I had known Allison for a long time. We went to high school together and she was one of the few people that I truly considered a friend. We were close, though our friendship had never progressed beyond the platonic level. Although there was mutual attraction there, we somehow managed to never both be single at the same time.
It wasn’t just the timing of our relationships that kept us romantically unconnected, though. Allison and I both have extremely competitive personalities, to the point that it’s probably unhealthy. We both habitually view all situations as contests in which we had to prove that we were the absolute best, even when doing so was unreasonable. I always suspected that if we took the next step we’d end up destroying each other just out of principle. Though I’ll never know for sure, I assumed that she felt the same way.
After graduation we fell out of touch with each other. We went to separate colleges, and without seeing each other almost every day our relationship deteriorated. We still talked from time to time for the first couple of years, but by the time we graduated we had completely drifted apart.
About a year after we graduated I ran into her at the post office. I barely recognized her – it had been about four years since we had last seen each other and she had changed. Just the same, I knew that it was her.
I hate to be the stereotypical male, but my first thought when seeing her was exclusively sexual. Allison didn’t just look good, she looked utterly fuckable – I deeply regretted the fact that we had never moved beyond “just friends”. I wasn’t sure if she was legitimately more attractive than the last time that we had spent time together or if when we were friends I had just somehow blocked out how hot she looked, but I immediately wanted her.
I walked up to her and said hello. I was strangely nervous – I’m rarely uncomfortable approaching people, but the fact that we had a history made me feel awkward. She recognized me once I got close and looked like she was feeling just as awkward as I was. It was nice to know that I wasn’t the only one who was feeling uneasy, at least.
We made small talk. It was weird. I think both of us felt a little guilty for drifting apart, but neither of us was about to say it. A part of me wanted to just drift away again – I felt really bad about letting our relationship die and was eager to make that feeling go away. I silenced that part of me, though. I missed her, and was willing to tolerate some awkwardness in order to get her back in my life.
It was a Friday afternoon and I didn’t really have anything to do that day, so I suggested that we hang out. She readily agreed – she apparently had no plans either. There was a public park right next to the post office, so we headed there, found a bench, and began catching up.
We discussed what had happened over the past few years of our respective lives and it eventually came out that she was single. This seemed almost remarkable – Allison had always had a habit of grabbing a new boyfriend as soon as she left her last one, she had rarely been single for any significant amount of time in all of the years that I had known her. By a fortunate coincidence, I was single at the time as well.
“I think this is actually the first time since we’ve met that we’ve both been unattached at the same time,” I laughed. “It’s like the universe is telling us something.”
I hadn’t meant to sound as if I was hitting on her, but I realized that it had come out that way. I’m generally much more straightforward; I don’t typically resort to bullshit lines about what the “universe” intends. I didn’t regret having said what I did – I wasn’t at all opposed to dating Allison – but I kind of wished that I had phrased it more aggressively.
“I think you’re right about it being the first time, Cliff,” she agreed. “Though, I’m not so sure the universe is trying to tell us anything. I like you, but you know how competitive I can be. I’d just end up destroying you, and then I’d feel bad about it.”
The way that she had phrased what she had said felt almost insulting. I felt like she was offering me charity; claiming that she was doing me a favor by keeping me out of the danger that would result in getting too close to her. Though I still wanted to be with her, her words had changed my immediate objective – I felt the need to prove to her that I was the threat to her, not the other way around. I didn’t need her protecting me.
“Trust me, I remember how competitive you are,” I replied. “I even remember how fragile your pride is – that’s why it doesn’t bother me in the slightest that you feel the need to pretend that you’d destroy me, as opposed to the other way around. I think that deep down, we both know that I’d make you my bitch – if pretending otherwise makes you feel better about yourself, I won’t stand in the way.”
“Bullshit,” she laughed. “I’m not some timid little girl, you’ll remember. I’d have you begging for mercy in no time.”
“Prove it,” I shrugged.
“How exactly do you expect me to prove that?” she replied. “The only way I can think of would be to make you my bitch, and again – I like you. I’d feel bad.”
“I’m sure I’ll survive,” I laughed. “Here’s what I’m proposing: I’ll consent to anything you can force on me, you do the same. First to beg for mercy loses.”
“Hardly seems fair,” she replied. “You’re like twice my size.”
