“My Boyfriend’s Brother”


“.....My boyfriend’s older brother came home for Thanksgiving. We didn’t get to see much of him over the course of the seven years we have been together. But, whenever he came home, it was always an event. He was the favorite of his parents. I think it was because he was the only one that went to college. Even though he got a full ride for playing baseball. His career didn’t last very long, though. After college he blew out his arm, and his pitching days were over. His name is James. He has never been married, or he never seems to have a steady girlfriend. Long enough to call it a relationship, for that matter. I couldn’t figure out why. Maybe he just liked being single. He was sort of a ladies’ man. He just had an aura about him. He’s definitely a cute guy. When my boyfriend and I first started dating it was around the holidays. James liked to drink. He was the stereotypical “frat boy”. I think he wasn’t sure how serious his brother and I were at the time because the nights he was drinking he’d always text me. I don’t even know if he remembers any of that. He was certainly hitting on me. He even texted me off and on for a few weeks that year on what he would do to me. I remember it really turned me on. But, that was a while ago. He’s probably been with so many women since then, anyway. 


Thanksgiving night, he seemed to be looking at me like I haven’t been looked at in ages. I caught him across the table staring at me. It kinda made me blush. On Thanksgiving Night, my boyfriend would meet up with his buddies, that were home from college, at our local tavern, to catch up on life. I normally would go with him, but I had to get up early for work. So, I was just going to be spending my night alone, in our apartment. 


About an hour after my boyfriend left, I was curled up on the couch watching Netflix in a pair of sweats and a t-shirt, just relaxing from eating all of that Thanksgiving food, when someone was knocking on the door. Not having any idea who it could be, I looked thru the peephole, and it was James. Surprised, and a bit curious, I let him in. 


He knew James wasn’t home, and that’s the reason he stopped, he said. He said he had a  gift that he got his brother, that he forgot to give him earlier. He told me he just wanted to drop it off, so it was here for him to open in the morning. I told him to stick around a few moments, that he didn’t have to leave so quick. I mean, he was staying at his parents, and they live outside the city, about twenty minutes away. I would of felt bad if I didn’t ask him to come in for a little while. 


We made our way into the living room, where we both sat down on the couch. We were both looking for something to say, so he brought up the girl that was in the movie I was watching. He said she kinda looked like the girl he was seeing out East. I was taken back. I didn’t know, like I said, that he was even seeing anyone. He started talking about her like he was in a room with his college buddies. He was talking about their sex life, what she was into and personal stuff like that. I don’t know if he was saying all this thinking I was just one of the guys, or he was purposely saying it to turn me on. Well, whatever the reason, it was working. My panties were getting wet. 


Then, James started to laugh. I smiled and asked him what was so funny? He started to ask me if I remember texting back and forth that first year his brother and I were together. I acted like I was digging for the memory, yet, in fact I nearly memorized his every line. I was really starting to feel horny, talking about this stuff. I told him that I do remember the pic he sent me of his erect cock, and how he said he wanted to put it in me... This statement was a well thought out plan, on my part. For whatever reason, I said it, and it just snowballed from there. 


The fact was, I do remember the photo, and I have thought about that wide cock fucking me on more than one occasion. Now, I wanted to see that fat cock up close, and in my hands. It was a surreal moment. I knew it was so wrong, but, lust was getting the better of me. 


I got up. I told James I had to go to the bathroom. In reality, I had to collect myself. I loved my boyfriend, his BROTHER, I couldn’t be doing this? My mind was going in circles. I was also thinking about what I could do, that wouldn’t be cheating. I thought, well, they are brothers, so that wouldn’t be cheating. Where was my head. What was I thinking? I can’t do this? 


 Then it happened. James came in the bathroom, got behind me, put his hands gently on my shoulders and started kissing my neck and nibbling on my ear lobe. He asked if this was ok. He felt so warm and comforting, I said yes. I haven’t felt that feeling of total want in a long time..


