How Dungeons & Dragons Led to Me Fucking My Old Friend [M22/F23], [Geek][Bond][Torture]

Warning: Geeky, Role Playing, Torture. If at any point you become legitimately concerned, I’ve added some explanation at the bottom.

I’d considered not posting this one due to how obscenely nerdy it is, but a bunch of requests in another thread convinced me. I’ve never been much into role playing in the sack. It usually seems so absurd and almost comedic, but this one time it just seemed to flow pretty naturally. Even looking back on it though, it’s laughable.

This takes place before Rey, probably towards the later end of Bailey, possibly between the two entirely. Bailey and I had definitely been broken up for a while, but we kept a fwb thing going afterward. Regardless..

Like most desperate twenty somethings, I’d taken to doing just about anything I could think of to get laid. At the time, my sexuality was so horrendously out of control that anyone of the female gender seemed like a viable option. Enter Kelly. All of 5’3”, ridiculously petite, with a pixie cut and an english degree. [For the visual learners](https://s-media-cache-ak0.pinimg.com/236x/53/75/82/537582bf8c71fde2eada6f50557cde41.jpg)

Kelly and I had been friends at this point for over five years, and the whole time there had been this low heat attraction between us. We played D&D every week the entire time, as that was actually how we’d met. That is, up until a few months prior to this occasion.

See, we’d been roommates, Kelly, myself, and Kelly’s boyfriend, and it had been a less than stellar experience. Living with them had shown me just how much of an ass he was to her, constantly treating her like a child and a maid as if he was both her guardian and employer, while he was the literal living incarnation of Peter Griffin. Seeing someone that I cared about treated that way every day, day in and day out tore me up inside. As you might expect, I tried to be there for her, give her support, and feelings developed. One day, I decided that I would show her what it felt like to truly be cared about, to passionately and determinedly be made love to. Such was my naivete.

She courteously turned me down, although clearly with some hesitancy, and it was swept under the rug. A few months later, she broke down to her boyfriend and admitted that she’d kept it from him, he stormed home with eyes blazing, and I promptly left.

One of the lesser effects of my blowing up our friendship was that the D&D game was obviously destroyed as well.

Skip ahead six more months, and they’ve broken up. I have repeatedly apologized to both parties for any role that I played in that, but both have been upfront in saying that it wasn’t even a factor. They just weren’t compatible.

With them broken up and having not played D&D in a while I figured I would run a session for just her and I, as feelings between ex-bf and I were still pretty raw. In fairness, I hadn’t actually planned on getting laid. I had solidly learned my lesson to keep Kelly at arms length, and had really been jonesing for some RP.

So I showed up to her new apartment with a case of beer and some pizzas and we got right into it like old times. I won’t bore you with the gritty details leading up to the event, but suffice it to say she was playing a caravan guard transporting a few wagons through some woods inhabited by hostile elves. The caravan was ambushed, she was captured and taken to their dungeon.

I warned you.

This whole time, despite neither one of us intending for it to happen, there was clearly a vibe building. We hadn’t seen each other since the blow up, and I think we basically snapped right back to that moment when I asked her if she wanted to feel what it’s like to be cared about. There was that tension. We would reach for the same thing and accidentally touch, and it felt like a spark would run between our hands. When she asked to try my beer the knowledge that I was tasting her on the bottle thereafter gave me butterflies.

Role playing is mostly acting, and we get deep into the acting no matter what. I think that also gave us the freedom to excuse how we were behaving on the game as well. Things never got flirty, but they certainly got more intense.

“Your wrists are bound, you’re gagged, and a hood is thrown over your head,” I began setting up the scene. “After a walk so long you’re sure you wont be able to retrace your steps, you’re finally led, blind and disoriented, down some stone stairs. You’re shoved down as a few voices around you, mostly men, speak in a language you don’t understand. Bound as you are, you hit the ground hard, feeling a combination of flag stone bruising your hip and shoulder, and damp mud soaking into your cloths. Even through the haze of sweat and stale air building under the hood, you can smell the unmistakable scents of honey and fresh baked bread.

“Before you have a chance to reorient yourself, a large hand grabs the ropes binding your wrists and heaves you up. The hand brings your wrists high above your head, lifting you so that only the tips of your toes can touch the ground. The ropes are threaded through a large hook keeping you dangling.

