Date: Wed, 20 Apr 2011 21:28:06 -0400 From: MomsBrokenHalo@Safe-mail.net Subject: Cougar Mom 1 - How It All Started (Bisexual - adult/youth) This story is mostly fictional with a little truth mixed in. This is my first attempt at writing an erotic story so please be kind. This is the start of what hopefully will be an ongoing series. This first chapter has a lot of back ground with some sex mixed in. I promise that the following chapters will include more perverted sex of all kinds. Any feedback would be welcome, thanks. Cougar Mom Chapter One My name is Shelly Andrews and this is my story of how I became attracted to younger guys and girls. First let me tell you about myself and some background. I am a 37 year old divorced mom from North Carolina. I am 5'7" 145 pounds, long curly blonde hair and blue eyes. I guess I am a little chubby but what attracts the most attention is the fact that I have big breasts. They are 36 D's. It is what attracted my ex husband to me when we were in college. I met Matt when we were freshman and We were married right out of college, I was 21 at the time and I found out I was pregnant just weeks after graduation. Nine months later I had a beautiful little girl and we named her Sadie. Six months later I was pregnant again and this time I had a son we named Mark. We decided that two kids were enough for us and I convinced my husband to have a vasectomy, I could always talk Matt into anything. Our sex life was ok but nothing special. Matt did have one major fetish and that was lingerie. He would buy me all kinds of sexy things, especially if it had garters and stocking. When Sadie was 6 I suspected that Matt was having an affair with his secretary. I didn't say anything at first because, well I was not innocent and I had my share of indiscretions. Eventually Matt came to me and told me he was in love with the slutty redhead and he wanted a divorce. I cried for a week. After I was cried out, I got angry and decided to take my husband for all I could get. I hired a good lawyer and won a large settlement in the divorce. I also got custody of the kids because the skanky redhead he married did not want to be tied down with step kids. Anyway we were able to live comfortably and I worked part time for an accountant and did a lot of volunteer work just to stay busy and to get out of the house occasionally. I had a string of short term relationships. Most guys turned out to be good for one thing, and some were not even good at that. Fast forward nine years. Sadie is 15 and Mark is 14. Sadie was dating the star quarterback at her school. Jason was just 16 and a junior but he was already being recruited by several major universities. He stands at just 6 feet tall and weighs 205 pounds, all muscle. He has short blonde hair and deep blue eyes. They had been dating for a couple of months and it seemed that every time I was alone with Jason he would flirt with me. Sadie could be in the next room and he would start telling me how pretty I was and he could see where Sadie got her good looks. For some reason I did not discourage him. He would occasionally brush up against me and it would make my skin tingle. Jason was a very sexy young guy and every woman likes to be told they are pretty, especially if they were in the middle of a dry spell. It had been weeks since I had a date and even longer since I had sex with anyone other than my vibrator. We have a large backyard with a high privacy fence and a swimming pool that we all love to use. It was a nice autumn Saturday afternoon and the kids were having a pool party with some of their friends. Several young guys and girls ages 14 to 18 were running around and having fun. I was the only adult and I was playing the good hostess making sure the kids had lots of snacks and drinks. Half the football team was there, they were celebrating a win from the night before. I kept thinking that the guys did not look this good when I was in high school and that the bikinis the girls were wearing were so revealing. I would have been embarrassed to be dressed like that when I was there age. I was wearing a modest dark blue one piece swimsuit with a white gauze-like wraparound skirt and I still felt self conscious. Mark and his friends were in one area of the pool and I was sure they enjoyed watching Sadie and her girlfriends who were laying out in the sun. I also caught several guys staring at my breasts. No matter how modest my swimsuit was it was hard to hide my 36 D breasts. I may be old but I thought I was still in pretty good shape. The party was over and most of the kids were gone. Mark had went with to one of his friends house to play video games. The only ones left was Sadie, her friend Alison and Jason. Jason and Sadie were going out to eat