A question led to a contest, which led to a whole lot more.
Fbailey story number 706
Topless Trampoline Jumping
My sister had her cheerleading squad over to sunbathe and swim in our pool. I wasn’t invited but Mom made me come out and pretend to be useful. I got them drinks like a waiter and then I picked up after them like a garbage collector.
I listened to their shit about other girls, other guys, and then about one another.
“My tits are bigger than yours.”
“Yeah but mine are firmer than yours.”
“Will you guys stop. Everyone knows my tits are what all of the boys are looking at.”
“So what! There is no way to win this argument.”
I had to speak up, “Yes there is.”
I replied, “Topless trampoline jumping.”
They all laughed at my idea. Then my sister said, “You know, he just might be right…perverted…but right.”
Then she asked me, “Just what do you have in mind?”
I immediately replied, “You all get topless. Then one at a time you get to jump up and down on the trampoline for two minutes. I will take videos of you jumping and then give you scores for various things and then later declare a winner.”
Someone asked, “Why do we all have to get topless if only one girl is jumping for you?”
I said, “So that I can judge you all. Besides you don’t want those girls to feel embarrassed being the only ones topless.”
My sister came to my rescue and said, “He’s right, we should all get topless. Besides I want to see how my brother rates my tits.”
So I got my video camera and the girls got out of their tops. I had the two girls that had been arguing go first. I recorded their names and birth dates. Then I had my sister measure their tits. Abby was a 36-C and Brenda was a 34-D.
I had Abby go first and I watched in amazement as her breasts bounced up and down. They were big but they were soft and I zoomed in on her top half.
I had decided to score the measurement, the cup size, the shape, the tan marks, her nipples, her areolas, and of course the bounce to the ounce. While I was at it I scored her tummy, her ass, and her beauty. That gave me ten categories. So with a scale of zero to ten I could give the perfect girl a score of one hundred.
I gave Abby a score of eighty to just start someplace. If I had given her a hundred, there would be no place higher.
Brenda was right, her breasts were firmer…but they sure were sweet too. Both girls were equally pretty but Brenda had great tan lines. I gave her an eighty-one.
Connie, Diane, and Elaine were nice so I gave them seventy-five points each.
Then my sister Fern got up on the trampoline and started bouncing. She had spent hundreds of hours on that thing. That is how she learned to do her flips. I had seen her jump before but never topless. Her tits were 34-C and they were perfect. Her nipples were a nice length and hard, her areolas were a nice diameter, and her breasts were slightly cone-shaped. Her tan lines were very precise and very dark from wearing the same bikini top whenever she tanned. I gave her a seventy-nine.
Gina, Helen, Irene, Judy, Karen, and Lucy all scored below seventy.
The twelve girls seemed pleased with my scores. They agreed that Brenda did look better up on the trampoline than Abby had. They didn’t bother to put their tops back on.
Mom came out to join in and never questioned the topless girls. She just took her top off.
Fern said, “Mom you need to get up on the trampoline and jump for two minutes. But first I need to measure your tits.”
Abby and Brenda said, “We all have. It’s your turn.”
Mom was a 38-DD. She had great tan lines too. When she started jumping her big soft tits just started flopping around. I was afraid that she would give herself a black eye. I had to score her with an eighty-five. All of the girls applauded and cheered her on.
When Mom heard all about the contests she said, “Maybe he should judge our pussies too.”
Some of the cheerleaders were in favor of that but most were not.
Fern said, “Mom, how about just you and me. He can take his time. He will enjoy it.”
Mom slipped off her bikini bottom and said, “I might enjoy it myself. I think he should look, touch, smell, and even taste our pussies.”
Fern asked, “Aren’t there five senses?”
Mom said, “Yes, the sense of hearing but my pussy can’t talk or whistle. However, once in a while it farts.”
That got all of the other girls laughing.
Mom suggested that I do them both at the same time. Fern removed her bikini bottom and got on the ground next to Mom. I knelt between them.
I looked at their pussies. Mom’s was bald and her lips were full, Fern had a round spot of hair on her love mound.
I touched their mounds, cupped their pussies, and then finger fucked them. However, when I got to their clits Mom gyrated and begged me not to stop, she begged me to finish her off, and then she begged me to fuck her.
I looked at Fern and she said, “Go for it. She wants it and you’ve got what she wants.”
So I lowered my shorts. Without underwear on I was naked and my cock was hard. Mom helped me because she wanted it even more than I did. Just as I was about to stick it in my mother and loose my virginity the cheerleaders behind me started to cheer.
