That Asshole


Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Cheating, Voyeurism, .

Desc: Sex Story: While doing my so-called friend Doug the favor of watching his dog while he is a way on vacation I find that he video taped my wife having sex. And that is only the beginning of the problems cause by 'That Asshole.'

I was sitting at the bar in a restaurant called Marty's in one of the many suburbs of Chicago waiting for my date, actually a blind date set up for me by a friend at work. I got there forty-five minutes early because it would have been too far to drive home to my apartment and be able to get back in time to meet my date. Another reason I was so early was that it had been years since I had been on a regular date let alone a blind date and I was a bit nervous. I wanted to have a couple of drinks to settle my nerves before my date showed up. Carla, my friend from work, gave me a brief description of my date and said I shouldn't have any trouble recognizing her. All I really got from the description was her name Mary and that she is supposed to be very attractive.

I really hated the idea of a blind date but Carla would not be talked out of fixing me up and I knew that it would probably be a long time before I got up the nerve to start asking women for dates again. It had been two months since my wife and I split up and Carla insisted it was time for me to get back in the game and I finally gave in to her.

As I sat sipping my second scotch of the evening I saw Pam come into the restaurant and sit on one of the benches in the waiting area. Her being there was going to be a problem. You see, Pam is my wife. Although we have been separated for the last two months we are still married.

Pam and I had been married for twelve years when we separated. During most of that time we had a great marriage. Our problems started about two years ago, when for some reason we just suddenly stopped talking to each other. At the time I didn't know why and I didn't know which of us started it. After a while the silence when we were together got so uncomfortable that we started avoiding each other around the house. This situation lasted for about two months and ended one night after we had been to a party. At the party I had had quite a bit to drink and as it turned out so did Pam. We were both feeling pretty good when we got home and we ended up making love. The next morning the tension was gone and we began talking to each other again.

After that things nearly got back to normal. The only thing that didn't seem to fully recover from that rough period was our sex life. We went from having sex at least twice a week to only two or three times a month. Our life continued like this for the next two years. That's when my friend Doug asked me to watch his dog for him.

Doug and I had been friends since high school and I was probably his only good friend. Doug was a very difficult person to like. He is so full of himself. Ever since I've know him he has bragged about the women he has dated and bedded, which was okay when he was twenty, but he is 36 now. He believes that most women are attracted to him when in fact most women I know think he is obnoxious.

The guys all think he is just an asshole. I guess the one character flaw that turned people off the most was the fact that Doug bragged about being a voyeur. This started in high school when Doug would sneak out behind the girl's sorority houses and peek in windows. We loved to hear his stories then but he didn't stop that kind of behavior after high school. I remember when we were about 22 years old, a bunch of us were out drinking and Doug told us that he had a collection of pictures he had taken of unsuspecting women in compromising positions. He said, "If you always have your camera with you and are ready you can get some great pictures."

Nobody really believed him but they resented him for thinking that this of behavior would be acceptable. Gradually most people started to avoid him and began to refer to him as "That Asshole."

I remained his friend, not by choice but because I didn't have the heart to turn my back on him. He had always been there for me and had helped me on many occasions. When Pam and I first got married Doug helped us move into our first apartment and then when I bought our house from a guy who was building it himself and ran out of money, Doug helped me finish the house. The exterior of the house had been finished and the plumbing and electrical had been done but the interior walls were not finished. They needed sanding and painting and the trim work had to be done as well as hanging the kitchen cabinets. Doug helped me do all of that work and asked only that I have a cooler of cold beer handy while we worked. I would go over to the house every night after work for three or four hours and often would find Doug already there working. When we finished the house Doug helped us move in. I just couldn't turn your back on him even if he was an asshole.

Doug and I would go out drinking together whenever Pam had a committee meeting for one of the charities she for which she did volunteered work. About five years ago Doug suggested that we go out, pick up a couple of girls and get laid. I told him no. I wasn't going to cheat on Pam. After that night he would bring this up almost every time we went out. I began to think it was just a joke to him. Then about two years ago as we were sitting in a bar when Doug said, "Look what just came in the door."

