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Bachelor and Bachelorette

Bachelor and Bachelorette

by Maloryloder
20 min read
4.31 (6500 views)
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I told Kelly it wasn't cheating because I wasn't into girls.

"But you are into girls," she argued, fairly.

"No, I'm into just one girl. Otherwise only boys," I said.

"You are hopelessly in love with that one girl. And you're fucking me, which I gather you don't entirely hate."

"No, I don't hate it. But that's because I'm in love with a girl and fucking another girl is a balm, I guess."

"Yeah, you're into girls," affirmed Kelly.

"I guess, but I like boys too."

"Look, it's fine. You don't have to justify it to me. I'm just saying, we've been hooking up all Summer, and the fact that you've previously only ever been into boys but now happen to be deeply in love with a girl doesn't get me off the moral hook for cheating on my girlfriend."

I knew she was right. I wasn't so much trying to justify her infidelity as I was my own little problem. Our team of camp counsellors had grown very close, but I had kept Jane at an arm's length because ever since the minute I saw her get off the bus I knew I was feeling something new. It almost frightened me how beautiful she was, and when I learned she was also kind and spirited, it was all over. In the early weeks, Kelly had been complaining a lot about missing Kellie (don't ask), and Jane had started cozying up to one of the male counsellors. So in a moment of uninhibited horniness, I went to Kelly privately and asked if I ate her pussy would she stop crying about her girlfriend. She took exactly five seconds of convincing.

It wasn't my first time in the position, although previous times were all in a drunken party girl kind of context. I had always been led to believe I was something of a natural, which might explain my willingness to have a go at the most experienced lesbian at the camp. My first time with her was quite mechanical, that is she took off her own pants and laid down on her cot and I crouched in a downward-facing dog while I lapped at her. It wasn't romantic, or even especially sexy, although I was getting off also on the idea of getting a woman off, and with no offence meant to Kelly, it was Jane I had in mind always. This squared anyway with Kelly, who clenched her eyes tight as my tongue ran across her pussy. She dreamed of Kellie. She dreamed of a world where it remained true that only Kellie could make her come.

I haven't always been conniving, but I learned from the best. That was how Kelly repaid me for soothing her relationship woes. She and I decided to contrive a scenario wherein all the girls would take part in a blind-folded pair-off in order to explore the beauty of the female form. The point was that nobody but Kelly would know whose partner was who, but secretly, she agreed to pair me with Jane. This way I could end the summer knowing how she felt, how she tasted, and how I could remember her forever. It was expressly forbidden that we peek outside our blindfolds, but I did it anyway. I couldn't resist the chance to glimpse that gorgeous girl's naked figure beneath me. I saw more than just that of course. All the other girls surrounded, each in various states of nudity, either giving or receiving some form of carnal pleasure. If it wasn't clear before that I have an attraction to all humans in this natural state, it certainly was now. But nothing was more of a turn-on than Jane's little rainbow-coloured panties with the star punched in the hip. Watching them drag off of her was like witnessing world class art.

It all worked perfectly except for the fact that I never quite got over Jane. Even after several years went by, and I became quite the sexual adventurer myself, I still thought of her often and wished her happiness and satisfaction. My long con began when I saw her from across a bar, eating a meal with a handsome young man who I thought at first might be her boyfriend, but when she left prematurely and I noticed no kiss between them, I second-guessed myself. My first instinct was to follow Jane out of the bar and catch up for a chat. But too chicken, I stayed and watched the man, and eventually followed him out instead. I lost him after a few blocks of keeping my distance but spotted him again a month later, from across the street as he entered this little stationary store.

After he left I went inside and applied for a job. I suppose the rest can be inferred. I worked there for three months before he returned. Max was his name, of course. I fucked him in the storage room, indeed several times. Like I told Kelly, I always liked boys. Before I could worm my way into Jane's life via Max, I had to assess his sexual openness, so I invited him to meet my friend Annie. I had another friend, Nick, come along too and pretend to be another man for Annie to potentially pick, although he was just a plant, meant to give Max confidence. At that get together, we played Prompt to loosen up the talking. In no time, Max proved to be very open to group activities, although he and Annie only touched each other. I sat aside and pleasured myself while he ate her ass against the glass door, and then fucked her on the couch and came on her tits.