Fuck your Mom
Make her hum
Fuck her hard
Make her cum
Fuck your sister
Like a brother should
Fuck her gently
Like only you could
Then fuck the rest of us
Because we need it too
Fuck our pussies
And make us coo
As the twelve girls cheered, Mom pulled me into her and whispered, “Stick it in me now. I want to be your first. If you make me happy I’ll help you fuck all twelve of them this weekend, I promise.”
So I slipped my thirteen-year-old cock into my thirty-five-year-old mother. It felt great and it was my first but all I could think about was fucking my sister and her eleven girlfriends. Fern was sixteen and the rest of those cheerleaders were around her age.
The whole time that I was thrusting into my mother’s pussy I heard chanting all around us. Then they started to make comments:
“My boyfriend doesn’t last that long.”
“Did you see his cock? It looked cute.”
“Look at those buns.”
“Oh my God, He’s still going.”
“He can have my virginity.”
That last comment was from my own sister. She never acted like a virgin.
Then I heard a few other girls saying that they would give me their virginities too. I think I counted six virgins in all.
Below me Mom was saying, “Just another minute. I’m almost there. Oh God you feel great. Yes! Yes! That’s it. Right there! Oh! Oh! Fuck me harder. Oh my God!”
Then she was silent as she continued to wiggle around under me. Just as she started to slow down I started to cum in her. I think I counted eight good squirts and two more that were much smaller.
Abby said, “Would you believe that he lasted thirteen minutes?”
Helen said, “Today is Friday the thirteenth.”
Lucy said, “Thirteen must be his lucky number because there are thirteen of us girls wanting to let him fuck us.”
Fern said, “One down and twelve to go. How are we going to do this?”
Of course Abby said, Alphabetically.”
Judy said, “If we go by age, I’m the youngest.”
Elaine said, “Maybe we should start with the virgins. After all the rest of us already know what a stiff cock feels like inside us.”
Six girls raised their hands and moved around to stand together.
Mom said, “Take your pick.”
I looked the six girls over and Fern was standing on the right so I said, “Let me start with my sister and then I’ll just go right across counterclockwise if that is alright with everyone. Then we’ll just see how far I can get.”
Mom said, “You are all invited to spend the weekend. Call your parents first, then we can have some fun."
Fern got on her back on the grass and opened her legs up for me…and I do mean opened. She could do Russian Splits and she was doing one for me right then. I never in my wildest dreams ever thought that my sixteen-year-old sister would let me fuck her. But there she was naked, spread, and willing. I lowered myself down between her legs or rather below her crotch. Then I leaned in to taste my fist pussy. It was much stronger that I had anticipated but all that did was make me harder. After checking her out with my tongue I slipped my cock into her.
Fern said, “Oh…girls…he is much better than my mother’s dildos.”
There were a few chuckles and then I got serious about fucking her. The funny thing was that I kept thinking about fucking Mom. Actually I was comparing them. Fern’s breasts felt firmer against my chest, her pussy felt great in that position, and I felt like I got more of my cock inside of her. I really liked that position. My sister was totally submissive to me. In that position I could do just about anything to her that I wanted to and she would let me. All I really wanted to do was to fill my sister with cum and get on to the next girl…Irene. I felt the pressure starting to build when Fern groaned loudly and started to shudder under me. When I finished cumming in her and rolled over someone said, fifteen minutes, he’s getting better.
Irene was pleased to let me suck on her clit and lick her hole. She said that her mother had told her not to expect that from any boy, but that she would have to suck the boy’s cock. She didn’t think that was fair. Neither did I. What’s good for the goose, is good for the gander.
As I started around the circle counterclockwise my time kept increasing by about two minutes and everything just kept getting better and better. The pussies tasted better, their holes felt better, and my climaxes got stronger. I felt like Superman.
Mom called me a fuck machine. She told the girls that she had never heard of a boy or man doing what I was doing. I was cumming about every half-hour or so and I never went soft. Besides all of that I filled every pussy along the way with generous amounts of cum.
It was after dark when I fucked the last girl. Connie had been waiting patiently for several hours. However, having my cock poke at her for about forty-five minutes gave her six full-fledged orgasms. She was crying during most of them. She admitted to letting fifteen other guys fuck her but none had ever given her an orgasm.
After fucking all thirteen girls, Mom made us eat. She made me drink plenty of liquids too. I was ready to go again but Mom said, “No!” She said that I was to get a good night’s sleep so that I could start fresh in the morning. She suggested that I reverse the order.
Fern said, “I like that idea. Me and you will be on the end receiving those forty-five minute fucks.”
Everyone had a big laugh but Mom was serious about me getting my rest…in her bed…all night…with no interruptions.