It Hurts When Its Over

I noticed Deb soon after I took my new assignment in the office at the gold smelter. She is easy to notice, because not only was she very pretty, she is a full head taller than the average woman in that building and has a slender body like a fashion model.

Perhaps it was jealousy, but soon after a management change, Deb's position of authority over the secretarial pool was challenged by the two women who were sent from the home office a hundred miles away, and although her performance was steady and her work was predictably well done, she found herself answering numerous questions about why the procedures in the local office weren't consistent with those used in the home office—which, by the way, didn't face the same sort of day-to-day problems because the clientele served there were primarily with retail customers while the local office handled wholesale deliveries.

Within a few weeks of taking notice of her I found that Deb was sometimes in my office twice a week asking for advice about how to handle the odd circumstance she was facing, and although I tried to help by explaining how I handled my own issues with the new management team, I was sure I wasn't giving her much help because the things that were happening to her were far different than my problems and hers appeared to be violations of the state employment laws and an attorney might have been better able to construct a permanent solution for her than I.

Still, I felt good about being a receptive ear to her problems and helping her find solutions to the nightmare that the management had laid on her. There was a sort of protective feeling that came over me when I thought about how she was getting the shaft. I'm not wired to deal with injustice without reacting.

During my conversations with her I discovered that I was developing an attraction to her because of her warm smile and her easygoing way that was always pointed at making the people around her feel at ease. Deb would often joke with me and others in the office, and I found that we were soon able to feed off each other's sense of humor. It was clear to me that she enjoyed that as much as I.

I felt odd about the connection I was making with her because I was careful to go home to my wife, Brandy, every evening and loved her very much. Nevertheless, I had found that most of the time my wife was rejecting my amorous advances and I had a tremendous unmet need that I hardly acknowledged to even myself. I should have known that by befriending Deb I was placing myself in a situation that I wouldn't be able to stop before it got out of hand, and if it did, we'd both be in for possible job termination.

I told Deb during one conversation in my office that although my situation at work was nearly as bad as hers I had a peaceful home to go to after work every day, and although I looked forward to going home every day because I loved Brandy very much, I was terribly frustrated sexually. Deb responded that her life was bad at home, too, and confrontational with her husband who had no concern for meeting her needs and only had sex with her so as to use her to gratify himself with no concern about giving her the pleasure during the once-a-quarter event. She was half-ashamed of the confession and we both made a small joke about it.

In the same "innocent" and joking manner that we had treated everything else we talked about, I told Deb that it was so bad for me that I found myself masturbating several times every day when I was alone, and Deb confessed to me that she was also having to satisfy her own needs alone. Soon thereafter, I told her that I was thinking about her when I masturbated, and was having sex with her in my mind. When I was telling her about the thoughts I was having when I climaxed, although she didn't respond in kind, I could tell that she was telling me by her look that she was thinking of me when she was climaxing, too. It was during those times that I started thinking about what it would be like to have an affair with her.

A few months later, I quit the job and took up a job doing consulting work for other smelting companies, and she quit her job, too. The intimate day-to-day contact at work was now over as was the potential of having an affair discovered by our workmates if we were to have started one.

My consulting work gave me a lot of time alone while I worked from my home office trying to line up the next consulting contract. I didn't forget Deb, though, and had kept her home telephone number and e-mail address so as to not lose track of her. I was surprised at myself that I had kept the thought of being with Deb in the back of my mind even after we no longer worked together.

For a few months I kept up a stream of innocuous-sounding e-mails to Deb and tried to think of ways to see if she might now be receptive to my sexual advances and worked out in my mind how I might seduce her via e-mail and telephone. I determined the best way to test her would be to tell her that I had been entertaining myself writing pornography for myself. She bit and asked me to send her one. I sent her one within the next few days.

What I sent her was more romantic than physical, and the story line put Deb in her home office alone when her husband was away at work for the day. The plot line was plausible enough because it had me stopping over to help her with a computer problem and when I got inside the house, I went to her and was kissing her on the neck and rubbing her shoulders while I looked down and tried to get an idea of what her breasts and nipples were doing as I looked at the mounds and points moving under her blouse as I massaged her shoulders. Of course, I wrote about getting a hardon while I touched her shoulders, which was a true-to-life reaction when I saw her or talked with her. I wrote of how after she would leave my office after a talk with me, I had to stay in my office seated behind my desk so that nobody in the office would see when I stood up that my cock was hard and holding my pants out like a tent pole.

Since I was still a bit uncertain about what she might be feeling I was glad when she told me that she liked what I was writing, but wanted to read something a bit more explicit. That was all it took, and I next wrote of meeting her at a second house she owned and spending enough time together to be able to do a full job of making love together. We were both thinking that actually having sex together wasn't something that we (two married people) could actually do despite the strong attraction. We discussed how our home situations were very similar and that they needed to both be discreet if anything serious developed so as to not hurt their spouses if it were discovered that we had started making love together.

