The owner of a nice home catches Margaret tagging his wall. Again. This time, there'd be consequences, and she'd be offered a chance for penance - or jail. Which one will she choose?
I'd repainted the wall running between my home and the alley three times this summer already. It was 10pm and I was taking some trash out when I heard the 'psssssst pssssst' of a spray can on the far side of the wall. Quietly I snuck out the far gate and made my way around the end of the block so that I approached the perp from behind.
Whomever it was, they were either really young, or a very petite girl. As I got closer I could make out the goth hair and clothes so I was pretty sure who I was dealing with.
When I was only a few feet away I said quietly, "Wow, nice work."
The painter jumped and spun around, eyes wide open.
"Don't worry, I'm not going to report you. Your art is just stunning."
"Uh.... thanks. I'm not used to, you know, being caught in the act."
"So where did you learn to paint like this? Do you have any formal training?"
We chatted for a bit about art, what she was painting and what other walls she'd tagged. She actually warmed up and started flirting with me. I smiled quietly, setting the trap.
"So," I said. "Could I get a picture of you with this? I write part time for a local paper and I'd love to do an article on street art in the area."
"Yes. I don't have my phone, but let me take one with yours and you can email it to me."
"Oh come on, it's YOUR phone. You can decide later if you want to pursue this."
"You're gonna give it back right? It's the newest iPhone and I just got it."
"Yes, of course."
She handed me her phone and I snapped a few pics of her in front of the wall and then walked over to the corner stone by my gate and smashed it against the corner, glass-first into the stone.
"Motherfucker! What the hell old man!?" She screamed at me, not believing what I'd just done. "Why the fuck did you do that?"
"Oh, I love the refractions that the shattered glass causes. Here, look at your picture now. See how crazy it looks?" I handed her trashed phone back to her.
"Goddam it, that thing was A THOUSAND FUCKING DOLLARS you stupid fuck! You've ruined it!"
"No, no, it's better now! Take another look. I love the way it is now."
"It's NOT YOUR FUCKING PHONE! You ruined it!"
I could see the tears and frustration welling up in her eyes. She'd probably been saving for this for a long time.
"So I don't have the right to modify your property without your consent? Was I wrong in doing that?"
"Fuck yeah you were!"
"So how long have you lived here?" I poked a thumb over my shoulder at the house.
"I don't live here, moron."
"So you don't own this wall you just painted?"
She stared at me with an utterly blank expression for a moment, then the realization hit her. "Ohhhh, you motherfucker," she hissed.
"Yeah, not so much fun now, huh?" I could see her seething, her anger just barely contained.
"You remember flirting with me earlier?"
"Yeah, so?" She pouted and folded her arms under her small breasts. Cocking her head to one side, I knew she knew how vulnerable she looked. It was completely intentional.
"How'd you like to make a thousand dollars tonight?"
"Oh, FUCK no! I know what you're asking. Ewwww! You're older than my DAD. And I'm gay, you idiot."
"Oh, ok. I totally understand. BTW, I did manage to email myself those pics I took. And the audio of you admitting to tagging walls all over the city. I'll just turn those over to the paper. It will make a great story. Sorry, but I don't know if they'll hand over their source to the police later. We shall see. Buh bye." I shuffled in my pocket for my keys and then shoved one into the lock.
"No wait! Uh..."
"You wouldn't hurt me, would you?"
"Hurt you like what?"
"I don't know, like torture or something." She toyed with her shoe in the dirt.
"Hurting women isn't my thing. And you can leave at any time. But if you leave before 8am our deal is off."
"Like, what would you do to me?"
"I don't know," I said, running my fingers along an imaginary beard. "You're gay, right? Then I might start with you cleaning this fucking wall. Or not."
"How do I know I can trust you?"
"You can't. So here's what you do. Take a video of you and me with our arms around each other, and send it to your best friend, saying that you met this guy and here's his address. Then say you'll call in the morning. If you don't, they'll know where you are and who you're with."
"You could still be a serial killer."
"You never even heard me approach you. If I had wanted to hurt you, you'd already be dead or tied up in the trunk of my car."
She contemplated her options for a moment. I could tell she'd been on the street for awhile. She was cold, hungry and filthy. Her survival instincts told her to run, but a good meal, a hot shower and clean clothes certainly sounded good.
"Look, come on in and take a look around. If you're hungry I have some leftover steak from lunch. You can take a shower, I'll wash your clothes and you can have a bite. It will be yor decision to stay or leave."
