It Started with my Sister's Toy

I had a part time job at a local pizza joint, usually evenings with some afternoons if they were busy. It wasn't a great job but I'd moved back home from university for the summer and one of the conditions was that I get some sort of a job to at least cover my own expenses and help a bit with food and stuff.

It was good to be back home with the only real issues being I had less privacy than I was used to and my younger sister still lived at home which meant I had to deal with her. Over all, we didn't get along too badly but over the last year, I'd gotten used to being able to walk to the bathroom with just boxers on or sometimes nothing because my roommate spent a lot of his time at his girlfriend's place. On the up-side, she often had friends over and seeing as I was 21 and she was 19, I had no problem enjoying a peek or two at a well-built girl in tight shorts and a tank top.

One Monday, I wasn't working so had gone out for some supper and a beer or two with a couple of buddies for a beer and got home about 10. Mom and dad didn't really like me going out too often, they didn't care much if I drank but considered it a 'waste of money' and preferred that I just had a drink or two at home but I knew they were out for the evening so I'd be home before they were. I'd hardly gotten in when she said, "Kirk, what the fuck were you doing in my room?"

She didn't usually swear so I knew she was really upset. I was going to deny it but then she held up a vibrator and said, "Maybe more importantly, would you like to explain what the fuck you were doing with this?"

Oh fuck! So much for denying that I'd been in her room because now I remembered that I'd forgotten to put it back from the night before. Even as I was trying to come up with an answer, she waved it in front of my face and kept going. "Never mind! Seeing as it was in your room but I know you didn't have anyone over recently, it still has lube on it and it smells like ass, I'm pretty sure that I know what you've been doing and where it's been."

Double fuck! As much as we got along, we'd also always enjoyed getting the other one in trouble and even though I was 21, mom and dad were really strait laced when it came to sex or even talk of sex so if she told mom and dad, I'd be totally screwed and possibly kicked out.

"So, are you gay, bi or what?"

I took a deep breath and said, "No, definitely not gay or even bi, I was watching porn one night at University and one of the vids was a guy using a toy on himself. I'd had a few drinks so I watched it and found it turned me on a bit. That night when I was masturbating, I played with my ass and found it actually felt good and I've played with my ass somewhat regularly since then. A week or so ago, I was looking for that CD you borrowed and found that vibrator in your drawer. I know I shouldn't have but when I saw it, I wondered what it would feel like so I grabbed it to play with it later and it felt really good. I made sure I washed it well before I put it back. I grabbed it again yesterday but forgot to put it back."

At first, I really couldn't tell from the look on her face whether she believed me, was pissed or even cared. Then she looked at me and said, "Ok, just so I've got this right, you have no interest in guys what so ever but you enjoy the feeling of something in your ass. You weren't satisfied with just a finger or two so you decided to grab one of my toys without permission and fuck your ass with it. Am I good so far?"

By that point, about all I could do was nod.

"Ok, how many times have you 'borrowed' it?"

"Three times."

"Ok, so now I've got to decide whether I should let mom and dad know that you were in my room without permission, took my vibrator and that their son enjoys sticking things in his ass."

Shit, I knew she was going to go there and now I'd either end up in more shit than I'd ever been in so far with my parents or end up groveling to my younger sister not to say anything. I was just going to ask what it would take for her to forget the whole thing when I had a thought.

"Sure, you'd get me in lots of trouble but then you'd have to admit that you had a vibrator in your room and you know that even though it wouldn't be as bad, dad would still freak out about that."

"Oh, I thought of that already and figured I could just get in trouble for telling them I went into your room to find something of mine and found this laying on the floor. Of course, I'd tell them I never saw it in my life before so you must have brought it with you from university."

Shit, she'd already thought it through and her story sounded totally plausible.

"So that takes me back to whether or not I should tell mom and dad. Do you know how good it feels to pretty much have your fate right here for me to decide? You need to come up with something really good if you want me to stay quiet about this."

"Like doing your share of the laundry and cleaning for the rest of the summer?"

