Sailing with my daughter and friend

Most people understand how mistakes happen and how things can easily get out of control.
If you’re a guy and there’s a beautiful woman trying to seduce you, sometimes our moral compass gets stuck.


I am a pretty happily married 44 year old man. I married a wonderful woman 18 years ago and have a wonderful 17 year old daughter, April.
As with most marriages, there are good days and bad days. Sometimes we feel neglected and other times the king of the world.
Though, for the past several years, a certain area of my marriage has been diminishing, Sex.
Though my wife and I talk about everything and she knows I want more, it never seems to manifest itself into reality. There’s always something that needs to be done, or she’s too tired or our daughter is around.
So, over the years it has dwindled to once every 4 10 6 months and then only a quick romp, no foreplay or oral activities.

Needless to say, I have spent my share of time pleasuring myself.

One of the hobbies that has always brought me and my family a lot of pleasure is sailing.
We have a nice 36 foot sailboat and we try to go sailing as a family as often as possible during the summer months. My wife is a nurse and sometimes has to work the weekends, which allows my daughter and I some bonding time on the water. We’ve enjoyed our time together sailing or playing games or just talking. I am often the one April comes to talk to since I am the least conservative parent.

When my daughter turned 12 she met her best friend Sara. From then on they were together often. I watched over the years as they both grew in to attractive young ladies. Both girls were about 5’5 and around 110 pounds. April has brown hair that comes just past her shoulders and brown eyes like her mother. Sara has light brown, almost sandy blonde hair that is slightly curly and beautiful blue eyes. Sara also has a slightly rounder face than April and a slightly larger chest, April being a small 34B and Sara being a 36C. Both girls enjoy playing sports and swimming which keeps them both in amazing shape.


As a practice we try to go sailing most weekends during the summer. Naturally April asked if Sara could come along and I agreed. I was a little sad when we set out and April and Sara retired to the foredeck to tan and chat. I couldn’t help but feel a little sad to be losing some of our quality time. Though Sara fit in nicely and became like part of the family.

Over the next 3 years I watch as April and Sara went from scrawny, awkward girls in to (too) quickly developing ladies. Last summer, my wife’s Aunt became ill so my wife spent a lot of her free time going down to look after her and helping her out.

This, of course cut in to our “family sailing time”, but I knew it was important.
April and Sara however still wanted to continue our sailing time so I would often take them and go sailing with just the three of us. Most days it would just be a day sail, leave in the morning and come back in the evening. Usually a couple of times a summer we would anchor out and spend the night.

Now sailing with 2 teenage girls was a lot like sailing alone. It usually went like this. Shortly after leaving the docks, the girls would plant themselves on the foredeck and commence to sunning themselves in their bikinis. Around lunchtime they would come back to the cockpit, we’d eat lunch then they would return to the foredeck.

I didn’t really mind much. After all, I got to go sailing and every time I looked forward, I was greeted with the site of 2 beautiful young figures (even if one was my daughter).

On our fifth trip of the summer with just the three of us, April had asked if we could anchor out by crooked island. It’s not the real name but one she had given it growing up and we let it stick. It was a small island that had one good holding area big enough for one boat and a few rocks that jutted out over the water to jump off of. Usually when we anchored there we were pretty secluded and rarely saw any other boats. I agreed and we loaded up the boat and headed out for the 4 hour sail to the island.

As usual, once the sails were set the girls proceeded to the foredeck and commenced tanning. After about an hour my daughter walked back to the cockpit and sat next to me. I knew she had something on her mind and just asked “What’s up pumpkin?”
She almost seemed a little embarrassed then asked if it would be ok if they tanned topless. Then she proceeded to explain how they didn’t want the tan lines and the other girls at school did and so on.
To tell you the truth, I didn’t really care. I knew that a lot of girls did. I also knew that my wife would not be too happy with the idea. I told April that I really didn’t care, but her mother would not approve at all. April agreed but said that they would only do it when mom wasn’t here and they wouldn’t talk about it away from the boat.
I told them that they could only do it if we were away from other boaters and they would have to cover up if another boat came by.

April quickly agreed, gave me a quick hug and went back to Sara. I watched as April told Sara the news then each untied their bikini tops and lay down on their backs.

OK, so I know it was probably wrong to do it, especially in secret, but what harm is it for them to tan topless?

Though I don’t think I was really ready for the scenery now present on my deck. I always had a sight of the girls tanning, but now as I looked forward I was presented with two sets of breasts. Two very perky sets of breasts. From my vantage point about 12 feet away I could clearly make out Sara’s wonderful breasts and in the cool breeze I could swear I could see two very hard nipples.

I snapped out of my stare and said to myself “What are you doing?” I tried to busy myself with checking sails, our course and watching out for other boats.

We reached the island around 1 and I lowered the sails. The girls quickly replaced their tops and April helped anchor the boat.

Once secure, we made a light lunch of cheeses, fruit, crackers and salami. The girls continued to chat about school, other friends, clothes, etc. I personally couldn’t help but star at Sara’s chest and swore I could almost make out her nipples under her bikini top.

After lunch, the girls jumped in to the water and swam to the island to jump off the rocks and swim around. Being the middle of summer, the water as still chilly, but a nice change from the hot afternoon sun.
I finished cleaning up after lunch and hit the head. Then I turned on the radio and found some music to listen to. After that I took a jump in the water myself to cool off. And cool it was. I had just swum around to the ladder when I saw the girls heading back. They said they were cold and were going to go warm up. I watched as they climbed the ladder and the water made their suits cling to their tight little bodies.
I swam away from the boat a little to try to clear my head. I decided to swim toward the bow of the boat and just float. I floated for a little bit, but the cool water was starting to set a chill in me as well. As I turned over to start swimming back I happen to see the girls sitting on the deck and removing their tops. There were those lovely young breasts defying gravity before me.
I quickly stuck my head in the water and swam back to the cockpit. Still I couldn’t get that vision out of my mind.

The girls continued to sun themselves until around 4, then they came back and we played scrabble until dinner time. I almost thought it seemed as though Sara was constantly looking at me with that cute smile of hers. After dinner the girls did the dishes then asked it was ok if they played War. I agreed and took my drink up on deck. I sat in the cockpit and enjoyed the relative silence off it all, relative, meaning over the sounds of the girls below. Around 8, both girls came up on deck and we all relaxed. Sara commented on how peaceful and beautiful it was and thanked me for bringing her. Around 9 the girls went below to get ready for bed. I did one last check of the anchor and decided to head to bed myself. As I descended the stairs, Sara came out of the forward cabin in just a large t-shirt and who knows what underneath. Though I could tell she wasn’t wearing a bra as her nipples were very noticeable through the thin fabric. She quickly slipped in to the head and my daughter came out next in her tank top and shorts to wait her turn.

April thanked me again for bringing them to the island and for everything today. I gave her a hug and a kiss on the forehead then watch as Sara come out of the head and April went in. I swear Sara did an extra wiggle. After the girls were in their cabin, I shut down the lights and went to the head myself. I climbed in to the berth in the aft cabin and did my best to try to sleep.