7 comments/ 63063 views/ 66 favorites Annabeth Tutors My Roommate By: remnick13 This is a cheating girlfriend / cuckold story. If that offends you, I really don't care. Annabeth is inspired by current WWE Diva, AJ Lee. All characters are over 18. *** Annabeth, the girl of my dreams, and I have been together for over a year now. She's a petite brunette, cute as a button, with a great ass, and dorky in that girl next door manner. Before I met her at a comic book convention, I socialized mainly with my roommate, Duane. I've matured, but he is as nerdy and socially awkward as I was back in high school. He is also overweight. I wouldn't go so far as to call him obese, but he is definitely portly. He has bad skin and even though I would never tell him this, I like how he makes me look like an adonis by comparison. The past few months have been real rough for him. Before, we were both members of the lonely heart's club. Now, that I have Annabeth, he is all alone. Sure, we go out on weekends as a group, but he cannot help but mope and feel like the third wheel despite our best efforts to include him. Annabeth has tried to find him a girlfriend more than once, but he always blows it. I used to be shy before I met Annabeth and she helped me come out of my shell, but poor Duane is borderline terrified of the opposite sex. The only woman he can function around is Annabeth. He's probably developed a crush on her in the past year. Not just because of her beauty and charming personality, but because she is the only female he has spent extended time with who wasn't his own mother. Duane was always in bed by 10PM, so Annabeth and I had the living room to ourselves at night. She had her own apartment, where she still paid rent, but had practically moved into our place. My name is Anthony, but my sweet Annabeth calls me Tony, even when I'm trying to watch "Ghost Mine" on SyFy. "Tony?" she asked while snuggled up against me on the couch. "Yeah?" I asked, still paying attention to the TV. "He's getting worse." You could hear the concern in her voice. "I'm worried about him." "Who? Duane?" I was still focused on the show, which irked her. "Yes, who else would I be talking about?" She took the remote and muted the volume. "He's just so lonely." "Are you thinking of fixing him up again?" I sighed. "Because that hasn't worked out too well." She shook her head. "No, it would be a waste of time. He can't be around women." "I know," I said. "Accept for you." "He's his own worst enemy," she lamented. "Well, what do you want me to do?" I asked. "Talk to him," she pleaded, yet I wasn't sure where she was going with this. I shrugged. "And?" "See if he would be interested in spending some time together," she said. "Just me and him." "What?" I was confused. "Why am I suddenly being ditched?" "He's never had any one on one time with a woman," she explained. "He needs practice." "Yeah, I guess I could ask him." I did little to hide my skepticism. "Is this weird for you?" she asked. "I mean, he's a close friend and I only want to help." "I know you have a good heart. I'll see if he's up for it," was my lukewarm response. "If he says no, then I'll drop it. I don't want to pressure him." She then turned the volume back on. "Sure." We went back to watching the show and I tried not to snicker at the notion, but I would do as she asked. Obviously, I was going to wait until she wasn't around to broach this topic with Duane. Who knows how a withdrawn individual such as himself would react to this unconventional proposal? After the show, we retired to my bedroom and she did a striptease for me set to Katy Perry's "California Gurls." She sucked on a lollipop as part of her routine. We knew that Duane slept with earplugs, so we could make as much noise as we liked. Once she was completely naked, she turned around and I took her from behind, kissing her neck and caressing her perky tits. "Mmm...such strong hands you have..." she cooed. "I'm so hot for you...big boy..." She grinded her ass into the tent I was pitching in my jeans. A standing lapdance of sorts. "Baby, you have such a tight little body," I whispered in her ear. "I wanna be inside you so bad." I fondled her entire body over the next several minutes, then I tugged my jeans and boxers down with her assistance. I lined my seven inch cock up with her wet pussy and then slowly penetrated her. I fucked her good and hard from behind and she met my every thrust. I was sexual inexperienced before we began our relationship, but now we had great rhythm. She looked back at me over her shoulder, encouraging me. This eye contact let me know that it was true love. "Yes!! Yes!! You fuck me so good!!!" she cried out in ecstasy. "Harder!! Harder!! Fuck me harder!!!" Annabeth was being so loud that Duane may have heard her even over his earplugs and humming dehumidifier. I didn't care though, I relished being the apartment stud. I knew she was close to an orgasm because she fell forward and gripped the bedframe. We picked up the pace, the floor beneath was creaking big time, she came first while I yanked on her long hair, then I pulled her