Kirsty just laughed and said, "Well, that would keep me quiet about the 'coming into my bedroom without permission' part and I could even make it worse by saying I found a pair of my panties in your room with the vibrator and make you sound like a total perv."

By now, I know I was sweating and blushing even though I felt cold plus I had a feeling she already had something planned for me but was making me wait before she told me.

When she looked at me and said, "Aww, don't worry big brother, do you really think I'd tell mom and dad and get you in that much trouble?" I knew she realized there wasn't much I wouldn't do to keep it all quiet.

"Follow me, I want to show you something."

I wasn't sure what she wanted to show me but I knew I didn't have much of a choice so I followed her into her bedroom and sat where she pointed on her bed. She grabbed her chair and turned it toward me. "I've been thinking of something for a while and you just made it a whole lot easier for me so I guess I should thank you. Do you think that genes play any part in things like people's sexual preferences or foods they like?"

Her question caught me totally off guard so the only answer I could give her was, "Huh? I never really thought about it."

"Well, it'll make sense in a minute" and with that, she pulled a USB drive from her pocket and put it into the laptop. "Let's see what you think of this..."

She clicked on the USB drive and then opened one of the files. As soon as it opened, her screen was filled with a video of a guy laying on a bed, on his back while a woman wearing a harness and strapon slowly eased the head of it into his ass. It was definitely bigger than the toy I'd taken and obvious that at first it must have hurt a bit going in but once it was in and she'd given him a few strokes, he seemed to be enjoying it. As soon as that clip was over, she opened up another one and this time the guy was bent over a couch while a woman fucked him from behind with a couple of different sized strapons.

She went through a few more that were all similar and by the time she was done, my cock was throbbing from watching them. "I was going to ask what you thought of them but the bulge in your pants tells me you enjoyed them."

"Wow, you're really going through a lot of trouble to totally fuck me over, aren't you? How are you going to explain 'accidently' finding those on my computer?"

"I'm sure I could find a way but that wasn't what I was thinking. Remember when I asked if things like sexual preferences were genetic?"

"Ya, but I still don't see the connection between that and you downloading these videos."

Kirsty took a deep breath then said, "First, if you ever tell anyone what I'm going to tell you, I'll totally deny it and I'll make sure every one of your friends knows that you like shoving vibrators in your ass."

"Ok, I got it. Now please explain what the connection is between genes and those videos."

After another deep breath, she looked at me and said, "I didn't download them to get you in more trouble, I've downloaded them because I think they're fucking hot and would love to try it but never found a guy that would even let me finger his ass so using a vibrator there wouldn't even be a possibility. However, now that I know you like something up your ass and you don't want our parents to know what you've been doing, maybe we can help each other out."

Finally, everything clicked into place and I knew exactly what she was thinking and had been planning. "So, if I let you do to me what's in those videos, you won't say anything about it to mom, dad or anyone else?"

"That's exactly what I was thinking. Do we have a deal?"

Fuck, now that I knew what she wanted, things were a lot better than I'd expected. I'd already masturbated pretending it was a woman using a toy on me and I'd just found out that it was something my sister wanted to do. Hell, even without the 'incriminating evidence', I'd likely have let her try using a vibrator in my ass. The catch was going to be that I had to agree without sounding like I actually wanted to do it.

Doing my best to look like I didn't have much of a choice I said, "I enjoy it when I do it myself but I'm not sure I want anyone else doing it and really don't want that 'anyone' to be my sister, that would be whole new level of 'wrong' so no, I don't think so."

"And the other option is?"

With a deep sigh to cover my excitement, I said, "Well, ok but it's a one-time thing, right?"

"Well, you 'borrowed' it three times so I think it would be fair if I got to try it with you three times."

Hanging my head so it looked like I'd given up, I mumbled, "When?"

"Well, seeing as mom and dad won't be home for a while and I'm horny from watching those clips, how about right now?"

Again, I tried to sound like I really didn't want to do it with, "Ok, might as well get once over with."

