My friend Mike and I had decided to spend a week boating in late September in 1999 mostly because we had been working hard and had done the family vacations earlier in the year. We both had vacation time left and both enjoyed sailing so we chartered a thirty six foot sloop and got supplies for the trip. Since it was kind of a last minute idea we were scrambling to get everything ready. By Saturday we had it together and left for the marina to load the boat and take off.
Using the dock carts we finished loading in about an hour and had all of the supplies on board along with our personal gear. The weather was great and we sailed steady for about eight hours before finding a quiet secluded cove with no other boats and dropped anchor. After securing the boat Mike looked at me and said how about a drink? Now that sounded like a great idea and he got the vodka and ice and asked if I would like a screw driver. Only if you mix it half and half I said.
We relaxed in the cockpit and enjoyed what was left of the daylight and pleasant temperature. We started chatting about our lives and discussion led to what we would have wanted to do different. It seems we were both quite happy and satisfied with our lives. After the second drink Mike asked me if I was happy with my sex life. Now this is not a subject I would normally discuss with a guy but Mike and I go way back and have socialized for years. I said that sometimes I get bored and wish I could try something different. He agreed saying that his wife is the basic missionary woman and refuses to do anything oral or anal. He was joking but said maybe we should switch wives and at least get some strange stuff once. We both laughed knowing that was not going to happen.
It was time for dinner and we broke out the steaks and potatoes we brought for dinner. We finished cooking and ate inside the cabin but after we had cleaned up we took some brandy and sat on deck watching the moon. Mike was somewhat quiet and I finally asked if something was bothering him. He said he was thinking about sex again and we both chuckled. He was quiet for a while then asked if I had ever done anything with a guy sexually. I said no but if he was making an offer I was horny enough right now and might try it and again we both laughed. He went on to say that sometimes he wonders about what it would be like to try sex with a guy and admitted that he sometimes masturbates thinking about a guy touching him. Now it was my turn and he asked if I had ever had thoughts of touching a guy or having someone touch me. I guess he took the pressure off me when he admitted to having such thoughts so I said that I had the same thoughts and had even masturbated to them. I explained that I have fucked women up the ass and have gotten blow jobs but there are two things I have never had the opportunity to try. I went on the explain that I have always wondered what it would be like to have a guy cum in my mouth and what it would feel like to have a guy fuck me up the ass. Wow he said I guess I'm not so weird after all.
It was getting late and we decided to go inside and go to sleep. As I passed Mike he playfully patted my butt and said nice ass any chance of getting some of that? Again we both laughed but you could feel the tension building in the air and Mike seemed to be leading the charge to a new adventure.
I was putting away the dishes as he walked behind me and had to rub against me to get by. I said I'll give you twenty minutes to stop that. There was no laughter and he backed up and with his feet between mine pressed hard against my ass with a half hard cock saying that it won't take twenty minutes. Suddenly all of the electricity in the air was focused on my cock. I started to stiffen but said nothing and he pressed a little harder with his hardening cock causing my cock to tent out the front of my shorts. As he pushed his now hard cock against the crack of my ass I moved my feet apart spreading my legs further. I could feel his stiff hot cock pressing against my hole through my shorts and realized that neither of us was wearing under ware. There was a lot of heavy breathing and even a little moaning but still nothing was said and he moved his hands from my hips up under my shirt where he found and pinched my nipples hard making me moan. He was rubbing up and down my crack against my ass with his hard cock and I thought one of us would cum if he kept it up. He then slid his hands down over my stomach to the front of my shorts touching my cock which by now was rock hard poking straight out and soaking the front of my shorts. He slowly stroked my cock through my shorts causing me to moan and move back against him. He finally broke the silence by saying that maybe we were about to enjoy our fantasies. While he was kissing and talking into my ear he slipped his hand inside of my shorts touching my cock making me gasp OH Fuck! After a few minutes of rubbing and moaning he put his fingers in the waist band of my shorts and forced them down until they stopped because of my spread legs. I moved my legs closer together and they dropped to the floor where I kicked them aside. When I spread my legs apart again I felt him move against me and I suddenly realized that he had dropped his shorts and was pushing his hard cock against my exposed hole. His cock was leaking profusely and was coating my hole with his slippery juices. As he pushed harder I said "no we can't" but at the same time I leaned forward putting my arms down on the counter top and relaxed my hole allowing his cock to slide up my ass. Although I was expecting pain