Eddie and Cindy (and Me)

by SweetSandy

Copyright© 2019 by SweetSandy

Erotica Sex Story: "Randy! Your turn!" Eddie had rolled off of his sister. It was my time... My friend Eddie offers to teach me the facts of life by offering his willing sister.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Teenagers   Consensual   Heterosexual   Fiction   Sharing   Incest   Brother   Sister   Gang Bang   Exhibitionism   First   Masturbation   Petting   .

“No NO! Not like that!” Eddie scolded.

I was sitting on the floor facing his sister. As I had been told, I leaned in and gave her kisses, well, actually just little pecks. She giggled after each peck as I blushed and sweated profusely. I had never kissed a girl. Well, ok, I kissed my older sister, but only after mom told me to make up with her after hitting her. That was on the cheek and didn’t count. I was kissing Cindy right on the lips!

This was the late 1960’s; time of hippies, drugs, free love, Woodstock, Apollo, and oh yeah, Vietnam War and USSR. But Eddie and I were just entering high school, and I was sitting with him on blankets in their basement kissing his younger sister as he critiqued. We were having a sleepover, but the pizza and cokes and potato chips were all forgotten.

“Here, like this. Watch me!” Eddie pushed me aside with one hand and moved to face his sister.

She giggled again and looked straight at her brother. Eddie started forward, opened his mouth, his tongue came out right as their mouths collided. Slurps and smooches followed. Her mouth sucked on his tongue as he seemed to just slobber all over hers. I wasn’t sure about all this. It was weird enough watching him kiss his sister like that, something I would never have done with mine. And it seemed awfully wet and messy.

He broke their wet kiss, “Here, you try.”

I tentatively leaned back towards her again, my face turning red as I stuck out my tongue. She giggled and stuck her tongue out back at me. We sat six inches apart, blowing raspberries at each other. At least that must have been what it would have looked like had their mom come down at that moment.

But their mom didn’t appear, and I finally closed in, and our tongues touched. Just a little tap, then a tentative lick. She returned each touch of the tongue with a muffled snicker. Finally, she opened her mouth, inviting me in, so I pressed my lips against hers and our tongues tangled. I think I came in my pants right then.


Eddie and I met when they moved in just down the street from us. We lived in a suburban neighborhood with hills and woods and streams. Back then, houses actually had yards with trees and lots of land for kids to play army or cowboys or fall out of those trees. Eddie’s home was a single-story brick ranch style with a full basement on a sloping lot. It had a creek running beside the house, and his father had built a real treehouse for his kids.

We were just finishing Elementary school and moving to Middle school at that time. Eddie had an older brother and a younger sister. His brother, at 17, was way older than us kids, at least in our eyes. His brother never hung around Eddie or me, so I rarely saw him. Eddie’s sister, Cindy, was a year younger and did hang around us, though at that time, she was more of a brat and a nuisance. That would soon change.

As the Middle School years went by, we built forts and played army and goofed around in the creek. The fancy treehouse became central to all the army battles with neighborhood kids. These battles would usually consist of three or four kids in the treehouse and a half dozen or more on the ground. We threw hand grenades of pinecones and water balloons at each other. We almost always ended up with no clear winner, as there was no coordination on the ground, and the high ground of the treehouse was easily defended. No one ever seemed to realize that the treehouse could be taken by just waiting until they ran out of ammunition.

Eddie always fought from the treehouse, while I was sometimes there and other times on the ground. Cindy would play with us boys as well. She would always stay in the treehouse with Eddie. The two seemed to get along together, much better than my sister and me.

By the end of the 8th grade, hormones had started to kick in, and things shifted. Cindy wasn’t quite the brat she used to be, and she and Eddie seemed to be around each other every time I came over. I didn’t really mind, as Cindy was beginning to look cute. In school, I never had a girlfriend; I was too shy, too short, too nerdy and definitely not a jock. But I also didn’t really think about Cindy, other than ‘one of the gang.’

One time, Eddie and I had a sleepover at my house. I had a double bed in my room, so he and I slept there together. That night he started talking about his sister.

“Randy, you know Cindy likes you, don’t you? Do you like her?”

I didn’t know what to say. Up to that time, I don’t even remember touching her. And I only talked to her when she asked me something or well, maybe when the three of us were playing some game. I never thought about it.

Well, I guess I did THINK about it, I mean about ‘liking’ her ... as a girl, that is.