I hadn't seen Kirsty look that happy since Christmas as she said, "Perfect! You go to your room, get naked, lay on your back on the bed and I'll be right down!"

In my room, I stripped and I was already getting hard when she came into my room wearing her robe. When she dropped it, my 'getting' quickly went to 'fully', partly because of the harness she was wearing with the vibrator I'd been borrowing attached to it but also because that was all she had on. Over the years, we'd caught quite a few accidental looks at each other nude or partly nude but this was the first time either of us had intentionally seen the other nude and I noticed that as much as I was checking her out, she was doing the same with me. I knew she had big tits just from watching her around the house both with a bra and braless but naked, they looked even bigger and while her nipples weren't huge, her areolae were almost two inches across and very dark compared to her pale boobs. With the harness in place, I couldn't see much of her pussy but from what I could see, it looked like she was shaved bare. When I looked back up, she was grinning at me and said, "Well, it looks like you're my 'big' brother in more than age. I'm glad you're not gay because that's too nice a cock to waste on another guy but I'm more interested in seeing what using this on you feels like."

As she said 'this', she gave her hips enough movement to make the vibrator swing around. Then she grabbed the lube, got her finger nice and slick and spent a little time rubbing it around, over and eventually into my pucker. Having played with her vibrator in my ass, her finger slid in fairly easily and was soon 'upgraded' to two fingers. I was doing pretty good at not letting on just how much I was enjoying it but when she added a third finger, I couldn't stop from moaning and when I did, she said, "If three fingers make you moan, let's see what happens with this" and as she pulled her fingers out, she replaced them with the lubed head of the vibrator.

She'd already turned it on and then she slid it inside my ass except she did it a lot faster and harder than I normally did. Thankfully, I'd gotten used to it's size so it went in reasonably well but there was a little bit of pain as it stretched the internal muscle ring but almost immediately after my 'owwww!' there was a softer, 'Ahhhh' that let her know things were ok.

When I'd played with myself, I'd always been in control of the speed, depth and force but as she started sliding in and out of my ass, I quickly realized it was a very different feeling when not only didn't I know but I really had no control over it either. I was fully enjoying my first actual pegging from a woman and contrary to what I'd told her, the fact that the woman doing it was my sister just added to my arousal.

Looking down at me she said, "Damn, this is even better than I'd thought it would be. I love the feeling of being in control and actually doing the fucking and I can feel the vibrations right through the harness. It's not the same feeling as being fucked but it's got me really close to cumming! How'd you like to cum with your sister?"

That thought got a noticeable throb in my cock so with a big grin, she reached out to stroke my cock and at the same time started fucking me even harder and faster. At almost the same time that I exploded and covered my chest in streams of cum, she moaned and held the vibrator deep in my ass as her own orgasm rocked through her. When she finally quit cumming, she slowly pulled out of my ass and said, "That was amazing! From the looks of all that cum, you'll need a shower before bed."

Then with a grin, she added, "I'm not sure whether you enjoyed it as much as I did but the next time mom and dad are out, I'll be looking forward to a second round!" and with that, she got up and went upstairs, leaving me laying on my bed.

After grabbing a shower, I went to bed and had some awesome dreams of being pegged again. Unfortunately, mom and dad didn't go out for the whole evening that often so I wasn't sure when the next opportunity would be that it would be just Kirsty and I at home with enough time for the second time. Kirsty wasn't working, I only worked evenings, dad worked days and while mom sometimes helped out at a friends catering company, she was usually home so the problem was that either they were both home in the evening or mom was home all day. As it turned out, things fell into place for that Wednesday when mom got a call from a friend of hers who ran the catering business. Apparently one of the women had called in sick and they were really busy so she asked mom to come in and help out with some of the food prep. I didn't know about it until Kirsty stuck her head in my bedroom and woke me up with, "Hey, mom's gone for the morning so how about I get my second round?"

