This request comes from Literotica.
Anonymous said: Hello! I’ve been reading your stories for a few years now. I love your writing, and I was wondering if you’d write a story for me! Basically, I have this fantasy of fucking my boyfriend’s roommate (we’ll call him Kyle). He’s tall, kind of gingery blonde, and wears glasses. I picture him having a huge cock, although I’ve never seen it.
Behind His Back
“Can you pass me a beer, Linda?” Kyle asked me. I was sitting closest to the cooler in the living room, and so I flipped the top up and grabbed a beer for Kyle. I leaned over my boyfriend, Jeff, to hand the beer to Kyle.
“Here you go!” I said, trying to sound nonchalant as Kyle’s fingers brushed against mine. A delicious tingle crept through the tips of my fingers, working its way to my spine. I knew the feeling well because I felt it any time my fingers brushed against Kyle’s. Our eyes met knowingly. He could feel it too.
Jeff was absolutely oblivious to the chemistry between Kyle and me, and that was a good thing. Our chemistry had been growing each day since Kyle had moved in with Jeff the previous year. They had been friends before they became roommates, but once Kyle was moved in, I realized that I had a severe problem. I wanted to fuck my boyfriend’s roommate so fucking badly that it made me shake with lust when I thought about it.
Kyle was tall with strawberry blonde hair and a winning smile. He wore glasses that made him look insanely sexy in that intelligent nerd type of way that always drew me in. I could tell that he tried his best not to flirt with me, so much so that I started to wonder if he was even attracted to me or if the whole thing was just in my head.
I had been fantasizing about Kyle almost every time I masturbated, and it was starting to alarm me. Why wasn’t I fantasizing about Jeff? Jeff was a good-looking guy as well, and he actually loved me. He had been dating me long enough for our sex to go through the stages of being insanely sexy, then routine, and then almost dull. Jeff hadn’t been exciting me in the bedroom, and I had been turning to Kyle for inspiration.
“I lost track of how many beers I had,” Jeff announced. I thought it was odd since he’d been looking forward to watching the game all day. “I’m exhausted. I need to go lay down.”
“You had seven beers,” I answered, knowing how many I had handed him during the game.
“Why am I so tired?” Jeff said with a yawn. “I’m going to go take a nap. You guys enjoy the rest of the game.”
“Okay, babe,” I agreed, and Jeff leaned down to give me a gentle kiss. I tried not to think about how touching Kyle’s fingers had given me more of a thrill than a kiss from my boyfriend had. I waited for Jeff to leave the room before I looked in Kyle’s direction, admiring how the light from the TV reflected in his glasses.
“It’s been a crazy season this year,” Kyle commented when Jeff had left, his eyes on the TV.
“It sure has,” I replied, my voice somehow dripping with seductiveness. I hadn’t intended to sound like that, but my body and brain knew what they wanted. I just hadn’t acknowledged it yet.
Kyle turned to look at me, his pupils growing larger as he took in my features. I knew he loved my long, dark hair and my tan skin. I knew he appreciated my dangerous curves and my questioning brown eyes. I also knew that he was loyal to Jeff because they were roommates and friends. I didn’t dare say or do anything that might cause a problem, but my eyes were locked onto Kyle, and I couldn’t seem to look away.
“Why are you looking at me like that?” Kyle asked, and I really didn’t have a good answer.
“I don’t know. Maybe I’m just a bit drunk.” That was the best thing I could think of to say.
“You’re drunk? You only had two beers.”
“You should know I’m a lightweight by now,” I giggled a bit, the ways girls do when they flirt, but it happened reflexively. I wasn’t trying to flirt with Kyle, but it was somehow happening anyway, outside of my control or awareness.
“I thought you could do four or five beers at least!’ Kyle laughed nervously.
“How many have you had?” I asked, knowing full well that he’d had seven beers already.
“I lost count,” Kyle looked like he was trying to count his beers in his head.
“It’s weird that Jeff passed out already,” I said. Kyle paused and looked at me more closely.
“It is strange. He’s normally the one that can drink the most. Maybe he’s just tired from work?”
Kyle shrugged. “I can go to my room if you’d rather be alone.”
“No! No! Stay!” I said this much too loudly, and it definitely came out all wrong. Kyle looked at me questioningly, willing me to give him a reason to act. I could feel the thick sexual tension between us, my pussy twitching a tiny bit as I imagined what it would be like to suck Kyle’s dick or maybe even fuck him. I couldn’t do that, though. Could I?
“Okay, I’ll stay. The game is almost over, anyway, not that it’s much of a game.” We both turned back to the TV even though the game was clearly over. There was no way the trailing team could make up the point difference in the time left.