"What, do I smell?"
"Oh hell yes," I said, holding my nose, fanning my other hand and squinting like I'd gotten sprayed by a skunk.
"Nice. Nothing like making a girl feel special." She frowned, then cocked her head to one side and looked out from under her bangs with one eye. "What the fuck, I'll certainly get rid of your leftovers for you. Let's get that video sent to my friends."
I put my arm around her and we did a typical 'social media' pose and she said she'd met me and gave the address.
I opened the gate and ushered her through, locking it behind us. The walk wound around to the back of the house, a stone home from the 19th century. Inside it was thoroughly modern though. I led her through to the guest suite which was the size of a small home.
"Holy fuck dude, what do you to for a living? You don't have a place like this on a writer's pay." Her eyes took in the glass shower, tile floor and walls and monster jetted tub hungrily.
"Let's say I made some shrewd investments a long time ago."
"Damn, just - damn!" Her fingers ran through the material of the fluffy white robe hanging on the wall. "Ok, I think I need a long soak in this magnificent tub. Or do you call it a small pool? This thing is easily big enough for a party!" She cocked her head at me again.
"It has held a party or 20 in the past, but I'm sure you don't want to hear all the sordid details."
"Uh, ew. I'm fine and sorry for asking. I may be awhile."
"Take your time. It will take awhile to get your clothes clean. Draw your bath and toss your things into the bedroom. I'll run them through the wash while you're relaxing. Oh, there's a small wine chiller in the bottom drawer on the left. Help yourself to whatever you prefer."
"Really? Wow! Uh, where are the glasses?"
"They're in the chiller too, silly. Can't have a warm glass now, can we?"
"Ohhhh, of COURSE not," she wailed, throwing her head back with an arm across her eyes. "That SIMPLY WOULDN'T DOOOO!"
Not only was she pretty quick witted, she was funny as well. In spite of myself I found myself warming up to her. I had to remind myself that the point of this was to teach her a lesson.
I listened until the water stopped running and quietly retrieved her smelly pile of rags. There was no way I was going to run that shit through my washing machine. Opening the back door, I tossed them in the trash. Tomorrow we'd go shopping. If she made it! Otherwise she was welcome to take the robe which was considerably warmer than what she'd been wearing.
After quite a while I heard the bathroom door open and feet padding quietly up the hall towards me.
"Just to be clear, I still think you're an asshole. But damn, a girl could get used to this."
"Thank you. Oh, I forgot to tell you there's clothes in the bedroom closet that you're welcome to wear tonight. Let me go see if there is anything close to your size."
Walking back to the bathroom, I stuck my head in to see if she needed anything else. I noticed the now-used razor and shaving cream
sitting on the edge of the tub. I smiled, wondering what she was thinking about right now. Did she shave for me? Or just because she had the opportunity? I was pretty sure at some point I'd find out.
Returning to the living room, I found her sitting in one of the over-stuffed reading chairs, her legs folded up underneath her.
I took a seat on the couch across from her.
"There's a few things in there that might fit. You're welcome to take whatever you want."
"Thanks, but I think this is all I need for right now." She parted the robe, revealing one of my dress shirts. That was all she had on, and I got just a glimpse of her smooth inner thighs before she let the robe fall back closed.
"See anything you like?" She tilted her head at me and bit her lower lip.
Jesus, the girl knew how to be sexy. "I'm not entirely sure, but it may warrant some exploration later."
"Yeah yeah, right. Hey look. I know what's going to go down here tonight and I'm cool with it. Not my thing, but a deal is a deal. Why don't we just get the inevitable over with and I'll be on my way?"
"Ha! Uh, NOOOOOO." I said. "I haven't even decided if I'm going to take you there tonight, let alone what I'm going to do with you in the mean time. Either way you're mine until 8am."
"What, you're not going to fuck me?"
"I haven't decided if you're worth my time to fuck."
"You bastard! I'll have you know I'm very fuckable." She reached into her robe and twisted her nipples. I couldn't see her fingers, but it was obvious what she was doing.
"Whatever my dear. I normally only have sex with women who like guys. But if you play your cards right you may get lucky tonight."
"I bet you're all bark and no bite. You're probably a 'two-pump chump' in the sack." Her fingers slipped under the edges of her robe and gently pulled it apart until the edges fell away from her young body.
