The First Time For Us

I have been into boating for the last dozen or so years but my experience has been purely with powerboats. Dave, one of the guys in our office invited me out on his new sailboat and even though I had no sailing experience at all, I jumped at the chance of doing something I had never tried before.

His marina is about an hour's ride from the city and we met at a local Wal-Mart parking lot for the ride down to the boat. I thought it was going to be a little thing but it was forty-two feet long with a beam (width) of over eleven feet. Quite a boat! His father had bought it new a dozen years earlier but had recently died and left it to the son. Dave is just a kid of twenty-three while I am Chuck, the old guy of fifty-one.

The sail out of the marina and out into the Sound went great. Dave was saying the wind couldn't have been any better and from the way I was enjoying the ride I would have had to agree with him. He announced we could sail over to an island and then drop the anchor while we went for a swim and then had lunch. I explained I hadn't brought a bathing suit but he dismissed the problem saying he could probably find one on the boat I could use or I could just go bare ass since there wouldn't be anyone anchored within a mile of us.

We anchored in ten feet of water and were the only boat that I could see for miles. I mentioned to Dave that I had no problem going without a suit if he didn't think we would get into any trouble with the harbor police. He assured me they seldom come around and if they did we would see them while they were still a long ways off giving us plenty of time to climb back aboard.

He went below and stripped naked coming back into the cockpit to untie the swimming ladder that was fastened to the rear railing. I went down below and hung my clothes on the back of the dining area table before joining him back out in the cockpit.

He stood on the stern railing and did a super dive; something I would never try. I jumped in and we swam around the boat for a good while before he suggested we go back up and have a lunch of the goodies he had brought. Lobster salad with French bread and some white wine. I dried off and was just sitting in the cockpit letting the suns rays do the final drying of me as he was making the lunch. He could see out from the galley area and looked out at me and said ever so nonchalantly,

"Chuck, I couldn't help but notice you have a nice cock."

I gulped a little never expecting anything like that but replied, "Nice; it is probably one of the smallest cocks on the East Coast. Hell, I am barely seven inches hard and certainly nothing like those monsters you read about on the Internet.

"No matter, it looks nice to me. "C'mon down, lunch is ready."

We were both still bare ass naked and sat on the nautical chairs enjoying a great salad, bread and wine. I stood to go behind him to grab a napkin and as I passed by him he reached out and let his fingers trail over my now shrunken cock. Mine sort of hides when it gets cool and wet.

"You seem to like my tool Dave. I never had a guy touch it before."

"Oh shit, I would love to do a lot more than touch it. You probably don't know it Chuck but I am gay and have had eyes for you ever since I came to work in the office."

"Dave, I sort of guessed that with the way you suggested we could swim bare ass. You'll have to know I am straight as a string but your gayness doesn't bother me at all."

We finished our lunch and carried our wine back out to the cockpit to enjoy the sun. Instead of sitting opposite me he chose to plop down alongside of me. As his butt hit the cushion he let his hand drape over my upper thigh.

"Chuck, I would love to take your cock in my mouth. Just looking at it is driving me wild. Look at me," as he pointed to his crotch. His cock was harder than steel and standing out at what looked to be seven inches; about the same as mine. He moved over to let himself slide down to the floor of the cockpit and twisted himself so he was sitting between my legs.

"Dave, I have never had a guy give me a blowjob before. Are you any good at it?" I said laughingly.

"Oooh, a virgin. I'll do my best to make you think I am the best in the world." He joked

"Well, no where near a virgin but I guess I am as far as any kind of gay sex is concerned."

As I was saying this he had let his hand move over and was now holding my flaccid cock between his fingers. He let the other hand rise up and was soon fondling my balls. Hell, my cock did something I would have never guessed. It came to life with the encouragement Dave was giving it.

"Dave, if you really want to give me a blowjob let's go below. I don't feel at all comfortable having you do it out here."

He was up in a flash and dragging me down into the main cabin behind him. As soon as I hit the chair I had been sitting on while having lunch he knelt before me and soon had my soft cock buried in his mouth. As soon as he felt it hard he let it slip out and he then moved his tongue up and down the shaft tracing the veins with his tongue. He kept that up till I couldn't stand it anymore and told him to either suck me off or forget the whole thing.

