It’s A Small World – Regatta Fun!

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tagGroup SexIt's A Small World – Regatta Fun!

This is one of my hubby's favorites stories from my past. I have to admit that it taught me that the world is a small place, LOL.
It was Columbus Day weekend which meant the yearly "Columbus Day Regatta" in South Florida. The Regatta was basically an orgy off Elliot Key. Thousands of party goers would pack themselves on any sea worthy vessel they could find and head over for a weekend of drinking, partying and SEX! A vendor of ours, Logan, invited Lacy (my coworker) and me to go out on a yacht owned by one of our wealthy clients. He was interested in seeing for himself what all the talk was about. Lacy accepted and I asked if one of my friends, Gina, could come. He said sure so I was down as well.
The partying starts Friday but the yacht wasn't available till Saturday which worked out better as my husband was going golfing and then to a "business seminar" afterwards. We all met up at Gina's house and drove over to the marina where the yacht was kept. It was a Bertram and I believe he said it was about 60'. The interior was gorgeous with a kitchen, bar and tastefully decorated bedrooms. One was a suite with a Queen size bed while the other one had two smaller side by side beds. This was nothing compared to the dinghy's I had been in before. All three of us were elated to step aboard as it felt we were on an episode of "The Rich & Famous", LOL. The client was there along with another man, who I had never met before, along with Logan and the guy driving the yacht.
The unknown man was a business partner of the client. They were both in their fifties and not attractive. Our client was short with a big pot belly while the other one was tall but in better shape. Logan was tall and slim with light brown hair and white complexion. He had pretty blue eyes and a great smile besides being very eloquent and charming. The Captain was also in his fifties but seemed to be in very good shape. He had one of those Captain hats with a shirt that made him look like a Navy man. We christened him "Cap." Once we departed we removed our blouses but remained with shorts and the bikini tops. The drive over to Elliot Key was about 45-60 minutes from the Marina. As soon as we got there the place was jam packed with boats and partyers. Many people had already shed their clothes. The men were loving it.
We find a spot and anchor so the shorts are gone as are the sandals. We all had thong bikinis and had similar bodies except I had a bigger ass and darker complexion. Lacy and Gina's boobs were quite larger than mine. All the men except Cap stripped down to these very itty bitty Speedos that left nothing to the imagination. The client and Tall guy had exposed ass cheeks while Logan's was covered. Logan and Mr.Tall were packing some serious man meat especially when they stood sideways. There was a pronounced bulge that protruded well over Logan's skinny waist. It was hard to not look especially when we were talking. My eyes kept shifting to their package as I found it so curious as did Gina and Lacy. Gina had already whispered that she wanted to jump Logan and "set that baby free!" as she so eloquently put it.
Cap had prepared "Top Shelf Mai Tai's", as he described them, with his unique twist for all, which he so graciously served in these unique cups. It was a sweet drink but after just one I felt the buzz as I stood up to use the bathroom. I walked down inside and as I was inches from the bathroom Mr. Tall was exiting looking down trying to put this massive appendage inside his trunks. I stood there quietly and somewhat aroused watching this man straining to pack that man meat inside those tiny trunks. He finally succeeded when he realized I'm right in front of him. I didn't know if he knew I just saw his Johnson or not but he was very gentlemanly and apologetic. It was hard to talk with him since he was French and spoke very little English. Nevertheless I used the bathroom but kept thinking about what I had just seen.
Logan knew quite a few people that were already at the Key so pretty soon the yacht was filling up with people, mostly women, and most were already topless. The yacht had a great stereo and soon we are in full party mode. Gina was the first of us to lose her top. Watching her beautiful breasts jumping up and down while dancing was a feast for the men. She was very shapely with long legs but her boobs were her best feature. She had also recently pierced her nipples so that was an added bonus that didn't go unnoticed by anyone.
Everyone was mingling about or dancing while I simply people watched enjoying Cap's concoction. I decided to light up one of my blunts but didn't want to share with everyone onboard so I climbed up to where the steering wheel was since no one was up there. Cap had asked that no one go up there so I figured it would be perfect. I take a couple of puffs but Cap saw me and gave me that "What you doing disobeying the Captain's orders" look but I simply smiled and mooned him. He had a great laugh and I was forgiven, LOL.
The party went well into the night but around 1:00 A.M. things subsided on our boat but no one wanted to sleep yet. We decided to stay the night. I called in and my husband was staying over a friends house cause he drank too much (Yeah right!) and we just decided to enjoy the breezy night air. There were no waves so the yacht was perfectly still. Drinks kept coming while we all hanged out laughing at Logan's off color jokes.
There were two other girls that remained with us from before. Lacy was sitting very cozy with Mr. Tall and by this time all three of us were topless. Gina took this opportunity to tease the men by asking them what was in their Speedos. Sober Gina is crazy, Buzzed Gina is another dimension of Sexuality where there are no limits. Logan tells Gina, "I would show you but I don't want to scare you." which got everyone going and hollering.