And before I start to come across as a total sociopath, I should be clear that Jane came to me, not the reverse. I was plenty content enjoying her old friend for as long as it took. But I knew she'd be along eventually, and when she came into the store the same way Max had done, I was in her pants even faster. If they thought I was a natural, it's only because they hadn't met Jane. She was even better than I remembered. I knew then that my longing for her hadn't been in vain. But when she let on that she loved Max, I had no choice but to use my gift for social arrangement to bring her happiness. It's like what Kelly had done for me; if we can help someone fulfil their love, we should. Plus, I'd fucked both these crazy kids now, and hell, maybe all three of us could share a round.

We did just that, but not before I let Jane enjoy a practice session with my friends Jessie and Craig, who happened to be her two favourite porn stars. That part I really didn't contrive, but it was another easy sell, and it helped to drive home the fact that Jane was a very dirty girl. First, we tied her up and Craig had his way with her. Meanwhile, Jessie and I stripped down in the other room and warmed each other up (we'd done this so often it was practically like racquetball). Then we joined them on the bed for some daisy-chaining, followed by group-falating, and then a paired-off fuck which required a strap-on that both Jane and I got to receive.

When it came time for Jane and Max to finally hook up, I was honoured to be a part of the scheme. It was a time of necessary rebellion for her. She was breaking free from a bad work situation and a long string of unsuitable suitors. Max was as happy as ever to go along with the wondrous depravity that was continually falling in his lap.

I leaned against the wall of the shower and watched as Jane dropped to her knees and took Max's cock into her mouth. Then some time later, I laid into the sheets and took in the sight of him entering her pussy. They came together like a song, and it was one of the great joys of my life to have played a role in creating that happiness for them. It's among many joys I've felt in their company, naturally. And now here comes another...

Max and Jane decided to get married in the Spring. It was clear they were bonded for life, but because of the circumstances surrounding their partnering, there was never any fuss in their relationship about the constraints of monogamy. They agreed immediately to continue welcoming guests into their sex life. This was particularly good news for me because although my love for Jane had taken on a new meaning, I would always consider her the most beautiful and alluring person on earth, and Max, I'm not sure there's a more capable cock on a more pleasant man anywhere.

With an agreement of openness comes a new series of terms, and an early one was the trade-off that Jane and Max would each have sign-off on each others' bachelor parties. Perhaps not coincidentally, they both hired me as Party Planner. This meant I would be busy indeed, but my history managing people and events speaks for itself, and anyway, I always knew how to make other peoples' plans fun for me too.

The two parties were a week apart, with Max's bachelor happening first at a lake house we rented for a weekend. There was a hot tub and a pool table and a fully stocked bar. The crowd was intimate, with only his five oldest buddies invited. They were Dean, Chris, Shawn, Adam, and Grant - all thoroughly handsome gentlemen who, it turned out, Max had had the decency not to tell about his many sexual exploits. Not that these boys were prudes, but the revelations of the night away were clearly an abrupt shock to all of them.

When I entered the house through the kitchen, the six men were seated around a large sectional couch room drinking scotch and chatting. They all turned in silence and stunned at my pink glittery party dress which cut low into my cleavage and stopped a millimetre below the crotch of my thong. I'd done my hair up in full glamour, and my make-up, which was generally on the extreme side, matched my attire in sparkle and sultry provocation.

"Did someone hire a..." asked Adam.

"Dude, shut up," snapped Shawn.

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Max only smiled at me. He had no idea what was in store, but I could tell he wasn't surprised to see how things were beginning.

"A what?" I asked, affecting a soft tenor.

"Nothing," said Adam, bashfully.

"Were you going to say stripper, sweetie?"

"No, no. Definitely not."

"Oh. Because if you don't want strippers... we can go."

"We?" asked Grant.

"Yes," I confirmed. "We."

On cue, I was joined on either side by my fellow angels. Jessie on my right, wore an identically slutty dress, but hers was black; and Veronica stood at my left, in the dress's white version. Our hair and make-up was done the same, and our heels varied to better even our heights.

