Raffling Off Robbie
Chapter 1

Copyright© 2012 by Wayne Gibbous

Erotica Sex Story: Chapter 1 - When one of Robbie's sister's friends saw him masturbating one night and reported to her girlfriends just how big he was, they all decided to see for themselves.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   mt/Fa   Mult   Consensual   BiSexual   Heterosexual   Incest   Brother   Sister   First   Safe Sex   Oral Sex   Masturbation   Size  

When it all started, he really didn't have a clue. He, like many boys his age, sixteen, believed girls thought a lot differently that boys did, especially about sex and love and all that.

Robbie Dyer hadn't dated much, he was rather shy, unlike his sister, Katlin, two years older and light-years ahead in the ways of the world. She had lots of friends, Robbie only one or two, more or less nerds like he was.

Oh, he wasn't a super-geek, no, not that bad, he was really pretty cute, Katlin's friends thought, though Robbie was totally unaware of the fact.

Katlin's friends had even talked about Robbie, even though he was two years younger than most of them. It started at a sleepover, as so many interesting things do, a sleepover at Alice Holmes's house.

In attendance were the other very best friends forever of Katlin's, Kim Stanglin, Diane Paul, and Jean Silva. Alice, Katlin, and Diane had all turned eighteen, Kim and Jean, were each less than two months away from that magic age.

So how did Robbie's name get brought up among these older girls? It was Kim that did it with, "You know what I saw? When we were at your house last week, Katlin?"

"No, what?"

"I just couldn't say anything then but, well, it was your brother."

"Robbie? Oh, god, what did he do now?" she asked wondering just what dumb thing he might have pulled this time. Brothers are such a pain, she thought.

"I was going to pee and, well, I went right by his bedroom and the door was a little open."

This now got the attention of all the girls, even Robbie's sister.

"He was doing it, god, he was jacking-off, on his bed, totally naked, his hand going up and down, god, it was so hot."

"No, he was doing it? Really beating-off? God, my little brother, jacking-off," his sister groaned. "I was hoping he'd get to it some day," she laughed.

"Wait, that's not all, what was really hot was how big he was," Kim gushed.

His sister automatically thought of his height, five-eleven, but the other girls knew instantly that what Kim really meant was the height he rose to as he laid flat on his back.

"God, he's got a bigger one than Ben Sanders," she let out, realizing that the rest of them might not have such intimate knowledge of the varsity soccer star from their high school.

But a quick discussion proved that each of them had first-hand information about their soccer-star's length and girth. He was quite a popular guy it seemed.

"And my brother's bigger, his cock is bigger than Ben Sander's? And he's just sixteen?" Katlin cried out, her esteem for her little brother growing just as his cock did when he thought of his sister and her friends.

"Oh, girl, he was stroking it up and down and I watched him until his dick started pumping out cum like you never believed possible."

Oh, maybe Robbie's ears were burning right when they began discussing his penile superiority but, it's more likely that he had no clue about his prowess compared to other boys. After all, he wasn't involved in sports and rarely showered with other boys, and even on the rare occasions when he did, they weren't fully erect and he didn't pay attention to boy's dicks anyway. No, he was too involved in his stash of Playboys to think about boys. But he surely thought about girls. Especially the gaggle of hot girls his sister hung with.

He often thought of them while he jacked-off, they were all hot girls. Maybe Diane he liked the best, she was a curly-headed blond, short, probably about five-two, and just cheerleader-cute with a curvy figure and boobs that were larger than expected for her petite size. She really stood out and she seemed to know it, too. When she was over at his house seeing his sister, she often wore a halter or a tube top that really showed how big she was on top.

There was also Kim with her long brown hair traveling down her back. She had tanned skin and a beautiful smile with white, white teeth that contrasted with her skin so beautifully. She was tall and slender with a nice figure and the most beautiful legs he'd ever seen. Oh, she was so hot, he thought. And, the best thing was that she kind of flirted with him a little. God, did she make him hard. He always had to go jack-off whenever he saw her.

She knew she was hot, of course, she learned at age twelve or so how boys were attracted to her newly-developing body. Yes, and she loved it. It was a power she felt deep inside that made her so glad to be female and curvy all over. She loved being a girl and having boy's eyes on her all the time consuming her with every look.

But Robbie also jacked-off while dreaming of Jean Silva, a freckly red-haired beauty with deep green eyes. He loved it when she would come to see his sister for she almost never wore a bra and she didn't seem to care at all if the outline of her hard, little reddish nipples showed or even if you could see the red circles themselves.

But, let's not leave out Alice Holmes, a bubbly, dark-haired, energetic girl who was a tennis star, he'd heard, but he was far more interested in what was underneath her tennis shorts, having seen her one time about a year ago in their den watching television. He was stunned that she didn't have panties on and he could see the two cleft halves of her beautiful pussy on display, either accidentally or intentionally, the latter certainly fueling his masturbatory fantasies to great heights. It was softly pink and bare and luscious to him, being so horny entering this most intense phase of puberty between fifteen and sixteen. He jacked-off that day so much he was sore. But he did it anyway. That's what a pussy did to Robbie.

We shouldn't leave out Robbie's sister, Katlin. Her shoulder-length, shiny blond hair framed her pretty face with those sensuous lips she was always rubbing with lip gloss. Yes, he even thought of those lips sliding down over his cock when he was especially horny, and that was almost always.

