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Breaking a Young Man


Author: Swat412

M/m spanking/wooden hairbrush/paddling and sex (sodomy) R/L and discipline of a naughty young man.

When this took place there was no real ‘age of consent’ in the Virgin Islands. The punishment given to this young man was necessary and not overly rough. The sex was consensual always and he enjoyed it as did I, had it been rape he could have said ‘stop’ anytime, he didn’t but eagerly participated every time as we got into bed together. The punishment was given under protest but he understood in time that it was a necessary thing to administer and it made him into a better person. Although he did always try to get out of it in some way in the end he would submit after his bottom began to burn.

We pulled into the little bay and as I had suspected it was empty, perfect for what I had in mind. Dennis went forward and dropped the anchor for me then played out the rode as the boat swung around and the hook caught the bottom. After making sure that it was secure (well dug in) I told him to tie it off. He did leaving enough slack in the line that we would ride easily without pulling it up then began walking back to the cockpit. I stowed some loose things under the cockpit seats and made up the lines as he helped then sat down in the one seat saying ‘Come over here for a minute young man.’ I patted the cushion to my right with my hand and he walked around to sit there while looking at me.

There had been a couple of warnings in the past days about this great young lover of mine using dope and they had not seemed to have any effect on him. He either made a joke of it or ignored me. I had, unknown to him, made my decision and that was the reason for this trip, he had no idea what he was about to get and I was determined to give it to him no matter how much he protested and struggled. What he didn’t know was how lucky he was right now! I had been looking for a heavy belt or a paddle before we left St. Croix, if I’d been lucky his cute little backside would have been blistered a lot more than I could with my hand. I was going to make it a point to either find or make a paddle to use in the future; my cute little lover would learn to obey after a few sessions with it.

‘We’re going to stay here for a few days Dennis’ I began ‘while we are here there are a few things that I want to handle…you in particular are one of the things.’ This statement got a questioning look from him as I continued. ‘I know you think you’re grown up and can do whatever you want to and I’m not bothered by you drinking a little, as a matter of fact you’re kind of cute when you’re drunk. I am bothered by you using drugs and I don’t care how harmless you think pot is, the drugs are going to stop…now.’ I had slipped my arm around his shoulders as I talked, my statement got the beginnings of a mild protest from him but I stopped it by telling him to be quiet and listen to me.

‘I’m dead serious about this young man and I intend to take the necessary steps to correct this problem beginning right now.’ With my left hand I hooked his chin and turned his head so that our eyes met, staring into those big beautiful dark eyes had my cock turning to stone in my swim trunks. Pulling him close until our lips met I gave him a long wet kiss, my hands caressed his body a little, that beautiful tight young body that I enjoyed so much! As the lingering kiss broke I said ‘I’m going to do something to drive my point home and get your attention then during the next few days I’m going to give you a few reminders so that I know that you understand me.’ Pulling him close again I kissed him very hard as our lips parted and our tongues entwined. Lying I continued after the kiss ‘This is something that I don’t enjoy young man but…I know it’s one sure way to get your attention…and get my point across that I mean business.’

He had no idea what was about to happen and for a few seconds we stared into each other’s eyes until I made the move. Leaning away from him slightly I took his left arm firmly in my grip then leaned back as I lifted his slight frame and pulled him to my left. Dennis rose a little as I pulled leaned across me a little then I pulled his left arm forward as I switched hands, my left taking the back of his neck to push him further, my right cupping a hard young cheek and pushing him across my lap. In seconds he was over my knee, there was a little wiggle as I moved him some more and tucked his body in close to encircle that slim waist with my left arm. As I positioned him the old worn swim trunks slipped down a little to expose some of his tanned bottom, although his left arm was trapped he tried to put his right one back, I grabbed the wrist and pulled it to his side. There was a mild struggle as I began to pull the trunks down to bare his bottom, Dennis wiggled around on my lap and kicked a few times but I increased my hold on him and sharply told him to ‘be still’.

