Cheryl Gets Used

I am a fourteen-year-old boy that lives with two women. One is my sexy thirty-five-year-old mother and the other one is my adorable thirteen-year-old sister Cheryl.

Everything had been fairly normal in our lives. Mom works as a Real Estate Agent and is in and out at all kinds of hours. Dad got caught fucking his secretary. He pays dearly for his mistake with alimony and double child support. We got the house and he got the shaft. He even lost his secretary. Too bad, so sad!

When Cheryl was about eleven and a half she started her periods. Mom put her on birth control and started marking the calendar for both of their periods. Surprisingly she also marked their possible PMS days too. That was for my sake, so that I could duck and cover.

When Cheryl was about twelve and a half Mom started buying her extremely sexy nighties. That was when they both started wearing them after our late dinners. Each week they both got a new one in the same style and in different colors. Each week their nighties got shorter or their neckline plunged further or the material got thinner.

In the months before Cheryl turned thirteen, Mom had her invite a different girlfriend over every weekend. That was when things got exciting for me. Mom would get the two girls to do things in a competitive way. I became the judge.

Mom could be very convincing when she wanted to be. I quickly found out that Mom liked young teenage girls even more than I did…if that was possible. Mom almost always got the girl to try on their nighties in her bedroom so that she could see the girls naked. Often she would get the girl to wear one around me like they do. Now that I liked!

Mom was not afraid to bribe the girls with really cool stuff either. She always seemed to have something that the girl wanted, either a gift card to a clothing shop, a month in a tanning booth, or a day at a spa. The gifts varied with the girl. Cheryl usually knew what the girl wanted. Anyway, to get the gift she had to win the contest. Did I mention that I was the judge?

I got to measure the girls every time to see who had the biggest tits. I got their height, their weight, and their eye color. Somewhere along there I got their middle names, their birth dates, and their parent’s names.

Mom got pictures of them together and separately. She got them in various stages of dress and undress too.

Near the end of the contest both girls would be completely naked so that I could judge the color of their areolas, their assholes, and their pussies. I got to look inside their pussies, smell of them, and taste them too, to see who had the best pussy. No matter what the outcome I would judge it a tie.

That’s where Mom came in. She got to judge them like I had but Mom really got into looking, smelling, and tasting of their pussies. She usually had to take a second taste of the other girl before making her decision. Mom too would judge it a tie and reward both girls.

Sometimes Mom talked both girls into sleeping in her bed so that they could continue to have sex together.

Most times Cheryl got to sleep with them…and have sex with them too.

On that rare occasion, a girl would ask if she could sleep with me, knowing full well what was going to happen.

I got to fuck two girls that way. Both were virgins. I was only a virgin that first time. Each morning after I fucked them again, Mom insisted that she lick my cum out of them. I told you that Mom liked young teenage girls.

Then Cheryl turned thirteen herself. That was when Mom invited all of the girls to a weekend slumber party at our house.

Twenty girls showed up bearing gifts. Mom had them all start out in sexy nighties. No one minded me being around because I had seen them all naked, licked their pussies, and sucked on their nipples. In fact I had a full dossier on each one of them. It contains all of the information that we had learned on their weekend, along with all of the pictures that Mom had taken. She added their panties too, all sealed up in a Ziploc baggie to preserve the aroma.

The day flew by. We ate, we drank, and we had a blast. Then Mom got Cheryl to lay on a mattress on the dining room table. I got to kneel between her legs. Then at exactly nine-sixteen that Friday Mom told me to stick my cock in my sister’s virgin pussy. That was the moment that Cheryl had been born thirteen years earlier. There were several oohs and ahs from the girls. There were some giggles too. Then when I finally got Cheryl all excited and thrashing around they cheered me on.

Mom was the first to kiss Cheryl on the pussy, then on her lips, and welcome her to womanhood. Mom made it out to be the best ‘first’ that any of them would do. She promised that none of them would ever forget their first time. Then one by one each of the girls kissed Cheryl’s pussy, then her lips, and welcomed her to womanhood…even though most of them were virgins too.

That Saturday seven girls approached me about taking their virginities. None of them wanted to do it on the dinning room table though, they wanted it to be private and rememberable.

Mom insisted that she be able to watch the first penetration…just to make sure that everything went well. She also got a picture of my cock in the girl’s pussy for our file. I enjoyed fucking them all. They were all pretty, sexy, and willing. They all thanked me for fucking them too. Basically if you’ve had your cock in one pussy, you’ve had it in all of them. Occasionally I got a pleasant surprise. Brittany still had her hymen and cried at my first thrust, but like a trooper she hung in there until it felt better. Connie had a way of squeezing my cock with her pussy muscles. Joan pulled her knees up to her tits and let me slam all the way into her, hitting her uterus in the process.

On Sunday I had five more requests and managed to satisfy them all before they had to go home. I even had a list started of girls that wanted to come by after school.

Once Cheryl turned thirteen I got to fuck her and Mom every day. Cheryl also let other boys fuck her. Mom didn’t care because she got to lick the cum out of Cheryl’s pussy afterwards.

Sometimes when Mom was trying to sell a house she would let the guy or the couple, fuck her. Occasionally to seal the deal she would throw in Cheryl. That never failed to get the contract signed. Cheryl didn’t seem to mind being pimped out like that either.

As my years in high school passed I got to fuck more and more virgins, thanks to my mother and sister finding them for me.

When I entered college I found the perfect girl for me. Danielle was very much like my mother. Mom used Cheryl to get fresh pussy and Danielle used me to get fresh pussy. It was a marriage made in heaven.

The End
Cheryl Gets Used
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