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Summer Sailing

Posted by: Author: Age: 42 Posted on: 0 comments
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Sailing is the best!


I'm a single, avid sailor who, until last May, owned a 37' sailboat in Annapolis, Maryland. My favorite times were on my boat in the summer, with the drinks flowing, the music cranking and the 'crew' dancing and enjoying the freedom from the real world ashore.

Two summers ago, my girlfriend at the time, Lani, and I had invited a mutual friend of ours, Pam and an office mate of hers ('boyfriend du jour') for a day sail around the Chesapeake Bay. It turned out to be one of the area's infamous blistering hot days with such high humidity when at 10 a.m., you are already searching for air conditioning.

I wanted to abort the trip, but then Pam and Lani turned up to the boat (I, as usual, had slept onboard the night before) with enough provisions for a week and so I figured it was too late to cancel.

Pam's office mate was smarter than I was though, and had conveniently called Pam early in the morning with a lame excuse, and thus escaped the broil that was sure to occur. 'Lucky bastard,' I thought as I envisioned him camped out on a couch in A.C. watching TV all day.

Pam and Lani were excited about the trip nonetheless, and no sooner did I push off from the dock that they had the blender going and the music blaring.

As is usual on such hot days, there was little if any wind, and we spent most of the afternoon motoring around the Bay with our sails flapping against the shrouds. If I hadn't had two beautiful drunk women in bikinis dancing on my foredeck I would've been back at the dock in a heartbeat. At least we had plenty of alcohol and ice.

The girls finally suggested that we head to a cove and go swimming, which, with no wind, didn't take much of a decision. I quickly whipped the boat around and headed for my favorite swimming hole up the Rhode River.

Besides the girls, the only other good news of the day was that the heat had kept the smarter folks ashore and the Chesapeake Bay was deserted. I didn't really notice this until I arrived at the swimming hole and realized that we were the only ones there. Usually, there are at least a few boats anchored, with people floating around on cushions. Today, however, we had the place to ourselves and I wasted no time dropping my hook right in the middle of the pool.

No sooner was the engine off, than the girls were in the water. I made up another batch of Margaritas, slid them over the side in a floating cooler, tossed some cushions overboard and joined them.

I'll never forget how wonderful the water felt that day. It was perfect with isolated springs of cool water gushing up from its murky depths. Within minutes, we were all three perfectly balanced on our cushions, drinks in hand, and ready to spend the whole afternoon in the water.

As usually happens on such days, the drinks went down unnoticed and the hours quickly slipped away. The three of us floated around each other discussing topics ranging from politics to penises, with the odd dirty joke thrown in occasionally for laughs. It was a great afternoon and it wasn't until the sun was setting that we all decided to climb back aboard and make some dinner.

A few more pitchers of Margaritas later, Pam started looking woozy and decided to lie down for a rest. I suggested that she lie down in the V-berth up front where there is more room to stretch out. Lani and I kept drinking ... and frankly, at this point, I had already given up any thought of pulling anchor and heading home for the evening. I was too drunk, the heat had lost its burn and gave way to wonderful warm breezes, and I could think of nothing worse than wrestling with the anchor and finding my way home in the dark.

Pam was out cold, and at some point Lani had also slipped away to the V-berth to snooze. I probably would have fallen asleep on deck like usual if I hadn't been so damn horny. I guess the accumulated effect of hanging around half-naked women all day had taken a hold in my libido. I stumbled downstairs to find the two sleeping beauties passed out in their bikinis.

I snuggled between them and quickly slid my hand down to Lani's pussy. She was dry, but stirred a bit as if she felt it. Encouraged, I pulled her bikini top aside and started sucking on her nipple. It responded nicely and within seconds I had a nice firm nipple to tongue and lick.

After a few minutes, Lani opened her eyes and sort-of looked as if she was trying to determine if this was real or a dream. A second or two later, my fingers started feeling a bit of her juice start to flow. I quickly slipped my fingertip into her vagina and started encouraging more, scooping the wetness out as she made it.

