My friend Bob had been having a tough time with his personal life and had started drinking a bit. Having been friends for many years, I would invite him over for dinner on occasion where we would drink a little too much and get into discussions about sex, women and work. I should point out that I have always had a curiosity about sex with another guy. This started when I was about thirteen and with the exception of one groping session on a camping trip nothing ever happened.
After finishing lunch one day at a local restaurant I stopped at a store and picked up some steaks, chicken and various vegetables to last me through the long New Year weekend. On the way back to my boat I thought, what the hell I'd give Bob a call and see if he had dinner plans. I happened to catch him in the office and he said that sounded great he would be there around five.
I should point out that Bob and I are both single having been divorced about five years. Our history goes back to the 1970's and we have stayed in touch and even worked for the same company at times. I guess we know each other very well and have even shared some of our personal stories which I don't do as a rule.
He arrived and said he wanted to walk up to a nearby bar and buy a few drinks and I pointed out that I had just about anything he would want on the boat. I have lived on a boat for the last three years and am in the process of restoring the old gal. At this point it is very livable and when Bob comes over I always make it clear that he can stay in the forward cabin for the night, which he does.
We proceed to drink a bit and talk about his latest problem relationship with his girlfriend. It seems Bob has always had one problem or another with women and I am his sounding board and advisor which I am comfortable with. We talk about just about everything and finally decide that it is time to eat. I BBQ some steaks, we have a salad and ravioli and adjourn to the aft deck with a couple of big Crown Royals on ice for a night cap. After an hour or so, we head inside to watch the national news before going to bed. I should point out that at this point we both had several drinks and finished two bottles of wine with dinner so were both more than a little drunk.
Since there is only one chair that faces the TV I sit on the floor and let Bob have the chair. The news is boring and we start to discuss sex again with the subject drifting to early experiences and the bisexual thing. I'm sitting next to his chair on the floor and when we get to the bisexual discussion, I said that I think that we are all that way to some degree and that I know I am, trying to get him to relax. At some point to prove my theory I run my hand up over his thigh to the inside of his leg. Expecting him to react and tell me to get my hands off, I was very surprised to have him lie back in the chair, close his eyes and spread his legs apart seeming to invite further contact. Considering how much we had to drink, I'm thinking holy shit he doesn't seem to mind and figured in for a penny in for a pound. I moved my fingers lightly up the inside of his thigh until I reached his crotch and started to gently massage him. His eyes were closed and he seemed to enjoy having me touch him. This was very frustrating because I really couldn't feel his cock so I just tried to cup his package and gently squeezed. As most guys know, even when you're drunk it feels good to be touched in a sexual way. This went on for about ten minutes and I thought I might as well see if he will go any further. I fumbled with his zipper and tried to unzip his pants thinking that if I could get a better feel he might harden up, but in my condition was not able to get his zipper down, which I guess speaks to the condition we were in. There was no reaction from him, he didn't protest and he didn't offer to help and I was reluctant to get on my knees between his legs so I could see for fear of scaring him off. With my hand still in his crotch I asked if he would now accept the fact that we are all bisexual. All he said was that in the condition he was in nothing was going to happen "down there". There was some feeble protest to the effect that I was molesting him and I said bullshit Bob, you sat there and spread your legs and let me do it without a word and I pointed out that he seemed to enjoy letting me feel him up. I figured at this point, after ten minutes he had enjoyed it and didn't want to admit it.
In spite of his protest he still sat with his legs spread and I kept my hand massaging his stuff when I kind of back away and asked if he remembered the first time he got off. He said no and I explained that the first time I had gotten off was on a camping trip when I was thirteen. The guy I shared a tent with and I got in to a grab ass thing in our sleeping bags. It wasn't long and it turned into a your turn, my turn deal with us each fondling each other. It became obvious that he had removed all of his clothes because when I felt him I could feel his hard cock through the sleeping bag. He wanted me to remove my clothes so he could feel me but I was too shy and kept my pants on. I later realized that if I had we most likely would have progressed to skin on skin contact. My regrets! It didn't matter because at some point he squeezed my crotch and I exploded with my first orgasm filling my shorts with cum. I immediately knew that it was the white stuff that had been leaking out at night.