While he was kissing me, I reached around and fumbled for his cock, which I found rather easily, because he was solid fucking hard! He lifted off my shirt, and I had to tell him, “I don’t want to cheat on your brother..” He continued to take my shirt off and told me not to worry about it, he said you really won’t be cheating. He said, “cheating would consist of us kissing, you giving me a blowjob, or me fucking your pussy. And since, I don’t want any of those three, it’s definitely not cheating.” I don’t know what we were even doing then. But, somehow I bought that. I believed those were all the boundaries that make up cheating. 


I started to really rub his monster of a cock through his jeans. That thing was just pulsating to get out of there. I wanted it so bad in my pussy, but I had to stick to my convictions. Haha. Gees. I really can’t believe I fell for all of that, but I did. He put his hands around my waist and started to wiggle down my sweatpants. Just as he got them past my ass, he stopped and he put his hand down the front to feel my warm wet pussy thru my panties. He started rubbing me. I buckled over. His hand was electricity on my pussy. I moaned with desire. I wanted this.


With his free hand I heard him unzip his pants, and shuffle for his cock. He then put his hand down the front of my underwear. I gasped with pleasure as his calloused hand worked its way down past my short, soft pubic hair, and spread my pussy lips with his one finger, unleashing the wetness that was hiding on the inside. I closed my eyes, for what was coming. 


James inserted his finger in me, as I slowly continued to slime his cock up with his own natural lubricant. His wide finger massaged my inner pussy by sliding in and out. With my hand twirling around the head of his cock, I sat down on the toilet, with my sweats still around my thighs. He started to go down on me. I was breathing heavier with anticipation.  He grabbed the sides of my panties, and shifted them down to nest on top of my sweatpants. I lifted my legs, and he pulled them off, and my panties, until I was fully exposed. My bare ass and pussy felt the cool air from the wetness of my previously worn panties. 


He continued down to my wet shaven pubic hair. I was already moaning. He put two of his fingers into his mouth to get them wet, and then and separated the lips of my pussy again, finding my sensitive clit. He was already doing more than his brother ever did. My boyfriend rarely went down on me. Holy shit the feeling of electricity shot thru my body when his warm tongue hit my clit. Separating my pussy, he began to flutter his tongue, hitting my clit just right. Going faster, and faster, and even faster. I looked down with amazement on what he was doing to me. He could of done anything to me at this point. He had me. I was reaching an orgasm. I told him not to stop! It felt like nothing I have ever felt before in my life. 


I was gripping his head like a vice in my knees. Shit it felt so good. His face and neck was soaking wet, but he didn’t seem to care. He asked if I wanted to try something “different”, and if I was game. I couldn’t really think of anything. I was hoping he was just going to start fucking me, because at this point, I would of went along. But, right there, on the toilet, he put my legs together and held them up into the air. I had to shift my body to get a little more comfortable on that lid. James helped me out, by moving me out to the edge of the covered seat. He put my one leg up on the sink, and my other I held with my hand. 


I thought, yes, he’s just going to do it. He’s going to stick his cock in me...Instead, with me in this position, he went down and started licking around the area of my asshole. He was just one pleasure after another. I never had this before. I thought he must really want me, to be doing this. As soon as he entered my virgin hole with his tongue, I didn’t want him to stop, EVER. What an incredible sensation. Dipping his tongue in and out of my ass was amazing. I could feel his whole mouth all the way around my anal canal. It was so raw. So tribal. So animalistic. It just turned me on thinking about how naughty and dirty it was. I hadn’t showered since the morning, so I know my asshole was sticky, but that didn’t seem to concern James. He had his whole tongue circling around in there, sucking on my ass, cleaning up all of my pussy and ass juices that made its way down into my hole. 


He then stuck a finger in my ass and fluttered his tongue in between the area of my pussy and my asshole. Shit. It felt like I had an ass clit. He spun his finger around as he put it in and out of my ass. His knuckle seemed to pop out, every time he retracted it. Soon he had two, then three fingers in my ass, spinning them around. Opening me up. The wider he got with his fingers, the wider I wanted him to go. I wanted him to try and fist me. I tried when he took a breather for a second. I wanted to continue to feel like I was filled up. I easily got four fingers in, but I would have to work on my fist. The angle was hard. 