with his parents and they were going to drop Alison off on the way. Sadie and Alison had went to her room to get dressed, Jason was left sitting at the kitchen table with a glass of orange juice. I was at the sink washing up a couple of bowls and cups and I caught Jason watching me. I still had on my swimsuit and see through skirt and I was sure he was getting a good look at my big butt. Jason was telling me how good he thought I looked in my swimsuit. For some reason the idea of him watching me was giving me goose bumps and making me breathe heavy. I glanced back and Jason had his legs spread and was not making any attempt to hide the bulge in his shorts. Believe me the bulge was impressive, a shudder ran through my body as I caught myself wondering what his cock looked like, what it might taste like and what it would feel deep inside of me. Oh my God, what was I thinking, he is just a boy and not just any boy but my daughters boyfriend. Ok, Jason was a really good looking boy but still he was just 16. I guess I was lost in thought so I did not hear him get up. I felt his hot breath on my neck and before I could react his hands came around to cup my breasts. I managed to whisper, "Jason what are you doing? Please stop." "Come on Shelly, you know you like it, I seen how you were looking at my crotch." I tried to pull away but all I succeeded in doing was to wiggling my ass against his crotch. I turned my head to protest and he kissed me, forcing his tongue past my lips. I broke the kiss and said, "Jason, please stop, Sadie will be down any minute." He just stepped back and gave me a wicked smile. He was holding my hand and he pressed it against his hard cock. I could feel the heat through his shorts. When I pulled my hand away he unbuttoned his shorts and let them fall to the floor exposing his cock. Oh God It looked huge, it was at least 7 1/2 inches long and thick. I couldn't take my eyes off it. He got close again and kissed me lightly then pushed me to my knees. I honestly tried to fight it but my resistance was gone. I was hot and I wanted his cock. I leaned in and kissed the tip, then took the head into my mouth. I worked my lips up and down the shaft of his cock a few times when he pushed me away. "Baby I would love nothing better than a nice blow job but like you said we do not have much time. I want to feel your hot pussy on my dick." I was already on my knees and he pushed me forward putting me on all fours. I felt Jason lift my skirt and pull the bottom of my swimsuit to the side. he pushed two fingers in me and laughed. "I knew you would be wet for me." I felt a twinge of shame and guilt but did nothing to stop Jason as he lined the head of his cock with my pussy and pushed forward. He went slow but soon I had all 7 1/2 inches inside me. He did not waste time and soon he was pounding his hard cock in and out of me. I was so turned on knowing that what we were doing was so wrong that I came quickly and came hard. Jason continued to fuck me for several minutes and I came a second time. Suddenly I felt his cock throb inside me and he drove it deep and held it there. Jason pumped a huge load of cum inside my pussy. He had finished and was pulling out when we heard Sadie and Alison coming down the stairs. Jason quickly put his shorts on and meet the girls in the living room. I had not completely recovered, I was still on my hands and knees with cum running down my thighs and breathing heavy. I feared that Sadie would walk in and know what had happened. I was relieved when I heard Sadie yelling from the other room that they were leaving and she would be back later. After they had left, I managed to get to my feet and walked to the bedroom on wobbly knees. I took off my skirt and peeled off my bathing suit. I threw myself on the bed and reached in the night stand to pull out my vibrator. I worked it in and out of me a few time then put it to my lips licking off Jason's cum mixed with my juices. I repeated that act several times before fucking myself into exhaustion. I woke up hours later and wondered if it was a dream. Then I seen my cum crusted swimsuit laying on the floor and my vibrator was touching my right thigh. I felt a wave of remorse wash over me, God what have I done? Not only had I slept with my daughters boyfriend, I had sex with an underage boy, I could go to jail if this ever got out. I prayed that Jason had enough sense to keep his mouth shut. Little did I know that on that Saturday something was awoken deep inside me that would lead to a life that included a downward spiral into depravity and perversion that would eventually envelope everyone around me. XXXXXXXXXXXX The next Monday I was still feeling bad. I was having trouble sleeping and every time I closed my eyes I