After this exchange I said that I always regretted that I didn't pursue this kind of thing and felt that as a kid I didn't get to experience the typical teen age sexual experimentation. At this point I said that I have always wanted to know what it would be like to suck another guy off and have him cum in my mouth. I can't believe I did it but I then offered to give him a blow job if in return he would fuck me up the ass, which is something else I want to try. His interesting response was that there was no way he was going to fuck me up the ass. But before he said that he also commented about a little bondage and light pain, to which I was agreeable but he said nothing about the blow job. Somehow I think this is going to move forward, but I make no move until he gives me a signal he is interested. Maybe he wants to exchange blow jobs, I just don't know. I finally stopped massaging his crotch and there was some awkward silence and we decided to stumble off to bed. Him forward and me aft followed by my usual comment that what happens on the boat stays on the boat. In spite of the fact that we went to bed around two, I was awake early and re- living the previous night's conversation and thinking wow what now and trying to remember exactly what his crotch felt like! I finally got up and fixed some coffee and sat on the back deck drinking a cup. I was concerned that he was going to be angry and make a scene. I was surprised when he came to the deck and had a cup of coffee and sat down without comment. After some generic talk about how much we had to drink, I finally asked if he remembered that we had an interesting conversation last night and he responded with yeah, I remember some of the highlights which he didn't comment on. When he got up to leave we shook hands and I got the strongest hand shake I've had in a long time from anyone. Who knows where this is going, I don't think a guy would let you fondle his cock without some thought to going further. Who knows, maybe next time I'll drink less and let him sit on the floor next to the chair just to see what happens. I think I'll wear baggy sweat pants and no under ware which might help get to the next level. The thought of him doing to me what I had done to him is very exciting.
I waited two months before inviting him for dinner again giving him time to think about what happened. We agreed on a Friday night and I pickup up the usual booze and food supplies.
Not knowing what to expect, I thought that if he was up for something I wanted to be prepared. Late in the afternoon I showered, shaved, even some of the hidden spots. I took four enemas to clean out. Put a little Vaseline in my ass to cool it down after the cleaning. I had earlier picked up some ankle cuffs and new rope, just in case. Just before he arrived I popped a 20 (I usually only take ) mg Cialis tablet.
Being that he expressed an interest in bondage, I had lay out handcuffs and some new rope on the bed along with some other treats just to set the mood. In order to secure the ropes I had discretely installed some small but sturdy cup hooks on the under side of the bed and secured one end of the rope. I did the same at the head of the bed to secure his hands. I had also torn a towel into strips to use as a blind fold. Condoms and lube were placed on the counter along with rubber gloves all of which was covered. Clean sheets and two large bath towels covered the bed and a two foot long thin strip of polished oak lay on the bed. I looked over the set up and though, boy I am I ready.
When he arrived I asked if he would like a beer which he accepted. As I handed him the beer he smiled and said are you going to grope my crotch again. I just smiled and said, only if you want me to. He stood looking down into the galley at me and said I think I might like that. My eyes were at about crotch level and I stepped in front of him and run my hand up the inside of his leg and gave his crotch a gentle squeeze making him close his eyes and moan softly. I waited until I new he was enjoying it and I could feel his cock harden. I unzipped his pants and slipped my hand into the opening to feel his hard cock. After playing with him I removed my hand and zipped his pants and said that first I had to wash some veggies.
I was cleaning some veggies when he walked up behind me and put a hand on each hip. He pulled me back against him and leaned forward and whispered in my ear that I owed him some groping. I was taken by surprise because his lips were right next to my ear when he said it sending a bolt of electricity to my cock. I finally was composed enough to respond and said that I guess I did. You could feel him relax a bit and his hands moved slowly to the front of my track pants. Now keep in mind that I had hoped this would happen so I was clean, shaved balls and without under ware and primed with a stiff dick pill. Considering that playing with his crotch had me about half hard and within seconds my cock was hard and tenting out the front of my track pants.
His hands moved forward until he brushed against my cock and he said OH MY, what do we have here. His fingers wrapped around and he gently stroked my cock while his left hand moved down to squeeze my balls. My legs instinctively moved apart to give him better access. I could now feel his erection pressing against my butt and knew that he was as into this as I was. I slipped my hand back and started rubbing his cock.
