Loading...Jill walked in, still in her work clothes. She wore a blue dress shirt and dark gray skirt. Her outfit was conservative but showed off her curves nicely. She spotted me and came over.
I noticed a guy at the far end of the bar watching her. I didn’t blame him. It was hard to ignore Jill. She’s tall and slender attracts a lot of attention with her high heels and assertive aura.
Her hair was up but I’d seen the way her long black locks spill down over her shoulders when she’s relaxed. I’ve also seen her naked on all fours demanding I fuck her ass harder.
I hadn’t heard from her in a month beyond the stray text message. Then she texted me the day before and asked to meet for a drink after work. She said she had to ask a favor.
Jill and I were friends-with-benefits. We’d been getting together for more than a year, sometimes talking and hanging-out. Mostly, we met at one of our apartments and fucked each other’s brains out.
Jill was not timid about sex, either. She enjoyed it and wasn’t ashamed.
She sat down and we said hello. She gave me a quick kiss on the lips.
“Jim Beam,” she told the bartender. “Over ice.”
“So, how have you been?” I asked.
“Stressed-out,” she said. “McDougal dumped that damned Schneider case on me, just like that. I’ll be working on it till past midnight.”
“Oh, that sucks.”
“Yeah.”
“Well, you look great,” I told her. “Stressed-out or not.”
Her drink arrived and she took a long sip. I could tell she was tired.
“You’re working too hard,” I observed.
“I know,” she sighed. “God, it’s been a long day.”
“Care to talk about it?”
“Not really. I’m sorry I’ve been neglecting you, though.”
“Well, you’ve been busy.”
She took another sip of her drink.
“I haven’t had sex in two weeks,” she complained. “I’m working late every night. By the time I’m done, I’m too-tired.”
“Are you too-tired right now?” I asked.
She raised an eyebrow, considering my offer.
“You can always work on the case afterwards,” I suggested.
Her olive green eyes flashed and the barest hint of a smile crossed her lips.
“Why not?” she said.
***
We hopped in a cab and headed for her apartment. I put my hand on her knee and moved it up her thigh. We started making-out in the back of the taxi like a couple of teenagers. I noticed the driver eyeing us in the mirror.
The taxi pulled up to Jill’s building and we went in. We said hello to the doorman as we casually strolled through the lobby.
No one was in the elevator and as soon as the doors closed we were all over each other again, kissing and groping madly. We stopped when the elevator reached Jill’s floor.
We grinned at each other while she got out her keys and opened her door, enjoying the little game.
Once inside, Jill kicked the door closed behind us and we got right back to it. I grabbed her and pushed her against the wall, kissing her neck and feeling her tits. They are small, but ideal for her frame. I’m fine with big tits, but a pair of huge boobs wouldn’t have looked right on Jill.
She moaned, grabbing my head in both hands and shoving my face against her chest. Still pinned against the wall, she lifted her legs up and wrapped them around my waist. I stood up straight and we shared a long and lurid kiss.
We stumbled into the bedroom, kissing and stripping along the way. By the time we got there, Jill was down to her bra and panties and I was in nothing but boxers. I undid her bra. Her tits free, I pawed them roughly and kissed her neck. She growled, grabbing my ass.
Jill liked it on the raunchy side. She also like to talk dirty, her words becoming progressively filthier the more aroused she became.
“Let’s see that big cock,” she whispered.
She pulled down my boxers and put her hand on my cock. At seven inches, it’s not huge but I haven’t had any complaints.
She knelt in front of me, stroking my cock tenderly. She looked it over, smiling.
“I’m gonna fucking devour this thing,” she said.
She started sucking me, slow at first but then quickening.
I took my hands and put them on her head, grabbing handfuls of her hair. She went on sucking my cock for long, wonderful minutes.
“I want to fuck you so bad,” I told her.
“You want to fuck me, do you?” she teased, jerking me off.
“I do.”
“How do you want to fuck me?”
“From behind,” I said.
“Then get to it, boy.”
Jill stood, sliding off her panties and climbing onto her bed. She got up on all fours with her ass facing me. She arched her back and stuck her round but into the air. I took a moment to appreciate her. Jill’s on the slender side, but not scrawny. Rather, she’s lean and athletic. She ran track in college and still got up at six to run every morning. It showed.
I climbed in bed behind her, my hands roaming over her ass cheeks.
Her pussy was soaked and my cock slid right in.
“That’s it!” she sighed. “Now, fuck me! Fuck me good!”
I began fucking her nice and steady. She started to whimper and I sped up. I reached out with both hands and grabbed her hair. I pulled on it and she started moaning.