“The hood is pulled from your head roughly, taking a few strands of hair with it and sending a shock through your scalp. You’re surprised to find that your eyes don’t really need to adjust to the dimly lit cell that you’re in. A few glowing crystals are placed in the wall on the other side of a set of bars in front of you, only just illuminating the small cell in a gentle yellow glow. You can safely assume that you’re underground now, as the ceiling and walls seem to be supported by tree roots rather than rafters and pillars. Naturally shaped stones line the walls and floor, only just giving the room a shape.

“Your gag is removed, and a man walks around in front of you. He’s at least a head taller than you, with a runner’s build. His face is less pointy than you’ve come to expect from elves, and his caramel colored hair is tied back in braids down his back. He’s wearing comfortable looking cloths, just a linen shirt, wool pants, and soft leather boots that go up to his knees. What concerns you though is his belt, or belts rather, which are bedecked with not just a half dozen knives and daggers, but bottles and bags of all sorts.”

“Do I think he may be a caster?” Kelly piped up stoically. Even sitting on the couch across from me, her back a was straight, her eyes were narrow, and her face was defiant. I noticed that she’d also placed her wrists together in her lap.

“Maybe. He’s certainly carrying a lot of options.”

Kelly lifted her chin arrogantly. “What happened to–”

“He slaps you hard across the face. Lights explode in your eyes and your entire body rocks on back and forth, dangling from the hook. You can definitely taste blood.”

“I spit at him.”

I put on a sneer. “You catch him above the eye, and he simply locks his gaze on you as a trail of blood slowly drips down his chin.” To emphasize the point, I loomed over the coffee table, putting my face only a foot away from hers and locking my furrowed gaze on her boldly defiant eyes. I spent a solid minute like that, examining her features as I imagined a captor would, looking for cracks in her mask, waiting for her to break character. I was intentionally unnerving. She was defiantly resolute.

At last, I stood up and turned away from her. “Do you know what we do to trespassers here?” I asked in something akin to an Elven / South African accent. I didn’t wait for a response. “We do whatever we want to them.” I began a slow pacing back and forth, pulling out my pocket knife and fingering the edge for effect.

“It does not matter why you are here,” I went on, “I do not care if you are a spy or a saboteur. It makes no difference. The truth is, I can do whatever I want to you and there is nothing that you can do to stop me. You can scream as loud as you like. No one will help you. You can fight me as much as you like, but eventually your body will break. You have come into my home, so now you are my property. And I will do to you whatever pleases me. And once I am done with you, I will throw you out into the mud and sell you, like the property you are.”

Now, the intent here had been to have a rough, character building torture scene with some wickedly sadistic elves, have her sold into slavery, have her fight in gladiator matches, and eventually go full Russell Crowe. When I turned to look at her though, I could feel the heat coming from her. I could see her visibly quivering at the thought of what was to come. I smiled inwardly and looked around the room.

“I feel like this’ll have more of an impact if we actually act it out.” I said, briefly breaking character. “What do you think?”

“Uh–” her voice faltered. She swallowed hard and shook her head. “Sure, yeah.”

I grabbed a coat rack and brought it to the center of the room. It towered over her small size and I promptly tied her wrists to the highest peg with a nearby scarf. “Good?”

“Good,” she nodded, looking anything but certain.

“Tell me if you want me to stop.”

She nodded again.

My hand flew to her chin, snapping us back into character. I grabbed her roughly, turning her this way and that with my face only inches from hers. My heart was racing now. So was hers. The energy between us was like lightning. I could feel her shaking under my touch.

“What is your name?” I sneered.

Her face was a resolute shield of rebellion, but her eyes were wild with fear. “Sylph,” she mumbled.

I slapped her hard across the face, holding the coat rack up as she wobbled.

“That doesn’t sound like a name for property.” I grabbed a fistful of her hair and forced her to look me in the eye. “I think your name will be Jezz. Now, tell me what your name is.”

“Fuck you!” she spat at me, this time actually hitting me in the cheek.

I chuckled villainously. “So eager. We have all of the time in the world.”

I circled around the rack, noting how she tracked me with her eyes, despite her best efforts not to be obvious. I took a minute to review what would have to be my impromptu tools, listing off both the fantasy and the sexual objects that I knew she had. Having been roommates with her, I’d stumbled onto a handful of each.

