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Anonymous

Age when it happend: 17
Where it happened: Best mates house.
Langauge: English
Sex: Male
Rating: 10
Category: Straight

Well, basically, I’ve known my best friend for a good two or three years now, but until a few months ago, I’d never really been over his place (strange I know, but we were always going to parties/etc together and never his place or mine, lol, never really needed to. Oh, and don’t forget that we were also in Grade 11/12 together, so I saw him every day at school).

Anyway, the first time I went over his place I met his sister who just happens to be 16, and just happens to be one of the hottest chicks I’ve ever met. I’m not kidding here, she has the figure of a model, beautiful C-cup breasts (not sure of the exact size), and the prettiest green eyes you have ever seen. I don’t know what it is, but the first thing I notice about any girl is the colour and shape of her eyes.

So while my mate was getting ready (showering/whatever, we were going to a huge open house party), his sister and eye were talking (his parents were out, lucky me?) about whatever came to mind. She really liked me I think, although she never hinted at it. However, eventually the topic of sex (not exactly like “Hey, sex is great!”, but you know, the topic that all hormone charged teenagers eventually reach when talking to each other) came up and we mentioned a few things. Oh, and did I remember to say that we were walking to this party since we had both been drinking for the past hour or so? Yeah, probably should have mentioned that. ;P

Anyway, turns out his sister had been drinking a bit too, and we ended up kissing pretty hard for a few minutes until we heard the shower stop running.

Skip ahead about six hours, my mate and I got back to his place at about 3:30 in the morning, absolutely hammered, as you would expect. Neither of us had been able to get any further than making out/grinding with any of the chicks we met, so we were both pretty pissed off, lol. I think he had quite a few more drinks then me though, so before he even got to his room he passed out on the floor. The thud must have woken his sister up because she came out and helped me drag him to bed.

After that was done, I went into the lounge room to sleep on the couch, but was followed by his sister. Oh, I should also mention (need to remember these things ;P) that she was wearing the nothing but a long shirt which she slept in, and her underwear. It was a little cold that night, so I could see her nipples poking through her white shirt. When I saw her, a combination of alcohol, the memories of the night, sexual frustration at having been let down a few times, how incredibly sexy she looked, and the fact that I was still a virgin (obviously) had me turn rock hard pretty much in an instant. She sat down next to me and, believe it or not, practically pushed me down and slid herself on top of me, kissing me as we went down. Plenty of tongue and some good manoeuvring later, I had managed to remove my shirt shortly after getting on top of her.

We made out for a good 10 to 15 minutes before I tried my luck and slowly moved my hand from the bottom of her shirt upwards, sliding along her stomach to get to her breasts. Until now, I wasn’t 100% certain if she was wearing a bra or not, but you can imagine how much harder I got when I didn’t feel one blocking my path. I rubbed and pinched her breasts/nipples for a while before I tried my luck again and began to slide my hand down towards her underwear.

When I reached the top I moved my hands on the outside in order to get her even more excited, hoping that she’d let me go further. I rubbed around the top where I thought her clit would be (I’ll be honest and say that I’ve looked at countless websites showing the best way to use your fingers and the general location of everything. Also, the fact that I’d done this a few times before also helped ;P). After hearing a quiet moan escape her lips (we were still kissing at this point, so I felt it too), I was even more eager and slowly moved my hand down inside of her underwear.

If she wasn’t wet from all of the kissing and rubbing I had been doing to her breasts, then she was definitely wet now. Having fingered a few girls before, I knew where to do and attempted to rub her outer lips to build up some momentum before focussing on her clit. After a couple of minutes of this, I managed to get a finger into her before realising that her hymen was still in tact (again, I had read a lot about this ;P), so I just took it out and rubbed her lips as best I could while thumbing her clit. Needless to say, it worked, and after only a few more minutes she came pretty damn hard (well, I’ve only seen a couple of orgasms up close, but this one seemed harder then the few I’d given girls before :P) while moaning loud enough that had her brother not been totally wasted, he would have woken up and probably wanted to kill me.

After she had came down from her orgasm, she got up and had me sit down on the couch. She got down onto her knees and with the most devilish grin I’ve ever seen, she unzipped my pants and pulled out my cock. Now, unlike most people, I’m not going to be an idiot and claim that I’m extremely well endowed with an 11-incher, instead, I’m going to be honest and say that I’m only about 6-inches long, at most, but it has never really bothered me.