back up and cradled her as I shot my load. I pulled out and she turned, revealing a smile that told me she totally satisfied. I brushed her hair out of her face and kissed her passionately. My way saying "I love you," without actually speaking the words. *** The next morning, after Annabeth had already gone home to change before work, I spoke to Duane about her plan to educate him about romance during breakfast. He was as flabbergasted as I expected he would be, nearly choking on a spoonful of corn flakes. I waited a few minutes for him to calm down before I said anything else. "Is it really that big a deal? You guys have spent a ton of time together," I pointed out. "Yes, but not like this." He was panicked. "Does she think that there's something wrong with me?" "No, she just wants you to be smoother around the ladies," I explained. He was clearly offended by my choice of words. "Oh, I see." "Dude, it's nothing to get worked up about," I promised. "Is it not?" he asked. "I'm now her sociological goodwill experiment?" "Duane, knock it off." I was getting ticked. "She just wants you guys to go out for coffee." "Coffee?" he sighed. "What does that entail?" I chuckled. "Sitting and chatting at a cafe for a few hours." "Since when does it take hours to sip coffee?" he demanded to know. "I think you're missing the point. It's not about the hot beverage." It was like I was talking into an empty telephone. I may have underestimated just how inhibited he actually was. "It's about the interaction between the two people having the coffee." "And when will this momentous occasion be?" he asked. "Saturday," I said. "Her favorite cafe is only two bus stops away." He fidgeted in his seat for a few moments. "Can I bring my laptop?" I shook my head. "No, you have to pay attention to her and participate in the conversation." "Fine." He relented, then he started clearing the table. "If you insist." "Yeah, I must insist because she insists," I muttered as I exited the kitchen. On Saturday, Duane left to meet Annabeth at the cafe around 1PM. I watched from the window and made sure he actually boarded the bus. He didn't have his laptop with him, but I thought it wise to check his room and make sure he'd left all of his other electronic doohickeys behind. It wasn't until I was already in his room that I realized I was breaking the roommate trust and invading his privacy. As I turned to leave, I saw wadded up tissues in his wastepaper basket. I immediately remembered all those lonely nights of masturbating before Annabeth, my angel, came into my life. Also, poking out from beneath his pillow was a photograph that appeared very familiar. I may have been overstepping my bounds, but I walked over to his bed and picked up the photo, which was of Annabeth in a green polkadot two-piece bikini, taken on our Labor Day beach outing. I'm not sure how I should feel about this. Angry? Back in high school, my friend Jason had hot girlfriends who I jerked off to a bunch of times, but I never got to know any of those girls. I don't even remember their names. Contrarily, Annabeth treats Duane like a brother and he defiles her image like this? The nerve of him. About an hour later, I received a text from Annabeth which read, "Not making much progress. This might take some time." What did she mean by that? Were they going to hang out at the cafe longer or would the experiment continue past today? Duane returned home at 6PM. Six hours seemed a bit excessive. He seemed to be his usual awkward self. I said nothing about finding the photo of Annabeth. I had chilled. It's not like I caught him sniffing her panties or something lewd like that. I chatted with Annabeth online that night, disappointed that she wasn't dropping by for a roll in the hay. She said that she planned to continue tutoring Duane on how to spend time around woman without getting so flustered. Before we signed off, she actually chastised me for never helping him tidy up in the kitchen. Did he spend the afternoon complaining about me? What the hell? *** The following Friday night, it was a classic, dinner and a movie. Not for Annabeth and I mind you, but for she and Duane. She borrowed her roommate's car and came to pick him up at 7PM because she didn't want him taking the bus home after dark. She was always so considerate, thinking of the wellbeing of others. She was wearing tight jeans and a vampire t-shirt which I had bought for her at Hot Topic. She was ironically adorable. We all chatted in the kitchen before they left. I was hoping that Duane would give us five damn minutes alone, so we could at least makeout a little, but he hovered around us until it was time for them to go. All I got from Annabeth was a quick peck on the lips. I ordered in for dinner because Duane usually did all the cooking. Duane didn't return until after 1AM and he seemed to be walking on air, almost as if he was tipsy. I was channel surfing in the living room. "Hey," I said just to make sure he knew I was there. "Hey," he responded, almost singing. "How was the movie?" I asked. "Terrible." Despite what he said, he had a look of