I have a sister who's three years older than I am and when this all began, I was fourteen, just. She was seventeen and a junior in high school.
So, when she came in my room one afternoon after school and asked me, "Do you know Bryan Deering? He's in your eighth grade class, right?" I told her that, sure, I knew Bryan and asked why she wanted to know.
"Oh, I just wondered. If I wanted him to come over after school sometime, would you ask him?"
Was this weird? I thought.
"Yeah, I guess. Why Bryan, do you know him?"
"Not exactly. I know who he is, I've seen him. Well, would you?"
"You want me to see if he would come over after school? To see you?"
She said yes and I told her I'd ask him, just tell me when. Then she said, "Could you call him and ask him to come over tomorrow, after school?"
Well, I did agree though I thought it was pretty strange but my sister can do some loopy things sometimes.
I called a friend of his and got his number, then got him on the phone and told him my sister wanted to see if he'd come over to our house the next day.
Well, obviously he asked what she wanted to see him about and I told him I had no clue. Then, surprisingly he said, "Sure," and that was it. I told her, asking again why she wanted him to come over and she mumbled something about 'mutual friends' and left it at that. Weird.
The next afternoon, I was up in my room when I heard the doorbell ring and my sister go clomping down the stairs. I didn't want to even go out and see him, I was just too weirded-out by it all. He's fourteen, she's seventeen, what on earth would interest my sister in some boy my age.
So, her door was closed the whole time he was there and when I came down for supper, my parents were home and Bryan seemed long-gone.
I wondered if she was interested in him as a boy. He was cute, taller than most of the boys in my class, but he was pretty shy, too. Lots of the girls liked him, after all, he had wavy blond hair and these deep blue eyes but, like I said, he was shy and seemingly uninterested in girls.
But then, the next afternoon, I heard the bell again and peeked out to see them going in her room again. What the hell?
So, I made a few passes by Anna's room, my ear cocked for any clue of what was happening inside and it was totally silent except for some music.
I stationed myself downstairs and when, about five-thirty, they both came downstairs, I said hello.
"Oh, hi, Eileen, how are you?" he replied, smiling.
"Fine, I didn't know you knew my sister," I floated out there trying to find out what was up with my sister's interest with this boy from my class.
"Yeah, um, I'm helping her with math, I'm pretty good at math, you know," he said as she ushered him out the door. This was weirder and weirder. Then, the idea hit.
I went out to the garage and brought the folding ladder up to my room and put it up to the heating vent near the ceiling and looked in. There was an identical vent opposite that was in Anna's room, so I unscrewed the vent grille on my side and got a mirror.
When I climbed up again, I held the mirror at an angle and there was my sister's room all laid-out beneath me. Now I would know if it was math or something else.
I put the ladder under my bed and went about the rest of the day trying not to think about my sister and Bryan.
The next afternoon came around and when I got home, Anna was already there. I had a snack and went up to my room to wait. Of course, this would be the day when Bryan came later, driving me nuts. But I did hear the doorbell and then got the ladder set up and the mirror ready.
I waited until I knew they had to be in her room, then slowly, silently, I eased myself up, tilted the mirror and saw what they were doing.
It sure wasn't math. You don't need to be naked to do math. He was down on her bed as she straddled him going up and down on top of him. They were fucking like crazy. I had planned on just taking a quick look to see what they were up to, then getting down and doing my homework for the next day.
Oh, I wasn't going to miss this, though, it looked so hot and sexy, his hands were on her boobs, she had really nice ones, bigger than mine, of course, and she was bouncing on him like she was in a rodeo. So, I stayed on the top of the ladder until I saw them both finish. They were quiet, I guess trying to hold it back, but she was soon down on him kissing him over and over.
Then, she moved off him and that was the first time I could really see Bryan naked. Wow, it stood straight up in the air, long and thin.
Now I watched it disappear again, this time into my sister's mouth as her head bobbed up and down over him. My god, she was giving him a blow job.
Then the full import hit me ... my seventeen-year old sister was having sex with a fourteen-year old boy, a boy in my eighth-grade class. She was a junior in high school, a senior next fall.
I was barefoot on the ladder so now my feet were hurting but the scene below in my sister's room was so exciting I couldn't stop looking. I did take the mirror away for a few minutes at a time, not wanting to get caught spying, but every time I looked, I felt a twinge in my panties it was so sexy.