“I am,” I agreed. “And I’m willing to make some allowances for that. Seeing as you can’t possibly stand up to me on an even playing field, tell me what handicaps I’ll need to accept for you to feel as though you have some chance. We’ll have two sets of rules – one for me, and a much more relaxed version for you that takes into account your physical weakness.”
I had chosen my words carefully. I knew that my size gave me an unfair advantage, but I didn’t feel like losing it. I suspected that Allison’s pride would prevent her from actually asking me to handicap myself, as doing so would be admitting that I was bigger and stronger than her. She was weird like that – even though my size advantage was blatantly obvious, she couldn’t bring herself to admit that she was inferior to me in any way.
“Fine,” she growled. “I don’t need your fucking charity; I can handle the same rules that you can. We have a deal.”
We shook hands and agreed to meet up again at her place later that night. I would have preferred meet up at my apartment – I didn’t like the idea of giving her the home field advantage – but I wasn’t going to press the issue. After exchanging contact information we went our separate ways.
I went home to get ready. I took a shower and put on some clean clothes, then relaxed on my couch. I was physically ready for her, but that wasn’t what mattered. Allison was an extremely intelligent woman, and I knew that she wouldn’t let everything come down to just a test of strength. I spent a couple hours analyzing how things might go in my head before it was time to leave.
I stopped by the store on the way to her place to pick up a case of beer. She had asked me to bring alcohol – I suspected it was because she wanted me drunk and off-balance, but I wasn’t about to refuse her request and appear weak. Tossing the beer in my trunk, I headed over to her place.
I parked my car in front of her apartment building and headed in. Allison buzzed me into the building and greeted me at the door. She had changed her clothes, but didn’t look like she had dressed up in any way. It seemed appropriate – we weren’t technically on a date or anything, and I hadn’t dressed up either.
I carried the beer into the kitchen area of Allison’s small studio apartment and loaded a few into the fridge. Grabbing two, I brought them back to her couch and took a seat next to her. It felt good spending time with her again. I was still looking forward to demonstrate that I was stronger than her, I wasn’t in any rush.
We spent the next couple of hours just catching up with each other. During the conversation she drank very slowly and frequently encouraged me to drink more. I knew what she was doing – she wanted me drunk enough that she would be able to overpower me. Catching on to her plan, I went out of my way to act far more intoxicated than I really was. I realized that I could have just attacked her right then, but it felt like that would be cheating. I wanted to let her make the first move so that she wouldn’t be able to claim that I had attacked her when she wasn’t ready.
By the time that I had finished my sixth beer Allison was barely halfway through her second. She was very obviously still sober, but I was beginning to feel pretty drunk. I had been intentionally slurring my words since my third beer, but the slur was becoming less and less artificial. I wasn’t so drunk that I thought she might be able to take me, but I knew that I would be soon enough.
I got up and hit her bathroom. I made sure to stumble a bit on my way, hoping to convince her that I was losing my sense of balance. On the way back, I intentionally stumbled, tripped, and fell down right in front of the couch. I hoped that I wasn’t being too obvious, but I needed her to attack before I really was as drunk as I had been acting.
Fortunately, she took the bait. In a single fluid motion she pounced on top of me, dropping her knee painfully onto my back before I could get up. Gripping my wrist, she twisted it around my back and pinned it down. I was impressed – it turned out that Allison was much stronger than she had looked. The way she had me pinned down was actually quite painful.
“Just remember what I said in the park,” she gloated. “When you’re crying your little eyes out and begging for mercy, don’t forget that I specifically warned you that this would happen. Really, you have no one but yourself to blame for this.”
“Allison, please,” I laughed, doing my best to sound like I wasn’t in any pain at all. “You don’t really think that pinning me down while I’m drunk is going to somehow force me to surrender to you, do you? To be honest, your knee on my back feels kind of good – can you try to dig it in a little deeper?”
I doubt that she bought my act – she must have known that the position she was holding me in was tremendously painful. Just as I had requested, she dug her knee into my back hard while pulling up on my wrist. It hurt like hell – it took all of my willpower not to scream in pain.
“Is that better?” she taunted. “You can end this at any time, you know – just admit that you’re my bitch and beg for mercy, and I’ll let you go. Eventually, at least. I mean, there’s no point in making you my bitch if I can’t have some fun with you first.”
