Began in Anger, Ended in Shame

Story Info
He develops a crush that escalates out of control.
5.1k words
3.72
38.2k
11
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

People have always said that my temper would get me in trouble, but I never guessed how right they'd turn out to be. I'm usually a pretty nice guy, keeping my head down and trying to treat everyone with respect. When I get angry, however, my head clouds up and I don't think clearly. Fortunately, I can usually calm down with a little time alone and for many years it was never a problem.

That all changed in my second year of college with Allison. She transferred into my Chemistry class midway through the semester and I was immediately struck with how beautiful she was. Her almond skin, cute little round face, and silky black hair were incredibly alluring, but when I first saw her vibrant smile I was smitten.

It was clear that she was in need of a friend, so I volunteered to be her lab partner for the remainder of the year. She seemed to enjoy my company as much as I hers, with our study sessions containing as much playful teasing as actual studying. My thoughts at night danced with images of this girl for a couple of weeks before I could bear it no more.

It was a Friday night and I was hosting another "study session" at my apartment. After only an hour or so, we ditched the schoolwork and decided to watch a movie. Since I intended to watch her more than the T.V. screen anyway, I allowed Allison to pick the film; we ended up with some generic girly love story that she seemed to enjoy.

I snuck looks at her throughout the movie, studying the way her eyes lit up when she laughed. She was gorgeous, and she was just wearing a simple blouse and jeans. When I caught sight of her adorable "aww" at what must have been a particularly romantic part, I couldn't hold it in any longer. After the film ended, she commented on how great it was that we could watch those sorts of movies together. I agreed and then took my chance.

"Allison, I really enjoy spending time with you, and we make a great team. In fact, lately all I've been able to think about is our time together and how absolutely beautiful you are. All I want is to make this relationship into something more..."

I waited for her to absorb my words and react. The way her smile fell from her face and her expression morphed into one of pity was heartbreaking. I knew the answer before she said anything; my cheeks were already burning.

"Thanks, Thomas, but I'm not really ready for a relationship right now." She continued, explaining a recent bad breakup and her feelings towards me merely as a friend, but I couldn't concentrate on any of her words. My heartbreak from earlier was changing to rage and I could already feel myself losing control. Of course, I was a perfect gentleman about it and dropped the subject right there, but all I could think was "How dare she friendzone me?" I badly needed a chance to cool off.

To my dismay, Allison suggested watching one more movie before she left, perhaps out of pity. I couldn't think of an excuse not to that didn't increase my humiliation, so I dutifully started the film she suggested. It was clear neither of us were really watching it and I breathed a sigh of relief when she awkwardly got up to leave. She hesitated at the door.

"Uh, Thomas? It's awfully late and my house is pretty far; would you mind...?" I gulped down my humiliation and anger and got up to escort her home.

Neither of us really said anything as we walked. It was all I could do to keep my expression neutral. As we were walking through a deserted park, my foot caught in a crack in the pavement. I tumbled forward onto my hands and, like that, my self-control was gone.

"Are you okay?" Allison asked, reaching down to help me up. I accepted her hand and pulled down hard, eliciting a gasp of shock. Before she could regain her balance, I forcibly shoved her through nearby bushes, pulled myself to my feet, and threw myself after her.

As she struggled to stand in the grass on the other side, she managed one high-pitched yelp before I slapped a hand over her mouth. Her squirming was cut short when I produced a pocket knife, something I usually carry for self-protection. The irony of its current use was lost on me in my anger. She looked fearfully between me and the blade held to her throat.

"I've had it with girls like you," I began. "How dare you give me that shit about 'just being good friends?' I've been nothing but a gentleman to you, helping you with school and trying my best to treat you with respect, and this is my reward? If you won't respond to being treated like a lady, maybe you prefer being treated like a whore!"

I pushed her to the ground and reached for her blouse. She began protesting but was quickly hushed when I flashed the steel of the knife in front of her eyes. With her noises under control, I proceeded to remove her upper garments. With those gone, I simply had to remove her bra and I was left to admire her amazing tits. They were just the right size – her B cups suited her slim frame fine – and those little nipples were perfect. She usually wore loose-fitting clothes, leaving the shape of her breasts up to my imagination, but these were better than I ever dreamed. As she quietly moaned, I took each breast in my free hand and rubbed it, enjoying the feeling of her delicate skin. I then took one into my mouth and savored her taste, a combination of fear and her usual perfume.

