We did not see each other much in the next months, as school and school work interfered. The only time we got together, Dawn was involved. Here is what happened.
There was a small forested area behind Elizabeth’s house that Elizabeth, Dawn, and I hung out at. I had discovered it the summer after fourth grade, and my male friends and I would hang out there, talking about girls and sex. If they knew what was to be going on a year later, they would have been green with envy. The girls and I would go there every weekend or so during the summer. We would masturbate together, sitting on logs, or give each other oral pleasures. It was a happy time.
On weekend, just after school started, I headed back there by myself after talking with the two girls and planning to meet for a “play date.” They seemed eager, as school had kept the two of them apart as well. Where we lived, the school system had so badly carved things up that the three of us went to different schools.
I arrived first. There was a small clearing in the trees that we would meet at, where there were several fallen logs and a fire pit we had dug, in case we wanted to meet at night. We never did, but there are so many things we prepared for that never happened.
Elizabeth and Dawn showed up not too long after. Elizabeth wore a short cotton dress, which bounced as she walked, showing off a pair of flower print panties. Dawn was in a pair of shorts and an old t-shirt. They walked carefully down the path to the clearing, and Elizabeth smiled when she saw me.
When they got there, we took seats close to one another on logs and began talking about oral sex. Now, they had experimented with oral sex between the two of them before they brought me in, and it had become a staple of their sex lives. They would lick each other’s pussies every chance they had. In fact, there was one time I jacked off on them as they went at it in a sloppy 69. But, that is another story for another day.
Up until this point, Dawn and I had not had sex, and Elizabeth and I only had it that one time. I was determined that today I would break Dawn’s cherry, at least, and probably give Elizabeth another load as well. I had been horny for weeks, and Elizabeth suggested I finally fuck Dawn.
While they talked about oral sex, and other sexual topics, I sat there quietly between them. I knew what direction I wanted this to head, but I didn’t have to do anything right at that moment. I had worn loose shorts that day, for easy access. So, all I needed to do was to wait for one of the girls to notice my cock, and things would get started.
Dawn noticed it first. Although she was not as hot as Elizabeth, at least in my opinion, she was just as sexual, and liked to look at my crotch.
“I think,” she said, trying to sound formal, “that our friend has brought us something to play with.”
Elizabeth giggled, and Dawn, who was sitting closer to me, reached for the bulge in my shorts. When she leaned over me, I whispered in her ear.
“I want to go all the way with you today.”
“Here?” she whispered back, “Outside? In front of Elizabeth?”
“Sure, why not.”
“Let me think about it.”
In the mean time, she pulled my cock out the leg hole of the shorts, and began stroking it. She sat up on her knees on the log, and I was able to sneak a hand in her loose shorts to play with her crotch through her panties. I was surprised to find them dry. While Dawn was never really put out a lot of lube, I was expecting something. But she was dry!
I rubbed her clitty through the fabric, and I felt her body tense up a bit. Hmm… maybe I had shocked her with my request.
She continued to stroke me, and I felt her relax. I slid her panties aside and began running my fingers up and down her pussy. She was larger that Elizabeth physically, and even to this day I have a thing for chubby pussy. Her lips opened and I put a finger in her up to the first knuckle, swishing it around like a stir stick.
Elizabeth, in the mean time, had leaned over and began licking my dick. I had gotten used to oral sex, so I didn’t immediately plaster her face with jizm. I let the two girls play with me, as I played with and kissed Dawn. She had begun to get wet, so my finger kept trying to slide further into her. I wanted her to want to fuck, so I was teasing her. It seemed to be working!
Suddenly, Dawn stood up, and, wordlessly, dropped her shorts and panties. Her nearly furless slit was delightful, and when she straddled my legs, I knew she had decided.
I felt Elizabeth behind Dawn, holding my cock lightly with her hands. She angled it toward Dawn’s opening.
I was about to warn Dawn of the pain, but then I remembered that she and Elizabeth had already broken Dawn’s cherry.
Elizabeth had the head of my erect cock right at the opening of Dawn’s chubby vulva. Dawn smiled at me, and then dropped.
At first, all I felt was the sudden pressure on my legs. She hadn’t cushioned the blow, and although she was not very large, it was still a shock. Then, I felt her pussy lips on the base of my dick. I looked down to see myself completely buried in her.
Her eyes were closed, and she seemed to be in a sort of trance or dream state. I moved my hips a bit, sliding my cock around inside of her and her eyes flew open. She looked down at me.
“I’m in charge here,” she said, her voice sounding strange, “You will NOT MOVE!”
Okay, now she was giving orders. I didn’t really care. Her pussy felt too nice.
