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In an Ideal World

Category: Group Sex
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I was determined to make it the best summer of my life.

I’d graduated college the first week of May and immediately received an offer for a dream job in San Diego. It meant moving clear across the nation, but it was too good an opportunity to pass up.

The job started in September, so I had several months on my hands. I’d be working fifty hours a week come autumn and probably for some years after, so I decided a prolonged vacation was in order and had just the place in mind.

My parents owned a small vacation home near the beach in one of the sleepier towns down the shore. They would be in Asia until the last week of August, too, so I could bum around the vacation house until then without a care in the world.

I fell into a nice, easy routine right away. I’d usually get up around nine or so, taking my time starting the day. I love to bike and there was a long path a few miles away. Around ten I’d hit the trail, doing fifteen miles by the time I reached the far end and rode back home.

Afternoons I’d hang around the beach or sit on the front porch reading. At night I’d go out with friends or a few of us would hang out around the house grilling cheeseburgers and drinking beer.

I was seeing Alyssa, a girl two years younger than me and keeping it casual. I got the feeling sometimes that she wanted it to be more serious, but I wasn’t interested. Besides, I was moving two thousand miles away in a few months.

I’d always preferred older chicks, anyhow. In college I dated a doctoral candidate eight years older than me. I missed her sophistication and intelligence and hoped to meet someone like her in San Diego.

Meanwhile, I had my extended vacation to enjoy. Those morning bike rides were great. You have a lot of time to think while biking. Plus, the trail was populated by a variety of attractive ladies walking, running, or pushing strollers. Many looked in their thirties or early forties, just my type.

That’s where I first saw Diane and Allison.

Diane was the taller of the two, Italian-American with long black hair and flashing green eyes. She had medium-sized breasts and long legs. I guessed her age at around forty. I never did find out.

Allison looked the same age but was the opposite of Diane in a lot of ways. Allison was shorter and had pale blonde hair. Her features were soft and she had the kind of bright blue eyes that always make me smile. She was a lot curvier than Diane, too, with extra-large breasts and a delightfully-plump bottom.

They were walking in my direction and wore black exercise pants and tank tops. Diane’s was red, Allison’s yellow. I smiled and nodded as we passed. I couldn’t resist and turned my head back to check them out from behind and caught both of them glancing back at me.

I pedaled on, a wide grin on my face.

They were on the trail again the next day. I smiled at them as I whizzed past and they smiled back. Every day for a week or so I saw them walking together. I made sure to leave for my ride at the same time every morning in the hopes of seeing them.

I fantasized about them all the time. I’d get home from my ride, strip right down, and lay on my bed. I’d jerk off thinking of them.

Sometimes I masturbated thinking about Diane. Usually, I imagined myself on top of her. I’d close my eyes and picture us kissing as I pounded her pussy. I thought about her wrapping her long legs around me and that’s usually when I came.

Other times I’d think of Allison. I usually fantasized about her on top of me, her big tits bouncing up and down as she rode my cock. I imagined what it would be like to suck on those ample melons.

I enjoy curvy women like Allison. Yet I also find that a slender woman like Diane has her own particular charms. I’d have a tough time saying which I truly prefer. Diane or Allison, what a choice!

In an ideal world, I could have them both.

One day I was late getting out on the bike. Alyssa had come over the night before. We had sex and then drank too much. It was nearly eleven before I finally got out of the house.

I got a cramp in my calf as I reached the trailhead. I got off and started stretching it out.

At that moment, Diane and Allison appeared, finishing their daily walk.

“Hey, bike guy,” Diane said.

“Hey, walking ladies,” I responded.

“We missed you this morning,” Diane said.

“I was a bit late getting started,” I said.

“Hot date last night?”


“I’m Diane,” she introduced herself. “This is Allison.”

“Nick,” I said, shaking their hands.

“Nice to meet you, Nick,” Allison said.

We made small talk for a minute and they went on their way. I rushed through my ride, probably finishing in record time. Back home, I bounded upstairs to the bedroom and discarded my clothes. I lay back in bed and jerked off imagining Allison riding me while Diane sat on my face. I came in no time.

I saw them every morning for the next week or so. I’d nod, smiling and greeting them by name.

“Morning, Diane! Morning, Allison!”

“Morning, Nick!” They’d say in unison.

I didn’t see Diane and Allison one morning on the trail. I returned home feeling bummed, took a shower, and decided to grab some lunch. There was a pizza place nearby, on the far end of the business district. I decided to walk.

I was passing some stores on Main Street when Diane and Allison stepped out of a boutique.

“Nick!” Diane exclaimed.

“Hey, ladies. I missed you this morning.”