Allison continued to twist my arm further up my back. I knew that I couldn’t pretend that it didn’t hurt much longer; I had to take action. Bracing myself, I pulled back hard with my arm, wrestling it from her control. With both of my arms free, I twisted around so that I was lying on my back with her still on top of me. Allison fought me every second, but she wasn’t strong enough to actually stop me.
Lying on my back, I took a second to catch my breath. It turned out to be a mistake – while I was resting, Allison reached back and punched me in the face. I was a little shocked by the behavior – I didn’t think that she had it in her to attack me so outright. It also hurt, but it was manageable. Resisting the desire to let her know how much pain I was in, I grabbed her by her wrists and shoved her off of me.
With her weight no longer on top of me I quickly climbed up to my knees and grabbed her. Wrapping my arms around her, I squeezed hard – both to restrain her and in the hopes of hurting her back a little. She thrashed around violently and struggled as best as she could, but she simply wasn’t strong enough to free herself.
“So,” I laughed as I held her still, “when you mentioned that you would have some fun with me first, what exactly did you mean?”
“Fuck you,” she growled, still struggling against me.
“Poor Allison,” I joked. “If all you wanted to do was to fuck me, you should have just asked. You’re my friend and all – I’m not above throwing you a quick pity fuck.”
Allison didn’t care for my mockery at all. Letting out a guttural howl, she thrashed her head back and forth and tried with all of her might to get free. I knew I couldn’t just hold her like that forever – it was only a matter of time before she managed to wrestle her way out of my grip. I figured I could always grab her again, but I didn’t want her to have even the small victory of temporarily escaping my grasp.
Squeezing her tightly, I took a seat on the couch and pulled her body over my lap. Grabbing her wrist, I twisted her arm around her back and pinned it down; just as she had done to me earlier. She flailed at me with her free arm, but I was able to catch it and pin it down with her other wrist without any difficulty.
Being bent over my lap didn’t do anything to calm Allison down, but it did make her efforts noticeably less effective. I found I was able to restrain her arms with just a single hand, leaving me one hand free with which to do whatever I wanted. As she thrashed about I took full advantage of that freedom.
I considered slapping her around a bit, but decided not to. I was still in pain from her attacks, but I wasn’t angry with her. It was strange, but while I wanted to defeat her I didn’t necessarily want to hurt her in doing so – at least not physically. Holding her steady, I began to tenderly stroke her hair in the most dismissive way that I could.
“There, there,” I chided. “There’s no need to freak out, little girl, you’re just having a little temper tantrum. Let all your silly little anger out; I’ll make sure that you don’t hurt yourself in doing so.”
My words did nothing to calm her down, but they weren’t intended to anyway. Enraged by my dismissive, condescending attitude she wrenched her body back and forth, trying in vain to get free. I knew she’d run out of steam eventually, all I had to do was wait her out. Holding her steady, I simply laughed as she struggled her energy away.
It took a minute or so, but Allison eventually managed to exhaust herself. Completely out of breath, she gasped for air while lying flat across my lap. I was impressed that she had managed to go on for as long as she did, and a part of me missed it. Reaching my free hand underneath her waist I unbuttoned her jeans and pulled the zipper down, hoping to inspire further resistance. To my surprise, rather than resist she simply laid there.
“You’re not honestly giving up so easily?” I asked. “I mean, I knew you’d give up eventually, but this is just pathetic. I’m curious, though. Is it that you know you don’t have a chance in hell against me, or are you just feeling slutty and eager to get out of those pants?”
Allison renewed her struggle, but it just wasn’t the same. It felt like she was only fighting me to prove that she wasn’t yet beaten, as opposed to legitimately trying to free herself. She was clearly exhausted – if I wanted her to actually put up I fight I realized that I was going to have to do more than verbally insult her.
Grabbing her pants by the waistline I pulled them down to her knees. She kicked her legs to make it difficult, but she didn’t manage to stop me. Looking down at her ass I considered pulling her panties down as well, but decided to leave them up for the time being. I wasn’t in a rush.
