Sheri and Anal

It might seem odd that my brother's first time with anal was with me and not Sheri. After all, she's the adventurous one in the family. And I guess it's a little odd. It may have seemed like my brother and I discovered anal on our own, and in a way we did. But we both knew about it before we accidentally tried it, and who knows, maybe without the accident we would have done it that day anyway.

Sheri started with anal pretty much right out of the gate. I actually was lucky enough to get to watch her one of her first times. She had actually been trying out toys in her ass for a number of years, before she even had her first period. She liked penetration, and since she couldn't do that without Daddy's approval, she tried penetrating other holes instead. She was thinking, she confided in me later, that if she had to wait too much longer to get to fuck, she might sneak some cock in the back way and it wouldn't really count. I know a number of girls who feel that way, actually; I knew a girl in college who was still a virgin in her cunt but had sucked and fucked with the best of them, just in her ass. She was popular, more popular than a virgin has any right to be.

Anyway, Sheri finally was free to fuck, but she wanted to try anal right away and Dad wouldn't do it. She sought out another guy, older than her by a number of years, and told him she wanted him to fuck her little ass. You don't say no to that, especially not if it's my sister doing the asking. She came back that evening with a smile on her face like the cat who ate the canary, and she told Mari and me that it was great and she couldn't wait to try it again.

Eventually though, she wanted a big cock, not a tiny teen cock, and she kept pestering Daddy to do her the back way. He wouldn't budge. Finally he and Mom, I think to get some peace and quiet, invited a friend of theirs, call him Fred, in his 20s, to do her up right for her birthday. They'd known the guy's parents and knew him since he was a baby, and I'm pretty sure his family had a similar arrangement to ours, and that probably there had been some sharing going on. They told him they would let him give their daughter what she wanted for her birthday, but everyone had to watch, as an educational experience I guess. I think they wanted to watch to make sure he wouldn't hurt her, and Mari wanted to watch out of curiosity, and so Mike and I wanted to watch too because it was what the big kids were doing.

I don't know how many times Sheri had been fucked in the ass by then, but even her boasting was pretty low, so I imagine only a few times. She looked a little nervous. Fred had known her since she was a newborn, and now he looked really excited to get to fuck her. I bet he was one of the guys she sucked off before she was allowed to have sex. His cock was much larger than any teen boy's, close in size to my dad, or what my brother is like now.

Now that I think about it, my parents might have been trying to teach Sheri a lesson too, making us all watch. Well, not making, letting. I think Sheri was hoping that Fred would carry her upstairs or to the rumpus room, but he just grinned and pulled off his boxers and there was his cock. Mom liked the look of it too, and I know I was interested in it. It was one of the first cocks I'd seen on someone not in my family.

Sheri asked meekly if he needed her to suck him off first, and he told her no, he wanted to lube her up good if she was really serious about putting his hog in her shoot. I think those were his exact words, but I was young and I don't have a photographic or stereophonic memory. She nodded hesitantly and then bent over (she was already naked of course) and presented him with her pert little backside. He spent a long time massaging the lube all over her, trying to loosen her up. He said she reminded him of the first girl he'd ever fucked in the ass. My father asked him if she had been this young, and Fred shook his head and said Sheri was the youngest he'd ever had, period.

I wished right there that I could have let him fuck me, so I would be the youngest he'd ever had. I was going through a jealous stage where it seemed like it would be forever before I'd get to blossom. Mom just laughed and said that Sheri always had been a quick study, although whom she had been studying was anyone's guess. Porn, probably, since there was no anal in our house between my parents.

When Fred finally got Sheri as loose and lubed as he could, he got behind her and everyone crowded in for a closer look. Well, Mom and Dad stayed put, but the other kids crowded in. Fred said he wasn't sure he could handle the crowd, and Sheri said something upset, so Mom and Dad made us come back and sit with them. But we could still get a good view as Fred slowly, carefully worked his cock into Sheri's butthole.

Unless you've seen a young anus take a big cock, it's hard to describe how incredibly arousing and beautiful it is. I don't guess Mom and Dad think so, but even Mari was a little turned on by it. The head flattens out a little as it presses against the rosebud, but then (well, in this case anyway) Fred tensed himself a little and the head popped through the first barrier. Sheri moaned at that. Then Fred inched forward until it was like something gave, and Sheri moaned again and his cock slipped completely in past the muscular ring and into her ass properly.

