Grandfather s Cock Orgy for Eight
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My New Career Part VI, An Orgy On The Lake free porn video
For the first time, my life had leaked into my secret porn life on a side job that paid very well. I must admit that side jobs are a huge turn on for me.
I do so love to be fucked and get off on the fact that men pay to fuck me. In addition, they pay to watch videos of me fucking. It keeps me in a constant state of whoredom.
An “investor” had hired me to be the entertainment for his son’s bachelor party. He also paid to have me in a one-on-one for himself. When I met him at Mr. Malone’s studio, it turned out we knew each other socially. However, Mr. Malone made it clear that bad things would happen if Mr. Smith ever used this info in our social lives.
I must admit there were many reasons I enjoyed fucking Mr. Smith’s overweight body and short fat cock, not least among them was I couldn’t stand his wife.
After finishing with Mr. Smith, I readied myself to go on Lake Michigan and be fucked silly by five young men, all horny for “Lynn the MILF." I knew I wouldn’t need many clothes so all I wore was a very transparent white monokini and a matching transparent cover. Even dry it didn’t leave much to the imagination. Plus five-inch fuck-me heels.
I hopped in the limo that had been arranged and was whisked away to Monroe Harbor in downtown Chicago. I was given the slip number and Mike my driver dropped me off. I then went down the dock to the cabin cruiser we would be using for the day. Mike went with me to make sure I arrived alright and the boys knew the rules.
It was a sixty-foot cabin cruiser by the name of Flying Lady, a rather infamous yacht. It even had a stripper pole built into the aft deck. The Flying Lady was a staple of the floating parties on Lake Michigan at the Playpen. The Playpen is well known as an area on the lake where boats would gather for fun. I was impressed.
Mike asked the ship captain's permission to come aboard. He took me to meet the captain. Mike told me he did a lot of work for Mr. Malone and he would look out for me. Then Mike led me to meet the boys.
They were all eyes on me. Mike finally gained the boys' attention as I went to get a drink. I heard him instruct the boys that they could do whatever they wanted but if I said no... it meant no. Outside of that, anything went.
Once that was done, Mike excused himself and left. The boys immediately came into the inner cabin to the bar I was at. They began to introduce themselves. Cal Smith was the guest of honor, so I made a point of remembering him. He was built a lot like his father, a bit short and pudgy. Oh well, I have fucked worse.
The four others introduced themselves. Two were cousins of Cal, named Rich and Seth. The other two were quite interesting. Atlas, a six-foot muscular Hispanic. I was drawn to him, he was brown and built. The last one introduced himself. He was Lucas, but his accent got my motor running as much as Atlas. He was Australian.
Either one of those two, I would fuck in a heartbeat. We felt as much as heard the yacht's engines start. We all had drinks, so we headed to the aft deck. The boys wanted to make sure as many of the people in the harbor as possible saw I was with them.
I flirted with all the boys, paying special attention to Cal but kept my eyes on Atlas and Lucas. I would then wave and prance for men on other boats. The boys' chests puffed up at being with me. Hands were on my ass, around my waist, any which way they could on my breasts, etcetera. Atlas put on some music.
I will be honest, I had no idea who it was. It was their music. However, I can dance to anything. So, I started dancing for Cal. A bit of dirty dancing. Friction from our bodies rubbing and grinding began to grow. I will admit it was turning me on. Especially knowing I would be fucking each of them soon.
Soon we were clearing the docks and heading to the Playpen.
I was mainly dancing with Cal, then sandwiched between Cal and taking turns on of the cousins. Then the other two. Rich and Seth were enjoying themselves humping my ass. Putting my hand on Cal’s shoulder I spread my thighs a bit, grinding on his thigh. Seth humped my ass.
The chubby rich boys were enjoying themselves. I was finding myself turned on by the kinkiness of two boys barely legal to drink pressing me between their pale bodies. However, that was nothing compared to how wet I got when sandwiched between Lucas and Atlas.
This went on until a bit after we neared the floating party at the Playpen. Soon hands were roaming up cupping my breasts. We were going to be out here until the wee hours of the morning. And even with the fact they were young and probably would be able to cum many times over, my mentor Gina instructed me to tease them and get them all horny.
