My Sexual Adventure Ch. 05

Warning: The following is a work of fiction, no one in this story is real. I've loosely based some of the characters on my favorite porn stars, to give you a reference point. All characters are over 18. Like before, I appreciate any kind of feedback on possible improvements.

Chapter 1: I learn how to have sex, from an expected source

Chapter 2: I start exploring my sex drive

Chapter 3: I decide to host a sex party

Chapter 4: The After-party

Chapter 5: What happens in an Orgy, MUST be repeated elsewhere!

Chapter 6: A long awaited climax!

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A couple of days after Annette came by and participated in our poolside orgy, she returned with four contracts that we had to sign. The contracts were for a five-year plan where we'd agree to participate in at least three videos over the course of our time with Seductive Swingers United. It also said that we'd get 30% of all grossed profits from each video sold, ranging from five to $10,000 each, and we'd receive direct deposits of our paychecks within two months of the video's release. After looking over the contract and confirming with my mom that it was the same one that she signed, we all agreed and signed our names on our copies. Annette smiled as we shook hands and she got to her feet and began to strip.

"We like to end our deals with a good fucking so that our newcomers know what is expected!" She said to us as she tore off her panties and knelt down in front of me and Adam, pulling our pants down with her. Taking out our cocks, she quickly sucked on mine while she rubbed Adam's. Then, after a few minutes took my cock out of her mouth and took in Adam's. This went on for several minutes, all the while Kelly and my mom had stripped off their clothes and now laid on the floor, fingering each other while they watched

After switching between our cocks for about fifteen minutes, we both climaxed onto her face, and she sucked up our cum with great satisfaction. She then crawled towards my mom and knelt down, taking her pussy into her mouth. She also held her hand out and started fingering Kelly's pussy as she sucked mom. The three of them released moans of pleasure as Adam and I put our hands on each other's dicks and started rubbing them to full hardness. Once we were completely erect, I knelt behind Annette and pushed forwards, while Adam stood over Kelly and pushed his cock into her mouth.

As I fucked her, Annette gave extra attention to mom's pussy until she started screaming in orgasm. Annette then lifted her mouth and brought her tongue to my mouth, kissing me and sharing mom's pussy juices. As we broke the kiss, she knelt back down and took Kelly's pussy in her mouth, just as Adam came in Kelly's mouth and had switched his cock over to mom's mouth, who took it without question and began to clean the excess cum off. I continued to fuck Annette from behind and, upon her insistence, started spanking her ass as I did. Each time I spanked her, she let out a yelp and sucked Kelly even faster until Kelly screamed and let out an orgasm all over Annette's mouth, which by the sight of it all, sent me over the edge as well!

Spent, I pulled out of Annette's pussy and got to my feet, presenting my cum ridden cock to Kelly to clean up. As Kelly licked me clean, Annette got to her feet and kissed me deeply and passionately. After she broke the kiss, she patted my ass and whispered in my ear, "You are way better than your father ever was!"

She then turned to my mom and said, "You should be proud of your son, Libby. Or is it Alison now?"

Mom smiled as Adam pulled out of her mouth, "It's always been Alison, though it felt good to hear the name 'Smutty Libby' again." she said, as she got to her feet and walked over to Annette. With a deep breath, she took Annette in for a slow kiss. When the broke, Annette smiled and said, "You know, the Generational Orgy is coming up in a month. If you want, you and your family can join. You could even bring along your fuck buddies if you're interested."

Mom smiled and looked at me, "I think we can do that! If we have time!" she said, grinning. Annette smiled again and gave me a quick kiss on the lips before stooping down and gathering her clothes. Without another glance, she strutted out of the house, stark naked, her clothes over her shoulder, and left. When the door closed behind her, I turned to mom and asked. "What's the Generational Orgy?"

Mom smiled and explained that the Generational orgy was an event that Seductive Swingers United did every ten years or so. It was a massive orgy where new members in their twenties come together and fuck existing members in their thirties and forties, who are current or former members of the company in a massive party that lasts four days. During the four days, Members have their choice of any member they want to fuck, in any way possible, and that the entire thing is recorded and released as a pornographic movie.

