I met Rick several years ago, as the friend of a friend. At first I found him mildly attractive, but that quickly changed as I discovered his personality. Rick was a cocky, overconfident bastard, who seemed to take delight in showing off how much cooler he was than everyone else. It might have been more tolerable if not for the fact that he seemed to love making me feel like a child by comparison.

I remember the first time that we hung out. Despite the fact that we had just met, he took it upon himself to describe his recent sex life in extremely graphic detail. I’m not a prude or anything, but he was still basically a stranger at that point and I really didn’t want to hear it. Rather than accept that I was offended, though, he acted as if I just didn’t understand. From that point on, whenever he used a slang term for anything sexual he’d explain to me what that term meant, usually in the most patronizing voice he could muster.

I’d like to say that we kept it civil, but that would be a lie. The truth is that I did my best to keep it civil, and he did his best to antagonize me. It was as if he was trying to push me to the point where I’d lash out and make a scene, which I did not want to do.

As the years passed, I found myself avoiding situations where I knew that I’d have to be around him. It really bothered me, as I felt myself drifting away from my friends, which seemed completely unfair. I didn’t see why I had to be lonely just because he couldn’t manage to act like a decent human being. I think this sense of injustice was a big factor in why I said yes when Kate invited me to her place to hang out.

I knew that Rick would be there. He was close friends with Kate’s boyfriend Jack; he probably spent more time at their place than at his own. Still, I went way back with Kate, having been her friend since grade school. I was no longer willing to sacrifice our friendship because Rick couldn’t stop himself from being a douchebag. As I headed over there I made a promise to myself that I wouldn’t take his shit tonight; that for once I would stand up for myself.

I got to Kate’s apartment around 8:00. Rick was already there, watching TV with Kate’s boyfriend Jack in the living room. Politely, I greeted Jack. Less politely, I ignored Rick and took a seat.

“We haven’t seen each other in months, and you can’t bring yourself to say ‘hi’?” Rick laughed. “You’re going to hurt my feelings.”

I thought about saying something rude, but didn’t want to give him the satisfaction of getting me angry. Instead I just shot him a cold, emotionless smile, hoping to convey that I realized he was here but didn’t care. He laughed back, as if to convey that he didn’t care either.

“You two play nice,” Kate requested, putting on her coat. “Jack and I are going to pick up the pizza; we’ll be back in 20 minutes.”

“Uhm, what?” I squeaked. I didn’t want Kate to leave me alone with Rick, but didn’t want to admit it in front of him. It wasn’t that I was afraid of hurting his feelings, but rather that I suspected he’d be proud of knowing that he had the power to make me feel uncomfortable.

“It’s this new place over in Glenside,” she explained. “Their pizza is awesome, but they don’t deliver this far. Don’t worry, we’ll come straight back.”

Before I could formulate a strategy to make her stay, they were out the door and I was stuck in the apartment with Captain Douche. He glanced over at me and shot me a cold smile, mimicking the one I had shot him earlier. I wanted to disappear for 20 minutes, but couldn’t think of an excuse.

“I’m surprised you made it,” he taunted. “I thought for sure you’d be having a tea party with your favorite dolls or something.”

“You know what, Rick?” I snapped. “Fuck you. I’m not some sheltered little school girl you can push around. Just because I understand the concept of discretion does not mean that I’m a fucking child. This might shock and amaze you, but normal people don’t go around describing the disgusting things they do in the bedroom to strangers.”

“Right, that’s what it is,” he laughed sarcastically. “You’re totally experienced, you’re just modest. Tell me, little girl, have you actually deluded yourself into believing that or are you just comfortable lying?”

“It’s not a lie!” I protested. “Just because I’m not some whore like the women you date doesn’t mean that I need everything explained to me as if I were ten years old.”

“Comparing yourself to the women that I date?” he asked. “Is that what this is? Are you just a little bit jealous?”

“Fuck you, you couldn’t pay me enough to date you!” I spat.

“Fine by me, you’re not my type anyway,” he laughed back. “I don’t date virgins.”

“I’m not a virgin!” I cried.

“Hey, whatever,” he answered nonchalantly. “Honestly, it doesn’t really matter. You’re too fragile, I’d just end up breaking you, and then I’d feel bad.”

“I call bullshit on that,” I retorted. “Judging from the things you claim to do to the women you date, I’m guessing you’re used to passive little children that don’t fight back. You couldn’t handle an adult woman like me; I’d crush your puny little ego.”

