Mom knew that I jerked off a lot and wanted it to stop.
Fbailey story number 498
Mom’s Plan To Get Me Laid
When school let out for the summer Mom asked me if I was a virgin. At fifteen and a computer geek, sure I was a virgin. She asked me how many times I jerked off in a day and I told her about six to ten times.
The next day Mom told me that I was a chronic masturbater and that she was going to take care of my problem. As much as I wanted sex I certainly did not want to fuck my own mother. Not that she was ugly by any means. In fact my mother was gorgeous and had used her good looks to climb the corporate ladder to a very well paying management position.
That evening Mom took me to some doctor that she knew. He had an office in his home and he put both of my arms in casts covering my fingers too.
At home Mom started placing phone calls to the prettiest girls in my class offering them babysitting jobs…for me. Mom was a very direct person and told each of them exactly what she wanted. Their pay would be based on how well they performed. I could not believe the requirements.
She made sure to tell them I was a chronic masturbater and that I was under a doctor’s care for the next six to eight weeks. She expected each girl to cut down on my masturbating to just four or five times a day. They got a set amount for jerking me off with their hand but they got more for giving me a blowjob and swallowing my cum. They got more yet if they let me cum in their pussies and a big bonus if she were a virgin. The highest payment would be paid for anal sex. Then of course there could be any combination of the above and any number of times, especially if it wasn’t a hand job. In addition they had to feed me, hold my cock when I pee, and wipe my ass when I poop. Surprisingly Mom had twelve girls say yes to the job. She only hired them for one day each. It was a twelve-hour assignment from seven in the morning to seven at night.
However, I knew that Mom would still have to care for me the rest of the time…like right then…I had to pee.
Mom just smiled and walked me into the bathroom, she lowered my pants and my underwear to my ankles, and then she aimed my cock at the toilet bowl. I couldn’t pee with her holding my cock. It started to grow, I got embarrassed, and Mom just giggled. Soon she was stroking me…jerking me off. Before I could cum she slipped her mouth over the head of my cock. When I cum, she swallowed.
That night she put me to bed naked and got out a T-shirt and a baggy pair of shorts for me to wear the next day. She said that it just wasn’t fair that some stupid fifteen-year-old slut would get my virginity. That was when my mother sucked me hard and sat on my cock. My very first time was with my mother and it was much better than I had ever imagined that it would be. Mom fucked me for a very long time stopping just before I cum. It was absolutely the most amazing torture that she could have inflicted on me. I was sure that I would never masturbate again. Her pussy was wet and warm and it clinched my cock as she lifted herself up. When she finally allowed me to cum she took it all before lifting up off from me and then cleaning me up with her very talented tongue. I slept like a baby that night.
In the morning Mom brought in Bethany, introduced her to me, and then sucked my cock hard before leaving for work.
Bethany said, “Is your mother for real? She just sucked your cock. She gave me a piece of paper to fill out in front of you every time I perform some duty. She said that I would be compensated accordingly. What to fuck was she talking about?”
I had her hold up the piece of paper so that I could read it. Then I laughed before saying, “She will pay you more if you put out more. Are you a virgin?”
Bethany said, “No, but you don’t have to tell her that, do you?”
I smiled and said, “Yes I do. You see I get paid too…for telling the truth.”
Bethany said, “I need money to buy some sexy clothes for this summer.”
I smiled and said, “Then I need to cum in your pussy and ass as often as you can get me hard.”
Bethany said, “I don’t do anal.”
I replied, “Then you will not make as much money as you could. I hope a little less is to your liking. Mom won’t pay you as much for letting me cum in your pussy.”
Bethany said, “We only have twelve hours and you are hard, I guess that we had better get started then.”
I smiled and said, “Okay but you will have to do all of the work. With my hands in a cast I can’t do much.”
Bethany undressed and started masturbating herself. After a couple of orgasms she said that she was wet enough and then climbed up above my hips and lowered herself down onto my cock. She was tighter than my mother was but she was not as skillful at it. It took her almost as long to make me cum inside her but it was not as enjoyable.
The first entry read, “Seven-thirty-three he cum in my pussy, in his bed, and I was on top.”
