Monsters Friends and Mistaes

"Thanks for the game, guys," I said to my kinky D&D group. "I'm muting my notifications and going to bed." I gave them a smile and began to pack up my dice. The video call was still connected, as it was customary for us to wait for our DM, Jake, to disconnect first, just in case he had any last-minute additions to the evening's events and we needed to take notes.

Jake looked off camera and nodded. "Yeah, good game all. Catch ya later." He disconnected from the voice chat, leaving me alone with Jill, Leon, and Chris.

"Claire, don't forget that we have that interview at city hall in the morning," Jill reminded me "10 AM, don't be late. You're always late." she added in a mutter as Leon laughed.

I pursed my lips and tilted my head. "It's not like the Mayor is going anywhere. He needs us, not the other way around."

Chris perked up at that, his dice clinked on the table as he leaned closer to his camera, a skeptical arch to his brow. "The mayor needs you? For what?"

"PR, dear brother. Stop being overprotective. He's made some bad choices and publicity has been awful."

He waved and clicked the call off. Right, he wasn't actually interested in anything that wasn't along the lines of "Jill and I are gonna take turns blowing and riding him until we get a city contract."

Leon interrupted me with that devilish grin of his. "You mean people actually care when you shut down a program to feed the hungry? Who knew!"

"Err... that's not what he needs PR for. This is a different issue. He's installed these 'standing' benches in the parks that people can lean against instead of a place to sit."

"Motherfucker has no soul, does he? Why are you two helping him? He's a piece of shit." Leon was not shy about sharing his feelings on such subjects.

Jill responded before I could. "We need clients, Leo. Unless you have some wealthy benefactors up your sleeve then Claire and I will have to take one for the team in order to keep this business afloat."

I rolled my eyes as Leon pursed his lips. Always the do-gooder with a chip on his shoulder when it came to social expectations. "Relax, Leon. It's just a meeting to see if we want to take on the case. I honestly don't know if we can spin this and I'm not going to take on an unsalvageable situation just for some money. Sorry Jill."

Jill shrugged, "Tomorrow's a new day, maybe you'll change your mind. 10 AM, don't be late!" She disconnected - three down, one to go.

I leaned forward and smiled at Leon. "We could hang around a bit to see if my overbearing twin pops back in."

He laughed. "Why do you play so hard into that? You aren't selling anyone on you being siblings, let alone twins."

I grinned. "Come on, we have the same birthday and share the first names of the most iconic sibling duo in gaming history. How do I not play into that?"

"And he's as dark as you are light."

"Are you suggesting we cosplay as Cloak and Dagger?"

He sighed. "I would pay to see that. He's like two feet taller than you and outweighs you by at least a hundred and fifty pounds."

"One-seventy and two point four five feet taller than me. We checked. He's nearly three times my size and he's all solid-packed muscle."

"How did we become friends?" He asked in a flat, dry tone.

"We're friends strictly because of your name. I've spent years trying to collect the perfect set. We just need an Albert we can all hate--preferably a very rich one with a mild drug addiction."

"Seriously, how did we become friends?" He was smiling, though he was trying not to.

"You were friends with Chris, he introduced us, we hit it off better than expected."

His lips quirked again. "I recall you calling me multiple times after our game sessions."

"Accidentally! I was trying to hang up, not do a private call with some random guy I just met."

"Right. Accidentally, but multiple times." He leaned forward and playfully lifted his eyebrows. "If you wanted to hook up, you could've just said so."

I glared, but it quickly softened as his smug grin faded. "You have work in the morning, yeah?"

He nodded.

"Alright, goodnight then!" I said before clicking to cut off the call.

He had a habit of sticking around and chatting until the early hours of the morning if I let him. Sometimes a quick goodnight then hanging up was the only way to ensure our conversation didn't spiral into an hours-long debate on the meaning of a single word. Fun as I found those, we both needed sleep. I shut off my monitor and speakers then started getting ready for bed.

My jeans and T-shirt were exchanged for a snug white tank top and tiny pink shorts. I brushed my auburn hair and braided it into two long pigtails, then I did the whole nightly hygiene routine.