‘Wha…what are you…going…to do?’ he wailed as he wiggled tossed his head around and tried to break my hold on his wrist.

Continuing to pull the trunks down to his knees I said ‘Something that should get your attention young man…a good old fashioned spanking!’ Cupping a firm bare cheek and subduing his struggles I said ‘I’m going to blister your bottom good then we’re going to take care of this habit of yours. You’ve probably never been disciplined before so I intend to make this one a good one…when I’m finished you won’t be sitting for a while!’ Dennis wiggled harder and began to thrash around on my lap, his slim young lags kicked as he realized what I was going to do! Although he had never been spanked before he knew what I meant and became almost frantic in his attempt to free himself. The swim trunks were kicked off seconds later and his beautiful tanned naked body was exposed over my knee.

I hung onto his struggling body and raised my arm high over my head as he squealed ‘NOOOOOooooo!’ in his high-pitched girlish voice. He then cried out in real pain as my hand cracked his firm right cheek, his coltish legs shot straight out behind his body as my arm rose again and my palm found his left cheek with a loud crack! His firm bottom flattened and rebounded a little as my hand found it’s nice solid target over and over, Dennis arched his back hard clinched his cheeks and kicked like hell as I spanked very hard. As the pain increased so did the amount of noise he produced, the sound of the spanking and his yelps of pain echoed off of the shore and trees of the small bay shortly after each hard smack! After a few minutes of spanking his struggles began to lessen as the pain built in his tight bottom then spread up his back and down his thighs. His wails of pain turned to blubbering and outright bawling as his tanned ass turned pink then red then a deeper red color as his tears poured out.

Shaking all over his shoulders trembling hard my sweet Dennis openly bawled between the good hard smacks to his bottom. I slowed the rate of the spanking then allowing him time to draw a hard ragged breath and let it out in a wet sob before giving him another good smack. By the time we reached this point his tight little ass was a nice deep red all over and beginning to show some bruises, the outline of my spread fingers was evident in a lot of areas. He was also wiggling and bouncing on my rock hard cock. As the spanking came to an end I concentrated on his upper thighs and the lower part of those hot cute cheeks, these smacks were followed by very loud squeals of pain. He was well past struggling, it had been spanked out of him, he wasn’t past arching his back very hard after each one and flexing his legs after they shot straight out behind him.

There were several kids like Dennis that were called ‘Warf Rats’; they were runaways or homeless kids that had wound up on St. Croix and the other islands. To survive they did menial work for the charter boats and some even served as crew or cabin boys/girls on some of them. Dennis had been around for a few years and was pretty well known for doing ‘anything’ for some money and food or a job. I knew that he had worked on a few of the other boats, these jobs quickly came to an end when he was too beaten up or drugged up to work so he was fired. The ages of these ‘rats’ was from twelve to eighteen/twenty years old, Dennis was fifteen and I had been told by another skipper that when he was straight and sober he was not only a good worker but a very good lay.
He would not only willingly service the crewmembers but would do what was expected to service members of a charter party that wanted any kind of sex with him for money.

One story that I’d heard was while out with a party of men that totaled six (on one of the bigger boats) Dennis had spent a few evenings taking care of every ones needs. He spent quite a few hours filled from both ends and put a smile on every ones faces plus filling his pockets with cash. That’s why when he showed up at my slip wearing not much but a pair of ragged cut-offs and a nice smile I decided to try him out for a few positions. The kid was just flat out cute from end to end, had a very nice tan long hair that was bleached out from the sun and salt, a nice young body and (from what I’d seen in the past) a cute little ass that begged to be touched and …

