I was in ninth grade when it happened. I think it was inevitable, not that I knew that before it happened. It was only after that I came to see the patterns.
Karen was a year younger than I and in eighth grade. She was a walking wet dream, even for me, and I was just at that age when I could cum in a second, then a third, then a fourth etc.
We had a different relationship than most brother sister tandems. We didn't argue and didn't put each other down. Oh, we teased each other, especially at cards, but it was never the spitefulness of many siblings. I guess it was because of her. Karen was a peaceable soul and loved her big brother, me. She had Dad wrapped around her little finger, whereas I couldn't do anything right. Freud would have had lots to say about our family, the way he loved her, and saw me as a challenger.
Anyway, Dad wouldn't punish her but he would take the belt to me in a flash. When Karen was about four and Dad was wailing away on me with his belt, she jumped between us and he accidentally hit Karen leaving big red welts on her arms and back. That I was already covered with welts got no sympathy, but Karen with one, well Dad fell on his knees and begged forgiveness, of her. She put her arms around me and cried. Somehow, that broke him and he never took a hand to me again. Oh I got punished, but never whipped again. Karen was my hero. I would do anything for her. She never took advantage of me either.
Our house was kind of unusual. Karen and I shared a bedroom when young. The bedroom originally had a door to the backyard. So when the folks decided we should each have our own bedroom, we were both getting to be ten or so, they just added a room behind mine and changed that outside door to an inside door. That meant that Karen had to go through my room to get to hers. Since we had been sharing a room till then, it wasn't a big deal. But as I hit puberty and became body conscious, it did start to matter, to me. Of course, Karen walked in on me naked more than once. She never acted like it was a big deal. She ignored it on the surface. She also caught me jacking off a couple times and tried to act like it wasn't a big deal. But maybe the second time she couldn't help but ask what I was doing. That led to a very embarrassed explanation from me. She got fascinated and after admitting that her friends had told her about it, for girls, I got fascinated. That was some eye opening talk we had. I guess we were also unusual in the openness we had in talking, also because of Karen.
I think it was right about then that we were talking one night and I complained that she would walk in on me naked but she never walked through my room naked and always kept the door closed to her room. She got serious and asked if I was really bothered by that. I said yes. But then felt a little guilty, like I was perving on my sister. That night, after she came back through my room to hers after her bath, I noticed she didn't close the door between our rooms. I lay on the bed for a while, staring, and kept wondering, did she do that on purpose? Finally I couldn't stand it and slowly and silently, went over to the door and peeked around. There she was lying on her bed naked. My Lord, she was stunning. I loved her, as a sister: that was really the first time I appreciated her as a woman, for she had become a woman. She looked up and saw me peeking. She smiled and went back to reading her book. How she could be so nonchalant, I don't know. But after that, neither of us was all that body conscious. I sure couldn't be when she seemed to make it no big deal. No way was she going to be more mature than I. Darn right. Yeah, darn right that she trained me just the way she wanted me and I never knew it.
Like I said, it was during her eighth grade year that it happened. She was having a sleep over. It was driving me crazy, all those girls in her room giggling like crazy. Worse, I knew they were all in almost nothing. I had several peeks of one of the girls in just panties and a tight top. If I didn't know better, I would have thought they were doing it on purpose, driving me crazy! Hmmm.
Mom came through my room and into Karen's. "Okay girls, it's time for bed. I don't want to hear any more noise."
I heard the girls all calling out, "Goodnight, Mrs. O'Hara." Mom flipped off the light and shut the door. On the way out of my room, she said, "Go to sleep, and leave the girls alone."
I started to protest but she turned out the light and shut the door. Guilty and I hadn't even done anything!
It was quiet for maybe ten minutes, then the door between our rooms opened, "Has she gone to bed?" sis asked.
I listened at the door, "I think so."
"Good, put the light under the blankets," Karen said back into her room. "Want to join us?" she asked me. "We're going to play truth or dare."
"Okay," I said trying to hide my enthusiasm.
I followed Karen back into her room. The girls had strung a large blanket between her bed and the dresser. It blocked the lamp light from hitting her window. But under the blanket it was bright. The girls were sitting in as semi-circle. I couldn't help it ... seeing them all in panties and tight tops and popped a boner. Since all I was wearing was pjs, it was apparent as all get out. Karen noticed and grabbed my hand as I tried to back out of her room. She pulled me under the blanket with her friends several of whom I could tell were looking at my boner.
"First two losses mean a piece of clothing," Karen said. I realized that everyone had two pieces of clothing. I had my pjs and each girl was only wearing panties and a top. God, in two rounds I could be naked with four naked girls. My boner got even harder.
"After that a loss means a penalty," she finished. "Who goes first?"
"I will," Paige said. She turned to me and asked, "Who's prettiest here?"
