You wanna lose the shorts too, boy?"
I didn't know whether he was asking me, sugggesting it, or commanding me.
"I'd rather not, Sir. We are in public."
He took off his hat and ran his fingers through his hair which was thinning on the top already. I got to have a good look at his face. He was handsome. Though his face wasn't as rugged as I had imagined it to be. It was more rounded and less angular than I had thought. He had a full five-o-clock shadow that you could tell was well maintained. But it was his eyes. Damn! They're a color that cannot decide whether they're green or blue. He looked me straight in the eyes with those. I looked away. I didn't want him to know I was mesmerized by them. He didn't say anything, so I sighed as I pulled my shorts off and placed it on the side of my seat.
"Good, boy."
He reached over and unlocked the cock cage and took it out from me. He then proceeded to wank my soft member till it was pointing straight up by itself. My breathing was becoming heavy. I'm so fucking horny right now. I haven't cummed in two weeks. He lightened his touch on me sensing that it wouldn't take much to bring me over the edge. When a pool of precum collected at the tip of my weenie, Sir scooped it up with a finger then offered it to my lips. I licked his finger clean. Half of me couldn't care less that I looked like a total slut to anyone walking outside; thankfully though there weren't any at that moment.
"Let's get going. Drive us out of here."
As I got the car out if its parking spot, I asked Sir where we were going.
"Your house" he said.
Fuck, I thought, I didn't see that coming.
There were two traffic lights we have to pass before I could take the highway. I prayed that they would both be green when we passed them. The first one was but the second one just turned red as we approached it. Damn.
A car driven by an old guy stopped to the right of us. If he looked this way he would see all my nakedness and probably even my hardon. To our left was the left turning lane and a woman drove up to it waiting for her light to turn green. She did look our way, probably wondering why I would be half naked in the middle of winter. If she only knew that that was only half the truth. What would I tell my wife when she picks me up from jail for indecent exposure, I wondered.
At the highway, I had a different concern of avoiding trucks which for sure the drivers of which would be able to see down through my window and know I was driving naked. My boner had subsided but once in a while it would go into a semi hardened state which I was cwrtain didn't escape Sir's notice.
We got to my house finally and wished that I had kept the garage free of junk so I could just drive into it and close the garage door behind us. Instead I had to park in my driveway. There were no neighbors out which was a good thing but I wouldn't discount the possibility that they would be able to see us from their windows.
Sir started stroking my weenie to full mast again.
"Leave your jacket in the car and put only your shorts back on then wait for me at the front door." he said.
When I got out of the car I walked very briskly to the front door, my hardon bouncing against my shorts. I unlocked the door but didn't open it yet. Sir took his time getting out of the car, putting on his jacket, and walking to the front door. By the time he got to where I was, I was shivering in the cold.
I let him in first then I closed the door behind us.
"Take your shorts off, get me a glass of water, and kneel before me." He wasted no time in barking orders; I wasted no time in doing them.
He drank the water then placed the empty glass on the living room coffee table. He took the liberty of checking out the house going from room to room.
After a while he told me to crawl to him. I followed where his voice was and it led me to the bathroom. l have to piss - I've been saving this all for you.
We have a small bathroom and he stood in front of the toilet bowl facing the door and I was on my knees in front of the sink, my feet barely making it inside the bathroom.
Make sure you swallow all my piss, otherwise, you'd going to be doing a lot of cleaning. I had his cock resting on my tongue when he let loose. It was apparent right away that I wouldn't be able to keep up. I swallowed as fast as I could but a lot gushed out of my mouth wetting me, the tile floor beneath, even getting some drops on Sir's sneakers.
"Tsk, tsk, tsk...you have a lot of cleaning to do." he said when he had shaken off the last few drops of piss into my face. "Start with my shoes".
It really did not get wet all that much - just a few small drops here and there but Sir made me take them off his feet and lick the whole thing over - even the soles. He then had me remove his socks and give his feet a tongue bath as well. His feet weren't necessarily stinky but you could tell he reused socks that needed to go to the wash already. When I was done with that he then had me clean the tile floors. A puddle of piss had collected on top of the tiles that licking it was not drying it up fast enough - Sir had me sip it up. It felt so humiliating doing that but I manage to virtually dry that floor up with my tongue and mouth.
"How about you, do you need to take a leak?"
"No, Sir."
"Are you sure?"