I had to get down and go pee at one point but when I got back up in position, Anna was flat on her back with her legs over Bryan's shoulders. God, he was eating her out. Oh, did that look good.
I have a friend at school, Becky Friedlander, who told me all about how it feels to have a boy do it to you, she made it sound like the best thing there is and when I asked her who the boy was, she really clammed up.
Who it is wasn't important, she told me, it's how he makes me feel when he gets me off this way.
She really made it sound so good and I kept asking her who the boy was and she finally told me ... it was her older brother. Really. Wow.
So here's my sister getting oral sex, getting eaten out, by a boy from my grade at school. And I was watching.
My own experience with sex was, like with so many girls my age, just what I'd done myself with my fingers. It was pretty good but the way I saw my sister writhing and twisting, I knew there was lots that was better than playing with yourself.
This was even more intriguing than when they were fucking. I could just see his tongue flipping around on her and how it was making her tremble and shake. Oh, did this look hot.
I watched on and off until they began getting dressed. I quickly put the ladder under my bed and changed my panties, they were soaked along the inseam, and snuck down before they came out of her room.
"Hi, Eileen," Bryan said as they came in the kitchen where I was eating cookies and reading a book. I said hi back and saw that his hair was kind of mussed-up and that his pants were rather poked-out. But there was little chit-chat before she ushered him out the front door.
Then, she came back in and took a cookie and sat down.
"You and Bryan are pretty good friends now, huh?" I prompted.
"Um, yeah, he's a nice kid. Really knows his math. Big help," she said as she twisted the chocolate cookie apart and began to lick the filling.
"I know what you two are doing, Anna."
She looked at me, furrowing her eyebrows asking, "You do?"
"I took the vent off in my room and got up and looked in your room when you were up on him fucking him. Is he good?" I asked with a grin. It's not often that the younger sibling has the upper hand, I was loving it.
"Shit, you were watching us? From that grill up by the ceiling? How could you reach it?"
"The ladder. It's under my bed right now. You two sure have fun."
"Okay, what do you want? You want to blackmail me, don't you?"
"Not at all. I was thinking it might be fun if I could have Bryan, too?"
"You're not on birth control, are you?"
"No, but maybe you could maybe ask Mom if I should now that I'll be going to high school. When did you start?"
"High school. Um, yeah, I guess I could. I'm not on the pill, though, I get a shot every three months instead. So there's no pills to take. So you want Bryan, too, huh? He's really cute and, oh, can he give oral."
"So I saw. You really love that, don't you?"
"Just you wait, Eileen, just you wait. And he fucks like a little rabbit. He just doesn't ever stop. But I do have some condoms if you want to try them. I guess I don't mind if you join in. You'll find out just how good sex can be. My eighth-grade boyfriend is a little sex fiend, you'll see."
"Yeah, if you have condoms, yeah, I'm in. Oh, god, I never thought I'd be having sex like right now, I figured it would be sometime in high school. So, can I join you two tomorrow, is he coming tomorrow?"
"He comes every day, the boy just loves sex. He'd never done it before I asked him over. I was his first fuck ever," my sister said rather proudly.
"So, why did you pick Bryan, how did you know him?"
"I didn't. Susie Wilman's brother helps coach his soccer team and told her he's got the biggest dick he'd ever seen on a kid his age. So, when Susie told me, well, I knew I wanted to sample it. It is nice and long."
"You're a whore, big sister, simply a slut."
"Yep. You got it. But I'll tell you the kid is a fuck machine. And, unlike most boys, he's not hair-trigger, either. Even his first cum takes a long time. I can usually get off twice before he does once."
"So, I guess I'll get my chance with him tomorrow. I didn't think my first time would happen in the same room with my sister, geez."
"I'll leave if you want, I don't mind."
"Well, in a way it might be nice to have you there. Does it hurt a lot your first time?"
"Nah, do you have any dildos?"
I laughed, every time I heard the word, it just sounded so funny.
"No, I've used one on a sleepover at Judy Rasmussen's, she's got a collection you wouldn't believe. Her sister in college gave her a whole drawerful."
"Why don't I give you my biggest one and you can take a nice long bath with it tonight? Just keep quiet, okay?"