We fucked like that for a long time, her moans growing slowly louder until they morphed into screams echoing off the walls.
“That’s it! That’s it! That’s it! Fuck me! Fuck me!”
Her screams became one continuous howl as she came. I was so turned on I only lasted a minute or two longer. I came inside her, gasping happily.
I pulled out of her and we lay down on the bed.
“Feel better?” I asked.
“Oh, yeah,” she said. “I was going to have you switch to my ass, but I felt myself coming and went with it. Maybe next time.”
“Give me twenty minutes to recover,” I suggested playfully. “It’s only six-thirty.”
“Yeah, except I’ve got work to do tonight.”
I kissed her and got out of bed. I pulled my boxers back on and started to get dressed.
“Drink?” Jill asked.
“Sure.”
I went into the living room and poured us two bourbons over ice. We always shared a drink after sex and hung out for a few minutes. After the drink, I usually split.
Jill came out wearing a t-shirt and jeans. Her hair was in a ponytail. She sat down on the couch next to me. I put my arm around her and she leaned against me as we had our drink and talked.
I drained the last of my drink and stood, ready to leave.
“I almost forgot,” I said. “What was the favor you needed?”
Jill laughed.
“I’m so wound-up I forgot to bring it up,” she said. “Distract a girl with a little hard fucking and she forgets her name. Sit down. I’ll pour us both another.”
***
“So what do you think?” Jill asked when she was finished laying it all out. “Will you do this?”
“Give me some time to think about it,” I told her.
I finished the last of my second drink and we said goodnight.
I hailed a cab and headed home. I kept re-running in my mind what Jill just asked me to do. I knew she was a girl who liked sex, but this was more than I imagined.
“I’m going to be thirty in a few months,” she started off. “Maybe it’s time I settled down, started looking for something more serious.”
“You want me to fix you up?”
“Not exactly. No, what I want from you is your help bringing about a fantasy of mine. I don’t want to settle down without experiencing it.”
“Okay, so what is it?”
She looked me directly in the eye.
“I want to get fucked,” she said evenly. “By three guys at the same time.”
“Whoa.”
“I’ve dreamt of it for years. Lately I find myself daydreaming about it constantly. I did two guys at once, one time in college. But three guys…for some reason, the notion of three men at once is my ideal. I don’t know why, but it has to be three. Not two, not four or twenty-seven. Is that odd?”
“No,” I said. “I mean, you can’t help what turns you on.”
She paused, sipping her drink.
“I want you to be one of the guys, of course,” she said. “You’re my type and you’re open-minded sexually. Plus, we have great chemistry in bed.”
“We do indeed,” I agreed. “Do you, uh, have the other two guys lined-up?”
“No, that’s the favor I was going to ask. I need you to find the other two guys and set it all up.”
“Oh.”
“This is not an easy fantasy for a woman to make come true,” she explained. “Not if she wants to be safe. You might think all I have to do is walk into the bar down the street, pick three guys at random, and it’s back here for the fuckfest.”
“Believe me,” she went on. “I’ve thought of that.
It’s too risky for a woman with complete strangers. They could be sociopaths. Placing an ad online is even more dangerous. But if a guy I trusted put the whole thing together…”
“You’d feel safe.”
“Precisely.”
I stared out the window of the taxi thinking about Jill’s request. Maybe it was the taboo factor, but I began to find the notion of banging Jill along with two other guys immensely arousing. I found myself wanting very much to do this for her.
I typed out a text to Jill and sent it.
“I’ll take care of everything,” it said. “Keep you posted.”
***
Two weeks later, I was sitting with Scott and Dave in the bar of one of the top hotels in the city. We sat at a booth watching the door. I checked my watch. It was three minutes to six.
“She’ll be here in a minute,” I said. “She’s never late.”
They nodded and sipped their ginger ales. When Jill arrived, we’d have one drink to loosen up but not enough to dull our senses.
I knew Scott and Dave from my swim club and I’d hung out with them a bunch of times over the years. They both had girlfriends and decent jobs, personable guys with sex-positive attitudes. They were also good-looking and had the same lean swimmer’s build as me which Jill preferred.
I met them for a beer the week before and told them all about Jill and her request. They were intrigued. Then I showed them her picture and they became very interested.
It was all arranged. We had a suite upstairs. It cost a bundle, but all four participants split the cost. Jill insisted on paying her share, pointing out these were modern times and the whole thing was, after all, her idea. She also gave me a duffle bag containing whatever she needed in terms of a change of clothes and other supplies. It was up in the suite.