My eyes took them in. They were hot enough in their workout wear, but even sexier cleaned-up. Diane wore a purple button-down blouse and white capris. Allison wore a blue sleeveless blouse and white knee-length skirt. Allison’s hair was down, the first time I’d seen it that way. It was long and curly.

Diane had a mischievous gleam in her eye.

“So what’re you up to?” she asked.

“I was just going to get a few slices of pizza.”

“We were just headed for lunch, too,” Diane said. “Join us!”

“I, uh,” I stammered like an imbecile.

“Come on,” Allison chimed in. “Our treat.”

“OK,” I said. “That sounds nice.”

The restaurant they were headed to was only a few doors down. It was an upscale place serving rustic Italian cuisine and doing a pretty good job of it. The food was fantastic, though not half as great as the company.

The ladies insisted on a bottle of white wine to go along with the meal. I was a bundle of nerves but the first glass put me at ease. I became more talkative and told them all about the job in San Diego and how excited I was.

I learned a lot about them, too. Allison was divorced with two kids at home. Diane was married and the mom of a seven year-old. She rolled her eyes when she talked about her husband. I got the impression she wasn’t thrilled about matrimony. At least the monogamy part.

“Nick, I wonder if you could help me with out with something,” Allison asked as we finished our meal.

Diane cast Allison a sly grin.

“I need to move a heavy chair,” Allison continued. “Would you mind?”

“No. I’d be happy to do it.”

“Good. We’ll swing by my place after we’re finished.”

Diane’s car was right out front. It was a powder blue Mustang convertible. She insisted I ride up front with her and Allison sat in the back.

Allison’s house was a humble little cape cod that looked well-kept. It wouldn’t have been anything special, except it was two blocks from the Atlantic Ocean. Allison’s ex was a big shot lawyer and she got the house in the divorce.

Allison opened the front door and I followed them into the living room.

“Let me get you a refreshment,” she said. “Sit down. Relax.”

Allison left, saying something about lemonade. I took in my surroundings. Her house was clean and stylish, decorated in a sunny shore motif. It fit her.

I turned to say something to Diane. Before I knew what was happening she pulled me close to her and kissed me. My lips parted and she shoved her tongue into my mouth. I wrapped my arms around her waist and pulled her tight against me.

Diane grabbed my ass with both hands as we kissed. My mind was racing, hardly able to comprehend this was happening. I went with the flow, enjoying the taste of her lips and tongue.
We heard Allison returning and Diane pulled back. We were still standing close together when Allison reentered the living room bearing a platter with a pitcher and three tall glasses filled with ice and lemonade.

Allison put the platter down on the coffee table and handed us our drinks. I took a sip and tasted the alcohol.

“Thought I’d throw in some vodka,” Allison said cheerily. “Why not? To new friends!”

“To new friends!” I responded.

We clinked glasses and drank again.

I complimented the house and Allison began talking how much work she had done to it since moving in two years earlier. Her hand brushed my arm a few times and she kept looking into my eyes and smiling.

I nodded and smiled back, sipping the spiked lemonade and considering my situation. Diane definitely wanted me if that kiss was any indication, and I thought Allison felt the same way. I didn’t have the nerve to suggest the obvious, though. The downside was too big if they weren’t into it.

Then Allison put all my doubts to rest.

“You’ve got such nice muscles,” she observed, reaching out and caressing my arm.

Our eyes met. She leaned forward and gave me a long, open-mouthed kiss. She tasted different than Diane, more sensual.

Allison broke off the kiss first, gently withdrawing.
“Come on,” Diane said, taking my hand. “Up for a little fun?”

They led me upstairs to Allison’s bedroom and proceeded to strip me. Allison kissed me hard on the mouth and then took off my shirt. She resumed kissing me while Diane pulled down my shorts and underwear. I kicked off my sandals and found myself standing naked between them. It was a good place to be.

Their hands roved over my chest and stomach as they took turns kissing me. Allison reached down and began stroking my cock. It was fully erect by then, standing proud at just over seven inches.

“You’ve got such a nice cock,” Allison said. “We were hoping you had a nice big cock to fuck our wet cunts with!”

Allison had a secret. She was president of the PTA and never heard to utter even the mildest profanity in public. Behind closed doors, however, she was an insatiable bisexual who loved to talk dirty. By dirty, I mean the most creatively filthy stuff I’d ever heard a woman say.

Diane reached down and gently caressed my balls as Allison kept stroking the shaft of my cock. I shuddered, sighing with delight. I could scarcely believe my good fortune.

