2000 and Jen
Introduction:
Something different. A TRUE story about me fucking my best friend’s girl.
I want to start this story just by saying that this entire story is 100% true. In fact, there is actually more to it but I was fairly drunk when the main part of the story happened so there are probably even more juicy details that I have left out. But what is true is that this night was the most exciting of my life. It was a night that was the stuff of fantasies. In fact, it fulfilled a fantasy of mine that I had held for a while. And before you judge me or the girl involved with this, try to read through what happened and feel the passion behind this one great night. I’ve changed the names of most of the characters in here on the off chance that someone I know could read this as it would fuck up my life and the girl involved. Hopefully everyone enjoys this story, as it was one of the most amazing nights of my life, one which I will never forget, and one that may be a once in a lifetime event…so enjoy…and sorry if it starts a little slow, but every detail needs to be in here so that you can see where I’m coming from. If you just want the dirty sexy details, just skip to chapter two!
Chapter One: The Background
The most amazing and sexy night of my life happened on New Years 2010. A ridiculous amount of things had to happen to actually let what happened happen (and what happened was I had wild passionate sex with a beautiful girl who happened to be the girlfriend of one of my best friends). To jump into the story there is some background info you need to know in order to understand why things happen the way things happened.
For starters, my name is Steve, I’m 22 years old, and I live in a Midwestern town with three roommates (Bryan, who lives upstairs with me; Tim, a guy who lives downstairs and wasn’t there during the night in question; and Jay, who also lives downstairs). Bryan, Jay, and I have been best friends since way back, and that extended through our college years as we all stayed in town. Jay has a girlfriend named Jen, who is a beautiful little petite blonde with perky tits (34B-34C or so), a wonderful tight ass, and perfect tan legs. I always kind of thought of her as a rich little spoiled bitch (which she is) but lately I had begun to think more of her. And needless to say, with a body like she had and the platinum blonde hair and pretty face, I was always attracted to her. I guess in a way she is sort of the opposite of my usual type, which is something that helped turn me on even more for her.
My usual type, I suppose, would be exactly what my girlfriend now (and at that time) is. My girlfriend Beth is also a beautiful girl but in different ways. She’s got bigger boobs (34D), more voluptuous hips and ass and thicker thighs. She sort of has golden brown hair with blonde highlights. We have been together about 4 years at this point. She’s really down to earth and a great girl overall, and she comes from a middle class family unlike Jen. I’ve always gone for girls like Beth, who are down to earth, funny, cool, and can take a joke. Jen, on the other hand, I had always seen as a girl who was completely out of touch with real life because she had that annoying rich upbringing. And she always gives off this “I’m a stupid blonde” persona and talks in a really high voice and makes stupid comments. Also, she was always the type to go wayyy overboard in trying to get people to like her. You know the type…calls everyone “love” right away, refers to girls as “beautiful” when you know she knows that she is way prettier than them, flirts with all the guys, fishes for compliments by saying how fat she is and how ugly she is and all that bullshit.
Now, I’ve always been the type of person that can spot a fake a mile away, and I fucking can’t stand people like that. When Jen first came around, most of our friends fell in love with her right away hook, line, and sinker. Fuck that. I have lots of friends and if you want to be my friend, cool, but I’m not going for that bullshit. There’s more to me than that. And that was always my attitude with her and for the longest time I think she sort of got that and she laid off of the fake bullshit to me.
Don’t get the wrong idea about how I felt about this girl. It may sound like I hated her but I really didn’t. She had lots of annoying little things that got to me but in reality I always thought she was a good person. Some of the fakeness came from a good place I think, because I really think she just wants people to like her. Also, over the year that her and Jay were together I had actually ended up having several deep one on one talks with her and found that she was actually a smart person and could be very funny and fun to hang out with. And it was one of these talks that started this whole fucking thing in motion.