It was strange staring at her ass. Having been her platonic friend for years I think I had managed to convince myself that she wasn’t really a woman. Ogling her body, I couldn’t understand how I had managed to ignore how attractive she was. Just looking at her I could feel myself growing hard. I wanted to fuck her, but I didn’t feel like I could do that until I had defeated her. I wanted her to beg for mercy, only then would I reward myself with sex.
Gripping her wrists tightly with my right hand, I slapped her ass hard with my left hand. It did the trick in terms of renewing Allison’s struggles – she tried desperately to free her arms so that she could protect herself. Unfortunately for her, I realized that she’d try that and I was able to hold her steady.
“I’m really sorry to have to do this,” I lied, “but if you aren’t punished when you throw your temper tantrums you’ll never learn just how unacceptable they really are. I know that the spanking hurts you, but it’s the only way that you’ll ever learn.”
“Is that what you’re doing?” she growled. “I barely felt a thing – I just assumed that I left a window open and that was a gentle breeze I was feeling across my ass.”
I knew that she was full of shit but I didn’t see any reason to argue with her. If she wanted to pretend that I wasn’t hurting her I was fine with that – I’d just see how long she could keep up the act. Reaching back, I brought my hand down across her ass as hard as I could. She quietly yelped in pain but quickly restrained herself. Entertained by her futile attempts to hide any show of pain I continued to spank her hard for another minute. She clenched her jaw tightly as tears began to run down her face, but she didn’t cry out in pain.
“I’d like you to apologize for your little temper tantrum earlier,” I explained. “Tell me that you know that what you did was wrong – only then will I know that you’ve been punished enough.”
“You must be dreaming,” she sneered. “I didn’t even notice that you were punishing me; there’s no way I’m apologizing.”
She was obviously lying, but I respected her tenacity. By that point her ass was bright red with my handprints; she must have been in significant pain despite the way that she was acting. I knew that she wouldn’t be able to take it much longer, but I didn’t want to defeat her just yet. It felt too soon, and I had only hurt her physically. I wanted to humiliate her a little as well.
Grabbing her panties, I pulled them down to her knees. She winced in pain a little as my hand brushed over the bruised skin on her ass, but otherwise didn’t resist. Holding her steady, I basked in her fear for a few moments. She had no idea what I was about to do, and I wanted to savor that anticipation.
Something about her tone of voice made me suspect that she was just as turned on as I was. Feeling bold, I forced my hand between her thighs. She attempted to clench her thighs shut to block me, but quickly relented when I playfully slapped her ass. With her thighs slightly parted, I wormed a finger between them.
Her cunt confirmed my suspicions – she was dripping wet. I rubbed her clit for a few seconds, enjoying the look of shame and lust on her face. Gripping her wrists tightly, I slipped a finger inside of her and began to slowly pump it in and out.
“You fucking pervert,” she growled, trying too hard to sound as if she wasn’t enjoying what I was doing. “I knew you’d give up before you broke me. What’s the matter, hand getting sore or just can’t hold yourself back from pussy?”
“My hand is just fine,” I replied as I demonstrated by giving her ass another quick slap before slipping it back between her legs. “And I’d be careful tossing around words like
pervert - especially with a cunt that wet. Christ, slut – I think you’re making a puddle on my lap.”
“You’re one to talk, you fucking hypocrite,” she shot back. “Don’t think I can’t feel your dick pressing up against me.”
“What you feel is irrelevant,” I shrugged. “Still, you apparently don’t want my finger up your slimy little fuck hole, and it would be wrong for me to disregard your feelings. In that sense I have some good news for you: I’m only finger fucking you to get my finger nice and slippery.”
Before Allison could figure out what I was saying I pulled my finger out of her twat and forced it between her butt cheeks. She clenched her cheeks together, but she was entirely too slow – by the time she had reacted my finger was already sliding into her asshole. As I pressed my finger deeper inside of her Allison lost her and groaned loudly in humiliation.
“If you can’t handle this, you can tell me to stop at any point,” I reminded her. “You know that you’re going to bitch out eventually, so you may as well just get it over with.”
“Keep dreaming,” she growled. “I can handle anything your pathetic ass could possibly throw at me. In fact, if this is the best that you’ve got you may as well just give up now.”
