Part 10: Surrogate Girlfriend
Just when I felt sort of settled into a routine, things changed again. This change was precipitated by Tim’s girlfriend breaking up with him. I never found out what happened between them. All I knew was that Tim was suddenly lonely on weekends. Initially, the only effect of this concerned the timing of his blackmail demands. Before long, though, it changed their nature rather dramatically.
I guess the first weekend after Tim’s girlfriend broke up with him, he toughed it out. But on Friday before the second weekend, he had decided that the fact that his girlfriend had dumped him and he couldn’t find another girlfriend was no reason his sex life should have to suffer. Just after I had finished blowing him in the supply room on Friday afternoon, he informed me that I would be coming over to his house Saturday night. When I told him I had a date with Steph Saturday night, he really didn’t care. He gave me two options: break the date or end it early enough to get over to his house by 11:00. Protests were to no effect. He simply reminded me that there would be likely to be *no* further dates with Steph if he had a little chat with her. Now I really wished I had never told him what Steph had said about Tom and Jennifer and my fears of what Steph would do if she ever found out what I was doing with Tim or Murphy. I had told him in the process of pleading with him to keep this secret. But, in my typical naïve fashion, I had only given him more ammunition to use against me.
So my date with Steph had to be a short one. As it turned out, that was fine. A longer date would only have dragged out the torture. We took in an early movie and then went for what I knew had to be a quick drink. I had planned to tell Steph that I wasn’t feeling well and end the date early for that reason. As it turned out, I didn’t have to lie. My stomach hurt and I couldn’t concentrate on anything Steph said. In typical self-obsessed manner, she interpreted it as selfishness on my part and lack of concern about her. In fact, I was very concerned about her and getting sick to my stomach thinking that I would be leaving her to go suck on Tim’s cock.
After I dropped Steph off, I spent the time driving to Tim’s house thinking about how to get out of this hole I’d dug myself into. But short of killing him–which I’d considered but feared I couldn’t get away with–I could think of nothing. So I pulled into Tim’s driveway, prepared for my fate.
I wasn’t prepared for how the night would turn out. After I took care of Tim’s needs in the usual fashion, I was getting ready to leave. Tim told me to stay. I didn’t know what was up until he told me that his girlfriend usually stayed over Saturday night and he was used to having sex first thing Sunday morning. He had missed that last weekend and he didn’t intend to go another Sunday morning without getting his rocks off. What could I do? The blackmail threat was still there. I had to yield.
So I wound up sleeping on the couch until around 8:30 when I was summoned into his room to perform my morning chores. He seemed to enjoy this even more than using me at work. I was so clearly at his beck and call. It was weird for me. He was naked–a first. And he was lying down on his bed–another first. So I got on my hands and knees on the bed next to him. I didn’t have to get him aroused. He was already hard with a morning woody.
I took him in my mouth, knowing my job would be easy this morning because Tim was so hard. Using one hand to squeeze the base of his cock and jerk him into my mouth, I had him ready to spurt in a matter of minutes. And spurt he did. With all the experience I had acquired in the last month sucking Tim off and taking his load, I’d gotten pretty good at swallowing it without gagging or retching. But this morning it was difficult. Whether it was because he had just awoken with a woody and shot me an especially large load or because I was in the unusual position I was in and had to sort of suck his cum up into my mouth to swallow it, I found it hard to keep up with his eruption. Some of it dribbled back down his slick shaft and I had to push it up with my hand and lick it off. When I started to pull off of his spent cock, he pushed my head back on and rolled over, pushing me onto my side next to him with his softening cock still in my mouth. He wanted me to keep sucking him. I’m very different. After I’ve cum, I don’t want any stimulation. My cock is just too sensitive. Tim wasn’t looking for any real action; I could tell that by how he held my head still. He just wanted me to suckle on his soft cock.