So I fucked one of my best friend’s girlfriends. I’m a horrible person right? Before you decide to hate me and give up on this story, at least listen to how all this started. Back in April of 2009, my girlfriend Beth and I decided to take a break for a while. A week into the break, Jen, Jay, Bryan, a friend of Jen’s, and myself were hanging out and drinking at our house. Jen and Jay got in one of their many ridiculous drunken fights and Jay went in to bed. Jen and I ended up outside on the street talking to each other. She was seriously considering breaking up with Jay for several reasons; one is because she is very sexually experienced and kinda freaky and he is boring. Another is because she was his first….for some reason he decided against fucking any girls through high school and most of college. I really don’t understand this because I love fucking and have had lots of pussy but I guess if that’s your thing then whatever. So me and Jen are sitting on the street talking and we were sitting really close to each other…it was pretty cold and we were kind of huddled up. Now, I am NOT the type of guy to ever put a move on one of my buddy’s girls. I know the rules against that kind of shit, I’ve never done anything like that before, and I honestly keep those kind of thoughts outside of my mind. But that night, sitting there talking, out of nowhere Jen leaned forward, grabbed my shirt and tried to kiss me. For a moment I started to go with it, then pulled back and told her, “Look, I can’t do this to Jay man. I think you’re an attractive girl and all but I just can’t do that to him.” She agreed we shouldn’t do it. My heart was pounding though all the sudden and my thoughts were swirling. But we kept on talking. Moments later, she moved in for a kiss again. This time, our lips got even closer. I pulled back again, saying we shouldn’t be doing this shit. She said how she loved Beth and Jay and couldn’t do that to them. This pissed me off. “Fuck Beth, Jen…I’m not with her anymore,” I said, “…I’m single now, I can kiss whoever the fuck I want, what about your boyfriend.” At this point she put her hand on my leg and began running it down my shorts. “I don’t give a fuck about Jay right now, he’s always being such a tight asshole,” she said, her hand now down into my boxers. Right as she wrapped her hand around my now hard cock, I pushed her away. “Look Jen, I’d love to do this, I think you’re incredibly hot to be honest with you…but I just can’t do this to him, he’s my best friend…” And before anything else could happen, Jay was stumbling back outside.
Chapter Two: 2010-First Fuck of the Decade
Flash forward from April 2009 to New Years Eve 2009/2010. Another party is going on at our house. In the past few months tons of shit has happened. I had told a couple friends about Jen trying to kiss me but not many. Beth and I were back together, although part of the reason for that was because she told me she fucked some random (awful dirty hillbilly) guy and I freaked and wanted her back even though I never got my fill of random pussy. (I know, that’s on me, but still it sucked). The plan for new years eve was just to have a few people at our place, then hit the bars around midnight. Just for you score keepers out here, the people at the party included: Me, Jay, Jen, Beth, Bryan, our other best friends from high school Eddie and Paul (Paul was in town from the Marines for Christmas), Eddie’s girlfriend Denise and a few of her friends, and a few random bitches that Bryan had over. Bryan has always been the manwhore of the group. Me, Jay, and Eddie had gone to get a shitload of alcohol earlier in the day and by midnight were fucking hammered. The girls were all tipsy too but not quite on our level.
And this is where the fun shit starts. A ridiculous number of things had to go our way to allow Jen and I to hook up that night. Thing number one was that at around one AM, Jen caught Jay flirting with one of Bryan’s random whores. This girl was butt ugly but Jen still got pissed and in her drunken stupor went off on Jay. They got in a huge fight and were yelling at each other. Jen walked off and left Jay and the girl outside. Eddie and I were sitting there talking, and I brought up to him how Jen had tried to kiss me way back when. Eddie was one of the few friends I had told about it. I pretty much told him look I’m gonna fucking call her out…if she’s going to be bitching at Jay about flirting with this chick how about she answers for what she did with me? (keep in mind I had never said a word about it to her since that April night)
I went outside at this point and pulled Jen aside.