euphoria. "How was dinner?" I asked even though I really didn't care. He had this big, never before seen grin on his face. "Delicious." It didn't make much sense to me. "Are you drunk?" I queried. "We stopped off for a few beers on the way back," he admitted. "Cool," I said without much gusto. "I even danced with some lovely ladies at the bar," he bragged. "Wow, good for you," I said kindly. "Annabeth did her job well." He then went over to the refrigerator. "Yeah, she danced with me first and was real flirty in front of everyone, so I guess that made me look more appealing." He grabbed a bottle of vitamin water and held it to his forehead to cool down. "Really?" I was pissed. She was being too nice and he was taking advantage. "She is one smart cookie," he said dreamily. "You're lucky to have her." "So, she didn't want to come up and say goodnight to me?" I asked. "Well, she had to return her friend's car," he explained before entering his bedroom. "Right, that makes sense." As soon as his door was shut, I knew that he was probably wasting no time in getting out that bikini photo of her and whacking off. I decided right then and there that I would put an end to these inappropriate dating lessons, which had gone just about far enough in my own humble opinion. I barely got any sleep that night. I could only doze off for a couple minutes at a time and I had some bizarre nightmares. One was of Annabeth and Duane at the movies. His cock was out and he brazenly placed her delicate hand on it. She continued watching the movie while stroking his shaft. Luckily, I woke up just as she lowered her head to take his prick into her mouth. Another was of them at the bar. She was bent over a pool table, wearing a mini skirt. He pulled up the skirt, she wasn't wearing panties, he gave her spanking in front of all the other bar patrons and she was totally getting off on it. I was so disturbed by these images that I ignored my morning wood because I knew what I'd be thinking about unconsciously... Annabeth and Duane, fucking like rabbits. *** I dropped by Annabeth's apartment the next day, intent on putting my foot down. Her roommate, Karyn, let me in. I found my sweet angel alone in her bedroom, laying out different ensembles on her mattress. She did not acknowledge my presence. "Hello," I said while wrapping my arms around her. She did not return my affection, squirming away. "Yes?" "What's the matter?" I asked, feeling the tension in the room. "You tell me?" She turned and faced me. "Why are you telling people that I'm a rude, drunk, bitch?" "Excuse me?" I was dumbfounded. "I never said anything like that." "No? What about last night?" she asked with some conviction. I was at a total loss. "I don't know what you're talking about." "Duane told me everything," she clarified. "When did you talk to Duane?" I asked, confused. She went back to picking out clothes. "I called him this morning to invite him to a party." "Party?" I spoke in a low voice so Karyn wouldn't hear us arguing. "It's my old friend, Casey. I haven't seen her in a couple of years, since before you and I, so I figured I could bring Duane and introduce him as my boyfriend," she explained, ever so casually, as if this was a normal thing to do. Lie about who your boyfriend is. "WHAT!?" I'm sure Karyn heard me now, but I didn't care. "A practice date will finally give him the confidence he needs," she boasted. "Well, I don't approve of this at all." I did my best to show her who was boss. My mistake. "Since when do you own me? I do as I like, especially after what you said about me last night," she grumbled. "I didn't saying anything bad about you," I swore. "I would never do that." "So, Duane was making everything up?" she asked rhetorically. "All I asked was if you guys went out for drinks," I explained desperately. "Did you complain about me not coming up to say goodnight?" Duane had really twisted my words. "I didn't complain, I just asked where you were." I hoped that she would see my side of the story. "Please, don't interrogate Duane again. It's bad enough you make him cook and clean for you. Treating him like a servant. You're a big reason why he has no self esteem." What had Duane been up to this whole time? How and why did he paint me as such a monster in her eyes? "This is crazy," I pleaded. "I don't know what's going on." She shook her head. "You've been very immature as of late." Now I was getting really mad. "According to whom? Duane?" "Stop blaming everything on him," she demanded, firmly. "It has to be Duane because you and I hardly see each other anymore." I then notice that she settled on the same sexy red cocktail dress that she wore to our one year anniversary dinner. "Hey, wait, this is the dress you wore on our anniversary." She rolled her eyes. "So? I can't wear it ever again?" I was so emotionally drained. "I don't know why you're being so combative." She sighed. "It's sad that after over one year together, you don't understand why I'm disappointed in you." "Disappointed?" That word stung so damn much. "Yes, and I think you should go now." Her eyes swelled. "Annabeth, please, let's