Once I had had my fill, I began working on her jeans. She stared at me with absolute terror and I almost succumbed to those huge brown eyes, but my fury won out and I pulled her pants around her ankles, tossing them to the side. Now all that stood between me and my prize was one little lacy pair of pink panties. I cut through them with one swipe of the knife and feasted my eyes on her best parts.

There was her beautiful pussy. It was clean-shaven and an enticing pink – I couldn't resist rubbing her clit a few times. This made her moans louder and I was starting to worry that somebody would hear. Even in my rage, I had no desire to cause Allison any physical pain or to give her any injuries, and I was beginning to wonder what I'd do if my threats weren't enough to keep her quiet. Fortunately, when I pressed the flat slide of the knife hard into her thigh, she stopped gasping and allowed me to flip her onto her stomach and move to her excellent backside.

It was not uncommon for Allison to wear sweatpants to our study sessions, so her ass was what I most lusted after and I was not disappointed. It was extraordinarily round without a single blemish and the almond skin was perfectly smooth. I cupped one cheek in my hand and squeezed, relishing the plump curves. Spreading her ass apart, I viewed her little cherry asshole. It was so small and delicate that I couldn't resist leaning in and running my tongue across her entire ass, ending on her anal entrance. I felt Allison give a little uncontrollable shiver and knew it was almost time to move onto the main course.

First, though, there was something I had to take care of. I flipped her back onto her bottom and began reaching for my phone. She made a half-hearted attempt to get up, but I forced her back to the ground. With my phone in hand, I began taking pictures of all her perfect nakedness. I told I wouldn't hesitate showing her friends and family what a little slut she was if she ever said or tried anything, but only got a whimper in response.

With that taken care of, I unbuckled my own pants and finally withdrew my dick, which had been clamoring for release for some time now. Now, I've always considered myself fairly average-sized, but my member being barely a foot from her small face did it a lot of favors. She eyed it fearfully and made no move. Since she didn't seem to understand what came next, I grabbed her by the hair and yanked her face within inches of it. She wrinkled her nose and started squirming, but I cupped her cheeks and angled her to look right at my cock.

"You see this? You're going to pleasure it. If you do a good enough job, we can call it a night. Sound like a deal?" She nodded at first, then absorbed my words and began protesting again.

"Please Thomas, I'm a virgin—" she began, but was quickly silenced when I filled her mouth with my dick. I made sure not to go deeper than her throat, but the surprise entry meant she was still gagging and spluttering. I held my penis in that little bit of heaven for a few minutes, enjoying the feeling of her tongue frantically trying to find to avoid contact with my penis. Finally, I let her pull back and cough everywhere. There was drool and a bit of precum on her chin and her mascara had started running. Seeing my little angel in such a mess only made me hornier.

"That was good, but remember what I said about pleasuring me? I'll give you one more chance and this time I want some real effort." I pushed my cock back up to the entrance of her mouth and waited. She whimpered and obediently began to take in as much as she could

With her experimental attempts at pleasing me, it quickly became clear that that she'd never done something like this before. She ran her tongue over different parts of my shaft, testing my reaction and, though it was amateurish, it felt absolutely sublime all the same. The innocence with which she did it made me love her all the more and it took all my self-control to resist forcing her to deepthroat my cock. As horny as I was, I was still trying to treat her as delicately as possible and that seemed to be crossing the line. After several minutes I pulled out and allowed her to catch her breath.

"Now, I'm going to enter you one last time. When I release my load, I want you to swallow every last drop. Don't make a mess." She stared up at me with fear.

"Please don't make me swallow that," she mumbled, "I don't think I can take it." She sounded so pathetic that I considered.

"Well, I can be reasonable and listen to a lady's request." She looked relieved for a moment before I continued. "I'll let you decide, then. Do you want it inside or outside?"

"I...what?"

"My cum's either going down your threat or over your face. What'll it be?"