"Quit fucking around and suck me off."

"Oh yes, Chuck." And he instantly had my cock buried and was moving as if he was bobbing for apples. He let it come almost all of the way out of his mouth before dropping on it to take in as much as he could. When it was soft he was able to almost bury it but he could now only take about five inches of it. No matter, whatever he was doing to it when he had it buried felt great.

"Dave, keep that up the way you are and I will be exploding in a minute." I barely got that out when the rush came over me and I was spurting hot come deep in his throat. "Whew, that was terrific."

He raised off me and just started to lick the head of it and then took the head back in his mouth and simply sucked on it. I had never felt any gal do that to me before but I think the difference must have been was that the gals were doing it to please me and Dave was doing it to please both of us.

We stayed like that for a while when I asked if he had any of that great white wine left. He jumped up to the galley and quickly had our glasses rinsed and refilled.

"Chuck, I have been looking at you walking around the office ever since I got there just wondering what it would be like to suck you off. I only sucked my first cock a couple of years ago and knew I loved doing it but I never felt anything for the guy the way I do for you."

"What makes you feel anything special for me?"

"I don't know. Maybe it's that you are good-looking, fit and are sort of a father figure to me. I really loved my own dad and it tore me up when he died."

"Well, whatever it is. You sure gave me one hell of a blowjob."

"Chuck, I'll do whatever you want. All I want to do is to make you happy and glad you came with me today."

Was I reading him wrong or was he suggesting he would be my sex slave? I would soon see by trying something totally different.

"Dave, my ex wife and current girlfriend won't let me fuck their ass. I would like to fuck yours as soon as I recharge and am ready for action again."

Once again he fell to his knees in front of me and took my cock back in his hand and then fed it to his mouth so just his lips were holding it. This guy sucks a cock so well maybe I could have him give my gal-pal some lessons! He was running his fingers up and down the veins of my shaft when it started to come to life again.

"Dave. I have only had it done to me once before and that was only part way up my ass. Would you let me put some lube on your cock to make it easier on my ass? I brought some with me hoping I would get this chance for you."

"Sure but don't cover me with the stuff. I hate the mess Vaseline causes. And Dave, I am going to warn you now. I will be driving it all the way up your ass. That part way stuff doesn't interest me at all."

"OK Chuck, just go slow at first OK?"

"Sure, that's the least I can do for an ass as sweet as yours. Now take this thing in your mouth and get it hard and then lie on your back. You can jack yourself off as I am fucking your ass."

"Oh God, this is going to be so great." He moaned.

He soon had my cock covered with lube and was on his back with his legs in the air and spread wide.

"Dave, here it comes. I am going to slip the head in you a little."

I thrust in just a little up to the ring around the head of my cock and his tiny little asshole opened just a bit trying to accommodate me. He squirmed a little and grabbed his own cock.

"Ready Dave? I am going to drive this thing all the way home."

"Oh yes, Chuck, just go slow. Aaaaaahhhhhhhhhhhhhh. Oh my God, that hurts a lot. Are you all the way in me?"

"Not yet but here it is," as I rammed it all the way.

"Oh Chuck, that really hurt. Does it feel good for you?"

"It feels just fine." As I started to pump his ass. He couldn't take his eyes from my face nor his hand from his own cock.

It wasn't long before he was beating his cock to death. I was pumping as deep as I could and then coming almost all of the way out before resuming my inward drive. It felt terrific for me and it was appearing he was enjoying himself as much as I was.

"Oh Chuck, I am going to come. I can just feel it."

"Well, you better spray it all over yourself and not get a drop on me."

"Oh, I'll cover the head of mine with my other hand so none of it hits you."

Before he could get those words out of his mouth he was throwing his hips in the air as he was shooting his load into his free hand.

"Oh my God, I must have had thousands of orgasms but none like that one." He shouted.

"Glad you enjoyed it now do everything you can to make me enjoy mine."

I could feel his sphincter muscles tighten and didn't know whether he was doing that or if it was a natural reaction of his rectum to having a cock ramming deep inside of it. Either way, it was grabbling my cock tighter than any pussy ever did. He was throwing his ass up to stay in perfect synch with my thrusting.