not fight," I begged, reaching for her hand. Again, she rebuffed my advances. "Anthony, I'd like you to leave now." "Fine, don't let me be a nuisance," I huffed while departing. "Enjoy the party." "Tell Duane that I'll pick him up at eight," she called out just as I exited the apartment. *** I could not believe that had just happened. The girl of my dreams, who I loved dearly, was treating me like I was a villain. I returned home and immediately confronted Duane in his bedroom, bursting in without knocking. He was laying in bed, typing on his laptop. "Anthony, what's wrong?" I loomed over him. "Why you making shit up about me to Annabeth?" "I did nothing of the sort," he stammered. "We only talked about the party." "All of a sudden, out of the clear fucking blue, you like parties?" I asked. "Please, don't be angry with me, we're the best of friends," he whined. I was starting to see through all of his bullshit. "Fuck you!" I hollered. "I don't understand. Are you jealous of me?" he asked with a hint of arrogance. I snapped and closed the laptop on his fingers. Not too hard, but he still flinched. "Don't you dare tell Annabeth about this," I threaten as I stormed outside. I watched "Paranormal Witness" in the living room, trying to relax, but with no success. Around 8PM, I heard Duane's silly ringtone from inside his bedroom. Annabeth was usually prompt, so it must have been her texting to let him know that she was waiting outside in Karyn's car. I figured that she wouldn't come up and risk getting into another argument with me. Duane opened his door, looking as spiffy as he could in his formal occasion windbreaker. He had also wrapped his fingers with athletic tape, doing his best to milk a minor injury. I hadn't seen him in hours and I didn't know what to say to him at this point, but he snubbed me and walked straight out of the apartment before I even could say anything. Around 11PM, I checked Annabeth's facebook and saw that she had posted a bunch of pics from the party. She was with Duane, looking quite cozy together, in almost every photo. I took solace in that the most action Duane was getting from her in these photos was an occasional kiss on his fat, acne ridden cheeks. I kept forgetting that she was probably only hanging out with him out of pity. Annabeth had also given me the implication that tonight was the end of the experiment, so I decided to not wait up for them. They'll probably come to their senses and realize that they did me wrong. *** I was awoken several hours by the sound of someone groaning. I rolled over and checked my alarm clock, seeing that it was just past 2AM. The only time I could ever recall hearing noises like this in the apartment was back when Duane had food poisoning and was up sick all night, heaving on the bathroom floor. He was probably drunk from the party and throwing up. Serves him right, but there was no way I'd get back to sleep with this commotion going on, so I might as well go check on him. Hey, when Annabeth hears that I nursed him back to health, all with be forgiven. I staggered outside, still half asleep, and checked in the bathroom. The door was wide open and the lights were off, so he must have been sick in his bedroom, throwing up in his tiny wastepaper basket. What a mess this is going to be. He'll have fun cleaning it up in the morning. Then, I head his groans transition into whispers. I crept closer to his bedroom door and listened in. "Ohh...ohh...Anna...so...good...Anna...Anna...ohh...Anna...." he moaned. Could it be? I had to see with my own eyes, so I opened the door just a crack, trying to be as cautious as possible. Inside, I saw Duane on his back with Annabeth crouched between his legs, her head was bobbing up and down, the sound of slurping permeated. There was no mistaking her with that red cocktail dress on. She was giving him a blowjob. My girlfriend was sucking my roommate's dick with vigor while wearing the same dress she had bought for our anniversary dinner. "Annabeth...I'm gonna...I'm gonna cum...I'm cumming..." he bellowed, then he grimaced while her head continued to bob, assumedly draining his prick of ever last drop of cum. When she finally came up for air, it appeared from my angle that she was still stroking his shaft and maybe even massaging his balls. Annabeth Tutors My Roommate "Was that everything you dreamt it could be, baby?" she asked. He was panting. "Yes, it was incredible. You're amazing. This was my first time." "Such a crime that no woman has ever gotten to enjoy your big hard cock," she cooed. "Is it really that big or are you just being nice?" he asked bashfully. "You're three inches longer than Tony and like a full inch thicker," she flattered. She then kicked off her heels, hiked up her dress, and removed her pink lace panties. "But, I've never made love before," he stammered. "I don't know how to please you." "That's alright, baby, I'll take care of you. That's why I sucked you off first, so now you'll last longer before you shoot your second load." As she straddled him, I saw that she wasn't just giving him an ego boost, his cock was