“Be careful there, little girl,” he warned. “You’re not fooling anyone, and you’re damned sure not intimidating me. We both know that I’d destroy you, claiming otherwise could very easily bite you in the ass.”

I knew he was right. As much as I wanted to play the part of the strong, independent woman, it wasn’t who I was. I might not have been the sheltered little girl that he liked to portray me as, but it was probably closer to the truth than I was comfortable admitting. Still, I wasn’t about to give him the satisfaction of admitting that he was right.

“You don’t scare me, you piece of shit,” I hissed.

“That’s nice,” he mocked. “But hey, since you’re so unafraid, why not prove it?”

“Fuck you, I don’t have to prove anything to you,” I spat.

“Wow, I had no idea you were so scared. I mean, I expected you to bitch out at some point, but to run away before you even hear the details? Man, I had no idea I was that intimidating.”

“I’m not scared,” I insisted, trying to sound as cold as possible. “I just don’t have any interest in proving myself to a piece of shit like you. If it makes you feel any better, go ahead and tell me your details. I really don’t care either way.”

“Of course you don’t,” he answered dryly. “I’m sure I have no influence on your life at all. Still, I’m bored, so here’s what I propose: A simple contest, lasting until one of us admits defeat. If I give in first, then I’ll admit that you’re a better, stronger person than me, and never forget my place around you again. If you give in first, you’ll do likewise.”

“Here’s what you get,” he continued. “I’ll consent to anything that you can force upon me. I won’t call the police, I won’t seek retribution, and if any third party steps in to object I’ll defend you, claiming that I specifically asked you to do whatever it is that they object to.”

“In your dreams, you fucking pervert,” I laughed.

“I can’t believe that I’m saying this to you of all people, but get your mind out of the gutter. I’m not talking sex, I’m talking anything. You can beat the shit out of me in front of Kate and Jack, and if I can’t force you to stop I’ll have to tell them that I asked you to do it. You’d finally be able to get your revenge on me for all those times I made you feel like a child, and I’d be the one that looks like a sick freak who enjoys it.”

“What’s the catch?” I demanded.

“I don’t know that ‘catch’ is the appropriate word,” he explained. “But if it is, the catch is that the contest is fair. I consent to anything you can force on me, you consent to anything I can force on you. The same rules apply both ways.”

“Bullshit,” I replied. “You’re twice my size, that’s hardly fair.”

“I suppose you are pretty weak compared to me,” he sighed. “Truth be told, I wasn’t planning on using physical force offensively, but if it makes you feel any better I’ll take it off the table. You’ll be able to physically assault me, but I won’t be able to physically assault you. All I need is for you to admit that you’re so weak that you need an advantage to keep it interesting.”

“There is no way in hell that I’m admitting that,” I growled.

“Wonderful, then we have an agreement. The contest lasts until one of taps out. Obviously, asking for help, explaining the arrangement to anyone else, et cetera, are all against the rules. You may begin whenever you’re ready.”

I panicked a little, worried that I was in way over my head. I thought about pointing out that I had never agreed to anything, but I knew that he’d take that as evidence that I was afraid and I couldn’t give him that satisfaction. Besides, the desire to get in just one solid shot was overwhelming, regardless of the cost.

Walking over to him, I took a stand less than a foot away from where we has sitting. As I balled my hand into a fist he looked up, a shit-eating grin on his face. Focusing the hatred that I had built up over all the years that I had known him, I closed my eyes and punched him as hard as I could in the face.

The pain was incredible. I had never thrown a punch before, and I think I may have actually managed to break a finger or two. Still, it would be worth it if the pain I inflicted on him was even half of the pain that I inflicted on myself. Opening my eyes, I hoped to see him sprawled out on the floor, clutching his face in pain.

To my horror, he was not on the floor. He was sitting exactly where he was before, the same fucking smile on his face. I could see that the area where I connected was turning red, but he didn’t seem to indicate even the slightest pain.

“Hey, while you’re up, can you check the windows?” he asked. “I think I felt a gentle breeze on my face a second ago.”

“Fuck you!” I shouted, lunging at him. Ignoring the pain I tried to wrap my hands around his neck and choke him. Unfortunately, his neck was thicker than I had anticipated, and I was unable to reach all the way around.

“You know, I didn’t expect a challenge or anything, but this is just sad,” he sighed, sounding more bored than anything else.