Though, before I could really fall asleep, I had a slight crisis to deal with. I was riding an adrenaline and arousal high from our game. Three hours of my character being teased mercilessly because I failed a seduction check on an orc. Of course, Jake's DM rebuttal of "The orc laughs heartily and rips your top off, 'No boobs. Too tiny. Try kobolds.' and you stand there with your A-cups being perked only by the cool breeze of the evening," didn't help.

No one would give me a shirt, we were nowhere near town and I had to fight with my boobs out three times. I laughed to no one as I recalled the worst part. Jake had grinned and I knew it was gonna be bad, but he was especially cruel. "The elven drider cocks his head to the side as he takes in your slender build and rose-colored areolae and nipples. Roll at disadvantage for... let's say acrobatics."

"Why disadvantage?" I'd asked.

"Because your tits are out and you're very aware of how many sets of spider or spider-like eyes are staring at them."

I'd failed my roll, of course, and the drider fondled my breast with his hairy tarantula leg and pulled me to him before cutting through my leather pants. I was blushing hard at that point, and insanely turned on. The sensation of a slightly fuzzy leg gently brushing down my body was a little too vivid for my liking in front of the group.

I'm pretty sure they ended the game thinking I was into monster fucking, and while I can say it's not a fetish for me, it kinda is my kink and I wouldn't turn down a partner wanting to do some drider role play. The size difference was alluring, as was all of the potential penetrative appendages.

I was preoccupied with the idea as I went back into my bedroom and turned my monitor back on. I checked my speakers again to make sure they were still turned off, then glanced at the door. My housemate was asleep and I wanted to keep it that way as I began to look up some clips.

I searched through images of driders with elven captives. It was certainly enlightening and I began to wonder what pedipalps would feel like spreading me open for a decidedly skilled elven tongue to explore me. I wasn't opposed to the idea, but I also shivered at the idea. Is scaroused a thing? It applied, as I was both scared and aroused by the thought of such an assault on my innocent pale pinkish body.

I waited to see if I'd be smited for that thought, but when no lightning bolt struck, I smiled.

Yeah. Totally innocent naked, vulnerable twenty-two year old body.

I found a story about a young tiefling stumbling into the lair of a drider king, and becoming his willing slave after he stripped her, bent her over his lap, then spanked her for the intrusion. He found that she got wet from being laid over two of his legs as his hand made firm contact with her lavender ass. He fingered her to orgasm then, while her pussy contracted against her will, he lifted her to his mouth and teased more from her.

It was quite hot to read her inner thoughts on why she shouldn't be allowing this drider to do such things to her suddenly needy body, but it just felt so good she didn't want to stop. It ended with her smiling and delirious from pleasure with a chain clasped around her neck. She was kept naked and displayed at his side, her pussy dripping and ready to be taken at the drider king's whim.

Reading wasn't helping. Fascinating as it was, no relief was in sight. If anything, I was working myself up more and more. My pussy refused to let me get over the edge and I was near tears with need. The drider thoughts, though... I could work with those.

I even jumped back into video chat on our server for a bit to see if anyone else would pop back on, maybe do a quick role play together so I could get off and sleep. I set my status to

Needy. Come play, please.

It was usually Jake who noticed when I came back around. And good DM that he is, he always had something ready to excite me with. And I always got off after.

While I waited, I looked around the web again. Lots of horny monster fucker fans are also superb artists. The trouble was finding one that suited my interests while hoping they had a whole catalog to peruse. I was only finding single images and cursed my inability to draw.

My imagination would have to do.

I turned my monitor off, then turned around and climbed onto my bed. I hadn't gotten off to the story or the artwork, but they were still on my mind as I sat on my bed and wondered,

do I masturbate more or just try to sleep while painfully horny?

Arousal won out, I wouldn't be able to sleep with that ache gnawing at me. So, I reached over to my bedside table and opened the drawer. I generally preferred my own hand, but was struggling and knew my wand would make quick work of things, then I could go to sleep.

My thoughts turned deeply wicked quicker than expected as I glanced back over to my computer. Adult chats with anyone other than friends never seemed to work out for me. I think it lacked the tension of "Oh, but we're friends and we shouldn't cross this line!" Maybe that's why it worked with Jake. He and I grew up together and he really understood me and my needs, but he also wasn't at all into me--at least, I assumed he wasn't judging by the string of boyfriends he'd had over the years.