The captain appeared and had a word with Cal, but I heard. He asked if he wanted to be tied up with the other boats. This would allow the fun of boat hopping. However, it would make it hard for them to enjoy the many attributes I brought to the party personally. Cal decided to have the captain anchor us about twenty feet away from the main group. The boys wanted to make sure they were the envy of the other boats but could still have the privacy they needed for the main events later.
I started dancing from the pole giving the boys a show. Several other men and a couple of women from other boats were all cheering me on. I was spinning and then grinding on the boys, then finally let my breasts come out of the monokini. The transparent cloth was on the outside. My huge 36 DDs were tan with no lines. There were dark inch wide aureoles and quarter-inch long stiff nipples. It was a couple of songs later before I let them start playing with them.
I was shaking them for the audience twenty feet away to their cheers. Then as the next song started, I shrugged off the shoulder strap, now completely topless. I moved from lap to lap. I paid extra attention to Cal but enjoyed Atlas and Lucas more. I was trying not to let it show, though.
It was early in the afternoon, hot sunny and humid on the lake. I had worked up a nice sheen of perspiration which I enhanced by letting Cal rub tanning oil onto all exposed parts of my skin. I was still going from guy to guy getting them all worked up and constantly hard.
After a while, I decided some drinks would be a good idea. I needed to hydrate and wanted them to keep a good buzz going. We were all sitting on the aft deck around the pole when a ten-foot zodiac boat pulled up. It had two rather hot enhanced girls on it. Both were extremely hot and oozed sexuality. One was African-American the other Asian. It wasn’t a great leap to assume they were strippers by profession. They asked permission to come aboard, more out of the need for help than the etiquette of the sea.
I had to chuckle to myself at Cal and his cousins were goggle-eyed at all that was there. Lucas was a bit more composed and Atlas handled it in stride. The women barely acknowledged the boys and approached me.
“Are you Lynn the Milf from Malone Studios?”
I had to admit that threw me that they knew who I was. They introduced themselves as Tiffany and Jasmine. I was even more aroused being very obviously sized up by these two exotic ladies and knowing it would only spur the boys on to fuck me harder. I was sitting topless in the middle.
Cal’s rich boy arrogance came to the front as he had enough of the drink to get bold. “Ladies, just so you know Lynn is with us. It is my bachelor party. You are welcome to stay and enjoy our booze and food, but I must insist that you do not wear more clothes than Lynn. Seeing how she is topless if you would like to stay... ” and he left it hanging.
The girls were a lot more streetwise than Cal. Some negotiations ensued. In the end, what they wanted was to have some photos and videos with me for their portfolios. (I didn’t even know strippers had them). If I was willing and it was ok with everyone, they would give the boys a show they would never forget. Cal barely beat the other boys in agreeing.
Instead of taking off their tops, Jasmine, the stacked Asian beauty looked at me. “Well, Milfy get to work! Take our tops off for us.”
She ordered in a total change of persona. I was not sure if Cal would go along with it but something in me clicked and not giving anyone a chance to stop me, I was at her in a flash, undoing her bikini bra. Tiffany came over and kissed Jasmine as I was doing that.
She broke the kiss long enough, not even looking back at me. “Now get Tiffany’s,” which I did. They then turned to me. Tiffany pressed her ebony body and firm breasts to me as Jasmine moved behind burying her face into my neck. I groaned lost in the moment when suddenly Jasmine slapped my ass hard.
This caused an eruption of, 'oohs,' and, 'oh yeas,' from the boys. “Spank her again,” so she did. The girls must have watched my movies more than the boys. I was turned around and found myself kissing Jasmine as Tiffany played with my now tender ass. Her hand then slipped around to my front playing with my breasts.
The girls were experts and working horny males. “OK, bachelor man. Want us to get her naked?” As they roared yes (as well as a few men from boats around us), “It is your party. Tell us what you want.”
“Strip her. STRIP HER." They obliged, pulling down my suit, leaving me in heels only.