He told me that he needed a job and money badly, he also told me why he had been thrown off of the other boat. I gave him a twenty and told him to get his stuff and get back soon, we were leaving for St. Thomas for a few days to have the auxiliary engine overhauled. He took off and I finished getting the boat ready to shove off for the short trip. When Dennis returned, in about an hour, I was ready. He put his small amount of possessions and clothes below then helped me shove off, in half an hour we had passed the harbor jetty had the small jib up and he was finishing raising the main. After setting the course for St. Thomas and setting the sails we relaxed for a while, I had the wheel while Dennis got us a couple of cold drinks then we settled in the cockpit and talked. His first question was where he would be sleeping; I hadn’t been able to keep my eyes off of his body as he had roamed around the boat so my answer was quick and to the point. ‘With me in the forward cabin.’ Dennis gave me a little smiling look and said ‘Sounds Ok…I guess that means you’ve heard about what I’m like?’ I told him that I had and was interested in finding out all about him. We talked for a little while longer, mostly about what his duties would be then he excused himself to go below. When he reappeared the small swimsuit he had changed into didn’t leave much to the imagination, it had to be the briefest pair of swim (if you could call that bandana ‘trunks’) trunks that I’d ever seen on a male body! I had him sit beside me as we sailed along in the afternoon light, we talked a little more I held him a little and openly began to fondle his tight young body. Shortly Dennis was on his knees between my legs sucking my cock as I kept the boat on course. His little trunks were off so that I could do some playing too, he had a nice six-inch shaft and was almost devoid of pubic hair. It was a shame that we had to get back into our trunks as we approached the harbor entrance at Charlotte Amalie by then I had found out that my young friend could indeed do a good job of sucking a cock. Even though mine was a very big mouthful for him he had done a good job and enjoyed it.

After finding our slip and tying up (we were the only charter boat there) Dennis helped me get the power and water hooked-up. It was a beautiful warm evening that was going to get pretty hot, as I called the guys that were going to do the overhaul I told Dennis to go to the boathouse and take a nice long shower. I was finishing up on the call when he walked away carrying a towel, his nice tight young ass had a nice wiggle to it, almost like a girl. When he returned I had fixed a small meal and eaten some, I told him to eat what he wanted I was going to get my shower. Upon returning we both worked at getting the canopy up over the cockpit for some shade the next day, we were going to be doing a little work on the boat and the guys would enjoy the shade while working on the engine. As we did this I opened a couple of beers for us explaining to Dennis that as long as we weren’t working with a party we could have a little one of our own, I also wanted to loosen him up a little for later.

We enjoyed a few beers and did a little clean up of the dinner mess, I let my hands do some roaming whenever we were close enough and Dennis didn’t shy away from my advances. The touching led to hugging then I tried a few short kisses on his shoulders and neck then his smooth cheeks, I was feeling him up all over his nice tight ass cheeks and rubbing his cock through the trunks, we were both getting hard. I pinned him against the counter so that our bodies ground together grabbed his hair and looked into those big dark eyes as our lips met. Dennis closed his eyes as we kissed and opened his mouth wide to accept my tongue; the kiss left us both breathless and lasted for a while!

My cock was rock hard now, I held Dennis close and whispered softly in his ear ‘Let’s go to bed…I’m going to do my best to fuck your brains out young man.’ As I told him that I pushed the trunks down and he stepped out of them to turn and head for my cabin, I grabbed the can of Crisco and an old towel to put down on the bed then followed his cute ass. He stopped between the bunks and turned as I walked in, I took him into my arms and gave him another good hard kiss while pushing myself against his hard young cock. The bunk in the forward cabin is divided in a ‘V’ shape with an area about two feet wide where they meet, the floor sloped up so I was actually a little higher than the persons ass when they were laying on the bunk. I coached Dennis up and got his great young legs spread wide so one was on each side of the bunks, overcome with lust at this beautiful picture before me I dove on his ass to begin to lick and kiss it all over. In seconds Dennis was moaning and wiggling under my attention, I worked on that tight little crack, his balls and that tight little asshole with my lips and tongue. At the same time I gently stroked his hard cock it’s full length.