Without showing any sign of exertion, he casually grabbed each of my wrists and pulled them down away from his throat. I tried to struggle, of course, but he was too strong for me. Giving up on choking him, I tried to get away, but he wasn’t letting go. He spun me around and sat me on his lap, and then just held me there, not even acknowledging my attempts to free myself.

“Let me go you bastard!” I shouted.

“I’d be happy to, just as soon as you admit defeat,” he calmly answered. “I knew that you would eventually, but to be honest, I’m amazed that you gave in so quickly. I guess you were more of a frightened little girl than even I had realized.”

“Fuck you, I’m not admitting a goddamned thing,” I hissed.

“Fair enough, but now I’m concerned,” he laughed. “You’ve gotten yourself all worked up, and I don’t want to see you hurt yourself. I think you need a time out. Sit here quietly, and when I feel you’ve calmed down enough I’ll let you go.”

“I swear to god, I’m going to tear your fucking throat out,” I promised.

“I’m sure you will, but not until your time out is over. Incidentally, your time out does not start until you sit quietly like a good girl. Each time you speak, each time you struggle, you’re just prolonging it.”

“Fuck you and fuck your time out!” I screamed. For the next several minutes I did everything I could to escape — I struggled, I kicked, I tried to bite him, but nothing seemed to work. Not only was I unable to free myself, I wasn’t even able to elicit a reaction from him. No matter what I did, he just calmly sat there, holding me in place while watching the television.

“I can keep this up all night,” he sighed. “And honestly, I don’t mind. However, you might want to consider something. This time out isn’t going to end just because Jack and Kate returned home. If you still haven’t learned to behave yourself by that time, you’ll be explaining to them how you actually wanted to sit on my lap.”

As much as I hated the idea of submitting to his time out, the idea of telling Kate that I was sitting on his lap voluntarily made me sick to my stomach. Between that and the growing realization that I had virtually no chance of squirming my way free, I gave up and ceased my struggles. I hated it, but I had no choice.

The next several minutes were tremendously awkward. Rick didn’t say anything; he simply sat still and watched television. As I relaxed my body, he loosened his grip a little, but not enough that I felt confident trying to escape again. I wanted to ask him to release me, but didn’t know how to pull it off. I was afraid that by asking I would sound too submissive, and that he might extend the time out just for the crime of speaking.

Eventually, we both heard the sound of Kate and Jack’s voices outside the building. Panicking a little, I looked at him and tried to beg him with my eyes to release me. He looked back with mock warmth and laughed a little.

“Have you learned your lesson, little girl?” he asked, patronizingly.

“Yes,” I growled through clenched teeth. “Please release me now.”

“With that tone?” he laughed. “If you had asked nicely, I would have, but I think you still haven’t learned your lesson. Still, I don’t want to embarrass you in front of our friends, so I’ll take care of this correction quickly.”

Again tightening his grip on my wrists, he flipped me over so that I was bent over his knee. Instinctively I looked up to see him raising his hand into the air. Before I could say anything, he brought it down hard against my ass.

I yelped in pain, but he ignored it and spanked me again. It was humiliating and surprisingly painful; he wasn’t play-slapping, he was hitting hard. As he continued to spank me I thought about giving up, but couldn’t bring myself to do so.

After several seconds of the abuse, he stopped and released me without saying a word. I jumped back away from him, and braced myself to attack him. Once again, rather than defending himself he just sat there, looking bored.

“You’re free to do as you please, but think about this” he explained. “In a few moments, Jack and Kate will be home. If you act up again, you’ll be in the awkward position of explaining to them that you really just wanted to sit quietly on my lap like a good girl.”

He was right, and I knew it. Choking back my pride, I took a seat on the couch. The damage done by his spanking made it incredibly uncomfortable, but I forced back the tears and did my best to ignore the pain.

Kate and Jack entered their apartment, bringing two pizzas and a case of beer with them. In a way, it was comforting to see them as I thought Rick would be less likely to try something with them present. At the same time, I was worried that if he did try something and succeed, I’d have to pretend that I wanted him to. Not wanting to think about it, I helped myself to a beer.

“Well, I’m glad you two managed to not murder each other while we were gone,” joked Kate.

“You worry too much,” Rick laughed. “Hell, just a minute ago she was sitting calmly on my lap.”