Jasmine kissed me hard her hand feeling my shaven super wet pussy. “Now strip us, Lynn.” I gladly obliged, shedding them of their bottoms.
The three of us, in heels only, started dancing for the boys. Sometimes one of us on a lap sometimes two. For Cal, he would get all three of us. Then it was time to start pleasing Cal. I kneeled between his legs. While staring up into his eyes, I pulled his cock out of his cargo shorts and began stroking him, moving in taking his short chubby cock into my mouth. Moaning as I let it slide down my throat.
Tiffany leaned in and pulled his shirt off from behind. Her breasts pressed to the back of his head her hand teasing his nipples.
I heard some. oohing but didn’t think about it, just thinking it was because of the show Tiff and I was putting on. Suddenly Cal grabbed my head holding me on his cock. I felt a cock entering from behind as hands grabbed my hips. Fingernails dug into my flesh and it dawned on me, it was Jasmine. She had gone back to her dingy and put on a strap on.
I groaned deeply onto Cal's cock as his eyes were bulging. Tiff came around to the front and started sucking his cock with me. I switched down to his balls as Jasmine picked up the pace fucking me. I was very close to cumming, but professional pride made me want to have Cal cum first. Sure enough, a minute later he moaned he was going to.
He gasped out he wanted to cum on my tits. I sat up straight. Jasmine still in me from behind. Cal stood up with Tiff jerking him off and spewed his first load onto my tits.
My two new friends wasted no time in licking me clean. The cousins wanted to be next. I had them stand on either side of me. Taking one in each hand stroking them then turning my head switching from one to the other. Jasmine and Tiff worked their balls. They blew quickly and all over me.
After that my new friends cleaned me up. I had started to look to Atlas and Lucas but Cal had recovered and was ready for some more attention. His selfish attitude rubbed me the wrong way. Those two were his guests as well but he wasn’t being a good host. I chuckled to myself when it hit me that I was upset that he wasn’t sharing my body with them.
It didn’t dampen my annoyance with him. If I had been simply cheating on my husband, I would have ignored him and fucked the built Mexican and the exotic Aussie but since he had paid for me, I bent to his will.
I gathered my two helpers from the cousins. They giggled that Rich and Seth had each paid a thousand dollars to spend the rest of the afternoon with them once we were done with Cal. I lowered myself to all fours and crawled to Cal. I knew the spoiled rich boy would really get aroused at a hot MILF doing that for him.
Having nailed his reaction, I saw his cock stiffened more. Without hesitating my mouth went straight to his cock taking him in and deep throating him. Tiff and Jasmine stood to either side of him each holding a bottle of booze. I don’t even know what kind but as I suck him they would alternate pouring whatever they held down a boob and he lapped it up. He was getting smashed very quickly. He also became a lot more demanding and quite a bit meaner when drunk.
Suddenly he barked out in a slurred voice, “I want your ass, Lynn. Get on all fours.”
Before I did that, Jasmine still wearing her strap on whispered something to him. His grin was one that would be straight out of a Christmas morning. Jasmine went to the pole stage and laid on her back, and beckoned me to mount her. The sight of the big titted Asian goddess with a huge cock was all I needed. Straddling her I sank down moaning. I bent and kissed her our sweat-slicked boobs mashing together.
I was expecting Cal to enter my ass, but instead, I felt liquid dribbling down between my ass cheeks and over my asshole, stinging slightly as it did. I spied Tiff next to me pouring from her bottle. Just then I felt a tongue probing my ass licking up. I started moaning, not having to fake it as it was feeling incredible to a nympho like me.
I started humping Jasmine's cock. I am not sure how much booze Cal slurped up, and I really didn’t care. I was close to orgasm when suddenly he stopped, and I felt his cock head pressing my little brown hole. At this point, he was too drunk and too self-focused on his pleasure to think of how it felt to me. This would be a hard and fast ass fucking, and it didn’t faze me a bit.
I was so horny I just wanted the second cock in me. My wish was granted when he rammed it into me. As I expected one hard thrust. A throaty groan burst from my mouth. Jasmine and I adjusted our pace to his. About to explode, I began to tense up. Without warning, Cal's open hand smacked my ass cheek with a sharp crisp noise. That did it. I shrieked in a loud primal scream.