Dipping a little Crisco I found his tight hole and lubed him a little, he was nice and tight as I used one finger then two to probe him. As I did this his tight little ring of muscle squeezed and released my fingers with a regular rhythm that felt good, I reached around and began to gently fondle his semi-hard six-inch cock as I pumped his asshole. In a few minutes he was good and hard I was still pumping him and my cock was like a rock. I played a little more then put my weight on him to lay against that tight young body to cover his shoulders and neck with kisses, we were both breathing pretty hard. I used a little more Crisco on my thick cock then grabbed the shaft and slipped the head of my hard eight inches between his tight little cheeks to position it against his waiting rectum. Dennis wiggled a little spreading his legs and pushing back against me as I began to thrust my cock-head in, as I spread and penetrated him a few inches he gave a gasp then moaned louder as I fed his ass my full eight inch cock until I was solidly against those firm ass cheeks. His cheeks clinched and relaxed against me as he worked his rectum, I grabbed his thighs to lift him a little higher on the bunk then thrust myself in good and deep while grabbing his shoulders. Dennis moaned then gasped ‘OHHHhhGod…you’re big…really big…man you’re filling me!’ I was filling him but that would change in time, right now I was hitting bottom inside of him as I ground our bodies together. I pulled back until just the head remained inside of his tight asshole then gave a long slow thrust until I was deep inside of him again, this boy felt great and I hadn’t been in anything this tight in a while!

Although I fucked away with long slow strokes and had been on the edge of cumming a few times I couldn’t for some reason, after a while I pulled out and helped him get on the bunk on his back. Dennis rolled over then immediately pulled his legs up and spread them wide while pulling his balls out of the way, his great little cock was hard and pointing back at a sharp angle. I put my hands on the back of his knees to roll him further then stabbed at his rectum with my cock head, there was no problem finding the target. Dennis gasped and squealed as I slammed my cock deep inside of him, once buried solidly in his tight ass I let go of his legs to put my weight on his young body and wrapped my arms around him. Now the long hard strokes began as I slammed against his firm cheeks, Dennis arched his back and moaned pretty loud at times as I drove my cock in as deep as possible. Some of his moans were turning to squeals of pain as I hit bottom deep inside others were being brought on by having his young rectum stretched so far by my cock and my hard reaming. With this combination of the cute boy wiggling and gasping under me the hot tight hole I was forcing my cock into over and over again and his little rectum clinching and relaxing around my solid cock it didn’t take much longer for me to unload inside of him. It seemed to begin in my toes and move slowly up through my aching balls as the release slowly built and built, a couple of long hard strokes later Dennis cried out loudly as I buried my cock to the hilt and ground myself against him harder than ever. It seemed that I would never stop pumping my cum into his bowels! As we began to relax and catch our breath I slipped out of him and moved around to take his hard cock in my hand then cover it with my mouth, a few minutes later I gave my young lover his release as he filled my mouth with his sweet young cum.

I awoke hours later, it was still dark and we were in the spoon position. The taste of his cum was still lingering in my mouth as we lay there; I had Dennis in my arms and could feel his deep even breathing as he slept. My cock was rock hard again and jammed between his slender thighs, I must have been erect for a while because it was aching like hell! As I moved a little Dennis moaned, I got my fingers down between us to probe his crack and finger his tight hole, there was still a mess of Crisco there. I slipped my cock into position moved the head up and down his tight little crack then pushed as my hand went around him to apply pressure to his belly. As the head forced it way into his rectum Dennis gave a sleepy moan and pulled his legs up, I kissed his shoulders and neck then got a louder moan as I filled him once more. A few slow strokes had my cock deep inside and slick with the Crisco from before, I rolled us over straddled his slim young body grabbed his shoulders and began a nice slow fuck as our bodies rocked together. This time Dennis hissed and moaned as he made a mess on the sheet under him, as he pumped his load his little ring of muscle bore down on my cock and I filled him once again. This scene was repeated shortly after daylight as I pounded his ass again with a vengeance.

