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An Illicit Affair

Posted by: Age: 99 Posted on: 5 comments
3 likes 29 views Category: Sex Stories General Tags: Secret sex, an affair, terrific masturbation, sucking, fucking,
How a hard cock and a sexy woman can create a lot of grief. 

I was working as jobshopper performing mechanical design duties. A jobshopper is a contract employee who is brought into another company to temporarily help complete a project. I was part of a six man team and another jobshopper, named Bill, was my best friend. We were working on a government contract in a fairly large company with two or three hundred employees. One of the woman working there was a gal named Jill who definitely qualified as the company sexpot. Every guy in the place was hot for her, including me. But I never attempted to make a move on her for a couple of reasons. First, she gave off ice maiden vibes that kept guys away, and secondly, I thought she was out of my league. 

Her best friend was a gal named Liz who just happened to be dating my buddy Bill. Because of this connection I found myself in the occasional company of Bill, Liz and Jill during company break periods. I found that Jill’s ice maiden persona was just an act to keep guys from pestering her. Despite her extremelely sexy appearance (beautiful face and great body) it turned out she was just a regular gal. Very personable, down to earth, and friendly. 

One day Bill approached me and said that he and Liz were going to play hooky from work the following day and if I wanted to join them, Jill would be coming along. Has a cat got an ass? Of course my answer was an enthusiastic, “Yes.” We met up the next morning and spent the entire day together. Late in the afternoon Bill drove us to Liz’s apartment where the two of them went inside, no doubt to fuck, while leaving me and Jill in the car. By then, all the ice had been broken and the two of us knew where things were headed. I had already kissed her a couple of times but alone in the car we took it to the next level. Frankly I was shocked at how quickly things progressed. I had my fingers in her pussy and my cock was exposed but unfortunatly the damn thing did not want to cooperate. At the time I was 32 years old and my dick had never failed to get hard. Ever. But here, with a super sexy gal that I wanted to impress, much less fuck, the damn thing wouldn’t cooperate. I will give her credit. She did everything possible to achieve an erection and nothing worked. She was cool about it, thankfully, but I was still embarrassed and disappointed. I assume that I had put way too much pressure on myself, which can be a recipe for failure. The more you want it to happen, the less likely it is that you will succeed. 

Both Jill and I were married at the time although Bill and Liz were not. So getting together with her again was a challenge, assuming she would even be interested after my failure to perform. But we took a long lunch a couple of days later with the keys to Liz’s apartment and this time, success was at hand. By the time we were inside Jill’s place and even before the first kiss, my dick was as hard as a rock. There was a hunger on the part of us both for some wild and uninhibted fucking. In the limited time we had I did mange to fuck her twice. And this started a torrid affair. 

Over the entire time we carried on, my intial failure to achieve an erection was an ongoing joke between us. Especially considering that during all those months that we hooked up, every time we were together, my dick was fully rock hard before I could even get it out of my pants.  

There was hardly any sex act we didn’t share (except anal). Sometimes if time was tight she would give me a world class handjob. I remember a couple times during break period that we would sneak out to the parking lot to my car where she would jerk me off. I would always ask for a blowjob but she was afraid somebody might see either her bobbing her head up and down or just leaning over into my lap. I never saw anybody in the parking lot but she was just being careful. But the handjobs were highly appreciated. Even when we had plenty of time together she got off on playing with my cock. 

While I could get out in the evenings fairly easily, she couldn’t. I was renting a garage in town where I worked many evenings on my race car. So I had a ready excuse for not being home and there was no way for my wife to contact me at the garage. Jill and I worked out a routine for getting in touch any time she could break free. She would call my home number (this was way before cell phones) and let it ring twice and then hang up. I would tell my wife I suddenly remembered I had something important to do on the race car and drive to the local gas station where Jill would call the pay phone at an outside booth. I think she had to wait something like 10 minutes to call to give me time to get there. Then we would meet somewhere and have sex in the car. However, I was always concerned about fucking more or less in public. Even parking in some out of the way place was always subject to being caught. So I came up with a new scheme.

There was another row of old garages for rent in another part of town.  This was way across town from where my race car was garaged. I rented one of those and because it was winter time and quite cold in the evenings, I came up with the idea of bending the corrugated sheet metal siding on the back of the garage to allow me to snake a flexible hose to the outside of the garage. I would meet Jill, park her car, and then we would drive to garage in my car. I would back in and then get out and slide the hose over my exhaust pipe. Then I could leave the motor running with the heater on without fear of asphyxiation. We spent many evenings fucking and sucking our brains out in that garage. It was thankfully in a remote location and nobody ever came by there at night to hear my car running. The garage backed up to a wooded area so there was no one to see my exhaust. 