Cumming, so hard I was seeing stars, I sat up abruptly almost knocking Cal onto his ass. My back arched as I let the whole party area know I was cumming. At this moment Jasmine decided to get in on the act and slapped a breast. I love this more than my ass spanked. I kept cumming and started squirting onto Jasmine's rubber cock.
Suddenly Cal pulled out of my ass with a pop. I felt hot gooey jism spraying my back. Cal was grunting almost incoherently. I continued humping Jasmine through the entire cum shower. Suddenly I felt about two hundred pounds of doughy flesh collapsing onto me. Cal had passed out.
I rolled my sweaty body off Jasmine causing Cal to roll off me. We looked at him and knew we girls couldn’t lift him. I didn’t want to leave him in the sun to get sunburnt, though I was tempted. Before I could think of an answer Atlas and Lucas picked up his soft limp body and took him inside. Tiff went to Seth as Jasmine went to Rich. Neither had made a move to help their cousin. They went inside to do whatever they had negotiated.
I went to the back of the boat and lowered myself into the lake to clean myself off, much to the cheers of other boaters.
As I started up the ladder a large hand extended to me. It was Atlas helping me up. As I made it to the deck, I kept right on going into his arms. Winking at him. “Would you two like to join me for a drink?”
I was curious about the two being left out of everything. Well, the truth is, I found them to be the most fuckable. We went inside to the bar.
While there we could hear the cousins in one of the bedroom cabins being shown a great time by my new friends. Once the drinks were made, I took my two boys out to the aft deck again. I hopped onto the pole and danced a few songs for them. Then I gave them a few lap dances. I then plopped down between them.
I kissed one then the other. I had only my heels on now. Lucas, with that sexy Aussie accent, pointed out that I should put some oil on before I burned. I have a deep tan with no lines, but he was right. I handed him the bottle and went to the stage and laid on my stomach. The sweetheart started with my feet. Of course, he could just have a foot fetish.
As Lucas worked his magic, and he was talented with his fingers, I looked at Atlas and asked what the deal was between the rich boys and these two I was with now. I felt Lucas stop momentarily and could feel the two of them exchange a wary look.
“Don’t worry, I am here because Cal’s father paid a lot of money to have me here. Not because I like them. They are the type that gives my kids a bad name.” He looked confused.
“Don’t get me wrong," I continued, "I like fucking for money but outside of my disastrous poker debts I don’t need the money. My husband is as well off as Cal’s father, but he worked his way up the ladder. He had an ROTC scholarship to go to college. He then made the cut for pilot training and qualified for fighters. He flew F-16s in the Air Force during the First Gulf War. An eye issue grounded him. He went to work in the private sector and is now a VP for a major corporation based in Chicago. My two sons both enlisted in the military, my eldest is a Cav Scout. He spent a year in Afghanistan. My younger is still in the Navy on a submarine at sea right now. I don’t like these trust fund babies at all!”
Lucas was working my ass by this time. I spread my legs, so he knew to work it everywhere. I could almost feel his fear as he rubbed the oil between my ass cheeks. When I felt his fingers about to touch my asshole, still a tad sore from the hard-fucking Cal gave it, I pushed up onto his finger. Hesitating slightly he pressed on it again. I moaned. He continued but much bolder. As he worked up, he gave extra attention to my side boobs.
“Well?” I pressed Atlas. "What's you guys' stories?"
Atlas explained that he was a driver and general gofer for the Smith family. He hesitated a moment, but apparently, a naked hot milf porn actress alternating staring between his eyes and his crotch overcame some discretion. He told me that Cal has very few actual friends, he and his cousins could barely stand each other. Mr. Smith had wanted Atlas to come to make sure Cal didn’t really “step in shit” but also so it wouldn’t look like he was the ass he really was.
He stopped for a moment as Lucas worked my shoulders and neck. Looking at Lucas as I flipped onto my back, I winked. “You’re not done!” He didn’t need to be told twice. Starting from my feet again. “What about my sexy Aussie masseuse?”