I could clearly see that she'd shaven, leaving just a thin landing strip of jet-black hair pointing to the promised land. Her stomach was flawlessly flat, with nary a bump, scrape or cut anywhere on her. I had to admit, it had been a long time since I'd seen such a mouth-watering example of womanhood. I tend to prefer women nearer my own age. While young women have beauty on their side, they rarely can keep me entertained emotionally and socially for very long. My last few girlfriends/fuck buddies were mature women with the bodies and battle scars that come from multiple children and sometimes husbands as well.
"Silly girl, have you even HAD sex with a man?"
"Yeah, I had a few boyfriends back in highschool before I 'switched teams'. Not sure what all the fuss was about. In, out, in, out, sleep."
"I should have been more specific. That was sex with a boy. Have you had sex with a man?"
"Well, the gym teacher at the highschool tried once, said he'd 'cure me' of the gay. But my boots were tougher than his testicles, so he was pretty un-interested after that."
"Hey, he deserved it. He was a pig. A were most of the boys I knew. Anyway, that's when I met Ann, and she pulled me to the dark side. I've been wearing that jersey ever since."
"Were you attracted to boys at all? Did you find some of them attractive in some way? Or were you just following along socially?"
"Yeah, there were some, early on that made my bits flutter," she said, glancing down between her legs.
I did too, noting that her labia were yawning open and there was definitely a sheen there, giving away her arousal.
"Like now?" I gazed directly into her eyes. She flushed red and looked away.
"Maybe." She refused to look at me and instead played with the hem of her robe.
"Does that bother you, that you're turned on by this?"
"Yeah, quite frankly. It does. I thought I was done with boys - or men - or penises or whatever."
"But there's still an inquisitive mind in there doing summersaults, right?"
"It isn't my mind that's doing flip-flops."
"I thought so." We sat there in silence for a bit.
Finally I got up. Tell you what, let's play a game or something. Do you shoot pool?"
"Yeah a bit," she said, almost stifling a smirk.
I had the sudden idea that she was a shark, and I was a baby seal.
I reached out to her and took her delicate hand and pulled her out of the chair and motioned her towards the stairwell. "There's a nice pool table in the rec room upstairs." I then proceeded to get the most spectacular view of her ass peeking out from under the edge of her robe. I'd intentionally ordered them short, and this was precisely why. She knew what was up and swung her hips seductively up the stairs.
"Whoa." The upstairs loft faced the mountains and the entire back wall was one giant piece of glass.
Flicking on the lights I walked behind the counter and grabbed some glasses and ice. "Bourbon? Whiskey? Tequila?"
"Uh huh," she said with a smile. "Yes please!"
I smiled back and poured us a couple shots which she chugged immediately.
"Dang gurl, you'd better slow down! I want you awake for later."
"Which is exactly why I want to get shit-faced and pass out. That way I won't have to put up with both minutes of wheezing thrusts."
"Wait, I thought I only had to stay on for the full 8 seconds?!?" I feigned astonishment.
She laughed, choked and spit the last of her shot all over the bar. Hacking and gagging, she doubled over the counter laughing.
"Ok, I'll give you that. That's funny." She raised her glass, I topped her off and we drank together.
I started the game, ran a few balls and then missed a shot intentionally to give her a turn. She picked up a few of my regulation cues, balancing them in her hands before ***********ing one. She ran it seductively through her hands while throwing her head back and moaning like a cheap porn star.
"Yeah yeah, let's see what you got."
She walked around the table eyeing her position and stopped directly in front of me, bending over to take a shot that was way harder than some of her other choices. She'd chosed this shot intentionally.
"Oh dear, I can't quite reach. I'll have to put one foot on the table." With that she hiked up her right leg and leaned way over the table until her chest was almost on the felt. Intentional or not, my weenie took full notice and immediately swelled to half mast.
"Here, you're not gonna make it like that." I walked up behind her and shoved my hardening member between her out-stretched thighs, landing cleanly inside her outer labia.
"Hey! Oh, hello! Oh my..." she exclaimed. She'd reached back around when she felt me against her, then gasped as my girth became apparent.
I reached down and dropped my shorts, pulling her back onto the top of my meat. I was pointed straight down but her lips moulded themselves to my base.
"Oh, by the way," I whispered in her ear. "I don't fuck strangers. So what's your name, little girl?" I pulled her hard against me and rocked my hips so my shaft slid wetly though her folds.
"Margaret. My name is Margaret."