We soon met for lunch, and although we were both tempted to let the attraction be fulfilled that afternoon, we kissed good bye gently and drove away separately, still honoring an agreement between us to "be good." Driving away from that lunch date was one of the hardest things I have ever done, and the hour-long drive home was painful as my stiff cock strained to be allowed to be straight, but the fabric of my pants kept it painfully twisted against my left leg and put a crushing pressure on my left nut.

When I got home nobody was there, and I was able to relieve the pressure inside my pelvis that was shrieking to be released. My mind, of course, as I jerked and throbbed, went to looking at Deb, imagining her nude body under me as I looked down and saw myself plunging inside her and her face reflecting the pleasure of what I was doing to her. When I climaxed, in my thoughts I was flooding semen into her, and was glancing first at her pretty face and then down at the physical connection I had established inside her. It only took a minute to cum, and the excitement of the mental picture caused me to have powerful throbs of pleasure and strong contractions in my pelvis that caused my semen to shoot out away from my body about 3 feet. In my mind she was cumming at the same time and I was stimulated to a more powerful orgasm by mentally imagining I was feeling the intensity of the pleasure she would be getting, too.

It was several weeks later that while returning from a consulting job at a shop near the mining district in the state, I stopped off at her new office where she worked for her husband as an office supervisor. I found her typing data into her desktop computer, and leaned in to answer some questions she had about internet e-mail files being read by the company I.T. people. I said it would be best that she not open any of the seducing e-mails I'd sent her at work or any of her encouraging replies to me (just to be safe,) and not to download on that computer any of the files I'd sent to her, either.

I was in my suit and tie since I was finishing my consulting work for the day, and as I looked at her sitting there a dangerous idea came over me. Putting my back to the office window next to the door that opened to the hallway I reached down and fished out my hard cock and touched it to her fashion-model slim upper arm. Since I, at 5'6", am about 3 inches shorter than she,I figured this was an opportunity that she could see for herself that my 6" cock was as big, as thick and long, as most men who were physically taller, and so that she'd have a chance right in her office to know that I was physically equipped to fill her up when we finally made love. I put my cock away quickly and not a minute too soon because her husband, Edvard, came into the office and asked to be introduced. I told him that I was a consultant and friend of Deb who had helped her with computer problems in the past and had stopped by to see if he could help her with one she was having that day.

As Evard and I chatted, I was still amazed that I had such boldness to flash Deb in a public place, but I found that doing it there was more exciting because of the risks of getting caught. I also had a smug feeling of superiority over Edvard knowing that I was stealing Deb's affection from him. That visit to her office caused me to fantasize about being with her in her office as she sat on the edge of her desk and took my cock inside her and then looked at Edvard through the window out in the hall giving him her "I'm cumming and it feels good" smile as I pump her and look at Edvard's frustration. It was an interesting fantasy to me that I didn't fully understand and I didn't think could ever be realized, but the feeling was one of superiority thinking about topping a man who should have been taking better care of business with his pretty wife.

Within another couple of months, Deb reported that her second house was now empty of renters and she planned to move in there. Both Deb and I knew that this change in circumstances would put us at an even greater risk of breaking their pledge to be good and would likely lead to a lovemaking session which was something that could not be undone once it had happened. I can remember closing a few e-mails with "Fuck me! Fuck me!" She responded a couple times, "We WILL, soon. I can't wait to have you inside me."

It did happen. One night I knew Deb would be at home and was I was thinking during the whole hour it took to get to her house about finally burying myself inside her and then not moving a muscle as we felt each other's bodies fully connecting and looked into each other's eyes. I knew that I'd not be able to hold still like that for very long, and I soon discovered that neither could she.

When I got there I found that she was in a green dress with a relatively short hemline. As I closed the front door behind us I moved close to her and kissed her in the entryway. The kiss caused the organs inside my pelvis to contract on the seminal fluids and give me a hot flash of a low-grade orgasm that intensified as I kissed her even though I hadn't touched my cock to her or touched it myself. I could tell that the knob of my cock was flushed and hot, perhaps about like a fever I remembered from childhood. It seemed a waste to not give her a sense of how hot that knob was so I unzipped my pants and directed it toward her upper thigh. Because I am 3" shorter than she, I found that I was not able to put it straight-ahead and level directly on her panties over her clit as I had hoped to do. I discovered that she wore no panties, and that my cock, when angled at the normal 45 degrees when freestanding and hard, was long enough to reach her clit even when her taller stature lifted her groin several inches above mine. I gripped my cock near the base and without rubbing any long distances, vibrated my knob against her hot button. She told me that she was almost starting to cum and asked me if I'd prefer to get naked and get into bed.

When I got into bed with her I studied her breasts carefully. Despite her slender model-type frame she had beautifully formed and moderate-sized breast mounds with gumdrop-sized nipples that I knew held concentrations of nerve bundles that would react if I were to alternate taking them into my mouth and sucking on them. I did that, and I could feel her pressing her body up to me so that her clit was pressed against my lower chest and abdomen. While I sucked, although I wasn't giving my shaft any direct stimulation, her gasping moans of pleasure and the gentle thrusting of her pelvis up into my chest was increasing my arousal to almost a breaking point.