So, I took the huge-looking thing and wondered just how I was ever going to get that thing up inside me when my sister, sensing from my bewildered look added, "Don't worry, take it slow, it'll fit, just take your time. And don't scream."
My eyes got big when she said about screaming so she quickly appended, "Scream in pleasure, Eileen, when you cum. It'll really get you off. You'll see," and I walked out of the kitchen as she grinned at me.
I did take a long, hot bath and, yes, it
did fit, though it took a while. I sure wanted to scream in joy, both times, I almost let it out. I finally just laid there, my body from the neck down immersed in the cooling bathwater, the dildo still deep, I was almost comatose from the ecstasy of my masturbation. If this was so good, what was tomorrow going to be like, I wondered.
I pulled the dildo out, suddenly making me feel so empty and nudged the drain lever up letting the water flow out. I still was in the tub, almost too weak to get out. But, I was getting chilled and got out and dried off, slipped on a nighty and went off to bed.
I did sleep, I know I did, but I also knew what my morning was bringing as well. Anna had told me that Bryan was due at our house at nine and, as far as he knew, it was to have sex with her, just her. I would be the surprise. It was a teacher-conference day, so both our schools were off and we had the whole day for my introduction to sex by a boy that my sister trained herself.
I agreed that it might be a good idea to keep it from him until the last minute in case I decided to back out even though I surely didn't think I would.
The bell rang exactly at nine and my sister got up, saying, "Oh, my hot little eighth-grader is horny this morning, right on time. Wait until he gets you, too," and ran off downstairs to let him in.
I was so excited and nervous, I mean this was it, I was going to let a boy put his dick inside me. Omigod.
Anna brought him right into my room.
"Hi, Eileen, how are you?"
"Um, pretty good," I answered hesitantly, glancing to my sister for help.
"I told Eileen what we've been doing and she wants to join our fun. Is that okay, Bryan?"
It took a second or two for him to answer making me wonder if he might possibly back out but that just shows you what I knew about boys at that stage of my life. I was to learn lots more from then on.
"Yeah, really? Both of you? You really mean it?"
"We really mean it, Bryan, and it will be Eileen's first time, okay? So you'll need to go slow and if she says stop because it hurts, then stop, okay?"
He said he would, then Anna told him, "Why don't you undress her?" and he stepped to me and reached down and pulled my teeshirt up off me, then put his arms around and rather expertly, I thought, undid the hooks of my bra and slid it off my arms.
"Oh, you're really pretty, Eileen, just beautiful," he said making my heart flutter. It was the first compliment I'd had about my body and it made me feel pretty good, sexy, too.
"She is pretty, I'm sure she'd want you to touch them, kiss them, you know, like you do mine."
This boy from my class, the one that I, unknowingly, recruited as a sex partner for my older sister, now sat on my bed and leaned forward as I watched his lips suck in my nipple while my heart raced underneath. His lips began pulling and each suck sent a pulse, a throb, right to my pussy. His hand moved up to feel my other boob as I stood there, just beginning my sexual life as a female, now, wanting to only go forward, it was just too wonderful.
"Don't you just love your boobs sucked, Eileen? And this is just the beginning, this is coming," she said, holding up the condom. "And he's great licking you out. Do that next, Bryan, eat her out, let her see how good you are. Go ahead, get down on the bed and spread open for him. He's really good."
I did just what my sister urged and he pulled off my shorts, then panties which were already soaked. I squeezed my eyes shut until his tongue touched me there, wiping up and back along my slit. Then my eyes popped open as I sucked in a gasp of breath, startled at the exhilaration rocketing across my nervous, tingly body.
Oh, this was heaven. I had never felt anything like this, nothing in the world. I'd never even known anything could feel this good. He was flicking his tongue up and down, then poking it in and swirling it around, followed by little sucks.
"Omigod, this is awesome, oh, my pussy's never, ever felt like this. Mmm, oh, right there, Bryan, right there," I gasped.
"Get her open, Bryan, use your fingers like I showed you," my sister urged and I felt his fingers gently part me as he flipped his tongue even deeper.
What was good before became sensational and intense as his tongue dug deeper in my most intimate place. It was glorious and I simply could no longer keep in control.
"Oh, OH, OH, OMIGOD, UUH, UUH," I screamed as my body shook and shuddered while wave after wave of exquisite feelings rippled back and forth across me. I knew I would never be the same.
