I have a friend named Mark who I have known for many years. He has been divorced three times, me twice with both of us vowing to never do it again. We had worked together, drank together, played golf together and traveled together. Over the years we have talked about a lot of sexual things without being too specific but exchanging a lot of information. I had told Mark in one conversation that if you have ever had a girl stick her finger up your ass when you were getting a blow job, you could understand why a guy might like to get fucked up the ass. He just looked at me and took this without too much comment. One time he admitted that he liked to be spanked on his bare ass and another time said he had fucked a girl up the ass. He even told me that a girl had stuck her finger up his ass while they screwed. These conversations took place over several years and the impression was that he didn't like any of the ass play experiences, but I always wondered why he bothered to mention it if they were bad experiences. It was almost as if he were probing and testing my reaction to his comments.
We even discussed the size of his prick with him volunteering the information without my asking. It seems he is not large but has had girls comment that he was average, small and even large, so I am assuming that he must be comfortable with his size but that he is not John Holms. I on the other hand was born with the curse of the Irish, having a large head and rather small dick. This just lays the groundwork for what was to happen one Friday night when we got together for a drink on my boat. We immediately got into a conversation about how horny we were and how long it had been since we had sex or even gotten off. It seems Mark had been traveling as had I for the week and had not even had a chance to jack off for five days. Mark even pointed to a bulge in his pants and commented that all of this talk about getting off was giving him a hard on. After a couple of beers for Mark and a glass of wine for me he asked if he could use the head in the aft stateroom. I showed him the head and in the process of instructing him on how to use the marine toilet we touched and rubbed together in the close quarters which seemed to give us both a bit of a hard on. For me it was even more apparent since I was only wearing nylon warm up pants with no under ware. I told him that if we kept it up he would either have to buy me dinner or have sex with me. He just laughed and said why couldn't we do both. When he came out of the head I was still in the stateroom and he came over and said "you realize I was just joking, right". I said "as horny as I am that's too bad it might be fun".
This started a bit of high school grab ass with him going for my crotch and me going for his causing us to fall on the bed. It seems there was no resistance from him and I soon realized that he was letting me touch him and I could feel the outline of his rapidly hardening cock and noticed a visible wet spot on his pants. I relaxed and stopped resisting and let him feel me getting hard through the thin fabric. I gently stroked his hard cock through his pants and gave his balls an occasional squeeze while he did the same to me. There was no resistance and it was obvious that we were both enjoying the feeling of having the other guy play with our cocks. After a few minutes I decided that I wanted to see how far he would go and I unzipped his pants. As I slowly worked his zipper down and massaged the wet spot on his pants, his breathing became irregular. With his zipper all the way down I ran my hand inside his pants and rubbed his cock through his shorts generating "oh, fuck that feels good". He then slipped his hand in the top of my warm up pants making me groan softly when his warm hand came into contact with my cock.
It was again time to up the ante and I undid his belt and unsnapped his pants I then slipped my hand into the top of his Jockey shorts and felt his bare cock and balls with my fingers and was shocked at how hot and smooth it was. It was then that I realized that mike shaved his balls just as I do. I run my fingers over the wet spot on the end of his cock spreading his pre-cum around the tip. He soon did the same to me making me take my breaths in short gasps. I had to try one more thing and slid down on the bed and I started to pull his pants down so I could see his cock. He raised his hips to help, indicating his willingness to proceed, and his cock popped into view right next to my mouth which seemed to automatically open and take it in making him groan in appreciation. I sucked him deep into my mouth tasting the wetness and feeling his sex on my mouth and let him slid back out a few times. His hand pushed my head down forcing his cock to the back of my throat. This went on for some time and I could taste his cock leaking pre cum before we stopped and looked at each other with a confused look. I broke the ice by saying that I have always wondered what it would be like to have a guy go off in my mouth. He responded with lets find out right now. He wanted to get started but I told him this was going to be my way. I told him to take off his shirt while I pulled his pants the rest of the way off and took his shoes off. He is now lying there naked cock sticking straight up. I said I think you have been a very bad boy and you need to be spanked. I told him to roll over on his stomach which he did. I ran my hands over the back of his legs and ass causing goose bumps to form. This is when I realized that Mark shaved his ass and legs as well as his balls. I run my hands over his smooth butt and told him to spread his legs as far as possible. When he did this I could touch his tight hole and smooth drawn up balls between his legs causing him to moan and take deep breaths.
I found a thin piece of oak about two feet long. I struck his ass hard and he moaned a little and his breathing stopped, the next blow was even harder and he yelped. I said that is pain and slowly run my fingers down his crack circling over his puckered hole and rubbed his balls with the palm of my hand explaining that this is the pleasure. This elicited a loud groan and made him kind of whimper. We continued this alternating action with my finger pushing further into his receptive hole each time until I got to ten strokes when my finger was completely in his ass and I could feel his prostate pulse as I rubbed it. I figured he was about as hot as he could get and it was time to move on so I removed my finger from his ass and told him to roll over and he pleaded with me to do it five more times. I commented that he seemed to like having me finger his ass and he just groaned oh fuck yes. We agreed that we would revisit this activity again in the future and I wouldn't stop until he came. I slapped his ass and told him this was going to be on my terms and that if he came anywhere but my mouth tonight, I'd whip his ass with a belt and fuck him till he cried. He said that right now that even sounds good and reluctantly rolled over.