“Yeah, like anyone’s going to believe that,” I interrupted. I didn’t have a ton of advantages over him, but I definitely had more credibility. I hoped that the fact that they would believe me over him would hurt him in some way, but he seemed unfazed.

“Whatever, I’m just glad you two can be civil to each other,” Kate explained. “You’re both our friends, and we don’t want to lose either of you.”

Kate’s words touched me. As angry as I was at Rick, I remembered that she was still my friend, and it wasn’t fair to her to suck her into our fight. I resolved to try to ignore Rick for the rest of the night and hope that he would have the common decency to do the same.

The next few hours weren’t too bad. I don’t know if it was Kate’s words or something else, but Rick actually managed to behave halfway decently. We sat around, watched a movie, and drank. I drank a bit more than I normally would; I think mostly as a way to deal with the stress I was feeling.

After several beers, I was beginning to think that the whole thing was silly. Rick was apparently capable of being a nice enough guy, and I was starting to wonder if we had possibly just gotten off on the wrong foot and never recovered. I was seriously considering apologizing to him and asking if we could get a fresh start on our relationship when he took it upon himself to remind me why I hate him.

“So,” he announced. “While you guys were grabbing the pizza, Sara shared a secret with me. It turns out that our good friend has never been fucked in her ass. I know it’s not too shocking, but I thought you guys should know.”

“You’re fucking lying,” I hissed. I couldn’t believe that I had entertained the thought of making up with him.

“I’m sorry, Sara, are you telling us that you have been fucked in the ass? When did this happen? Did you enjoy it?”

“Shut the fuck up, you piece of shit,” I shot back at him. “I mean that you’re lying about me telling you that. I didn’t tell you a fucking thing.”

“Be that as it may,” he continued, “you’re not answering the question. Perhaps you don’t understand it. You see, Sara, when a daddy loves a mommy very much and he wants to show her how much he loves her, he sometimes puts his penis in her vagina. And sometimes, when he doesn’t love her quite as much and wants to show her that, he puts it in her asshole instead. Understand?”

I don’t know if he had just finally pushed me too far or if the alcohol had inspired courage in me that I never knew existed, but I was sick of it. Normally in a situation like this I would quietly shrink away and wait for him to move on, but that was no longer an acceptable solution. I knew what I had to do. I would beat him to a pulp, make him tearfully apologize for his accusation, and then force him to tell Kate and Jack how he had begged me to deliver the beating. For once, he’d get what he deserved.

Gathering my strength I rose to my feet and approached him. Thinking about my strategy, I decided that this time I’d aim for his throat. I’d have to use my left hand this time, as my right still hurt like hell, but his throat would be softer and would likely hurt him worse. Looking him dead in the eyes, I focused my hate as he returned my stare with the same idiot smile he had worn before.

Fantasizing about my victory, I drew my hand back. This time I didn’t even get to throw the punch; before I could bring it crashing into him I felt his hand wrap around my right wrist. With a single movement he pulled me down, once again bending me over his knee. Twisting back, he pinned my wrist into my back, holding me helpless in place.

“Dude, taking it too far,” Jack interjected.

“Relax,” Rick explained. “Maybe it’s her emotional immaturity, but I think we often forget that our Sara here is a grown woman, capable of making her own decisions. She just wants a more concise explanation of anal sex, and very much wants to be on my lap right now. Isn’t that right, little girl?”

“It is,” I hissed. It wasn’t, of course, but there was no way that I was going to let him win.

“And you’re sure you don’t want help, right?” he continued, rubbing it in.

“I am,” I admitted. “Please do not help me. This is what I want.”

“Good girl,” he laughed. “Now, to clarify. As I said, when a man loves a woman, he fucks her in the cunt.”

Without warning, Rick slid his hand down the back of my pants and into my panties. I clenched my thighs shut, but it was no use — he forced his hand between them with ease. Horrified, I felt his fingers force their way into my vagina.

“You see, Sara, this is your cunt. You might be wondering why it’s so damp. Don’t worry, you didn’t just piss yourself! When a woman is with a man whom she is hoping will fuck her, her cunt gets nice and wet to lube itself up so that he can fuck her.”

Humiliated, I went limp. He removed his fingers, then pulled his entire hand out of my pants and held it up in the air. Seeing his fingers glisten in the light with my juices I felt a deeper sense of shame than I had ever felt before.

“And you thought she didn’t want this,” he laughed. “Look how wet this bitch is!”