Well that just encouraged Gina even more. "Baby I don't scare easy. Let's see what you got." she said coyly. She removed her bikini bottom and crawled over to Logan then looking straight at him proceeded to lower his Speedos. Logan had a sizable member with a huge crooked vein running at the top. He wasn't exceptionally long but he was very thick.
Logan stepped out of his Speedos with Gina's help. She stood up next to him and gave him a quick wet kiss that stirred his manhood. She looked over at me saying, "Take it off Mami" so off went my bottoms and so did the rest of the other girls'. Lacy pulled Mr. Tall up so he can show us what he was packing. Although I already had a very good idea, it was exciting to see Lacy coax him out of his barely there Speedo. Mr. Tall was already somewhat aroused as a long thick semi hard cock sprang out once Lacy removed his suit.
Mr. Client followed next with the assistance from one of the other girls. He was on the small side but had huge freaking balls. I mean HUGE! They looked like two oranges dangling between his legs and they were also very darkly pigmented. Everyone was stark naked on this boat listening to music and drinking. Everyone except the Cap. He was inside somewhere so I decided to look for him. I found him preparing more drinks and when he saw me walk in stark naked he did a double take.
Cap stopped what he was doing and stared at me eyeing me up and down. I slowly turned so he could get a proper 360 degree view of me, "Cap, your way overdressed and the ONLY one clothed on this boat." I told him in the most seductive manner I could muster up. I walked over to him and lead him outside so he could see for himself. Mr. Client calls him over and tells him to relax, enjoy and get naked! I looked over to him and tell him, "The client is always right Cap. Come on I'll help you." For some reason Cap had caught my eye. He was in his fifties with shoulder length Salt and Pepper hair and a matching goatee.
I removed his shirt first and he was surprisingly muscular with substantial chest hair. I got behind him to unbuckle his pants which allowed me to press my breasts against his bare back. Gina was dancing seductively with Logan and got behind him mimicking my moves with a devilish seductress look on her face. Lacy was sitting on Mr. Tall's lap drinking and smoking. Mr. Client was dirty dancing with the other two girls sporting a hardon while his gigantic balls swayed back and forth.
I took my time unbuckling Cap while rubbing myself unto him. Once his belt was undone I removed it completely and threw it on one of the benches. I unbuttoned his pants then unzipped his fly where l quickly felt a nice cock in what appeared to be a semi hard state. Cap steps out of his shorts but I made sure his briefs were still on. They were sexy Calvin Klein tight briefs that reached midway to his rather muscular legs. "Damnnnn Cap has it going on!" I thought to myself.
One of the other girls came over and quickly whispered in my ear, "That's so fucking hot. Your going to fuck him aren't you!" then gently nibbles on my earlobe while pressing her oily sweaty body against mine. I have to admit she turned me on with that quick risque move. My attention goes back to the Cap who is using his hands to caress my body but I'm still standing behind him. The music playing was Techno which added a Nouveau Sexual energy to the whole evening increasing my arousal. I was gyrating behind the Cap when the other girl returned but this time she started dancing in front of the Cap. My hands were inside his briefs following the rhythm of the music as I lowered them slightly then raised them back up again.
I would accidentally rub up against his cock when I felt something wet and sticky. "This for me?" I whisper in his ear while we keep dancing.
"Hell Yeah!" he answered back.
The other girl seemed to be Asian with long straight black hair. She was around 5'-2" but very shapely. Her breasts were really small however her ass and legs were superb. I was super aroused by now when I see Logan and Gina go inside. Mr. Client and the other girl walked past us and he squeezed my ass cheeks then took the Asian girl with him. They sit down and the other girl starts sucking him right there in front of everyone. The Asian girl was kissing him while he was fondling her body. "Well he's enjoying the Regatta" I whisper to the Cap as I removed his briefs.
Lacy was sitting on Mr. Tall who must have been hard as a rock by then when she gave me the "OK" sign as soon as she saw the Cap naked in all his glory. I turned him around to reveal a very sexy fit man that would put most younger men to shame. The Cap had a rocking tight body and looked much better naked than he did dressed. He was average sized and definitely kept himself manscaped as his hairs were trimmed very short. He had a super sexy "Happy Trail" of dark hair leading down to a wet spot of pre-cum dangling from his shiny cock head.
Lacy and Mr. Tall come over and she whispered in my ear, "We're going inside. I'm fucking him" Mr. Tall was enormous and he wasn't fully hard yet. I felt his cock press on my ass cheeks as he gave me a lingering hug from behind and kissed the back of my neck. He walked away leaving me with a wet patch wet of his pre-cum on my ass cheeks.
Cap took me by the hand and lead me inside. The first thing I saw was Gina on her knees giving Logan a hellacious blowjob inside the suite. We could hear Lacy and Mr. Tall moaning in the other room but the door was closed. The Cap and I took in the show for a bit while he was fingering me and I'm stroking his cock. We kiss and fondle each other right there in front of the kitchen. "I got the perfect spot" he says breaking from our embrace.
I follow him outside where we find Mr. Client fucking the Asian girl doggie style while the other girl is making out with him. Cap lead me up to where the steering wheel thing was. It was the highest point on the boat. Most of the lights on the boat were off except this sexy underwater blue lighting that gave the whole yacht a sense of calm. The night sky was flickering with stars as the cool breeze swept over our naked bodies.