‘God am I sore’ Dennis said as we sat in the cabin eating breakfast ‘I think you were all the way in my stomach last night!’ I told him that I had tried my best and he laughed at that comment. I had him come around the table and sit down on my lap facing me, he was wearing those skimpy trunks that hugged his ass and outlined his cock very well. We kissed while I felt his cheeks through the material then moved my hand around to rub his cock a little. There was a twitch and he began to get an erection, I told him to get a shirt on and do the dishes ‘As much as I want to fuck you again the guys will be here soon.’ Dennis did as I told him and was almost finished cleaning up when we got company.

The problem was that I did not condone the use of dope and Dennis had picked up the habit. The first day at St. Thomas he casually had a few joints and after a couple of hours was pretty smacked, I mentioned that I didn’t want that sort of thing on the boat. He laughed it off and I added that if we were going to be living together and working together the habit would stop. That time I told him in a nice way and asked him to get rid of what he had then not bring any more on board, I could be stern if needed as he had worked his way through most of the charter fleet.

The next time I was a little more stern and gave a warning, the next time I caught him I explained that there would be no more warnings ‘Stop this right now young man or you will be disciplined for this habit.’ He was a little shocked, I was angry but we still got along and worked together. We had a couple of days before picking up our next charter, that’s when I planned to go to a private area and ‘handle’ the problem once and for all. Not having a lot of time before we left I thought a good hard spanking would do the job and a sore bottom would help get my point across. I was wrong.

I slowed the rate of the spanking but kept every one of them good and hard as I worked over his lower cheeks and upper thighs. Dennis jerked and squealed, wiggled and kicked franticly as he bawled and howled away over my knee, he also had an erection. The lecture and spanking continued until I was not only satisfied that I had made my point but my hand was too sore to continue. His entire backside and tender upper thighs were a deep red, the areas getting the most attention were welted and beginning to show bruises. I stopped released his wrist and listened to him squeal as I rubbed his tender bottom gently and finished the lecture. When told to stand up Dennis rose with my help to stand on shaking legs, I allowed him to ‘dance’ for a few minutes and rub his sore bottom, his beautiful young cock stood out in front of him bobbing around as he danced and bawled before me. I stood to take it in my hand and put my other arm around him to hold him tight for a short time then said ‘I want you to go and get all of the ‘stuff’ and bring it to me.’ He sniffed and blubbered as he shook his head in a ‘yes’ then turned to enter the cabin, he was having a lot of trouble walking but returned quickly with everything and handed it to me to dispose of. I sent him to bed then listened to an hour of sobbing and sniffing as he calmed down. The spanking had been a shock to him and that’s just what he needed to break the habit.

Checking on him later found him on his stomach with a very sore red bottom on display, the spanking had been hard enough to leave both cheeks bruised. My inspection showed a double line of little purple welts running down the inside of both cheeks, there was some wiggling and squealing as I inspected and rubbed his tender bottom. Dennis did some gasping as I undressed and got into the bunk with him rolled him on his side so that we faced each other and put my arms around him. I held him kissed him and talked to him as I continued the lecture while running my hands over his body, he was still crying a little and sniffing, his cock was now limp. As I explained that in the next few days there would be ‘reminders’ he buried his head in my neck to cry some more, he gasped and moaned as I cupped a sore cheek with my hand and squeezed it firmly. ‘I want your obedience young man and I intend to get it…not being able to sit with any comfort for a while will help to insure that.’ I also told him that as soon as I could find a proper paddle or strap I would make sure that he knew what that felt like.

That evening and the next morning went well, we did a little work on the boat and relaxed. Dennis behaved himself and took care to sit on something soft when he did sit. The next morning, after a late breakfast, we got everything cleaned up and put away. Although Dennis was still a little sore and tender back there it was time to take him in hand once again.

