If you didn't read my first story, My Fantasy, I basically found an older guy to fullfill my fantasies. Also from the first story, I'd instructed Bill to record our "fun." I really wanted to see it so a couple days after our encounter, I emailed him with instructions just like the first time. The next Saturday I was sitting on my bed and I watched the clock strike 3pm. And right on cue my phone recieves a text that reads: "I have what you want. Meet me in the brown building on 6th ave east. 4th floor, suite 201. 5pm NOT A MINUTE LATER!"
Smiling, I put my phone on the bed and head to the shower. Already excited, I strip and get into the shower to prepare. I do the usual shampooing and body wash. I then started to play with my ass, slowly inserting my middle finger in me. Pushin it in and out for a minute, then adding my index finger. As I start fingering my hole, I think about what is to come that night. He followed my instruction perfectly the first time, so I knew he would be great again.Giving out a little moan. I reach over to my little tote full of goodies by the tub to get my enema kit. I fill the syringe with water and shoved it up in me to then squeeze the water up my rectum. My ass full of water, I try to hold it in, but not for long. It let it gush out and a moan. I continue it until I'm sure I'm clean. Still horny I grab a dildo from the tote. It's about 7" long and about and inch and a half thick. I add a little lube to it and started to lube my ass. I then fucked myself with it while remembering what happened between Bill and I. How hard and fast he was fucking me. Violating my ass with his thick cock. As I'm sliding the dildo in and out of me, I stroke my hard cock and within minutes I came and shot my cum onto the wet bathtub floor.
I dry off and get dressed in a polo shirt and jeans. I glance at the clock and it read 4pm. Time flies when you're having fun right? By the time I get to the building it was 4:30, a bit early. So I went to a bar I'd seen a couple buildings down. So I grab a beer and watched the news for a bit. Not much was going on that was worth remembering. After a couple more I look my cell phone. It was now 4.55. "Perfect," I thought. So I paid my tab and walked back to the office building. I took the stairs up to the 4th floor and while I opened the door to the hallway I looked to see what time it was again and the time was now 5pm. "Oh darn, I'm going to be a minute late." I say to myself with a devilish smile. I walked in the door with 201 in gold letters on it.
"You're late..." Bill said with clenched teeth. And I thought to myself, "Wow, nice emotion. He should be on TV." He nods his head in the direction of "his" office. I walk in with him right behind and I ask, "Where's the video? I have your money." He walk motions for me to sit down and he himself sat behind the desk. I take out an envelope that actually had printed the fake money from pics on the internet. Why use real money for an erotic roleplay. I toss the envelope onto the desk to see him grin. Bill takes it and puts in the drawer of the desk.
"Thanks, but you're late. I told you not to be late. So you're going to have to pay extra." He informs me with an evil smirk. I reply, "That's bullshit, how much now?" And I see his eyes give me a slow "once over." He was pretty much fucking me with his eyes, it made me even hornier.
"How about you come over here and sit on my lap while we discuss our new arrangement, if not you can pay double, your choice." He says. I cuss under my breathe, got up, and walked over to him and sat on his lap. His left rested on my left knee while his other hand was on my waste. His hands roam over my clothes. His left moving up and down my thighs and his right hand worked my chest.
"See, this isn't so bad." He whispers. I can feel his bulge with my ass and I couldn't help but do a slow grind on it. I then said, "Hurry up so I can have my video and leave." He laughs while his left hand was now on my crotch. Rubbing my cock
"Now, the new arrangement is that you will do what I say and want for the next hour, then you can have your video and we can all be happy." He tells me in my ear.
"Fuck you!" The words spat out of my mouth. And he whispers, "I plan to..." He gets up with me still in his strong arms and bends me over the desk. Just imagining how I look bent over had my ass yearning for a cock in it. He grinds his crotch into my backside will caressing my ass.
"You're a bad man..." I said softly. Bill laughs and says, "You like it...and you'll enjoy it my friend." I can hear him unbuckle his belt and then taking his slacks off. For fun, he pokes me a couple times with his rock hard cock and chuckles. I feel his hand go up the back of my shirt and sliding it up my bare back. I can feel the cold office air hit my skin and suddenly he yanks my jeans down. I shiver as my ass feels the air conditioning.
"Look at what we have here," Bill says devilishly as he reaches under me and grabs a hold of my erect cock. He continues, "See, I knew you like it." Feeling his grip on my meat I can't help it but move my ass towards him.
"Oh you yea, that's it. You like me doing bad things to you." He tells me. I can feel his cock slide up and down my backside. I hear him open a drawer and then feel the cold liquid of lube drip down the split of my ass. He then proceeds to rub it all over my ass and then around my asshole. I give a little moan and I could barely contain myself. He starts to rub his meat between my cheeks lubing up himself and I was too impatient. I backed up and his cock slide completely in me, pretty much knocking the breathe out of me.
"Oh fuck! Ok, if thats how you want it!" Bill yells. He pulled all the way out and rammed it in me, hearing his balls slap against my cheeks. And again and again, he continue to hammer me as I yell, "Uh! Uh! Uh!" with every thrust. His strong hands on my hips pulling me into him. I ended up knocking things off the desk while trying to find something to hold on to. He was fucking me so hard and it felt so damn good. I couldn't help but scream with every thrust, "Yes! Yes! Uh! Fuck! Me! Fuck! ME! Ah! Ah! Ah!"
"Fuck your fat ass is tight boy!" He yells. Surprisingly he pulls out and grabs my head and brings it towards his cock. Ready for it with my mouth open, I take it and suck it hungrily. Licking and suck his head like there was no tomorrow. Bill pulls my head back and slaps my lips with his cock a few times before shoving it between my lips again. I can feel that he might be ready to cum but he stop and stands me up to push me back into the desk. I fall back and he grabs my legs to spread them. With his eyes full of lust, he stabs me with his cock again. I can't take my eyes off of his face as he fucks my hole. The sensation of his cock sliding in and out was too much. I take hold of my own cock and start jacking it. And within minutes I shot cum onto my chest. And right after I did, Bill give me own last thrust and shoots his load deep in my rectum. He lets my legs go and collapses on top of me. His head comes up and kisses me deeply. I feel his chest breathing heavily against me. Bill reaches into the desk and pulls out a slim cd case with a dvd inside it and places it on me. He then got up and pulled out. I can feel his cum seaping out of me and onto the desk. As he's getting dressed he says, "Enjoy that dvd, I did." I get up and start cleaning up the desk and around the office, picking up the things I knocked down.
"You have a pretty nice office." Bill says, I thank him as I'm getting dressed. I could still feel his cum oozing out of me and against my jeans.
"Don't break character..." I tell him sternly. With a grin he leaves. After I made sure everything was in it's place. I went over to the corner where a filing cabinet was. Sitting there was a Flip video recorder that had been recording everything. If you can't tell by now, I'm a bit of a voyeur. I take the camera and leave.
As I take the elevator down I start thinking about what our next session will be like and what I'll have him do. But little did I know, my plans would be changed and that I would no longer be in control.
(Once again, if you enjoyed it let me know. If one person just likes it I'll continue. This went on for a couple years so there's plenty to write about.)