As I ran my hands up his body to his nipples I couldn't help notice that his cock was rock hard and dripping. This was clearly a man who needed to get off bad. I pinched and sucked his nipples for a few minutes making his breathing become short and irregular. It was time to finish him off and I slowly worked my way down to his crotch where his cock was rock hard and pointed up his belly. I was right about the size it was a little over six inches, cut and about the size of a large broom handle. I remembered thinking that I couldn't wait to feel that cock up my ass. I slid down his body and positioned myself between his spread legs grasping him behind the knees and pushing them up until his feet were flat on the bed with his legs spread wide. This of course gave me access to his ass while I sucked his cock. As I slid down and opened my mouth letting his cock slide in to the moist warm opening he just sucked in a loud breath of air and shook a little while I enjoyed the taste of his dripping cock. I kept up a slow pace allowing his cock to come into contact with the back of my throat and then slide nearly out of my mouth before taking him all the way back in again. I let my middle finger of my right hand brush against his exposed hole making him moan and shudder. I reached for a small container of lube which I dipped my finger into and proceeded to circle his hole making it slippery. He was now making audible sounds of pleasure and was trying to fuck my mouth. I could tell he was about to go over the edge and gently pushed my finger into his hole making contact with his prostate. He made some animal sounds his cock swelled and exploded shooting several large hot streams of cum filling my mouth forcing me to swallow. His ass clamped down on my finger and I could feel his prostate pulsing against my teasing finger.
Each time I pushed at his prostate it would spasm and his cock would shoot another stream of cum into my mouth. I'm trying to remember each detail of the experience and was mentally noting that each time he shot a stream into my mouth I could feel his cock swell. The taste was salty and sweet and the texture was almost like hot Jell-O, melting as it hit the inside of my mouth. As his climax ended, I let my finger slide from his ass and raised my head to see him looking down at me. I slid up his body to kiss him and when our lips met his mouth opened and we shared what was left of his salty sweet mixture.
We lay for what seemed like hours before he finally spoke. You know that was incredible. No one has ever made me feel that good. I should tell you that in college I had a roommate and we traded off blow jobs and some butt fucking because it seems we were both horny all the time and didn't have the time or money to be out chasing girls.
This led to a discussion about things I might be willing to try including some bondage and mild pain. We even discussed finding another guy to join us in a threesome. I guess the next move was mine since I had a hard on and still needed to get some relief. I reached down and starting playing with his cock. He touched mine and we started kissing again but not for long, he slid down on the bed and took my cock into his mouth and gently sucked. I was close to Cumming and asked him to stop because I wanted him to fuck me.
After I had retrieved a bottle of lube and a condom he told me to lie on my stomach and spread my legs and he would show me what he liked best from his college roommate. When I did he told me to spread my legs wide and rise up so he could slide a pillow under my middle. He then reached up between my legs and pulled my cock and balls back so they were pointing back between my legs. He then told me to put my legs together. This put pressure on my balls and held my cock in place. He started running his hands up and down the backs of my legs touching my cock, balls and ass lightly with his fingers. I was going crazy and my cock started dripping.
Clearly this was not the first time he had done this. He picked up the bottle of lube and said I think it is time to fuck. He lubed his finger and started making circles around my hole pushing harder and harder with each circle. As he slid over my hole it was as if it just reached out and pulled him in. I remember thinking wow he really has large fingers. He slowly worked his finger in and out adding more lube until I thought I would explode. He stopped and rolled on a condom and applied some lube.
I am so hot I'm almost crying for him to fuck me. I was not sure how he could do it in this position but he moved up to my butt straddling me. I felt him pull my cheeks apart and felt his hot cock pressing at my hole and I relaxed as he entered with out any pain. He would pull almost all the way out and then plunge back in rubbing my prostate with each stroke. Having his shaved balls rub against my balls and cock when he pushed all the way in was heaven. I was making a growling noise in my throat and could feel my orgasm building. When it finally hit I made strange sounds and shot streams of hot cum over his balls and my legs. This was a turn on for him and his pace quickened and I could feel his cock growing and his pace quicken as he shot his load groaning loudly. The intensity of his pounding and orgasm caused my prostate to pulse and my cock to fire off a couple of short spurts that ran down my leg. Mark pulled out and removed the condom and wiped cum from his nearly flaccid cock and gave a long sigh.
He looked at me and took his finger and run it through my streak of cum on his balls and then stuck his finger in his mouth and sucked. He looked at me again and smiled taking his finger again ran it over my balls scooping a gob of cum and then sticking his finger into my mouth. I sucked and licked his finger clean and realized that in spite of the fact that I had just gotten off, I was beginning to harden again. Mark noticed and said you have got to be the horniest guy I have ever seen. He got a towel and wiped my legs and balls clean playing with my nearly erect cock in the process.
We looked at each other and he said next time we get together I think I want you to fuck me and we can play by your rules. My cock was now completely hard and he offered to suck me but only if he could do it the same way as I did him. I agreed and he reached over and picked up the piece of oak and told me to roll over onto my stomach. I figured out that I was about to get my ass spanked and my cock just got harder.