Boating Holiday

Boating Holiday

A good part of this story is true and what occurred on the trip has been slightly improved.

Chapter one:

My name is Mike and I love my boat “Lollypop.” She’s a new Amel 64’ twin mast built in 2014 a true blue-water cruising yacht. The boat has electric winches and in mast furling and below decks there are three cabins and sleeping for eight at a pinch. I’ve been sailing all my life, with my Dad and uncles when I was just able to swim then competition sailing in a VJ sailing club during High School. Through College I sailed with Dad in regattas and got my scuba license.

I’m my own boss now 20 years later and own a software company. I take off every chance I get to sail, I usually ask some colleagues at work if they would like to help me sail for the weekend and do some fishing and usually don’t have to ask more than once, they ask me when I’m going out again.

Dave works in shipping and Ben on the back dock and both love to fish and are not bad sailors and know what to do when it’s their turn to do a watch on board. The boat is easy enough to sail with the three of us and where’re comfortable with her now. We’ve been out on short trips up and down the coast with the longest trip of a week away sailing and fishing the islands to the south.

Dave has a wife, Meg and twin girls Sandy and Shelly, Both about to turn 18 this month and go to the same school as Ben’s girl Celeste 18 (going on 21). My wife Carol and I have a girl too. Bess has just turned 18 goes to the same school as the other girls and plays the same sports, swimming and netball. We love our girl loads and she has me wrapped around her little finger so she gets spoilt terribly being an only child.

All of us, Mum’s, Dad’s and kids had been out on the boat ever since I had bought it and right from the start there was an air of casualness as soon as we left the dock and the Wives took off their bikini tops and didn’t put them back on till we returned to the dock. This made meal times great with all of the nice firm flesh on display, of cause the kids wanted to follow suit and in the end they were running around the boat naked. Back then they were all about just young kids, and we thought nothing of it and occasionally the wives joined in sunning themselves on the deck with the excuse that they didn’t want any strap marks from their bikinis. Safe to say us guys weren’t complaining and sported full on hadrons’ for most of the trip. These days the wives and girls think nothing of stripping off as soon as we’re underway. If they are up on deck they’d keep an eye out for other boats out on the water but below decks they would wander around cooking and playing games and sleeping in the nude. As much as we all loved sailing and fishing the women would have nothing to do with smelly fish or days without a proper shower or bath so this time the wives have opted to stay home and relax with trips to the Day Spa for sauna’s and get some much needed Manny/Pedy’s.

This year wouldn’t be any different as our daughters would be coming along and helping to crew but it would be the first time they had come along without their mums along. You would think that at 18 they would want to be with their boyfriends or out clubbing with the other girls but as Dave put it ‘they tell me that this is the only chance they get to strip off and sun without worrying about getting pestered or perved on by a boy.’ The four girls had it in their heads that they would be su0nning themselves on deck and doing nothing else. Ha. There’s always work to be done on a boat.

On the day we were leaving for our five day trip we all met he at the dock with our duffle bags in tow. The Mum’s spent a long time going over and over how the girls would have to obey the Captain and follow orders as their lives may be on the line. I had spent the previous day restocking the boat with enough food to last the time we would be away and checking all the lines and weather for the trip. We spent a good hour familiarizing the girls with the boat and their jobs as crew this time as we would need them to help with the sales and gear. I went over how everything worked, like the Dingy and gas stove and the safety aspect of sailing.

The sleeping arrangements would be the same as they usually were except the girls would sleep in the same cabin as their Dads and not in the communal lounge. The girls all wanted to share a room, all but Bess wanted to share with me in the aft cabin. That left Dave and Ben sharing the cabin with the two single bunks and the 3 girls sharing the double bed in the other forward birth.

Finally we were off and the guys cast off the lines and we pulled out into the main channel. The girls all huddled together under the Bimini and waved at the other boats as we passed. We had planned to head south again as we were familiar with the currents and islands and knew where to anchor for the overnight stays. Our first night would be 70 NM down the cost at a small island chain dotted with palms and sheltered coves.