Jake and I had grown apart in recent years. He was engaged and I think his beloved was a little jealous of our sexy role plays, which was understandable on the surface. But they didn't play out any different than our battle role plays. Hell, he'd worked out stats for things like constitution of species specific pussy in relation to stretchability during more monstrous encounters, innocence of character was sometimes played with in contrast to a partner's ability to corrupt, and agility? Well, that was a key stat for some encounters.

I will admit that sometimes rolling the dice mid-fuck to see if I held on or got thrown off could sometimes interfere with the arousal. It was all in good fun, though sometimes I think the numbers got him more excited than anything physical we talked about.

Then there was Leon.

He was soft-spoken and gentle. Whenever we did one-on-one role plays, he struggled with the idea of dominance. When things got heavy, he always stopped and checked in with me. "Are you sure you're okay with this?"

I'd nod, my cheeks flushed with the intensity of the scene. "Definitely. I trust you completely, so just go for it."

His brow would furrow and then he'd continue.

I was attracted to him, but I couldn't tell how he felt about me. There were moments when the way he looked at me made it seem like he wanted to be something more, but then he'd take me to a work function and introduce me as his best friend. He was perplexing, yet, for the sake of our dynamic, part of me was glad we had never experimented outside of a few sexy role plays.

Still, there's something just a little naughty about testing the bonds of friendship through sensuality and longing. And in such a moment, here I was lying in my bed with Leon's lower body being replaced by that of a giant spider on my mind.

His dark hair, tanned skin, and lithe frame filled in the upper part of my drider fantasy. Long hair, though. Something I could get my hands in as the fantasy progressed. A needed adjustment from reality.

I spread out the towel I kept beside my bed--for reasons--then I plugged in the wand and turned it on. My smile was anticipatory as I watched the wand vibrate. The low hum was familiar and comforting. Mechanical assistants were the closest I'd been to sex in a while, sadly, but this would have to do as my options were limited by my much too low estimation of how quickly I burn through batteries. My shorts were thin, so I didn't bother to pull them down. I simply, and quite lazily, moved the padded head of the wand to my pussy and let the vibrations pass through the soft fabric as I lay back on my bed with my legs spread wide.

It felt good even on the lowest setting. I closed my eyes and let myself focus on the fantasy in my head. The slow build of pleasure made me rock my hips slightly as I bit my lip.

Drider Leon smiled as he pulled me to him with fuzzy legs wrapped behind me, then his hand grasped my wrists and pulled me up to him. The weight of my body pulling at my wrists would hurt, but in such a good way.

I dangled before him as his spidery legs removed my barely-there pajamas, brushing teasingly over my nipples and vulva. Outside of my fantasy, I had one hand beneath my top, caressing my breast as my hips rocked towards the wand. Then I sat up, wanting my positioning to better match my fantasy. My feet bent under me and my knees were opened wide. I moaned as the vibrations went deeper this way, the weight of my body, slight as it was, pushed down against the wand in my hand, which was somewhat supported by the bed.

My whimpers were light and airy, my frustration built alongside my pleasure but I found the vibrations were not direct enough through my clothes, thin as they were.

I put the wand down for a moment and pulled my top off. The cool air of my room teased across my breasts and my nipples stood erect atop the small swell. My hand slid over them, then down my stomach and into my shorts. My fingers didn't vibrate, but I could feel the slick fluid coating me and soaking into my shorts. God damn, I needed a good fuck. Such a waste.

I worked my shorts down my thighs and began to stroke my clit. Then I lay back on the bed and kicked my shorts the rest of the way off. My legs were spread and my feet were planted firmly on the bedspread at either side of the towel.

What I wouldn't give for a nice big cock right now. On my knees, ass up, ready, willing, waiting...

My whimper was soft and I reached down, reluctantly removing my hand from my body, and grabbed the wand. I pressed it lightly between my labia. The padded tip became slick with my fluid and I slowly moved it up to my clit.

I arched my back and brought my hand beneath my thigh, opening myself up more to roughly push two fingers into me. With my other hand, I circled my clit with the wand.

Fingers aren't enough. So frustrating.

