Chapter 239 First Sex With Kim

Even though Alan had a great time with Glory during the lunch period, he figured his day was only going to get better. He still had an afternoon at Kim's to look forward to. This time he and Katherine wasted no time and drove there straight from school. As a result their clothes provided more cover than in the last car ride to Kim's, so the festivities largely had to wait until they arrived at her house.

The first time at Kim's place it had been just Katherine and Alan having sex while Kim watched, but they had promised her that she would be welcome to join in this time. They met her at the door and the three of them kissed and groped a fair amount before one word was even spoken.

Finally Katherine started up the stairs. But then she stopped, bent over, looked back at Kim and Alan and flipped up her skirt, revealing her bare pussy peeking between her legs. "Last one up is a rotten egg," she prodded, "and the first one up gets first dibs on this!"

Kim and Alan quickly scrambled after her. Because he was much taller, Alan made it to the bedroom before Kim, so he won first dibs.

Katherine was delighted by his victory. "Excellent! It has been way too long, Big Hole-filling Brother. Way. Too. Long." With a turn to Kim, she added, "What say Alan fucks me while you watch, and then after that you can take your pick of him or me next? Then we can all do it together."

"Okay," said Kim, still bummed to have lost the race. She sat down on a chair next to her own bed in the upper-floor bedroom and got ready to watch. "Good things come to those who wait, I guess."

Alan and Katherine were out of their clothes in record time. "They sure do," said Katherine. "Such as this." She held her brother's long shaft in both hands. "Is it just me, or is this thing growing longer every time I see it?" she asked, half seriously.

"I know one way to find out," he replied. He quickly straddled his sister, who lay stretched out on the bed. Then he slowly lowered himself directly into her slit.

"Kim, this is all I ever need," Katherine said.

Alan bounced up and down on her while pistoning his hot meat in and out.

"I'm not kidding when I said I want to be his fuck toy. You've got to try it! Big Stick Brother, give me all you've got! Do me all day long!"

Since Alan had recently bought and read a few books on the art of lovemaking, he wanted to try some new techniques. But there would be enough time to try many of those later in the day. He started simply by churning and rotating his hips, which was something all the books recommended.

Katherine absolutely loved his improved technique, letting him know it by her moans and shrieks.

But he was simply too worked up to stick with that style for long. He fell onto her and started pumping up and down, as if he were doing push-ups with her underneath. He rapidly built up a jackhammer motion, and soon it seemed like he would nail his sister right through the mattress.

She'd loved what he was doing before, but she loved this just as much. Between thrusts, she shouted things like "More!" "Harder!" "Push!" "Fuck!" and "Yes!"

Within minutes, he sprayed his cum deep inside his sister's tight pussy, after which they collapsed into a sweaty, happy heap.

Kim looked upon them in wonder. She'd never seen such a fast and passionate fuck, even in the movies.

But he was just getting warmed up. His dick recovered, springing back into action almost instantly. His sister lay motionless as if she'd just been slain by his pussy pleaser, while he sat up and began to gently stroke his revived hard-on. "Okay, Kim," he said, "it's your turn now. Who will it be first? Me or my sister?"

"Sorry, Katherine," Kim said, as she got up from the chair next to them, where she had been masturbating, completely naked. The sex between Alan and Katherine had ended before she'd had a chance to get off. "I've been with a lot of women, but never a man, and this is my golden opportunity to give it a try. Besides, I've got to get some of what you just got!" She hopped onto her bed and commanded Katherine, "Roll over and make some room."

The bed wasn't very big, but Katherine rolled over towards the edge. Kim took her place under Alan. She expected the same fast, pounding treatment that he'd just given his sister. But she was quite anxious about her first time having sex with a male lover, so she closed her eyes and tensed up. To encourage him she said, "Okay, let's see if you really can drive a hole through the bed this time."

But he was in a different mood now and saw through her false bravado, which was in conflict with her obvious body language. He realized it would be better if he could put her at ease, so he said, "Let's work up to that. But first, let me be gentle, especially since this is your first time."

His body covered hers completely, since he was so much taller than the diminutive girl. He began kissing her on the mouth while running his hands over her boobs and upper torso.

At first, Kim didn't know how to respond. It had been a long time since she'd made out with a boy and she'd never really gone past first base with any of them. Alan treated her gently and kissed her ears and neck and licked her lips. She had hang-ups about a male treating her like that, but she didn't want to disappoint him so she closed her eyes and decided to pretend he was a woman.

Her body started to respond much better as she grew more comfortable with his foreplay. For a while it wasn't that hard for her to imagine that he was just a flat-chested woman since, although he was fairly muscular, he had virtually no hair on his chest. Also, his cock remained below her crotch, between her legs, since he was so much taller than she was, allowing her to maintain the illusion for the moment.

It seemed to her like his hands were all over her. She began to mentally count hands and decided that there were too many. Oh yeah, Katherine! She's getting in on the action too!

Katherine had wanted to leave the two of them alone for their first time together, but just couldn't resist the urge to join in their play.