Pulling him to me I said ‘It’s reminder time young man…right now.’ Dennis pouted at me then looked at the floor as I unsnapped his cut-offs and pulled the zipper down, with a little tug on the waistband they slipped down his legs and into a pile around his ankles. He stepped out of them as I took his arm and led his trembling body forward to our cabin for the spanking. He held back resisting a little but had been told that if there was too much trouble from him the punishment would only take longer. Reaching the cabin I turned him to face the bunk and placed my hand between his shoulders easing him down across it, as he assumed the position with a heavy sigh I took the bottom of his t-shirt and pulled it well above his trim waist. His cute tight ass cheeks were still showing a few bruises from the first spanking, there were also a few little spots on his upper thighs that had light bruises remaining. He obeyed me when I told him to spread his legs as far as possible and stretch his arms out in front of himself ‘Keep your hands away from your bottom and don’t try to cover up…if you disobey me the spanking will be longer.’ That order got a whispered ‘I will’ from him then he drew a couple of long ragged breaths.

He moaned as I moved to his left side put my hand on his trim waist and tucked him in close and hard against me. Sensing my movement as the swing began Dennis clinched his tight little cheeks very hard; they were still tightly clinched as my hand smacked his left cheek with a loud crack. His entire body jerked from the first spank and his slim legs began to shake as his breath came out in a loud gasp. I aimed at the other cheek and gave it a good smack of equal force; this time there was a little yelp of pain following the smack. I moved my aim down to his lower cheeks and repeated the hard smacks to his tightly clinched ass, a few more had him wiggling around and gasping as the stinging pain built again. At about number six his shoulders trembled harder than ever as his head shot up, Dennis gave a loud wet wail then slumped back on the bunk as his tears began to flow. After two more I stopped to rub his bottom gently, it was on fire again and he was shaking from head to toe beginning to increase his bawling.

As I rubbed he wailed ‘OHHHoooPleeaseeee…NOMOREPleeaseeeeee…pleeeeassss…it hurts so muchPLEEASEEEEEEEE?’

‘I told you that you were getting a few reminders and this is one of them young man.’ I said ‘I also told you that you probably wouldn’t want to sit for a while…and I don’t think you do at this point!’ He was flexing his coltish legs and wiggling around while clinching and relaxing his burning cheeks, I rubbed a little more. I then finished the spanking by giving him about six of the hardest ones I could, after each I gave him a few moments to collect himself and almost catch his breath then my hand would smack the tender target once again. Each one got a loud yell of pain as I made my point. I then allowed him to lay there and bawl for a few minutes but I was rock hard!

He watched as I put the jar of Petroleum Jelly down on the bunk then moaned ‘No…please not now…oh God…it hurts so much…please not now…please?’ Reaching under his slim body I found and held his fully erect penis in my hand ‘This doesn’t look like a ‘no’ to me Dennis, your hard cock is saying ‘yes’.’ I stood directly behind him to take off my swim trunks and look over that cute but well-spanked little bottom then got some of the lube on my fingers and probed between his tight cheeks. As I found and began to finger-fuck his tight little ring of muscle Dennis continued to sob into the sheet, I put some of it on my rock hard cock then placed the head between his hot cheeks to run it up and down his crack. There was a wet gasp from him as the head penetrated his tight rectum then a little squeal as I eased a couple of inches in slowly. I gave him a little time to flex his rectum around my cock and try to relax then grabbed his waist and filled him with my cock. Dennis continued to give little gasps and wiggle his bottom as he took all of my cock; he was hotter than ever and seemed very tight as he lay there. I began to fuck him using slow long strokes pulling back until just my head was inside of him then easing back in until every inch was buried in him and I was resting against his hot cheeks. In this position we came at about the same time, I left my load deep in his bowel and Dennis blew his on the side of the bunk and down over the woodwork. While still hard I removed my cock from his tight rectum with a little wet ‘pop’ then helped him get onto the bunk to hold him for a while.

A few hours later we were back at doing some things on the boat, Dennis wore only a t-shirt and was glad that we were alone in the little cove. There was another period of sitting very little after the ‘reminder’.

