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A Look Back

Posted by: Age: 20 Posted on: 11 comments
17 likes 44 views Category: Masturbation Male-Female Tags: sister, caught, sleepover

Just a few of the moments my sister or I were caught in comprising situations.


Ever since this virus started and my school stopped classes (online classes just suck by the way), I've been back at home, both bored and generally frustrated. It's me and my parents, and that's pretty much it. I talk to friends all the time, but for the most part it's total isolation, so I thought I'd shared some stories from years ago. Maybe you guys will like some of them, I don't know, but it gives me something to do, and maybe think back and laugh on.

I mentioned in my other story that I lived most of my life sharing a room with my older sister (I'll just call her Amanda, though that's not her name), and so finding some time to myself when I was in a horny mood wasn't always easy, and I was that way a lot when I was a teen.

My sister and I have a pretty good relationship, I think. She's a couple of years older, so when she started dating (not to mention going through puberty and actually getting boobs), I was jealous, but I got over that after a little. We've never been open about sex, though - for some reason, we can't really talk about that kind of stuff without feeling uncomfortable (I have other friends with sisters who have no problem with that type of conversation, so I'm not sure what it is).

Because it's something that neither of us have really been open about, we've both found ourselves in compromising situations before. I caught her a handful of times (and heard her when she was doing it, trying to stay quiet, a lot more times), and vice-versa. I just wanted to talk about some of the times that stood out most.

Before I get into it, though, I just want to make clear that while I'm bisexual, I've never been attracted to my sister. She's sort of cute, I guess, but the whole thing would just be beyond strange, so these memories stand out because nowadays I can look back at how embarrassed we were and sort of have a laugh. I know some of you might look more into it, but this isn't that type of thing.

I won't pretend to know what gets my sister off. I know she's straight (though she can't date a guy longer than a year to save her life), and I definitely haven't thought much about her 'me-time,' but the times I caught her, she seemed to be sorta involved.

What I mean by that is when I'm horny, I don't really want to draw it out. I might pull my short, jeans, pajamas, whatever down, and rub it off. I've dated girls who like the foreplay, though, and getting more into the mood. I'll be blunt and say that I've not used any toys that much (tried a dildo and a butt-plug, but that was more for my partners than me).

Amanda did, though. Before I ever caught her, I found a small dildo in her dresser drawer. I can't remember what age I was, but I knew what it was, and was a bit shocked that she had one (I can only guess she got it from a friend of hers, but I never asked her). I remember my face was on fire, and quickly put it back. I don't really remember what I was digging through her drawers for now, but that discovery jilted me.

It was maybe a few weeks after that when I realized that she was just as horny as I always felt, but hid it better or something. I've never really been overly shy, but Amanda sorta dressed more conservatively and definitely didn't seem the type to be sex-crazed. Apparently she was, but it took me by surprise.

I'd heard her masturbating before, just light moans and whimpers, usually long after we were supposed to be asleep. I guess that she waited until she thought I was asleep to start in, which really sucked because I was trying to do the same thing. I never mentioned anything too her (talk about an awkward conversation), but it happened more than a handful of times.

Two occasions stand out when it comes to catching her. I was over at a friend's house, came home later than expected (I almost stayed over, but went home in the end), and when I stepped into our room, Amanda was stark naked besides a pair of socks, and lying on her stomach, one of her hands between her legs.

Her butt was in the air, her legs were spread, her head on a pillow, fingering herself in a frenzy. She was gasping quickly, and didn't hear the door open, but she did hear my say "oh my God."

Quicker than you would believe, she spun around in her bed, almost falling off, and pulled the pillow she was lying on over her boobs. I was still very taken aback, and was sorta frozen. She was blushing more wildly than I'd ever seen (and I guess that I was too), and I just managed to get a hold of myself and backed out of the room, and went to sit on the couch.

Seeing her like that didn't traumatize me or anything, but I'll be honest and say that it took me a little bit to really wrap my head around the fact she did that. Like I said, she was always the more conversative dresser, so seeing her in that state just weirded me out.

I sat out there for like 30 minutes before going back to the room, and I knocked, which was something I don't really think I've done before. She opened the door, her face still uber-red, dressed in her nightgown. She mumured something (and to be 100% honest to this day I don't know what she said), and went to bed. I wanted to say something, but I never did, and it wasn't until later that we even really broached the subject.

Flash-forward a few years, she's  dating her third boyfriend, I think. I don't think the two of them ever went all the way, but I know that they both got each other off, though I think that mostly happened over at his house. After one of her dates, like she called them, she got back and I could tell instantly that she still felt antsy and turned on. Her face was flushed, she couldn't keep focus on anything I was saying, and was zoned out.

She didn't ask for me to leave, but I understood that she probably wanted me out of there, so I took an impromptu shower which I figured would give her enough time to take care of it, but of course I was wrong.

Like I said, she seems to get more involved then I usually do. If I were in her shoes I woulda done it as soon as she left, but like 25 minutes later, I walked in on her again. This time I got a bit more of a look, cause she had headphones in and was listening to music, which I don't understand why she'd do, but whatever, so it took her longer to react.

She was on her back, again wearing only socks, with one hand between her legs and her other rubbing her tits. In the time I had, I also saw that she was really wet and that dildo I mentioned earlier was on her bed, bumping into her leg as she kept going at herself. Again, my face instantly on fire, but she didn't hear me at all, and just kept at it. I wasn't as shocked as before, but this was only the second time I saw her in that situation, so it still took me aback.

