How I Popped My Mom's Cherry

I know what you're thinking. Impossible, right? I mean, a woman can't give birth and still be a virgin, can she? I'm here to tell you that it is not only possible but it actually happened. I guess I need to give you some back ground first. My mother fell in love in high school with my father. She was one of the most popular girls in school. She could do it all. She was a cheerleader; she was on the softball team and the chess and debate teams. She got straight A's. I've even seen her old report cards, very impressive.

As I said she fell in love with my father and decided that he was the one. She was going to give him her virginity. A little bit about my father first. He was a jock, football, baseball and wrestling teams. Sometimes he was playing two sports a season. He was not your typical jock though. He actually had a good head on his shoulders. He too, got straight A's and was on the debate team. That was where they got to know each other and where they fell in love. Mom said he could argue Death from taking a soul. That was the main thing she found attractive.

They had a few dates. Just the usual stuff; going to the movies, dinner, a couple school dances but no place where they could actually do anything other than some over the clothes petting. Until one weekend my grandparents said they were going away for the weekend for a little "alone" time. They trusted mom because she had never given them any reason not to. She told my father about it and said she would let him know the minute they were gone. They were leaving on a Friday night and would not get back till Sunday evening.

Well, no sooner were her parents out the door and mom was on the phone to her boyfriend telling him to get over right away. You can bet he listened to her, as he knew what was going to happen. It didn't take him ten minutes to get over there. As soon as he was through the front door mom grabbed his hand and pulled him up to her room. In no time at all they were both naked and groping each other. They just couldn't wait to lose their virginity to each other. Even though my father was a jock he still had not had any pussy.

Well, mom was so wet at the prospect of losing her virginity that she did not need any foreplay.

Besides, they had all weekend to play. Her parents would not be back till Sunday evening. As you might have guessed, two things happened at almost the same time. My father, this being his first time and all, was very excited. Maybe, just a little too excited. Right as he put the head of his cock to mom's pussy and just started to penetrate, he shot. Yup, he blew his load early. He did not get in far enough to pop mom's cherry. The other thing that happened at that exact moment was my grandpa grabbed him by the back of the neck and threw him across the room. My father, being the jock he was, was in excellent shape so he rolled with it, jumped up and ran bare assed out of the house with my grandpa right on his heels. Being the younger of the two he quickly left grandpa behind. I'm sure it shocked the hell out of grandma to see a naked young man run out of the house, as she was sitting in the car waiting for grandpa, he had left the directions to the hotel on his dresser. That was the reason for their return. Needless to say they did not go away for their weekend.

Grandpa made an appointment for mom with the family doctor but he could not see her for almost three weeks. The appointment time came and the doctor examined mom from head to toe and verified that everything was ok with mom. He even checked her hymen and stated that it was intact. Grandpa was finally satisfied that everything was fine and that the family would not be shamed. Almost two months went by and mom told grandma that she had missed her period for those two months. Grandma took her in for a pregnancy test and sure enough, it came back positive. While there, she had the doctor check to see if mom was still a virgin and again, he verified that her hymen was still in place. She was still a virgin. One of my fathers little soldiers made it through. But my grandparents considered it a miracle.

A little bit about my grandparents. My grandparents were very well off. They wanted for nothing and had an awesome house that my grandpa designed. He was an architect so money was never a problem. He built his house with every convenience you can think of and even had a state of the art security system installed. That will play a major role later on. Grandma had been a school teacher before her and grandpa got married so when they decided that it was too much of an embarrassment to let their only child attend school when she was pregnant, even if it was a miracle child, they pulled her out and home schooled her for the duration of the pregnancy. The nine months practically flew by, according to mom and she went into labor. Since she was at home when it happened grandpa just drove her to the nearest hospital for her delivery. Unfortunately, it was not an easy delivery. I was a breach baby so they had to take me by c-section. So, you see, even after 9 plus hours of labor and giving birth to a healthy baby boy, yours truly, mom still had her hymen intact. The doctor even made note of it at moms six week check up after my birth. It is probably in some medical journal somewhere. "Woman gives birth with hymen still intact."

