Loren Ch. 05

Loren's story

I was tired of Shelby and all of his lies. I was paying his way and expected him to show enough respect not to cheat on me right under my nose. I had no problem with him having sex with other people when we were in our group setting, I mean I was screwing other men also, but to take someone like Dan Redvern out on a date, using money I gave him to pay for the date, that was just taking things too far.

The worst part of the whole thing was that Waldo was right all along and that irked me more than anything. Fucking Waldo, always butting into my life, why couldn't he just leave me alone? We had a long term affair and it ended, why couldn't he just leave things be?

Instead what does he do? He hires a fucking private investigator, probably the same one he used when he suspected I was stepping out on him, which in fact I was. Lancaster was just too good to pass up. I wasn't even thirty years old, hadn't even reached my sexual peak and I was strapped with fucking Waldo Liebacker and his 'Tuesday night we eat at Umberto's, Thursday we eat at Delmonico's and the weekend -- Holy Fuck I had to listen to his inane ramblings and fucking opera every weekend for five years. I was almost willing to go straight to get away from him. Then Lancaster showed up at one of our group parties. Waldo was always reticent about me being with anyone else he preferred I watch him fuck whoever he chose. Lancaster shed his clothes and there between his legs was this beautiful fat cock and I wanted him. I watched man after man, including Waldo, fuck him that night and all I could think about was him shoving his cock in my ass. I admit that Waldo was a fantastic top and knew how to bring ultimate pleasure to the bottom underneath him, but the time for me to move on from Waldo had arrived and Lancaster was as good as anyone to use to make the break.

But I digress. Waldo hired a PI to follow Shelby and what does he find? Shelby pawning the jewelry and the gold watch I gave him to buy expensive gifts for Dan Redvern. It didn't even dawn on me to ask Shelby what happened to the watch I gave him. Who would have thought that he would have been so crass as to sell a piece of jewelry that I took the time to have engraved professing my desires for him? I just couldn't understand why Shelby would want a cheap hustler like Dan Redvern when he had a guaranteed paycheck with me. I'd had Dan before, he was okay - he just wasn't anything special. Dan was a bottom and for the most part so was Shelby and he didn't have the bank account I did, what could he want with someone like that?

I needed to get away to think. Things hadn't been great between Shelby and me for months. At work he wasn't doing well, he wasn't making his sales quotas and Bill Wallace wanted him gone. He felt Shelby was distracting me too much and not only bringing the agency down but me also.

In addition Shelby had also begun pushing me to let him move in. I wasn't ready for that type of commitment. I didn't mind him spending a couple nights a week at the apartment or me with him at Sam's house but that was all.

I knew why he wanted to move in. Mainly he didn't like living with my uncle. Sam liked to surround himself with pretty little boys, all of consenting age mind you -- as much as Sam liked them to be young looking he would never have considered touching anyone that didn't consent or that was underage, he was quite meticulous about making sure that anyone he touched filled both criteria.

So he loved his nineteen and twenty year old men to look young, to each their own. So he loved to dress them in little girlie underwear and have them prance around the house like that- who cares, he wasn't hurting anyone.

Shelby with all his southern genteel ways found it distasteful. He didn't like prissy little men. On more than one occasion I had to go over there and break up shouting matches between Sam and Shelby. Shelby always wanted to show Sam what a real man could make him feel. What he didn't understand was that each time he picked a fight with Sam he was burning his bridges just a little more -- and on both ends because not only was Sam getting ready to kick his ass out, I was also getting tired of his worthless ways.

I also began to think that Shelby figured if we were living together he would be able to continue with his outrageous spending habits. Sex, that's what all this was about. Shelby was a great lover and knew how to prostitute himself to get what he wanted. Every time I tried to curtail his spending habits he would cut me off sexually until I let him get the suit he wanted or the shoes that he couldn't live without. I hated to admit to myself that I was addicted to him and just wasn't ready to give him up...well not until I found out about Dan. That was the proverbial straw that broke the camels' back.

