Blair and Jenn
(This is a continuous story in multiple parts. It will only make sense if you read it in order.)
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P r a c t i c e
"I don't understand why you won't just stick it in my ass and get it over with. I thought you said all guys want it like that."
"Blair, if we did it like that, it would hurt, and you'd hate it. And I DON'T want that. If we're gonna do it, let's do it right."
She sat, pouting.
"Look, Blair, it's going to feel incredible for me, either way. But I'll enjoy it a hell of a lot more if it's good for you, and you enjoy it too, and that's going to take some time."
"Well, fine, as long as we get it done by Saturday, so I get to have you there before Jenn does."
"Blair, more than likely, that's not gonna happen. If your parents were gone all week, like that first week, that'd be one thing -- we could go a little bit at a time, night after night, work up to it. But I'm not having your dad find us in your room with two of my fingers up your butt."
"Oh, Brian, you say the sweetest things..."
They spent Sunday afternoon working on relaxing her "back there," but as the time grew near for her parents to get home, even stubborn Blair had to admit that she probably wouldn't be ready by Saturday afternoon, and Brian's "date" with Jenn was Saturday evening...
B L A I R
Friday at band practice, Brian couldn't help but notice an extra twinkle in Blair's eye. He knew she was up to something, but he also knew that she wasn't going to let him in on it until she was ready. When it came to finding things out from her, he had learned that he could slow the process down, but he couldn't speed it up.
Well, maybe he could... When they got home, he refused to ask, pretending he hadn't noticed anything. She tried not to fall for it, but he had her.
"Aren't you wondering what's up?"
"Oh, is something up?" He tried to keep a straight face, but she was so eager, and so cute when she was eager, he couldn't hold it, and he burst out laughing. "OK, I give, I've been wondering - what's up?"
She turned her back to him, pulled her shorts and panties down to her knees, bent over, and pulled her cheeks apart. Brian gazed in amazement at what he saw: there, between her cheeks, where her little brown star used to be, was a 1 1/4" blue circle, surrounding a classic yellow happy face. "Know what that is?" she trilled.
"You're kidding me..."
"Well, do you?"
"You never cease to amaze me," he replied, in awe. "It's a butt plug."
She straightened up, ran to him in little panties-around-the-knees steps, threw her arms around his neck, and kissed him. "Surprised?"
"Um, to say the least..."
"I bought two of them after work Monday. I wore the small one all day Tuesday and Wednesday, and this one is the medium, I wore it all day yesterday and today. They had a large, but it was a monster... no offense, but it's WAY bigger than you are. There's no way you can say I'm not ready for you now, all you gotta do is pull it out!"
He did.
He carried her to bed, setting her down on her back. She finished removing her panties, and peeled off her top and bra, while he undressed.
He crawled into bed, and she began to turn over, onto her knees. "Not that way," he said, "let's have you on your back."
"Really?"
"Yeah, based on what I've read, it's easier to stay relaxed that way. And I'll get to see your face."
She blushed. He kissed her face, kissed her breasts, and continued kissing down her tummy, to her pussy. She was soaked. He barely applied his mouth, and she imploded into a colossal orgasm.
He pushed her knees up, and eased first one, then two, then three fingers up her ass, confirming she was sufficiently slick and loose. He thoroughly lubed his cock, and positioned it against her sphincter. He pushed, softly, meeting little resistance -- the plug had done its job well. He eased half of his length into her.
"How's it feel?"
"Fantastic, I had no idea... more, baby, give me more."
Brian didn't think he'd ever been this aroused, this hard. It was going to be an effort not to cum too quickly. He pulled back, leaving only the tip, surrounded by her anus. He paused, letting the immediate urge to cum pass.
"Don't tease me," she panted, wrapping her legs around his back, pulling his hips forward with her feet. He eased forward, filling her with most of his length. She moaned in pleasure.
"Fuck me," she whispered.
He did.
He started slowly, then built speed, until their mutual rhythm felt perfect, the lush sensuality of her tightness all but overwhelming him. She continued to pull on his ass with her lower legs, then she crossed her ankles behind his shoulder blades, grabbing her feet with her hands. Her shift in position allowed him to sink his final inch into her.
He began to thrust with more intensity, and found himself in a zone, his cock a fucking machine, so engorged it ached, his orgasm distant. She met each plunge of his with a buck of her hips. Their entire universe became reduced to the stimulated nerve endings within the tiny areas of friction they were sharing, their brains consumed by the waves of pleasure being sent by the euphoric neurons.
"I'm. . . going. . . to. . . cummm. . . " she moaned, and her breathing quickened as her orgasm arrived. Her tunnel squeezed him even tighter as she surrendered to it, her opening constricting and pulsing, finishing him. He followed her into the most distant depths of bliss.
When his erection was gone and he slipped out of her, they held each other, side by side, their arms and legs intertwined.
Brian recognized this as her moment, so he didn't say anything. When she was able to speak, she said, "There were so many things I didn't know... my ass is SO sensitive, compared to my pussy. The sensations are so wonderful, so different, but not just different, so, um, so sensual, so intense. I just love it. It's way more effort to cum, there's not nearly the connection to the clit, and no g-spot, of course. I mean, let's don't do it that way every time, but I want to do it again, and again, and again.
"I thought Megann and Jenn were out of their minds, allowing guys to do that to them, but they were right, it's heavenly.
"And I thought you were being ridiculous, making me wait, for some silly rule of being relaxed enough. But you were right -- putting the small plug in the first time was, um, difficult. I mean, it hurt. But after working up to it, getting used to it, having you back there was just magical.
"Let's do it again." : : : : :
J E N N
Brian did the simple thing with Jenn, he just called her, and invited her over. While the concept was simple, the call itself wasn't, for Brian anyway. Even though he found other words to say other than, "Hey, you wanna come over and fuck?" both he and Jenn knew that's what he meant, and he felt very awkward.
Without consulting Blair, he realized it was obviously wrong to do it at her house. Fortunately, finding another location was easy -- on Saturday night, Brian's parents were driving to a town about an hour and a half away, to see the traveling production of "Wicked." He could have gone with them, but given the choice, he decided he'd rather fuck Jennifer.
Blair was visibly nervous. This was the only scenario that he hadn't needed any of her help to set up, or any involvement from her at all. They both realized that this was the only one that posed any danger to their relationship, because it wasn't based on any setup, play acting, or +pushing. Because of that, this was the first scenario that had any real chance of challenging their status quo.