After giving birth to me, mom took the high school equivalency exam and passed with flying colors. Soon after that she took the college entrance exam and passed that also. My grandparents helped raise me so mom could continue her education. By the time I was in school mom had finished with her Masters degree and was hired at a very prestigious company where she made excellent money. She also learned about investing in school and from grandpa, so she was never hurting for money either.

Oh, I forgot to mention something about my father. When he and his parents were told about the pregnancy they quickly packed up and left town. They didn't want him to mess up his future with some, and these are their words "two bit whore that could not keep her legs closed." Last I heard he was holding down two jobs, fry cook and pizza delivery after he blew out his knee in college. I guess his silver tongue never got him any where.

My grandparents died when I was sixteen and left everything to us. Needless to say, but with grandpas investing, job and life insurance and mom's investing and job we will never have to worry about any thing again. Not that we ever have but our bank account is in the nine figures.

Not that you would ever know by looking at us. We live the simple but good life and can go anywhere and do anything we want to. Mom decided to take me out of school and home school me till I went off to collage. She wanted to make up for all the time she had missed with her always working. She quit her job and they told her that if she ever wanted to come back the door was always open for her.

We set up a class room in the den. It consisted of two very large oak desks facing each other. With computers on each, complete with everything you can think you might need in this day and time, printers, web cams, faxes, scanners and all manner of gadgets. The desks were of the type that has the completely enclosed front so that no one standing in front of them could see what is happening under the desk. We had an overhead projector and whiteboards, chalkboards and just about anything else you might need in a class room environment. All that was left to do was to set a work schedule and we had the perfect home school. Mom believes in a well rounded curriculum so we would start the day off in the pool swimming at least 25 laps. Now, let me give you a better picture of my mom. She stands 5'3" and weighs about 108 lbs. Her measurements are 38dd-25-36. She has blond hair that comes down almost mid-back with just a hint of curl and very intense green eyes. Her lips are full and always look as if she had just eaten a cherry lollipop, they are that red. Most of the time she doesn't even need lipstick; her nails are always perfectly manicured and her toes perfectly pedicured. She goes every Saturday to have them done. Her body has been trim since high school. She worked really hard to get back in shape after she had me and she constantly works to keep it that way. She would always wear a one piece swim suit when we would swim of the mornings.

After our swim time we would have a lite breakfast of fruit and toast or a small bowl of wholegrain cereal and then it was off to class. I would sit down to my desk and mom would sit down to hers where she would plan the next day's lessons and pay bills and stuff. Sometimes mom would just throw on a robe after our swim and sit around for about half the day in that. Other times she would dress up as she did when she would go into the office of how you might imagine a professor or principle might, all business. After morning class we would then have some other type of activity such as, tennis, basketball and running, anything that involved exercise. Then it was a couple more hours of classroom studying and we would be through for the day.

This went on for several years. Since I was being home schooled I did not have the usual breaks that other kids had but when we would study a particular subject we went on some very nice field trips. To study art we went to Paris, France to visit the Louvre. To study Greek mythology we went to Greece. There are some distinct advantages to being rich. That was about the only extravagant things we did. And it was all for studying. Since I didn't have the time off that other kids had I finished my home schooling about a year ahead of other kids my own age. So I started studying for my college entrance exam. It was just before I was due to take it that everything started to happen.