Now we were both sucking air and making gasping sounds reflective of what we were doing. I'm thinking, how much better could it get, when I felt his hands move up under my shirt and his fingers slip into the top of my track pants. His hand moved down my stomach brushing my trimmed pubic hair and on to my now leaking cock. The left hand caressed my smooth balls and I realized how hot his hands felt. The sounds of moaning were now obvious. He continued to slowly stroke my cock and massage my balls. At one point he rubbed his finger over the end of my cock and said that I was getting awful wet.
I quickly turned around and he removed his hands from my pants and placed his wet finger to my mouth and told me to suck it. I slowly sucked his finger into my mouth tasting the slippery residue. He pulled his finger out and our lips brushed together for a second and his mouth opened and my tongue slipped in. After about the hottest kiss I can remember savoring the taste of my sex, I back away and asked if this meant that he had decided to accept my offer. With each holding the other guys crotch, he smiled and said what do we do now?
I asked if he was sure about this and he said no but let's go for it anyway. I asked if he knew what I was going to do. I explained that he has said a lot of things over time and I think I know what will make his fantasy become real and was planning to include some bondage and light pain. He just smiled and said Oh Wow.
I explained that I wanted him to take a shower and put on some under ware, shirt and socks that I have lay out. After he finishes I tell him to lie on the bed face up and that I would be back. He again asked what I was going to do. I explained that I was going to give him the best blow job he ever had but first I was going to tease him until he begged for it. As he entered the shower I dropped my warm up pants and put on clean white under ware which was the same as those I had laid out for him. When he was done showering he called for me and I went to the stateroom and uncovered my little surprise. You could hear an audible gasp as he looked at the things I had prepared.
I placed the handcuff on one wrist and then the other making sure to double lock them so they would not tighten up on his wrists. I explained that attached to the cuffs were a key. I told him to turn around and I took the towel and covered his eyes and tied it off. He was sucking deep breaths of air and I asked if he was OK and he said just nervous. Anticipation is part of the excitement. I told him to lie back on the bed and secured the leather thong tied to the center of the cuffs to the head board. I told him to put his legs together, which he did. I slowly traced a line from the inside of his knee to his crotch and lightly squeezed his package. He was instantly hard. I then placed a loop around each ankle and secured both to the foot of the bed. He is now secured hand and foot in a straight line on the bed face up with his eyes covered. I sat next to him on the bed and touched his right nipple through the tee shirt gently flicking the tip making him breathe a little faster and causing the front of his shorts to swell even more and his nipple to harden. I explained that I was going to be teasing him and causing him a little bit of pain to get him ready for the next phase.
At this point I got up and took off my pants. This left me dressed the same as he was down to the white socks. I got back on the bed and straddled him with my crotch over his so we rubbed together. I told him not to speak. I leaned forward and put my mouth next to his ear and in a whisper I explained that all he had to say was "Olympia". But if he said that nothing else was going to happen and we would be finished. He could beg, cry, say no please don't or anything else but I would ignore all words but Olympia. I told him that I would be doing some things he might like and maybe some he would maybe not like but that he had to decide if he would continue. I sat back up and deliberately ground my crotch against his. I really didn't care if he liked it, I sure did.
After pinching his nipples several times making him groan, I took a pair of scissors and slowly cut up the center of the shirt to the neck. I then cut through the arms and folded the material back exposing his upper body. I slowly run my hands up his stomach to his now erect nipples which I gently pinch and massage making him whimper. I played with his now very erect nipples until I could feel his cock harden under me. When I though he was as hard as he could get I grasp both nipples at the same time and pinched and twisted very hard making him cry out in pain. I explained that by making them hurt they would be more sensitive to light touch. I then leaned forward and sucked his right and then his left nipples. While I was doing this I was grinding my crotch into his. His breathing increased and he started moaning.
When he calmed down, I got off his body and slowly ran my fingers from his ankle to his crotch making sure to follow the outline of his hard cock through his shorts. His breathing increased and he started to moan until I grasp his crotch a lightly squeezed his package. At this point he is breathing like a man that can't get enough air. After caressing his package for a few minutes, I explained that he was going to experience pain and pleasure until his cock was dripping and ready to be sucked.
