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Chapter 1

I've never written for one of these websites about how I had sex for the first time but here goes. Just remember that I'm not a famous, professional writer, I'm just a fourteen-year old girl trying to tell how I lost my cherry.

My name is Donna and I live in a medium-sized city in North Carolina. I guess I could tell you that it's Raleigh, North Carolina, that's not enough for you to figure out who I really am. My parents both teach in colleges in the area and I have an older brother, Paul. When this happened, I was thirteen, he was fifteen.

Since this involves sex, I guess I should tell you what Paul and I look like.

I was five-two, just over a hundred pounds, brunette hair down to just below my nipples, well, there's no other bodily landmark but that, so that's what it is: my nipples.

I'd gotten some curves to my body in the last few years and, well, naked, I look pretty good. My boobs have just gone into B-cup and those nipples I've told you about are light pink and so sensitive. I try to go without a bra whenever I can because I love my nips rubbing on my shirt. Like most of the girls in my school, I shave my pussy, you hardly see a 'natural' bush anymore when we change for gym.

Now, my brother, he's really cute, five-seven, wavy brown hair, some muscles, he doesn't date a lot but all my girlfriends think he's hot.

There are two other people in this story, my best friend, Sharon, she was also thirteen when this started and her brother, Randy, who was fourteen.

Sharon is a really cute blond, a cheerleader-type, with short, curly hair and, naked, oh, guys, you should see her. She's perfectly-proportioned and very curvy with a body that could be in Playboy in a few years. She's got the most solid, firm boobs I've ever seen, she can jump up and down and they don't jiggle at all. And these really pretty, dark red nipples that get hard and 'stickey-outie' just all the time.

Randy also has blond hair, they both are natural blonds, and it has some wave to it. He is, well, you usually don't say this about a boy, but he's really beautiful. In the summer he's really tan and he works out so his body is toned and muscular.

Sharon and I have been best friends ever since her family moved next door when I was in the second grade. We've shared just about all there is to share between friends and, as we've gone past ten years old and now into our teens, well, we've, how to say this, we've explored ourselves, well, each other, really, in new ways.

Geez, the truth is, we've done a lot of fooling around with each other, just about everything girls can do with each other, okay? Yes, that, too. We just started out like trying to find out how it felt to kiss a boy but, like happens with so many girls, we tried it on each other.

It was fine until Sharon asked about frenching so we tried that. Well, we were dressed for bed, in her bedroom, in teeshirts and panties, we were ten at the time, our boobs just sensitive little mounds on our chest as we began tongue-kissing.

In only a few minutes, our teeshirts were up under our armpits as we kissed and rubbed each other's little titties which soon became sucking each other's little titties.

Was it fun? Did we enjoy it?

Oh, did we ever. The next time we spent the night together was at my house and when we got dressed for bed we had already decided not to dress. Yes, we knew what we were doing, we knew it was sexual, we knew we both wanted it to go further and we ended up with our heads between each other's legs having wonderful orgasms together.

I have to tell you that my friend, Sharon, is an orgasm machine. I have them and they're great but Sharon has them in almost no time at all and she has them one after another, just on and on. I've fingered and licked her for hours as she's just kept going and going, never stopping, never slowing down. Lucky girl, huh?

So, into being eleven and twelve, we were having sex with each other a lot, most afternoons even. We lived right next door to each other and we were almost always together and when we were together we were almost always pleasuring each other's developing bodies.

We now had real breasts, both of us were becoming really beautiful in that youthful, blooming way young girls have. Our pussies were also getting some peach fuzz then actually hairs which excited us no end.

Sharon and I were also getting to be very adept at getting each other off in any manner of ways and were now using several things to help including a hairbrush we nicknamed, "Dick," for its handle. We also raided her mom's stash of vibrators and dildos when we could. We laughed about the word 'dildo' when we first heard it and realized that it was what her mom's fake penis things were called.

But no matter what they were called, we just enjoyed using them on each other. When we first found them, we had heard that a friend of ours had used her mom's to rid herself of her cherry in the bathtub so Sharon and I did the same. A lot of pink water went down the drain that day.

But, at least we had prepared ourselves for that big day when a boy went inside us for the first time.

We also began having periods, just like most of our friends and constantly traded story after story among ourselves. Then, there began to be a few stories of giving handjobs to boys, then sucking them, and, finally, full oral sex between our girlfriends and their boyfriends. No one was fucking yet or, at least admitting it, yet.