replayed what had happen between Jason and myself. Every time I thought about it I would have mixed emotions. Part of me knew it was wrong but then there was a part of me who got excited when I thought about being on my hands and knees on the cold kitchen floor with a young stud ramming his hard throbbing cock inside of me. I decided that I needed to get out of the house. I dressed in a white lace bra and panties, a white blouse and a red skirt that came to mid thigh. It was still warm and I decided not to wear pantyhose. I also wore a pair of new red shoes with a modest two inch heel. I grabbed the keys to my silver BMW and my purse and decide to head to the mall. I figured a good dose of shopping therapy would do me a world of good and help clear my mind. For some reason that I am still not sure of, I did not go the local mall, instead I drove to a new mall in the next county. I had not been to this mall before and as I walked around I noticed that there was a lot of kids and younger people at the mall, odd for a school day. When I was in a small dress shop I asked the sales lady about it, apparently the local school system was out for a teachers work day. I actually liked this mall, they had a nice selection of stores including a lingerie store called NIGHT SECRETS that was not part of a national chain. They not only had standard lingerie but also carried naughty costumes, dance wear and slutty looking lingerie. Apparently they catered to a lot of local strippers. I had bought a sexy little back dress at the dress shop so I decided to buy some sexy lingerie to go under it. I found a sexy black corset that would support and yet show off my large breasts. It came with matching black lace panties. The corset had detachable garters so it could be worn with or without stockings. I bought a pair of expensive black silk stockings with the old fashion seams that run up the back of the legs. I was pleased with my purchases and was feeling a lot better as I walked back to my car. I had parked in a deserted corner on the second level of the parking deck. I passed a young guy sitting on a cement wall holding a skateboard. I figure he was 17 or so. He was cute and he smiled at me as I walked by, I smiled back. As I approached my car I noticed that the front tire on the drivers side was flat. I threw my bags in the back seat and took out my cell phone to call triple A. Damn, no reception. I guess the thick walls of the parking deck was blocking the signal. I heard the unmistakable sound of a skateboard and looked up to see the guy I mentioned earlier. He was kind of short, maybe 5'8", skinny with black shaggy hair and a crooked smile. He was wearing jeans and a T-shirt with the name of a band I had heard Sadie talk about. "Ma'am, do you need some help?" "Thanks but I just need to find a place where my cell phone will work so I can call someone." "If you have a spare I can change it for you." Getting a closer look I thought damn he is cute. "No that's ok that is what I have an AAA membership for." He looked disappointed, "OK but my Dad owns a towing service and I have helped him change a lot of tires so I know what I am doing, Promise." I thought about it and I thought what the hell, no telling how long it would take to get someone out here to change it. "Ok if you insist. Thank you." He introduced himself as Nate, short for Nathan. We chatted as he took the spare out of the trunk and changed my tire. When he finished I asked him how much I owed him. "Oh no Ma'am, I don't want any money, My parents always taught me to be nice and help others when I could." "OK first off, quit calling me Ma'am, my name is Shelly and please let me give you something for all your hard work." He got a shy look on his face and said, "well maybe...oh never mind its ok." Now he had me curious, what did this boy want? "Come on Nate, what is it you wanted to ask me?" "Well Ma'am...I mean Shelly, you have a really nice car, I have never had a ride in a BMW." "So that was it, all he wanted was just a ride. "I would love to give you a ride, but I don't know what your parents would think if you took off with a complete stranger." Nate gave me a sly smile, "Mom and Dad are at work and they don't have to know." He seen I was considering it. "Please..?" I decided what could it hurt and gave in, "Put your skateboard in the trunk and get in." We took off and I told him I was from out of town and not familiar with the roads around her so I asked him where would be a fun road to drive. He directed me through a series of turns and soon we were out in the country. I hit the gas and we were zipping around curves flying down straightaways. He was loving it and said he wish he could drive a car this nice. He was cute and sweet so I got an idea, I