Everything else we might need was waiting in the suite. There was liquor in the minibar in case we wanted another drink later. We also had bottled water, extra towels, and plenty of lubricant.
We all noticed Jill enter the lobby at the same time, Scott and Dave’s jaws dropping.
She wore a dark blue suit that hugged her curves. It featured a long sleeved buttoned-front jacket and knee length skirt. She had on matching high heels, as always, and her hair was up. Every male head in the bar turned at her approach.
“Wow,” Scott and Dave gasped in unison.
She came up to us and we stood. Everyone introduced themselves and shook hands. It was all oddly formal considering the context.
The waitress came by after we sat back down. Jill and I ordered bourbon, Scott and Dave gin martinis.
We chatted a while, the one drink easing the tension. Jill asked Scott and Dave about their work and what they did for fun. I noticed her carefully checking them both out the whole time. I could tell she liked them.
“Gentlemen,” she announced, finishing her drink. “If you’d care to go upstairs, I’m ready.”
Up in the suite, Jill looked around.
“It’s nice.” She glanced at me. “Good job.” She picked up her duffle bag and headed for the bathroom.
“I’ll just be a few minutes, gentlemen,” she said. “Please get comfortable, by which I mean naked. Furthermore, I would like to thank you all in advance.”
Jill disappeared into the bathroom.
“She doesn’t mince words, does she?” Scott said.
“No,” I answered. “She doesn’t.”
We took off our clothes and stood there feeling awkward. We’d seen each other naked plenty of times in the locker room, but this was a much different situation.
The door to the bathroom opened and out stepped Jill. She’d shed her formal attire and wore an entirely different kind of outfit.
It was all black leather, starting with the thigh-high boots and matching corset. She topped it off with a studded collar around her neck. Her breasts and shaved pussy were on full display and her hair was in a ponytail.
“Gentleman.” She strode up to us. “My fantasy has always been to be fucked by three men. I hope you are up for the task.”
The three of us drew closer to her. She looked into each of our eyes in turn.
“Have at it, boys.”
Dave got it started, kissing her mouth. She responded, reaching down and grabbing his cock. Scott moved in close on the other side, kissing the back of her neck. She moaned.
I reached out and felt her tits. She broke off the kiss with Dave, glancing at me. There was a fire in her eyes, a lust unlike anything I’d ever seen before. Here was a woman experiencing her most-cherished sexual fantasy, and reveling in it.
I leaned in and kissed her. She shoved her tongue into my mouth, Scott still kissing the back of her neck as Dave nibbled on her earlobe. Jill closed her eyes and sighed with pleasure.
Jill’s mouth moved around to kiss all three of us in turn. Whoever she was kissing, the other two stayed busy kissing her ear lobes or licking her neck.
The whole time, six hands explored her body. There was never a time when a hand was not on both breasts and both ass cheeks.
I was surprised by how intensely erotic it was for me. I thought this would be fun and exciting, but it was far more so than I imagined. I could sense Jill’s pleasure and fed off of it.
It went on that way for a while, everyone getting warmed-up. Then Jill knelt before us. She took Scott’s cock in one hand and Dave’s in the other. She began to slowly stroke them. She looked up at me and flicked the tip of my cock with her tongue. Then she took me into her mouth and started to suck my entire length nice and slow. I let out a sigh of pleasure.
Jill switched to sucking Scott’s cock. She did not neglect Dave or me, though, her hands stroking our cocks gently. She eventually turned her head and gave Dave a nice, long suck.
I noticed Dave had the biggest cock out of the three of us. Scott looked the same size as me, but Dave was at least an inch longer.
Jill turned back to my cock, sucking it at a faster pace this time. Then she switched to Scott and back to Dave. She sucked us for a long time in that fashion, moaning.
“I so love sucking cock,” she sighed.
She stood up. We all kissed her again and moved towards the queen-sized bed at the center of the room. She lay on her back between Scott and Dave. I watched for a while as she tongue kissed Dave and then turned her head and did the same with Scott. She stroked both of their cocks and whimpered softly.
I climbed onto the bed and positioned my face between her legs. Pulling aside her pussy lips, I inhaled her musty aroma and began licking her clit slowly. She was already soaked with arousal.
“Oh, that’s it!” Jill moaned. “That’s it! Lick my pussy!”
I kept licking Jill’s clit while Scott moved down to her tits and started sucking on them.
I sat up, ready and eager to fuck her. I rubbed my cock on her clit a few times and then entered her pussy.