While in St. Thomas, waiting to pick up a charter party, Dennis and I went shopping. I found two nice things; in one store there was a display of thong bathing suits for men and boys. I liked the idea of putting those cute cheeks of his on display so I bought a couple of them. In another market I happened across a very nice long-handled hairbrush, Dennis watched me pick it up and cringed a little saying ‘I don’t think that’s for brushing hair is it?’ I slapped it against my palm a couple of times and looked at him, each smack got a little jump from the boy. As he rolled his eyes I said ‘This should get your attention young man.’ Dennis swallowed hard and sighed a little, I purchased the brush from a smiling saleslady (English) and she made a comment about ‘other’ uses for the brush. I told her that I had exactly that in mind as I had not been able to find a suitable paddle she then looked at Dennis and added ‘Regular use should keep the young man in line and on his toes.’

After a little more shopping we returned to the dock to find the charter party waiting, as the travel agent had stated it was three business men on for our seven day trip. We helped them all get settled and shoved off for the first leg which would be Virgin Gorda, it would take most of the day to get there and promised to be a pleasant sail in the beautiful weather and calm seas. Although Dennis still had a couple of little bruises on his bottom I told him to try on one of the new thongs, with a little hesitation he finally obeyed me and went below to change. Upon his return, in a skimpy t-shirt and the thong bikini, two of the men openly looked him over…really looked him over! We were all taking turns at the wheel in open sea and, after Dennis moved around a little, one made a comment that it looked like someone had been given a trip over the knee. I explained that he had and a little of the reason for it, the man agreed that discipline was a good thing as Dennis blushed all over.

Later, as evening fell, the man approached me in the cockpit as we had a few drinks and began a conversation about Dennis. He talked around the subject for a little while then finally came out and asked if Dennis was available to take care of the party’s ‘needs’. I told him that he would probably agree to it but that Dennis should be the one to make the decision, I then called Dennis to join us and had him sit beside the man. A nice conversation followed as the man got very friendly with him and went on to explain that, if Dennis was interested, two of the men would love to spend some time with him. He also explained that Dennis would be well compensated for his time. Following this he took Dennis by the hand and led him to the forward deck for a little petting session that lasted about half an hour. When Dennis returned to the cockpit alone he was using his t-shirt to wipe his face, the guy had obviously blown quite a load!

Dennis sat down beside me and said ‘Bill wants to take me to bed and…I guess it’s Ok with you?’ I told him that he had asked me and I didn’t mind adding ‘it looks like you already gave him something to get excited about.’ ‘God’ Dennis exclaimed ‘I don’t think the guy has had a piece in a month! He’s horny as hell!’ We discussed how it would be handled and then Dennis said ‘There is one problem…I haven’t gone to the bathroom for a couple of days.’ I told him that we would handle that and had him take the wheel for a little while as I went to prepare a suppository for him. Once we were at anchor I would handle the ‘problem’ for him.

It didn’t take long, I had Dennis join me in the head/shower where the soap suppository had been soaking in warm water had him strip his thong off then bend and spread for me to insert the soap. Within minutes he was moaning as he sat on the head to empty himself completely, I left as he stripped and took a shower. After dinner and a few drinks everyone began to retire for the evening, Dennis and his friend spent most of the time on the forward deck having a few drinks and making out. I went to my cabin to allow everyone some privacy but there was no way to miss the sounds that came from one of the other cabins as Dennis provided his ‘service’ to the men. A nude young man joined me later to slip under the sheets and cuddle for a while, we had a whispered talk before going off to sleep. I was erect from listening to the sounds of sex; Dennis had handled both of them sucking one while the other had worn himself out on his tight backside. The one guy was pretty well hung and Dennis was sore ‘I thought he’d never get off…he just kept going and going in me.’ Dennis moaned.

There was a mild protest as I had him roll onto his back and get his legs spread for me. He was still well lubed and loosened from the sex and I had the same problem getting off. The next day Dennis was a little sore but had more money in his pocket.