there was none and even with his pelvis pushing against my butt everything felt incredible. As he slid slowly in and out I could feel the fullness and the gentle massaging of my prostate. We were both making sounds of sex and didn't want to stop. After a few minutes of this my breathing got raspy and I told him if he didn't stop I was going to cum. He whispered in my ear that was kind of the idea and reached around and gently squeezed my balls. That was all it took and I groaned sending several shots of cum against the cabinets and covered his hand. As he realized that his hand was sticky with my cum he pushed harder at my ass and I felt his cock getting bigger and realized that he was shooting cum up my ass. He just backed away and said well now you know what it feels like to get butt fucked so it looks like there is only one thing more we need to do. I stood leaning against the counter with my legs still spread trying to take in what had just happened and replaying it in my mind. I was brought back to reality when I felt his cum running down the inside of my legs making me clench my ass together to stop the flow. I found my shorts and quickly pulled them on and headed for my stateroom.
I couldn't get the thought of touching his cock and the feeling of his cock slipping in and out of my ass out of my mind. I tossed and turned for about two hours thinking about the things we had said and done and finally got to sleep. In the morning we fixed a quick breakfast where nothing was said about last night and set sail for the next harbor which was even more secluded than this one. At one point I finally asked if what happened last night had bothered him and for what ever reason he said no he found it very exciting and interesting. On arriving at the next harbor we found a mooring buoy and secured a line. It was only about three and the September sun was quite warm. Mike asked if I would mind if he took a shower on deck and I said not a problem. I sat in the cockpit reading while Mike set up the sun shower bag in the rigging. He stepped out of his shorts and turned the shower on to wet himself. He then proceeded to soap up and wash his hair. Now after what happened last night I couldn't help but take a peak while he had his eyes closed washing his hair. Mike was nearly hairless except for pubic hair and some under his arms. His tan was dark except for the swim suit lines and I did notice that he shaves his balls and trims his pubic hair. His cock was maybe three inches soft and cut. I looked too long and he caught me looking smiled and started stroking his cock slowly making it firm up and making mine harden as well. When he was hard he asked if I would like to help him wash anything. I said maybe later. He rinsed off and dried and pulled on his nylon shorts.
As he walked past me to get us some beers I noticed the outline of his semi hard cock through his shorts and started to harden again. When he returned he sat directly across from me and spread his legs allowing me to look up his pant leg at his cock. As he drank the beer he seemed to get bolder and stroked his cock making it harden and asked me if I was getting a hard on watching him play with himself. He went on to say that it was too bad we stopped last night because he thought he would finally get to experience all of his fantasies. I said it is never too late. It was like he was giving me permission to do anything I wanted while he remained passive. I figured it was time to get him to do something beside talk.
It was getting pretty clear that we both wanted something more to happen between us and I was starting to feel this was my chance to live out my fantasies. He stood to go get a couple more beers and as he passed in front of me I reached out and grabbed his leg stopping him. I started to run my fingers lightly up the inside of his leg and he asked what I was going to do. I said I was willing to do anything he wanted but right now I just wanted to see if his cock felt as good as it looked and continued running my hand toward his crotch. When I got to his crotch I let my fingers slide up his open pant leg and touch his bare cock. I pulled my hand out and cupped his package in my hand gently squeezed and made him moan. I moved my hand up his shorts and when I got to the top of his waist band I slipped my fingers in and slowly pulled his shorts down in one movement exposing his now fully erect six inch cock. He stepped out of his shorts and threw them into the cabin. Starting at his knee I again ran my finger nails lightly up the inside of his leg reaching his balls I fingered them lightly causing them to pull up tight and finally found my way to his cock which I slowly stroked making him take short gasping breaths of air. I moved forward on the seat until my face was inches from his crotch. When he realized that I was offering to suck his cock he leaned forward touching my lips with the end of his cock. My mouth opened and he slid slowly in until he hit the back of my throat. Never having given a blow job before I was surprised my mouth seemed to instinctively know what to do to give Mike maximum pleasure. In seconds he was fucking at my mouth and moaning. I reached between his legs and massaged his balls and let my finger trace back to his puckered hole lightly brushing over it. I could feel his cock swell and his pace quicken. Oh fuck he said as his cock erupted and poured long ropes of hot salty cum into my mouth making me swallow several times. As he finished he just fell back against the other seat and sat with his shrinking cock staring at me for a few seconds.