The way that her face went bright red in shame told me that she wasn’t handling her anal violation nearly as well as she would have liked me to believe. I didn’t think that I could force her to submit through fingering her ass alone, but I didn’t really care. I had control over the situation and I wasn’t in a rush. Enjoying her obvious humiliation, I began to pump my finger in and out of her ass.
Allison did her best to make things difficult for me by squeezing her ass cheeks together. It didn’t stop me, but it did slow me down a bit. I pretended that I didn’t even notice, knowing that she wouldn’t be able to flex her ass forever. Sure enough, after about ten seconds she relaxed; allowing me to finger her ass without difficulty.
As I continued to finger fuck her asshole it seemed like Allison was beginning to accept it. She relaxed a little, allowing me to go a bit faster. I took full advantage of that, but the humiliation didn’t seem to be there – at least not in the quantity that I wanted. It seemed like she had mostly come to terms with the fact that I was fingering her asshole, and while she was ashamed she was able to handle it. More troublingly, the way she was beginning to breathe implied that she was actually enjoying the violation.
After a minute or so it became painfully obvious that she really was enjoying it. She wasn’t struggling in the slightest, and I could hear her quietly moaning. A part of me was glad that she was having fun, but I wasn’t quite done with her yet. I removed my finger from her asshole and attempted to completely remove her pants and underwear. Unfortunately, I found it impossible to do with just one hand. Temporarily releasing her wrists, I used both hands to strip the clothing off of her.
Allison took advantage of the brief freedom of her arms. While I was distracted with pulling her pants off of her ankles, she spun around and punched me hard in the face. It hurt, but I was more surprised than anything else. The way that she had submitted to being anally fingered had led me to believe that she was done with actively fighting back. Clearly, I was mistaken.
Having delivered her punch, Allison quickly climbed off my lap and scurried back. Before she could get too far away, though, I reached forward and managed to grab her wrist. Realizing that she wouldn’t be able to run Allison lunged back at me, swinging her free hand wildly. She connected a handful of times, but the pain she was able to inflict wasn’t nearly enough to faze me.
Pulling her in close, I wrapped my arm around her body and held her tightly to restrain her. With my other arm, I grabbed her shirt by the hemline and pulled it over her head. After tearing it off, I simply held her as she tried her hardest to struggle free. It didn’t take long for her to run out of steam that time – she was clearly still exhausted from our struggle earlier.
I brought her back to the couch and took a seat. Pulling her over my body, I sat her on my lap facing away from me. Allison put up a token struggle, but was clearly too tired to continue fighting back. By that point she knew that she was beaten; she just didn’t want to admit it.
I took advantage of the fact that she was exhausted and out of breath and began exploring her body with my hands. Allison didn’t even make an effort to try to stop me; though I don’t know if it was because she was too tired or because she didn’t want me to stop. I didn’t really care what the cause was, though – Allison had an incredibly sexy body, and I was enjoying groping her.
Before long my right hand had found its way to her breasts and my left hand had found its way between her legs. Her cunt was somehow even wetter than it had been immediately after I had spanked her; she clearly enjoyed what I had been doing. I tweaked her nipples and massaged her breasts as I began to play with her clit. Not only did Allison not resist, she actually spread her legs wider to allow me access. As I continued to manipulate her sensitive flesh, Allison began to moan openly.
“Giving up so easily?” I laughed. “I’m surprised, Allison – I thought you were stronger than that.”
“Fuck you,” she moaned, her mind very obviously focused more on her libido than her competitive spirit. “I’m not giving up – I’m still in this.”
Regardless of what she said I knew that she was done fighting for the night. She was completely exhausted; she simply didn’t have the energy to represent any kind of challenge. I would have liked for her to have surrendered, but it was no longer my primary goal. Wrestling with Allison had been a huge turn-on, and at that point all I really wanted to do was to fuck her brains out.
I grabbed her body tightly and then spun around, throwing her down on the couch facing upwards. Grabbing her ankle, I hiked it up high into the air and forced my body between her legs. As Allison watched in eager anticipation, I pulled my pants down to my knees.
I was rock hard. I guided the tip of my cock into her dripping pussy, staring her in the eyes the entire time. She returned my stare with one of lust and defiance as I pressed forward, forcing myself into her. She moaned loudly in pleasure, but she gave me no reason to believe that she had been beaten.