Now that we were thirteen, yes, we were hearing tales of fucking and condoms and the pill and some kind of stuff you can buy that kills the sperm, yes, sex among our friends was changing.

Sharon and I talked a lot about losing our cherries and who the boy or boys might be when the time finally came. We were very hesitant to have it be any boy in our grade for several reasons, the biggest being we thought that a boy a year or two older might have a bigger, more satisfying dick. Yes, we talked about it from all angles.

"Well, of all the guys you know, Donna, who would you like to do it?" Sharon asked me one afternoon while she was using her mom's dildo on me. "If this was him, fucking you right now, just like this, who would you want it to be?"

"The boy that pops into my head is that last boy I saw before we came into your room," I told her.

"Randy?"

"Yeah, your brother, Randy. He's what, a year older, fourteen? He's not in our grade. Have you seen his dick?"

"Now that you ask, yes, I did, about a month ago. I came home from your house and I was walking to my room when I heard him, well, he was jacking-off. I could tell. So, I went and looked. There he was on his bed holding a Playboy in one hand and his dick in the other going at it."

"Well, well, what was it like, come on?"

"Oh, about like this," and she held her fingers apart about an inch.

"You're kidding, that's all?"

"Yeah, I am kidding. Actually it was bigger than I'd thought, more like this," and she held her hands out about six inches, maybe more. Much better.

"Gee, that's pretty nice, right?" I asked not knowing exactly what was big and what was small.

"I know how big my pussy is and it should fill it up pretty good, yeah. So, my brother, huh?"

"Yeah, he's cute and you said he's big enough. I think he'd keep his mouth shut and not brag all over school. What do you think?"

"He's pretty trustworthy and, well, I bet he'd do it. Most guys would, you know."

So I asked her who she thought she'd like to be her first.

"It's funny. You thought of my brother, what about your brother for me? I really like him, kind of had a crush on him for a long time and he's a sophomore in high school."

"Oh, I bet Paul would do it, I'll bet he's jump at it," I told her.

"Well, just pretend it's Randy who's fucking you right now," she said as she slid the dildo back and forth as I closed my eyes trying to imagine her brother moving in and out of me. It got me off pretty fast and I did her right after having her imagine it was my brother Paul fucking her.

That started us pretending that it was the other's brother every afternoon as we got each other off.

But, of course, that was just pretending. We did discuss the real thing, how to get our brothers to fuck the other of us. And birth control. There was no way either one of us was going to do anything with a boy without protection. So, we both schemed what had worked for a friend of ours who wanted to go on the pill so she could have sex with her boyfriend.

We both decided that for several months we would stagger the appearance of our menstrual periods with when they actually occurred.

So, when our periods started on time, we kept our supplies hidden away and disposed of them as they were used so our mothers wouldn't know, then a few weeks later, let it be known that we were late but that it started and made sure that our boxes of pads or tampons were seen by our moms.

Yes, it was devious. What do you want, us pregnant?

So, after about two months I talked to my mom about it and she agreed to get me on the pill to regulate my cycle. Funny thing, though, she also said that it would ease her mind in other ways, too. Hmm.

It was almost two months after that when Sharon's mom took her to the doctor. So, we now knew we were getting closer to getting our cherries popped by each other's brother. Well, if they agreed. But we were pretty sure about that.

One of the things we discussed for days was just how we would get this all going. We could each try to get the other's brother interested, you know, seduce them individually. Or we could just get them together and tell them what we wanted. That had some risk but it also gave us extra courage doing it together.

So, we finally decided to start the seduction process early and it began the next night I stayed over with Sharon.

"Okay, he's in the family room watching television. So go do it and I'll wait here. God, I'm so nervous, are you?"

"Yeah, kind of, but I'm also really turned on, too. How do I look?"

"Oh, girl, that teeshirt is perfect, your nipples really show. He'll love it."

"They should show, you've been sucking them forever already," I said as I turned and went down the hall and down the stairs into the TV room.

"Oh, hi, Randy, I came down to get us something to snack on, chips, cookies, something like that. Can you show me where they are?" I asked him making sure I was in the light so he could see me clearly.

His eyes were staring below my face as he replied, "Sure, Donna, come on, I'll be glad to show you," and when he got up, well, his sweatpants told it all. I knew I had him. I thanked him with a nice kiss on the lips and told him he was so sweet to help me, then turned and walked back out of the room making sure he saw the backside of my little thong panties which showed most of my butt cheeks.

"Well, did he see? Tell me, tell me," she asked as soon as I came back.