I looked to Kate, hoping that she’d see through the charade and help me. As our eyes met, though, I saw no sympathy — only disgust. Mortified, I buried my head next to his leg, hoping this would end soon.

Rick again slipped his hand into my panties. Instinctively, I parted my thighs slightly to allow him back in, without even thinking about it. Remembering what was happening I clamped my thighs shut again, hoping he didn’t notice. It didn’t matter, though, as he clearly wasn’t planning to repeat himself. To my horror I felt his finger poking between my butt cheeks. Looking up at him, I pleaded.

“Rick, please don’t do this,” I begged, keeping my voice low enough that Kate and Jack wouldn’t hear. “I know we’ve had our differences, but this is crossing the line. Please just let me go?”

“Sure thing,” he answered, mirroring my volume. “All you have to do is admit that you’re weaker than me in every way, that you can’t possibly stand against me, and that you are utterly defeated. Do that, and I’ll remove my hand, release you, and we can both go on with our lives.”

“Frankly, I’d prefer to be dead,” I sneered. I knew that I’d regret it, but I refused to let him win. “Do your worst, you fucking faggot.”

“You got it,” he laughed, pushing a finger into my anus. The physical pain was surprisingly minimal, but the humiliation was intense. As he wormed it deeper into me I was excruciatingly aware of the fact that my good friend Kate and her boyfriend were witnessing every moment of my degradation. Again I considered surrendering, but decided against it. I rationalized that if I could withstand this indignity, I could withstand anything — eventually he’d run out of shit to pull and I’d be free to retaliate.

“Back to our lesson, little girl,” he continued, apparently oblivious to my inner turmoil. “Now, women love being fucked in the cunt, but sometimes they haven’t really earned that. For that special situation, nature gives us a second choice — the asshole. It’s not a perfect solution, of course. Some women, mostly the exceptionally slutty ones, actually love getting fucked in the ass, too. Still, we manage.”

“Dude, are you actually in her ass?” Jack asked, sounding more surprised than anything.

“Why don’t you answer that question, Sara?” Rick suggested. “Am I in your ass? How many fingers? Most importantly, though, am I doing this against your will or do you actually want this?”

“God damn it so fucking much,” I sighed under my breath. I absolutely did not want to answer his questions, but I couldn’t let him win. Realizing that he was only doing this to humiliate me, I resolved to show no shame, hoping that he would give up once he saw that it wasn’t working.

“He has one finger in my ass,” I announced. “And yes, that’s how I want it. I like it because it’s much thicker than his tiny little cock.”

I had hoped my verbal jab would somehow level the playing field, but it had failed to do so. Jack seemed to find the whole situation confusing yet funny, Kate looked disgusted with me. Rick, however, seemed to actually enjoy the joke.

“I had no idea you were such a size queen,” he laughed. “And now I feel bad; one finger can’t be enough to satisfy you. Allow me to make up for it.”

Rick forced a second finger into my asshole. This time, the pain was more noticeable. I grunted in discomfort.

“Dude, you’re sure you’re not hurting her?” Jack asked.

“It’s just a couple fingers, I’m sure she’ll live,” Rick answered, sounding irritated that he would have to explain himself. “Though, I guess you have no way of knowing it, what with her pants blocking your view. Let’s fix that.”

Removing his hand from my pants, he slid it under me. With fluid motion, he unbuckled my belt, unbuttoned the pants, and slid the zipper down; all while keeping me restrained with his other hand. I tried to struggle, but he was entirely too strong.

“Okay, you’re taking this way too far,” Kate interrupted. “Stop it. Now.”

“You guys really need to stop treating Sara like a baby,” he argued, chuckling at the irony of his statement. “She’s an adult woman, and she’ll let you know if she wants me to stop.”

“Yeah, babe,” Jack agreed, his tone implying that he was enjoying my humiliation more than he should have. “Let’s relax a bit. If Sara asks him to stop we’ll make him stop, but otherwise, I really don’t think we should interfere.”

Kate glared at me, as if to demand that I call an end to it all. I wanted to explain the situation to her, to let her know that I really did want it to stop but I couldn’t without letting Rick win. As my pants and panties slid off, her expression changed to outright disgust. I felt terrible for putting her in such an awkward position, but I had no way to fix it.

With my pants down around my ankles, Rick had a much easier time getting his fingers back inside me. It didn’t hurt quite as much, but the pain was still there. While Jack watched on, Rick leaned down and positioned his mouth next to my ear.