“I want your cock in my cunt,” Allison whispered in my ear. “I want you to fuck my wet little fucking cunt. Can you fuck my slutty cunt good?”

“You bet,” I said.

Diane began kissing my neck and nibbling my earlobe while I enjoyed Allison’s lips and tongue. They were both talented ladies with their mouths, confident and experienced. They were the kind of women I’d dreamt of all my life.

“You ladies are overdressed,” I murmured.

“I’ll have to correct that,” Diane said. She stepped back and slowly began to remove her blouse. I watched her undo each button as she swayed slowly and licked her lips for me.

Meanwhile, Allison knelt in front of me.

“I love a big throbbing cock in my mouth!” she said, licking the tip of my cock. “I’m a cocksucking whore and I love it!”

Diane stripped off her blouse. She had on a white bra underneath which she undid and threw aside. My eyes fixated on her rose-colored nipples.

Allison slid the rest of my cock into her mouth and began sucking me back and forth. I still couldn’t quite believe what has happening. I was lost in joy.

Diane slid off her capris. She turned around, sticking her ass out. She moved her butt back and forth for my entertainment and slid her panties off. Her ass was gorgeous, round and inviting.

All the while Allison sucked on my cock, my hips gently thrusting into her mouth. Diane stood, kicking off her shoes and turning towards me. Her pussy was as black as the hair on her head. It was hairier than I was accustomed to, but that was fine.

Diane kissed me and then knelt down next to Allison.

“My turn,” she whispered.

Allison took her mouth off my cock and pointed it towards Diane.

“Suck him, you cocksucking whore!” she said. “Suck that cock! Go on, slut! Suck it!”

Diane took me into her mouth and started sucking me gently. Allison stood. She kissed me and then stepped back.

It was her turn to strip.

As Diane’s head slid back and forth on my cock, Allison undid the front of her blouse and let if fall to the carpet. I stared at her exceptional tits. I’d say she wore a DD-cup, if I had to guess, maybe bigger.

She undid her bra and her tits broke free. They had a little sag to them, just like Diane. It was all part of that mature femininity I adored. I especially liked her lovely light-pink nipples.

I watched as Allison slide off her skirt. I was delighted to discover that wasn’t wearing panties. I also learned she shaved her pussy.

Diane sucked me at a nice slow pace, enough so that I felt great but not enough to make me come. Allison approached me and we kissed. My hands explored her big tits and she moaned.

Diane pulled her mouth back, jerking my cock a few times before standing. The ladies gently guided me towards the bed and got me on my back. Allison lay next to me, her mouth seeking out mine. We began making out furiously.

Diane straddled me and guided my cock into her pussy. She was dripping wet and I entered her in one fluid motion. I groaned and smiled.

Allison looked at her friend, her eyes wide with excitement.

“That’s right!” she shouted. “Ride that fucking cock good, you fucking slut! You know you want it, you stinking whore! Fucking ride that dick up you cunt! Fucking ride it until you fucking come, bitch!”

Allison kissed me again, our tongues twirling in each other’s mouths. My hands sought out her tits and I cupped them gently. She moved up and shoved them in my face. I licked her nipples, sucking on each big tit in turn.

Diane’s pace quickened. She was moaning and bouncing on my cock. One of her hands rubbed her clit as she rode me. I kept sucking on Allison’s tits. I was in heaven.

“You want to eat my pussy, motherfucker?” Allison whispered. “Huh, you want to lick my wet cunt?”

“Yes,” I managed to gasp.

Allison got up and then squatted over my face, turned towards Diane. Her plump butt cheeks were right above me and her beautiful pussy mere inches from my tongue.

I lifted my head and began licking her. She was soaked but I took it slow. I licked her clit up and down for a while and then started to increase the speed of my tongue. I sucked her clit and she responded, shuddering and groaning. The whole time, she went on with her profane play-by-play.

“That’s it, you fucking dirty boy! Lick my motherfucking clit! Lick that fucking clit! Oh, yeah. Suck my clit like that again!”

Diane’s moans grew more high-pitched. Allison, meanwhile, had stopped her dirty talk. I couldn’t see much, but I felt the way they leaned into one another and figured they were making out.

I began thrusting upwards harder into Diane, still licking Allison’s clit the whole time.

Diane started to shriek, still bouncing up and down on my cock.

“Oh, fuck!” she wailed. “I’m gonna come! I’m gonna come!”

Her body shuddered and she screamed.

“Oh, yes! Yes, yes, yes!”

Her cries grew less intense as her orgasm waned. She kept riding me, though.

“How’d that cock feel in your cunt, whore?” Allison asked her. “I bet it felt good in there, fucking your filthy slutty cunt! Yeah, that’s some cock! I want it to fuck my swollen filthy whore cunt, too!”