"Oh, that's too bad," I said. "I don't fuck Margarets." I instantly backed away and pulled up my sweats.
"What the fuck dude? I splay myself all over your fucking pool table for you and and you decide you don't like my name? Why the hell does it matter?" She spun around and sat on the edge of the table. I know she was wetting down the felt, but I had cleaners for that sort of thing.
"My ex is Margaret and I hate that bitch, " I replied. "Tonight, you can be Olivia. I could totally fuck an Olivia."
"You are one weird old man." She got down off the table and walked over to me. "But I'm intrigued by what I felt." Her hands touched my face and she slowly turned her face up, obviously expecting to be kissed. I happily obliged.
Our lips and tongues danced for a bit as her hands roamed down my chest and around my waist. I felt like it was an inspection but I played along. Eventually she dropped to her knees and ran her fingers into the waistband of my sweats.
"So, I'm Olivia today. Who are you?" She looked up at me expectantly.
"Vlad? What kind of name is THAT?"
"You've not heard of 'Vlad The Impaler?'"
"Vlad the...oh, that's cute."
"Never, ever tell a guy his penis is 'cute'. You're about to understand the 'Impaler' part though."
Her hands felt my bulge, and she rubbed her cheek across the fabric in a most catlike fashion. I could almost feel the warmth of her breath against me and I slowly filled with blood, pushing back more and more against her cheek.
"My my, Mr. Happy seems to like my attention. Maybe I need to release him from his prison, yes?"
I knew she knew that I thought I was still in control. I was probably wrong. I realized this as she pulled my sweats down just enough to expose some of me and engulfed the tip of my meat with her mouth. "Mmmmmmm. I have to admit it's been a long time since I've done that!"
With that she wanked my sweats all the way down and was promptly smacked in the face.
"Holy. Fucking. Hell."
"What, still wondering why I asked if you'd had sex with a man instead of a boy?"
"There's no way you're sticking that thing in me."
"I can, and I will. But not until you beg me for it. Then, and only then will I put you out of your misery."
"Yeah, like I'm such a cock slut I'm going to beg you to fuck me. I don't think so."
"We will see."
"Really? It's not like I haven't had orgasms before. GOOD orgasms. I think you over-rate the importance of dick."
"And what is more important than dick?" I asked.
"Well a talented TONGUE for one."
"Like this one?" With that I reached down and scooped her up, throwing her onto the leather couch. In an instant I was on her and grabbed an ankle in each hand, pulling her legs far apart. With my grip I held her legs and most of her torso off the couch. The robe had flown up and was now covering her face so she couldn't see what I was doing. Which was slowly lowering my face towards her now soaking sex.
"Hey, what are you doing?"
My warm breath caressed her inner thighs as I approached my target. Her labia yawned open again revealing almost no inner lips at all. They met together in the tiniest of clits.
"Mmmmmmm," I breathed directly on her bringing a yip of excitement.
Sticking my tongue out as far as I could, I tasted her flesh for the first time just below her navel. Slowly expanding sweeps back and forth lowered me closer and closer until the very tip of my tongue dragged across her clitoral hood. At that moment I held perfectly still.
Olivia's breath was coming in short, shallow gasps and her hips swayed back and forth trying to get more contact.
"Don't you dare stop," she hissed. With that I circled her with agonizing slowness until she finally grunted and grabbed my head, pulling my face onto her aching flesh. I released an ankle and my left hand snaked under her. With a squeal of delight I sunk my thumb into her up to the first knuckle. Pulling her opening down tightened her lips around her clit and after a flurry of flicks she went over the edge into a massive orgasm.
"Fuuuuuuckkkk!" she screamed as she rammed herself up and down across my tongue. After a final shaking wave she collapsed in a heap.
"Ok, ok. I think I'm going to have to re-think my position on old dudes. I also have to seriously re-think my parent's relationship. They were always so happy and touchy-feely. Was it because dad was...Oh God, I can't think about that right now!"
She lay there for a few minutes, catching her breath. "So, big boy, how about that steak you told me about? Or is the only meat I'm going to get hanging between your legs?"
"'Sausage' and 'steak' are not the same thing. I do have steak and salad if you're hungry. "
"God, I'm FAMISHED! And a bit of good news for you - feeding me steak might increase my appetite for sausage. She threw me an exaggerated wink.
I had food and wine out in just a few minutes and she dove into the meal like it was her last. "OMGOD this is so good!"