I remember clearly thinking about just walking back out the door like I'd never been there, but before I got that option, she had apparently opened her eyes was was suddenly hissing at me "get the hell out!" I quickly did as she asked, but instead of running to the couch (I was still in just my towel), I wait maybe five minutes and knocked, then went back in.

Amanda was definitely angry, and glared hard at me, but I was sorta pissed too, because she had enough time to do that while I was in the shower, and I wanted to get changed. I didn't want to fight with her, though, so I just said, trying in a casual manner, "Guess I should have taken a longer shower."

She uncharacteristically snorted at that, bit her bottom lip, and nodded. I thought that might be the end of it, but she said "I sort of lose track of time when I, y'know, do it" (I remember very specifically she just said "do it", and she was blushing super hard). I mumbled back a reply, probably "I know, me too," and again, without any fanfare, we swept it under the rug.

She caught me only once (not counting the times I bet she heard me before falling asleep), and that's cause I didn't even know she was home. When she went off to college (in-state, but still a three-hour drive away), I felt sorta lonely, but I got used really quickly to having the room to myself. It was during that time I really started trying more things and sometimes even brought people home (my parents knew about some of the guys, but never the girls). There's some memorable things that happened during those times, but the point is that I was finally free.

I don't remember clearly what got me horny, but my parents were out somewhere, it was the middle of the afternoon on Friday, and I had the house to myself. I didn't even bother shutting my door, to be honest, and just started rubbing myself, working myself up.

It didn't take me long to get super aroused, and by that point I was wearing only a pair of panties, and leaning back on my computer chair, legs spread wide open and knees apart, fingering myself. My panties were already soaked, and were wedging up in my butt, but I really wasn't in the mood to stop what I was doing to take them off.

Never once did I hear a car outside, and I didn't hear the front door open. I was completely in my own world, and I never even sensed I was being watched I heard a loud knock and, my eyes flying open, seeing Amanda smirking at me from the doorway (which, because of course, was the way I was facing).

I wasn't done yet but I leaped out of the chair and turned around, and though Amanda was definitely flustered, she didn't walk away. Instead, she said, my back (and bare butt, but my ass didn't concern me), "I'll give you ten minutes, Bailey, and when I'm back, try to be dressed."

I heard her walk away after that, and though I tried to finish, my heart wasn't in it, and I just gave up after like six minutes. I was so frustrated, but I didn't blame her once, because I knew that I'd done the same thing to her. After I got dressed (barely - I remember just pulling up some shorts and grabbing a tank top, my tits still uber sensitive), I went out there and though she joked a little about it, we just left it alone.

The last story mercifully doesn't involve my sister, but a friend of mine back in high school (and in fact one of the girls from my first story). It was another sleepover, but this time just the two of us. This was maybe a year after that other sleepover, and I had a little more experience and adventurous. She and I never really went far (though we had kissed each other before and maybe touched each other a few times), but she was definitely cute (she had a pixie-cut, and with her smaller boobs and cute butt, always drove me wild the times we changed together).

I got to her place around 7:00, and we spent the first hours just talking and watching a movie. Sometimes she'd swat my butt (she was jealous of it), and I'd tease her about her boobs, but we were just goofing off, nothing serious. When it came time to change into our pajamas, I took special notice watching her while I changed myself (at that time it was just a t-shirt and panties, so it wasn't anything that i had to focus on).

She was shy when I met her, but we'd seen each other naked enough times by that point that she was barely even hesitant to undress in front of me, and watching her pull her shirt off, or her underwear off, it really got me going. My nipples are pretty small and pink - she was darker, so her nipples were an almond-ish color that I absolutely loved. When she was bending over her bed to pick up her pajamas, and her butt was sticking out, I felt ready then to finish off.

Instead I just watched and, for a few seconds, put my hand to my panties, and I shuddered loudly. She heard, turned and asked if I was fine, and I just said yes. My t-shirt was thin, and I knew that my nipples were sticking out, but she didn't mention it, and I just wanted to lie down and actually get off. If I was lucky, maybe even with her.

It didn't happen that way, though. Both of us slept in the same bed, but she was out pretty quickly after lying down, and my desire to finger myself was beyond control. I waited as long as I could, and, as smoothly as possible, slid my panties down and quickly rubbed myself, trying to keep my motions as smooth as possible. I had never licked her pussy before, but I was imaging doing just that, my heads on her inner thighs, holding her down, and an explosive orgasm just ripped through me.

Her bed and my panties were soaked, and I was trying to breath deeply and slowly during it all, but she woke up anyway and, without saying anything, reached over and tweaked one of my nipples, and though not nearly as powerful, I came again, my butt wriggly wildly on the bed.

She laughed a drowsy laugh, said that she hoped I had fun, and without anymore, fell back asleep in pretty quick time. After that, I cleaned up as best I could, and when I mentioned it in passing the next morning, her hand flew to her mouth and she gasped, because she didn't remember it at all. She was still half asleep.

I blushed at that, and told her quickly what had happened (she insisted before I gave in), and we both eventually laughed at the whole thing. I lost track of her after I went to college, but though she wasn't anyone I really did that much with, I always remember that one moment we shared.

I know there's nothing really special here, but I wanted to share these moments anyway, and maybe others have had other embarrassing moments like this who can relate.

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