"Just give him five minutes and go out and look, I'll bet he'll be in his room with the door closed. He had a big hard-on, I'm telling you, big."

So we each began teasing the other's brother weeks in advance of our plan. It was summer and we were together at each other's houses almost all the time and found lots of opportunities to flash some skin at each other's brother. Was it making us horny, too?

Oh, yeah, big time. The two of us were constantly getting each other off with orgasm after orgasm but our goal was our first penis, that was what this was all for.

We also took the opportunity to sun ourselves at each other's houses in the back yard and a couple of times when I was at Sharon's and her brother came outside, I asked her to toss me the suntan lotion which she did and I had to raise up to catch it. Just happened that my top was untied.

The same thing happened with Sharon at my house as she 'accidentally' let Paul see her boobs. So we made sure that each brother noticed the other of us as we carefully laid our trap.

We were still undecided exactly how to get the ball rolling, whether to do it together, telling both brothers at the same time about what we wanted. Or, to send me over to Sharon's house to seduce Randy and for Sharon to come here and work her charms on Paul. Or, for me to tell my brother that my best friend is waiting for him at her house naked and ready and vice versa.

These we discussed at length, each had it's positive points and each presented possible pitfalls as well. But we knew we had to decide.

So, we opted that each of us would ask our brother what he thought about the other, I'd ask Paul what he thought of Sharon and vice versa. Then we would compare notes and then decide.

That afternoon, I came back home from being next door with Sharon and Paul was in the kitchen eating a sandwich.

I got a couple of cookies out of the pantry and sat down across the table.

"What's up, Sis?" he asked.

"Oh, just over at Sharon's. Not doing much. Talking about guys and stuff."

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Characters: Zoe: f, age 14 Noah: m, age 14, Zoe’s stepbrother James: m, age 16, Zoe’s stepbrother Keith: M, age 37; Zoe’s father Kate: F, age 36; Zoe’s stepmother Jessi: F, age 31; Zoe’s mother Jessi was seventeen years old and two months pregnant when she met Keith, my father. A week later during a passionate make-out session, he took her virginity; practically raping her or so she led him to believe. You might wonder how you rape a willing slut that planned and instigated the so-called...

3 years ago
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Trading FriendsChapter 4 Sheri

(NOTE: Starting with this chapter I will be changing a bit. From now on even numbered chapters will be from the viewpoint of another member of the group. Odd numbered chapters will be POV Robert. This should give the story a slightly different feel.) Sheri: Mom and dad had started out last night trying to read me the riot act; but then they had softened and agreed that what I was doing was probably for the best. Dad said that he really didn't want me to be sexually active, but that he...

1 year ago
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Trading Places

Note : This story is completely fictional! I’ve lived next door to my best friend Eve for my entire life. She and I might as well be twin sisters, and that’s basically how our families treat us. We’re both blond and slim, both on the cheerleading squad at the local high school, and we both have the coolest older brothers ever. Like Eve and I, my brother Mark, and Eve’s brother Ryan, are best friends as well. The guys are only two years older than us, and we all hang out with the same crowd, so...

Incest
1 year ago
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Brothers

As being discreet i always tend to hit the guys thru the net and chat rooms and i happen to meet a straight boy in the chat and was chatting with him gradually telling him that i like guys. But the guy dosent seem to mind and say thats fine and we continue to chat. after 2 or 3 chat sessions i actually exchange my mobile with him and we chatted thru fone for a while too and one day he suggest that i should meet him. I was not so keen to do but meeting a straight guy and seducing him makes me...

Gay Male
2 years ago
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Gay Incest Experience Between Cousin Brothers

Hello everyone, I am Jay from Chennai. I thoroughly enjoy reading true gay experiences of people on this site. Today, I submit to readers one such personal experience which happened a few years back. Summer of 2009 I was in my final semester of my engineering. I was a very good at academics and was one of the top rankers in my college. I had already landed a job through campus placement and I was enjoying a carefree life. I had also completed my final year project, so I used to attend college...

Gay Male
1 year ago
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Strange Brothers

AUTHOR'S NOTE: The story you are about to read is an adaption of, "Strange Brothers," From Mashiro's Castle. It is not a direct translation of the original story, rather a retelling of it adapted for an English audience. If you already know of the Strange Brothers, I apologize in advance. I know only certain parts of the story that have been translated to English, and as such I have had to add my own content to create an ending. Also, I made other changes to make it more of a...