“Yeah, this is definitely a slaughtering,” I agreed.
“Should we change the channel?” Kyle asked.
“Yeah, sure, here,” I handed Kyle the remote control, and he began to flip through the channels. I adjusted myself in my seat, pulling the fabric of my shorts away from my underwear. I was very wet, and the wetness had saturated my panties completely. I thought about excusing myself to go to the bathroom but thought better of it, not wanting to ruin the moment I was having with Kyle.
“Here’s a movie I’ve wanted to watch. Have you seen this?” Kyle asked.
I looked at the screen and instantly recognized a movie that focused on comical relationships. I’d seen it before, and there were quite a few sex scenes in the film. It was a bold choice from Kyle, and I told him so, “I love this movie! I love all the sex scenes!”
“Yeah, some of them are so funny, right?’ Kyle laughed as if remembering them.
“Oh, you’ve seen this already too?”
“Yeah, but it’s one of those movies I could watch a million times.”
“Me too!” I said excitedly. I grabbed another beer for myself and one for Kyle. He popped the can and took a long swing as I opened mine and took a tiny sip. I wanted to be relatively sober for what was about to happen next. I already knew what I wanted, and I was just tipsy enough to go for it.
“This sex scene is so ridiculous!” Kyle laughed as the movie moved into the scene where the protagonist tries to have sex with her boyfriend’s best friend. Kyle couldn’t have planned it better. My pussy was absolutely aching for something to happen. Still, Kyle sat there on the couch just watching the movie like an idiot.
“Yeah, she has no idea that they are about to have sex, but I like the way it happens,” I explained to Kyle. He suddenly turned and looked at me with an intensity that I had never seen from him before.
“Kyle?”
“Yes?”
“Do you think you could help me with something?” I asked.
“Sure, what is it, Linda?”
“I have this kink in my neck. I’m not sure why, but it really hurts. Do you think you could massage it?”
“Me? What about Jeff?” he asked me quickly, and I started to doubt myself. Maybe I had misread the situation. Maybe Kyle wasn’t into me, or he was too afraid of Jeff to do anything.
“I’m not asking you for anything off-limits,” I said slowly. “My neck really hurts.”
“Okay, come sit right here on the floor in front of me.”
“Okay!” I moved quickly to the spot in front of him, placing a pillow on the floor to cushion my butt. Kyle’s hands moved to my neck, and the feel of his hands on me was so fucking good. I was finally getting a taste of what I wanted, and I was enjoying the sensation of his skin touching mine, even if it wasn’t a sexual touch. I was exhilarated, letting the thrill of doing something wrong overtake my senses. I knew that I shouldn’t be doing this, and I knew I had an agenda. Kyle was playing stupid, but I was sure he knew what I wanted. He could sense my need as his fingers found the knot in my neck and released the pain.
“That feels so good!” I moaned, making sure to let my voice sound as sexy as possible. The thought that Jeff could wake up and find us like this was more of a turn-on than a deterrent. I had wanted this for so long, and I really wanted to fuck Kyle. I wanted it more than I had been willing to admit to myself until that moment. “Can you rub the rest of my back?”
“Maybe you should lay down on the couch,” Kyle suggested, and I did so. “Take off your top too so I can get to your back. Your shirt is getting in the way.”
I knew that I shouldn’t take my shirt off, but I also knew that I wanted to and that I would do it anyway. I still had my bra on, and that was enough. Kyle’s strong hands kneaded the sore muscles in my back. I moaned appreciatively, letting him know that his touch was welcome. He massaged my lower back and then my legs. He moved back up to my butt cheeks, and I was shocked when he began to knead first one cheek and then the other with both of his hands.
I moaned loudly, forgetting all about Jeff as the pleasure from the massage relaxed me fully. I didn’t even flinch when Kyle’s hands grazed my pussy and asshole. He continued to massage my ass cheeks, kneading them until he finally rubbed my asshole through the fabric of my shorts and panties.
“You want to take these off so I can really get in there?” Kyle asked as if it were perfectly normal.
“Okay, but I don’t want Jeff to get mad if he sees this happening.”
“Let’s go to my room. I can finish the massage there.” He helped me up, and we made our way to his bedroom. He locked the door as I pulled all of my clothes off and laid on Kyle’s bed completely naked. “I’m ready!”
“I see that! Let me start where I left off.” His hands slid to my butt, and he parted my cheeks. “You have the cutest, little butthole. Would you be upset if I used my tongue as part of the massage?”