My body tensed and squeezed tight on my fingers. It wasn't an orgasm, but it was getting close to being one. My thumb pressed the upper button on the wand and the speed of vibrations increased. My hips lifted from the bed in response to my increasing arousal.

In my fantasy, it was my Leon drider vibrating his tongue gently back and forth over my clit as the rounded tip of his soft, fuzzy leg penetrated me with such care, lightly stretching me. And I was almost there. Just on the cusp.

My phone rang and I almost stopped to throw it across the room. Instead, I ignored it and pushed the upper button again. My fingers pulled out of me and gripped the bedspread as I cried out in pleasure. Choked as it was in my restraint to avoid waking my housemate, I didn't get the full relief of release and I was so fucking mad about it.

I needed the full experience--to scream my pleasure without restriction--but I couldn't. I reached blindly over to my bedside table until my fingers traced across something soft and rubbery. I pulled it out and smiled as I looked it over.

I sat the wand on a pillow, then straddled it just right for the wand to continue exciting me. My hips rolled and back arched as I brought the ball gag up to my mouth. I opened wide and bit down onto the ball before securing the strap behind my head. My gyration didn't slow as I maneuvered. The gag muffled me enough to groan loudly in pleasure. Both of my hands slid over my body and paid significant attention to my nipples. Pinching and twisting them as I threw my head back and cried out loudly.

Drool dripped from the gag and down onto my nipple. I closed my eyes to resume imagining my intrusive drider fantasy. He was behind me, his legs holding me as he kissed my neck and his fingers penetrated me.

God yes...

I moaned Leon's name as I rode the wand and the pillow. It was muffled and distorted behind the gag. Then I thought about Chris and Jake helping him.

Oh, my, yes!

My very human image of Jake grabbed my leg and held me up as the elven version of Chris did the same on the other side. They held me open to drider Leon as he positioned himself over me. I whimpered and cried out. I didn't know what a drider actually did reproductively, but this one had a dick much too large for a human, dripping with precum and pulsing with need.

I squirmed in their grip, my arms around their waists as I waited for the moment of connection. My phone rang again and I grumbled as I opened my eyes and looked over at it. It was face up and Leon's name and photo was on the screen. I leaned over and grabbed it then flipped it over.

Do not disturb, asshole. Busy with...

Yes, the drider dick was threatening my petite body and I was positively dripping at the notion. He was gentle as he guided himself into me. The ache of being filled made me shudder. Or maybe it was the wand doing that. I was panting hard and drooling heavily as I slumped over.

I wasn't getting relief on the pillow so I abandoned the teasing of my breasts to reach over into the drawer again. I pulled out the last two items. A small silver conical butt plug and a bottle of lube. I took my time. Slowly worked the lubricant over and into my ass, then did the same with the metal object. It wasn't very big. I was fairly inexperienced with anal and hadn't gotten the nerve to increase sizes yet, but that meant the plug slid in quickly and with little effort once sufficiently slick. Then I turned and leaned forward.

The wand was getting hot, my hand rubbing furiously, and I desperately needed to get off properly. My mind went back to my drider. Chris and Jake held me spread and Leon penetrated me. I shuddered and gasped as he pushed deeper. My toes curled and I lifted my hips to him.

It was too much, but I somehow wanted more. I brought the wand up to my clit as I knelt with my bejeweled ass in the air. I tightened and clenched in pleasure, and pushed the power up one more notch.

Then I screamed behind the ball gag. My body rippled in waves of pleasure and my toes curled as one knee lifted from the bed slightly, thigh trembling. My pussy clenched and a rush of fluid burst from me just before I collapsed in a heap on my bed. My hand barely had enough control to turn the wand off. I shakily unfastened the gag and let it fall from my mouth and onto the bed. My jaw ached from biting down on the hard rubber so fiercely. And I breathed deeply, trying to settle my body.

I laid there for what felt like a long time and was almost asleep when I heard a rustle. I opened my eyes to see my bedroom door was open. Then I looked around my room and saw Leon at my desk.

"What the fuck, Leon?" I shouted as I pulled my blanket over me. He had the monitor turned on, then moved so I could see. Jake and Chris were on camera and both had wide eyes and slack jaws, and then I noticed a few more avatars from our gaming group in the voice chat with my computer streaming live. I frowned. "What..." the thought trailed off unfinished.