First I simply took off my belt. Still standing behind her, I folded it in half and trailed it up and down her back, her ass, and her thighs. The mask had fallen away. All I saw was fear in her eyes.

“What is your name?” I taunted.

With a shivering breath, she composed herself again. She fixed her gaze on the wall in front of her. I drew the belt away from her skin and watched her whole body tense as she braced for her punishment. I let the moment linger for just a second too long, then brought the belt down on her ass.

“Fuck!” she screamed, no acting necessary. Her whole body seized and shook from the impact. She tried to move away, but on her tip toes she had no traction.

“What is your name?” I asked again, calmly, as if this was routine.

“Fuck you! Fuck, fuck you!”

I brought the belt down again, this time slightly lower. She screamed incoherently. I had begun to worry that the game was going to far. Still in character, I strolled around and picked her head up by her chin. Her face was flushed and tears were just starting to roll down her cheeks.

“There’s no need for the pain. All you have to do is tell me your name and it all ends.”

She sneered with every ounce of scorn I think she’d ever felt in her life. “You will never break me.” She whispered through grit teeth.

It was a challenge. It was a challenge in character and out. Playful, yet deadly serious. She wanted to be pushed to her limit. So be it.

I arched an eyebrow. “No? But we’ve only just begun.”

Without warning, I reached down and pulled her shirt up. Her eyes went wide, but she didn’t protest. I shoved the front of the shirt into her mouth as a makeshift gag, then unclasped and pushed up her bra. The fear was back. I took a step back and traced her nipples with my belt.

“Are you so sure?” I whispered.

Again, her face scrunched up rebelliously, glaring daggers into my eyes.

I slapped her tits with the belt, catching one right on the nipple and one above. She screeched, now totally free to wreck her voice right into the gag. Again, she tried to get away, pointlessly swaying on the coat rack, visibly shaking.

While she swung, I undid her belt and ripped her jeans right down to her ankles, taking her panties with. I smiled when I felt how wet they were. As I circled behind her, I could even see the sheen of her juices on her upper thighs.

Again, I traced the belt up and down her abused flesh, tickling her with delicate touches that promised a world of pain. Again, I brought the belt down across her now exposed and red ass, and again she wailed and sobbed. She wept into the gag, and I laid the belt back across her ass, waiting until she’d just settled before smacking her again. And again. And again. And so it went. Sometimes the spankings would get lighter and lighter, to give the illusion that she was getting used to the pain. Then the odd one would be brutal, bringing on a whole new wave of excruciating pain. Sometimes she would tense when the belt left her skin, knowing it meant that inevitably it would return to bite her. Sometimes she just took it, screaming venomously all the while.

I noticed that she was now covered in a sheen of sweat, and took a second to admire how beautiful and helpless she looked. I felt wholly responsible for her, knowing that her well being was entirely in my hands right now. If she wanted, all she had to do was spit out her shirt, now completely soak with tears and spittle, and say the word. Any word. But she didn’t. She wanted to keep going. She wanted this.

I walked away for a minute, leaving her there, helpless and alone. I knew from past living situations that she kept her vibrating dildo in a drawer in the bathroom. In our apartment it had been “her drawer” with all of the various things that women need and men don’t want to be concerned with digging through. I’d stumbled on it by accident then, and figured it was placed there for ease of cleaning or something. As I’d suspected, she kept it in the same drawer here.

I came back into the front room, making sure to stay behind her to hide the toy, though her eyes had gone back to following me as best she could. I walked up behind her and grabbed a fistful of hair, forcing her to look away from me so as not to spoil the surprise.

“You know,” I whispered into her ear, “there are many ways to break someone. Pain is only one of them, the most obvious of them.”

I sucked the dildo into my mouth, still behind and out of site of her, coating it with a thick layer of spit.

“It’s not even my favorite way. Now degradation, to rob someone of their humanity and humiliate them to the point where they no longer want to be themselves… that is my favorite method.”

In one swift motion, I dropped her head and picked up one of her legs. I grinned seeing the strings of girl-juice connecting her pussy to her thighs now, and lined the vibrator up before brutally pushing it inside of her.

She thrashed and screamed, but still clenched down on the shirt with all of her might.

I let go of her leg, keeping the vibrator securely in place with one hand, and then grabbed her neck from behind with my other hand.