She looked close to tears for a few seconds as she considered.

"O-on my face."

"Alright then. I just want you to use your hands to finish the job. Go on."

She hesitated, but then reached for my dick.

"That's it, just give it a good rubbing and you can go home." Spurred by my promise, she began stroking the shaft.

"Like this?' she asked, looking up at me past the penis she grasped.

"That's perfect."

Encouraged, she worked faster. Soon, she was using both hands and pumping with a steady rhythm, determined to make me cum. The feeling of her delicate little palms wrapped around my dick was too much, and I knew I couldn't last much longer. When she got the idea to cup my balls with one hand, I could hold it in no more. With a grunt of satisfaction, I released my load.

Before she could react, it sprayed out across her face, covering it and her upper body. Her almond skin was sticky with cum and saliva, a large dollop covering one eye. She stared blankly at her hands, which had not yet released my cock.

When I backed away, she fell to the ground and simply laid there, defeated and covered in cum. I searched for my phone and, finding it, took more pictures of the scene. Satisfied, I kneeled down next to her.

"A deal's a deal," I said to her limp form, "You did an adequate job as a whore tonight, and I for my part kept your virginity intact. Just remember my warning." I held the phone up to her face.

Now, I completely intended to keep my word. Despite my rage, which had significantly dissipated after my orgasm, I still had feelings for this girl and didn't want to take things any further than I had. The way I saw it, I got a nice orgasm, leaving her no worse for wear. However, the events of the night played out much differently than I had anticipated.

---------

As I turned to leave, Allison still motionless behind me, I heard rustling in the nearby bushes. Before I could think to hide, a large figure stepped out into the moonlight.

It was a middle-aged man. He was large and intimidating looking, dressed in torn-up jeans and a biker jacket. I could see muscles ripple under the coat, even in the poor lighting. Allison and I stared at him blankly for a few seconds, trying to process his sudden appearance. Allison reacted first.

"Please sir, help me...he..." She was cut off by the stranger.

"There's no need to explain, miss," he said in a deep voice. "I saw most of the events of this night with my own eyes..."

I turned pale, images of myself in prison flashing before me. There was no way to deny anything, especially with Allison still covered in my cum.

"...and frankly, I'm disappointed. I wanted more."

We both stared at him in surprise for what seemed like an eternity.

"I'm getting old; it's not often I get to see the fucking of such a lovely little lady. But you gave it up too early. It needs to continue!"

Still we said nothing, too shocked to form any words.

"Maybe I wasn't clear." He reached into a coat pocket and withdrew a large pistol. The sight of the gun sent my heart plummeting and the knife fell from my fingers. "You're going to continue the night's activities, and this time I'll join you. I don't think I need to explain what will happen if we have any disagreements."

My rage from earlier had already died significantly after my orgasm and the sight of the pistol had dispelled it completely. I was filled with fear – fear of being convicted as a rapist, fear of this strange man with a gun, and, perhaps strangest of all, fear for the girl whom I had just finished having my way with moments ago. I really did care for Allison and never intended for her to get hurt, even in my darkest thoughts.

"W-what do you want us to do?" I stammered.

"Ah, getting the idea quickly I see! Well, I saw the way you teased this lady's lovely asshole earlier and the look you gave it. It's clear you want more; why not take some?" He gestured towards Allison.

She gave a little gasp and my heart did a somersault. He was talking about anal! It was something I'd wanted to do with my girlfriends, but they'd always been afraid. As much as I loved Allison's perfect little ass, I knew the pain was supposed to be enormous and so had avoided it tonight.

The man, gun in hand, grabbed Allison's upper arm and forced her into a position on all fours, ass stretched out. By this point her sobs were getting more frequent and more pitiful, but the man didn't seem to care. He beckoned me forward with the barrel of the pistol.

"What are you waiting for? She's going to need some lube. Use your mouth like you did before – make her asshole wetter so the entrance isn't so painful."

I hesitatingly obliged, getting down on my knees and bending forward to reach her anus. There it was, right in front of my face. Despite my terror, I found myself getting hard again. I couldn't resist the gentle curves of her ass cheeks and the inviting little hole – I leaned closer and jammed my tongue into her.