Having figured out I was genuinely interested, Atlas didn’t hesitate. “He is in the states studying at a university in downtown Chicago. He is Mr. Smith’s Intern, and is here for the same reason as I am.”
“So just hired help?” Atlas looked a bit wary thinking he had walked into a trap. I smiled.
Lucas was working my upper thighs. I sidled up to the side of the stage, so my head was hanging off of it. As I was looking at Atlas upside down, I spread my legs for Lucas. I mean I really spread them for Lucas. He was a smart intern and went to work on my shaven pussy with his oiled-up hands. Not that they needed to be oiled.
Then grinning at Atlas I said, “We hired help have got to stick together.”
I reached out to him, tugged at his shorts as that was as far as I could reach. He got the hint and stood up, crotch at my face. Unzipping him out flopped his semi-hard brown cock, already twice as long as Cal's and it was only semi-hard. Lucas took this as a signal and stopped with his hands and started with his mouth on my pussy.
Atlas grinned. “I have seen your movies and know you can handle it.” He, of course, was referring to his cock. Well, I can’t let a fan down. I opened wide, head tilted back. It was an incredible feeling as it slid down my throat. Here was a young man who knew how to use his cock as well. He was beginning to fuck my throat.
As he did this, I started my hips grinding on Lucas’s face. Suddenly, I felt Lucas stop working on my pussy, I couldn’t see why or what was happening because I had the most wonderful view of a pair of heavy brown balls. A moment later my distracted puzzlement was answered. A hard cock entered my pussy. Lucas had taken the initiative to fuck me.
Lucas also had a much larger cock than the cousins. He also was a conscientious worker. While fucking me he had poured the bottle of oil on my chest and worked it all over my breasts. However, it could be he just wanted me oiled up under him. It only took a few minutes for yet another orgasm to build up in me. Screaming onto Atlas’ cock I exploded harder than I did before. I had a spasm, unable to control myself.
My two lovers didn’t slow in the least. When I regained control, Atlas pulled out of my throat saying, “Let's switch.” I guessed Lucas had no problem with it because the next thing I knew Atlas was picking me up and putting me down on all fours facing Lucas.
Lucas grabbed my head and guided my mouth onto his cock as Atlas held my hips and he had no trouble finding my opening. As if a signal was given, they both thrust simultaneously. Going in time they kept fucking me. Atlas was torturing me. As he began working his cock in and out of me he would bring me to the edge of orgasm then back off. Then build me up again.
Not only was he built and hung he was very talented. Lucas, on the other hand, was enjoying himself using my mouth as a cock sleeve. A few minutes later, he spewed down my throat. He sat back on his haunches panting. All of us were sweaty and oily. Atlas slowed down a bit but he kept fucking me.
Suddenly we heard applause. It didn’t stop Atlas, he kept pumping. It was Jasmine and Tiffany. Atlas did have the presence of mind to ask if the cousins were ok. The girls laughed. “They passed out,” Jasmine added, “or we broke them.”
Lucas was still semi-rigid. Jasmine kneeled on the stage next to him and took him in her mouth and sucked him up and down a few times. Then releasing him she purred, “You taste good,” and kissed me. “Can we borrow your Aussie friend?”
With a nod from me, Lucas looked like he just won the lottery. Going from fucking a hot milf to two strippers. Grinning from ear to ear he went back inside with them. Personally, I love sweaty sex and an audience turns me on. I also was very attracted to Atlas and his huge cock. I looked over my shoulder at him. “I am all yours, baby.”
His thrusts were smooth and deep keeping me on the edge. An occasional slap on the ass, bringing me close, then backing off, driving me insane. “Oh, shit please make me cum!” I moaned.
“Beg for it, Lynn.”
“PLEASE make me cum!”
“You want my Mexican cock to get you off then REALLY beg for it!”
He knew how to work a woman, “OH SHIT, yes fuck me! Fuck my slutty white pussy with your big brown cock!"
The boats around us began cheering. He spanked me.
“I don’t believe you.” Another hard spank.
