Dionne was true to her word and booked a 2 day trip the following week, persuading her husband without much difficulty that she should sail with me alone. We enjoyed the sailing and fucked in every position possible on every part of the boat and I even broke my rule about leaving the boat to fuck her from behind whilst she hung onto the ladder that enabled you to get back on board from the sea (I justified this by assuring myself that we were holding onto the boat throughout). When we got back to base Dionne handed me another envelope, packed with even more cash than before, telling me that she and her husband were returning to The States in 2 days time so she would not be able to see me again. Whilst I was disappointed as I had enjoyed the sex and the cash bonuses, I was also a bit relieved.
There followed a few uneventful day trips with normal tips from grateful clients, I was totting up my bonuses, realising that I had enough to live for at least my first year at university but for some reason was feeling a bit depressed.
"Permission to come aboard?" I heard as a familiar smiling face appeared at the hatch.
"Simon!" I cried, "I wasn't expecting to see you."
"Last minute decision," he said, "Dad suggested that I come out and see how you are doing, we are getting a lot of really positive feedback about you!"
"That's nice to hear," I said.
"In particular, an American lady, Dionne Kerry was extremely fulsome in her praise for you."
"Oh, that is kind of her."
"Anyway, we have loads to catch up on, let me stow my bag and we can have a few beers."
"Do you want to head out for a bit?" I asked.
"Why not, it will be good to enjoy the sea."
I prepared the boat whilst Simon sorted out his stuff. We set sail and headed for my favourite bay as I knew that it had good anchorage and was nice and quiet.
We dropped anchor and both changed into swimming gear, me in swim shorts, Simon in Speedos.
"We can both swim as there are no clients and the boat is well anchored," he said so we both dived over the side to enjoy the water.
When we got back on board Simon grabbed a couple of beer bottles and we settled into the cockpit, soaking up the sun.
"There is something I need to tell you," said Simon, "and I am just going to come out with it. I'm gay."
I snorted, "no shit Sherlock!"
"You know?"
"I have always assumed it, I don't know why."
"Fuck, I have been so worried about telling you in case you were disgusted and didn't want to be my friend anymore."
"Simon, you are my best friend, you could never disgust me. If you are gay that is not a problem to me."
"Thank you, you don't know what that means to me," he said giving me a hug.
We sat drinking our beer and after a while Simon said to me "you seem a bit down mate, what's the problem."
I hesitated to say anything, so he added "I have shared my secret with you, so come on, tell me what is wrong."
So I told him what I had done with Dionne, leaving nothing out.
"No wonder her feedback was so good" he laughed, "so what is the problem?"
"I feel that I acted like a prostitute," I said, "she is only the second person that I have had sex with."
"The first being my Mum presumably?" He said.
My jaw nearly hit the deck, "How did you find out?" I asked him.
"Semen puddle on the lounger that time I came home to find you sunbathing with Mum."
"Oh shit, I am so sorry."
"What for, Mum clearly enjoyed it and I assume that you did as well?"
"Well yes, but I shouldn't have done it."
"It doesn't matter to me John, honestly."
There was a long pause, "So why are you feeling down, you have earned a lot of money and had loads of sex," he said
"I suppose it is because all of my sexual activity has been with older women, I still can't face asking out someone of my own age, and, as I said, I feel kind of dirty."
"So, if you could have a sexual relationship with somebody of our age, you would feel better?"
"Yes, I think that I would," I said.
Again, there was a long pause and then Simon leant towards me and kissed me softly on the lips.
"Whoa!" I said, "Where did that come from?"
"Just thought that I would plant an idea in your mind" he said.
I was stunned, I had always assumed that Simon was gay but never thought that he would find me attractive or that I might even consider him in a sexual way. The trouble was, my cock was staring to stir, leaving me feeling confused.
"I need another swim," I said and quickly dived into the water before he could see my growing bulge.
I swam about for a couple of minutes before returning to the boat. As I climbed the ladder, Simon was at the top and as I came level with his crotch he said. "I am sorry if I made you uncomfortable."
As I stepped into the cockpit I said, "It's fine, you just took me by surprise."
I suddenly realised that what I wanted was stood in front of me, my best friend. I hesitated and then leant in to kiss him softly on the mouth. He looked into my eyes, barely believing what was happening; he took hold of my head and kissed me deeply, probing my mouth with his tongue.
"Oh God that is good, you have no idea how long I have wanted to do that with you." Simon said.
I kissed him again and felt his hand brushing my cock through my shorts, "that feels nice" I said as I returned the favour and felt the outline of his penis and then pulling down his Speedos to reveal quite a small cock, only about 5" long but with a very pronounced glans at the end. Simon undid the string at the front of my shorts and plunged his hand inside and grasped my 8" erection. "Fuck that is enormous" he said as my shorts descended to the deck. We both kicked off our garments and stood gently stroking each others cocks whilst our mouths locked together again.
"Make me cum," he said so I started really wanking his cock, delighting in the feel of his hardness in my hand. "Oh shit!" he said as a couple of ropes of semen shot out of him and splattered over my torso and hand. I lifted the cum covered hand to my mouth and tasted it.
"Your turn," he said and knelt in front of me to start wanking me, his hand pumping up and down my length, swirling the pre-cum that I was leaking to lubricate his actions.
"I'm cumming" I said and released a huge amount of semen that splattered over his face, I pulled him up and licked it all of him. "I want to suck your cock," I told him "and I want to swallow your cum." He was hard again already so I knelt in front of him and took his entire cock into my mouth, marvelling at the feel of it in my mouth, the bulbous head feeling like a lollipop as it moved in and out of me, leaking salty pre-cum which I swallowed hungrily. Because his cock was relatively small I could take his entire length in my mouth with my nose buried in his pubic hair, inhaling his scent. I cradled his balls and then slipped a finger into his crack, seeking his anus to stimulate him further. As I penetrated his bum he grunted and unloaded a huge orgasm which I managed to keep in my mouth and swallowed it all down.
"Why don't we go into the cabin?" suggested Simon.
"Good idea" I said and we headed below decks.
"It's a good job the skippers bunk is a double on the boat" said Simon.
"Very lucky" I agreed as we collapsed onto it, holding each other in an embrace.