“I suppose it’s okay as long as it’s part of the massage,” I said with a naughty lilt to my voice. Kyle bent down and licked my asshole with his tongue. His hands continued to massage my butt cheeks as he held my cheeks open for his tongue. “Oh, that feels good!”
“You taste good,” he complimented me. His tongue was wandering down to my pussy, and I said nothing as it traced the path of my frenulum to my pussy hole. His tongue darted inside and then back out. I moaned, hoping that he would continue. I wasn’t ready for the massage to be over.
“How would you feel if I used my cock to massage this little pussy. I think that’s what it needs to feel good.”
“I think you’re right!” I agreed, happy that I would get to feel Kyle the way that I wanted to.
He climbed on top of me, and I could feel him struggling to push his thick cock inside of me. I looked back over my shoulder to see that Kyle’s cock was absolutely huge! I wasn’t sure if I would be able to take it. Jeff’s cock wasn’t that big, and it fit easily inside of me. He slid into me, but nothing could have prepared me for the way that Kyle’s cock felt inside of me. It was a revelation!
I instantly began to cum, my moans growing louder and more urgent with every thrust of Kyle’s cock until I was clawing at the sheets and holding onto them for dear life. I screamed, letting all the stress and lust I’d been nursing for Kyle out into the open. I tried to crawl away from him because the pleasure was so much it was overpowering to me. I couldn’t believe the things Kyle was making me feel, and I wasn’t sure that I could actually handle them. I screamed again, this time so loudly that I realized Jeff could probably hear me.
Kyle didn’t seem concerned. He gripped both of my shoulders and pushed my face back into the bed. He took control of my pussy, fucking it hard and fast the way porn stars do. I had never been fucked like this. I had made love with Jeff and all of my other boyfriends before this. Now I was being manhandled and treated like a fuck buddy. I wasn’t used to it, but it was the best sex that I had ever experienced. Kyle’s thick cock stretched my pussy out until I was cumming, cumming, and cumming again. I was getting weak and tired, but Kyle didn’t relent. He knew exactly what he wanted from me, and he took it.
Kyle pulled his hands from my shoulders and put a finger at the entrance to my ass. I should have known he would finger it, but I had never had my ass fingered before, and I wasn’t ready for it. I didn’t think I was the kind of girl who liked anal, but I wasn’t sure because I’d never actually tried it. Kyle’s finger penetrated my ass, and I let out a sharp pain cry as he entered. His cock was still pounding my pussy, and I found that when I was cumming I scarcely noticed what was happening to my ass. He had his finger all the way in, and to my shock, it didn’t hurt at all. In fact, it felt pretty good.
Kyle pulled his finger out of my ass, and for a moment, I was disappointed. I wanted it back inside of me! I cried out, trying to tell him but unable to form words. I was cumming again, even though I wasn’t sure how it was possible. I had never cum so much in one sex session. Kyle went back to fingering my ass, this time with two fingers. It was feeling even better than it had with one finger, and my pussy was still having orgasm after sweet orgasm. I was a mess beneath Kyle, clawing at the bed and at myself, overwhelmed by the pleasure he was giving me. I forgot all about Jeff. I didn’t care that I had a boyfriend anymore. All that mattered was this perfect dick inside me and those two fingers opening my asshole up.
I could feel my asshole stretching to accommodate Kyle’s fingers, and I wondered just how much it would stretch. I wondered if Kyle would test it with his thick cock, and part of me wanted him to. Part of me wanted him to manhandle me and use me in ways I’d never been used before. I would never let Jeff fuck my ass, but it felt like a natural progression with Kyle. I felt like I owed it to him for making me feel so fucking good.
“I want you to fuck my ass!” I cried, not believing my own words. I had never said such a thing in my life, but at the moment, it felt like the right words. I wanted it. I wanted to know if Kyle would be the one that would take my anal virginity.
“Of course! I never knew you were this kinky, Linda. I thought you were a little priss, but you’re nothing like I thought.”
“I’m not?”
“No, you’re fucking awesome. Hold still. I’m going to push it in,” Kyle warned me. I held still for Kyle, letting him work his massive dick into my tiny, virgin asshole. It definitely hurt a lot more than I was anticipating, and he could tell by the way my entire body tensed up that I was in pain. “Relax, Linda. It’s just a dick in your butt. You can do it.”
“I’m trying!”
“Relax your muscles,” he coached me, and I listened, breathing slowly and carefully until my body relaxed around Kyle’s huge cock. He was inside me, although not very far. The head of his dick was barely inside of me, and it hurt like a bitch. I was just about to tell him to stop when he pushed his cock even further into my ass.
“Owwwww!” I screamed.