“Uh, sure, I guess.”

“You know we’ve done it.” He stated, emphasizing the ‘It’.

The words didn’t register to me. Done it? I hadn’t even kissed a girl, much less ‘it’. I said nothing.

He continued quietly, “We played doctor.”

That part seemed interesting, but no big deal. I had kinda played doctor with a girl cousin, years earlier. Probably most kids have.

“Last month, we did it. Well, she got scared while we watched a movie.”

I didn’t think much about that either, ‘cause I had been scared with movies and haunted houses and such and would just hold my sister’s hand.

I just shook my head, feigning understanding. Still, nothing seemed unusual, except for that ‘It’.

“See, we had made up a game where we would dare each other into doing things. I guess it started a couple years ago. We’d also run around and crash into each other, ending up in a pile, playing. Or I would jump out and scare her, and she would grab me tightly instead of running away. Or she would dare me to walk around in just my underpants. Then I’d dare her to do the same. Sometimes she would hold my hand during scary movies. Afterward, we’d kiss each other ... right on the lips. ‘Course we’d just laugh at ourselves. We would also play Twister, tangling up together until we collapsed into a pile. That’s when she first kissed me. She also let me feel her titties when I dared her to lift her shirt. But they were small.”

Eddie seemed to be just rambling, bouncing from one thing to another, but he had my attention now.

“One Friday, my mom and dad were out at a party, and my brother was supposed to be watching us, but he never did. We were in the basement watching a scary movie again. I think it was some wolfman thing that we weren’t supposed to watch. We were wrapped up together in a blanket in front of the TV. My brother yelled down that he was going out. I didn’t care. A really scary part came, and Cindy was climbing all over me. I fell backward as we laughed at ourselves. I looked at her and realized she was on top of me. We kissed. A lot! It’s kinda funny now, thinking back. I mean, I rolled her over and pinned her down as she laughed. We were acting silly after the fright. I kissed her again, and she stuck her tongue into my mouth.”

Listening to Eddie had confused me. I couldn’t quite get this stuff with his sister.

“We had played doctor previously. I mean, I was the doctor, and she was the patient. I would lift her shirt and put my ear to her bare chest and listen. Then other times, she would do the same with me. We would kiss the hurt part and make it all better. I kissed her titties. Another time, I told her she was bad and needed to be spanked. I grabbed her, tickling her and then rolled her over and spanked her. She squirmed as I pulled her gym shorts and panties down and spanked her bare bottom. She wiggled and laughed and told me ‘no fair,’ but then I said, if she let me see hers, I would let her see mine. She agreed. I let her go, and she rolled over, her pants still down nearly to her knees. I saw her pussy.”

My eyes were wide at that. I had NEVER seen a girl’s titties or ... just anything! All I ever had was a Sears catalog with women in underwear or in a bikini. Closest I had been to live girls in scanty clothing was at the public swimming pool, nice but not naked!

Eddie continued, “So I showed her mine. I pulled down my shorts and pulled it out. You should have seen the look on her face! Her eyes were big. It was funny. She touched it, and it moved a bit. Her face turned so funny with that, too.”

“Anyway, after that silly wolfman movie fright and our tumble and kisses and tongues, we started tickling each other, well, kinda. I pushed up her shirt and was tickling her. She pushed at me, laughing at me. I kissed her titties again, and she stopped trying to tickle me. She pulled off her shirt. I helped her remove it. She asked me to kiss her, first on the lips, then on her tits. I did. Then I took off my shirt. We hugged each other, kissing more. I liked licking her tongue and then her tits. She pushed on my pants. So I pulled mine off. She then pulled hers down, and I helped her take them off, too. We lay side and side hugging each other, totally naked.”

I think my mind was overloaded. Eddie and Cindy? Brother and sister? Naked?

Suddenly, he shifted the one-sided conversation away from what happened next.

“Randy, can you come over next Friday night?”

It took me a moment to recover.

“Uh, I can check with my mom.”

“Ok.” He became quiet.

I lay there, not knowing what to think. I mean, I was only 14, and this was well outside my world. I wanted to hear what happened next, but guess I was afraid to ask. All I knew was that my own pecker was hard, and I was wide awake, and I was going over to Eddie’s house next Friday, his and Cindy’s house.


“There! See! You’re getting the hang of it”, Eddie said, proud of his teaching.