“This may hurt you more than you can handle if we don’t lube you up, you know,” he whispered into my ear.

“Then lube me up, moron,” I hissed back, keeping my voice low.

“I’d be happy to,” he answered, “but unfortunately I don’t actually carry lube with me at all times. I’d ask them for some lubrication or something, but you know how I am — I wouldn’t want to make a scene.”

“Gee, guess you didn’t think your clever plan all the way through, dumbass,” I spat. “Now let me the fuck go.”

“I think you misunderstand me,” he sighed. “I’m not saying I won’t go any further without lubrication, I’m just letting you know that it’s going to hurt like hell if I do. Either way, I’m not stopping until you admit defeat. I’m not completely without mercy, though. If you ask our good friends for something to lube you up, I’d be willing to apply it.”

“You must be joking,” I sneered back at him.

“Have it your way,” he laughed, forcing his fingers deep into me. I cried out as the pain coursed through me. I knew that he wasn’t going to stop until I surrendered, and I knew that if he continued I’d be unable to handle the pain. I had no choice. Choking back tears of humiliation and pain, I looked up at Kate.

“Kate, can I borrow some lotion or something?” I asked, trying to mask the shame in my voice.

“Sara, you can’t be serious!” she exclaimed. “You need to stop this right now. You can’t possibly want this!”

“I think it’s entirely possible that she wants this,” Rick interrupted. “But let’s find out for sure. Sara, are you enjoying this? Would you like me to continue?”

“Yes, Rick,” I growled, glaring at him with perfect hatred. “I am enjoying this very much.”

“See honey, she’s cool with it and we should be too,” Jack contributed. “I’ve got some hand lotion in the bedroom, I’ll grab it.”

“Thanks, Jack,” I sighed. I was quickly beginning to hate him as much as Rick.

Jack quickly returned with his lotion and handed it to Rick. Not wasting time, Rick squirted a generous amount directly onto my asshole and began to work it in. I jerked back a little as the cold fluid made contact with my skin, but then began to relax. In a perverse way, the lotion was actually very soothing on my sore flesh.

After spending several seconds rubbing the lotion in, Rick began rhythmically pumping his fingers in and out of my ass; slowly at first but with gathering speed. It’s strange, but for the first time I began to view his actions as sexual in nature — up until that point it felt like simple physical humiliation. I wanted so badly to make him stop, but I was powerless to escape. Worse yet, my body was beginning to respond in a way that I wasn’t entirely comfortable with.

“You’ve had your fun,” I whispered to him, trying my best to sound bored. “You’ve proven that you can overpower me. Congratulations. Now let me go, you’re just going to get bored with this anyway.”

“I agree,” he whispered back. “In fact, I think I’m bored with fucking your ass with just two fingers already.”

Removing his fingers, he squirted more lotion onto my ass. With no further warning he forced three fingers back into me. I grunted in pain, feeling my asshole stretching to its limits in order to accommodate him. Again, though, he ignored my pain and began pumping the fingers in and out.

As he continued his assault, I forced myself to remain silent, not wanting to give him the satisfaction of knowing that he was hurting me. At first it was difficult, but as time passed my body began to relax and the pain faded away. To my disgust, though, it was replaced with a feeling of bizarre pleasure.

Before that night, I had never experimented with anal sex in any way — nor had I wanted to. I considered it to be filthy, degrading, and disrespectful; definitely not something that I wanted to try. The problem was that while I still felt it was disgusting, I couldn’t deny that I was also enjoying it on a level that I didn’t think was at all appropriate. The fact that the pleasure was coming from a man whom I deeply resented wasn’t making it any easier for me to accept.

“Why does it seem like you’re trying not to moan?” he whispered into my ear. “You’re not enjoying this, are you?”

“Keep dreaming, faggot,” I hissed back.

“Ah, I forgot about the whole size queen thing,” he laughed. “You couldn’t possibly enjoy something as small as just three fingers. Let’s try four.”

“Rick, please no,” I cried, trying to keep my voice quiet enough so that only he could hear it while loud enough to convey my distress. “I can’t take four. I can barely take three. Please don’t.”

“Well, I don’t want to be a monster,” he whispered back. “Maybe we should try something smaller, instead. Possibly something that’s even smaller than one of my fingers, if you get my meaning…”

“Oh god, please no,” I whimpered. “Look, I meant that as a joke, and I’m sorry. I know you’re bigger than a finger. Forgive me?”