Kyle gave an evil laugh that concerned me. He held me down, a hand still on each of my shoulders. My face was buried into the mattress. I kicked my legs like a toddler that didn’t get her way. I was screaming, but Kyle muffled my cries of pain with a pillow he pushed over my head.
“Sorry, but if you’re going to be that loud, I’m going to have to silence you!” Kyle sounded so sadistic now! I could feel his cock growing even bigger inside of my asshole, stretching me out in ways I had never dreamed possible. His cock was pushing deeper into my ass with every stroke, and I was screaming as loudly as I could, but no one could hear me.
Kyle took what he wanted from me, using my asshole as if I was some whore he paid for, not like the friend I actually was. I would tell Jeff about this. I would explain how Kyle held me down and forced me to take his cock in my ass. I would leave out all the parts about me flirting back so that Jeff would come after Kyle and destroy him, just like Kyle was destroying my ass now.
The pain was intense, and I was crying real tears as I felt Kyle’s balls slapping my clit. He was utterly stuffed inside of my asshole, pounding the shit out of me like I didn’t matter. The way his balls hit my clit with every stroke began to wear me down until the pleasure began to overtake the pain. I wasn’t ready for it when my orgasm hit. I had no idea that women could even cum from anal sex, but there I was taking Kyle’s fuck, and the next moment, I was cumming harder than I had ever cum before.
Noises came out of me that I had never heard before. Snot shot from my nose and all over the sheets beneath me. I could feel the wetness beneath me, and I knew that my pussy had squirted the way it sometimes did if I came in just the right way.
“I’m going to cum!” Kyle screamed, and I braced myself, not knowing where he was about to cum. He pulled his cock from my ass, and he moved quickly to my face. He grabbed my shoulder and flipped me on my side, taking aim. I should have closed my eyes, but before I had a chance to, a huge glob of cum was in my eye. He was giving me a facial! It was disgusting! No man had ever dared to cum on my face, and I hated him for degrading me in this way.
“What are you doing?” I asked, but it was apparent what Kyle was doing. He was using me to fulfill his own perverted and disgusting fantasies.
“Wow, Linda. You are an amazing fuck. Your asshole is so tight!”
“My eye burns!” I screamed, reaching up to touch the pain.
“Here’s a towel!” Kyle said urgently, handing me a towel as quickly as possible.
“Thanks,” I said, grabbing the towel and dabbing my eye. I wondered if I should tell him he was the first man to fuck my ass, but I decided not to. I didn’t want him to think that he was special or something. I was still with Jeff.
“We shouldn’t have done this,” I said instead. “Look, things got a bit out of control. I don’t think we should tell Jeff.”
“No, we shouldn’t. If we tell him, then we won’t be able to keep fucking.”
“That’s not what I meant,” I began, still trying to get the cum out of my eye. “I don’t know if we should do this again. I think this was a one-time thing. Okay?”
“Why just a one-time thing? I mean, I will respect your wishes, but that was amazing sex. I definitely want more from you, Linda.”
“I don’t know. I just hate sneaking around and lying.”
“Well, you already fucked me. It’s not like another couple of times will hurt,” Kyle reminded me with a wink.
“Actually, that did kind of hurt. I’m not used to being fucked so roughly, and my eye still burns.”
“It seemed like you liked it. You came a ton. My bed is all wet from when you squirted,” Kyle reminded me.
“I know. It’s just…I think I made a mistake. What if Jeff had woken up and caught us?”
“He didn’t.”
“Well, he could have.”
“I have a confession,” Kyle said slowly.
“What?”
“I actually drugged Kyle’s beer so that he would pass out. I wanted to see if I could fuck you because I’ve wanted you for so long.”
“You have?” I asked, perplexed by this piece of information.
“Yes, and I still want more. This time I want you to bend over the bed right here.” He pointed to a spot.
“You drugged Jeff?” I asked.
I was horrified by this.
“Yes. He’s going to be out for a while, so I suggest you bend over the bed and take some more dick while we have the time.”
“I don’t know. I don’t like that you drugged him! That’s terrible.”
“Is it really?” Kyle asked, now behind me, massaging the spot on my neck that had started the whole thing.
“Oh, that feels good,” I cooed.
“Go bend over the bed. I want to fuck your pussy this time.”
I thought about it, and I’m not proud of it, but I did as Kyle asked. “Well…okay, I guess,” I said as I moved to the bed and bent over for him. I did as Kyle asked, and before I knew it, his dick was up inside my pussy. I came even harder than during the first fuck. I knew it was wrong, and I knew that I was a cheater, but honestly, I didn’t care. The orgasms that Kyle was giving me were worth it, and what Jeff didn’t know wouldn’t hurt him.