This diary is intended to be a record of the training and indoctrination of my new Virgin Boi(s). Click here for the Rubber Diary
Sometimes a meet happens very quickly. Sage had found this site, read through these diaries and the FAQ's and emailed me. He had some spare time that afternoon and wanted to find out if bondage and being a sub as for him.
I picked him up and, as I had explained, put him to work immediately we got in. The heating was up and he was eager.
The front door closed, the curtains were drawn and he was collared and ordered to strip. He wasn't keen on either a hood or wrist straps (at first) so, after a quick examination of his slim body and semi hard cock I slid a hand down his back to find his asshole was far from as tight as he anticipated. I pushed a finger in a little way and his cock jumped. This is was going to be fun.
I took him upstairs where he was immediately ordered to his knees, his face level with the bulge in my trackies. His mouth automatically opened and he leaned forward. I grabbed his head and said I knew what he wanted. He nodded and I flopped my hardening cock out in his face. He swooped on it and sucked it deep into his waiting mouth. I pushed harder and the head struck the back of his throat. He tried not to gag and swallowed it back as far as he could. Very creditable for someone who had only once sucked cock.
Next I threw him on the bed and saw, for the first time, his hard cock, well above average size, slap against his stomach, already oozing pre-cum. I bent down and licked it up. Mmm
I swiftly moved round the bed and knelt over his face, my cock waving over his mouth. He arched his back and reached up with his mouth, desperate to further practice his oral skills. After a few minutes of major sucking action I reluctantly pulled my cock for his mouth so I could work it myself. I shifted forward a little and my balls landed on his mouth. He started to suck and lick them, to my delight.
After a while he said that he wanted to try wrist straps so I got them out, strapped him in and then tied him to the bed head. His cock was once again slapping up and down in his extreme excitement. Again I knelt over his face and plunged my cock into his mouth. The only difference this time was that I now started to play with his cock. He groaned audibly as I sucked his erect member into my mouth and, with my tongue, slid his foreskin back. Then it was simple thing to grab his legs and pull them back and up so his rosebud virgin hole was level with my face. He wasn't expecting what happened next. I leant down and my tongue found the very epicentre of his anal pleasure zone and he squirmed and wriggled as my cock pounded his face and my tongue probed his ass.
Next on the list of things to try was anal toys. I lubed him up and got out my big purple vibrating dildo. A quick look at his face and I could tell he wasn't sure whether to be scared or delighted. As it turned out it was another case of making him squirm with pleasure. His moans were once again being stifled by my cock in his mouth but I could tell he was enjoying it.
It had become very evident that Sage's forte and his favourite activity was cock sucking, especially a nice thick one (mine!) and he couldn't get enough. But this was also coupled with the fact that he absolutely adored any sort of anal play.
Eventually it was time for him to return to the outside world and his responsibilities. I ordered him to cum, which he did within minutes. He had been holding back for so long it was a welcome release for him. He will be back.There aren't any pictures to go with this piece as Sage wasn't comfortable with any being taken. A shame as he has a great body and cock
Stacy returned for his second visit with very clear ideas of what he wanted and, more importantly, an issue he needed to deal with. We had discovered on his first visit that he had a phobia of sucking cock, he gagged way too easily. It was a mental stumbling block. A major problem for a submissive slave boy. We had chatted over email about how to overcome this and I felt we had reached a breakthrough in his psychological acceptance of the need to suck cock.
Thus this visit I was very interested to see how it would work. He had a very clear idea of the ass work he wanted so that was his 'reward' for overcoming his extreme gag reflex. Naked, strapped up and hooded Stacy was ready to try and start his oral training. We were both please to find it worked, more or less. The only issue happened when he tasted my pre-cum for the first time. But I think that is going to be a one-off. He is very keen to swallow my load and demonstrate his innate submissiveness.