I remember one particular session. We always used condoms because she was deathly afraid of getting knocked up. One night we were all set up in the garage ready to fuck, but no condoms. I didn’t want to go through all the bullshit of taking the car out and  having to rig it back up. I knew of a drug store that was a few blocks away so I exited the garage and ran like hell to the drugstore. I really wasn’t dressed for as cold as it was. I bought a pack of condoms and ran my ragged ass back to the garage. It took me a while to get my breath, get warm, and rest up after all that exertion just to turn around and wear myself out all over again. But it was worth it. Jill was a terrific sex partner.

My wife and I hosted frequent parties at our house and on one of them I invited Jill and her husband. I knew her husband because we were in the same class in high school although we moved in different circles. It was a crazy thing to do but both of us wanted to at least be around each other as much as possible. It was a real challenge to be so close to her but act normally. The party thing led to my wife and I and Jill and her husband going out for dinner one night. This was a very memorable outing because at some point Jill slipped off her shoe and proceeded to massage my cock with her toes under the table. This was totally unexpected because it was frankly out of character for her. After enjoying it long enough to get an erection, I shook my head at her because it was just too damn risky.

Then the shit hit the fan. We had been sneaking around for several months with sessions during lunch at Liz’s house happening one or two times a week. Bill wasn’t involved on this particular day but the three of us went to Liz’s place and she said she had shopping to do and left us alone. We immediately got busy with an extremely intense fuck and suck session. As we were cleaning up, Liz came back. Just a few minutes later there was a knock on her door. Jill and I ran back into the bedroom only to hear Liz talking to Jill’s husband. He had been getting suspicious and drove by Liz’s place and saw Jill’s car. We heard them talking for a bit and then the door closed. Jill and I assumed he had left but what actually happened was he had been talking to Liz in the doorway and then came inside and the door closed. Jill and I walked out of the bedroom together and he went ballistic. He literally screamed, “Are you fucking my wife?” Liz, to her everlasting credit, immediately jumped into the conversation and told him that she was the one having an affair with me. She came up with a credible story that we had to keep it on the downlow because I was married. Anyway, he bought it, but only because he had to, mainly to save face and to avoid a possible physical altercation. I don’t think he believed it for one second.  

Anyway, that put a real crimp in our activities. By now my wife was thinking something was up as well. Jill moved out and took an apartment that was actually quite close to where I lived. She felt strongly that we had to stop seeing each other because the stress was causing her to lose her hair. It wasn’t noticeable to anyone but her but it was serious problem. 

I attempted to stop by her apartment a couple of times but I spotted her husband’s car parked outside keeping watch. I guess to see if I turned up. My work at the facility had ended and I no longer had any way to talk to her. Even to find out if she had a phone. I got so desperate to talk to her that one night I parked near her apartment where her husband was keeping watch. When he finally left about 11:30 pm, I followed him all the way back to his house and then drove back to her apartment. A round trip of nearly an hour. I woke her up and we talked. No sex. I finally agreed that it would be best to end it. Coincidentally, my wife somehow found out where Jill was living and my wife’s brother spotted me leaving Jill’s parking lot. My wife had suspicions of what was going on but that was the closest thing she ever had to any proof. 

My marriage ended shortly after that but not because of Jill. It had run out steam a couple of years earlier and was doomed to failure anyway. 

About four years later, after I had quit my job and started a new business that was an overnight success, I stopped off at a facility to see about buying a very expensive piece of equipment for my new business. I had an appointment with the owner and I walked into the lobby and there was Jill at the receptionist’s desk. She looked as good as ever. It was our first contact of any kind after that night in her apartment. She was now divorced and seemed to be very happy. I asked her out to dinner. I don’t think I really had any intentions about starting something up again. I was already in a committed relationship with a woman who would become my second wife. But I was curious to catch up and see if the old spark was still there.

It wasn’t. We kissed a bit but I think it was obvious to both of us that what’s past was past. I got the impression she was a bit intimidated by me. I think my obvious success after those four years changed me in her eyes somehow. I thought of myself as basically the same person but I think the new Cadillac El Dorado I was driving and the super pricey piece of equipment I was buying from the company she worked for somehow made her put me in a different category from the person she knew four years ago. I was a bit disappointed that whatever spark that had existed was gone but also relieved that it was now history and wouldn’t complicate my life. 

I guess it is somewhat unfortunate that illicit sex can be so much more exciting than regular sex with a partner. The thrill of doing something you shouldn’t be doing along with the ever present danger of getting caught, somehow makes is so much damn fun. 

I didn’t have any regrets about the time our affair lasted other than it heavily contributed to the end of her marriage. Although I suspect if it hadn’t been me, it would have been somebody else. None of my friends, other than Bill, even knew that I had an affair going, so it was never any kind of public embarrassment for my wife. But she had a big mouth so I suspect her suspicions were relayed to all of her friends. I used to joke that the checkout person at the local grocery store probaby knew everything that was going on in our marriage. 

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