ANYWAY! Still with this grin on her face, she looked up into my eyes (remember that she has the most perfect green eyes in the world), opened her mouth, and slid about half of me into her mouth. WOW. I cannot describe in words how good this felt, but virgin or not, I nearly blew my load instantly. The only thing that stopped me was that I didn’t think she’d continue if I blew in her mouth, and this felt too damn good for me to screw it up. However, it only took about a minute of bobbing up and down (did I mention that this was my first blowjob? Yeah, lucky me! All I’d ever had before were a few wristies at parties, none of my girlfriends had ever let me go further then rubbing their tits from the outside of a bra) before I was about to blow. I quickly told her this and she took her head off and in a quick moment of panic, she turned around and grabbed a few tissues from the box on the coffee table. Just in time, at this point I had started cumming and the first stream went onto her face (I apologised what felt like a thousand times for that) before she managed to get the tissues into place and caught the rest.

I think it might actually have been her first BJ too, because after having a few more given to me in the following months by other girls, I realised just how sloppy her technique was, not that I cared at the time.

After wiping the cum from her face and telling me it was ok (about a thousand times :P), she got up, grabbed my hand, and started leading me to her bedroom. Now, put yourself in my situation. Your best friends sister, who is incredibly hot, has just given you your first blowjob after you managed to finger her to orgasm. She’s now leading you to her bedroom, after you thought that the two of you were done for the night! Needless to say, I was so excited that I was getting hard again within five minutes of cumming.

When we got into her room, she closed the door, turned around, and with the same devilish grin pushed me onto the bed as she had done before. While kissing again, both of us had managed to remove all of our clothes. When we were stripped she slid down my body, until her mouth got to my cock again. I was getting harder all the time, but I was still semi-soft from before, so it still took a few licks and sucks to get me rock hard again. I mentioned to her that I had condoms in my wallet which was in my pants, so she got off the bed (double-bed by the way) and grabbed one. After she had torn it open, she rolled it down my cock and got on top of me.

Again, I couldn’t believe it. Not only had I just gotten my first blowjob from my best friends sister, I was also about to take her virginity and lose mine at the same time, while her brother slept in the next room! With her still on top (I didn’t try to get on top of her first, I had read that it’s the best position for a girl to lose her cherry in anyway), she positioned my cock at her entrance and slowly lowered herself down. What must have only been few minutes felt like a few millennia as she lowered herself onto my cock while gently pushing at her hymen, then raising herself up again. When she finally broke it, the pleasure that I had been feeling multiplied sevenfold as the hot, velvety feeling of her pussy clenched tightly around my cock washed over me and she began to bounce (for lack of a better word) up and down on me at a slow, steady pace. It wasn’t long before I flooded the tip of the condom in the most satisfying orgasm I’ve ever had.

She just sat on top of me for a few more minutes, rocking back and forth as my orgasm subsided and my cock once again got softer. When she finally climbed off of me I just lay there in disbelief of what had happened while she took the condom off of me and disposed of it. Curiously, she licked my cock a little before deciding that she didn’t really like the taste, and then headed to the bathroom to shower.

I don’t want to make this story any longer then it already is, but I’m being honest when I tell you that I grabbed another condom and followed her, hoping to be lucky enough to let me fuck her again in the shower. Amazingly, she let me, and I ended up eating her out in the shower (first time for that too, lol!) after I flooded the second condom.

It’s been about two months since I first fucked her, and we’ve done it at every chance we’ve gotten since, although this hasn’t been many since her parents are rarely out at the same time as her brother is passed out/asleep. I don’t really want to risk losing my friendship with him too, so we’ve been very careful to make sure that he doesn’t find out that his best friend fucked his sister, and took her cherry at that!

Thanks for reading the story of three of my firsts. 😛 Many of you won’t believe me, and I wouldn’t blame you, due to the countless “fake” stories written on here and other websites. However, I promise you that this story is 100% true, and the fact that it’s so well detailed is simply because I’m a passionate writer, and remember every moment of that night (or at least, the parts after the party anyway) like it happened yesterday (or this morning, I suppose? :P) so felt it only right that I write about it to the best of my abilities. 🙂

NOTE: No names were mentioned for obvious reasons.

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