He waited for a while, just holding her hips and letting her get used to it, then he moved a little bit further in, stopping when she moaned or tensed up. And I know it sounds hard, but he got his entire length buried in her colon after some careful pushing and pausing and petting. She was gasping. I asked her what it felt like, and Mom tried to stop me from talking to her, but Dad said something about learning being important. Sheri wasn't that coherent, but she told me it was like she had to take a massive poop and couldn't. I didn't see how that could be pleasant, but she said it was.

Fred said he didn't want to try thrusting just yet, so he reached down and diddled Sheri's clit until she screamed and panted and must have been cumming. Dad whispered to me that I should go over and feel Sheri's pussy while she came with a cock in her ass, and I took that as a compliment about how grown up I was being. So I felt my sister up while she came hard. I got a little wet on my hand, and her pussy was spasming and very hot.

Finally, Fred told her (and me) that he was going to start moving, and I took that as a sign that I should probably leave her alone. I made my way back to the couch and Daddy's lap as Fred pulled out a little and then slowly eased back in, then out and in a little faster. Pretty soon he was fucking her, slowly but surely, his strokes not very long and very slow. Dad had a big hardon under me, and when I giggled and slithered around on it he laughed and plopped me down on the couch and told me it wasn't time for that yet. But Mom knew what time it was, so she put Mike down on the floor to watch, got up, and sat on Dad's lap so his cock went up inside her. They were fucking and watching Sheri get fucked in the ass.

By the time she came again, or at least got louder again, Fred had worked up to pulling nearly all the way out and then driving back in, deep, slowly but surely. That kept her cumming for a while. I could see Mari fingering herself and Mike's face all alight with curiosity, and I wished I could have been doing something to relieve the tingle in my pussy. But other than try to diddle myself a little, there wasn't any hope of me getting a cock. So I diddled and watched.

Fred told Sheri that he was going to pull all the way out and then push back in, and she nodded breathlessly. When he popped out I could see her rosebud was opened a little from penetration, and he dribbled a little lube on it and on his cock and then eased his way back in. It was quicker that time, but she did cry out as her sphincter was breached again. He pulled back out and then pushed in again, a little harder and faster. Then he said he was close, so he would try to make her cum one more time before he lost it. He started thrusting, short, powerful thrusts with his hands on her hips and a look in his eyes which I could, even then, recognize as the look of a man who is trying very hard not to cum before the job is done.

He just made it. She gasped that she was cumming, and he grunted and drove himself as deep as he could, which drew a scream from Sheri. She collapsed to the floor and he slammed down on top of her, his large body looking like it would crush her tiny one. I saw his buttocks tense and relax a number of times, then he reached down with a finger and diddled her while she came, panting and wailing his name.

After that, he went to clean off, since no one at that point was going to do it with her mouth. Sheri just lay face down on the floor. My mom and dad kept slowly fucking, and Mari arched her back and gave a little shudder, then stopped fingering herself and smiled too. Sheri had a huge smile on her face when I went around to look at it.

We haven't seen Fred in an age and a day, which is too bad because I think he'd probably have some stories to share too. He didn't fuck Sheri again before he left; she was too tired out, and Dad had to put her to bed to soak the sheets with cum (and this scared her, but also a little blood, which turned out to be nothing, just a minor cut or something). But I'm pretty sure that he and Mom made love at least once. I don't know, it was after I was in bed. I just saw him go into her room with her, his cock all hard, and both of them looking happy. It just made me horny and jealous, and I finally, before had got to sleep, had a very tiny little orgasm (not my first). It wasn't what I wanted, but what I wanted wasn't going to happen.

Anyway, I should try to get in touch with Fred or his family. He didn't visit us often when I was younger, but when he did, he usually had a good time. He even had me once, a lot later than the story I just told. He was a real anal fanatic, and was just the kind of guy I'd want breaking in my daughter's ass because he knew what he was doing and how to make a woman happy. He could have started a service: "I'll Be Your First Anal and You'll Love It." It does make me wonder just what he and my mom did, although he can't have only done anal.