After that she took me into the bathroom, washed me off, and then held my cock while I peed. She fixed me a bowl of cereal and fed me. Then it was time for sex again. She pushed her pussy in my face and let me lick it until I got hard, then she bent over the kitchen table, helped me get it into her, and then she let me do all of the work. I liked it better but I cum much quicker. I think that was the whole purpose. That entry read, “Nine-oh-three he cum in my pussy again. We were in the kitchen, I was bent over the table, and he fucked me from behind.” She didn’t bother to clean me up that time and wandered off.
When she came back she was smiling and took me with her into my mother’s bedroom. She had found Mom’s stash of dildos. In that drawer she found several butt plugs and plenty of K-Y Jelly. She let me watch as she greased one up and shoved it into her asshole. About fifteen minutes later she replaced it with a slightly bigger one and started sucking my cock. When I was hard she pulled that butt plug out, greased me up, and bent over Mom’s bed. Again she helped me get it in, but that time in her asshole. I looked down and smiled knowing that it was her butt, the one place she hadn’t wanted it. She confessed to being an anal virgin if it mattered to me. She also confessed that she needed the extra money.
Before Mom came home Bethany had let me butt-fuck her three more times. She cried during the last one because it hurt her so much. At first I felt sorry for her but then I realized that it had been her idea and that she could have stopped me at any time…she was the one that had prostituted herself to my mother.
When Mom arrived home and entered my room I was just cumming in her pussy for the third time. Mom waited until Bethany recorded our seventh encounter and then she had me verify each entry.
For three vaginal sex, four anal sex, and her anal virginity Mom paid Bethany seven hundred dollars and thanked her after taking a few pictures of us together, nude.
I had no need for more sex but Mom wanted to hear all of the details while she masturbated herself.
In the morning Mom brought in Tiffany, explained what Bethany had done with me the day before and then challenged her to earn more money and then to rub it into Bethany’s face. Tiffany had an evil side to her. She told Mom that she was a complete virgin in all respects but that Mom’s phone call had excited her devilish side. She was determined to give me everything that she had to offer a man…everything.
Tiffany was sucking my cock when Mom left us to go to work. She sucked me until I squirted cum in her mouth and then she started swallowing it as fast as she could. She sucked me clean then she sucked me hard again so that I could fuck her virgin pussy next. After breakfast, a poop, and a shower together I took her anal virginity bent over my mother’s bed with lots of K-Y. I didn’t want that sweet ass getting sore…at least not until after seven o’clock.
Tiffany was not greedy like Bethany had been. She took turns putting me in her pussy and in her ass. She even tried to let me tittie-fuck her but her tits were not big enough yet.
Tiffany really excited me with the way she walked around naked and let me watch her pee. We had sex a total of nine times, my cock was sore when Mom came home. Mom read Tiffany’s report and I verified it. With one blowjob, four anal fucks, and four pussy fucks along with three virgin holes and her trying to tittie-fuck me, Mom paid Tiffany eleven hundred dollars for babysitting me. Tiffany thanked her and tried to give the money back. Mom refused it and thanked Tiffany for setting the goal higher for the rest of the girls. Mom offered Tiffany a ten percent finder’s fee for obtaining more girls that would be willing to let me fuck them. Then Tiffany asked if she could spend the night with me. I nodded so Mom said okay.
In the morning Mom brought Jessica in. Tiffany already had me hard and helped Jessica sit down on my cock. She held it the whole time until I was fully in her best friend’s virgin pussy. The two girls kissed and then Tiffany left so that Mom could tell Jessica the new higher standards to reach for.
During that summer I fucked fifty girls from my class and the class below me as well as some from the class above me. My casts were removed and Tiffany became my girlfriend. No one had earned more money than Tiffany had and no one asked to spend the night with me either. She had single handedly gotten Mom the other thirty-eight girls and made quite a bit of money, every penny of which went into her college fund.
As far as being my girlfriend, Tiffany spent all of the remaining nights that summer in my bed. We enjoyed great sex and Mom couldn’t be happier that I had stopped masturbating. Tiffany even let Mom join us in a threesome occasionally.