Great, my first question and I'm given the type of question that kicked off the Trojan War. I could answer that question honestly and still be okay. "Honestly, I think all four of you are equally pretty, including Karen."
Paige came back with, "No fair. You didn't answer the question. Take it off."
Karen spoke up, "I know Mike. He answered truthfully. I can tell when he's lying." Leah and Makenzie nodded in agreement. Paige looked nervous. Karen smiled devilishly, "We all agree. You lose. Take it off."
Paige looked over at me as I watched amazed that I was about to see her tits. "He's staring."
Leah laughed, "We're all staring. Take it off."
Paige looked around once hoping for support. But I could see this was a bloodthirsty group and there would be no mercy. She lifted her tight top and tossed it behind. I tried not to stare but damn she looked cute with her tits sticking out like that. There weren't really big, but still, they were only the second set of boobs I had seen in the flesh. Her pale skin was deliciously in contrast with her long dark black hair that flowed down over her shoulders.
The questions went around quickly with everyone losing until we were all naked. Then there was the first penalty question. I lost and Makenzie held the penalty choice. "I want to watch you do it," she said. The other girls giggled but agreed with, "Yeahs."
I looked at Karen not quite knowing what she meant, do it. Karen saw my uncertainty and said, "Jerk off." It was obvious that they had been talking earlier since they all knew what it meant.
"No way," I protested.
"Don't be a stick in the mud. Do it," she said.
Eight eyes were avidly watching, including Karen. I knew I couldn't back out. I lay back and started slowly stroking my cock. They gathered round. As my hand slid up and down I felt their legs touching me as they slid in close. Feeling them naked and so close nearly drove me to cum.
"Can I do it?" Makenzie asked.
"Huh?" I was surprised.
"Can I?" she asked.
Karen answered for me, "Sure, go ahead."
Makenzie looked at Karen and smiled as she realized Karen and the girls had me right where they wanted. Her hand wrapped around my shaft as I let go and started stroking my cock. "So hard," she said almost under her breath.
Karen knew how I liked it done, having watched me more than once, "Faster," she said to Makenzie. She sped up and I found myself almost ready to cum right then. The erotic energy with four girls watching was more than I could have ever felt. The rumblings began and bang I exploded like never before. I saw the first glob of cum fly high in the air as the girls all gasped. Makenzie didn't stop and one after another four or six globs of cum went flying up into the air until I was dry. Makenzie dropped my cock which was already subsiding a she stared at her hand covered with gooey cum.
Karen had a towel handy, like wasn't that a coincidence, and gave it to Makenzie who cleaned up her hand before handing me the towel. I cleaned up as the girls all stared. As I sat up they continued the game. Leah lost the next question on a disputed answer. Karen smiled as she gave Leah her penalty. "You have to let Mike lick your kitty." Leah blushed furiously as the other girls giggled. The girls didn't seem surprised by the penalty and later I realized this had all been talked about beforehand. "Do it," Paige said to me.
I went across the circle as Leah lay back and looked up at me. Her hair was around her head. She had almost no boobs, but her nipples were hard and stuck up like little totems from her chest. I had to push her legs apart to get between them. As they spread, her pussy blossomed open like a flower, sticky with sweet sap. She had a light triangle of hair above her pussy, darker than her hair. Her pussy looked completely weird to my inexperienced eyes.
Not having any idea what to do, I licked her pussy while not daring to actually touch her with my hands. Karen immediately started coaching me as she lay down next to me. "Spread her open and lick." I did. "At the top, lick at the top." I saw a bump and licked it as Leah jumped from the contact. "Lighter, around it, tease her." My tongue circled around that nub at the top. I was starting to get the idea. "Now suck and lick," Karen said. That was a little bit too complex, but I eventually got the idea of sucking her whole clit in and rubbing it with my tongue. I grabbed those hard nubbins on her chest stroking and teasing them. That did something for Leah as her hips were bouncing around. My tongue was getting really tired and I would have stopped right then had not Karen been right in my ear urging me on. Then it happened. Leah started jerking around her hips bouncing like crazy and her legs trapped my head. I kept licking as she squeezed my head. I was worried, having no idea what exactly was happening. Leah went slack, her legs falling to the side.
Karen kissed my cheek and told me, "Mike, that was perfect. She had a great one."
That brightened me up. Perfect. Yeah, I was a great lover. I sat back and admired my work. Leah's pussy was open, red, and wet with her cum. Damn, I had made a girl climax. I looked around the circle and Paige and Makenzie were mesmerized by Leah laying back and breathing hard. Karen was smiling, her eyes sparkling in pride at her brother, me. Makenzie finally pulled her eyes away and looked at me. I couldn't exactly tell what she was thinking.
Leah recovered and sat up. She was smiling at me. My heart thumped from the look on her face. Karen broke the mood in the room, "Whose turn?"