I stopped sucking and adjusted my position between her thighs so that i could put my cock back on her clit, and as soon as I had it in the vee at the top of her slit she gripped it near the base herself and stimulated her clit with the tip of my cock. I could tell that she was starting to cum because I could see the pleasure smile on her face, the low moans she was making and the way she pulled her clit hood up over its sensitive tip and the way her pelvis reacted by soft and short thrusts. Before either of us was aware it had happened, my thick cock slipped down lower between her inner lips and the top 3" was sliding inside her. Her slippery juices coated me and even with only the first half inside her I found that she was giving me more pleasure than I could remember. We both finished cumming within only a couple minutes, and both of us agreed that they were probably too hot for each other. She was so tight that the slippery folds inside her seemed to cling to me as if there were a vacuum developed between us to hold us together. It is true that a small man sometimes has a big cock. Or, as I told her my grandpa used to say, "Big man—big cock. Little man, all cock." Call me Mr. Allcock.

Afterward we talked about the guilt, and I said that I wasn't sure I could deal with it indefinitely. Deb said that she felt guilty, too, but was more concerned about us hurting our spouses than the actual guilt of sex with me. I said that I worried that when the guilt overcame me that I would likely have to end the affair. I told her that my main concern about that was that she'd feel emotional pain when that happened and that would be more a cause of pain for me than the separation itself.

I went home feeling relief from sexual tensions and an expanded sense of wanting to protect Deb from the bad things she'd been experiencing at work and at home. I also had an overwhelming feeling of guilt about hurting Brandy if she were to discover what we had done. Nevertheless, the emotional gratification of being with a beautiful woman like Deb and the pleasure I knew I was giving her when coupled to the strong pleasures she gave me drew him back like a powerful magnet.

Since I learned I couldn't get it all inside her I half paid attention to something I don't usually notice the next night, namely, a woman on a cable talk show. She mentioned Astroglide—a product that would let you "park a Cadillac in a doghouse." Next time I would park my Caddy.

The next time I showed up at her house I stopped off with a one-ounce bottle of that slippery and a vibrator for her to use when I couldn't be around to help her get her cum. We both disrobed and immediately went to bed and began making love by kissing and touching each other so as to build up our arousal as we lay on our sides facing each other. Deb put her leg atop my hip so that the lips of her slit were laid open to be touched by my cock, and I gripped the cockshaft again and began vibrating her clit as I had done before when we were standing in the entry way. She only took a few seconds of that, rolled onto her back and opened her thighs so that I could place myself between them.

As soon as I was mounted and holding my weight off her with my knees she took hold of my cock, said, "I want to play first," and began stroking her clit shaft by using the cock knob to flick the hood of her clit over the tip of it. I immediately noticed that the motions she was making were the same ones that I made when I was jerking my cock when I got to the place where I was about to have my cum while masturbating. Having a sense of what she was feeling made me even hornier, and I could feel that my knob was swollen to its absolute maximum size—the size it swells to when it is shooting cum—and the thoughts of what she was feeling were contagious even though I wasn't yet ready to stick myself into her.

I was surprised to see how short a time it took for me to be ready to put it in her, and I reached up to the headboard to get the lubricant that would let me all the way inside her and rubbed a bit of it on the knob and shaft before getting back into place and fucking the cock inside her in a single stroke all the way to my balls. Both of us gasped and moaned as the feeling of that first moment of full connection flooded through us and urged us to start cumming right NOW!. The thickness of the shaft caused the base of it to stroke her clit every time I withdrew. I left it inside all the way as long as I could, then withdrew only an inch or so before reinserting to the full connection. Every time I withdrew I could feel the throbs of pleasure building inside, and it was an automatic reaction to push it inside as far as possible so that I'd be ready to withdraw it and get that cum pulse again. Feeling myself nearly all the way inside her even when I withdrew was an extraordinarily good feeling of connection with her.

The slow and short pumps couldn't be sustained, of course, and soon I was pulling almost all the way out and all the way back in at a quick pace that caused us both to be overstimulated. I looked down, and Deb was smiling up at me. It was the satisfied smile that she gave me every time I was helping her cum hard. Her moans of pleasure matched my outstroke, and I knew that she was getting exactly the same feeling as I from my thrusting.

It happened a bit later that Deb changed jobs and started working at a theme park which was a welcome break for her from the office politics that she'd learned to hate over the years. Soon thereafter I told her that I wasn't man enough to keep seeing her platonically because I'd not be able to stop myself from wanting to fuck her again and start the guilt loop all over. She didn't really understand, and hoped to keep a friendly and implicitly platonic relationship, but I still insisted that I wasn't strong enough to resist her.

The final breakup came about six months later when I suggested that we meet in a public place, like a golf course, but then I said that being with her would be a temptation that I'd not be able to overcome and since I had said before if we did it again that the guilt would be too much she said, "We will never have sex again."

She meant it to ease my mind about not being able to stand the temptation and resultant guilt, but I took it as a rejection and discovered that my concerns about her getting hurt emotions when it was over were misplaced and that I was the one who had the hurt feelings. I tried to explain that I was taking the blame but I was wrong about being the one who would be hurt by the breakup instead of her as I had at first thought.