I was sitting there with Cindy in front of me. We had just been kissing right on the lips and tongues, with Eddie giving directions. My pants felt sticky. Cindy giggled while I blushed.

Eddie spoke again, “You know you two can do it. Cindy would let you, right?”

Cindy giggled again and answered, “Yes ... Randy, do you like me?”

Tentatively, “Sure ... Ah, SURE! I like you, Cindy.”

“Well?” asked Eddie.

We were in their basement, sitting on blankets on the floor. Eddie’s brother was supposed to be “babysitting” us while their parents were out, but of course, he was out with his girlfriend somewhere. The TV was on, but no one was watching it. Our food and drinks were ignored, no longer of interest.

Cindy lifted her tee-shirt off. I saw my first real live naked breasts. Well, ok teacup size naked breasts. But they were real girl breasts, and they were in front of me. Cindy did another snicker as she looked at my surprised expression.

“I’m up here!” she pointed two fingers at her eyes, mine were still glued to her nipples.

I tore my eyes off her breasts and looked up to her eyes with an ‘I’m sorry’ look. We just sat looking at each other.

“Well, take off your shirt,” Eddie pressed.

I did. I felt totally exposed, even though a guy’s shirt off wasn’t a big deal. At least not a big deal unless a girl was sitting there also with no shirt on.

Cindy leaned forward, her hands against my chest, and she kissed me. I tentatively returned the kiss, already forgetting how Eddie had taught me. Cindy didn’t seem to mind. She arched her back and brought her chest up.

“You can kiss these if you want.”

I want! I immediately tilted my head down to her chest and then, almost frightened that I would hurt her, I gave a quick peck to one then the other. She laughed and pulled my head into her chest.

“No, KISS them!”

I kissed them wetly this time. Remembering the licking and such, I then suckled one of the nipples. It was almost like a long-past memory being revived. I heard a “tickles!” and then she moved my head to the other breast. I repeated there. They had a taste I couldn’t place. But I was sucking a girl’s titties!

She pulled my head away, smiling at me. Her eyes looked different. Something I hadn’t seen from a girl looking at me. She lay back on the blankets and then with little fanfare, pushed her shorts and panties down, sliding them down her long thin, girlish legs and kicking them off her cute little feet.

I was looking, no, staring, straight at a fully naked girl, right in front of me. I’m sure that my face looked stupid as both Eddie and Cindy cracked up laughing. I closed my mouth, but my eyes were between her legs.

Eddie spoke up, “Randy’s never seen a girl before.”

Cindy giggled but didn’t move to cover herself.

Eddie coaxed, “Randy, she wants you to do her. Don’t you want to?”

I was frozen. My brain quit functioning. I aged several years in a second. Twenty minutes ago, I was an innocent little teen kid. Now I was deep into the meaning of biological life. I hadn’t seen a girl’s nipple, and now I had kissed one. I hadn’t seen a girl’s pussy, and now I was staring right at one.

I heard Eddie’s voice, “I guess he’s not sure how to do it. Maybe we show him?”

Cindy held out her arms to Eddie, accepting his request to enlighten me with her ‘come hither’ hands.

I moved over, still in shock, as Eddie shed his clothes without a second thought. His pecker sticking out already primed to go. I finally realized my pants were tented and felt wet. He climbed on top of his sister as she welcomed him in her arms. He lowered himself down as she spread her legs further apart.

It was then I realized I had never seen another guy’s stiff pecker either. I don’t know why that caught my attention. I mean, I definitely prefer girls. But I guess I just never thought about what other guy’s peckers looked like. Since I wasn’t much into sports (in other words, zero), I guess I missed out on most of the locker room jock stuff. Even in gym class, I just stayed away from everyone else as much as possible. Half the time, I didn’t even ‘dress out’, not caring much about the grade. That’s kind of how Eddie and I met. Neither of us was much into organized sports stuff. I preferred playing out in the woods or visiting caves or splashing in creeks or such.

In fact, Eddie and I both liked playing in the woods behind his house. There were probably a hundred acres of pine and oak forest behind our neighborhood. Us kids would take BB guns out and shoot stuff; tin cans, squirrels, birds. Ok, rarely ever hitting any animals. But there were hills and trails to hike and a creek to tromp through. We found a really neat gully surrounded by dense undergrowth and trees that became our fort. Nearby, there was a lumber yard that backed up to the woods. All this land was probably theirs, but there weren’t any Keep Out signs, so...