After hearing all about the Generational Orgy, I was completely convinced of the idea and suggested we take part. Kelly and Adam agreed, and with that, mom nodded in agreement and told us to call our friends to see if they would be interested as well. Upon hearing about it, they all agreed as well, so we called Annette. She told us that the Generational Orgy took place in Las Vegas, and said she'd send us a private jet. She also told us that Seductive Swingers United was located in Vegas, so we'd be able to take part in our first videos around that time as well.

It was early August when all ten of us boarded the flight to Vegas, and as we boarded, we were greeted by an awesome sight, the flight attendants were nude and very sexy looking! There were six in total, three guys, three girls. Each of the attendants wore nothing but a flight attendant's hat, cuffs and a bowtie. All the males were ripped and had matching dicks of 7" and were nearly hairless. The women flight attendants consisted of a blonde, a brunette and a redhead, who had different features and varying breast sizes.

The blonde had neck length hair and d-cup tits, which looked like they were implants, and a shaven pussy. The brunette had a tiny triangle of hair, but was otherwise shaven, and had c-cup tits, and the redhead had double-d tits and was completely hairless from the neck down. the males' hair were slightly different, where one was blonde, the second was dirty blonde, and the third was dark brown.

The plane itself was a marvel of comfort. There were couches made of leather, the floor was carpeted with a very soft fabric, and the walls were lines with a tiger's strip pattern. There were also four large screen TVs along the walls, and the viewports had shades of nude models over the plastic covers. Once everyone got settled in the plane, the redheaded flight attendant told us we'd be leaving soon and said to get comfortable, that there was alcohol in the back, porn movies and magazines in the cabinets, and that she, along with the other attendants, would be at our disposal in case we needed anything...and she meant anything, as we soon learned why.

As soon as we were in the air, the attendants brought us refreshments, and after we each had a drink in hand, the women knelt down and leaned forwards and pulled out our dicks and started sucking, as did some of the male attendants. All five of us guys moaned in pleasure as we got our cocks sucked by what was obviously expert cock-suckers For five minutes, I was being sucked by the redhead, then out of nowhere, they switched and rotated, and the blonde sat down and started sucking. She lasted another five minutes, then the brunette had a go, then the blonde guy, then when the dirty blonde male attendant got to suck me off, I barely lasted his mouth and came into the fourth minute. All the guys lasted around the same time and came shortly after.

The dirty blonde male held on but didn't swallow, got to his feet and shared my load with the dark haired attendant. The dark haired kiss his fellow, then broke the kiss and leaned forwards and kissed me, sharing my cum. I kissed him hard, then looked around as the attendants switched from the guys to the girls, taking off their pants and licking their pussies. They repeated the process, one person licks for five minutes then switch until someone came, then they sped up the process until they all came. After the girls came, Amber, Linda and Kelly grabbed one of the male attendants and started kissing them, as they took their cocks in hand and guided them to their pussies. The male attendants smirked as they entered the girls and fucked them hard.

As I watched, I noticed that the blonde and redhead flight attendants had mounted Anthony and Jeff, and were now bouncing on their cocks while Mark was ramming his up the Redhead's ass, and quickly switched to the blonde, after a dozen or so thrusts. Thinking quickly, I nudged Adam, then went up to the brunette, who was in a 69 with my mom and quickly entered her from behind. Adam took the hint and began to thrust into mom's pussy from above. As we fucked, Zoe came over and bent over my face, allowing me to lick her pussy while I fucked the flight attendant, who was moaning and kept asking me to spank her, which I quickly obliged.

After a few minutes of non-stop fucking, licking, and spanking, I came inside the flight attendant just as Zoe came all over my face. Pulling out of the flight attendant, I stood up and presented my cum ridden cock to Zoe, who quickly took it in her mouth and sucked it until I was hard again. I then bent her over one of the couches and entered from behind, ramming her with twice the speed I had given the flight attendant. She screamed as I fucked her hard, and like the second time I fucked a girl, I lasted half as long and came twice as hard. Afterwards, I sat down and Zoe sat beside me, spent as we watched the orgy before us, gently massaging each other's genitals in the process.