I got off the bed and released his feet and rolled him over onto his front. I made him get up on his knees with his head on the pillow. I couldn't help but thinking he looked like a frog in this position. I then pulled his legs apart and secured the lines to a hook on each side of the bed. Now he is face down legs spread ass up still wearing the tight white shorts that I provided. After looking at my handy work, I slowly ran my fingers; nail first, up the back inside of his right leg moving to the inside of the leg as I came closer to his butt. I slipped my hand between his legs and massaged his drawn up balls and stiff cock through his shorts making him moan. I then traced the outline of the shorts until I was at mid back where I allowed my hand to stray under his shorts and caress his bare butt which to my delight was shaved smooth. I allowed my fingers to just lightly brush his puckered hole making him shudder. I removed my hand and again started over with his left leg making the same movements and again slipping my hand inside his shorts to rub his smooth ass.
I removed my hand and told him that this is just not going to work since if I was going to apply a spanking to his ass it had to be bare ass. I picked up my scissors inserting the rounded tip under the leg of his shorts and slowly cut my way to the waist band. I repeated the process on the other leg, essentially cutting away the only covering he had. I gently pulled the back away exposing his ass and hole. As I pulled them off I could see a wet spot from his leaking cock and smell the unmistakable smell of man sex. I took the opportunity to massage his tightening balls.
I again repeated the motions with my hands on both legs, this time not obstructed by the shorts. With a light finger nail scraping of his puckered hole, his breathing started to resemble a man running a race.
I picked up the narrow strip of wood I had provided and run it over his ass and down his crack making him whimper. I explained that since he was about to be a very bad boy he would have to be punished. I took aim and struck his ass with a light but meaningful stoke. He jumped but made no sound. I explained that he would get 10, 15, or 20 at his choice. He opted for 20 and I explained that they would be given four at a time with some pleasure in between but that once we started the number was set.
I continued with four strokes of the wood and again caressed his ass and balls, each time forcing my finger further into his hole. After ten strokes I followed the same routine and he actually relaxed his ass allowing my finger to penetrate up to the first knuckle making him grunt in approval. The last stroke was delivered to get his attention. My swing was strong and hard causing him to struggle and scream in pain. I explained that this part was over and that looking at the stripe I just left on his ass I felt he needed some lotion to cool his ass off. As I prepared to rub a cooling lotion over his ass he just whimpered. After coating his ass with a moisturizing cream and avoiding his hole, I stopped and said that it appeared that I had missed a spot. When I got to that point and I put on a rubber glove so he could hear the unmistakable sound. I coated my middle finger with a heavy lube and lightly touched his exposed hole. With increasing pressure and movement I soon had the outside his hole lubed and my finger pressed against the pucker. He soon realized I was not trying to penetrate his ass and started to squirm around. I told him if he wanted my finger in his ass he would have to relax and push back against it. I felt a little pressure and he pushed back. I held my position and his ass slowly opened around my finger. After a few minutes he was backing against my firm finger and fucking himself on it. I almost thought he was going to say "Olympia" but instead he was begging me to fuck him.
I rolled him over and placed him on his back. As I turned him over I saw that his cock was leaking profusely. In this position I left his ankles free but spread and raised his knees. I did this to make sure I had access to his ass when he came, because I wanted to milk every drop from his prostate as he came.
I again pinched both nipples and sucked them until they were hard and stood out. I said I that I think it is time to make you happy and slid down his body with my lips until I got to his erect cock. I took my finger and wiped the tip gathering a very thick sample and held it to his lips telling him to suck my finger. His mouth opened and he sucked like a starving baby. I removed my finger and said you seem to like that, I think this time I'll use my tongue and let you suck on it. I moved down and licked the head of his cock clean and moved back up and pushed my tongue against his lips, his mouth opened and we tongue danced for a minute.
It was time, I moved down his body and with out any teasing opened my mouth and took his cock clear to the back of my throat swallowing as I did. His body started bucking against the restraints and he was grunting. I figured he was on a short fuse at this point and moved my finger to his hole just in time to feel the first spurts hit the inside of my mouth and his ass pucker with each shot. I quickly inserted my finger to feel his prostate pulse with each shot. As he slowed I pushed against his prostate making him contract several more times and produce less fluid each time until I could feel his cock twitch but nothing came out. I slowly pulled out my finger which generated one final shudder of his body.
With his breathing back to normal I released him and as he got off the bed he fell back toward me and I caught him asking if he was OK. All he said was that I had actually delivered what I promised and he staggered toward the bathroom. I just smiled and thought to myself, not bad for my first blow job. I just wish I could remember the taste better, but I was busy swallowing to make room for more.