Shelby pleaded with me not to break off our relationship and I couldn't think around him. Sam volunteered the house in Connecticut. It was quiet and I could be alone. The best part was that Shelby had never been there before and couldn't follow me.

I told Shelby on Friday morning I was going away. He begged me to stay and talk things out with him. I simply refused. I was in my office, gathering some paperwork together in case I felt like working over the weekend when I came across my ticket to the gala. I debated whether to give my ticket to Shelby but at that exact moment Dan Redvern walked into my office. What better way to get back at Shelby then to let Dan go to the gala and get wooed by all the rich men that would be there. Wouldn't it have been good revenge if Dan met someone at the gala and dumped Shelby for someone with real money? I looked at the ticket and offered it to him. Dan appeared to be appreciative about the ticket but told me he didn't own a tuxedo. I don't know why I offered to let him borrow one of mine. Again I think that I wanted to get back at Shelby in some way. Now not only would he be at the gala but he'd be wearing one of my tailor made suits that I didn't even let Shelby wear. He followed me home when I left the office at one.

In the quiet of my apartment I was able to confront him about his relationship with Shelby. He was reticent to talk about it at first, but after a rather large snifter of my expensive brandy that he lapped up like it was water he opened up to me.

"Shelby told me that in all the relationships he had in the past his lovers always give him a sizable allowance and allowed him to do as he pleased. He was also provided an adequate place to live and the only expectations the men that kept him had of him was that he be there when they wanted him. Shelby came from a family that never had to work for living and was tired of the job, having to report to you all the time and beg for everything he expected to receive as your lover." Dan said. "Even though Shelby is a kept man he is a man that commands control. He finds men that are rich and needy and shows them that what they had been missing all their life. He lost that control with you and to compensate for it he needed to control me. You bought him expensive things, he pawned them and turned around and bought me expensive things. He said that in every relationship he had in the past he always had someone on the side like me. After awhile he didn't even bother to pawn the stuff, he just gave me the stuff you got him. Like this." He pulled out the gold cigarette case I had recently bought Shelby for our one year anniversary. He handed it to me telling me that he didn't smoke and didn't feel right taking it, especially because I had inscribed it so personally to Shelby.

"I can't ask you to stop seeing him." I said. I was filled with so much rage and was trying to keep myself in check. "But starting next week I'm afraid we won't be needed your services at WKB anymore. Oh and Dan...I'll let the other ad agencies here in Manhattan know that you aren't dependable enough to be counted on." It was a threat I intended to keep -- not because he was seeing Shelby but because I wanted Shelby to know I was the cause of Dan not seeing him anymore.

"I will do anything to keep job my Loren." He was begging me and truth be told it always was a turn on to hear a man beg me for anything.

"Go to the room and get ready for me. I'm going to fuck you to seal our understanding and punish you for being with another man's man."

"Y...yes...sir..." he said instantly, exciting at the prospect of being with me again. Dan loved feeling the pain of a firm paddle and knew that I would bring him the pleasures he loved. I decided even before I walked into the dungeon that he would get fifty strokes of the paddle. It would be enough to make him cry but not enough to make him too sore and unable to sit through the gala that evening.

Dan didn't disappoint me. His cries filled the room fueling me on as I counted out his punishment. I gave him the first ten, then stopped and berated him, gave him another ten and stopped and humiliate him -- I stretched his punishment to last almost an hour and even added some cock and ball torture into the mix that had his cock spewing cum all over the place. We both loved every minute of it. When I was done I dropped the paddle and plunged my cock into this wanting ass. He loved my thick cock and I'm sure he appreciated it more than Shelby's, most men did. Shelby is a very handsome and dynamic man and a fantastic bottom but he wasn't blessed with a sturdy cock. It was more along the lines of -- 'yeah it's there and I feel it but I want more'. When my cock goes into an ass you know it's there and it's going to pound the sides and bottom all at the same time.

I came in his ass twice before I was done with him. He was resting on the small bed in the dungeon while I showered, dressed and packed my overnight bag. He asked me if he could stay, take a bath and rest a little more before he left. I had no problem with him doing that and left the apartment at three in the afternoon.