Paige said, "Mine."
She turned to Leah, "So, would you do it with Mike now?"
"I just did," she said.
"No, all the way," Paige asked.
Her face was bright as she said softly, "Oh, yeah."
Karen and Makenzie giggled as Paige's mouth fell open. "Penalty for Paige."
Paige blushed as Leah said, "What should her penalty be?"
Karen and Makenzie were saying, "Make her do it." Paige was shaking her head. Leah smiled with a devilish look. "Mike deserves a reward. Give him a bj," she said.
I heard the gasp but my eyes went to Paige, would she?
Karen turned to me and looked at my cock hard and red and sticking straight up. "Good penalty," she said.
"No way," Paige said.
Makenzie jumped in, "You lost. Leah did your penalty. I gave him a hand job." She looked around, "Three against one."
Paige looked around and saw the determination in the faces. She gulped and on hands and knees, came over to me. Her voice shaking a little said, "Please don't cum in my mouth. I saw how it came out before."
I did feel a bit of empathy for her, "Okay, I'll warn you."
Paige smiled nervously. I lay back as she took my cock in hand. She stared at it, then bent forward and kissed the tip.
"Suck it," Makenzie said.
Paige looked her way, then bent forward and sucked the end in. Her head started bobbing as she sucked my rod. Damn, I was already about to cum from everything that had been happening, sitting in the room with four naked girls, all of the questions, then topped off with licking Leah, and now Paige blowing me was over the top. I felt the contractions happening and knew I was going to blow. "I'm cumming."
Paige pulled away from my cock and looked at me like was I serious. So fast? I answered her with the first blast from my cock arcing into the air followed by another and another. Paige pulled away like she was burned. The last couple spurts covered my belly. Karen threw the towel on my belly. "Clean up."
Makenzie asked, "Does that count as a blow job?"
Leah said, "I don't think so. I think you have to swallow for it to be a blow job."
Paige curled her lip, "No way. I sucked him."
Karen jumped in to restore harmony, "I think it counts. He came so it counts. Did you like it Mike?"
I smiled, "Yes."
Paige blushed and Makenzie and Leah giggled.
Paige sat back in the circle as Karen asked Makenzie and Paige, "Do you want to let Mike lick you?"
Both girls' eyes went wide. Paige asked, "Seriously?"
Karen shrugged, "Why not? Leah loved it." To which Leah having recovered said, "Oh yeah."
Makenzie was first to look at me, "Mike, do you want to?"
Now understand that Makenzie wasn't classically beautiful but she had that something that drove teen boys crazy. She was cute, like seriously cute. She was sitting with her legs pulled up but I could see her cute bald kitty between her legs. I always had a thing for Makenzie because she was so cute and vivacious. My tongue got hard just contemplating being between her legs. "Yeah."
"I'd like to know what its like," she said.
I crawled over as she lay back and spread her legs. This time, I knew what I was supposed to do and didn't need the blow by blow help from my sister. I used my fingers to open her as I started licking around her pussy. Makenzie was much more active right from the start. I had to grab her legs and hang on. As my tongue got tired I found I could use my lips and suck on her clitoris while resting and Makenzie seemed to love it. I could tell Makenzie was getting more and more turned on as her pussy flooded my face. I was so lucky to be going down on Makenzie. Half the guys I knew would have given one ball to be able to go down on her. She got more active, before she tensed up as I kept going. Then she exploded, rolling from side to side as I licked her. Her thighs tensed up and squeezed my head until I thought she was going to pop my ears. Then she went limp, her legs falling to the sides and her ass fell to the floor. It was a shock, like the whole world is going round to nothing happening at all. I stared at her pussy and could see it pulsing a little as the goo dripped from her. She was breathing hard and Paige and Leah said, "Wow."
Karen Looked at Paige who shook her head. Makenzie was recovering and said, "Thanks Mike." She sat up and leaned forward to kiss me, just a regular kiss.
Karen said quietly, "Mike, go to bed, but be quiet so you don't wake mom."
I lay in bed just enjoying the fact that I had sex with three attractive sexy girls. I kept saying to myself, 'Did that really happen?' I finally fell asleep sometime early in the morning.
I woke late as it was a weekend. I rolled out of bed and realizing I smelled like sex, I went in and showered. Mom was up and was making pancakes as I came out of the shower. I went to my room and dressed and made it to the table before the pancakes were ready. I loved pancakes, in fact, I still love them.
The girls finally rolled out of Karen's room near noon. Mom made a lunch. Karen was her usual self. Paige couldn't or wouldn't look me in the eye. Leah blushed every time we looked at each other. Makenzie giggled and flirted when mom left the room. I didn't get to really talk to any of them about what had happened. What I really wanted to know was 'Can we do this again?'. I began to realize that especially with Leah, it was a onetime thing. But Makenzie certainly looked like a possibility for an encore.