Kim had had a lot of sex for someone her age, but she'd never been sexually involved with two other people before (other than when the three of them were together in the supply closet).

While Alan's hands stayed around Kim's upper body, Katherine mostly focused on Kim's flanks. Then her hands moved to Kim's pussy, where her fingers prepared the way for Alan's dick. She put one, then two, and finally three fingers into Kim's tunnel.

Soon Kim was more than moist; she was flowing like a raging river.

As if by prearranged signal, Katherine pulled her fingers away and Alan scooted up so that Kim's face now met the bottom of his neck.

Although Katherine had insisted that all her fucks be bareback, Kim had made no such request, so Alan had slipped on a condom when Kim first joined them on the bed. "Are you ready? Here it comes..." he said as he slid his dick into her waiting, wet hole. He was surprisingly calm about it - to fuck Kim was far less of an emotional shock for him than to fuck Katherine. She was so wet that he slid in very easily, with almost no resistance until the end.

By some definitions, Kim was technically a virgin, since no man had entered her vagina before, but the way had been cleared by countless dildos of both the strap-on and hand-held variety. So the feeling of her cunt being deeply filled was not completely alien to her. But Kim quickly realized that no dildo, however fancy, could compare to a real flesh-and-blood penis. The body heat alone from Alan's erection was enough to send shivers of excitement down her spine.

I really like it, she thought with surprise. I like it a lot! As Alan thrust in and out at an increasing pace, she quickly responded by bucking her hips up at him in expert fashion, building on all her experience with female partners who had worn a strap-on. A fake cock is good. But the real thing is so much better, so warm, so alive!

"Alan, fuck me!" she declared.

"I am already!" he replied, somewhat amused.

"But more! Harder! Faster! Like you did to Katherine just now. Really DO me. Nail me! Break me! Fuck! Fuck me now! Impale! Impale me! Cut a hole right through me! NOW!"

Alan turned on his pistoning motion and hammered her for all he was worth, similar to what he'd done to his sister some minutes earlier. Fucking with a condom felt different, but all-in-all he didn't find it as horrible as some people said. For one thing, endurance was a very important goal for him and he could tell right away that the condom would help him last longer since being sheathed reduced his sensitivity. He was especially keen on doing his best with Kim; like many males he wanted to induce a lesbian to become somewhat bi.

Katherine backed off and just stared in wonder as Alan rammed Kim like a steam engine that had spun out of control. God, that's so HOT! That must be what we looked like to her. No wonder she wanted to try him.

Katherine realized that she was becoming jealous. She thought, It doesn't matter, because I'm burning even hotter with PURE LUST! She found herself playing aggressively with her own pussy and clit as she watched.

Once Kim really got into it, Alan rolled them over so that she was on top and could control the action. This caused her to slam down on him even harder, positioning herself so that her clit was stimulated on every stroke.

Katherine thought that was really hot. She yelled, "Ride em, cowgirl!" and reached behind Kim to start fingering around her anus.

Some of Kim's lesbian lovers had played with her ass before, so being stimulated by Katherine made it even easier for Kim to fantasize that she was with a woman, even though at the same time she was loving the feel of Alan's cock and his muscular chest. Soon both she and Alan were screaming at the top of their lungs: "Fuck!" "God!" "Yes!" "Hard!"

Just when Kim thought it couldn't get any more stimulating, Katherine stuck two fingers up Kim's anus, which made her yelp in surprise and painful protest.

Katherine actually had no idea what she was doing with that move, and she hadn't known to lubricate her finger first. She was just trying to be spontaneous and inspired. As a result of the lack of lubrication, it didn't exactly feel good to Kim, whose cry was one of complaint.

That yelp caused Katherine to remove her finger lest she ruin the moment. She thought (mistakenly) that Kim had an aversion to anal penetration, so she tried to make up for her intrusion by caressing and teasing Kim's other erogenous zones, while simultaneously continuing to stimulate her own clit.

With Katherine's help, Alan had reduced Kim to a quivering mass of jelly by the time he spent his seed deep inside her.

After that, the three of them just rested for a few minutes.

Alan was sweaty and exhausted after two such frantic fucks in close succession. "Okay ladies," he said as he finally got off the bed, "all this happy sex makes me thirsty. I'm gonna get a drink of water. I'll leave you two to play for a bit."

"Alan!" Kim shouted, grabbing his attention just before he walked out of the room. She too was starting to come back to life, at least a bit. "That was ... really good."

"Thanks," he said bashfully as he paused at the door.

"Really, I'm serious. You're, like, rocking my world. I'm seriously reconsidering my choice of sexual orientation at this very moment. That excellent fucking makes me a bisexual at least."

Katherine rolled over onto Kim and started kissing her. "Let's see if I can get you reclassified as a lesbian." She kissed again. "After all, it's mostly thanks to you that I discovered the pleasures of women. And I have so much more to learn."

The two went at it with a passion while Alan took a break and cooled off, leaving to flush the used condom down the toilet. Then he went to Kim's kitchen, looking for a snack. There he found some tortilla chips, salsa and a pomegranate.