over the ten inch mark, even while semi-flaccid, and a lot thicker than mine. How has it taken him this long to get laid when he's been packing a monster in his shorts? She lowered herself and slowly impaled herself with sizeable manhood. She started to ride him while pulling her dress down to display her matching lace bra. "Mmm...baby...you're so thick...I love it..." she sighed, adjusting to his girth. Duane had practically gone cross-eyed as this was the time of his life. "Ohh...Annabeth...I love you...I've always loved you..." he cried. He then pulled her bra up and manipulated her nipples with his thumbs. "Mmm...nice and gently...that's how I like it...you're doing so good..." she praised. She leaned back, holding onto his undershirt, and was now bucking wildly. "YES! YES! YES! OH MY GOD! DUANE!!!" She obviously wasn't worried about me hearing them at this juncture. She was lost in a sea of ecstasy. He sat up, trying to suck on her tits, but his rotund physique made it difficult. "OH MY GOD! DUANE! OHHHHH... I LOVE THIS BIG THICK COCK!!!" She pushed him back down and started tearing at his shirt as she neared climax. "Ohh...Annabeth...you feel so good...I'm cumming..." he gasped. He nearly fainted as his cock erupted again, but she continued bucking until she reached orgasm. "YES! YES! JESUS CHRIST! I'M CUMMING!!!" She then collapsed on top of him, biting her bottom lip. "Mmm...what a stud you turned out to be...I'm so glad that I was your first..." I hurried back to my bedroom. Why didn't I confront them? I guess I was in a state of shock. *** I could sleep, but I couldn't listen to them fucking anymore, so I put my headphones on and listened to some music. I finally decided to emerge from my bedroom at 7AM. I felt liked I was punched in the gut by what I saw in the kitchen. Annabeth and Duane were making out, she had her tongue down his throat, she must have been giving lessons in that too because it looked like he knew how to kiss her back. He was in his lame flannel pajamas and she was wearing one of his oversized t-shirts. His sweaty hands were all over ass, gripping and practically lifting her off the floor. After another minute or so of them kissing, where they didn't either know or care that I was watching, she sunk to her knees and pulled his erect cock out of his pajama bottoms. He groaned like a walrus as she blew him for at least the second time in the past five hours. He palmed her head, his fingers still wrapped, and fucked her face while leaning against the refrigerator. I went back to my room, stewing, and waited until I heard the shower running before I went returned to the kitchen. Annabeth was alone, still in his shirt, fixing breakfast. "I guess we should probably talk," was all she had to say, in a very calm and direct manner. "Don't bother apologizing," I said right off the bat. "I wasn't going to apologize," she snapped back. "So, you've become truly cold hearted," I surmised. "Don't make yourself into a martyr, but we need to take a break," she clarified. "A break?" I asked. Like I was really going to fight for her heart at this point. "I owe it to myself to see where things go with Duane," she said with pride. "So, what, are you like in love with him?" I queried with genuine wonder. "I don't know." She sighed and sat down at the table. "It's complicated." I stared daggers through her. "Well, I'm not going to wish you guys my best." She was not intimidated by me. "I wouldn't expect you to." "What happens now?" I asked. She beamed. "We were planning on meeting his mother at the mall." I rolled my eyes because she always avoided my mom. "Seriously?" "She's going to help us pick out curtains for my bedroom," she explained. Duane then appeared in a flannel robe which matched his pajamas. I approached him and socked him in the nose. He fell to floor, his nose bleeding, and Annabeth quickly came to his aid. My actions only made their bond stronger and that was the end of my relationship with both of them. Over the next month, they stayed at her apartment mostly and he only dropped by our place to pick things up when he knew I wasn't around. I had warned him to keep a distance. The night before he was officially moving out for good, by happenstance, I came home from work about an hour early than usual and caught them fucking on the couch in the living room. I don't know if this was their attempt to rub my face in one last time. He was reclined on the arm of the couch while she rode him reverse cowgirl style. His shirt was unbuttoned and his gut was hanging out. She was nude, with her clothes scattered around on the floor. The were modest enough to give it a rest when they saw me and she covered her breasts despite me having already seen them bare countless times. I allowed them to finish packing his stuff up and they departed quietly without any farewells. Did I learn a lesson? Well, I'll never glorify a woman just because she fits my preconceived notions of who the girl of my dreams should be and I'll probably never fully trust one of my buddies again. The guy code means nothing when compared to a nice piece of ass.