When he spoke I was afraid he was going to be remorseful or angry but instead he said that was fantastic and now you know what it feels and tastes like to have a guy go off in your mouth. He suggested we go below so he could return the favor. As we headed for the forward cabin he reached around and rubbed the front of my shorts feeling the wet spot and squeezing my hard on. He asked if it excited me to suck his cock. I said that considering that you have your hand on my hard dripping cock what do you think? On reaching the cabin he pulled my shorts down and turned me around and pushed me onto the bed. It seemed he was in as big a hurry to do this as I was. He quickly went to his knees and took my cock in his mouth. Being slightly smaller than Mike he had no trouble taking me all the way into his mouth. He used his tongue to rub against the bottom of my cock as it slid in and out. I finally asked him to stop because I was about to cum. Why do you want me to stop? I told him I wanted to kiss him and he crawled up on the bed next to me, our naked bodies touching, and gently put his lips against mine opening his mouth for my tongue and we had the hottest kiss I could ever remember. The fact that I could taste my cock in his mouth and he could taste his cum in my mouth made it even more exciting. I finally pulled back and told him that I wanted to feel his cock up my ass again.
From the night stand I retrieved some condoms and lube and turned to hand them to Mike. By now my cock was no longer hard and he grabbed it and stuffed it into his mouth making me hard in seconds. I gave him the lube and condoms and said I'm all yours, how do you want me?
He said he wanted me on my back with my knees pulled up so he could watch my face as he lubed my hole. I rolled over and pulled my knees up and he traced his finger tips over my ass and up my crack until he reached my quivering hole. He squeezed the tube and I felt the cold feeling and then his finger was gently teasing my exposed hole. He slowly pressed until it opened and his finger slid in telling me that this was going to feel better than it had the first time. He applied more lube and did the same several times teasing me for what seemed like hours. My hole was so slippery he added a second finger and continued making me moan every time his fingers entered. His eyes were focused on my face so he could judge my reaction to what he was doing. He found my prostate and gently stroked it with his finger tip making me gasp and my cock to release a large dribble. My cock was dripping pre cum and his was hard as a pipe again. I told him I wanted him in me now.
He put a pillow over the edge of the bunk and told me to bend over it and spread my legs. I didn't know how this was going to feel but just being in this position and knowing his cock was about to slid up my ass was about the sexiest thing I could remember doing. He stood between my legs and I felt his cock pressing against my hole until I relaxed a little and it started to slid in. When I felt his hair against my ass I knew he was all the way in and I had felt little discomfort. He started rocking back and forth slowly making my ass warm inside. After a few minutes of this he had a hand on each hip and was pounding into me like I was the best fuck he ever had. He stopped and said he wanted me to turn around so he could see my face while he fucked me. I turned over he put my ass right at the edge of the bunk and he put my feet against the bulkhead and stood between my legs reinserting his cock up my ass. This position was even better because at this angle his cock rubbed hard against my prostate every time he slid in. He seemed to enjoy this position as well and I could feel his cock getting bigger. He reached down and stroked my cock a few times and I exploded with several long streams of cum all over my stomach and chest. As my ass squeezed his cock he stopped stroking in and out and I could feel him pulsing inside of me shooting off his load of cum. He looked down at me and slowly pulled out his withering cock. It was then that I realized he didn't bother to use a condom and had actually filled my ass with cum just like he did last night.