31 - Date With Sam - Date With Greg
by Coach_Michaels
Copyright© 2020 by Coach_Michaels
Romantic Sex Story: Now that the "Substitutes" situation has been agreed to, it's time for the plan to go into action. Frida Dayton and Greg Coal put in an appearance. They have to, because they are fourteen years old. But don't worry, there's still some Paula stuff here. -- I'm numbering them so that they will be listed in chronological order. Every now and then I might stick something in that happened before something else.
Caution: This Romantic Sex Story contains strong sexual content, including Teenagers Consensual Heterosexual Sharing First Oral Sex .
4:43 P.M., Wednesday, November 18, 2015
PLUR-MAkKikM, just outside Honolulu, HI
The legal guardian of Paula Akron and Paul Macon answered the door and invited the ten year old boy in. He was barely ten; his birthday was November 14. Sam Diamond liked this older guy, because he treated kids almost like adults. Not exactly like adults, because they’re not adults, but he treated kids with respect.
Respect; that’s the word Sam hadn’t been able to think of yesterday. Usually when he had heard that word, it was from some adult demanding it, and when an adult tells a child that he wants ‘respect’ he usually means obedience. Ted Michaels wasn’t offering to obey Sam, but he did treat Sam with respect, and Sam liked that.
“Paula’s sleeping in the main house now that Paul’s gone,” Ted was telling him now. “She finds it too sad to stay in the treehouse all night without him there.”
This information brought to the forefront of Sam’s mind exactly why he was doing this. Nobody knew how long the little girl would be separated from her lover. It’s not like Paul Macon was at band camp for two weeks; this could last for months, or even ... No, that was too horrible to consider. Yes, Sam was excited at the prospect of kissing (and likely a lot more than just kissing) a girl, but the real reason he was here was to make his friend Paula feel better, because his best friend Paul had asked him to. Really, he couldn’t blame her if she decided at the last second not to do anything. He couldn’t help but hope that she would do stuff, but he was here for her, not the other way around.
The older man knocked on a door.
“Yes?” came a familiar voice from the other side.
“A Mr. Diamond to see you,” Ted replied.
“Send him in.”
“Will do.”
Ted took hold of the doorknob, but then he hesitated.
“Maybe I shouldn’t say this,” he told Sam in a low voice, “and I’m sorry if I embarrass you or anything, but you can still back out if you want. Paul was very sweet to arrange this, and Paula is looking forward to it. But she’s a very understanding girl and she won’t hold it against you if you walk in there and say that you’re only willing to play video games and stuff.”
Sam’s eyes were huge. He had no idea that Ted knew what was about to happen with his daughter. Except not really his daughter, of course. But still, he was ... he was OK with this?
“Of course,” Ted added with a smile, “I can’t blame you if you decide to go for it. She’s very pretty and, from what I hear, quite skilled.”
“Th ... thanks, Mr. Michaels. I, um, I’m gonna go for it.”
Ted nodded, smiled, and opened the door. Sam walked in and didn’t even notice that it was a pocket door, nor did he note it closing behind him, because he’d just seen her: Paula Akron.
At this point, perhaps, Sam Diamond chickened out and the children just played video games. Or perhaps they got as far as kissing when Sam declared, “Woah, hold on. I’m just a kid.” Perhaps they went further than that. If they did, I can’t depict it here, so you’ll just have to guess. The fact that I’m not depicting it here is a big clue.
Fred was away at band camp for two weeks, and had asked his friend Greg to “entertain” his girlfriend until he returned. He knew that Greg, though only fourteen, was ready to dump his virginity, and he knew that Frida, also fourteen, would be glad she didn’t have to do without until December.
But when Greg entered the bedroom he was unprepared for what he saw: Frida Dayton wearing a sheer nightgown. And nothing underneath.
“Hi, Greg,” the teenaged girl greeted him. “I thought I should wear something sexy, but I thought if you walked in and I was already naked it might weird you out. Do you like it?”
