I told this to a friend of mine and he suggested I write it down and submit it to Literotica. This story and all my stories are true with names changed to protect those involved. I have been fortunate to have accumulated a few worthwhile experiences over the years and hope the readers have nearly as much fun reading them as I had participating. Comments are welcome. All persons involved were 18 years old or older.
This is the true story of my first and arguably most erotic liaison which occurred in 1982. I grew up in a large southern city in an upper middle class neighborhood. Most of the mothers did not work and spent most of their mornings playing tennis or doing some sort of volunteer work. Afternoons consisted of carpools and sports practices.
In my junior year of high school our cozy neighborhood was rocked by scandal involving my neighbors (the Westons) who lived directly across the street from my house. It seems Mr. Weston was carrying on a long standing affair with a married woman who lived a few streets behind us. The fall out was as expected. His wife threw him out as the sordid details trickled out about Mr. Weston's transgressions. The Westons had two kids. Tim was a year younger than me and was thankfully at boarding school in Virgnia when the scandal broke, and Ellie was 8 years old and blissfully unaware of the details.
Mrs. Weston was an attractive woman in her early 40s. Her friends called her Chris (short for Christine) and she was an excellent and very competitive tennis player. I spent many a day hanging out with her son over the years and watching her move around the house in her tennis skirts. She had great legs that were always tanned and muscular. While she was not stunningly beautiful she had a great body and a cute round face.
She did not respond well to the affair and losing her husband. She was understandably angry and bitter. Her perfect little life had been torn apart and her husband continued to see his new partner and was very open with their relationship. He ended up marrying the woman as soon as his divorce from Mrs. Weston was final. I never understood how he could leave a woman as attractive as his wife for the frumpy thing he dumped her for.
Prior to the Weston's split I spent plenty of evenings baby sitting for their daughter and I got more opportunities after their separation. I was on call for sitting duties for everything from grocery store runs to evenings out. Mrs. Weston treated me well but I could see she was not a happy person and she lived with a glass of wine in her hand. Things changed in the fall of my senior year when she began seeing a guy. I thought he was a jackass from the first time I met him. He was at least 5 years older than Mrs. Weston and also divorced. Most guys have the ability to spot a snake and I was sure he did not have the long term well being of Mrs. Weston in mind. She seemed happy however and they went out several times a week. That turned out to be good money for me. It was not long before I started seeing his car still at her house in the morning when her husband was taking care of their daughter.
Events took an unusual twist just before Thanksgiving when Mrs. Weston and her new boyfriend decided to have a dinner party for a few other couples. Most of the guests were friends of his. I was asked to sit for her daughter for the evening which amounted to spending the afternoon keeping her entertained while Mrs. Weston prepared for the dinner. I was supposed to watch TV with Ellie in the upstairs playroom during the party. Things were frantic before the party. Mrs. Weston was bouncing back and forth between the kitchen and her bedroom as she tried to get the dinner and herself ready. She was also barking orders at me to move chairs, sweep the steps, and most anything else that needed doing. Little did I know that one such chore was about to turn into the most erotic experience of my 19 year old life.
Mrs. Weston screamed down the stairs for me to brush their dog Bruno. Bruno was a white Peek-a-Poo whose long hair would pick up burrs causing matting around his stomach. About the only time the dog looked presentable was right after a bath. He looked like a dirty mop that day. I did my best to brush out the matted hair but Bruno would have none of it. Bruno and I did not get along on the best of days and he turned ferocious when I tried to flip him on his back and brush out the burrs. Mrs. Weston who was approaching pure panic as the clock ticked down to the arrival of her guests screamed down for me to bring the dog and the brush upstairs to her. I picked up Bruno and raced upstairs to find Mrs. Weston putting on her make up in her bathroom and wearing a knee length blue bathrobe. She told me to hold Bruno and she would brush him. I knelt down on the bathroom floor and she knelt across from me and frantically started brushing the struggling Bruno. Almost immediately she reached behind her and grabbed a foot stool to sit on. In doing so she assumed a squatting position in order to lean down and brush the dog. Her bathrobe fell open in the front and I found myself a mere 18 inches from the most alluring sight I had ever beheld. She was wearing a pair of white silk panties that were just skimpy enough to allow me to see the outline of her dark bush underneath. As always, I was wearing a baseball cap which allowed me to stare straight at her crotch while appearing to be heads down on the dog. For a solid two minutes she raked the brush over Bruno while I was locked in on her panties, her shifts and movements only heightening my arousal. Then it was over. She stood up and barked another order and I grabbed Bruno and hurried out of the bathroom. For those who do not understand the desires of a 19 year old young man you may not understand but over the years I have probably reflected more on this incident than any other in my experiences. Luckily for me, it was just a prelude for more.