Working his ass more aggressively than on his previous visit I edged him nearer and nearer to cumming several times. With time running out (he had to get home at a reasonable time for work tomorrow) I finally allowed him to cum. Given less time pressure I would have kept him tied up and used his ass some more before making him cum again. Unfortunately he had to leave. There will be another time
I had emailed Sherard a few times over the last couple of weeks before we managed to both be available at the same time. I had arranged to go and pick him up from near his home. By the time we had got back to mine we had discussed what his limits were and what he was up for trying. Always a sensible thing to determine with straight boys.
We went straight up to the bedroom because, although he wanted to be tied up, I got the impression it wasn't so much that he was sub but more that it absolved him from trying to work out what to do.
He stripped off without being asked and presented himself to me in all his glory. As you can see from the pics he has a beautiful body which he works hard to keep in shape. I wanted to get a hood on him quickly so I could start taking pictures.
I sat him on the bed and introduced him immediately to a cock in his mouth. His initial trepidation quickly turned to enthusiasm as his eager mouth set to work on my hardening cock.
Laying him back and tieing him up I raised his legs to expose his tight, virgin hole. Like most straight lads he was quite dubious about how it would feel to have his ass abused. My first assault on his cherry was with my tongue which caused him to sharply inhale with pleasure. Once he had got used to that I started a finger stroking around the sphincter. He started to relax a bit so I got some lube to it and pushed a bit harder. My finger slid in and he gasped. Next I tried my smallest butt plug. It took a little while but he took it. I waited for him to get used to it and then tried a larger vibrating dildo. That proved a little too much for his first time so we left that for another visit.
I untied him and, still hooded, he set to work on my cock. He was determined to make me cum and chanced upon the perfect oral technique for it to happen fast. I am not going to reveal the method as each boy has to find it for themselves. Suffice to say he was rewarded with a very sticky mess all over his hand. A job well done!
I look forward to his next visit.
Sky answered one of my ads on Craigslist. He has some experience of sucking cock but nothing much else. When we chatted before the meet he said he would love to be fucked but he would be very tight. Obviously this was going to be a case for toys first.
Sky arrived when we had arranged and was immediately collared and ordered to strip, as is usual for most subs visiting me. It was immediately evident that this meeting was something he was looking forward to. His cock was hard and throbbing as he removed his shorts. I strapped up his wrists and clipped them behind his head. He was at my mercy. After fingering his asshole to see how tight it really was (very!) and gently stroking his pulsing cock, I marched him upstairs where he was hooded and photos were taken. His cock stuck out rigid from his body and was slightly moistened with pre-cum.
The first thing I wanted to do was find out if his oral enthusiasm was real. I made him sit on the edge of the bed, bent his head down slightly and pushed my cock in his mouth. He immediately sucked the head into his warm moist mouth and started to suck like a Dyson. Being impressed with his technique it was time to tie him up and work his ass. With hands strapped to the bedhead and legs pulled up with a spreader bar to expose his tight ring, he was at my mercy. I first climbed over him and fucked his face, his hard cock pointed at me and I gave it a quick lick. Sky groaned.
Another thing that Sky had said he was keen to experience was 'a good thrashing'. Now I know from experience that often what is asked for before a meet doesn't always pan out in actuality so I decided to start gently and work up to harder punishment. So, tied on all fours and gagged, I started working on Sky's ass, first with my hand and then with a paddle. Of course we got nowhere near the 'good thrashing' his imagination had fantasised about but he did end up with a nice warm pair of cheeks!
Next it was time to see if I could loosen his hole enough for my larger toys, and maybe even a cock. But as soon as I tried my smallest butt plug it was obvious he was not going to loosen enough. I gave up on that and reverted to his sucking prowess. I was feeling very 'unhorny' so, after an hour of excellent sucking without me getting anywhere near cumming, Sky gave up and asked for permission to cum. Something he had been holding back from for at least 30 minutes. I relented and granted him permission and he filled my mouth with his warm juice. A satisfactory conclusion to a very pleasant evening.