"You might want to slow down. You know there's a good stuffing coming, right?" I winked back at her like she did to me earlier.
"And if this is Thanksgiving, you're the turkey, and you'd better pray if you're going to get any of my dessert!"
Now we were both laughing.
I watched her eat and drink until she was completely sated. Finally pushing her plate back, she sighed and said. "That is probably the best meal I've ever had. Whew!"
"Don't forget, you still have a sausage coming. So to speak..."
"Oh man, I'm not sure I can 'stomach' that right now. But I did want to inspect it again. How about we try out that marvelous shower in my bathroom?"
"Your bathroom? Aren't you getting a little ahead of yourself?"
"Kiss my ass!"
This time she took my hand and led me back up the stairs. We shed our clothes and stepped inside.
"Oh! The floor! It's WARM!"
"Yes dear, can't have cold tootsies."
Olivia rolled her eyes, then turned me around to face the wall and slowly lathered up my back and shoulders. After a while she worked her arms around me and soaped up my chest paying particular attention to my sensitive nipples. I was raging hard when her hands finally drifted down to my meat.
"Jesus, you're SO thick," she murmered. One hand stroked my length and the other slipped up through my legs to gently cup my balls.
"Oh dear. These are simply too full. We must give them some relief!" With that she started an exquisite combination of tugging and stroking that had me moaning in spite of myself. She may be gay, but she certainly understood foreplay and sensuality.
"Alright, time to turn around." I did and ended up with my tip just inches from her lips. She looked up at me and then slowly slid her mouth down over my tip. I moaned again involuntarily. As I stared directly into her eyes.
She withdrew her lips until they were just barely touching me and then wrapped her fingers around my balls and tugged, encouraging me to lean forward, impaling her face. I got barely half inside before her eyes shot open and she gagged, coughing and hacking for a minute.
"I gotta tell ya, I am feeling way more impressed by porn stars now. Holy Hell it's hard not to puke when you hit the back of my throat."
Olivia steeled her resolve and tried again. Over time she coated my cock, balls, thighs and ass with her saliva and she was eagerly letting me bounce off her tonsils. Slowly I was ramping up and she could sense it too, encouraging her to take more.
I knew I was getting close and ran m fingers through her hair in preparation of me holding her tightly and blasting my load down her throat whether she liked it or not.
She sensed what was about to happen and prepared for a massive load that she wouldn't be able to avoid.
What I didn't expect was one last great act of defiance on her part. She was going to take my load, but not without it being on her terms.
At the last second she jammed her middle finger deep into my ass and wiggled it as hard as she could against my aching prostrate.
My eyes shot open and I only got part of an "AHHHHH!" out before positively exploding in her mouth. Holding her tightly I jammed the remaining inches down her throat and unloaded. Holy fuck, I've never come so hard in my life! It just kept on rolling, and the finger in my ass kept pulsing against my prostate causing another round of contractions. Finally they subsided and I leaned back against the shower.
Olivia gasped and coughed, trying with all her might not to hurl all over both of us.
"You're a fucking asshole, just like I thought," she said between gags. "I thought you said you weren't going to hurt me?" She hung her head and let the water flow over her.
"I did. Are you hurt?"
"Well there you go then."
"I'll have you know I despise the taste of semen."
"Did you taste any?"
"No goddamnit, you fucking blasted that shit directly into my stomach!"
"So the problem was solved, right?"
"And what was with the finger in the ass?" I shook a finger at her and glared sternly.
"Oh come on, I knew what you were going to do. I thought I'd give you a little taste of 'unwanted' while we were at it. But come on, you fucking loved it. I have the calories to prove it! Jesus dude. You gotta get off more." She shook her head and the slightest smile spread across her face.
"Ok, point taken. I'd have felt bad if you'd drowned."
"If I'd DROWNED?!?" She slapped my thighs.
We eventually got out of the shower and crawled into bed. I rolled her on her side and pulled her tightly to me. "Just relax. You're safe tonight." We fell asleep in minutes.
Sometime during the night I awoke from a sexy dream to find Olivia backing her butt up against my lap, which was full of raging hard-on.
Her hands had something slippery on them, and they were between her legs but wrapped around me. The scent was of clean woman and lavender, which explained the slipperiness. I had a bottle of lavender lotion on my night stand that she'd discovered at some point.
She dragged my meat up and down her soaking slit, rubbing her clit in circles with every pass. She looked over her shoulder sternly.