The party went off without a hitch. After Ellie went to bed I settled back in front of the playroom TV and the last thing I remember before falling asleep was watching Saturday Night Live. My best laid plans to leave during the party to avoid any clean up duties were dashed. I did not like being around Mrs. Weston's boyfriend (Mr. Shive). I awoke to an argument. The guests had left and Mrs. Weston and her boyfriend were going after each other. I could not make out much of what she was saying but he was accusing her of drinking too much. He said that she had embarrassed him which sent her into a holy tirade. She was certainly too drunk from what I could hear and I quickly moved down the side stairs that led to the garage and got the hell out of there. Things must have calmed down at some point because his car was still there the next morning. The following afternoon Mrs. Weston called and asked me to come by and get my money. She could not hide her hangover and looked terrible when I came over.
Over the next several weeks I continued to sit for Mrs. Weston and on every occasion she would come home completely blitzed with Mr. Shive. He would usually pay me and I could tell from his mannerisms that he loved the fact that when I walked out the door he was going to do whatever he wanted to Mrs. Weston. I could tell he did not respect her by the way he talked to her.
Sometime around Christmas, Mrs. Weston called and asked me to baby sit for her the following Thursday night and I agreed. I had been hanging out with her son on Christmas break but he and his father were heading for Colorado for a week long ski trip. Mr. Weston's girlfriend was going and Tim told me his Mom was furious about it. She and Tim were not getting along and Tim was spending most of his time with his Dad.
I realized a couple of days prior that my baby sitting gig was on New Year's Eve. I felt tricked that Mrs. Weston had not specified that Thursday was New Year's Eve. I held a little pity party for myself after her and Mr. Shive left the house. Something was clearly wrong between them as they were very short with each other and appeared to be angry. I settled in to watch the BlueBonnet Bowl and wondered how much fun my friends were having at their New Year's Eve party.
Once Ellie was in bed I grabbed a bottle of Jack Daniels from the Weston's liquor cabinet and took a couple of shots. I was pissed to be sitting on New Year's Eve while all my buddies were getting rowdy. I was supposed to join them later at a field party after Mrs. Weston got home so I figured I should get started myself. I mixed up a stiff bourbon and coke and sat back down on the couch.
Before I knew what was going on Mrs. Weston barreled in through the side door and slammed it so hard it is a wonder the window panes did not shatter. She was crying hysterically to the point she could barely catch her breath. I did not know what to do other than move into the kitchen to see if she was alright. When I asked, she blew up in a drunk and tearful tirade about her cheating husband, her cheating boyfriend, and her miserable life. She went on and on about how her husband had turned her son against her and how Shive was a manipulative womanizer. She said he was hitting up every woman at the party and she knew he was seeing other women. She ended it by screaming out "Happy New Years Fucking Eve". Needless to say, I was stunned into silence. I told her to go sit on the couch and I would get her a glass of water. Surprisingly, she went and sat down and I brought her the water. When I came back she was staring at the bottle of Jack that I left on the table and she said, "I see you made yourself at home. I don't blame you a bit".
I handed her the glass of water at which point she drank half of it and topped it with Jack Daniels and then topped my drink off as well. With her head in her hands, she apologized for her outburst and told me that Shive was a piece of crap. I surprised myself and said that I could have told her that he was a piece of crap the first time I met him. She asked me to explain and I did.
For the next few minutes I voiced my intuition about Shive and she listened and asked more questions. My inhibitions were now nonexistent as we liberally sipped bourbon and hammered her ex-boyfriend. Abruptly, she got up off the couch and said she was going to change and check on her daughter. I watched as she walked across the room and heard her giggle at her own inability to maintain a straight line.
I continued to enjoy my drink and noticed it was a few minutes to midnight. I heard Mrs. Weston walking back down the stairs and she entered the room wearing her bathrobe and still holding her drink. I raised my glass and said "Happy New Years Fucking Eve."