"Uh, maybe I do need to go, Sir." I said, knowing then that that was the answer I should have stared with.
"O.k. then, Go lie down inside the tub and rest your feet up on the wall."
I did what he wanted - already seeing where this was going.
"Higher." he said.
I scootched over closer to the wall to bring my feet up higher.
"Now lift your butt up and pee into your mouth."
I tried to do what he said put I just couldn't go. My bladder wasn't that full yet plus the discomfort or the fact that Sir is watching me do this wasn't helping either.
"C'mon, boy."
"Yes, Sir." I closed my eyes trting to concentrate. A few drops dribbled out but stopped.
"C'mon, don't stop."
I tried focusing again - trying to find that trigger to get the flow going. and then I did. The yellow stream flowed out of me and splashed into my face.
"Into your mouth now boy - swallow it up."
Half I manage to swallow, half went to my face and chest. After that, Sir asked me if I douched, I said I did. He then told me to take a quick shower while he waited outside.
When I had washed myself off, I found him sitting in the living room sofa watching TV.
He beckoned me over and had me turn around slowly in front of him. He was inspecting me.
"We need to shave you're pubes off - boys do not have pubes, only real men do."
I've never shaved my pubes ever. So, I wasn't too keen on the idea. But it wasn't just an idea - it was something Sir wanted so I knew I didn't have a say on it. He opened his backpack and pulled put out a cordless electric shaver he then had me follow him to the kitchen where I was told to stand in the middle.
He grabbed a nearby stool to sit on then just started shaving my pubes off. He was pushing my weenie to one side then the other, the constant touching caused me to harden again.
He then had me bend forward and spread my ass cheeks apart. He pulled the plug out and started shaving my pussy hair. It took him a long time doing that - I didn't realize I had a lot of hair down there.
When he had me straighten up again, I thought it was all over but instead he had me lift my arms up and he shaved my armpits as well.
"Sir, what will I tell my wife when she sees I'm all shaved up?"
"Do you want me to shave your head as well?"
"No, Sir."
"Then shut up cause it's not my problem, boy."
For good measure, he shaved some errant hair growing on my nipples as well. I was thankful he left my legs and head alone. When he was done, he admired his handiwork.
"Much, much better," he said.
He had me clean up the mess of hair on the kitchen floor then had me kneel on the middle of it. He then stood right in front of me. A position we have been on several times before but it's the first time I'm seeing it with my eyes.
"Take my cock out, boy."
I unbuttoned his jeans, zipped down the fly, pulled down his pants a little then pulled over his semi hard cock out of the confines of his boxer briefs. There crowned by his well trimmed pubes, was the special guest of my mouth, the emblem of my fantasies, here now, fully visible - right in front of my hungry eyes and mouth.
"Worship your master's cock, boy."
I gave it gentle kisses to ask for forgiveness for doubting that I did not want it and I gave the head long licks for supplications that it may grow to it's full glory. My devotion was answered as it throbed to its fullness. Nine inches if I was to guess with an impressive girth to match it.
I took it into my mouth like I had done in the past and though I was enjoying seeing my master's meat up close, I cannot help but close my eyes as I went into the rythm that had in the past made it grant the gift it bestowed on me.
Sir stopped me just as he was nearing my benediction.
He had me stand up, held me by my hardened pole and led me into the master's bedroom.
With both me and my wife usually in a hurry ro go to work, we dont get to make our beds. Crumpled sheets and strewn clothes lie on top the bed. It didn't matter to Sir, he pushed me down to the bed and he started to undress adding his pile to the mess already there. My feet hanging over the floor, I propped myself up on my elbows to stare up at this man with both hunger and reverence. I wasn't mistaken, he did have broud shoulders and a full pumped chest, he had a bit of a beer gut but you can tell from his upper abs that he had thick solid muscles underneath. And his torso was graced with hair in all the right places. His arms looked like they had seen work - not the type grown in the gym like mine. He had a tattoo of a tiger on his upper left arm. It befits him, I thought - this strong sly man.. He had me slide up on the bed then he climbed in as well - he was on all fours above me.
"Is this the bed where you make love with your wife?"
I wanted to just nod as I was still busy admiring his manliness.
"Yes, Sir."
"Is this where you fuck her pussy?"
This question shook me out from my reverie.
"Yes, Sir." suddenly self conscious.
"What would you say if Sir tells you this is where he wants to fuck your pussy?"