"I have good news and bad news, 'Vlaaaaad', " she said, drawing out the 2nd syllable. "I am a girl with competitive instincts, and I want to see if I can make this thing fit. But this is MY quest. Based on your actions in the shower, if you try something like that I'll cut your balls off and keep them for a souvenir. You got that?"
"So, if I just lie still you'll fuck me until we both come?"
"Probably. Most likely. There's a good chance. Sort of."
Her hips started up again, rocking back and forth. Her fingers slid deliciously up and down my shaft as she guided my tip according to her whim. Eventually she let me center against her opening. Moment of truth. With the slightest push she held me in place and let her body expand to accommodate me. An inch slid in, then the bulbous head oozed past her tightness. She gripped me like a vise.
"Ugh! This is supposed to be fun?"
"Hang on dear, give your body a chance to adjust. Just relax and focus on another sensation."
"Yeah, like what?"
"How about this?" I snaked a finger between her legs and ever so gently dragged the full length of my finger across her clit.
"Uuuuugh, that feels amazing! Yes, that might help."
"OK, How about this?" My other fingers found a pouting nipple and gently rolled it back and forth."
"Oh! oh!" Yes, oh my God!"
"Then there's this." With that I dragged my lips across the back of he shoulder and up onto her neck. At the same time I tweaked her nipple and her back arched involuntarily, impaling her with another 3 or 4 inches.
"God Damn- fuck - that was a TRICK you motherfucker! You knew I'd arch my back!"
"I knew no such thing, and I did not break the spirit or our agreement. I have in fact not moved an inch."
"Well yeah, but..."
"Butt? You want it in the butt?"
"HELL NO! First of all, it would never fit. 2nd, that particular port is exit only, motherfucker. Don't try anything funny."
Another tweak and her back arched again. This time I wrapped one arm around her neck and the other across her stomach. My lips found the nape of her neck and I gently pulled her back towards me, oozing into her moulten sex.
"Oh! OH! OOOOHHHHMYGOD..." Her breaths were shallow and quick, almost panting. After a few seconds she thrust her ass back until her cheeks bottomed out against my pubes.
"Fuckfuckfuck. I can't tell if that hurts in a good or bad way. But fuck, it's amazing," she whispered. "I had no idea."
"A little different than the last time?"
"Uh, how about a BIG different?" With that she pulled away from me just a bit and then settled back against me again. "God, I don't know what you're hitting, but Jesus does that feel good!" Her pace back and forth increased just the tiniest bit as her body got used to my intrusion. Soon she was taking long, slow strokes and twisting her hips at the same time. Now it was my turn to have my eyes bug out.
I was pretty sure I wasn't going to last very long like this but figured I might as well get the first one out of the way. Louder and more frequent grunts should signal to her what was about to happen.
"I'm getting close! Are you ready?" I hissed in her ear. I renewed my vigor on her clit and nipple.
"Wait, no, I don't want you to..."
"What? You don't want me to what?"
"Come in me."
"Why not? I'm really really close here."
"Nonono! You can't! I'm not on birth control!"
"Well," I said, pulling out of her slowly. Pushing her away from me I crawled on top of her now prone form.
"Let's just see where else I can come then, ok?" With that I pushed myself down between her thighs and stroked up and down along her engorged labia. Soon Olivia was raising her hips off the bed, encouraging me to fuck her again.
On the next pull upwards I raised far enough for my cock to spring out from between her thighs and it settled down across the crack of her ass. Moving my hips ever so slightly sent shivers through both of us.
"Do you like that?" I asked, trying to steady my voice so she wouldn't see how close I was to losing control and painting her back with my sauce.
"Oh yeah, that feels so good," she whispered.
"Does it feel good here?" With that I tilted my hips and pushed just my tip against her opening.
"Yes, right there. Right there! With that she tried to impale herself by thrusting up against me. I lifted the same amount, frustrating her with every lift.
Finally I raised up and tilted my tip downwards so that with her next lift I hit her square in her tight puckered asshole.
"Woah, funny boy. Not gonna happen." She dropped her hips immediately.
"I'll bet you a thousand dollars that it will."
"Wait, what?" She asked with confusion in her voice.
I held her hips down and lowered myself until I was just touching her sphincter again.
"Hey, I was serious! No."
"Well that is too bad. We had a deal. You can go now."