Diane climbed off and lay next to me. Allison took her place. She wasted no time, thrusting up and down on my cock. Her big tits bounced to my delight.

I groaned and thrust back up into her. I knew it wouldn’t be long before I came, but wanted to make sure Allison had her orgasm first.

“That’s it, motherfucker!” Allison groaned. “Fuck me, motherfucker! Fuck me, fuck me, fuck me!”

Her groans grew into loud screams.

“Fuck me! Fuck me! Fuck my filthy dripping cunt!”

Diane lay next to me, her hand on my chest as she watched Allison riding my cock. I began tongue-kissing Diane as Allison groaned wildly.

“Oh, I love fucking you like this!” Allison yelled. “Give it to me, motherfucker! I’m gonna cum all over your big dick! Oh, fuck me! Fuck my smelly fucking cunt!”

I kept making-out with Diane as Allison rode me. I was thrusting up into Allison rapidly and knew I couldn’t hold out much longer. Then Diane slid her tongue into my ear and I had no chance of holding back.

“I’m gonna come!” I moaned.

“Go ahead, baby,” Diane whispered, licking my ear furiously.

“Do it, motherfucker!” Allison barked at the top of her lungs. “Shoot your fucking hot fucking cum into my cunt! Fill my wet slut pussy up with it!”

I thrust into Allison, my orgasm approaching. I froze, my cock suddenly throbbing violently. Each throb sent a squirt of cum into Allison’s pussy. She loved it, howling and bouncing harder than ever.

“That’s it, motherfucker! Fill me with your motherfucking juice! I love your cum inside me!” she wailed, still bouncing on my cock. “Oh, I’m such a fucking whore!”

She came right after that, screaming and shrieking a symphony of profanities. When she was done, she dismounted my cock and lay down in the bed. She snuggled in close against me on the opposite side of Diane. They each gave me a long open-mouthed kiss and then leaned over and kissed each other.

We lay together for a while, caressing each other gently.

“Well, that was nice,” Diane said.

“Fucking awesome,” Allison chimed in.

“Can I ask you ladies something?” I said

“Go ahead,” Allison said.

“Is there really a heavy chair you need me to move?”

They laughed.

“No, that was a lie.” Allison hung her head in mock shame. “I hope you can forgive me.”

We got together the next day at my place and had another amazing time. Afterwards, we lay around talking. I learned Diane and Allison had been fooling around which each other for more than a year. They’d been talking about finding a guy to join them, and then I came along.

“We took one look at you, honey, and decided you’d be perfect for us,” Allison said.

“That’s not all,” Diane added. “We’ve got a proposition for you, one we think you’ll like.”

Diane and Allison wanted me to be their sex toy until September when I had to leave. I would make myself available for them whenever they wished, be it individually or otherwise.

Hardly a day passed the rest of the summer when one or both of them didn’t drop by. Diane would come over when her husband was working late and her kid was with the neighbors.

Allison and I got together whenever she could get away from her kids. The week they were at day camp we spent entire afternoons naked and all over each other. Diane joined us whenever she could.

I grew to know their sexual tendencies well. Diane was the more athletic lover, for example, but Allison had her soft curves and the dirty talk.

Also, Diane sometimes wanted tender lovemaking. On those occasions, I would take her by the hand into the bedroom and we’d enjoy an hour or so of sweet, gentle sex.

Allison, however, wanted nothing but raunchy, often rough, sex. I was happy to oblige, of course. Afterwards, though, we’d talk. We talked about everything in an easy manner like we’d been best friends for years. I told her things I never thought I would be able to tell another human being, and she confessed her share of deep, dark secrets.

If I were staying in New Jersey, I would have fallen hard for her.

I broke it off with Alyssa right after that first time with Diane and Allison. I tried to let her down easily, explaining how two-thousand miles was too far for a long-distance relationship and it was best to make a clean break. I told her I wished her all the happiness in the world and kissed her goodbye. I thought that would be enough.

It wasn’t. Alyssa dropped by the next day. I never learned why. Diane, Allison, and I were naked in the living room and going at it when Alyssa barged in.

“You fucking bastard!” she screamed and ran out.

The last night I was in town Diane and Allison came over and they fucked my brains out. I came four times over the course of the evening, but that’s another story.

They kissed me goodbye when we were done and slipped out of bed. I never saw them again.

They left me a present on the kitchen table downstairs. It was an insanely expensive watch. On the inside of the band was engraved the words “Remember always, D & A.”

I still think of Diane and Allison nearly every day.

When I do, I glance at my watch and smile.

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