"Omigod, that was unbelievable," I gasped as I pulled Bryan up to kiss him over and over. "I knew it would be good, but, wow, that was incredible."
"Oh, this will be better, Eileen," my sister said as she held the condom package over my head.
"Are you ready, Eileen?" he asked as he knelt up, his dick hard and straight while my sister put the condom on him. All I could do was nod and he wiggled up and put the floppy tip between my legs and began rubbing it up and down while he pressed against me.
This was it, I thought, sex was here and I was doing it and there was no turning back as I felt him begin pushing.
It wasn't hurting, there was just the feeling of pressure against me, then, rather suddenly, I felt him enter, just the tip end, it seemed, not hurting, just feeling enlarged, full. Then more came inside me as he kept pushing and then I realized that his body was pressing tightly against mine. His dick had to be completely inside me now.
It was the movement back out that began to feel so good, then inside again, back and forth. Oh, this was it, this was sex. I was doing it. And it was wonderful.
I loved his hands on my boobs as he moved up and down over me, it felt so good being made love to, I knew this would be something I would want the rest of my life, it just made me feel so good.
He was now taking nice, long strokes in and out of me just making my whole pussy, all the way deep inside, feel wonderful. My sister had moved up next to us and her hand was rubbing my stomach, maybe trying to calm me but I wasn't needing calming so much, it was thrilling.
"Is it good?" she asked softly.
"Oh, just wonderful, Anna, it feels incredible, better than anything."
"Mmm, feels good to me, too. You both are so hot and sexy. I can't believe you're letting me do your sister, too. I couldn't believe it when you had me over that first time for sex, I just had no idea why you wanted me to come to your house, then when you said you wanted sex with me, well, now, I get your sister, too," he gushed.
I looked up at my sister and asked, "Why did you want Bryan? Why him?"
She laughed and said, "Well, I told you I'd heard about his cock and that he was pretty big for an eighth grader. I knew you must know him, being in the same grade and I didn't think he'd had sex, so I wanted to train him myself. Right, Bryan?"
"Right. Oh, she trained me all right. She told me she was sick of boys who just fucked to get themselves off, never caring about the girl. 'I'm gonna make you different, ' she told me. And she's a great teacher."
"Tell her what else, Bryan. Tell her about your sister. Go on."
"Yeah, after I got really good at giving oral and could hold off a long time when we were fucking, she told my sister how good I was and I started doing her, too."
"You're having sex with your sister, too?" I asked, rather astonished at all the sex this fourteen-year old was having.
"Yeah and a cousin that my sister told."
"So it's four girls now?" my sister asked him.
"Yeah, but, Anna, you're my first one and you trained me good. Look at what you've done for me," he said, nodding down at me, as his cock went in and out so deliciously, "I'll always be with you as long as you want me."
"Isn't he sweet, Eileen?" my sister said. "And he fucks like a man."
That I wouldn't know about and her comment made me wonder if she'd had sex with a man ... or men. I was finding out that there was a lot I didn't know about my sister, especially about what she'd done in sex.
It was sure exciting that I was now getting my beginning in sex. And, while I didn't have anyone else to compare him with, I was sure liking Bryan Deering for sex. He felt so good going in and out of me, fucking me; oh, when I first started hearing that word, fucking, I thought it was so nasty but now It just sounds wonderful, just like it feels.
"I don't know about that but, Bryan, you sure do it good," I moaned as it felt better and better.
"I trained him, Sis, I trained him so good, he's just the best. And, he's fourteen. And he's fucking four girls now. He'll do anything I want him to, he knows I got him all this, more pussy than an eighth-grader even dreams about. And he's fucking us all."
"Your sister's right, I'd do anything for her, anything. I know when I've got a good deal and Anna is fabulous. She can keep me forever," he blurted out, "I'll really do anything she wants."
"Yeah, he likes me to tie him up to my bed and tease his dick for hours, don't you, Bryan, you little pussy-hound?"
"I love anything you do to me, Anna, and your sister can have me any way she wants, too. Even both of you together, that most of all, I'd love that. You know I can't get enough sex. It's the way you made me, Anna."
Well, not only was I losing my cherry quite wonderfully, I was learning a lot about my sister's young boyfriend, how she's got him doing whatever she wants. Now including fucking me. Wow.