Kelly, Amber, and Linda had stopped fucking the three male flight attendants and were now licking the cum out of their pussies as the male attendants were now in a circle jerk with Anthony, Jeff, Mark, and Adam. The blonde and redhead flight attendants had joined the redhead, my mom and Adam, who was now on his back, having mom and the redhead hover over his head, where he sucked on their tits and switched between them, while the blonde and brunette flight attendants took turns sucking his cock and balls.

After a while, Zoe and I started getting aroused again, and our vitality soon returned, so we got up and joined the two groups, I went over and presented my cock to the male flight attendants, who had switched from a circle jerk to a spooning daisy chain, and plunged my hard-on into the dark haired one, who by now was fucking Anthony. Zoe went over to Linda, who began sucking her pussy while Zoe licked Kelly's tits. The ass I was fucking was tight, but as soon as I kept up my rhythm, I was enjoying the male flight attendant very much, as he leaned his head around and kissed me deeply. All of a sudden, someone came up behind me and pushed a large 10" dick in my ass. I looked behind me and saw the pilot.

I almost jumped out, but the dark haired flight attendant told me that the private jet had autopilot, so the pilots probably hit it to come and join in the orgy. I grinned as I watched the pilot strip off his uniform while still fucking my ass. I was impressed by his body; he had a ripped physique with a little bit of chest hair, and tan skin. I think he was Greek in origin, and he was at least 6'2" tall. His dick certainly felt good, as he continued to fuck me wild. I looked around and saw the co-pilot hovering over Adam, pushing his 9" dick and fucking him while the flight attendants had switched the his cock and ass. the co-pilot was slightly shorter than the pilot, ranging at about 5'9".

The two of them lasted only minutes, then got to their feet after we felt a little rumble of turbulence, and strolled nude back to the cockpit. I assumed that the auto-pilot wasn't meant to be on during turbulence, so they had to go back and fly the plane. Since they were both still nude, I imagined that once they had settled back in their seats, they would be rubbing each other's bodies and cocks all through the remainder of the flight. All of a sudden, the redhead flight attendant and my mom got to their feet and walked towards the cockpit, closing the door behind them. Shortly afterwards, I heard moans through the door and knew my mom was servicing the pilots like a pro!

I looked over at Adam, who had flipped the blonde and brunette flight attendants onto their backs and started fucking one, then the other after a few thrusts, and I quickly disengaged from the dark haired flight attendant and moved over to them, knelt down and entered the blonde, who squealed as I pounded into her. Once Adam and I got into sync with our partners, the flight attendants started kissing each other, and Adam and I decided to do the same. We leaned in and kissed passionately, then broke our kiss and knelt over and kissed our flight attendants.

I then had an idea, so I told Adam and the attendants, who then went and spread my idea t everyone else, who then dislodged from each other and formed my new position. All the women got into a head to toe pattern, then all the guys mounted one of them, and started fucking missionary style. Unfortunately, the line-up came up short, since mom and redhead flight attendant wasn't with us, so I quickly went to the cockpit, opening the door to reveal mom and the flight attendant in a 69 position while the pilots got blowjobs in their seats. I cleared my throat and told mom the attendant what we were doing, so they quickly disengaged, kissed the pilot and co-pilot, and followed me out, getting into position. I then entered mom while the dark haired male flight attendant entered the redhead, and we proceeded.

For ten whole minutes, we all fucked our girls in our head to toe, all the while leaning forwards to kiss a neighbor, suck a tit, or cop a feel elsewhere. Then we each got to our feet and found a new partner, and repeated the process. Eventually, once one or both a guy and girl came, they would leave the group and head off to one of the couches or into the corner, where they would watch the rest of us, until there were only two left. I had told everyone to fuck at the same pace, but I was intentionally fucking a little slower than anyone else, so that I would be the one who won.

Once it was down to Me, the dirty blonde male flight attendant, Zoe, and the Blonde flight attendant, we didn't hold back, as I fucked the flight attendant like there was no tomorrow, as did the male flight attendant. Our two partners squealed like there was nothing more erotic and stimulating, and at once, the four of us came together in a sea of cum and sweat. Exhausted, we collapsed on top of each other, and I smiled as we all knew that the four of us had won collectively. We all leaned forwards and kissed each other and I kindly asked for the names of my fellow victors. The dirty blonde male was named Victor, and the blonde was named Emily.