While I was pleasing him in this way, I reflected on how much had happened to me recently. I went from not having touched another man’s cock to being available on demand to service not one but two cocks. How many blowjobs had I given in the last six weeks or so? There was no way I could count them from memory. Too many of them blurred together in my mind. But I figured that for the last four weeks, since Tim got istanbul escort into the act, I was giving about 10 to 12 blow jobs a week. And then, there were the three I gave Old Man Murphy before that. I guessed that I had easily given over 50 blowjobs in my short career. I’d gotten pretty proficient at it. And the best part–if there can be a “best part” to this humiliating degradation–was that I was mostly over the shame of shooting my load when I took theirs. That had only happened with Tim five or six times. And it was happening with Murphy less than half the time now. I had learned to carry tissues with me and to wear briefs under my boxers. That way, when it did happen, I could clean up before it soaked through my pants. So, these were the thoughts that went through my head while I suckled on Tim’s soft cock. I realized that I was finding the suckling soothing and comforting. But I found *that* thought very discomforting. So I quickly put it out of my mind. He allowed me to pull off his cock this time and didn’t object to me going.
I spent the rest of the day doing ordinary things: laundry, grocery shopping and stuff like that–things that I used to find boring beyond words but now found comforting in their mundane nature.
Part 11: Taking it Like a Man?
The next week was pretty typical except that Murphy was friskier than usual, demanding late afternoon blow jobs in addition to his regular morning ones on two different days, and Tim began to look for ways to further discomfort me. One time when he knew I was on the phone with Steph, he motioned for me to come with him. When I ignored him, he took the phone from my hand and talked directly to Steph.
“Do you mind if I borrow Jason from you for a few minutes?” He paused while Steph said something I couldn’t hear, and then went on, “I just need him for a while to help me take care of a situation that’s come up. He’s the only one in the whole office who really gets this stuff.” Tim was smirking at me as he talked with Steph. I was desperately trying to figure out whether anything in his tone or words alone would make Steph suspicious about what this “situation” that came up was. I sure hoped not. It was hard enough to patch things up with Steph without any additional problems.
I got through the week okay and I even had a plan to make the weekend go better. I knew Tim had to go up to his parents house Friday night and would be there until the middle of the day on Saturday. So I arranged a date with Steph for Friday night and told her that I’d be working with Tim most of the rest of the weekend on a strategic plan for the sales department.
The date with Steph went well. We spent the night together and everything worked sexually. I was starting to think that I was getting that part of my life back on track. The rest of the weekend would undermine my confidence in that.
Tim wanted me at his house at around 8:00 Saturday night to watch a movie. It turned out that he had two movies–both cheap porno and both with a similar theme. The first was titled *Innocent Bi-standers*. It was about–as much as any of these films are “about” anything–two friends who witness a Mafia hit and are put into the witness protection program until they can testify. They are put up together in a swanky hotel, which lacked for almost nothing. Of course, one of the things that it did lack was women. This absence quickly wore on the two guys and it wasn’t long before they were watching porn together on the TV. This led to whacking off together which quickly led, by a process that wasn’t really made clear, to the more dominant one having the other guy on his knees, servicing him orally. For the rest of the movie, under a blackmail threat, the subservient one was basically a sex slave for the other guy.
The second movie was called *Bi-athletes*. It was nominally about two amateur athletes who began betting on who would win whatever contest they were involved in. The bets were about money (and of course pride) at first. But they escalated into bets that involved the loser having to embarrass himself in some way–usually a way with sexual overtones. Finally, the bet was a blow job and the guy who lost wound up on his knees servicing the winner. There wasn’t any explicit blackmail in this one but the guy who had lost the bet pretty much wound up being the sex toy for the other guy. And the kicker was that he wound up liking it.
Both were portrayed as involving bisexuality but it was really gay porn for “straight” guys who couldn’t quite bring themselves to rent a movie labeled ‘gay’.
Tim and I were slugging back beers throughout the first movie and by the end we were both pretty drunk. During most of the second half of the second movie, Tim had me sucking his cock. But he didn’t want to cum. He would stop me whenever things were moving that way. I didn’t know at this point why.
When the movies were over, Tim asked me what I thought of them.
“I don’t think anything of them, Tim.” I replied, determined esenyurt escort not to reveal anything that might be embarrassing. “Let’s just get this over with.”
“Don’t rush things Jason. Tonight’s going to be a bit different. This is going to be like your maiden voyage. We have to take things slowly.”