Me: “Hey, how the fuck are you going to be mad at Jay he didn’t do anything wrong.”
Jen: “He’s all over that fat whore fuck him, that’s bullshit.”
Me: “Oh okay, so it’s okay for you to try to kiss his best friend but he can’t even talk to another chick?”
Jen: “What are you talking about?”
Me: “You know exactly what I’m talking about Jen, when I was single last spring you tried to kiss me 4 fucking times right out here and you had your hands down your pants and everything.”
Jen: “Bullshit… you tried to kiss me.”
At this point she started to walk away but I grabbed her arm.
Me: “If that’s something you want Jen, I’m ready…the offer is on the table, just come get it.”
As she walked away I couldn’t believe how bold I was being. I mean I have no problem making a move on a chick, but not my best friend’s girl! And sure has hell not with my girlfriend in the same building! But my ways of thinking had changed a lot since the previous spring. What had gone on with me and Beth was one thing, but also I had started grad school and now had little or no time to party like I used to. Real life had started, and I had sort of adopted this thought process that life is short, you only live once, and if you don’t do what you want to do now it may never happen and all you can do at that point is regret all the moves you didn’t make and chances you didn’t take. I know this is supposed to be a sex story and not a philosophy lesson, but it is important that you know where I was coming from.
Moments later, Jay storms in and slams his door, ready to pass out after even more of a drunken fight with Jen. By this point, Beth had gone to sleep up in my room as well because she had work early the next morning. Everyone else was in the living room. Now normally, I would have been off having some drunk escapades with Bryan and Paul, as we were normally the dumbass crew of drunk guys that had fun and fucked around till 6 am whenever Paul was in town. But, here again, is one of those many things I talked about that had to happen in order for me and Jen to end up getting together. I mentioned earlier that we had planned to go out to bars, but we called several cabs and none of them ever showed up. Bryan and Paul (aka the two single guys) got sick of this shit and decided to drive drunk to a local bar. This left Beth and Jay in bed, a few random whores in the living room, along with Eddie who was painfully whipped on his new girlfriend and her friends in the living room as well. And of course me in the kitchen.
And as I stood in the kitchen, Jen comes storming in all pissed off as well. As she walked by me she looked me straight in the eye and said, “Maybe I should have taken you up on your offer, Steve.” This perked my interest for sure, but she stormed right by me and went and started knocking on Jay’s door really loudly. I stayed in the kitchen and continued drinking. She knocked and knocked and knocked for what seemed like forever. In another amazing stroke of luck, he never fucking let her in. Here’s our chance…
Jen comes back in the kitchen. I know I described Jen’s looks before, but tonight was a whole new ball game. This girl knows how to dress, she knows how to make herself up and how to look damn good. Tonight she was wearing a pink and white and black tight little cocktail dress (probably cost a couple hundred bucks) with a nice little push up bra under it that made her tits look big and delicious. Her hair looked amazing and her face was so pretty. She also had on some sexy little stockings.
She sat down in the kitchen next to me and asked me to pour her a drink, to which I obliged. We started to talk and finally I had the balls to ask her what she meant by take me up on my offer.
Jen: “What do you think I meant Steve? You know ever since April I’ve been ridiculously attracted to you. I don’t know what it is. I know you’re not my type. I know I’m happy with Jay. But it’s just something about you. I’ve wanted you ever since then.”
Me: “I know exactly how you feel, and you know what I don’t even care anymore…I want you, I know I want you, and I’m gonna get what the fuck I want.”
I finally moved in and kissed her. We immediately started passionately making out. She had her hands on the back of my head and was pulling me in closer as our tongues intertwined. I was immediately hard as a rock and knew right then I had to fuck this girl. She was an amazing kisser and everything just seemed to fit. We stood up and she pushed me against the door. We continued to kiss, being equally turned on by how hot our kiss was and how risky it was; what with her significant others in the house and several people right in the next room who we would hear talking and fucking around. I had my hands all over her body. I had grabbed her tight ass and had my hands all over her tits when she leaned up and whispered words in my ear I’ll never forget… “Come on Steve, I want more…”
Me: “Well let’s go, let’s go do it!” I said like an excited 13 year old about to get his first hand job.