3 years ago
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Imphal Gay Brothers

Dear ISSians, I am Mr. Yohenba from Imphal, 18 aged, 5’5” tall, with a lovely face ( we refer it as rashi leiba maithong in manipuri). I am straight acting guy, pursuing graduation in one of the reputed college in NE India. I belong to a conservative meitei family that includes my apa,ama, two brothers and a nice sister. Let me start my incest gay sex experience with my big brother. My only big brother is doing MBA in marketing in abroad. He has got 23 in last two month. Meanwhile I was...

Gay Male
1 year ago
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Chad and his brothers

It was Friday night, and Chad had nothing to do at the moment in the huge mansion he lived in. The house was worth $954,500, 6 bedrooms, 7.5 bathrooms, and many other rooms too. A backyard tennis court, a pool, and yards upon yards of land around. He shares a room with his brother Ashtin who was still in the shower. It was about 10:45 p.m. and all Chad kept thinking about was "what is it like to fuck a guy?" He thought, "Since Ashtin is in the shower, he's naked, and when he comes out, I...

1 year ago
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Band of Bad Brothers

Jay was very muscular, beefy, a few inches shorter than Chris, but outweighed Chris easily by 80 pounds who was way less developed but looked down at Jay from about 6 feet. Chris was naïve, 18, Jay 32, but told Chris he was 27 to help gain his confidence. Over the previous few weeks Jay and Chris lifted at the gym together, talked about their mutual love for wrestling before Jay started to tell Chris he would make a great wrestler, young, good looking, the perfect good-guy character. Chris...

3 years ago
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Trading FriendsChapter 3

When the guys got to my house for practice the next day I sat them down for a talk. "OK gentlemen, what do you think of my idea after a night to consider it?" They looked at each other then Jimmy spoke up. "I'm not too sure about it, but it doesn't matter, the girls are going to decide for us." "Not for this one they won't. This has to have the active involvement of each one of us. The one thing, which can pull down the whole house of cards, is jealousy. If you can't watch the...

2 years ago
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Trading FriendsChapter 5

Monday at school was interesting in a number of ways. Everside and I were called into the principal's office during homeroom. We were both told in no uncertain terms that any further unpleasantness between us would result in suspension for both of us no matter who was at fault. We were not even to defend ourselves but to run away and call for help. I told the principle good luck with enforcing such an edict. If Billy or his friends attacked me or mine I was going to do my best to make it so...

4 years ago
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Trading FriendsChapter 7

Dinner at the Cooper's was a real treat. Her family obviously knew that I was screwing Jessica, and didn't mind. Her younger sisters were out at a friend's and so I was able to sleep with her in her own bed that night. We sixty-nined for a while then just made slow, dreamy love. When I woke up the next morning Jessica was rubbing my erection and kissing my shoulder. "Is someone still horny this morning dear?" "You had better believe it Robert. How do people who have sex for the first...

3 years ago
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The Story Of Two Brothers

Hi . I am back with a new story of two brothers. Which get to know by this month when I received the mail. Now I am going to continue with story. Mera naam sameer h . Aur meri family me mai bhaiya aur bhabhi h mere bhai mujhse 5 saal bde h. Meri umar 20 saal h. Saadi ke do saal baad bhabhi ki maleriya se death hi gayi . tbse bhai bahut dukhi rhne lage bhai bhabhi ko Jaan se bhi jyada pyar krte the. Maine socha saayad kuch dino me Thik ho jaye. PR ek saal bit gaye aur woo abi bi bhabhi ke gaam...

Gay Male
2 years ago
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Daughters Slut TrainingChapter 6 Daughter Takes on Her Brothers

Note: Thanks to wrc264 for beta reading this! Mrs. Umayyah My eyes flicked from my daughter lying on her back, her first customer’s cum leaking out of her well-fucked and bald snatch, to Principal Carver pulling out his wallet from his discarded slacks, his dick soaked in my daughter’s juices. A hot tremble raced through me. I pulled my fingers out of my own snatch, my orgasm buzzing through me. Masturbating to my own live sex show was an added bonus of whoring out my daughter to pay my...

3 years ago
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Fraternity Batebrothers

“Hey man, you seen Brian and Lee up and around yet? I think they got smashed last night, bro.” Nick looked up from his game of Halo at the question, seeing his fourth roommate, Danny, framed in the door to his room. Danny — Hispanic, 5’10”, with close-cropped black hair — was wearing a loose pair of gym shorts and his tank top was stained with sweat from his usual morning workouts. Nick shrugged, glancing at the clock — after 11 in the morning on a Saturday. “Nah, man, haven’t seen them. They...