"Dave, get ready. I am about to unload deep in your ass," as I thrust even harder into him.

"CHUCK, go easy."

"Easy hell, I am unloading right now." And with that I started to shoot a decent stream inside of him.

I wrapped my arms around his upper thighs pulling myself in as I let go and all he could say was,

"Oh yes Chuck, it feels so good for me. I hope it did for you too."

"Yes, it was great Davie."

"Ooooh, he called me Davie. My mom used to do that. It sounds nice."

"OK. I'll call you Davie every time I shoot a load up your ass."

"Is that a promise?" he asked laughingly.

"Yes, now how the hell am I going to wash off here in the boat."

"Oh, I never showed you the head. It has a shower with hot and cold water. Just like home."

Sure enough I was soon covered with a soapy lather and Davie stuck his head in. "Out, and let me shower in peace." I yelled.

When I finally emerged from the head he was pouting. "What the hell is the matter with you?" I asked.

"Sure, I let you fuck my ass and then you want nothing more to do with me." He moaned

"Oh shit, you sound like some teenage girl. 'I let you fuck me and then you turn your back on me.' For God's sake grow up Dave. You gave me a blowjob, I fucked your ass and then needed a shower and now you are pouting. Stop it now or it will be the last time you will ever see my cock.

"I was just hurt when you yelled at me to get out of the shower with you."

"Yes, I was finished with sex and was getting ready for the sail back. Oh shit, Dave, you are acting like a possessive bitch and I don't want to have anything more to do with someone like you. Get cleaned up and get this boat back to the dock."

Oh hell, the tears started to flow. "Chuck, I'm sorry but I like you so much I can't stand to have you turn your back on me."

"Look Dave, go take your shower and we'll talk about this on the way back."

He jumped into the shower and was out in a few minutes drying off in the main cabin. I went out into the cockpit to stay away from his sobbing. He was soon dressed and giving me the instructions of how to get the anchor up as he motored the boat around to head back. The wind had come up a lot while we were anchored and he just unfurled the front sail for the trip back. It was blowing too hard to have both sails up.

I started the conversation I knew he was waiting for. "Dave, we had a nice time today. The sail over was fantastic and something I really enjoyed. I told you it was my first time sailing and I learned a lot about it from you. The swim was refreshing and the sex was unbelievably good. I know you like me a lot and while I can't say I am as enamored with you as you seem to be with me, I know we will be seeing each other around the office. I'll probably come over to your place every time I want to fuck an ass or get a good blowjob. We'll have to see where it goes from there. Is all of that OK?"

"Oh that sounds wonderful Chuck. Are you still going to be seeing your girlfriend."

"Yes I will. Nothing happened today that would make me want to drop her sweetness or opportunity to suck some tits or eat some pussy. That is a meal I really enjoy."

"Now Davie, I am going to lay down the law to you. If you want to continue seeing me sexually you will have to drop every other guy you are sucking or let fuck your ass. I am not going to risk any disease because of your promiscuity. If you can't live with that just tell me now and we will part friends."

"Oh Chuck, I haven't been with anyone else for months. It has been all that time I have been dreaming of making you happy and I jack off almost every night thinking about it. If you remember, we had a department photo taken a month or so ago and I had your picture in it blown up and it is on my wall above my bed. I will absolutely promise to be completely faithful to you and your cock."

Wow, this guy has it bad for me and I am hoping it isn't going to cause any problems, particularly at work.

The sail back was very pleasant. The wind stayed right about the way it was when we left the anchoring spot and we fairly flew home. Everything went about normal at work with Dave only making a couple of suggestions that I drop in and see him sometime soon. I came up with a few excuses and things went on as they were.

Strangely, I was with my gal pal Cindy a week or so later and the conversation, as usual, got around to sex. Out of the blue she started talking about what a gay guy does for another guy. One thing led to another and I asked her if she would like to see it for herself. Her eyes lit up and she almost jumped up saying,

"Are you serious. Can you arrange it for me to watch a guy suck off another guy?"

"How about it if I arranged for you to see that as well as the gay guy take a cock up his ass?"

"Chuck, I'd love you forever if you could." She said almost bubbling with excitement.

"OK, Consider it done."

"When?"

"Geez, nothing like impatience."