She began to slowly ride me, hips lifting her off me, then back on. It was a case of naiveté, her rhythm, as she kept speeding up. I loved watching that plump pussy sliding up and down my cock, but it was not long before I felt that now familiar burning in my balls.
“I’m going to cum!” I yelled, louder than I had intended.
She grunted and came herself. With the muscle spasms, I couldn’t hold out, and filled her with hot boy semen. Not as good, or as long as Elizabeth… But, hey, for a first time, she did pretty well.
She slid off of me, dazed like she normally was after an orgasm. She sat down on the log next to me with a thump, grinning. She began fingering herself as Elizabeth slid between my legs and began lapping our cum off my semi-hard cock.
“So,” said Dawn, “your turn.”
Elizabeth smiled at her. Dawn knew!
“You told her?” I said, shocked.
“No secrets in the Club, remember? Anyway, she wanted me to try you out first. You and Mike, to see which one she wanted to have sex with.”
“Yeah. He’s okay, I guess. But you are a bit more into foreplay, so she decided on you.”
“More into foreplay?”
“Quit repeating me!” she said, laughing, “Yeah. He’s more like ‘Wham, bam, thank you ma’am!’”
She slipped my cock into her mouth, and hungrily sucked on it, trying to get it hard enough for another round.
“But, you are going to do exactly what I say, understood?” Dawn said, her hand snaking down to her flooded pussy.
Not being one to argue, I just nodded.
My dick was once again in prime shape, and Elizabeth stood up. She pulled her panties down, then stepped out of them.
“Stand up,” Dawn said. I stood, sheepish. My shorts, which were still wet from our fucking, were pulled off of me.
Dawn bent forward, putting her hands on the log. Elizabeth followed suit.
“Stick your cock in me, and get it nice and wet,” Dawn said, wiggling her cute little rump.
I had to squat a little to get my cock in the right position, but I was soon sliding it in and out of her cum splattered hole. I was really getting into it, grabbing her hips and thrusting happily away.
“Now,” Dawn grunted, “stand behind Elizabeth.”
I slid out, leaving her love mound with a wet plop.
I stepped over behind Elizabeth, and Dawn stood up. She grabbed my dick, and positioned it, not at Elizabeth’s lovely vagina, but at her tiny, puckered asshole!
“Yeah, big boy,” Elizabeth moaned, “break my other cherry!”
I had no idea how I was supposed to do that, but with my cock as hard as it was, and the nastiness of sliding it up her poop-shoot was enough incentive. With Dawn’s help, I pressed the head of my cock against her rosebud and began to push.
My god! I thought her pussy had been tight! Her ass grasped me like a glove, and it took quite a bit of pushing to finally slide into her. The mixture of pussy juice and semen from Dawn helped somewhat, but it still took quite a bit of coaxing. Finally, I felt the head of my cock slip past her muscles, and from there it was easy going. It was hot, it was tight, and it was not long before I felt my balls come to rest against her pussy.
Dawn slid forward to look Elizabeth in the face.
“How does it feel?”
“It… uh…” Elizabeth grunted, “feels kind like I have to go to the bathroom.”
I began to slowly slide in and out of her, feeling her muscles grab at my cock as I slid out, and push against me as I slid back in. I never quite got the head past the muscles, because I felt if I did, I would not be able to put it back in.
I found a nice rhythm, and Elizabeth began to cry out.
“Ug… ow… oh… god…” she whimpered.
“Do you… uh. Want… uh…. Me to… uh… stop?” I grunted. I knew I was close to cumming.
I felt her muscles contract. For a moment, I thought her ass was going to break my dick off from the power of her muscles, but after a moment, I found the pressure to be quite pleasurable.
Quickly, I came, filling her bowels with my second load of cum! It kept coming, like a fire hose. I felt her cum again, squeezing every drop of semen out of me.
Finally, I was spent. My dick stayed hard inside her, because of the tightness of her muscles, and I quite enjoyed the feeling.
After a bit, she began to pull forward, and my cock slid out of her, and the head left her ass with a wet plop. Following quickly after it was my cum, or what little could escape for her clutching anal muscles.
I saw her shudder again. Another orgasm!
We cleaned up, considering, and talked for another hour or so before heading home.
Sadly, that was the last time I had sex with either of them. Elizabeth ran away from home at the end of the next school year with some guy who had gotten her pregnant, and to this day, I have no idea what happened to her. Dawn and I broke up shortly after that. She dated Mike briefly, but I did not see her again until years after that, while she worked at a local eatery.
Mike and I are still best friends, although we live in different cities now. Sometimes I wonder if I should tell him everything that happened, but I have a feeling he would be upset by it somehow.
So ends part one of The Way It Should Have Been. Part two is in the works, and will be released shortly.