Bisexual
3 years ago
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Im a Slutty Sister I Love Both My Brothers

It was afternoon, and the bed in my small room was rocking as my real elder brother, Jeff, who was twenty-one years old, and my younger stepbrother, Lucas, who was twenty, were fucking me together. Jeff was under me, and he was sucking on my erect nipples while my younger brother was behind me fucking my ass. I was screaming, asking him to spank me, too. Dirty things had been going on between me and my brothers for four years. Jeff was getting married next month but he told me that he would...

Incest
1 year ago
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Swapping Brothers

Chapter 1 Lindsey and Pam were best friends at school and they both had a lot of things in common. For one thing, they were both developing into very sexy teenage girls even though they were only 15 years old and they both had lost their virginity during the past year and were learning to love all they were finding out about sex and fucking with the guys they wanted to let inside their horny young pussies. And one other thing that both girls had in common was that they each had an older...

3 years ago
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The gay brothers

It was a nice sunny spring day. We lived in a neighbor hood where everyone knew each other. All the parents we friends, and so were the kids. Me and my brother were outside playing football, like normal. Our parent came outside and told us they were going to the store with our younger sister. We didn't feel like going, so we went inside. We both agreed we needed showers. We have 2 showers in our house, but the other one was for our parents and sister. I got in first. It was a normal shower....

2 years ago
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Lu and two brothers

Long time ago when me and the wife were at a mall in Chula Vista, CA. As we were hanging out at this mall, the wife knew all the holes at this mall. It was a nice sunny June day she was showing me around. After 2:00pm we sat down at an outside bench just to rest a little from all the walking, when I thought everything was fun just her and I. We heard a familiar voice saying “hey you guys” we both looked and noticed one of our friends. He was white about 5’7 meaty in the right spots. As he...

2 years ago
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Brothers

It really wasn’t my fault. It had never been my intention to begin what happened. He was my brother, and I loved him, even when he drove me mad ... but sometimes there is only so much someone can take, and I cracked. I lost my mind, briefly ... but when I came back to myself, I couldn’t find it in myself to regret what had happened. It started with a job gone wrong. We were hired to track down a stolen artifact. I don’t even remember what it was, now, but I’d taken Carver, Varric, and Isabela...

4 years ago
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Good girls dont fuck their brothers

I was laid out on my bed in my bedroom with my fingers in my pussy masturbating. What can I say? I was horny okay? My parents had gone away for the week so it was just my brother Drake and me in the house. Well...really only me. Drake is well built, muscular and hot. He has black hair that flops into his icy blue eyes, not even mentioning his six pack. Drake is always having sex with girls so it wasn’t a surprise that he wasn’t at home tonight. Sighing I pulled my fingers out and licked them....

Incest
3 years ago
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my best friends brothers

this is 100% true - names have been changed - this is my first story so please tell me how i do :)at this time i was 34Fshaven pussy5 stoneslim withlong blonde hairwhen i started at a all girls seconday school i met this girl in my class called tara we were very good friends and did a lot together, se was a really close friend who i told evrything to - except myself and her brother george had been having an on off relationship for 3 yearsit was taras 14th birthday pool party everything kicked...

3 years ago
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Trading Places Ch 1

Author’s Note: This story was originally distributed in 7 chapters. If you missed the other installments, check my author’s page. This story may not be reproduced in any form for profit without the written permission of the author. This story may be freely distributed with this notice attached, as long as no charge is made for it and it isn’t changed in any way. If it is archived or displayed, it is done so with the understanding that the author will have unrestricted access to the...

3 years ago
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Trading Places Ch 2

©June 2002 by Bob Peale ALL RIGHTS RESERVED. Author’s Note: This story was originally distributed in 7 chapters. If you missed the other installments, check my author’s page. This story may not be reproduced in any form for profit without the written permission of the author. This story may be freely distributed with this notice attached, as long as no charge is made for it and it isn’t changed in any way. If it is archived or displayed, it is done so with the understanding that the...

4 years ago
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Trading Places

We sat there on the couch and stared at the small plain package. After ten years of marriage, we had come to a point where our sex life had become all but non-existant. Don't get me wrong, Susan is fucking hot. I would hit that three times a day of I could. She blames me, but I don't see it. She says I try to hard to fuck her and that turns her off. But I went six months without trying last year....subject never came up. Its like Susan just doesn't have a sex drive. A few weeks ago I got spam...

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