Parents started showing up to pick up the girls. It was about two before Karen and I were alone. We went back to her room. She closed my door but not hers. I followed her into her room as she flopped onto her bed. I flopped onto the floor. "I can't believe what happened."
Karen smiled enigmatically, 'You liked that?"
"Well, yeah," I said.
"I thought it would be funny, but then..." she stopped no longer smiling.
"What?" I asked now uncertain.
"I got jealous," she said quietly.
"Huh, jealous. Jealous of what?" I asked.
"I didn't think you'd get to have sex before me," she said.
"Oh, you thought you'd do it before me. Well, I beat you. Kinda like cribbage," I said, cribbage was my game and I could almost always win.
She was quiet for a moment and I thought I had really said something wrong. Then she smiled wryly and said, "No, I thought we'd teach each other." I was stunned. I don't know what my face looked like, but Karen laughed and said, "You look silly."
"Well, you kinda dropped that on me like a bomb."
"So, did you like doing it with them?" she asked.
"We didn't actually do it. I mean, all the way. But I did like doing what we did," I admitted.
"Were you like thinking about going all the way with Paige or Leah?" she asked.
"Makenzie," I said.
"Makenzie?" she asked surprised. I nodded. "Really?"
"She was kind of flirting with me at breakfast," I told her.
"Mike, Makenzie flirts with every boy. It doesn't mean a thing," she said.
"But, I mean, after we did, you know, I thought she liked it," I said trying to understand.
"Oh, she liked it. You should have heard how much she liked it. But after you went to bed she told us who she wanted to try it with next."
I was stunned. Then I got mad. But Karen quickly got me thinking about something else.
"Paige was talking about you," she said.
"Really?" I said smiling.
"Don't drool," she teased.
"I'm not drooling. I just never thought it would have happened, I mean, to me, with Paige. I thought Paige didn't like it," I admitted.
Karen laughed, "Yeah, I didn't expect it to get so hot so fast. It was really hard watching and not able to do anything, you know, the girls would have thought it would be weird if I got turned on. So I had to pretend I wasn't even turned on," she said.
There it was again. Could she really mean what she was saying? "Kar, do you mean that?" I asked.
She nodded. "God, I'm getting butterflies in my stomach."
"Do you ... want to... ?" I stumbled to a halt.
"We'll talk tonight after mom and dad go to bed," she said.
That night, I went to bed and turned out the light, listening until the TV switched off after the Nightly News and Dad rumbled of to bed. Then the quiet settled on the house as I lay awake, the butterflies in my belly. I heard every little sound, wondering what this all meant and did Karen really mean what I think she said.
A while later, and I had lost track of time, the door between our rooms slowly opened and I heard Karen's voice, "Come here."
I rolled out of bed and into her room. She had her drapes open so that the moonlight and the light from the street poured into her room. It was enough light now that my eyes had adjusted to see pretty well. Karen had gotten back into bed and patted the bed next to her. I sat down. "Lay down so we can talk," she ordered.
I did. Now we were face to face. We had been like this many times, playing or talking, but this felt so different. "Are you cold?" she asked.
"A little," I answered.
She pulled up the covers and said, "Get under." Now that was different! I hadn't done that since we were little. I got under and she snuggled up next to me. I was suddenly very aware that a girl was next to me in bed. Her hand went to my chest and I jumped. She smiled at me as her hand began stroking around my chest, then slowly moved down over my stomach. She got down to my pj bottoms and I sucked in my breath. I didn't do it on purpose like I might now, but it did create a gap that Karen's fingers found sliding under the waist band.
"Ka ... a ... ren?" I stuttered.
"What?" she asked so innocently. Her hand moved further under the band. "Does this bother you?"
Her fingers found my cock and wrapped around it. I tried to answer but couldn't. I felt the blood rushing to it and embarrassed told her, "Karen, stop it." I knew she would hate me it she felt my cock getting hard, she'd think I was a pervert. Boy, looking back I can't believe how silly I was being. She stroked my cock and didn't expect me to get hard? She didn't stop as the blood rushed in.
"Do you really want me to stop?" she asked. "I think you like it."
I was desperately trying to stop it from growing when it finally impinged, Karen was enjoying it. "Karen, what are we going to do?"
I think she recognized the change in tone and she decided to tell me. "Mike, think about it. We both want to learn about sex, right?" I didn't know about her but I desperately wanted to try out sex, all the way sex. I could only nod as her fingers were slowly stroking my hardening cock. "So, who best to teach each other but each other? It's obvious," she finished.
My thinking ability was slowly eroding as the hormones blasted out from my balls and overwhelmed my brain. As my pop liked to say, God only gives men enough blood to run one head at a time and when all the blood runs south it doesn't leave enough to run the big head.