Over the next hour, everyone relaxed in the nude as the flight attendants brought us drinks, sex toys, magazines, and we all watched a lovely orgy video while gently fingering and rubbing each other's bodies. I soon learned the names of the other flight attendants. The redhead was named Erin, the brunette was named Sue, the blonde male was called Ollie and the dark haired male was called Joe. As soon as the final stretch of cum was flying in the movie, the pilot opened the intercom and said that we'd be landing in Las Vegas shortly and thanked us for a wild flight. Everyone smiled and laughed as we kissed one another one last time and gathered our clothes for the landing. Everyone except the flight attendants, that is!

Once we landed, we were escorted to a black stretch limo that was marked "Seductive Swingers United Co.". We got in and were driven to a large casino and hotel. Upon entering, we were greeted by the most awesome sight. Everyone in the hotel was nude! There was a sign by the entrance that read "Welcome to the Seductive Swingers Hotel. While staying here, we encourage all our employees, guests, and future participants of Seductive Swingers United to enjoy our facilities in the nude, to offer a well mannered environment. Warning, all sexual activity must be consensual, under penalty of immediate dismissal! WE DO NOT ENCOURAGE RAPE OF ANY KIND!"

Once everyone read the sign and nodded that it was a fair bargain, we went to the front desk to sign in, and I was surprised that Annette was behind the counter. She smiled at us and gestured us to follow her into the elevator, which was completely transparent. Once we entered, she knelt down and took my pants off, revealing a hard-on, and started to suck it as the elevator ascended. I lasted a few minutes before cumming in her mouth, just as the elevator stopped at the top floor. She swallowed my cum and got to her feet.

"Welcome to the Company's hotel, we're happy to have you here," she said, winking at me as a small amount of my cum seeped out of her mouth, "We've reserved the best suite in the hotel for the ten of you. I hope you enjoy!" and with that, the elevator doors opened to reveal a wondrous sight! The hotel room we were in was a massive penthouse with unending sex toys, bondage equipment, stripper poles, an in-floor hot tub, small kitchen, massive vista, leather couches, a giant flat-screen TV, and five heart-shaped beds along the walls. There was also a door leading to a massive bathroom with three showers and a large circular bathtub. We also noticed that the room had mirrors on the ceiling, so we could watch ourselves fucking any time we wanted.

Annette told us that the hotel had a large indoor pool, spa, workout center, casino, dance floor, restaurant, and porn theater, and that the staff were filled with porn stars and paid companions, all of whom were bisexual and willing to fuck on a moment's notice, and that we were encouraged to entertain ourselves at any point during our visit. We all thanked her and as she departed, we all shucked our luggage to the side and stripped nude at the same time. Now completely naked, Anthony, Jeff and Mark left the room and headed down to the pool, taking towels from the bathroom and linking their key cards to neck chains. Linda, Zoe, and Amber also left, heading down to the spa.

As we watched them leave, I quickly grabbed Kelly and mom and dropped them onto one of the beds, quickly mounting mom as soon as she hit the mattress. Adam came up next to me and mounted Kelly at the same time. Our women moaned as we started to thrust and exchanged kisses and tit grabs. We fucked for several minutes before Adam and I pulled out and swapped pussies. As I entered Kelly, I leaned forwards and kissed her deeply, and whispered how much I loved her. She returned the favor by kissing me hard and whispered she loved me back. As soon as I heard the words, I came inside her hard and fast.

Lifting my head as I came, I saw that Adam was now fucking mom's ass from behind and she was howling like a wolf to the moon. He howled back as he pulled out and grabbed my neck, pulling me down to his cock. I took him in, sucked him clean, swallowed his cum, and lifted myself to full height, getting off the bed and grabbing my clothes. The three of them watched me dress, then asked me where I was going.

"I looked it up online where to find a Jewelry store in Vegas before we left. I still haven't gotten Kelly and engagement ring yet!" I told them as I slipped my pants up. Adam smiled as he too got off the bed and grabbed a pair of shorts. Kelly and my mom looked at each other, then looked back at us and said they didn't need engagement rings, that we'd go buy rings after getting married, since we'd be able to afford them with the amount of money we'd receive from the porn movies we would be doing. I quickly smiled and dropped my pants, walking over to Kelly and my mom, kissing both on the lips.