The lumber yard had a pile of scrap wood, bent two by fours, broken plywood, that sort of stuff, all guarded by a rusted and broken down barbed wire fence. Obviously, that became our supply depot for our fort. In no time, we had a nice little place with a roof and doorway, protected by the dirt walls of the gully. We’d play army and sneak around the area. It was dense and dark in places, with little sunny spots where a tree or two had fallen. I talk about this because this is where we did something else. Eddie had snuck a pack of his brother’s cigarettes, which we smoked, coughing, and choking. Guess the pack really only had a few cigarettes in it. More importantly, it was also where Eddie and I would talk ... about his sister.

“Cindy and I came out here once. By ourselves. You know when I told you we played doctor? Well, out here, we kinda did something too.”

I was trying to figure out when this would have been. He had never finished telling me about his ‘first time’ with Cindy. But, I guess it didn’t really matter. Eddie’s stories were always pretty roundabout.

“We had ‘done it’ before, you remember...”

I told him I didn’t, even though the first part was burned into my memory, hoping he would tell the details of what happened after they got naked together on the floor in their basement. It didn’t work.

“Well, it was a hot day. Really hot. We were sitting here in the fort. We kissed a bit. And then took off our clothes. All of them. We sat for a bit, then she just got up and ran out. Naked! Can you believe that?”

I didn’t say anything, but I believed it. I looked around the fort where we were now sat. In my imagination, I saw her and Eddie, naked, right here. Maybe she sat right where I am now. Her bare butt on this board. I was feeling hot now myself.

“I chased after her. She was running and laughing, barefoot and bare bottom. I was too. My pecker was bouncing, and I felt free. She came around near me, and I tried to grab her. She twisted and turned and laughed. She obviously liked being naked out here in the woods.”

My mind saw her, a little wood nymph frolicking in the forest right here. I wanted to feel free too.

“You want to?” Eddie asked.

I almost said, ‘Want to what,’ but my mind figured it out. Eddie didn’t wait. He shucked his clothes and was out the door before I could even react. But it didn’t take me much time, and I, too, stripped off my clothes and ran outside. It felt so weird, running through the woods between splotches of sunlight and shade. Warmth and then coolness against my stomach. Naked, everything hanging out bouncing freely. Feeling the dirt and leaves between my toes as I ran. Stepping on sticks, hopping on one foot with an ouch. Harboring hidden knowledge that someone might see us. Two adolescent boys running around naked in the forest.

And of course, knowing that SHE had been here, too. Doing this same thing as well. I could almost see her scamper from one bush to the other, then dancing away, showing it all to the world. It all felt so naughty.

I saw Eddie pausing at a tree. He was peeing. I realized I needed to, too. I found a tree and peed on it. It was so funny, two naked boys out pissing in the forest. I wondered if she did too. I’d never seen a girl pee. Eddie ran on with a hoot.

“Hey, Eddie, wait up.”

He paused.

I continued as I panted, “What did you and Cindy do out here?” I was ready to hear more.

We had circled back towards our fort. Some leftover boards were lying outside that we sat down on. We were both sitting there without a stitch of clothes on, my feet tender and sore from stepping on broken sticks and pebbles. My breath catching up to me.

He continued, “Well, we ran around for a while, just like now. It was fun watching her; she skipped and danced, laughing all the time. I finally caught up to her and grabbed her hand. We came back here and did it.”

That was a letdown. No lead-up? No details? I think he could see it in my face. He changed gears again.

“Well, remember that first time I was telling you about?”

“Where you and she were lying on the floor naked after the wolfman scare?”

“Yeah, well, we hadn’t done anything other than kiss before. Hadn’t even been naked together, I mean completely naked together. We were this time. Kissing her seemed different. I don’t know, like it wasn’t really playing anymore, yet it was. It was fun. I kissed her. We played with each other’s tongues. I kissed her little titties. That was neat. She kissed me on the ears, so I did too. I kissed her neck and bit her and gave her a hickey! She got mad at me, and she tried to give me one, too. We ended up tumbling around. Being naked rolling around together was weird. Fun. I got hard, and she laughed at that. Then she touched it, and it moved, making her laugh. She started playing with it, and I had to lay back. It felt like I was going to explode. I showed her how to stroke it, and she did.”

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