"Well, you were the one who offered it." She said with a long face.

"OK love, C'mere and drop your lovely pussy on my cock and I'll arrange it soon."

We fucked long and hard most of the night and I called Dave in the morning telling him what I wanted.

"Chuck, I'd feel like I was an exhibit." He moaned.

"Oh shit, forget it then. First you tell me you want to do anything to make me happy and the first time I ask you to you refuse. You are full of more shit than a Christmas turkey." And hung up the phone.

It rang back in a few seconds with him saying that he was sorry for being the way he was and of course he would suck me off and let me fuck his ass as my girlfriend watched. We set up the date for the next night. Now the question was if I was going to tell her that it was me who would be getting the BJ and fucking the guy's ass or wait until the night of the event.

It was decided we would meet at Dave's apartment and Cindy and I showed up right at the appointed time. Dave invited us in with a glowing smile and offered us wine of our choice. He must have stocked up for us for he must have had a half dozen bottles sitting out waiting to be opened. "We'll both have a glass of whatever white you have handy Dave."

The three of us sat around chatting for a while with Cindy I'm sure waiting for the other guy. It was up to me to make the announcement.

"Cindy, do you remember me going sailing a couple of weeks ago? Well it was Dave who owned the boat. What I didn't tell you was that Dave is gay and he gave me a BJ and I fucked his ass while we were swinging around on anchor. I'm the guy who you are going to see get blowed and do the ass fucking."

You could have knocked her over with the proverbial feather. "You must be shitting me. Did you suck him and let him fuck your ass too?"

"No, No, NO. I just let him do his stuff other than having me fuck his tight little ass."

"Geez, I am so excited I can hardly talk. Dave, are you going to suck his cock and let him fuck your ass tonight?" she asked breathlessly.

"Yes, Cindy, if that's what you would like to see."

"Holy Cow, I can't wait. What's taking you guys so long?" She asked.

Dave came over and dropped to the floor in front of me and reached up and put his hand on my crotch. He rubbed it up and down before unzipping my jeans and letting my cock out. It wasn't out a few seconds before he had dropped his mouth on it taking it all in while it was still soft.

"Holy shit. Dave, you have it all in your mouth." She exclaimed.

He had one hand rubbing my balls through my jeans as his head started to bob a little as my cock was rising to the occasion. Cindy couldn't take her eyes off what he was doing and actually had her face down very close to see just how much he was getting buried in his mouth. It wasn't long before I was hard as steel and Dave was starting his bobbing action. He is able to take at least five of my seven inches in his mouth and uses one hand to grab the base of my cock that isn't in his mouth. Cindy reached over and was holding my balls as he was doing his thing on my cock.

"Chuck, you are going to have to fuck my lights out soon for I'm hotter than I have ever been."

"Hold on baby, I'll be shooting a huge load down Dave's throat in a minute."

"Oooh, I would love to see you shoot it in his mouth. Can you take it out and have him open his mouth and then shoot in it?

"Dave, let's give the lady what she would like to see."

He pulled off of me and I lined up and had her jerk me off with the head of my cock an inch away from Dave's waiting mouth. She could feel my cock pulsing and knew it was about ready to unload and she started to jerk me faster. When I did unload she almost had on orgasm herself.

"Geez, keep shooting Chuck. You almost have his mouth full." She screamed.

"Keep jerking baby." I answered.

By the time I was finished coming she was all over me and breathing faster than I had ever seen.

"Do me" she yelled.

"Honey, I am going to have to eat that lovely pussy now until I get recharged. Drop your pants and panties."

She threw herself back on the sofa and had her red hot pussy staring at both of us. It didn't do a thing for Dave but it sure turned me on again. I dropped to my knees in front of her and by the time I got my face about an inch away from her waiting pussy lips she had her hands wrapped around the back of my head and was pulling me in so hard I couldn't have escaped if I wanted to. My tongue found her clit and was working it fast and furious when I folded some fingers tent fashion and started to finger fuck her. That was all it took. She was throwing her ass up at my face and hand and I could feel the muscles in her vagina closing around my fingers.

"Oh hell, here I come. I am coming too soon Chuck. I wanted it to last a lot longer." Her juices came pouring out of her as her breathing came back somewhere near normal.