Allison let out a squeak of terror, but I could feel the cold steel of the gun pressed into my back and resumed my licking. I quickly ran my tongue all over the exterior of her anus, trying to get it as covered in spit as possible. I then began forcing my tongue down her asshole again, coating her insides with my saliva. I worked as quickly as I could but still couldn't resist enjoying the feeling of her smooth ass cheeks pressed against the ones on my face.

After a too-short amount of time, the man barked "That's enough! Time for the real thing." With some prodding from the gun, I was up straight again with my dick poised at Allison's asshole. I was terrified and excited, but then I saw her pathetic puppy-dog stare.

"I never meant for things to go this far," I whispered to her. "I'm so sorry, Allison." Before she could respond, the man kicked me in the leg, hard.

"Did I say you two could speak? Now, fuck her already!"

With no other option, I closed my eyes and pushed.

The feeling was incredible. Even coated in my saliva, Allison was still unbelievably tight. It felt like a boa constrictor had a hold on me. I groaned as I worked my dick deeper into her anus, inch by inch. Her whimpering soon turned to moans of pain or pleasure, I couldn't tell. All I could focus on was the incredible sensations running through my body and the sight of Allison slowly enveloping my penis.

After what felt like ages, I reached as deep as I could go. With a sigh of both relief and disappointment, I began pulling out.

The man had moved in front of Allison. "That's good, perfect," he said to me. "You keep doing that while I finish what you started earlier." He unzipped his pants to reveal his enormous cock right in front of Allison's face. He saw her eyes go wide with fear and smirked.

"Yeah, impressive, isn't it? Your friend with his little dong went easy on you, earlier, but now you're going to have to handle this big guy." He grabbed her by the back of her head and pulled her forward so that her nose was smashed against his cock. When she refused opening her mouth and tried shrinking away, the man slapped her across the cheek with the back of his hand, producing a resounding "smack!"

"You don't get a say in this, bitch! Now swallow it!" He forced her mouth open and immediately crammed in a good four inches. I had stopped pumping the moment he hit Alison and was now staring on in concern. He noticed this and snapped at me.

"Did I say you could stop? Keep fucking her!"

Though I was still worried, my body was all too happy to comply. I resumed my fucking, savoring the feeling of her anal walls, even while my guilt grew at my own pleasure. As I watched her miserably suck this man's dick, my body craved more and more. Unconsciously, I had sped up my thrusts.

It was clear that Allison was doing the best job of pleasing the man she could, because he wore a look of ecstasy. I watched as he forced her deeper and deeper, until he seemed to have reached the entrance to her throat. That was as far as I had gotten, but nothing seemed to stop him.

"I hope you're ready, sweetie." A moment later, he pushed further. Allison's eyes went wider than I thought possible, and she began making little spluttering sounds as more of the dick disappeared into her mouth.

"Get used to it; I'm far from finished with you." As tears streamed down Allison's cheeks, the man pushed deeper, deeper.

By this time I had gotten considerably faster and was nearing my edge. When Allison at last took the stranger's entire member into her throat, his pubes in her nose and her chin pressed into his balls, she clenched her ass so tightly that I thought my dick might fall off. The feeling was so incredible that I came immediately, the cum filling her asshole and oozing across my dick. I collapsed to the ground, exiting with an echoing "pop!"

The stranger wasn't done, though. He held Allison there, her face pressed into his groin, for well over a minute. Her struggles began to grow more and more frantic as she coughed into his balls and flailed her arms helplessly. When he showed no intention of releasing her, I got up in concern.

"That's enough! You're choking her!"

"You stay out of this!" he snarled. He managed to level the pistol at me with one hand as he kept Alison pressed against him with the other. By now she was using both hands on his legs to try to pry herself away, but his grip was too strong.

"And what is it to you if I hurt her, anyway?" he added. "Not twenty minutes ago it was you in this same position!"

I hung my head in shame. He was right; I was just as much a monster as him. I was totally helpless. Maybe I was feeling some small portion of what Allison was going through right now. All I could do was look on in disgrace as the man finally neared his end.

12