Fbailey story number 725 My Sister Wants It Up Her Ass Mom came into my bedroom one night after I had fallen asleep. She rubbed my back until I had wakened up. Then she whispered, "Your sister just came home crying so keep your voice down." I asked, "What's up?" Mom whispered, "You know that she took a vow to remain a virgin until her wedding day or her twenty first birthday, which ever comes first." I replied, "Yes, then she gets grandpa's inheritance.
Otherwise it all goes to an animal shelter." Mom then said, "Tonight her boyfriend pressured her into having sex." I said, "Oh no!" Mom said, "No, it's still okay. She took it up her ass.
She's still a virgin." I asked, "You woke me up to tell me that?" Mom got real serious and said, "No! I woke you up so that you could butt fuck her. If she is going to keep taking it up the ass she better get used to it." I asked, "Are you serious?" Mom said, "Yes!
That bastard dry fucked her asshole. I need for you to come with me and help or she will never let another boy in her ass again. Then that could led to her letting one of them in her pussy and ruining the whole thing." So I got out of bed.
At thirteen I had started sleeping nude like my mother and my sister. They seemed shy around me but I didn't mind letting them see me naked. So I followed Mom into my sister's bedroom. Pamela was till crying. She was curled up in a ball under her covers. Apparently Mom had talked to her for a long time before she came and got me. She was not sure that she wanted to let me fuck her ass, after what that other asshole had done to her.
Reluctantly, she let Mom apply plenty of K-Y Jelly to her sore and tender asshole. Mom was gentle and Pamela felt much better about it.
Finally, Mom got Pamela to back her butt up to the edge of the bed.
Mom coated my hard-on with plenty of K-Y Jelly too. Then she held my cock up to Pamela's sensitive hole and had me apply just a little pressure. It took a minute or two for my sister to relax enough for the head to slip just inside. She panicked and I stopped pushing.
As she begged Mom to get my cock out of her ass, Mom insisted that we both just hold still. After another minute Mom had me slid another inch into her.
As the inches went in Pamela became less scared that I would hurt her. When I was fully in her rectum she just asked me to go slow. There was practically no feeling or friction at all. My cock felt like it was in a warm bubble bath. Of course I knew that it was my sister's butt and that thought alone must have been what got me off. As I pumped several squirts of hot cum into her rectum she said, "Mom I can feel him cumming and it feels nice." Mom said, "I told you it would if it was done right." Pamela asked, "Can he do it to me some more?
I'd like to get used to it before I let another boy try it again." Mom just looked at me and asked, "Would you be so kind as to stick it up your sister's ass every night until she gets married?" I smiled and said, "You bet I will!" Well, it was quite obvious that my sister wanted it up her ass, so why not. That was when Pamela rolled onto her back, sat on the edge of the bed, and then stood up to give me a hug. I had never seen my sister naked before.
She always had a pretty face and nice long hair. She always looked good in whatever she wore. Her legs were nice in short skirts. However, seeing her naked was just what I had needed. Her breasts were small but round. It is hard to explain but her breasts looked phony like those girls on the Internet that get really bad boob jobs and they swell up like balloons.
Well that is sort of what Pamela's tits looked like only a whole lot smaller. Her tits were about the size of a baseball with areolas the size of quarters and nipples that were way too big for her breasts.
They were at least the size of a dime if not bigger and they stood out about as long as they were wide. Down between her legs was a really thick bush that had been greased up with K-Y and then her hair was parted right down the middle. No wonder that guy had pressured her into putting out. Too bad that he had raped her asshole dry. His loss was definitely going to be my gain. As she hugged me to her breasts I realized just how tall my fifteen-year-old sister was. Since it was right in my face I sucked one of her nipples into my mouth and started playing with it with my tongue.
Pamela said, "That feels good. No boy has ever sucked my nipples…just Mary and Tina once in a while." Now I knew both of those girls.