"Go? WTF man! You think you can just decide to fuck me in the ass without my consent? No fucking way. I'm out of here."
"Well that is too bad. But I did enjoy the evening. Your clothes were so nasty I threw them out but you're welcome to keep the robe and slippers. They are significantly warmer than what you were wearing."
"So you're really going to let me walk? I've had fun, but this isn't worth a grand. Buh-bye." She got up and padded towards the door.
"You mean two grand," I said quietly.
"Yes, I said you'd get a thousand dollars if you stayed with me until 8am. You need a morning-after pill anyway. The other grand was for your ass. But I understand. Limits are limits."
"You'd really pay me a grand to stick it in my butt? You're pathetic. I thought you said you dated all these young and old women. Stick it in their butt."
"Ok, I will. Would you like to watch that? Look, the money is because YOU need it, not because I can't get laid. In fact, I think I'll call Leslie and have her over. I can fuck her anywhere I want. Bye bye." I reached for my phone.
beep-beep-beep, went my phone.
"Wait, goddamn it! I'm thinking. Would you stop dialing for a sec?"
"Better hurry." beep-beep...
"Fuck me, goddamn it. Ok. Ok. You win you fucking asshole. You want it now? Here? But I get the fucking money RIGHT NOW or you don't touch me again."
She was pissed, but that is where I wanted her.
I got up and went to the picture of a lovely lady standing waist deep in a lake and pulled one side out, revealing a safe. I typed in a combination, held my thumb to the pad and twisted the dial. I reached inside and pulled out a couple stacks from the pile, closed and locked the safe and swung the picture back against the wall.
"Here." I tossed the money on the bed. Her eyes widened and she dove back onto the mattress and thumbed through the bills.
"Ok." "But if you hurt me I'll kill you."
"Don't worry, you'll be begging me for it in a few minutes."
"I doubt that, but give it your best shot."
I grabbed her ankles and dragged her half off the bed, dropping her legs to the floor. In an instant I was balls deep in her pussy. Grabbing her hips I held myself all the way in.
"Fuck, dude! You gotta give a girl warning before you rip into her like that!"
"What fun would that be?" I flexed my cock repeatedly, rubbing my tip all over her insides.
I couldn't see her eyes, but I bet they were rolling up inside her head.
My strokes started long and slow, maximizing the rearranging I was doing to her guts.
"Uh, Uh, Uhhhhh," she groaned with every thrust. Her groans increased in intensity and tempo until the edge was almost within her reach.
So of course I pulled out and laid myself across her crack, holding perfectly still.
"You bastard! I'm so fucking close. Put it back in!"
"Really? You're close? To what?"
"To a huge orgasm, motherfucker! Is that what you wanted to hear? That you had my number? That you were about to make me lose my shit all over your gorgeous cock?"
"Yes." I continued to hold still.
"SO DO IT ALREADY! PUT IT BACK IN!"
I dragged my cock with agonizing slowness across her puckered hole until I could push my tip down the full length of her slit. I spent a few seconds rubbing circles around her clit before raising myself up until my tip was poised right against her sphincter.
Her body was strung out on endorphins and adrenaline. She desperately wanted the release - needed it physically. And that is exactly where I wanted her
"Shit, shit. Ok. Jesus, I swear if you hurt me I'll slaughter you in your sleep. But I don't trust you, so roll over. I wanna be on top."
"Tell you what. Why don't YOU roll over. That way I can watch your face. If I see that you're uncomfortable I'll stop, I promise."
I lifted up on my knees and she twirled onto her back. I encouraged her to separate her knees and I gently pulled her feet out from underneath me. With her ankles in my hands laid them on my shoulders and pulled her back until her steaming sex brushed my throbbing tip. This time I ran up and down a few times and slowly lowered my full length into her until she was almost folded in half.
"Is that better?"
"OMG, that's much better. But it's not my ass."
"I know. But I wanted you to enjoy this". With that I stroked in and out with my full length. Leaning down I tenderly kissed her, letting our tongues mingle as my shaft slowly entered and retreated from her.
Olivia wrapped her arms around me and began meeting my thrusts more and more eagerly as she banged her clit into my pubic bone.
Our speed ramped up until we were hammering against each other. I suddenly froze and shook from my head to my toes and collapsed on top of her.
She held me for a few moments and then pushed me up off her chest. "That was really nice, but I thought..."
"I know, crazy, right? But yeah. I thought you were gonna stick it in my ass."