I ran into the Friday afternoon rush to get out of the city and it took me over three hours to make it to the cottage outside of Clinton. Sam had called the caretaker Friday morning who opened the place for me and stocked the fridge. I stopped in town and bought a couple bottles of scotch and filled the car up with gas before going to the cottage. It was close to seven when I walked in the front door.

I've never been a man that enjoys being alone and for the first hour I was there I cursed myself for not bringing Jessie with me. I almost turned around and drove back to the city because I hated the quiet surrounding me. It was off season and the other cottages were empty and I was all alone for the first time in a long time. I went to turn on the radio, at least get some music to fill some of the emptiness but found it was broken. Twice I stood up to leave and twice I sat down again.

I turned to the bottle of scotch and started drinking. The more I drank the less I care about being alone. I stripped off my clothes and walked around the cottage naked. It felt really good. I masturbated - something I hadn't done in years. Since Waldo I always had someone to take care of my needs. I actually liked the feeling of my hand manipulating my cock to respond. I wouldn't let myself cum. I kept taking myself to the peak then I'd stop and walk around, drink, eat...I did this until after three in the morning and was drunker than I had been in a long time, when I finally let myself cum. Fuck, I shot a huge load of cum and hungrily licked every drop up. Cum and scotch are great together.

Needless to say the next day I was quite hung over and quite drained. I slept until almost noon. When I woke up I was filled with the desire to feel a man next to me. I thought about calling Shelby, for a brief moment I even considered forgiving him. It was a difficult pill to swallow to admit how addicted to Shelby I was. I decided to get out of the cottage, showered, dressed and went for a walk.

Fresh air, what a novel concept. In the light of day, without the scotch, things were finally getting clearer. I knew that I had to end things with Shelby. The more I walked the more I knew what I needed to do.

I hadn't realized that I had walked so deeply into the woods that I lost my bearings and for a panicked hour I tried to retrace my footsteps. Finally I heard cars and ran towards the sound and found the county road that led to town. I stuck out my thumb to hitch a ride, figuring that once I got to town I could get a taxi or call the caretaker to come get me.

Finally a car zoomed by, slammed on its brakes and backed up and picked me up. The man in the car was only too happy to take me town. It was only a ten minutes ride and when he pulled into the gas station he asked if I would have a late lunch with him. He still had a long drive ahead of him and wanted to eat before hitting the road again. We sat in this dinky little dive place until seven that evening talking about everything and nothing. When we finally couldn't think of any more reasons to stay at the café he volunteered to drive me home. The man admitted to me that he was 'curious' but had never acted on his feelings before. I asked him why he considered doing something with me. All he could say was that I was so open and comfortable with myself that it didn't feel like a decision. It felt like something natural before two people that were attracted to each other.

Bob, that was his name, lived in Boston. He was a professor at Harvard and was on his way back from a conference in New York. He wasn't in a rush to get home to an empty house and decided to take the scenic country roads back to Boston. Bob wasn't at all the typical man I went for. I prefer the physically fit tall well built type. Whereas Bob was the scholarly, bookish type but sometimes that can be sexy and Bob exuded an introspective sexuality that I was drawn to.

Either that or I just didn't want to be alone.

It didn't matter that he wasn't over six feet tall or that he was rail thin I could tell by looking at him that he was going to have a hearty cock and he wanted to play. What more could I ask for?

I invited him to come into the cottage and he accepted. I gave him his first man kiss before we walked through the door and I could tell by the kiss that he was ready for anything. I was in one of my more vanilla moods -- I had woken up wanting to feel a man next me, Bob fit that bill. I didn't want anything but slow passionate lovemaking. I undressed him, kissing and licking every part of his body. He had never felt a mouth on his cock before and that made things even more special for me. I sucked him gently in my mouth, licking my tongue over the head of his cock. I was right about him having a nice cock, it was long and plump and I happily made love to every inch of it. I licked and sucked him until he couldn't take anymore and grabbed my head pushing his cock deeper in mouth as he shot a tasty large load that I eagerly lapped up. His entire body was shaking and he cried tears of joy. Never in his life had he ever felt anything so good.