“Oh, baby, please make me cum and I will do whatever you want. Please, Atlas, make me explode.”
He pulled out and teased my pussy with his cock head. I tried to push back on to it but he managed to keep it just barely touching.
“ANYTHING, please!”
Suddenly he thrust while gripping my hips and pulling. A loud sharp smacking noise echoed caused by his hips hitting my ass. Only to be drowned out by my gurgling incoherent growl. Suddenly I was having yet another hard orgasm. Without missing a beat or pulling out he used his strength and coordination to pick me up and turn me onto my back. Flipping my legs up and around in front of him. I felt as if I had been screwed by a screw. (Okay bad pun.)
Just like that, I was on my back. He was on top of me using his rod to spread my pussy again. In a flash, I had my legs wrapped around him and he was thrusting. If my head wasn’t spinning from orgasms and impending heat exhaustion, I would have complimented him. Instead, he kept thrusting in and out of me.
“Tell me to cum in you,” he ordered.
“Oh, fuck, baby. Cum in me. Fill me up.”
With one last powerful thrust, be buried in me deeper than before and shot. I actually felt stream after hot stream of jism filling me. Still hard and in me, he laid on top of me. “Remember you owe me!”
As much as I like hot sweaty sex I felt as though I was close to a heat stroke. I suggested we head into the bar in AC. I was wondering if we would see anyone.
The girls were entertaining Lucas since Cal was in one cabin and the other two in the other. Atlas and I kept fucking for the next two hours with a couple of breaks to catch our breath.
The captain stuck his head in telling us it was time to head to the docks. It was already 2 am. I asked him to give me a couple of minutes and went for another quick dip with Atlas looking out for me since I was exhausted. I dressed if you can call my monokini and cover as getting dressed.
The girls and I exchanged numbers. They asked if I could come to do a guest appearance at their club. I told them to contact Mr. Malone and gave them his number. Then they left on their zodiac.
On the way in Atlas and Lucas woke, as much as they could, and helped Cal get dressed and somewhat awake. Winking at me they left the cousins naked and passed out.
We were met at the dock by Mike and Mr. Smith. They helped Cal off the boat. When Mr. Smith looked concerned Lucas didn’t miss a beat. He told them, with a straight face, that Cal had spent almost the whole cruise proving he was worthy of being a porn star himself and that he was exhausted. He had gotten drunk, but it didn’t slow him down. When asked about the cousins, they told them that a couple of girls had come onto the boat and they drank and spent about forty-five minutes with them and passed out for the rest of the cruise.
Mr. Smith ate up the bullshit story.
Beaming with pride he looked at me. “So he fucked you good?”
Playing to his ego, I answered, “God yes he did, but honestly, you were better, but he was very talented. However, these two are being modest. Cal was a bit drunk and at one point he tried to go swimming. By that I mean he had just cum on me for the third time when he sprinted to dive in the lake. These two were alert and stopped him before he went in. Not sure how that would have ended as drunk as he was.”
I saw nothing wrong with adding a lie or two giving them both some credit I am sure they deserved for other things that they never received. I did not tell him that both Atlas and Lucas were incredible fucks. If I told Mr. Smith that it would end badly for those two. Old money men have large egos but they are also very fragile in many ways. Instead, this way they might get some accolades.
Atlas helped Cal into his dad’s limo. Then they put the cousins in a second limo, still passed out and naked. There was a van waiting for them. Mike and I were sharing a drink on the boat with the captain.
The captain handed over a Flash drive with a video of all that went on. I knew that all was being videoed. It was part of the deal with Mr. Malone. In the most charming manner, he kissed my hand and told me I was always welcome on his boat.
With that, we headed to our limo. Atlas was waiting. After asking Mike if he might have a word with me we stepped a bit apart. He reminded me I owed him a favor.
“Anything." Assuring him I would honor it, we exchanged numbers.
In the limo, I told Mike that Mr. Malone should interview him for a job. Then to thank Mike for his services I leaned over unzipping him. He chuckled, "You truly can't get enough can you?"
I didn’t answer, verbally at least.
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