“Oh, fuck!” she groaned. “Fuck, yes! Fuck me with that cock!”
I started fucking her, enjoying the warmth of her wet pussy and the view of her playing with Scott and Dave. Dave moved down to her breasts and started sucking the right one while Scott kept sucking on the left.
Jill started squealing and I fucked her faster. She let out one of her prolonged howls and came, her first orgasm of the evening. There would be several more for her.
“Fucking yes!” she screamed. “Come on, guys. Let’s get those dicks of yours back in my mouth!”
Scott and Dave got up on their knees and knelt on either side of Jill’s head. They propped her shoulders up with a few pillows.
She started sucking their cocks again, switching back and forth. I fucked her even faster than before, transfixed. I knew I was hogging her pussy a bit but I couldn’t help it right then.
I felt my orgasm approach. I pushed in as deep inside Jill as I could. My cock throbbed again and again, one of the longest and most powerful orgasms I’d ever achieved.
“Holy shit,” I muttered, pulling out of her.
“I want you guys in both ends of me,” Jill said, getting on her hands and knees.
Scott moved around behind her. I watched as he slipped his cock inside her in one fluid motion.
“Oh my god, Jill, you feel good,” he said.
“Come on, baby!” Jill responded. “Fuck me good!”
Scott started fucking Jill’s pussy as Dave came around in front of her. He pointed his dick towards her face and she began to suck it. She sucked and jerked him the whole time Scott fucked her.
I knelt next to her and ran my hands over her back and massaged her tits as they fucked her from both ends.
It went on that way for several minutes. Jill moaned with delight the entire time.
“Fuck yes!” she started to screech. “Fuck! Fuck! Fuck! Harder!”
Scott started drilling her as fast as he could and Jill let out another howl as she came again.
Scott came a minute later, stopping suddenly. His eyes closed and he let out a grunt as he filled up her pussy and mixed his cum with mine.
As soon as Scott withdrew from Jill’s pussy, Dave took his place. I saw Jill’s eyes bug-out as she felt Dave’s extra length stretching her canal.
“Oh, fuck!” she exclaimed. “Holy shit I love that big cock!”
Dave began thrusting into her. I didn’t think Jill was going to come again right away, but his bigger cock made the difference.
Scott knelt beside her, kissing her neck and caressing her tits. I leaned in and gave Jill a kiss on the mouth. It was long and passionate. I got a strange thrill out of kissing a woman while another man fucked her.
“How you doing, baby?” I asked her.
She smiled widely and rolled her eyes.
A minute later Jill was back to screeching loudly. I grabbed her ponytail and gave it a tug, pulling back her head. That put her into overdrive.
“Fuck me with that big cock!” she yelled. “Fuck me! Fuck me! Harder, motherfucker!”
Jill came again, closing her eyes and riding the wave of her third orgasm. I was overjoyed along with her. The more she enjoyed herself, the happier I became.
Dave had his orgasm soon after. He let out a long groan and closed his eyes. Then he pulled out of her and all four of us lay back in the bed. Jill wound up between Scott and me. We were all quiet, lost in our thoughts.
***
Jill asked for water a few minutes later, so Scott got her a bottle. The guys all took a turn in the restroom, then returned to the bed. No one got dressed.
“I’m all sweaty in this get-up,” Jill said. “I’ll be right back.”
She went into the restroom.
“Isn’t she something?” I said.
“She’s like some kind of…fucking sex goddess,” Scott said. “I’ve never met a woman like her.”
“She’s un-fucking-believable,” Dave said.
“I’m in love,” Scott sighed.
“You and me both, man,” Dave added.
Jill returned a minute later, her corset and boots removed along with the collar. Her hair was still in a ponytail. She climbed back into bed with us, this time snuggling between Scott and Dave.
“You guys have such nice bodies,” she remarked. “You three must live at that swim club.”
She felt their chests and shoulders, smiling sensuously. They smiled, enjoying her hands.
Dave kissed her and she responded. While they made out, Scott nibbled on her neck. I watched her hands move down to stroke their cocks.
Jill sat up, gently pushing Scott and Dave flat on their backs. Jill took both of their cocks into her hands and stroked them back to full hardness. She leaned over, sucking each cock in turn.
I stood next to her. She grinned up at me and took my cock into her mouth. My half-erect cock turned hard in seconds. Jill blew me long and slow as she jerked-off Scott and Dave.
Then Jill took her mouth off my cock and glanced up at me again. She gave me a wink, leaning over and sucking first Scott’s dick and then Dave’s. She tried to take his full length into her mouth but couldn’t.