One day I was sitting at my desk taking a practice exam when I noticed a little whimper coming from across the room. Now, normally I would not have heard it as I usually listen to music when I am studying but the song I was listening to just ended and next one had yet to start. I looked over at my mom to see if she was ok and she was staring at her computer screen with her eyes sort of glazed over. Just as I was about to ask if everything was alright, she sort of shook her head as if to clear it and she got up, picked up the towel she keeps on the floor so her feet don't touch the cold tile floor, and she left the room. I didn't think anything of it until the next day when it happened again. I was starting to get worried that something might be wrong at first but when I asked her later if she was feeling ok she got a little flushed as if she was embarrassed. She said she was fine and not to worry about her. I was worried so I started watching her more closely. This seemed to happen about every two to three days. Looking back now it seems like I should have known what was up right away but I have led a very sheltered life. Hardly any contact with other people, let alone women. It finally dawned on me one day when I was watching her closely when I was supposed to be studying and I saw that her right arm was moving ever so slightly under the desk. She had not changed out of her swim suit that morning so I know she had very little on. Well, this time her moan was a bit loader and her head tilted back with her eyes closed. I knew she was playing with herself. It all made sense now. Mom has never dated since high school although she has had plenty of opportunity. She would always tell me when I was growing up that I was the only man she needed in her life and she didn't want to share me with anyone.

Once I realized what was going on I started watching her very closely. I had always known mom was a gorgeous woman but I had not looked at her in a sexual way until now. Sound familiar? I know a lot of stories like this have this kind of start to it so why should this be different? I have looked at my fair share of porn and jacked off plenty. It was usually to girls my own age that I found in the Barely Legal magazines. I just had not thought of my own mother that way. I mean, she didn't date. She always down played her major assets. She was always just "MOM." But know that I knew she was playing with herself, in the same room with me in it, how could I not start thinking of her in a sexual way. I started trying to think of ways to find out what she was looking at on her computer and of a way to watch her under the desk as she got herself off.

One Thursday night I had an epiphany. I suddenly knew how to find out both. I went to the den after mom was in bed and loaded a keystroke program on her computer. You know the kind that records every keystroke someone makes. So the next time she played with herself I could find out what she was watching. I would not be able to put the other half of my plan into action until that Saturday when mom went for her weekly visit to the spa. It was usually an all day thing so I knew I would be able to get everything set up before she got home.

I got the opportunity the very next day to find out what she was watching. I closely watched her as she would sit there for a bit just watching me study. Then she turned to her computer screen and hit a few keys and sat watching the screen very intently. I looked at her right arm out of the corner of my eye and sure enough, it was moving slightly. I chanced a quick glance at her face and she was staring intently at the screen and biting her lower lip. I heard a couple small moans and then her head went back and her eyes closed. I watched as long as I dared and pretended like I was studying as she looked over at me and smiled and said she was going to shower and change. As soon as she was out the door I went over to her computer and turned the screen on. I quickly found the keystroke program and got it running and saw the files mom was looking at. I was a bit surprised; it was the security footage from the house surveillance system. I quickly copied the files and sent them to my own computer so I could look at them at my leisure. I put mom's computer back in hibernate mode and went and sat back down at my own desk.

I pulled up the files and looked at the ones that had been viewed the most. There were two in particular that she really liked looking at for some reason. I was soon to find out why. As I opened the oldest file first I was in for the shock of my life. It was of grandma and grandpa. But not like I had ever seen them. The file was taken from the security camera in the kitchen. Both grandma and grandpa were totally naked and grandma was bent over the kitchen table, the very same one that we still eat meals on, and grandpa was giving it to her from behind. I had to hand it to the old guy; he was putting it to her very well. Now, our security system even has sound so you could even hear his balls slamming into her clit. Then grandma says something that surprised the hell out of me. She said "Give it to me Daddy. Fuck your little girl!" I was shocked. All this time I thought my grandparents were the perfect, well, grandparents. They were not a religious couple but they were always Mr. and Mrs. Prim and Proper. And here they were going at it on the kitchen table and grandma was pretending to be my mom. How bizarre is that?