"I don't know Sir. I haven't thought about that. I guess I should object but -" and I didn't have the nerve to finish what I wanted to say.
"But what, boy?" His face inches from mine.
"But, I, uh... don't really care where we do it Sir so long as Sir fucks me with that giant cock of his."
"Such a slut." Sir said smiling.
He lowered his head and kissed me. Oh, if I could melt at that moment I would. Instead I kissed him back with the same intensity he had and ran my hands over his arms.
He rolled to the side while we continued to kiss and I don't know how long we were kissing each other but soon enough I find myself on top of him and his hands caressing and pulling my ass cheeks aparts. He pulled me on a tight hug, my head on the bed next to his ear, my boner pressing against his belly.
"Count it out, boy?"
I didn't understand what he meant when he suddenly slapped my ass hard. It caught me by surprised me but I understood.
"One, Sir."
Another slap.
"Two, Sir."
And another.
"Fuck," I said, "four, Sir."
And with each successive slap, I couldn't help but grunt in pain. I was biting down on the sheets.
He stopped at twelve.
"That's like a dozen roses, boy. What do you say."
"Thank you for my pun - I meant thank you for my gift, Sir."
He kissed my. cheek.
"Good, boy. Sir's very happy you are learning, boy."
He stood up and left the room - came back carrying his backpack. He pulled out some ropes. He had me lie down on my back in the middle of the bed. Then he tied my wrist and ankles on the four posts of the bed.
He then pulled out what looked like a long wireless microphone from his backpack.
"You remember what this is."
I did not as I haven't seen it before but then it dawned on me.
"Mr. Electrowand, Sir?"
"Good, boy. You remember."
And I did remember - Sir made sure of it. He touched me with the wand all over, from my toes, to my nipples, from my arms, to my balls. It elicited groans and gasps from me.
He set the wand aside the positioned himself on top of me, straddling my chest, once again his cock before my face. This time though not only did he have me service his cock but to pay special attention to his balls as well. I licked them and gently suckled on each orb. He seemed to like that a lot.
Eventually, he moved to my side and caressed my body - gently rubbing my skin - all over except my denuded weenie and balls. He teased my hole and then slid a finger in. He moved it inside a bit before starting to finger fuck me. I don't know why they said being fucked was painful - all I was feeling was pleasure from it. He pressed two fingers in. There was a bit more pressure but a moan from me gave the signal to Sir that I was all well.
"I see the butt plug has loosened your pussy a little bit." His two fingers going in and out. "That's good."
He got out of bed and unfastened the ropes around my ankles then he grabbed a bottle of lube from his backpack. He applied liberal amounts of thw liquid on his hands and my pussy lips then proceedes to loosen me up further with three fingers up my hole.
"Fuck me, Sir." I begged him. "Please fuck your boy's pussy."
This elicited a sly grin from Sir but he just kept his finger fucking up.
In what felt like forever, Sir finally lubed up his monster pole. and positioned himself in front of me. He lifted my legs up which he rested over his shoulders. He then placed his cock head on the entrance of my virgin pussy, rubbing it around a bit, and then he pushed in.
Oh fucking motherfucking fucker, I said to myself. The pain was undeniable.
"Aa-aa-ugh!" was what I managed to say aloud.
How much thicker than three fingers can a cock be?! I thought while in pain.
"Is my big cock hurting you, boy?"
"Yes, Sir." I whimpered.
"That's good, boy." He said though he was hardly moving his cock inside of me - pausing every so often after tiny pushes inward. "You know why it hurts, boy?"
"Cause you have a big cock, Sir."
"Because this big cock is crushing the last piece of manhood you have left." Having said that he pushed in even deeper. I yelped in pain.
I wish for the pain to stop - I wanted him to pull his cock out but I couldn't move even a bit for fear that it would hurt even more.
Sir slowly worked himself deeper into my pussy.
"This bed has finally seen what a real man is. I'm taking your manhood on the very same bed you exert your manhood on. I'm fucking your pussy where you fuck your wife's pussy."
"Uggh," I said in seeming response to what he said.
There was a tinge of guilt there as he said thoae words but I couldn't really worry about that at the moment. I concentrated on trying to not feel like I'm being ripped apart into two, reminding myself to keep breathing. I didn't realize I was closing my eyes.
"Hey, look at me, boy."