“Don’t be sorry,” he comforted. “It was a joke, and a funny one at that. But the thing is, the joke isn’t done yet; in fact it’s just getting started. Think of how hilarious it’s going to be getting fucked hard in the ass while having to pretend that I’m too small to notice!”

“Jesus Christ, Rick, you can’t do that!” I cried. “Look, I take it all back, but you can’t sodomize me in front of my friends. Please don’t do this, Rick, please? I’m fucking begging you!”

“Actually, I’m thinking that I won’t — you will. I’ll let you go, you’ll skewer yourself on my cock.”

“I’d never do that, you fucking pervert,” I said, doing my best to sound defiant.

“I think you will, actually,” he answered calmly. “But I don’t mind if you don’t. If you refuse, or try to run, or even if you just move too slowly I’ll simply pin you down and fuck you hard. Now, you might be worried that that would hurt, but relax. I promise it won’t hurt me at all.”

“Come on, Rick, you’ve proven that you can do this, now just let me go,” I tearfully begged. “I’m a virgin back there, I don’t think I can handle it — especially not with an audience. Please pick something else? I’ll do anything, Rick, I’ll suck your fucking cock, just please don’t fuck me in the ass? Please let me go?”

“I’d be happy to,” he responded. “All you have to do is surrender and admit that you’re infinitely weaker than me. I’ll let you go, you’ll never get your chance for revenge, but hey — at least you won’t look like a whore in front of your friends. I mean, they’ll still have seen you getting your asshole fingered right in front of them, so I guess they’ll still think of you as a whore, but you know.”

His words rang true. The damage was already done; there was no way that Kate would ever see me the same way again. I tried to push the humiliation out of my mind and focus on the idea that as long I didn’t give up, I could get my revenge on him later.

“Fine,” I hissed. “But don’t think I’m going to forget this. I will pay you back.”

“Whatever, bitch,” he laughed, releasing his grip.

I rose to my feet. Briefly considering running for it, I kicked my pants off just in case, figuring I’d have a better chance without them hanging around my ankles. Realizing that he probably wouldn’t hesitate to pin me down and make it hurt, I decided to accept my fate. Turning around so that I was facing him I straddled his lap. To my surprise, he pushed me off.

“I want you facing away from me, so they can get a better view,” he explained. “We wouldn’t want them getting bored, now would we?”

“Fine,” I grumbled. I was already in this deep, I couldn’t see anything else making the experience any more humiliating.

Turning away from him, I moved my feet apart and slowly began to sit down. Making the mistake of looking up, I noticed the expression on Kate and Jack’s faces. Kate looked utterly repulsed by my actions, Jack looked entirely too interested — neither of their facial expressions were exactly comforting.

Reaching between my legs I grabbed his shaft. Unfortunately, it was not in fact as small as his finger. Bracing myself for pain, I positioned it at my opening and slowly lowered myself down onto him.

As the head slid in, the pain was nearly unbearable. Reflexively, I tried to stand back up, but Rick grabbed me by the hips and would not let me. Though he didn’t force me down, he refused to let me back up. With no other choices, I pushed through the pain and lowered myself, impaling myself on his cock.

“I hope that you appreciate how merciful I’m being, bitch,” he growled. “I really ought to just slam you down hard; you’re moving entirely too slow. I suggest you fix that before my patience runs out and I make this hurt.”

Worried that he would make good on his threat, I clenched my jaw and forced myself down. The pain was incredible, but I knew that he could make it worse. Powering through it the pain, I eventually made it all the way down. In a screwed up way, I was kind of proud of the achievement.

“I hope you don’t think you’re done,” he warned. “I didn’t tell you to get my dick in you and just sit there, I told you to fuck it.”

“Rick, please cut me some slack,” I pleaded. “It hurts a lot, just give me a moment to regain my composure? I’ve already humiliated myself in front of Kate and Jack, isn’t that enough?”

With a hard slap to my ass he conveyed that it was not, in fact, enough. Remembering that I had persevered through everything he had thrown at me so far, I rose up a bit and brought myself down — slowly, but not without pain. Again, I attempted to rest, and again he brought that rest to an end with a slap to my ass. Repeating my earlier motion, I noticed that while it still hurt, the pain wasn’t quite as substantial. Not resting this time, I worked into a rhythmic motion, degrading myself for his sick enjoyment.