Jen: “Where can we go though, there’s people all over the house and Jay and Beth are both here…I don’t know.”
Me: “Let’s go to the basement! No one is down there and we’ll easily hear anyone if they are going to come down and I can just hide and you can just pretend you were drinking down there.”
She immediately started walking towards the basement, but much to my chagrin she walked by the basement door and began pounding on Jay’s door again, trying to make him let her in. I actually let this go for a couple minutes because I didn’t wanna let her think I was too desperate to make this happen. But after a couple minutes she was getting really loud and I told her that she was waking people up in the house and that she should go in the basement with me where we could just play beer pong one on one or whatever. She agreed and we went downstairs.
Before we even got to the bottom she was kissing me again. We went into a corner and made out just as passionately as before. Our hands were all over each other, with her grabbing my rock hard cock and me with my hands all over her ass and tits. Finally I yanked her dress down and there they were, her perfectly shaped tits, perkier than any I think I’ve ever seen. They looked so goddamn delicious, and her nipples were already hard. I began rubbing them and feeling them, and then moved my face down and began licking and sucking on her nipples one at a time. I could feel them get even harder in my mouth, and she was pulling my head into her tits to get me to lick and suck on them even more. She was moaning in such a hot little soft voice. I couldn’t get enough of her boobs. Every girl I’ve been with has had big boobs in the voluptuous style like I told you I liked. Some of them were even kind of fat and unfortunately for me had kinda saggy tits. But this girl was like a fucking porn star. They were little and petite but not too little and just so amazingly perky. I sucked on her nipples and played with her tits for several minutes and ran my hand up under her dressed and began to play with her clit. She was already soaked, and I could feel from her pussy that she was shaved completely bald. We began kissing as I continued to finger her clit and her pussy when out of the blue she pushed me back onto a recliner that we had in the basement. She gave me a devilish look and reached down and grabbed my belt and unfastened it. She unbuckled and unzipped my pants and pulled them down to my knees and grabbed my cock. “Holy fuck you’re big, I want your cock so fucking bad,” she said. Now, don’t get me wrong…I’m not trying to write a story here to make it look like I’m some kind of sex hero with a huge cock. I’m really not that big…maybe a little bigger than average but it’s not like I’m carrying around a 13 inch dick or anything porn starfish. But that’s legitimately what she said. She began sucking my cock and gave me the best goddamn blow job I’ve ever had. She could swallow every last inch and she worked her hands so good on it it was amazing. She probably went on for ten minutes, just sucking it so firmly and using her hands, and always taking a pause here and there to look up at me and give me those bad girl eyes. She would also let out a little moan every now and then which was so fucking sexy. She finally took a little break and I felt like it was her turn. I had her put her leg up on our weight bench which was next to the recliner I was in. Her tits were still hanging out of her dress and my hard cock was still laying there in front of me but she did as told. I pulled her dress up to reveal her legs which were still covered in the stockings, then her bare leg, and finally at the top her perfect little pussy which was covered by a see through black thong. I pulled the thong down and took in a beautiful sight. Her pussy wasn’t shaved, it was fucking waxed. There was no hair whatsoever, but no razor burn so it looked completely bald and sexy. Also, she had a really small pussy, not like abnormally, but her clit was little and her little pussy lips just stuck out a little bit. I could actually SEE that it was already soaked. But as the guys reading this will understand, she had a beautiful pussy. You could actually SEE that it was tight somehow. I leaned forward and put my head between her legs and began licking her clit. I’ve always been good at oral, and I gave her every last ounce of talent that I had. I ate her pussy for probably ten minutes. I had my hands on her bare ass, which was amazingly fucking tight from all the working out she does. I was using her ass to pull her pussy closer to my mouth. By this point I was alternating between licking her clit and burying my tongue deep in her pussy. It tasted so amazingly good. I don’t know what it was, but her pussy just tasted beautiful. She had her hands on my head and was pulling me tighter into her pussy. She was moaning but not porn-star style. It was so fucking hot, she would sort of just start by breathing heavy, and then there would be the slightest little high pitched moan, and it would slowly build but never to the ridiculous porn star screaming and yelling that some chicks use. At some point, I’m not sure exactly how we decided this because I was hammered, but at some point we decided we needed to take this to a new level.