He wanted to reciprocate and undressed me and tried to repeat what I had done, but he didn't know how to even start. I talked him through it. How to suck me, where to lick me. It was like teaching a child its ABC's. The only problem was that he wasn't doing a good enough job to make me cum. It felt good what he was doing, but he could have done it all night and I wouldn't have cum. He was feeling defeated but I told him to relax, it wasn't important. We lay down on the bed and kissed for a long time. Then I asked him if he would consider letting me make love to him. He was reluctant at first but when I started rubbing my finger to his hole he mewed from the exotic pleasure it brought him and he nodded his head yes.

As strange it this sounds after all the men I've been with I'd never had a virgin ass before. Even Jessie wasn't a virgin when he came to me. I remembered what it was like the first time Waldo took me. It was everything that I wanted it to be, but all my life I wanted to feel a cock in my ass, four hours earlier Bob hadn't even considered being with another man.

I had him get on his hands and knees, knowing that he would enjoy this position the most for his first time. I started using just the tip of my finger rubbing it lightly over his hole until I could tell by his breathing the he was relaxing. I licked my finger and rubbed just a little harder until he opened just a little bit to me. I held it there telling him to relax and let my finger in. It took awhile but eventually I was able to slip my entire finger in him. Bob was a noisy one, letting me know by his loud moans and groans that everything that was happening to him he liked.

I slipped the one finger out and pushed two fingers in him. He liked that even more and was pushing his ass back against my hand. He was relaxed and I knew it was time. I got on my knees behind him and pressed my cock head against his still gaping hole. Bob let out a loud hissing 'yesssssssss' and tried to push back on me, but I held him at bay. I didn't want to fill him too quickly and cause him any pain. I told him in whispered tones that my cock was bigger than my two fingers and that he had to take it slow and steady. And that's just what I did. Like the night before when I kept taking myself to the edge of cumming that was what it felt like going into Bob's ass.

It was torturous going so slowly, the desire to stroke deeply in his ass overwhelmed me at times, but I didn't stray from my unhurried love making. I would slide in a little, and then stop, then go in some more and stop again. My cock was throbbing to cum. Bob was beside himself. He never knew another man could bring so pleasure to him. Finally I was all the way inside of him. I had never felt anything so tight before. Bob was still moaning uncontrollably and even though he wasn't forming words his ass was telling me he wanted more.

"I'm going to pull back and push into you." I said to him. If it's too painful let me know and I'll stop. I pulled half way out and pushed back again. Bob ass was throbbing against mine and I knew he had shot another load.

"More." He said.

I did it again, this time pulling more of my cock and then pushing back in. Again he was throbbing. Was it possible that he was cumming again? I began a long rhythm of strokes, shallow then long, long then shallow. Each time I stopped his ass vibrated against my cock. "More" he repeated with determined insistence.

"Faster?" I asked.

"Yes...please...oh please...more...faster...anyway you want..."

I shot a short load, the pressure releaser, but stayed hard and finally started to fuck him. Bob ass was open and wanted everything I gave it. All he said over and over again was...more... yes...more...yes. I had taken this man to a place he never knew ever existed and he wanted to absorb every second of it.

I felt my second orgasm rising and knew this was the one I had been waiting for. This one was the prize for claiming this perfect ass I was buried in. I reached around to Bob's cock which was still hard and started jerking it hard. He wrapped his hand around mine and together, like a well oil machine I stroked my cock in and out of his ass and his cock until we came together in a one of those perfect, once in a lifetime, moments that makes fucking a man's ass the best and only thing I ever wanted to do in my life.

We collapsed on the bed, spooned together. I was still in his ass and he was lying in his puddle of cum and that's how we fell asleep.

The next morning he was draped over my body still asleep when I woke up. I was able to move from underneath him and make my way to the bathroom. My cock was oddly satisfied, something I hadn't felt in a long time. Bob joined me a moment later and together we let out our morning piss. "Is it proper for me to thank you for last night?" He asked when we sat down over coffee. We were naked and even though my cock wasn't hard Bob's was.