Dennis looked at me and at the hairbrush in my hand, he was trying to get some words out as his mouth moved but nothing came, I repeated my command to him. ‘Get in the dingy young man…we’re going ashore for a while!’ As he finally began to voice a protest on of the guys spoke up and said ‘Why bother going ashore, we all know what’s going to happen, you may as well just handle it here.’ Dennis looked around as he blushed a deep red and gulped hard then gave a deep sigh. I said ‘It doesn’t bother me but it will be noisy as hell, this young man is going to get a good tanning.’ To this they all simply shrugged then the other guy that had been fucking my little cabin boy said ‘What the hell, we all know what a spanking is like, it doesn’t make any sense for you to take him ashore for it.’ As they all agreed I took a pouting Dennis by the arm and started him in the direction of the main cabin, he tried to bulk a little but when the one suggested that he take it like a man he began to take slow steps as I followed.

I selected on of the armless chairs and directed him to it then turned him around. While looking into those big dark eyes and watching his lower lip tremble I hooked the waistband of his thong and pulled it down just below his tight bottom. As I sat and put him across my lap the one man entered and leaned against the counter to watch. Dennis wiggled a little then tensed with his hands palm down on the carpet and his toes just touching it, his coltish legs bobbing and trembling behind him.

Resting the hairbrush on one shaking cheek I told him that I didn’t expect to have to do this after the last time, Dennis didn’t answer that he simply drew deep hard breaths in anticipation of what was to come. When I raised the brush he kicked hard in anticipation and yelled ‘NOOOOOOOOOOOOOOoooooo!’ A split second after the brush cracked across his bottom he yelled again…hard and long! At the same time his right hand came back to try and protect his young bottom as he twisted and wiggled on my lap, as I swung the brush at the other cheek Dennis yelled and kicked harder. That’s when I took a firm hold of his wrist and pulled it to his side then began whacking hard and fast! The wiggling and kicking continued until about number twelve, by then he had begun to bawl his bottom was a nice deep red and he was squealing at the top of his lungs. As I spanked the struggling out of him he simply stopped everything but the yelling and kicking.

This was the third spanking in the past two weeks, the first with the hairbrush. He had feared it but disobeyed me anyway and this time it was doubly embarrassing. Dennis was not only over my knee with his cute red bottom on display but he now had an audience as he bawled and kicked!

As the loud session went on the other two members joined to watch and mixed themselves fresh drinks, Dennis howled and kicked arching his back with almost every fresh whack as they watched his bottom turn a nice deep red. I was applying the brush with good hard swings and the cracking and popping in the small room coupled with his loud howling was almost too much to take. He blubbered away until my arm became tired then slumped there to gasp and bawl when I stopped, his young body heaving as he sucked deep hard breaths. I let him bawl for a while then helped him stand, his hands shot to his bottom to gingerly rub his cheeks as he flexed his legs and danced a little. That beautiful young cock of his was fully erect again and there were some comments made about that from the audience. It made a handy ‘handle’ for me to take in hand and lead him to our cabin where I put him to bed once more with a VERY sore bottom.

I re-joined the charter party and we shared a discussion about the merits of corporal punishment and the use of some different tools. I explained that I had been looking for a paddle and (not finding one) the hairbrush was the next best thing. The guy that had been enjoying Dennis the most offered to send a paddle back when he arrived home ‘I can make one in an evening and will do it with pride knowing that it will be put to good use.’ As Dennis sobbed away in our cabin I thanked him for his offer then explained that I wanted a ‘Sutton’ if he was going to make it. A few minutes later I had sketched an idea of what the paddle should be like, twenty inches long three inches wide with three rows of holes in it. We all agreed that it would be the perfect thing to keep this young man in line in the future.

A few weeks later the paddle arrived, just in time for a well-deserved whacking with it. Poor Dennis bent over the table in the galley with his underpants around his ankles to yell once more as his little bottom became red and sore. The paddle became a fixture in the galley after that. Over the next few years it was used on Dennis quite a few times, it also was used on a very nasty daughter on one charter as well as a bitchy wife on another. Whenever someone would ask about it I would simply answer that it was kept on the boat for attitude adjustment whenever needed.

Copyright Glowing Results 1999

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