Sometimes life just takes little turns when you least expect them and the outcome while often pleasant can be very surprising. This is a hard story to start because it had no real beginning or significant ending. The middle part however was very nice.
I'll start with a little history to set the circumstances and to explain how a story can exist without really beginning or ending. I'm in my middle fifties and through good fortune managed to find myself divorced with enough money left to retire comfortably. After selling my house I decided to try living on a boat on the west coast. After finding the type and size I wanted I set about on my labor of love and began restoration. At this point she is very livable, quite comfortable and affords the peace and quiet that I like. With space at a premium my toys are limited. I do however like good wine, good food and enjoy cooking to share with my friends. I do eat off paper plates sometimes but when I have guests we use real wine glasses, crystal cocktail glasses and stoneware plates with real silverware. My orientation while lacking in experience would be classified as bisexual.
The next explanation concerns one of my friends. Mike and I go back many years and have traveled, worked and played (mostly golf) together. He is a little younger being in his early fifties and has always managed to look ten years younger than his age. Our conversations over the years have managed to cover a lot of territory including some personal things regarding sex. He has confessed to liking to be spanked on his bare ass and even admitted to having had a finger or two up his ass, although claiming they were female I'm not sure. For my part I have admitted to having bisexual tendencies and have in a drunken stupor actually offered him a blowjob which he never really declined. As to size, he claims to be average and I wish I could make that claim.
He had agreed to come over for dinner on Friday night and since we often will have too much to drink, he usually stays over and leaves in the morning. I'm not sure why but I was very horned and decided to take a run at him again. Other than the obvious preparations I had left my laptop on the galley table. Being late fall the idea of sitting outside on the deck was not appealing and we settled inside with a beer.
I controlled the conversation around to his sex life which for the most part was usually in turmoil having been married and divorced three times and getting stuck with outrageous child support. When I asked if he was getting laid he just said not as much as I would like! I managed to steer the conversation to old times and some of our talks about sex. I reminded him that he said one time that he enjoyed a good bare ass spanking which just made him laugh. I figured the hook was set and proceeded to tell him about some spanking videos I had downloaded from the internet. He expressed some interest and I pointed out that the computer was still sitting on the table in the galley. His response was what the hell lets take a look.
Logging on took a couple of minutes which gave him time to open another beer. I went to the directory where I had stored the files and decided to start with pictures of boarding school girls getting spanked bare assed with a paddle. He stood next to the built in dinette and leaning over to see the LCD screen. So far this was all going according to plan and I slid over suggesting he sit down, which he did. After a few of the more mundane displays I moved on to the pictures of completely naked girls getting caned. These of course were accompanied by a lot of crying and screaming. Now keep in mind that when on the boat I usually just wear loose sweat pants and will often go without under ware. This was the case tonight.
After a few more of the caning pictures, I remarked that I'd bet his pants were getting a little tight to which he just laughed and said I don't think anyone could watch these with out that being a problem. He then pointed out that it would appear I had a little tent in my pants as well to which I commented that at least I had room to grow. After I suggested that he might want to unsnap or risk tearing something he said yeah you would really like that wouldn't you. My opening was here and I reached over and run my hand lightly up the inside of his thigh stopping short of his crotch. When he didn't react, I loaded a video of a guy strapped to a bed on his knees getting fucked by a girl with a strap on. As this caught his attention I moved my hand up to his crotch and offered to loosen his pants so he could be more comfortable. As I squeezed his package, which indeed was stuffing his pants, he just whispered a very quiet ok.
As I undid his belt and unsnapped his jeans I felt his hand move to the inside of my leg and slowly move toward my tented sweat pants. His zipper was down in seconds and my hand slipped into his pants with only his jockeys between his prize and my hand. I quickly loaded a new video showing a guy completely restrained and being whipped by a woman in leather which although not my thing seemed to get his attention.
We were both into what we were doing but did take passing note of the activity on the screen. It was at this point I looked over at him and realized that his eyes were closed and his mouth had dropped open causing him to make small gasping sounds. Moving on, I found the top of his jockeys and worked my hand inside feeling his very hot cock. It was only seconds and his hand slipped into my sweats and was massaging my shaved balls and leaking cock. The video had run out and I closed the laptop shutting it down. It seemed moaning was the order of the day and it was coming from both of us. His finger kept tracing over the tip of my uncircumcised cock playing in the wetness that he was causing. I opened my eyes to see him watching me and slowly moved my lips toward his. As our lips lightly touched, I whispered that if we were going to do this we should try it all and then traced my tongue lightly over his lips which soon opened to the invasion. Knowing that I had him, all I needed to do now was take my time and go slow.
I asked him to let me out so I could do something. As I stood, he roughly grabbed my crotch squeezing lightly and said hurry back I'm not done with these. I moved to the main part of the cabin where I secured all of the hatches and closed the window coverings. I then pulled out a sturdy teak bench and placed it in the center of the area and pulled down a two foot long piece of finished oak that I had cleverly disguised as a support for my working life jacket suspended from the ceiling. Hidden from view were a box of latex gloves (common on boats) and a large bottle of clear KY (not sure how common) lube. I sat on the center of the bench and asked him to come up from the galley.