As for the other girls, it's worth knowing that Max knew Jessie from her content online, but had never met her before this evening. Veronica, he had met, although never without her mask on. She had appeared in a number of Jessie and Craig's videos as a third-party, and had become a good friend of mine as well. She was twenty, naturally red-headed, and even more petite than me. Her freckles evenly coated her entire adorable body, and in spite of her many singular facets of beauty, she only ever appeared in sexual conquests anonymously. I convinced her to make an exception by saying that there would be a total of nine of us fully naked - masks simply didn't belong.

"Girls, this young man doesn't seem to want us to take our clothes off," I teased. "Maybe we've come to the wrong party."

"What a shame," pouted Jessie.

"I can't believe I got this horny for nothing," said Veronica.

"No, you didn't, you didn't," insisted Dean.

"Please stay," begged Chris.

"Okay," I said. "But Veronica's right. We showed up horny, so before we can get started, we're going to need to see all you guys strip down."

They visibly hesitated at first.

"Come on," instructed Jessie. "Haven't got all night."

"Well, we kind of do," I clarified, "But the faster the better. Hop to it."

All six men stood and began removing shirts and pants. They all seemed to hesitate again at their underwear, and at this point it became clear just how bulging each of them was. The only member of the party unphased by our arrival was Max, who was blithely willing to go along with whatever might occur. Another urge of haste forced them to pull down their remaining articles, and Jessie and Veronica and I finally approached the line of them and stood opposed. I positioned myself between Adam and Dean, Veronica stood between Chris and Shawn, and Jessie filled the remaining spot between Grant and Max. The girls and I had six hands among us, and each of them reached forward and found a cock to stroke.

We revved those boys up to their absolute peaks. Any anxiousness they might have had about getting jerked off in the same room as all their buddies was quickly dulled by the overpowering satisfaction charging through their members. Speaking for my guys, Adam's cock was long and subtly curved; Dean's was thick in a perfect complement. They both throbbed with every pump and I could already feel myself getting excited to welcome them between my lips. The guest of honour looked to be having a stellar time also, having Jessie tease him with the graze of her delicate fingers. He too was starting to lose his cool.

When I began to feel the moisture of a bit of pre-come on my hand affixed to Adam, I announced my next instruction for the group.

"Would you all be gentlemen and help us out of these confining dresses?"

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"Seems like we're the strippers," joked Chris.

"Is that okay with you?" I asked.

"Yes, ma'am."

Dean pulled the spaghetti straps from my shoulders, loosening the outfit. Adam then tugged at the skirt from its bottom hem, and in so doing, grazed the silk against my aching mound. The other four boys performed in similar fashion until all three girls were standing before them in matching bra and thong sets corresponding to the colours of our respective dresses. From the middle position, I turned to Jessie and unhooked her bra, letting her extraordinary breasts free. With my back to Veronica, she was able to remove my bra, and after it hit the ground, I swerved to return the favour but not before leaning in to give her a long and succulent kiss.

We girls faced the line of men and relished the amusing sight of their gaping eyes. Then we lowered to our knees and examined the cocks from eye level. I warmly ran the grip of my hand down Adam's length so he wouldn't feel excluded while I used my other hand to point Dean's dick toward my mouth. Hungrily, I lunged my mouth over him, instantly allowing his tip to crash into my tonsils. I was polite enough to close my eyes for this moment, so I couldn't know who Jessie and Veronica were sucking on first, but the sounds of slurping and moaning made it obvious we were all at a common juncture.

After some preliminary tonguing, I dropped Adam's cock and used my newly free hand to force Dean's pelvis backward until his shins reached the couch and he stumbled into a seated position. I know what I'm doing, so I managed not to let his shaft escape my lips during his fall. Now, over top of him, I was able to drive my face deep into his lap, consuming his cock to the ultimate degree.

I had hoped Adam would intuit what to do next, but I couldn't blame him for needing a little coaching in such a wild environment. Without neglecting my attention to Dean, I returned my hand back toward Adam. I found his cock first, but instead of stroking it again, I guided my hand to his stomach and then up to his muscular arm. Then I tugged at him, aligning his reach downward and forcing him into a crouch behind me. I placed his hand on my ass and before I released it, I pulled slightly at the slim line of silk running between my cheeks, showing off its capacity for stretch. This got the message across. While continuing to deep throat Dean, I felt Adam pull my skimpy panties to the side and line his cock up with my opening. When he made a sleek but confident entrance, filling my insides with his ample unit, I allowed myself a breather, releasing my mouth from Dean and opening my eyes to survey the periphery.