I looed at him. Looked straight into his bluish green eyes. He started pushing in and out without pausing. With every thrust, he was going deeper. I could only grunt from the pain. But I didn't break contact with his eyes and somehow that helped. The pain was still there but there was some sense of pleasure mixed in as well.
"Yeah, that's it boy. Give it all up for me."
Though his actions were rough, his words tinged with cruelty, his eyes, however, betrayed him - I could see no malice in them. I felt like he was giving just as much as he was taking. He was breaking away my manhood as I knew it but he was giving me a chance to redefine it for myself without fear.
I was grunting - no, no longer - I was now moaning with each of his thrust.
"Yes, boy. That's it."
"Uh-huh, fuck, uh, yes, Sir."
"Who owns you, boy?"
"You Sir, you own all of me, Sir."
He kissed me. I kissed him back. This was what I heard about, this was what porn sites make you imagine it would feel. It did not disappoint. The fullness I felt, the pleasure that swept in, the thought of my surrender, the pain that still lingers - all of these did not disappoint. My knees at this point were next to my ears. I felt him give one big thrust and I knew he was completely in. He stayed like that for a few moments before beginning his rythmic pumping. There was no other thought in my mind at this point except to enjoy what this man was doing to me.
He pulled out after some time and there was an audible pop when he did so. I felt empty now. I needed him back in me. Sir untied my wrist and had me get down on all fours. He pushed my shoulders down and proceeded to reinsert his cock into my no longer virgin pussy. The pain felt fresh again but it wasn't as bad as before.
He fucked me now and I didn't want him to stop.
We changed positions a few a couple more times; we were in a spooning position for awhile and then he had me sit on his cock while he laid down on bed - this position seem to make him go even deeper in me which I didn't thought was possible anymore. Eventually we were back in our original position with him on top and me on my back. This is when I knew he was close to cumming.
"I'm going to breed you now, boy."
"Yes, Sir, please, give it to me. Breed me, Sir."
And he did, though I didn't feel any of the cum in me - he must have shot it deep within me. He shuddered in pleasure. I sighed happy with his pleasure and thw knowledge that his seeds were in me. He rolled next to me on bed - both of us exhausted.
He came twice more that day. Once in my mouth and the third one up my ass again, doggy style.
When we took our shower his demeanor was different. It was like I was his lover, not his slave - he soaped me up gently and kissed me. I returned the favor.
We got dressed and we drove to a deli nearby where we grabbed a couple of sandwiches and soda. We ate in my car there in the deli parking lot.
"So, did you enjoy that?" He hasn't used the word 'boy' since after the shower. I took that as a cue to talk more naturally to him.
"Yes, I did." I said with a smile.
"I did too." He said.
"I'll say, you came three times."
"I could probably have gone for a fourth but I don't think your ass can take any more."
"I do feel sore down there."
"There might be some bleeding" he said, "that's normal but you have to watch it to make sure you're not bleeding too much."
I nodded my head and tried not to think about that.
"Can I ask you a question?" I said instead.
He nodded.
"How did you find out about all this info about me - my whole name and address and all? Did you find my driver's license when we were at the motel?"
"No, I thought that was very smart of you to hide it. I even searched your car and I couldn't find it. Did you bring it with you?"
"I kept it in the trunk."
"Smart. I looked there but I guess I didn't look hard enough."
"Then how did you do it then?"
He smiled while looking me in the eyes for a second or two before speaking.
"I followed you home from the motel."
"Ahh" I said. The thought slowly making itself clearer in my mind.
"Once I knew your address, it's just a matter of using the internet to find out the rest."
"That's kinda creepy, you know?" I said. "But to be honest, it's making me horny just thinking about it."
"I have no intention of hurting you or your wife."
"I had realized that earlier today while you were fucking me."
"Why? Was I too gentle?"
"Ha! No way." I laughed. "But you weren't merciless either."
We finished our lunch and I dropped him off at the Starbucks. He made sure I drove off before he even walked to his car. A secretive guy that Sir is.
I didn't get to cum at all that day nor was I allowed to not until the Friday night when Sir texted me and told me that I was only allowed to cum after I bring my wife to climax three times that weekend. It was a weekend I'm sure she will remember for a long time just as I was sure that it was a week for me that I will never forget.
Thanks for reading. Send comments, suggestions, and criticisms at ryan_sub@hotmail.com. I would love to hear from you.