I decided to open another of the older files and again it was grandma and grandpa having sex with each other. This time on the front porch, in broad daylight. By the date on the file I could tell it was just a couple of weeks before they were killed in the accident. And, yet again, I was in for another shock. I could clearly hear grandma say, "Fuck me, David. Fuck your grandma in the ass." I was stunned, to say the least. My grandparents were complete perverts. Well, I must be too, because my cock was trying its damndest to burst out of my pants. I had to undo my jeans just to get a little comfort. I knew that I was running out of time though and I still wanted to see what mom was watching today. I clicked on that folder and was in for another surprise. The camera this time was in my bedroom. I didn't even know it was there. I looked at the screen and saw myself coming out of my bathroom with just a towel around my waist. I had stopped in the middle of the room and pulled the towel off and stroked my cock a few times and walked over to my bed, which was just out of the frame, to lie down and masturbate. I remember that night; it was only a couple of months ago. And it was already the most watched file on mom's computer. I was blown away. First, about my grandparents apparently fucking all over the house and pretending to be both my mom and me. And then about mom watching a tape of me giving myself a couple quick strokes and the file was looped so that it played over and over. My mom was watching these files and masturbating to them so she must like the thought incest.

Right as that thought entered my head; my mom came back into the room so I quickly closed the files and pulled my work back up on the screen. She came over to look to see where I was at in my work and at the last minute I scooted up to the desk so she would not see that my pants were undone and I had the biggest hard-on of my life. She gave me a quick kiss on the top of my head and said that I was done for the week-end as she wrapped her arms around my chest and her breast poked into my back. I couldn't help it, I came right there in my underwear. Between all the stimulation from the files, knowing that my mom sits across the room from me and masturbates quite frequently and her 38DD poking me in the back, I just couldn't stop it. Mom left the room saying that she was going to splurge tonight and order a pizza as I struggled to get my still rock hard cock back into my pants and rush up to my room where I proceeded to jack off two more times before the delivery man got there. Off camera, of course.

The next day mom left out early for her appointment and I headed to the nearest department store. I remembered seeing a wireless home security camera set that had two cameras and a wireless receiver. I bought it and headed back home. The first thing I did was call the security company and let them know we were doing some work one the house and would be shutting the system down for a bit. Then I did just that. I didn't want mom to see me place these cameras where I was going to place them. The first one went under her desk. All the way in the back up against the face of the desk. It took a while; and another trip to a camera store for a light gathering filter, to get it in place. When I first had it hooked up and I sat at the desk to see what I could see I realized that it was way to dark. Hence, the additional trip for the filter. Once in place it was perfect. The next time mom decided to masturbate I would be able to see everything. The second camera went into mom's bedroom. These cameras were very small, about the size of a cigarette lighter, so it was very easy to hide. Once the cameras were in place I sat at my desk and looked to see what I could see. Perfect view under mom's desk and a complete view of her bedroom with a look into her bathroom when the door was opened. Mom never had a reason to close that door so I knew I would be able to see in there as well.

Mom came home later that evening and I told here about a power outage in the neighborhood earlier so she would not suspect anything about time missing from the security cameras. She said as long as it didn't cause any other problems then we were lucky. We watched TV for a few hours and then I kissed mom goodnight. I was planning on putting on a little show for mom so I had a bit of an erection as I kissed her goodnight. I know she couldn't help but notice and I had a feeling she would be watching the security cameras live tonight. As I got to my room I heard the TV being shut off and a few seconds later the door to the den opened up. I went in my room with a smile on my face. I went into the bathroom and took a quick shower and walked out of the bathroom with nothing on but a full hard-on. I had taken the time this afternoon to rearrange my room so that my bed was just in sight of the security camera. I had also picked up a few books about incest. You know the ones; Family Tales, Taboo Lust and Incest Letters. I pulled the books out and sat propped up on my bed and started to read. I almost completely forgot about the camera as I got into the books. Especially the mother/son stories. There were a lot of them so I didn't feel in the least bit guilty that I was putting on a show for my mom in the hopes that I would soon get to fuck her. I must have stroked for about an hour when I finally came. I would stop as I got close and then start up again as the pressure subsided. When I finally did come, I shot my biggest load to date. It was all over my hand, my chest, the books, the bed and even some on my face. I must have zoned out for a few seconds because next thing I knew there was a knock on my door and mom was asking if I was alright. I told her I was and that I had just been reading a little bit and was about to turn in. She left my door and I staggered to the bathroom to clean up. What a mess.