Jen took my hand and led me up the steps. Out of all the things I talked about that went our way that night, nothing was more important than this: Tim wasn’t home, he had gone somewhere else for New Years. So as we reach the top of the step, we found an empty bed room right next to the top of the basement steps. Jen led me into the bedroom, we locked the door, and she jumped up and wrapped her legs around my waist and we started making out. Now of all the hot fucking shit about what happened that night, maybe the hottest was that I was about to fuck Jen in a room that literally shared a wall with Jay’s bedroom, while Jay was sleeping in that bedroom. Sure I’m a horrible person, sure I’m a horrible friend, but that’s just human. It was a fucking huge turn on for me and Jen, and I think any of you judgmental pricks out there would have the same exact fucking feeling…
I carried Jen to the bed and laid her on the bed and within seconds her dress was gone and all she had left was the stockings and the thong. I yanked the stockings off as she removed the thong and I dropped my pants quickly. And there it was, that beautiful pussy for all my fucking pleasure. I pushed my cock down to her pussy and slowly pushed it in. MY FUCKING GOD it was so amazingly tight! Luckily it was so wet I didn’t have to go too slow so I started fucking her like crazy. She was breathing so hard and I just kept pumping my cock deep into her, filling her all the way up with my cock. I remember at some point she actually said, “Jesus Christ Steve your cock is sooo much bigger than Jay’s, I’m just going to want yours forever now!” This of course pumped my ego and turned me on more so I began fucking her harder and faster. She kept begging me to fuck her harder and I did. All the while I was playing and licking on her tits, kissing her, or spanking her tight little ass. She was moaning loudly by now, in that sexy little high voice of hers. Until forever I will wonder if the people in the living room could hear us, because I could hear every word they said and Jen and I sure as fuck weren’t staying quiet, between her moaning and the bed rocking and shit. Finally I told her to roll over so I could fuck her from behind, something which she was very excited to do. I now had her ass right in my face, with her perfect little pussy pushed up and begging for my dick. Now I have to take a moment to describe her ass. Because as perfect as the rest of her body is, I’ve never seen anything like her ass. It was shapely and round and womanly, but tighter than any ass I’ve seen. Again, I tend to go for the voluptuous girls who tend to have big asses that aren’t as tight so this was such a goddamn turn-on, she was different than anyone I’d ever been with. I took a moment just to look down at her. I could see her tiny little petite waist, and as I ran my eyes down her body her hips splayed out all nice and womanly, with her perfect round ass there ready and waiting. She was looking back at me and told me she needed my cock right now. I grabbed her ass cheeks with both hands, and pushed my cock into her pussy. We fucked for another 15-20 minutes, with her cumming a few times, although I never did. She was moaning and going crazy the whole time, and she just kept telling me how amazing I was in bed, and I told her the same thing. We had amazing sex that night, and then finally we heard Bryan and Paul get home. At this point Jen started to get worried that Jay would notice she was missing or that someone would figure out we were in there, so she wanted to stop. Of course I wanted to keep going (I had lots of plans of cumming deep inside of her or in her mouth or fuck, wherever she wanted haha). But that was it. I quietly put my clothes on and snuck out of Tim’s room. I started drinking again with Bryan and Paul, just like the good old times. Moments later I saw her come out and she started knocking on Jay’s door again. He never let her in so she finally ended up sleeping in Tom’s bed. As for me, I slept upstairs with Beth like everything was normal. It was tough to get to sleep with all those hot memories swirling through my head but finally I did. The next day, after everyone had left, I went down to Tim’s room. I found Jen’s stockings laying there, and I took them. I still have them hidden in my room as a souvenir of an amazing night that I will never forget. I’ll always remember the first girl that I fucked in the new decade, in the year 2010-or as I call it, the year two thousand Jen.