As I got into the routine of making passage to our first anchorage the others went below deck and before too long I could smell the food being cooked for lunch. Shortly after Bess came up on deck with a hot dog and fry’s for me. She had changed into her bikini and I was surprised how well she filled it out. It was light blue and she noticed me staring and did a twirl around for me showing off her string bikini bottoms and her front tie top. I knew it wouldn’t be staying on long and she had worn it just to show me. I was flattered.

Next to come up on deck were Dave and Ben in long board shorts with their rods and bait buckets. “We’ll be down the back if you need us Mike” said Ben. “The girls are all getting changed and stowing their gear after eating lunch.” With that they headed aft to fish.

“Can I help you sail Dad?” asked Bess and sat in my lap as I sat behind the wheel. This wasn’t unusual as she was quite proficient at sailing and navigating and could probably do a night watch if it was calm. What was unusual was my reaction to her cute little ass sitting in my lap with me in my Speedos and her in her thin bikini bottoms. I could feel my cock starting to stiffen and poke out the top of my costume, the draw string tight just under the head poking out. She leant back into my chest and put her feet up on the wheelhouse consul just as the rest of the girls came up the stairs, each naked and covered in a thin film of sun screen. First came Sandy and Shelly both would be turning 18 this week and I had stowed some presents for them below. Their nipples hardened as I looked at their chest. Bess made a comment on how she could just make out the lines from their costumes and this made the girls spin and show off their bottoms. I could only gaze and sigh at the display before me, and they giggled at my reaction. Next was Celeste, at 18 she had the almost full figure of a woman but retained her slim teen waist and flawless complexion. Her body also showed white lines where the string ties would be if she wore a bikini. The white triangle covering her mound was so tiny that her bikini was covering nearly nothing when she bothered to wear one. They all shaved their pussies completely and they glistened with the tanning oil they had used.

“You all look lovely, are you going to get some sun on the front deck mats?” I said.

“Yes,” said Sandy and Shelly at the same time as they often did and went off. Celeste asked what all the dials on the consul were for and Bess lent forward and pointed out the different dials and gauges. As she leant forward and pointed my stiff cock was exposed to Celeste’s view and look she did. Then she placed her hand on Bess’s lower back just above where my cock was sticking up. She continued to talk to Bess asking all sorts of questions but lowered her hand till she was stroking my cock head and toying with the Precum leaking out. She pulled the draw string and released my cock from its confines. I was stunned by her actions. We had fooled around in the past to some degree and the girls had laughed when they saw what their accidental bump or touch had caused and our hard cocks rose up. We all had but this was deliberate and full on contact with my stiff cock in her hand. Then she said that she’s like to get behind the wheel if that was all right? As Bess hopped off and Celeste sat down she took hold of my cock and pressed it down on the seat cushion as she sat down with her pussy sitting on my stiff cock.

“This is fun” she said and wriggled about. I put my hands on her hips to quiet her movements before I blew a load. She was pointing to the sails and the rigging and Bess was looking up at the mast and saying something. All I was aware of was that Celeste had adjusted my cock while Bess was distracted and it was now in direct contact with her hot cunt. I moaned and Celeste asked if she was too heavy and should she get up and started to rise.

“No, no stay there.” I knew that if she hopped off I would be exposed to my daughter so I pulled her back tighter to my hot cock now dripping with her juices and mine. As she sat back down she looked to be adjusting her position on the seat but had spread her lips and as she sat my cock my was just inside her moist cunt and as she sat back it sunk in even further.

Bess had a small smile on her lips and leant in and gave me a kiss on the lips as she stripped off her bikini and left to go up front with Sandy and Shelly. Left alone I pulled down on her hips trying with all my might to get as much of my cock as far up her as I could. The tightness was incredible. She leant back on my bare chest and sighed. “I’m on the pill,” was all she said and started to Jill herself off. As she got close to Cumming her pussy tightened and squeezed my cock and I pulsed till I filled her with cum. She sat up and we came apart and she left saying she had to use the head.