I had no idea what Tim had in mind but I had the uncomfortable feeling that it wasn’t going to be anything good for me.
“Stand up.” I followed orders, as I knew I had to. “Now drop your pants and underpants.” So I figured now that he was going for the scene where I give him a blow job while I have my pants down–just like Murphy did once. Tim knew that I was especially humiliated by that and I was surprised now that he hadn’t demanded this earlier. I dropped my pants and underpants to my ankles and felt my cock begin to rise. I’d been hard a good bit of the time while the movies were running, especially when I’d been sucking Tim’s cock. Now my cock was on the rise again. Tim noticed it and commented on it. Then he did something I really didn’t expect. He told me to stroke myself. I hesitated and he told me to quit playing games. He reminded me that I would do whatever he told me to do and I knew it. So I found myself stroking my cock to a fully hard state in front of my colleague.
Tim wasn’t really interested in my cock, though. This was all about domination and humiliation. If it would have been more humiliating for me to scratch my elbow on command, Tim would have ordered that.
I found myself experiencing psychological arousal in addition to my obvious physical arousal. I started to think that I could actually climax like this. The thought of relief beckoned me but the anticipation of further humiliation repelled me at the same time. We would never see which emotion would win out. Tim stopped me well short of shooting.
“Follow me,” he commanded. He walked into the kitchen and I waddled after him my hardon swinging wildly back and forth as I shuffled with my pants around my ankles. He directed me toward the kitchen island and finally pushed me up against it, my crotch pressing into the counter edge. “Grab the other side,” he said as he pushed me down over the island. Taken by surprise, I couldn’t resist going all the way down onto the counter. And, at that point, with his hand on my back, I couldn’t push myself back up. I grabbed the counter edge on the other side of the island and held on.
“And don’t let go.” All I could muster in response was a weak, “no.” My plea went unheeded. I felt my ass cheeks being spread and something very slick being smeared down my crack.
I tried to say ‘no’ much more forcefully but it still came out as a feeble plea.
“Come on, Jason. You know you’ll do what I tell you to do,” Tim said. “So just shut up and take it.”
Tim was right that I would do whatever he told me to. I couldn’t have him tell everyone, including (I was sure) Steph, what I’d been doing. That would ruin my life. Given the choice, I decided ruining my ass was the lesser evil.
So I felt Tim’s cock putting pressure on my anus. I know that some guys–I mean even straight guys–engage in ass play, putting things up their asses or having their partners do that. But I’d never put anything up my ass. For me, that was an “exit only” hole. Now that was all going to change, and in a big way. At first it just felt like pressure against any part of my body would. It didn’t feel as if he would enter me. But then, under gentle but relentless pressure, I felt my asshole trying to open large enough to accommodate Tim’s cock. This wasn’t going to be easy. When the head was just starting to go in, I screamed in pain and tried to pull away.
“Come on, bitch,” Tim spit out. “This isn’t the first time a guy’s taken a hard cock up his ass. Just relax and take it like a man.”
Well, it *was* the first time *this* guy had taken a hard cock up his ass and it hurt like hell. And what was this “take it like a man” shit? The irony of his words wasn’t lost on me. Really, he wanted me to take it like a woman. I mean, I guess gay men take it like this but aren’t they really taking it like a woman? And, anyway, I wasn’t gay.
If he kept pressing in like he started, there was no chance I was going to “take it like a man.” Thank God, Tim relented just a little to let the pain subside. And it did. And then it began again as he pressed hard into me. The head of his cock slid in. I could feel the ridge pass my sphincter.
Tim stopped and just held steady for a few seconds. That gave my ass a chance to adjust to the size. Then, with one hand pressed down on my back, making it impossible for me to move, he gently pulled back completely out of my ass, with the tip of his cock just pressing against my ass. I sighed in relief and, as soon as I did, I worried that he would misinterpret my response. But I think he really didn’t care about my response.
He pressed forward again and this time slipped in more easily. etiler escort Then he began just slipping the helmet of his cock in and out of my ass, which was accommodating him without much pain now. Just when I was adjusting to this humiliating indignity and, to tell the truth, beginning to understand why some men engaged in ass play, Tim moved his hands to my hips. I think I knew what was about to happen, but I still wasn’t ready for it when he thrust into me deeply, rearranging my bowels to fit his cock.