She spun around, and didn’t seem at all concerned that he could see pretty much every inch of her. Other than the almost-naked teen in front of him, the only thing in the room Greg was aware of was a full-sized bed, the sheets already folded back. Was he about to get in bed with a, a girl? With Frida?
“Uh, I, uh, ah,” Greg stated. “Um, ah...”
Frida giggled, and it was the first time she had actually giggled since before Fred had gotten on that bus, headed for band camp.
“I guess I kinda weirded you out anyway,” she said. “Maybe I shoulda wore a dress?”
“Wow!” Greg blurted out. “You are so pretty!”
Frida managed, for a second, to almost look bashful.
“Thank you.”
“So, um...” the boy started over, “what do you want to do? I mean, I know what we want to do, but I mean, um ... how much do ... er ... I sound like an idiot.”
“No,” the fourteen year old girl told him. “Not like an idiot, just like you’re nervous as a pig.”
Now it was Greg’s turn to giggle. “I didn’t know pigs could get this nervous.”
“OK this is what I want to do,” Frida told him. “I want to hug and kiss, and if you want to, we can hug and kiss naked. Then if there’s any time left we can make up our minds if we want to do anything else, like oral sex.”
Greg’s heart was beating like he’d run all the way up the street. Oral sex?! He could feel that he was hard, and for a second he was worried that the teenaged girl might see the bump in his pants, but then he realized that OF COURSE she was going to see it, because he was going to be naked. And hard. In front of a girl.
Thoughts and emotions swam in a confused swirl inside the teenaged boy’s head. A girl seeing his wiener was the stuff of nightmares, but at the same time he wanted it to happen, at least in this case. It still like to scared the shit out of him, but he wasn’t going to back out. If he didn’t do this now he’d hate himself forever.
“Uh, OK. Um...” Now or never, Greg! “Should I take my clothes off right now?”
Frida looked him up and down. She really was touched by Fred’s thoughtfulness in ensuring that she could still have sex while he was gone. How many boys would do that for their girlfriend? Also, the idea of showing off for and having sex with other boys was exciting.
Frida was learning some Big Words that had to do with sex. For instance, the way she liked to show off parts of her body that most people said you had to keep hidden? That made the teenaged girl an “exhibitionist.” She was thrilled when she discovered that there was a word for it. But there was another word she’d just learned. If she started having sex with two boys, and kept switching back and forth, that would make her “promiscuous,” which just sounded so sexy! Pro miss cue us.
Poor Greg though looked like he was about to keel over.
“You could keep your underwear on,” she suggested, “at least at first. I mean hey, I’m wearing this.”
Greg thought that his friend was being more than fair; after all, his underwear wasn’t see-through. So quickly, the teenaged boy stripped down to his white cotton briefs and very deliberately did not cover with his hands, even though he was SURE that his erection had to be showing. It was.
“OK,” she said, “now let’s kiss like before.”
Greg was fine with this suggestion; it hadn’t taken him more than a few seconds that other time to learn that he dearly liked to kiss. Frida ran a hand up and down his back and soon had it resting on his left butt-cheek. When Greg hesitantly did the same, the teenaged girl knew it was time to take things up another notch.
“Here, let me pull this out of the way,” she said, stepping back and hiking the nightgown up until it barely hid her crotch. “Now let’s do it again, only now you can touch my skin.”
After a few minutes of that, Frida simply took the nightgown off and stood nude in front of the wide-eyed fourteen-year-old. Instead of resuming the embrace, however, she lay down on the bed.
“You can look and touch anywhere you want,” she almost purred. “Find out what a girl’s body is like.”
Greg swallowed hard. He looked at her face and her chest. She didn’t actually seem to have much in the way of tits. Her chest was almost boy-flat. Then Greg dropped his eyes to where Frida’s legs joined her body. No boy here.
Gently, Fred Conyers’s best guy friend (Frida was his best friend and everybody knew it) climbed into bed with his best friend’s girlfriend. He ran his hands over her shoulders and down her arms, twice, and then over her flat belly, taking a deep breath before daring to touch the teen’s chest.
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