When he saw me sitting there with the strip of oak in my hand all he said was, what the hell? I just smiled and told him to kick off his shoes, he was about to get a spanking. As he stood looking at me, I told him again to kick off his shoes. He questioned why and I explained that he had to remove his shoes so he could remove his pants. Oh fuck, I don't know about this was all he said. In a firm voice I repeated my instructions and he slowly responded by removing his shoes. Standing bare foot, I then said now the pants. As they dropped, I could hear an increase in his breathing and noticed his jockeys start to fill by a full blown stiff cock. To know that this was exciting him was an even bigger thrill for me. He stood for a minute looking at me with very large eyes giving the impression that at any moment he might change his mind. His look changed very quickly to panic when I said now it is time to lose the jockeys. Raising my voice, I said NOW! He hooked his thumbs under the sides and turned sideways slowly pulling them down over his hips. My prize was exposed. His cock stuck up at about a 20 degree angle, was straight as an arrow, smooth without veins with a perfectly sized tip for its size. In short, it was about six and a half inches of perfect man.
Maintaining a voice of authority, I told him to get over here and lay over my lap. He slowly moved toward me with a very uncertain look on his face. When he reached the bench, I just pointed to my lap and waited for him to comply. As he started to adjust his weight, I spread my legs so his cock was positioned between mine and closed them to put pressure on his very hard member.
OK Michael, you're doing very well, now spread your legs apart. When he questioned why, he was told to just do it now. I asked him when he last got spanked and he said it was a very long time ago. I told him to try and relax and slow his breathing or he would hyperventilate and pass out spoiling all of the fun. I explained that this was not all about pain and that he would get to experience both pain and pleasure before we were done. As I told him this my hand was caressing his smoothly shaved ass. With his legs spread I could easily trace a line with my finger down his crack over his "very tight" pucker and on to his drawn up balls. At this point his breathing was in gasps with long periods of not breathing in between. When I asked if he liked it when I touched his exposed hole all I got was a very feeble barely audible whimpered yes oh god yes.
It was time to move on and I picked up the strip of oak. With one firm whack I hit his ass dead center making him jump. As I massaged his burning butt with my hand and allowing my finger to make the familiar trip down his crack, I asked how many of those he thought he could take. His response was I don't know. OK fine, for being an indecisive wimp, you will get twenty in groups of five. In between those groups I'll deliver some pleasure.
I proceeded to deliver five blows in a row causing him to cry out on the last one. I pulled on a latex glove, the sound of which is unmistakable, and squeezed a large ribbon of lube into his crack. Tracing the line down over his tight hole and lubing the route, I just lightly tickled and massaged him causing an involuntary moan of pleasure. Since I wanted to limit the pleasure I quickly stopped and struck five more blows causing him to cry out with each one. Stopping again, my finger traced the valley of his exposed crack only this time on arrival at his hole my finger just stopped. With very light pressure I told him to relax and let me in if he wanted to feel good. Strangely I heard a slight sob as his ass relaxed allowing my finger entry. Stopping at the first knuckle I slowly rotated my finger and pulled at his hole causing him to stop breathing. As I removed my finger, there was a very loud gasp as he took in air. I truly think he had no idea what to expect next on this wild ride. Again five more quick blows and with his ass starting to redden a bit his vocal level increased in proportion to the increase of color.
My finger again took the predictable route down his crack to his now well lubed but still tightly pucker hole. Again his breathing came to a halt as I lightly pushed to gain entrance and again had to tell him to relax so I could get in and give him pleasure. This time I found that magic spot and lightly massaged it causing him to involuntarily hump at my closed legs. As I realized what he was doing I spread my legs preventing the friction he was so desperate to find.
Removing my finger quickly I administered five more quick blows to his now cherry colored ass and getting the response of fucking hell I'm so glad that is over when I finished. He was puffing and I could hear him sniffing so I knew he had some tears in his eyes from the spanking. No bruises, just a very hot ass that he will remember for a while.
I spoke in a soft voice telling him we were not quit through but the rest would be a lot more fun. With a bit more lube, my fingers started that now very familiar trip down his crack to his very sensitive hole. Just to fuck with him a bit, I stopped short and reached between his legs with my other hand and squeezed his balls gently making him moan. My finger then continued on until I found the warm soft spot and pushing. This time entry was welcome and his breathing became very rapid. As I stroked his prostate he started making cooing sounds until in one convulsive movement he exploded in a giant orgasm nearly biting my finger off with his ass contractions. My massage of his prostate was relentless causing even more contractions of his ass. At some point they stopped and he begged me to take my finger out.
After removing my finger he lay on my lap gasping for air saying time after time OH FUCK, OH FUCK. As he got his strength back he stood and I saw a very inflated cock hanging straight down with cum dripping. I couldn't help myself and reached out and pulled it toward my mouth to lick the remaining remnants of one very explosive climax. In looking down at my sweat pants I realized that this guy had just shot a world class load all over me.
He stood for a moment and then asked if he could lay on my bunk for a little bit. Thinking he just needed a rest before the next round I said sure but only if I can join you. We lie quietly on the queen size master suite bed for a few minutes and he said nothing. He finally stood and went to retrieve his clothes which he put on.
Remember, I said no beginning and no end to this story. When he got his clothes on he stuck his head in the hatch and said "hey man, I got to go, I'm getting married this weekend".
I heard the outside hatch close and as I lie on the bunk covered in his cum I'm saying, FUCK ME, FUCK ME, FUCK ME, that son of a bitch!