“Uh, uh.” I whispered, my voice laced with razors and threats. “Stay. Still. Stay perfectly still.” I flipped the vibrator on, feeling it hum in my palm and feeling her thighs quake around my wrist. “Keep this inside of you. I’m going to let go, and if it falls out, I will shove it up your ass.” I could see her eyes go wide from behind her. “Am I understood?”

She simply nodded.

I left the vibrator on a low-medium setting, something that I hoped would keep her on the edge but not push her over, and simply backed away.

Her thighs struggled to squeeze together with all of her strength. Suddenly her focus was no longer on me, but entirely dedicated to keeping the vibrator, the vibrator that her captor, her tormentor had shoved up her, inside of her most sacred of places. I had forced her to all but make herself cum for me. I wondered if she would stop me from fulfilling my threat.

Peering around while she was again distracted, I found a dagger on one of her book shelves. Kelly had worked a brief stint at a Renaissance Faire / Medievil Times themed place, and as such had easy access to all sorts of fantasy fair. Included in this was stage weapons.

I strolled over to the shelf and unsheathed the dagger. It looked like something a street rat would carry. The blade was no more than five inches. I ran my thumb over the completely fake edge, and then gripped it as hard as I could to see if it would cut me. It didn’t, and I had a horrific plan for how to use this. For now though, I dropped it onto the bed nearby.

A muffled whimper caught my attention. I turned to see Kelly wiggling anxiously on her tip toes, like someone was simultaneously tickling her and trying to brand her. Her eyes pleaded with me, a brief glimpse at Kelly’s emotions beneath Sylph’s character. Still, she bit down on the gag.

Then her eyes rolled back into her head, her hips thrust forward again and again, and her legs quivered. In all of the movement, the vibrator slipped out, leaving a thick trail of her cum down her thighs.

Her eyes snapped to mine. The realization completely cut off her orgasm. She began mumbling hysterically through the gag, shaking her head frantically. As I bent down to pick up the dildo, she even leaned her whole self as far away from me as possible, as if just grazing against my shirt would burn her.

I stood straight and glared into her eyes. They were pooling with tears. Her face was burning red and drenched in sweat, making her short cropped hair stick to her forehead.

“I gave you one simple order,” I whispered, dragging the goo-slick vibrator down the side of her face. She cowered and wilted. “I warned you. And yet you couldn’t perform one simple task.” I grabbed her face roughly, forcing her to meet my eyes. “What good is property that can’t perform a simple task? What possible use could it have?” I searched her eyes for an answer, drawing out the moment. “I’d hoped I might be able to sell you as a gladiator, but perhaps I’ll just sell you as a whore. Most likely to a mercenary or bandit group, who can tie you down to a table and take turns fucking all of your holes and filling you with their cum and then forgeting about you until it’s time to shove their poles up you again. No need for you to worry about taking orders, since you clearly can’t handle them.”

I let her head fall dismissively and circled around to her back. She immediately fought against the bonds, struggling with all of her might to get free, to move away, to turn her body away from me.

I’d had enough. I grabbed a fistful of her hair, hard, and pulled her head straight back so that she was staring at the ceiling. She screamed in pain and fear, and I lined the vibrator up with her quivering asshole.

“This is going to hurt so much more if you don’t stop fighting,” I whispered into her ear threateningly. She settled, still shaking like a leaf but at least not actively fighting me. “Good. Now, relax.” I began applying pressure. She squeaked. “Deep breath,” I coached.

I pressed the vibrator into her with constant, firm pressure, letting her body adjust and take it in at her own pace. Minutes passed, but so did the inches. Kelly whimpered the whole time, quiet, miserable grunts and gasps. Tears rolled gently down her cheeks.

We both gasped when it bottomed out in her. “Good girl,” I breathed. She panted. Without warning, I turned the vibrator on high. She screamed in surprise.

I circled around in front of her and slapped her hard across the face before forcing her to look at me.

“Now, Jezz, I’m going to give you one chance to redeem yourself. Keep that toy in your ass, or I will shove it down your throat, am I understood?”

Again, Kelly’s fear shone through Sylph’s mask. There was a heady mixture of genuine terror, complete awe, and questioning the validity of my threat. I simply turned around, retrieving the dagger from the bed.

I contemplated if this was really something that I wanted to do. It was… extreme. Still, she could have ended all of this at any minute. She wanted to brutality. She wanted to be tortured. I closed my eyes, took a deep breath, and turned back to her, brandishing the dagger openly.

