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."