He took my fingers out, and sucked on them. He said he loved the warm taste of my ass. Every time he slipped his fingers or tongue OUT, it shot thru my body. It felt like having an orgasm, every time my sphincter closed when he exited. He had a mouthful of spit as he went down and poured his hot saliva all over my little virgin asshole. He took his glossy hard cock and pressed it up against my anus. There it was. I wanted this so bad. I felt like I was having an out-of-body experience, wanting my tender asshole to be penetrated so bad. My sphincter ring was so loose. The head of his cock made it past that ring with ease. 


Looking down at myself, I came. It was an intense orgasm. All it took was me looking at my empty pussy, and looking beneath it, to this huge staff sliding into my forbidden hole. “Fuck my ass, James,..Oh, show me what your brother would never do, mmmm..”, I, barely coherent, got out, while his massive member went into me further. My God, the sheer pleasure. 


I couldn’t believe it. I couldn’t believe I was letting someone enter my ass without it being my boyfriend. But, I wasn’t letting James leave  without impaling me with that cock. I wouldn’t let him... Holy shit the pressure. It hurt.I tell you, it hurt so bad, I wanted more! I grabbed that monster and began pushing it in my ass, like I was putting a dildo in there, by grabbing it by the shaft, and pulling it closer to me. 


I know I was gritting my teeth, but I swear it was so intense it felt so fucking good. Fingers were one thing, this was entirely different. The whole naughtiness of it. The dirtiness of getting assfucked. That mindset is what got that big bastard in me. He was half way in. Sliding. I started to rub my clit. It was still sensitive, so I had to rub easily. Reaching down with my other hand and feeling his cock in between my spread out fingers, touching my stretched out rim, and the gooey mess surrounding it. I fucking mentally wished that thing all the way in even if it was splitting me in two. 


Finally I felt his pubic hair brush up against the bottom of my ass. He took my ankles in his hands and began to back out. Holy shit. This was a whole other list of pleasures. It felt like he was pulling my insides out with him, but that process felt so fucking unbelievable. Back in. Then out. I could feel my sphincter muscles giving out. He started to pick up speed after a dozen or so pumps. When he did this his balls started slapping up against my ass, making a wet slapping noise. I wish he was videoing this. I could easily masturbate watching my ass getting destroyed. All I could muster to say was a string of “Fuck my Ass!...Fuck my tiny asshole!” This was affecting him. He started saying, “How does your boyfriend’s brother feel up your young ass?! Yah, yah, every time I’m home, I’m fucking this ass!”  He was moaning and really pumping in and out. I was going just as fast on my swollen clit. 


Out of no where I felt my intestines fill with his hot milky cum. Holy shit. Doing this, I came immediately. That’s a whole new feeling. He kept spurting more and more in my dark hole, as far as he could go. James had his butt clenched and his back arched, giving me his whole length, deep inside me. I could feel some of his sperm dripping down the sides of my asshole. He pulled out and then shoved it back in to squeeze the last drops out. Exiting my ass, which it’s meant for, his cock plopped out. 


My asshole was pulsating with pleasure. It didn’t know if it was supposed to stay open, or if it were supposed to close. It was gapped. It was making noises from all the air that got pushed in there. I felt my hole with my fingers. Easily being able to put them all in and scoop out James’s warm, fresh cum. In the heat of the moment I licked all of that batter off my fingers, only to go back in for more. Breathing heavy, I gobbled up all of that clear, milky cum I could get from my open ass. 


James was about to kiss me when he remembered his oath. He said, “See,...I wasn’t lying. I didn’t kiss you, you didn’t blow me,...and I didn’t fuck your pussy...” I laughed, and felt bad, because I knew all along,.. I was cheating... But, it was just our secret, and no one needed to know, and wouldn’t. I made sure it wasn’t going to be me, because James even said, it didn’t matter to him, even if he got married, he was going to fuck my ass every time he came home. I loved that thought, and honestly, I could not wait until Christmas...”



Writer’s note: I’m not a writer. I just enjoy turning people on. Stories are so much better than watching porn. I personally think they can give you a more intense orgasm. The mind is the most powerful thing. 

This is my first story I posted on here. I have a ton more. If you would like to read more, just let me know. If you’re a girl, and would like to know more, or if you want to send me a pic, or an idea, you can always email me. I’d love to hear from you!