pulled to the side of the road and put it in park. He asked what I had stopped for. I told him that it would be hard for us to switch places with the car in drive. His face lit up. "You mean it? you are rally going to let me drive?" "Sure, just be careful ok?" "Yes Ma'am." He was so excited I did not say anything about him calling me ma'am. We drove around a little while longer, he was nervous at first but soon he got the hang of it and was doing great. We had the radio blaring and I was enjoying myself but it was time to head back, I did not have to be there when Mark and Sadie got home but I did not like leaving them alone for long. He pulled over on a deserted stretch of road. You could tell he was really happy. As we met in the front of the car He suddenly gave me a hug. "Thank you Shelly this was so much fun, driving a new BMW was as exciting as losing my virginity." Then Nate turned a deep red. "Well I hope losing my virginity will be this much fun if and when it ever happens." Suddenly I started having flashbacks to what happened between Jason and me a couple of day before. I was not sure how old Nate was like I said I figured 17 or so. At least he was not Sadie's boyfriend. I knew I would not fuck Nate, but maybe..... "Nate you say you are a virgin is that true?" He looked sad, "Yes Shelly I am. Why?" "Be honest with me Nate, have you done much with a girl?" "No, just some kissing, when I tried to do more she would stop me." "Well today is your lucky day, I think I owe you more than just a ride in my car. Come with me." I took his hand and lead him to the side of the car facing away from the road. Nate looked confused, he definitely had no idea what I had planned. I looked both ways to make sure no one was in sight then I pushed him up against the car and quickly dropped to my knees. I smiled up at Nate as I reached up to unzip his jeans. He was shaking and I was afraid he might faint before we could do anything. I fished his semi hard cock from his underwear and stroked it a few times. Nate must have been scared to death because it seemed like it took forever for it to start growing in my hand. I heard him murmur "Oh Shit" as I took the head of his cock into my mouth. I started working my mouth up and down the shaft of Nate's cock. As I continued to suck his cock I started squeezing his balls with my left hand. My right hand slipped under my skirt and I started rubbing my already wet pussy. I worked my hand under my panties and started pushing one then two fingers in and out of my cunt. I was fingering myself as I deep throated Nate's hard cock. It was fully hard now and he was breathing heavy. I found my clit and started rubbing the nub at a frantic pace. I pulled back and started sucking just the head as I jacked him off. His cock throbbed once and then he filled my mouth with a good load of cum. It had been awhile since I gave a blow job but apparently I still knew what to do. I swallowed hungrily as I started to pinch and twist my clit. Nate had his eyes closed and had the perfect look of bliss on his young face. Suddenly my body started to shake as ripples of pleasure shot through my body. When I recovered I kissed Nate's deflating cock and put it away, zipping him up. He was very quiet as we drove back to town. I asked if he wanted me to take him back to the mall or drop him off somewhere else. He told me where he lived and we decided that it would be best if I dropped him off a few blocks away. I parked and gave him a kiss. He asked if we could maybe get together again and I told him I doubt if it would happen since I did not live near by. He asked for my number and I told no. I then smiled at him and reached under my skirt and slide off my wet panties. "Here sweetie, something to remember me by." Nate took them and stuffed them into his pocket. "Thank you Nate for helping me today, thank you for everything." I leaned over and gave him a quick kiss on the lips. He smiles, "No thank you Shelly. Who would have thought I would get my first blow job today? Or than I would be able to drive a brand new beamer before my sixteenth birthday?" He got out and grabbed his skateboard out of the trunk and was gone. I was watching him skate down the street when it hit me. Wait, what? Did Nate say "before his sixteenth birthday?" Oh my God, Nate was even younger than Jason. I sat there with mixed feelings. Was I more upset because I had just given a 15 year old boy a blow job? Or did it bother me more that I had let a 15 year old drive my car? I continued to taste Nate's cum in my mouth on the drive home. I was glad I thought to buy a pack of new batteries when I was at the mall because I had a feeling I was going to give my vibrator a workout when I got home. XXXXXXXXXXXX TO BE CONTINUED.