Having just woken up, I wasn't processing things too well yet but when I rolled over and looked, Kirsty was standing in the doorway, naked except for the harness and vibrator. That got my brain going a little bit faster and as I was processing what I was seeing, I realized that the vibrator wasn't the same one that I'd found in her drawer, instead, it was definitely longer and thicker. She must have noticed me looking and with a grin said, "You didn't think I kept all my toys in one place, did you?"

I really didn't have an answer for that one but looking at the size of what was strapped to her waist, I suddenly realized that the nerves I was feeling must be the same as when a woman wonders if she can take a bigger cock in her pussy. Almost as if she was reading my mind, Kirsty said, "It might take a bit of work, it'll fit. I remember how it felt the first time I worked it into my pussy."

I couldn't help but think that a pussy was designed to stretch and accommodate larger things where my ass really wasn't but at the same time I was a bit excited to try it. Laying on my back the same as last time, she took a bit of extra time making sure my ass was nice and slick before edging the head of the vibrator at my opening. She gave me a running commentary of how much was inside me and the head wasn't even half way in when I felt way more stretched than I ever had been and just as I was wondering if the head would even go in, there was a sharp pain, a pop and I heard her say excitedly, "It's in, the head just went in."

I groaned with the pain and asked her to stop for a few seconds. As the pain died down, I started shifting slightly up and down with my hips so that I could feel it pull out slightly then back in. When I got used to that, I told her to keep going but gently. At least she listened to that and about another 2" slid in before coming to a complete stop. I knew from playing that there was a second muscle ring there but the other vibrator has just slid in with minimal resistance. each time she pushed, I could feel the ring accepting a bit more of the toy and each time it did, there was a slight pain followed by a pleasurable pressure. Then suddenly on one thrust, the head popped all the way in and damn did it hurt for a few seconds. I yelled for her to stop but instead, she panicked a bit and pulled all the way out which triggered a slightly different pain followed by an empty feeling.

"Was that too hard?"

"Not sure, it just popped in and when it did, it really hurt. Give me a sec, ok?"

"No problem, maybe it'd be easier from behind like it showed in some of the videos."

It didn't take long for the pain to go away and when it had, I rolled over so my ass was high and facing her then said, "Ok, go slow but give it a try this way."

Maybe it was from the first thrust that had gone all the way in and maybe it was the position but it went in a lot easier and with only a slight bit of pain. Once I got used to it, it started feeling better when Kirsty started thrusting in and out. It still felt huge and I could feel it stretching me every time it slid in but now it was more of a pleasurable stretching that felt better and better with each thrust. The other thing I found is that between her angle and mine, this way the vibrator was hitting my prostate with each thrust and when it did, the vibrations went right to the end of my cock like an electric tingle and then she'd pull all the way back so when she slid in again, it would have to push past the muscle that was still trying to close.

I managed to gasp out, "That feels....really...good! Gonna cum soon!"

From her breathing, I thought she was getting close but I couldn't hold back and shot rope after rope of cum all over the bed under me. I kind of fell forward which pulled her out of me. I looked around just in time to see Kirsty pulling the vibrator to the side and frantically rubbing her clit. In less than 10 seconds she was moaning and cumming as well before falling beside me on the bed.

"Holy shit that was intense, was the bigger one ok?"

"It was definitely intense and that was the biggest thing I've ever had in my ass but once it went in, it felt good and even better each time the head pushed in and I could feel a slight stretching again. I think I'll be sore tomorrow so I might need a day or two before we go for the third time."

As it was, we didn't get a chance to do anything for over a week with nothing ahead looking good either. Then at supper, mom said to Kirstie, "Your aunt Matty called today. She's going away for a few days and she asked if you'd go over and check on the cat at least once a day for her and give it a bit of attention. She didn't say anything but I'll bet she'll pay you something when she gets back."

Just the way she said it, I could tell that she'd already told her sister that Kirsty would do and Kirsty must have realized it to because she just nodded and said, "Sure, when does she leave?"

"Thank you! She leaves tomorrow."

The next morning as we had breakfast, Kirstie said, "Mom, you know I don't really like the area that Matty lives in. If I have to go, can Kirk come with me so I feel safer?"