Lani was now fully awake and I could feel her stretching and tightening her muscles as she became aroused. I kept sucking her nipple while slowly sticking my finger deeper inside her. As her clit became swollen and wet, I moved to circling it lightly with my fingertip. It didn't take long before Lani's pussy was relaxed and overflowing. Lani is always the most 'open' right at this point and I always enjoyed quickly putting three, and sometimes four, fingers into her. She loved this 'hand-fucking' and I never could do it for more than a few minutes before she would start begging me to replace my hand with my cock.

She put her hand down my swimsuit and started squeezing me. Lani knows that I like my balls massaged and so she moved down a bit and started squeezing them. Within seconds, I was as hard as a rock, throbbing with every heartbeat. There is something about hot weather that makes my cock swell to an enormous size.

Till now, I had forgotten about Pam, and I only remembered she was there as I sat up to help pull Lani's bikini bottom down. I think Lani had forgotten that she was there also, because she hesitated for a bit and gave Pam a quick glance while pushing her panties down. Although Pam was facing us, she had her eyes closed and looked to be in dream world. Lani and I enjoyed each other for a while, and it wasn't long, before Pam had her eyes wide open. I'm not sure when she had started watching, but she was certainly awake now.

I hate to admit this, but I immediately went soft. Once, I was caught having sex by my mother, and I guess that it left a permanent psychological scar. For a long second, all three of us looked at each other not sure of what to do or say.

Before I could mutter, 'Sorry for waking you.'

Pam said, 'That looks like fun.' Since Lani and I were naked without sheets or anything to cover, we just laid there as Pam scanned our bodies.

We all remember certain seconds in our life. Challenger blowing up, Reagan shot, our first fuck. Well, I will forever remember those seconds with Pam looking at us, and finally saying, 'Please don't stop because of me... I enjoy it.' With that, she reached out her arm and placed her hand on Lani's breast.

That's all it took. One brief gesture. I was hard again. Lani was wet again. And everything felt natural. I reached over and pulled Pam closer to us. Lani rolled over to face Pam and in a few seconds I had helped Pam pull her top off. With that, Lani leaned forward and started sucking her nipple. I guess that she had been waiting a long time for an opportunity to do that.

I sat up to give them room, and then slid my left hand back into Lani's gushing pussy. When I saw Pam instinctively roll onto her back, I didn't waste time getting her bottoms off and sliding my right finger into her already wet mound.

For the first time in my life, I enjoyed fondling two pussies at the same time. It was a mind-blowing experience. Surprisingly, the first thing I noticed is how 'different' they felt. While Lani was wide open and slopping, Pam felt small and tight. Lani's juice felt wetter while Pam's more slippery. Lani's clit was swollen and huge against Pam's small and protective pearl. I could smell the difference, too. Two wonderful smells mixing together.

It was amazing sitting there on my knees massaging both mounds watching the girls kiss and rub each other's breasts. They were obviously enjoying the full stimulation. I knew that Lani had long fantasized about being with another woman. We had discussed this on numerous occasions and she had hoped for an opportunity. I was impressed that she wasn't holding anything back. I guess that it was the secure, cocoon-like feeling of the V-berth that encouraged her to let loose.

After a few minutes, Lani reached down and started massaging Pam's pussy with me. I think that she was also eager to see what another woman's pussy felt like. Lani and Pam started kissing intensely, with Lani occasionally sucking Pam's tits.

Pam and Lani continued to kiss and suck each other. Pam eventually put her hand down and started massaging her clit as only she knew how to. I crawled onto her other side and started sucking one of her breasts. It didn't take long for her to cum also.

It was a wonderful experience. We giggled for awhile, too excited to sleep. I jumped back in between them and we all cuddled up as one; talking until we passed out.

By the time I awoke, the girls were already up and drinking coffee, so I missed out on a morning show. After a brief swim, (no clothes this time), we hoisted anchor and motored home.

Lani and I broke up about six months later. Pam moved to California, so I don't think that there'll be a reunion anytime soon. But I still have the memories....



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