His sister was like the rest of her friends, sexually experienced, mostly with boys but, well, Katlin knew as all girls knew, you couldn't get pregnant from another girl, so there seemed to be quite a lot of experimentation among the five.

Yes, they experimented and were not shy with one another, after all, they were all best friends forever, and that meant keeping deep secrets hidden away for all time. So each girl knew quite well how another girl's tongue felt like in her mouth and how it felt to probe another girl's mouth with hers.

Their boobs and pussies were also quite familiar to each of the five; it was Jean and Alice that first showed the other three how gutsy they were when they first did sixty-nine, four years ago. It was so exciting to all that all ten combinations of the girls were tried out that first night so each girl experienced four, quite wonderful orgasms from her very best friends in the whole wide world. Oh, that began lots of fun as the girls, from then on, openly explored one another's bodies with lips, tongues, fingers, dildos and vibrators.

Jean's mother even spoke to her daughter the next morning about keeping the noise down so her father wouldn't hear the girl's having such fun. The way she said it left no doubt that Mrs. SIlva knew exactly what the girls were up to. She even gave her a new vibrator the next week.

Now, none of these hot girls considered themselves to be lesbians, though, like on Seinfeld, none of them saw anything wrong with that, no, each one considered herself primarily heterosexual with just a little in the way of bisexuality mixed in because it was such fun.

No, these girls had more experience than just with each other. We've already seen that each of the five has known Ben Sanders as well as his equipment and in some detail, as subsequent conversations explored among the girls. It seems that each of them had tasted of Ben, taken him by hand and also taken his rather substantial cock into that wonderful place between their legs that boys all want to occupy. Yes, Ben gets around, he surely got around these five girls.

Oh, and there are many others as well who knew the soccer player's junk. When teen girls begin talking about the size of a boy's equipment, spreading the word around, he quickly gains in popularity among those who take an interest in such things. And many, if not most, do.

But, for our five girls, there had been other boys as well.

Kim currently leads the pack in the number of boys she's had sex with. She went on the pill in the eighth grade and began soon after exploring the interesting variations of penis size and shape becoming most interested in the variations of curvature in the male penis, this she found endlessly fascinating, driving her to expand her sampling which was now up to fourteen boys.

Yes, Kim loved sex and she gave into that love coming to be known as an easy lay. She didn't mind, indeed, she was rather proud of the fact. She loved getting fucked.

The other four lagged far behind Kim who was quite proud of her sexual prowess and the other girls did look up to her and they sought her out when they had any questions about sex, Kim was the 'go-to girl' on that particular subject.

Katlin, Robbie's sister, has had three different cocks pushed up inside her, at different times, of course. The first was when she was a freshman and a cute junior came up to her as school was letting out in the afternoon to ask her if he could give her a ride home. When they were on their way, he asked if she'd like to stop by his house and make out a while. She knew it meant sex and she eagerly said yes. She still thinks of him long after he and his family moved away.

The other two, well, there's a lot of difference between boys and some are better at sex than others. That first boy took his time, made her cum first, really knew what he was doing. That's a wonderful quality in the boy who takes your cherry. The second two, this number including our well-known soccer star, just wanted to get themselves off even though she gave each one ample opportunities to improve their amatory skills, neither did.

Jean, like Kim, began when she was fourteen with a cousin she was visiting in Cleveland. There were, after that, two boys when she was a freshman, then Ben Sanders sampled her charms, followed by a man in her neighborhood that she's never mentioned to anyone, including her very best female friends. They still come together about once a week at her house in the afternoon.

While Kim was the sexual adventuress among the girls, Alice was pretty open to sexual congress, having started at fourteen with her twin brothers, Michael and Jonah, who were sixteen at the time. It all started out innocently enough just roughhousing until she realized that both her brothers had erections in their pajamas and she wanted to see them.

They were both happy to show her and she found that boys had nice things to play with, things that were fun and certainly appreciated being played with. She especially loved making her brothers cum as she hooted and howled at their display of their ejaculatory talents.

Of course, as often happens with some rather innocent penis-play, it quickly led to the two brothers getting little sister naked and having all sorts of fun together. Alice's mom was good friends with Kim's mom and had discussed such girl-rearing topics as birth control and the like and had decided that they would both get their girls to the ob/gyn for their first check-up and get them on the pill sooner rather than later.

This was great news to Alice's twin brothers, who patiently waited the thirty days, filling the time with oral sex from and on their sister, then both took her cherry in a marathon all-day session of unbridled incestual intimacy until all three were well-sated. At least until the next day.

Alice also had adventures outside the family as well, with four boys, actually, and, remarkably, two of them were twins.

Diane had the least number of boys. There was our friend Ben Sanders, of course, and there was James McNabb, a boy she's had sex with for three years now. They're not exactly boyfriend/girlfriend, more like friends with benefits, it's the sex and intimacy and naked fun they enjoy with each other rather than love and passion. But that's pretty nice, too.

So, as much as Robbie was aware of his sister and her four hottie friends, they were now getting an earful about Robbie, particularly Robbie's equipment.

Alice was the first to ask Katlin, "Do you think he's used it? Like has he had sex, you think?"

Chapter 2 »