Veronica was fully naked, splayed on the couch with her legs spread and Chris sort of standing and thrusting into her front-on, and Shawn stood by the armrest pointing his cock directly down her throat. Jessie was on the opposite side of the couch, positioned on all fours, sucking Grant's dick and having her pussy eaten by Max from behind. I noted that her black thong was pulled down but not off. The tiny item was suspended halfway between her knees and hips, stretching with the width of her legs. This was so Max, I thought. The man loved pussy, but he loved ladies underwear almost as much, and he never squandered a pair of panties if he could help it. I caught Grant's eye and winked at him as I went to return Dean's cock into my mouth. Grant then leaned forward just enough to high-five Adam, who's hand swung forward above me.

Adam began by rocking my hips smoothly. With each pump inward I gushed at the sensation of his rod colliding with my insides. I respected his right to get going at his own pace, but before long I took some control and sped him up by bucking my lower half backward into his cock at a faster and rougher pace. He met me where I wanted and quickly began fucking me like I demanded to be fucked, like I could tell he'd always wanted to fuck a woman. With each thrust forward, I continued fawning lower onto Dean's thick cock. I knew I tasted pre-come, and he was wincing and moaning just as you like, but I was thoroughly impressed with his ability to hang on. At this early stage of the night, all six men were proving very agile indeed.

I couldn't remember who exactly, but at least two of the other guests at Max's bachelor party were in committed relationships. I was sure to find that out from Jane before I locked in any plans because I wanted to preempt any drama. "They're grown ups," she told me. "Let them make their own choices." There certainly hadn't been much time spent considering things, so it's possible Max's male friends had similar extramonogamistic arrangements as he. Or maybe they had hell to pay later. What was clear was that hedonism would be seized now, and it was heaven for them.

Victoria started coming. "Oh! Oh! Oh, my god! Yoouu'rree huuggee! Keep going!"

As she flung her head back into the cushion, Chris's spunk became visible around her slit. He howled out too and the pair finished coming together before he ejected. Without thinking, I shot up, letting the dicks fall out of my mouth and pussy, and I pounced toward Victoria's side on the couch. Here, I bent low and licked up the sticky, delicious mess left behind. While leaning this way, I felt soft hands peel my underwear down and I lifted each foot so they could be taken off completely. Jessie then moved her face below my pussy and I lowered to sit on her open mouth. There was enough movement coming from her for me to know she was being fucked by someone, but I couldn't see who from where I was. Before leaving this spot, I came hard against Jessie's face and several others in the room reached an audible climax also.

When eventually I dismounted Jessie, I sat upright to get a lay of the land. The six male faces remained bewildered and flourished, but I was thrilled to see no cocks had yet gone soft.

"Honest question," I said. "Who here's fucked a girl in the ass?"

"I have," joked Jessie.

"I know you have," I laughed. "I know Max has too."

"Wait," said Grant. "Max, do you know this girl?"

Max chuckled and nodded. "She's the maid of honour."

The men lit up with a buzz of surprise. "What the fuck?" someone guffawed. Another asked, "Aren't you going to get killed for this?"

"No, I think we have an understanding."

"I'll say you do," said Shawn. "How else would she know you've done anal?"

"Are you a bit jealous, maybe?" I teased him.

"How could I not be?" he said.

"Fair enough. Everyone who promises to be gentle but not too gentle is welcome to have a turn." I reached out a hand each to Jessie and Veronica and I led them off the couch and down to the floor. Jessie tugged off the panties that were still dangling between her legs. We arranged ourselves on the rug in a three-pronged star-shape, with our faces all together and our asses stuck out in different directions. The three of us began making out. There would be no further direction. It took only a moment before a cock found each of us, and by process of elimination, I could surmise mine was Shawn's. I had the most perfect view of Max fucking Victoria's ass, and Dean fucking Jessie's. The other three men looked on awaiting their chance.

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