"I might have gotten lost in the moment and changed my mind where you got my last load. No way would I be able to go again."
She almost looked crestfallen. "Uh, like, do I still get to keep the grand?"
"Oh no, that was for the privilege of your ass." No butt, no nut, no dough. Sorry."
"Wait, wait! I fucking earned that money! You can't take it back now!" Her eyes filled with just a hint of tears.
"So, what are you saying?"
"I need you to hold up your end of the bargain. We can wait if you want to. But I need this."
"What do you need?"
"I need you..." The absurdity of begging her begging me to fuck her ass suddenly dawned on her. And she was fine with it. "I WANT you to fuck my ass."
"You do? You're sure?"
"I hate you. I do. But at the same time tonight's been amazing on so many levels. Why not end it on a limb?"
"You're going to go out on a limb?"
"Yes, and trust you. Crazy, huh? But I still want to be on top."
She slapped my chest. "Get off me already!"
I did and laid across the middle of the bed. Olivia dug into the nightstand and pulled out the lube and liberally coated us with it. Straddling me she lined herself up and lowered her puckered ring until she made contact with me.
"Ok," I said quietly. "I'll hold still. Go slowly and take time to let your body adjust."
She relaxed a fraction and put more pressure on her sphincter.
"Roll your hips around. It can help."
What I hadn't thought of was just how amazing that would feel on my end. Literally. Her tightness was gripping me just under the flare of my mushroom head and twisting that around my shaft made me see stars it felt so good. I had told her I wouldn't thrust on my own, but I said nothing about flexing.
My cock swelled and shrank with each flex, letting another fraction of me inside. Eventually I got past her 2nd sphincter and from there she hesitantly lowered herself the rest of the way down.
"Fucking, fuck, that feels...weird," Olivia said through clenched teeth and and tightly closed eyes.
"Am I hurting you?"
"No, not 'pain' really. Uncomfortable yes, but a lot of it is just the weirdness of something huge going in an exit port."
"Take your time. Let your body relax, and then gently rock your hips back and forth."
She did. "OH!" she exclaimed as I found my way into parts of her body that had never been touched before. "I've had girlfriends tell me about this, and they said their man 'rearranged their guts'. I think I understand now! It feels like you're in my fucking stomach." Her hips started rotating and her eyes rolled back into her head.
"You feel incredible," I grunted. My hands encouraged her hips to rise and fall as well as twist.
We just explored for awhile, letting her control the movements and penetration. It became obvious that she was enjoying this as much as I was and soon was lifting almost all the way off me, then slowly sinking until her clit was against the base of my shaft. On her next lift I reached down and curled two fingers upwards. As she sank down my fingers parted her lips and entered her soaking sex. When she bottomed out against my hand I started pulling my fingers against her front wall and in moments she was barreling towards a massive orgasm.
So was I. "You'd better hurry girl, 'cause I'm about to..." and with a roar I went over the edge, blasting her bowels with my seed. The wild flexing of my exploding cock send her over the edge and we both thrashed about in our final orgasm together.
"Jesus H. Christ, I've never felt anything like that!" Olivia panted.
"Yeah, no kidding. You were AMAZING, Olivia. But now it's time for you to go. I have to get some sleep and then I HAVE to get back to work. You've more than fulfilled your requirements. I'll write you a note to see my doctor for a morning-after pill and give you another couple hundred for clothes."
"Wait, that's it? We're done?"
"Unless you'd like to do this again. I'd certainly be up for it. You're, uh, unlike anyone I've ever met."
"Gawd, don't go all soft on me big guy."
"Yeah, well it's a bit late for that," I said, looking down at my rapidly deflating cock.
"Tell you what, you want to make another grand?"
"I'm afraid to ask... but okay?"
"I'll give you a new iPhone. You keep your cash. I'll even get you a place to stay. But when the phone rings, you answer as Olivia and you do what you're told. Any time, no matter what. You're mine, bought and paid for. But I'll compensate you for your time. That way there's no question what our relationship is. Interested?"
"So basically I become your fuck toy, on call 24/7 for a fucking phone?"
"No, you become my fuck toy because that's what I pay you to be. The phone is just a bonus."
"No pain, right? No humiliation? I'm not into that shit. And you can't tie me up."
We went shopping for clothes, got her set up in a cheap apartment and of course a shiny new phone.
Now the fun part would begin, which was making her wait for the damn thing to ring...