They were her best friends and they had slept over many times. That reminded me of something… I asked, "Do I still get to put it up your ass if they are here?" Pamela replied, "Yes little brother, and they can even watch if they want too." Mom added, "I bet they would like to try it up their asses. They certainly get enough cock up their snatches." Pamela giggled and said, "I'll say. They have a contest going to see which one can fuck the most boys. Mary is up to thirty-three and Tina has let thirty-seven fuck her.
Tina cheated though because she went to a family reunion this summer and let twelve of her cousins and uncles fuck her." I asked, "How do they know the other one isn't lying?" Pamela said, "They have to take pictures.
The guy has to have his face showing and his cock in their pussy. Their face has to be showing too. I think Tina's father took the pictures at the reunion. Otherwise they take them themselves with some kind of a timer. I'm the scorekeeper so I have all of the pictures in my dresser drawer." I asked, "Can I see them?" Mom and I looked at them as Pamela went through the stack.
On the back were the date and place and the guys name. I knew a lot of the boys but they were all older than I was.
I said, "I think Mary is pretty. I could get most of the boys in my class to fuck her if she really wanted to win." Pamela smiled and said, "I bet she would go for that. Do you think that you could get them to come here and do it? Then I can take the pictures." We all went back to bed and the next morning Pamela woke me up with a kiss and told me that Mary was all for my idea. Then she asked me if I would make some calls.
Mary arrived before any of my friends did. She let me be the first one to fuck her that day. Even though I had had my cock in my sister's ass I considered myself a virgin until I had slipped into Mary's pussy. She was a wild girl and she thrashed around with me on top of her. It was probably the fuck of my lifetime. All I knew was that I would never forget it. Pamela took the picture and then left us alone on her bed.
I was facing her and looking down at her breasts as my cock traveled in and out of her pussy. Her breasts looked a lot different than Pamela's breasts looked. They were bigger around but flatter and her nipples were much darker. She felt so good around my cock that I hated to pull it out of her. As the boys finished fucking Mary, they would call one or two of their friends to come over.
By ten o'clock that night Mom put an end to it and told the boys to come back in the morning.
That would be Sunday. Pamela counted the pictures that she had printed out. Including me Mary had let thirty-three of us fuck her, doubling her score, making a total of sixty-six. I had been the first one and I was also the last one. Even so, I still only counted once. Then Pamela let Mary watch and take a picture of me in her ass.
She was on her back facing me with her legs up and her pelvis rolled. Mary wanted a second picture, closer of me in her ass and her holding her pussy lips open to prove which hole I had my cock in. The next morning a whole string of boys flowed through the house and had sex with Mary in Pamela's bed. With a fresh start, a new day, and word of mouth…Mary was going through six or seven boys an hour.
Mom put an end to it about eight o'clock that night so that Mary could get cleaned up and go home. She needed to go to school the next day. The final count was sixty-six new boys and seven that had just come back for seconds. Of course I got in her twice myself. Mary had doubled her score again making a total of one hundred and thirty-two. At school on Monday I was the most popular boy there. At least a hundred boys approached me asking if Mary would be at my house again.
When I caught up with my sister she was very excited and said, "Tina was pissed when she found out that Mary let ninety-nine boys fuck her over the weekend.
Only three had fucked her." That was when I told Pamela that I had a hundred offers from guys. Later Pamela found me and said that it was a go, that both girls would be at our house after school and that I should pass the word. I'm not sure why I said it…but…I told the boys to bring two dollars to cover the cost.
I was turning Mary and Tina into prostitutes. Hey, I was their pimp. Over the next three months those two girls let every boy that came to my house fuck them. Not everyone was a first timer but that was Pamela's job to sort them out. I certainly got all of the pussy that I needed from Mary and Tina and all of the anal sex that I needed from my sister.
Unfortunately, the girls got a bad reputation among the good girls, who called them sluts. Fortunately, neither girl cared.
By the time the two girls graduated from high school the number of guys had approached close to seven hundred different guys. Pamela only let three other guys in her ass.
The third one was a keeper, so of course she kept him, she married him, and she inherited grandpa's money. The End My Sister Wants It Up Her Ass 725