That hurt in a completely different way. The entry had been a sharp pain, which was now dulled considerably. But this was an uncomfortable, almost sick feeling deep in my abdomen. But this, too, subsided–at least the unpleasant parts of it did–and I was soon taking his full thrusts comfortably. And, my cock, which had withered completely after the waddle into the kitchen, was rigid again and pushing up against the kitchen island. It hurt like that so I tried to push back to let it rise above the counter. Unfortunately, Tim misinterpreted this movement. “You like that, don’t you?” He said confidently. I didn’t even try denying it. He was going to interpret things as he wanted, anyway. Raising up to get my cock above the counter made him enter me at a different angle and that path made all the difference. I can’t describe the change in the feeling. Suddenly, I felt the intense urge to cum and so I remained pressed up at about a 45-degree angle while he thrust deeply into my ass. And then, quite suddenly, I felt myself erupting on the cutting board. It was different from any orgasm I’d had before. It didn’t build slowly and get to a sort of staging point from which to launch. Instead, it felt as if was begin expelled from my like a steamroller would squeeze toothpaste from a tube.
Whatever the process, it was incredibly effective at cleaning me out. I spurted over and over, far more than I usually do and covered the cutting board with my jism. I couldn’t believe what had just happened. Tim seemed to enjoy having made me cum by fucking my ass. He let loose with a grunt and filled my previously virgin ass with his cum.
Tim stayed in me for a minute, recovering somewhat. When he pulled out, my ass was so opened up I could feel his cum sliding out my ass and down the insides of my thighs. I felt like a ten-dollar whore (except that I hadn’t gotten ten dollars). “Clean it up with your tongue,” Tim barked at me and I began to gag as I thought about licking his shit-stained cock. But when I looked at him, I realized with relief that he was talking about the cutting board. So, I actually felt like I was getting off easy just licking my own jism up from the counter top.
When I’d finished, which took a bit of time given the quantity of cum, Tim ordered me into the shower to wash him. It was really strange soaping and rinsing off another man. But I appreciated using my hands in the shower instead of my tongue in the kitchen. As I soaped Tim’s cock, I could feel some life returning to it and I wondered what was in store for the rest of the night.
As it turned out, Tim seemed to like corn-holing me. I didn’t give a single blow job–at least not one to completion–that weekend. He fucked my ass two more times though, once as we went to sleep spoon-style and then again in the morning when he put me on my hands and knees, stood next to the bed and fucked me like a bitch in heat. And I came both times. I guess I’m just a sucker for a prostate massage.
I went home mid-morning, with a very sore rectum, and tried to catch up on the things I had to do over the weekend: laundry, dishes and so forth. Tomorrow would begin another work week and I was sure that Murphy and Tim would be making their usual demands. I was getting to the point where I didn’t mind Murphy’s demands. Between the raise in my base salary and the bonuses he was being pretty generous with for my good performance, I was making more money now than ever. I was worried, though, that Tim might want to expand our repertoire at work to include his new-found pleasure of fucking my ass.
Even though I’d cum every time Tim had fucked me, I didn’t like this prospect. Anal sex was messier and harder to hide. I mean, if someone were knocking on the storeroom door when I was giving Tim a blowjob, we could be straightened up and opening the door in seconds–feigning surprise that the door had somehow locked itself when it closed. But if he was deep in my ass when that knock came, it would take way too long to straighten up. Besides, it hurt and I didn’t want to be walking around at work with cum dribbling out of my asshole.
Part 12: More Office Humiliation
I won’t say that I was looking forward to sucking Tim’s cock at work, but I was relieved when it became clear that this was all he was going to make me do. He couldn’t resist, though, needling me about the turn in our relationship. The jabs ranged from public comments that would sound innocent enough to others like, “Move your ass,” to graphic descriptions of our anal sex while I was sucking his cock. I must admit that his dirty talking affected me. I was cumming in my pants almost every time I sucked his dick now. Fortunately, I was wearing multiple layers of underpants and the cum never leaked through my pants.