I looked over to see two women standing in the entrance to the bar. One was blonde the other a redhead. Doug said, "How would you like to get a piece of that?"

I admitted that they were attractive and that it might be fun to get them into bed. Then before I could say another word Doug was waving to the two women and they started coming over to our table. I said, "What are you doing?"

Doug said, "I am doing you a favor. Getting into a redhead every once in a while is good for you."

I didn't have a chance to say anything more because the women had already arrived at our table. The blonde kissed Doug then Doug said, "Ken meet Kim and Brenda." Kim was the blonde and Brenda the redhead.

I was uncomfortable for a little while but Brenda was easy to talk to and after a couple more drinks I relaxed. After a couple rounds of drinks Kim suggested that we all go over to her place. It turned out that Kim and Brenda were roommates and they shared a very nice two bedroom apartment. When we got there Kim and Brenda fixed drinks for everyone and we settled in front of the television. After a while I was talking to Brenda about something and suddenly realized that Doug and Kim were gone. When I looked around for them Brenda said, "If you're looking for Doug, he and Kim went into the bedroom."

When I turned to look at Brenda she kissed me. I knew I should leave right then but I didn't move. Then Brenda said, "Would you like to see my room?"

I knew it was definitely time to leave as Brenda led me by the hand into her room. I was searching for the words to explain that I had to go home as Brenda kissed me again and flicked her tongue across my lips. I immediately felt myself becoming aroused and when she kissed me again it was all over. I kissed her back and we dropped down onto the bed. Part of my mind kept telling me to get out of there and go home but the powerful little brain in my little head told me I needed a redhead.

I pulled Brenda's top off and soon had her soft breasts in my hands and mouth. As I sucked on her nipples, Brenda made little mewing sounds in her throat. As her breathing intensified I started to open her pants. Brenda helped me get her pants off leaving her on the bed in just her black panties. I kissed my way up her inner thighs until I reached her panties then I pulled the gusset aside to discover that Brenda was a natural redhead. She had a large triangle of soft fluffy red hair. I pressed my face into her hair and inhaled her scent. I ran my tongue over her vulva causing Brenda's hips to jump just a little. As I began to probe Brenda's pussy with my tongue she took my head in her hands and pulled me tighter against her. I wasn't sure if she was having an orgasm or not because Brenda didn't make any noises but she was humping my mouth and her juices seemed to be flowing heavily.

I work her pussy over so hard that my mouth actually got tired, and then I got up and removed my clothes. As I came back to the bed, Brenda took my cock in her hand and pulled it toward her face. I move in the direction she was pulling, like I had a choice, and Brenda took me into her mouth. I stood there looking down on her red hair as she worked my cock in and out of her mouth and I momentarily thought of Pam and felt a pang of guilt but then I look at the downy red hair between Brenda's legs and all I wanted to do was get my cock inside her.

I climbed onto the bed and began kissing Brenda as my cock searched for her opening. It didn't take long for me to find her warm wet hole and slid my cock deep inside her. We bounced around the bed, slowing and then speeding up, trying to prolong the pleasure as long as we could until I finally exploded inside Brenda's pussy, spewing my seed deep inside her.

Afterward I felt great for about five minutes, and then the guilt started. I didn't want to be an asshole and just get up and leave but all I wanted to do was get out of there. I stay for half an hour then said that I had to leave. Brenda didn't seem to be upset. She walked me to the door and said, "Let me know if you want to get together again." Then she kissed me and I left. Apparently Doug and Kim were still going at it in the other room when I left.

Looking back on it now, I suppose that my guilt from that affair was one of the reasons that I found it difficult to talk to Pam during that two-month period of time because that is about the time the problem started.

After that Doug would occasionally bring up my night with Brenda and ask if I wanted to do it again. I gave him an emphatic no. I told him I wasn't going to cheat on Pam again.

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Story tagged with:
Ma/Fa / Consensual / Cheating / Voyeurism /