“Damn, you’re big,” she told him.
“Thank you,” he said.
“Ready for more of my pussy?”
“Climb on up, babe.”
Jill straddled him, lowering herself atop his cock as she faced him. She must have still been soaked, because his eight inches went all the way in without effort.
Scott and I stood on either side of Jill. She took our cocks in her hands and alternated sucking us, all the while riding Dave’s cock.
Soon I was as excited as before, my cock as hard as it’s ever been. Jill was moaning again and started sucking us off faster. It went on for a while. Then she looked up at Scott and me.
“I want to feel a cock in my ass,” she said. “Come on, Scott. Fuck my ass!”
Scott went over to the dresser and fetched the tube of lubricant. He brought it back, smearing plenty on his cock and applying a dab to Jill’s asshole.
Jill leaned foreward and placed her hands on Dave’s shoulders for support, pushing her ass up at a higher angle. Scott inserted his finger in her asshole, stretching it out slowly.
I watched with rapt fascinating as Scott entered Jill’s ass. He slid in his cock as slow as possible, letting her ass adjust. Jill’s face contorted with pleasure and her eyes grew wide.
“Oh, fuck!” she shrieked. “I’ve got two dicks in me! I’m being double-penetrated and I fucking love it!”
Scott and Dave began fucking her in tandem. Dave thrust up into her as Scott began drilling her asshole. I enjoyed the show for a few moments and then got into the action.
I stood in front of her and she smiled, looking up at me.
“Thank you so fucking much for this!” she said.
She began sucking my cock. I looked down and could see Dave underneath her. His eyes were closed and he was groaning. Scott, meanwhile, was wide-eyed and looked overjoyed as he pounded Jill’s ass.
Jill was moaning loudly, close to coming. She kept sucking me, pausing only to catch her breath.
“Fuck my ass!” she shouted during one pause. “Fuck my ass! Fuck my ass! Harder!”
I’d never seen a woman in such a state of sexual arousal. It was incredible.
Scott started fucking her ass like a madman. She began to moan loudly, still sucking my cock.
Suddenly, she pulled back from my cock and started screaming again.
“Fuck, yes! I’m gonna cum! Fuck, fuck, fuck!”
Jill’s latest orgasm passed a short time later and she went right back to sucking on my cock. Scott and Dave kept fucking her.
Scott was next to come, her tight ass more than he could take anymore. I watched him freeze and knew his cock was coming inside Jill’s ass.
I pulled my cock out of Jill’s mouth and went around behind her. The tube of lubricant was on the bed and I smeared some of the contents on my cock.
Scott pulled out of her and stepped aside. I took his place, sliding my cock right into her stretched-out ass. I started fucking her at a good pace, savoring the tight feeling of her ass wrapped around my dick. I could feel Dave’s cock in her pussy pushing up into her.
“Oh, yeah!” she started to scream. “That’s it, Brett! Fuck my ass! Fuck it, fuck it, fuck it!”
I reached forward and grabbed her ponytail. I yanked it back, harder than usual.
“Oh, fuck me boys! Drill my ass and my cunt! Fuck yes, motherfuckers! Fuck me!”
I started fucking her faster, unable to hold back. The turn-on was so strong I could feel I was going to come again real soon.
Jill kept screaming, growing louder as she came yet again. My own orgasm arrived at the same moment. My cock throbbed inside her butt, each pulse sending more of my cum into her ass.
Her screams subsided and I pulled out of her. She sat up, bouncing up and down on Dave’s cock. She soon started howling again.
“Fuck, yes! I’m gonna come again! Oh, fuck! Oh, fuck! Oh! Oh! Fuck!”
Dave came a short time later, staring up at her with eyes wide with delight and awe.
Jill climbed off his cock, plopping down on the bed. We all lay sprawled, out of breath and in a state of happy contentment.
***
Scott and Dave left soon after. Jill gave them each a warm kiss and hugged them tight.
“Thank you so much,” she told each of them.
“Well,” I said after the door closed. “How do you feel?”
“Never more fully a woman.”
We took a long, hot shower and got dressed.
Her building wasn’t far so we decided to walk. I carried her duffle bag. She’d changed back into her business suit but wore comfortable shoes now instead of her customary heels.
“So, still stressed-out?” I asked.
“Not anymore. Towards the end, it was just one long orgasm. Thank you again. Now I can think about settling down without regrets.”
“I loved every minute of it,” I said. “Watching you experience such pleasure, my own arousal went through the roof.”
She looked at me and smiled. She took my hand and we strolled the rest of the way to her apartment that way.