“I’m going to be charitable,” I explained as I began to fuck her at a reasonable pace. “I think we both know that I’ve beaten your ass, but I’ll let you put off admitting it for now.”
“Fuck you,” she growled as I began to build up speed. “You didn’t beat me; I’m just not trying my hardest.”
“Is that so?” I laughed. “What’s that say about you then, slut? Are you so desperate for cock that you were willing to let me finger fuck your asshole?”
I don’t think Allison knew how to answer. She had to either admit that I was stronger, or act as if she was some depraved whore who wanted to get her asshole fingered. For a woman as prideful as she was, neither answer was exactly desirable. Rather than answer me verbally she simply glared at me.
Allison grabbed me by my shoulders and began thrusting her hips towards me, fucking me back. The look on her face said that she wasn’t going passive – I might have had the upper hand, but she hadn’t given up yet. I was impressed with her tenacity, but at that point it just seemed silly.
Reaching forward, I slapped her across the face. As she looked back at me in shock and lust, I forced her ankles over my shoulders and pinned her down; fucking her brutally hard. Unable to move in any serious way, Allison reluctantly accepted that I was in control. She still looked defiant, but I knew there was no doubt in her mind that I had won that round.
I continued to fuck Allison as hard as I could for several more minutes. She never lost the look of resistance in her eyes, but she did begin moaning loudly. Eventually it became apparent that she was close to orgasm.
“You little whore,” I laughed. “It actually sounds like you’re about to cum. I guess that settles the question as to why you
let me win – you were just that desperate for my cock, weren’t you? I’m not mad, though – ask nicely, and I’ll let you cum.”
“Go fuck yourself,” she moaned back. “I’m not asking you for shit.”
I respected her for refusing my request, but I couldn’t just let it slide. I considered slapping her again, but decided not to – as much as I had enjoyed slapping her the last time, it seemed like she enjoyed it on some level as well. Placing my hands on her shoulders, I pinned her down and pulled out of her. She groaned in despair and struggled to get me back inside of her, but I managed to hold her steady. She clearly wasn’t happy about my stopping so abruptly, and I couldn’t blame her – I hated stopping just as much.
“All you have to do is ask nicely,” I reminded her as she struggled in vain. “I promise I won’t even gloat – at least, not too much.”
“Are you actually begging me to beg you?” she laughed back at me. “That’s just pathetic – I might want you to stop slacking off and get back to work, but I’m pretty sure that you want that too. All I have to do is wait you out; I’m betting that you’ll crack before I will.”
I wanted to argue with her, but I was pretty sure that she was right. My cock was screaming at me to put it back in, and though I suspected she was far more frustrated than she was letting on I knew that I couldn’t hold out much longer. Every second that I spent not fucking her felt like pure torture; I knew that I had to do something.
I flipped her over on her front and slapped her ass hard, causing her to yelp in pain. Sliding my arm underneath her waist I pulled her up to her knees, then grabbed her hair and pulled back hard. Kneeling down behind her I pressed my cock into her and thrust in hard. I didn’t feel good about giving up so easily, but I figured that I had beaten her enough for the night. Besides, she was right – there was no way that I would have been able to hold out longer than her, delaying the inevitable was just punishing myself.
It didn’t take long to get her back to the point where she was when I had left off. After less than a minute, she was clearly just about to cum. Reaching around her, I began rubbing her clit to push her over the edge.
It did the trick. As I rubbed her clit aggressively Allison arched her back and began to cum loudly. It might have just been my imagination, but it seemed like she sounded almost proud; as if she had won some kind of victory by achieving her orgasm. Not wanting her to forget that I was winning I slapped her ass hard, though it didn’t seem to do anything to reduce the pleasure that she was feeling.
Shortly after her orgasm ended mine began. I pulled out of her and yanked back hard on her hair, pulling her face to my crotch. Pumping my cock rapidly with my free hand, I let loose thick ropes of semen across her face. She clenched her mouth shut to prevent any from getting inside, but I didn’t care – in a way I was glad that I was cumming on her face instead of in her mouth. It felt like making her wear my cum was far more degrading.
“You didn’t break me,” she reminded me once my orgasm had ended. “I’m still very much in this, and I will have revenge.”
“I don’t doubt that you’ll try,” I laughed. “But I’ll be shocked if it goes down any differently than it did tonight.”