She hadn’t noticed, as her eyes were far off, lost in the intense vibrations violating her deepest reaches.

I dragged the flat of the blade down her cheek, ripping her back to the moment. There was a question in her eyes, which built to fear as I slowly dragged the tip of the dagger down her throat, between her breasts, over her stomach, and finally pressed the flat of the cold blade directly to her clit.

She gasped, panting in fear and, I would find out later, absolute arousal.

“You have no idea how much I can humiliate you, Jezz. No concept of the depths I can drag you to.”

With that, I knelt down. She began to thrash, knowing what was coming. “This will go much, much better for you if you cooperate,” I threatened as I struggled to open her legs. She squeaked pathetically but relented, knowing that a blade, even a completely blunt one, was right next to her most sensitive area.

“Good girl,” I whispered, now splitting her lips with the edge of the blade. I smiled at the coating that clung to it, and, looking up into her eyes, licked it off as if it were the blood of a slain foe.

“Now,” I said, lining up the blade with her opening. “stay very, very still.”

She screamed with all of her might as I pressed the tip of the dagger into her cunt, but she stayed still. Slowly, millimeter by millimeter, the blade pushed deeper into her dripping wet hole, a cold, sharp contrast to the bulk of the vibrator still whirling in her asshole on its highest setting.

When the hilt touched her lips, she stopped screaming and simply sobbed.

I stood up, one hand still holding the dagger in place, the other lifting her chin to look at me.

“If I were you,” I whispered, “I would do my very best not to cum. Who knows what damage that tight cunt rippling over a blade might do.

Tears streamed freely down her face, fear completely evident. Her whole upper body shook like it was being electrocuted, but with an enormous amount of effort she was able to keep her lower body completely still.

I grinned at the amount of effort it took, the sheer determination scribed on her face. I’d taken a willful, impertinent rebel and forced her to keep her body from betraying her by committing one of the most pleasurable things it can experience, from one of the most inhumane invasions imaginable. As the orgasm built inside of her, the fear and desire battled constantly on her face. I don’t think there was a second of acting anymore. She wasn’t Jezz or Sylph. She was just Kelly, strung up on her tip toes, being brutally tortured by her close friend.

I studied her reactions, and every time I thought she was getting close to cumming, I slapped her. Hard. I wanted to end the orgasm in its tracks. The first time, I slapped her right across the face hard enough to make her body sway. Then, glaring in disgust, I watched her build up again in under a minute and slapped one of her nipples. Then the other one.

The last time, I grabbed a handful of her hair and ripped her head back to stare into my eyes.

“Look at you. Worthless filth. You’re really going to cum from having your ass and cunt so violated? Even when you could end this just by saying your name? Tell me what your name is, slut!”

Even with a solid grip on her hair, her eyes rolled back into her head and her body began to shudder. At the last second I pulled the dagger from her. The shirt fell from her mouth. Her voice cracked as she screamed her orgasm to the entire building at the top of her lungs. It lasted at least ten solid seconds, her body seizing over and over, writhing in the air, her pussy gripping in vain at the recent emptiness and her ass spasming around the vibrator wiggling around inside of her.

Finally, she slumped forward, completely still but for the occasional aftershock. At last, she whispered horsely, “Jezz.”

Unspoken, we both knew that the scene was over. I kissed her sweat drenched forehead and whispered, “Good girl.”

******

This was a particularly brutal scene, and by far the most extreme thing I’ve done. Please rest assured, it was entirely consensual. I breezed over it in the text, but her shirt was literally only held up by her biting down on it. At any point, she could have simply voiced her concern. I absolutely would not have been comfortable doing this otherwise.

Afterward, I wrapped her in a blanket and held her, bringing her down. After maybe half an hour, she thanked me, and told me that she needed to prove to herself that she could do that. She also felt like there was some remnant of her that needed to reflect and overcome the abuse that she’d suffered from her ex in some kind of extreme way. It had been a very cleansing experience.

Edit: forgot to mention, Rey and I have recently opened up our relationship. It’s already having a positive impact on her sex drive, and offers me opportunities to vent some sexual frustration on the side. Hopefully that means more stories for you guys.

Source: reddit.com/r/gonewildstories/comments/4vw3cc/how_dungeons_dragons_led_to_me_fucking_my_old