Epilogue
So for those interested, here is what has happened between us since then and now (end of February, 2010). We haven’t had sex again, unfortunately. We have made out a few times and fooled around a little bit, including on Jay’s birthday when we were both wasted. For the first couple weeks after new years, Jen and I talked and flirted every day. We would text all day long and talk on the phone for hours, just flirting and talking dirty to each other. The first thing we decided was that we would never tell ANYONE. This is especially important for me because I’d lose all my fucking friends if anyone found out. But we talked so fucking dirty the next couple weeks and we tried so hard to get alone time to fuck again. We decided that we need to fuck at least one more time completely sober so that we can really get the experience and maybe get it out of our system. We even talked about possibly being fuck buddies from here on out considering how amazing our sex was. She loves Jay and I love Beth, and we both kind of said we weren’t going to leave them. But the sex was so good we both felt it shouldn’t stop. The sexual tension between us for the following month was amazing. A couple times we would get alone for a few minutes and we’d immediately be in each other’s arms kissing and touching each other. A couple times we hugged or touched each other right in front of Jay and the fucking sparks flew and it felt amazing. I learned everything about Jen. I learned she’s extremely horny. I learned every place she wanted to fuck me, from in my parents house to in a hotel to in front of a full wall mirror and everywhere. She told me she masturbates at least a couple times a day, sometimes in the bathtub, sometimes in her bed with a vibrator, and that she thinks of me most of the times. She told me that every time she fucks Jay now she just pictures me the entire time and thinks about me, and that that makes her feel bad. Her biggest fantasy is fucking with another girl and then having me walk in and fucking them both in a full out threesome. If that ever happened, my life could just end there because that would be the be all end all for me. I got to know a lot about her besides sexual stuff to though. We talked so much and got so many little jokes together and we flirted so much and became really close friends through all this. I feel so connected to her it’s really weird. I don’t know if I’m just lusting after her, or if I’m actually falling in love with her, or what. I’ve been really fucking confused for two months, but all I know is that every time I start to push her from my mind, she always sneaks back in. But o well. The weird thing that I always think about is that after that crazy passionate night and the ensuing weeks, if we were just normal single people there is no doubt that we would be dating and be together right now. So it’s really weird, because I feel like we’re denying all these feelings and it is miserable, but at the same time we can’t feel sorry for ourselves because we are involved with other people so we made our own beds. Unfortunately, Jay started being a whipped little bitch late January/early February, which made Jen feel really bad for constantly talking dirty with me and wanting to fuck me. So she has started to try to back out of this whole thing, which is okay. I don’t wanna like force her into it or anything. But even when she texted me on Valentine’s day to talk things over and say that she thought we should stay on the straight and narrow no matter how bad she wanted it, she ended by saying that she still thinks of it and still wants it. And when she gets drunk she’ll still text me and say things about how she wants it so bad or whatever. So who knows what is going to happen. I hope you all enjoyed this story, because I sure as fuck did. And all I can promise you is that everything here is real, and that if you have a fantasy (and it’s legal and doesn’t hurt anyone) that you should seize the day and make it fucking happen, because you only live once baby.
My email is [email protected] . Any comments, questions, requests for additional details or pictures or whatever are welcome. I’d love to hear if anyone liked my story. It’s the first one like this I’ve ever written! So please let me know!!!
