This story is about the first time I ever had sex. I thought you might be interested in it because it's a little different from most other people's experiences. After all, I planned it out and, not only that, I used a bit of blackmail as well.
You'll need to know a little about the three people who were involved in my first time; me, of course, I'm Ashley, my little sister, Tiffany, and my little sister's boyfriend, Ben.
I'm sixteen and in high school, my looks are okay, average, I guess, I do have a figure, they're B-cup for you boys reading this, and, well, I do look prettier naked than I look dressed but, I guess, a lot of girls could say that. I have short brown hair, brown eyes and a slender build.
My sister, well, how do I describe Tiff? Long blond hair, often in a ponytail, a little shorter than me, brown eyes, also B-cup, but on her they look larger because she's kind of petite with a solid body, like a cheerleader or gymnast, you know the look ... hot. She's a little sex-bomb and dresses for it, as well. My little sister is a guy-magnet and loves every second of it. Oh, she's thirteen and looks eighteen.
Ben is the guy she has currently drawn into her magnetic force field, he's fourteen and is on the middle school football team. As you might expect, he's well-muscled and very good-looking. You should see them together. Well, I have and I'll get to that shortly.
Now to sex. That's why you're reading this, correct?
Let's see, when this all started, I was a virgin, not only that, I didn't have many prospects of changing that any time soon. Tiff, well, I'm pretty sure she was doing some things with boys even before she was ten. Full sex, I don't know except that it's been a year or two, I think. Yeah, pretty young. But if you knew her, you wouldn't be surprised. And Ben? Oh, from the noise coming from her room in the afternoons after school, they're not playing dominos, if you get my meaning.
Oh, one other thing, Mom. Our mom works two jobs so she's really only here a short time before we go to bed and she put us both on the pill because, as she put it, she didn't want what happened to her to happen to us.
So, that's everybody. Now, here's what happened.
My sister often borrows things from me. Not clothes, oh, no, my clothes are far too normal for her, she always craves attention and, well, she gets it by the way she dresses. She knows she's got to wear a bra to school but the rest of the time, she's usually bare underneath her blouse or top. And, often, you can easily tell.
No, she borrows other things from me, in the case of how all this came about, it was a videotape of a concert that I had. I wanted it back one afternoon and went into her room to look for it and went to the first place I figured it would be, in the VCR. I popped the tape out with the eject button, looked at it and, no, it wasn't my concert video. In fact it wasn't labeled at all. So, I pushed it back in and hit play as I turned on the television.
My sister and her boyfriend, Ben, fucking. Naked and fucking. There was a closeup of his long, chunky dick going in and out of her as she had her legs thrown up over his muscular shoulders, a really close closeup, it was hot. Then, I backed the tape up to the beginning and watched until the end. Wow. It was so hot, so sexy, so arousing. I popped the tape out and took it to my room and watched it again as I masturbated three times.
This could have been a porn video on the internet. In fact, it was better than most I'd seen. The amazing thing was that it was shot by someone in the room with them, someone who was doing closeups, fades, all kinds of things with the camera. My little sister starring in a porn film with her boyfriend. Her really hot, hunky, sexy boyfriend.
Whoever shot the video really liked Ben's dick. They had shots of it as he stood there as the camera angled around and under and over. I kept backing it up and watching it over and over. His cock was wonderful. There was one shot of my sister jacking him off and his cum flying out that just made me so wet every time I watched it and I watched it over and over and over.
There was also a section of my sister sucking his cock. Oh, it was so hot. At the end, she pulled off him and he jacked his cock covering her face with his cum, then she licked the last few drops off. This was my thirteen-year old sister. And I'd only had my boobs felt once. And never under my bra.
I watched them fuck over and over as I rubbed and fingered myself, then I decided. I wanted to be fucked, too. And by Ben, Tiffany's boyfriend.
So, by the time she got home, I had already hidden the tape. She was in the kitchen when I told her.
"If you go looking for that tape of you and Ben fucking, I've got it. Just so you know."
"What the fuck do you mean, you've got it. It's mine. It's pretty hot isn't it, aren't we a pair? It's a great fuck-tape, the best I've seen. Bet you got off to it. But it is mine, you know."
"Well, it can be your's again if you agree to something."
"Oh, shit, what's this, blackmail?"
I laughed and said, "Well, no, more like white male, the white male that's in the video with you."
"Ben? What about Ben?"
"I'd like to borrow your boyfriend so he can do to me what I've watched him doing to you."
"You're kidding. You want Ben to fuck you?"
"Yeah, that's about it."
"Sure, shit, what do I care. That's just more practice for him so he gets better at fucking me. And, believe me, Ash, he's a great fuck. I should know."
Well, I knew she was right about that, I'd watched the tape.
"Well, he's coming over in about a half hour and, well, sure, I'll tell him he's got a little extra pussy coming his way. Knowing Ben, he won't mind a bit. I'll tell you one thing, the guy can cum and cum and fuck right on like nothing ever happened. He's got a cock that just won't quit. You'll love him."
We agreed that I would go to my room and wait and while I did, I watched the video of Ben and my sister.
Just after seeing his cum spurt out the end of his cock, there was a knock on my door so I jumped up, turned off the television and opened to let Tiffany in my room.
She was wearing Ben's mesh football jersey and nothing else. It really didn't quite cover her pussy.
"Well, you got yourself a fuck, Ash, Ben's in my room, should I send him down?"
I nodded and she left. In a minute, Ben arrived at my door looking in.
"Hi, Ashley, you wanted to see me?" he asked looking more nervous than I would have expected. He was standing there in just a pair of white briefs which were wonderfully bulged out.
"Yeah, come in," I said as I closed the door behind him.
His body was fantastic, muscled, firm, tan.
"Did Tiff tell you what I wanted?"
"Yeah, that's fine with me," he said. "Should we get naked?"
I nodded and before I did anything, he was standing there, his briefs on the floor with his long, thick, brownish-pink cock standing straight out pointing itself at me as I pulled off my tee and got my bra off.
He stepped to me and took my breasts in his hands, bent over and kissed each one as I stood there, slightly shaking. Then, his lips went over my nipple and he began to suck as he slowly led me to the bed where he sat down and he sucked one and fondled the other.
I had never had my boobs sucked before and every pull sent a warm jolt right to my pussy. And there were lots of sucks. Then his hand left my breast and went down my stomach to rub softly as I felt myself get wetter and wetter.
Soon his hand moved down onto my shorts and on down to my thighs. Then his finger traced back up between my legs and pushed up under the hem and felt around working itself up under my panties as I stood there. He was looking up into my eyes as his finger sought out my pussy which didn't take long at all.
As I stood there, I moved my legs apart, then I felt the first time I'd ever had any part of another person's body enter me as his finger slipped inside. He began to slowly wiggle it as he rubbed around in me, it felt really good.
"Mmm, oh, Ben, your finger, it..." than I felt it go in a bit further and rub the walls of my pussy.
He moved his lips to my other boob and began on that one as he continued rubbing me inside.
"Mmm, oh, oh, it feels like ... oh, UH, UH, AYYE, AYYE, UH, uh, mmm, oh, ooh," I groaned as I trembled standing there as he brought me into my first orgasm from another person. Oh, it was so good.