I kissed Cap on the lips and knelt before him. I was captivated by his "Happy Trail" and follow it with my mouth as I lick him all the way down to his erection. Cap's dick was salty and he had a very arousing sweet musk that flooded me with a sense of lust. The fact that he was more than twice my age added to my wanton lust for him. I looked up at him and notice the starry sky beyond him as the cool breeze is bathing my naked body. I am on my knees on top of a yacht giving a man twice my age head in an idyllic surrounding. Everyone on this yacht was having raunchy dirty sex.
I was deep throating him so his cock was dripping with my saliva. I alternated giving his balls equal attention as every time I did so he would let out a moan. Cap pulled me up then gives me a long sloppy kiss. He had full lips which I nibbled on as our bodies were pressed tightly together. He lifted me up and placed me on the console then spread my legs as he leaned down in front of me. I felt his warm breath on my punani. He took his time parting my labia then went down on me in what turned out to be one of the best experiences I ever had with a man sucking me.
I grabbed his hair and took in the moment once more. I turned his Salt and Pepper hair into a pony tail as I rubbed his handsome face all over my soaking wet pussy. He was slurping away as my moans went out into the night air. I was in awe with this experience! I pulled on his hair tightly as his masterful oral skills gave me the first orgasm of the evening. He quickly got on his feet then starts rubbing my clitoris with his rock hard cock. I hugged him tightly trying to get him inside me. He kept teasing me until I grabbed his hair and screamed, "Fuck me Dammit!!!" He obliged and pounded me skillfully. Every thrust raised our level of pleasure and raw desire. Cap suddenly lifted me up and sits on one of the chairs which allowed me to dangle my legs behind him. I was able to really ride him deep inside my cooch. His length and girth were ideal for me to ride him fully and grind unto him with reckless abandon.
Cap grabbed my face to kiss me. I struggled to kiss him back as my moaning had taken on a life of it's own. I humped him harder while gyrating my hips and squeezing his cock with my pussy walls. He was biting my neck and licking me voraciously. I get that feeling again and bite down hard on his shoulder as my legs shake from another orgasm. I grabbed his hair and used my tongue to find his. He lifts himself from the chair then bends me over it placing my arms down so I can brace myself for the fucking he is about to give me. My legs are parted and before entering me he licks me from top to bottom.
He spread my ass cheeks as his tongue was pleasuring my backside. I find myself unable to stay still as the Cap has inserted his thumb inside me while my clit is between two of his fingers being rubbed to another impending orgasm. His tongue was dancing in my love canal as I screamed under the intensity of pleasure I was receiving. I slapped the chair as if it were somehow responsible for the pleasure shooting inside of me.
Cap spins me around and his mouth devours my face. We are furiously rubbing into one another when he turns me over again spreads my legs and rams his dick back inside me. This time it is not sensual. He is fucking me like a dirty fucking whore and I am LOVING IT!!! "Fuck me. Fuck me harder coño!" I yell at him. I don't care if the whole Key hears me. Hell I want them to! He has a tight grip on my waist and our bodies are now in perfect sexual harmony. It's as if we had been lovers all along.
Cap is pounding away and the sound of my wet pussy and his hips slamming mine are building another wave inside me. I felt juices and fluid running down my thighs. Cap pulled my hair then grabbed my face so I could kiss him. I can't! I simply can't stop moaning so I grunt "Fuck me you Son of a Bitch. Fuck me harder!" Where that came from I have no idea. It simply came out of a deep dark bestial inner part of my being. A place being discovered by the skillful fucking Cap is giving me. I spasm again under the pressure of yet another orgasm. Cap gave me at least two more orgasms before he finally erupted inside of me. I wanted so bad to taste his cum but my body was helplessly spastic from his lengthy thrashing.
He had his way with me for well over two hours! Two hours of being pounded into submission. How the hell was I going to get down those steps with these rubbery legs? I had to sit for a few minutes to simply gather the strength to be able to come down. I notice the top of his right shoulder was a little swollen and had the indentations from my passionate bite. When we get to the main deck Mr. Client is asleep with the two girls in a mangled heap of limbs and dried cum. Cap escorts me to the front of the yacht and arranges some throw pillows on the deck so we could lie down. "We will sleep here till the sun comes up. Trust me. You need to see this." As he gently kisses me and we drift off to sleep. We awaken with the sun bathing our faces. Even though we slept for a couple hours I was feeling so alive, so desired, so fortunate for this experience. I adjust my eyes and I notice this dark gray boat relatively close to us. It seemed familiar.
On my return home my cousin calls me super pissed off. "I have something to tell you. That POS husband of yours went to the Regatta. with Jose and his friends."
I reply "How do you know?"
"Peter (her younger brother) went with them. Look." she sends me pictures of all of them partying. I look closely and there was a gorgeous yacht in the background. On closer look I get goosebumps all over and smile. It was our yacht. I sit and wonder if he heard his wife moaning, screaming and cumming while a real man had his way with her! Life's a Bitch! In his case a Bitch named Linda, LOL!

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