I had just enough time to put my now soft cock away when Ben came up and said that he would take watch for a while and give me a break. He’d just use the head and be right back. While he was gone I took in the view of Sandy, Shelly and Bess lying out on the foredeck cushions. They had applied tanning oil and they all looked great. They lay on their backs their lovely little breasts on display. Sandy and Shelly had long legs with toned muscles from swimming and I could not get over how hot they looked. In Bess’s case I could see her slit slightly open and she looked to be aroused. Sandy rolled over part way onto her sister and lay with a leg draped over her sister’s upper thigh spreading her legs open to my view and showing that one of her lips was also slightly open now and glistening with moisture. She ran a finger along her pussy lips and dipped the digit in to her moisture and brought it up to her sisters waiting lips where she spread the pussy juice over her mouth and inserted her finger between her sister’s lips. I sat there stunned. Bess glanced up my direction and then whispered to the other two girls and they all looked up and gave me cute little girl finger waves and giggled. I waved back automatically then laughed out loud. They had set me up and I had taken the bait.

Ben still wasn’t back so I set the autopilot and went down to the galley. I got a drink and heard voices coming from the forward cabins. Now the internal walls of a boat are made thin to save weight but that also makes it as though there isn’t a wall at all when someone is talking on the other side.

I heard Ben say, ‘What surprise?’ and Celeste reply ‘Suck my pussy and find out my cuckold daddy.’ Then nothing till ’Yes that’s right lick me clean. Drink in that cream pie.’

I was in shock. I never pictured Ben as a cuckold and not to his daughter. I turned and saw Dave just heading down the stairs so I said ‘Hi. Just getting a drink do you want one Dave?’ I listened for any voices coming from the rear cabin, but all was quiet now as I handed Dave his drink and went back up the stairs.

I sat at the helm and digested all that had happened in the last hour. I had gotten a hard on over my daughter sitting in my lap. I had fucked Ben’s daughter and he had eaten her out knowing it was full of cum. Sandy and Shelly had put on a very lovely and sweet lesbian show on the deck and knew that I would be watching and as I sat back down I looked out the window to see that the girls had spread their legs and lay out totally nude, just amazing.

Dave came back upon deck and we both admired the tabloid of young flesh before us. “It’s unbelievable how fast they grow up.” He said, “just look at them, firm young flesh, great little tits and the sweetest of pusses’ you’ve ever seen. It’s not that long ago that I was playing Marco Polo with them in the pool and now it’s a full on grope session with me getting groped. Not that I’ll ever complain mind, I love it and I suppose they are into that inquisitive stage now anyway and allowing them a bit of leniency now and then will only broaden their view of their world. This trip will be good for them and I’m hoping they will be that much more mature at the end.” I could only agree.

Chapter two:

That evening we pulled into our mooring and tied down to a mooring ball for the night. After a meal of Mac and Cheese and 3 bottles of wine we were all feeling pretty mellow. With the boat decked out to sleep 6 and there being 7 on board it was decided that Bess would sleep with me in the rear cabin, Ben and Celeste in the double bunk room and Dave, Sandy and Shelly in the other double bed cabin. But during the night things changed. We had decided long ago that even when at anchor or moored we should have someone on watch. We had heard stories of ships being boarded at night or just waking to find your dingy missing. Dave was up on deck for his stint at watch which left Sandy and Shelly alone in their cabin. It was not 5 minutes later that there was a knock at my door and Shelly said that they didn’t feel comfortable sleeping without dad there and could they sleep with us till his watch was over. That wasn’t due to be over till 6:00. I said OK and shuffled over. There wasn’t much room so it was decided that Bess being the littlest would lie on top of me and Sandy and Shelly would sleep on each side of me. That went well for a bit until I got a cramp and asked if I could bring my arms up and put them under the twin’s shoulders and they could rest their heads on my shoulders. That went well for a bit until I felt a hand exploring my balls inside my boxers. The hand found what it was looking for and started to stroke my now hard shaft. Bess was lying with her legs spread outside of mine and the stroking caused my cock to lengthen and start to poke at her pussy. It’s then that I realized that it was her pussy that I was feeling and not her panties.

I felt my cock head rub along her slit and her moisture lube the head then stop and nudge her entrance. She must have felt something because she sighed and wriggled a bit to get more comfortable and then it slipped in and the head was lodged inside my daughter’s young teen pussy.