As I continued slowly bouncing on his cock, the pain again began to fade into pleasure. I began to increase my speed, fucking him harder and harder with each thrust. He seemed to appreciate that; instead of punishing me with another slap to the ass he reached around me and found my clit with his fingers. Applying pressure he rubbed my clit with more skill than I anticipated he would have. Between the stimulation to my clit and the surprisingly enjoyable anal sex, a grim realization dawned on me: if he kept this up, I would almost certainly cum.

“You’re not trying to repress your moans again, are you?” he chuckled. “Seems rather pointless, I don’t think you’re in any danger of being viewed as chaste in the near future.”

“Fuck you,” I replied. I wanted my voice to sound menacing, but failed miserably. I didn’t sound intimidating in the slightest; in fact, I sounded somewhere between lustful and pathetic. This was not helping my case.

“Hey, fair enough,” he offered. “You don’t have to moan if you don’t want to. In fact, please don’t moan — awkward silence can only help delay my orgasm, and I’d like this to last as long as possible.”

His reasoning was flimsy, but it was becoming impossible to pretend that I wasn’t enjoying his violation. Willing to take whatever excuse I could find, I told myself that I had to do this in order to get it over with and began moaning loudly. Kate cleared her throat to remind me that they were still there, but I didn’t care anymore. It was strange; though I had desperately wanted her to put an end to all this earlier, at that moment I just wanted her to shut up and keep out of it.

Rewarding my obedience, Rick intensified his assault on my clit. Overwhelmed by the stimulation, I felt an orgasm building quickly. I considered trying to hold off, but it seemed futile. Ignoring any sense of shame or decency, I let it happen.

To say it was intense would be an understatement — it was easily the most powerful orgasm of my life. Arching my back and forcing my head next to his, I pushed down hard. He never stopped rubbing my clit, which only drew the orgasm out longer. No longer interested in appearing reluctant, I loudly announced to everyone that I was cumming hard, crying out in pleasure.

As my orgasm eventually subsided, I found myself coming back down to Earth. Suddenly I was painfully aware of Kate’s disgust, Jack’s perverse voyeurism, and of course, Rick’s crude laughter. Overtaken by humiliation and shame, I lowered my head into my hands.

Rick, however, didn’t seem interested in showing me any mercy. Pushing me up and forward, I tumbled onto the floor, landing on my hands and knees. Before I could rise up to my feet Rick was on top of me, grabbing my hair and pinning me down. As I felt the tip of his cock rubbing up against my asshole, I braced myself for what I knew was about to happen. Without a shadow of gentleness, he thrust forward, again impaling me.

“Fuck that slut!” Jack cheered. “Give it to her hard!”

Jack’s words brought out strange feelings in me. As humiliating as it was to have a friend call me a slut and demand my abuse, the idea of being referred to as a slut was turning me on. I secretly hoped that he would continue cheering Rick on.

“Jack, what the fuck?” demanded Kate.

“Kate, you need to just chill the fuck out already,” Rick snapped. “Accept it, your friend Sara is a filthy fucking whore who loves being fucked in the ass while people watch. I’m not claiming she isn’t disgusting, I’m not saying that you shouldn’t be repulsed by her vile actions, but at this point I think you just need to accept reality. She fucking loves this, and your boyfriend seems to be enjoying it too. If you can’t participate, then you can at least shut the fuck up and stop trying to fuck up everyone else’s fun.”

My emotions were all over the place. A part of me wanted to stick up for my friend out of principle, but I just couldn’t bring myself to do so. As much as I liked Kate and hated Rick, I agreed with him. I didn’t like the fact that what he was saying was true, but I couldn’t deny that it was. Mostly, though, I just wanted her to shut up and let me enjoy my abuse.

“So Sara, how long have you been such a whore?” Jack asked cautiously, seemingly testing if Kate would object.

I pretended not to hear the question. I wanted to give Kate a chance to react, mostly just to see if she would. To my surprise, she held her tongue. I knew that I’d pay for it later, but I was okay with that.

“He asked you a question, bitch,” Rick growled, slapping my ass again.

“I’m not a whore!” I protested, trying my best to sound innocent and failing miserably.

“You’ve got to be kidding,” Rick laughed. “You’re getting hate-fucked in the ass by a man you claim to despise while your friends watch. You just very visibly came in front of an audience. ‘I’m not a whore’ might be a bit of a stretch.”

September 2018
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