Shelly is another straight boy who has discovered that there are certain parts of his sexual needs that cannot be met by his girlfriend. We first got in contact a couple of years ago but it took 6 months before he actually managed to get away from his girlfriend. The first meeting, his first with a guy, was quite vanilla although he did take to being told what to do. We resolved to make things a little more kinky the next time.
Over a year later and Shelly's need for man-sex had become strong and he managed to evade the girlfriend and emailed me his availability. Luckily I was available this evening and he headed over, excited and ready to take things a bit further.
In the bedroom he quickly shed his clothes to reveal he was going commando. His cock was already bouncing in anticipation. I hooded him and started to take pictures as agreed. His excitement was evident to see. He had been waiting a while for this. I tilted his head back and pushed my cock into his mouth. Like a muscle memory he started sucking immediately, like it hadn't been a year since last time. I pushed onto his back and tied him to the bed head. His hard cock slapped against his stomach and I slid my cock into his mouth again as I tied him up. I decided to try something new for him. I had to be careful not to leave any marks on him to be found later so I gently nibbled his nipples. He groaned in approbation so I worked my way down towards his throbbing cock. I slid my tongue over his huge exposed head and slid my tongue down the shaft towards his hairy, untrimmed balls. Lifting his legs I wrapped ankle straps around them and clipped to a spreader bar to keep his ass hole available to me. Tying his feet further up, his hole was level with my cock, a feeling he liked, I slapped it against his hole and pushed the head against it. One day he will be fucked.
I decided to try some toys and various dildos and butt plugs were addressed to his virgin hole but he wasn't ready for them. There will be another time.
Shelly had made a request. He wanted a facial. I was happy to oblige and, after the best part of an hour's play, I sprayed his face with my hot cum and then finished him off with my mouth. An even better session than the first.
Scully is straight but realised a while back that he liked anal play. He had met a guy once before but it had been unsatisfactory so he was looking to try again.
We chatted for a while before we sorted our schedules out. He sent me numerous naked pictures to confirm his exhibitionist side and, as he had answered one of my bondage boy adverts, was very interested in being sub.
On the day he turned up I forwent the picture session as he was nervous. As it turned out he was more worried about letting me down rather than about what he was about to go through. His experience of giving oral was very limited and he had been fucked once but only by a very inadequate cock! My selection of toys came in very handy and his asshole took everything I could throw its way.
As he is straight and has a girlf there are certain things that are off limits; anything that might leave marks is a no no.
I tied him up, played with him and got him hard (easily, I might add) and decided the time was right to test his oral skills. He had never sucked a cock before but quickly picked up the technique. In fact he was so good that I came a lot quicker than I expected. Fortunately I am not one of those guys who loses all interest once I have cum and five minutes later he was down sucking while I worked on making him cum.
For a first session it went pretty well
A few weeks later Scully got in contact and asked to meet again. This time he wanted more anal play and also to be hooded. This was to be the photo session.
Again I stripped him and hooded him before fucking his mouth a little more aggressively than last time. He coped admirably and was soon hard and obviously ready to be tied up. Spreadeagled on the bed (my favourite position as you can see from the various pics) his ass gaped and his nice big balls begged to be played with. My tongue went to work on his ass, balls and cock. His breathing was getting laboured as he struggled to prevent himself from cumming. Using only my spit as lube I slid a dildo into him and switched on the vibrate feature. His breathing became heavier and he was finding it even more difficult not to cum. I worked his ass harder as my mouth sucked on his cock more firmly.
The session ended a little earlier than we wanted as he had to get home for an early morning start but I am sure we will meet again to continue where we left off.
After chatting for a while Shaw decided he was ready for a meeting. We had quickly realised that we ticked a lot of each other's boxes. I picked him up from the station, a nervous first time sub and a very inexperienced gay. We chatted in the car but we had already decided online what would happen, or more importantly what wouldn't happen, on the meet.
We went straight up to the bedroom and I removed his T shirt. Looking down at his jogging bottoms it was obvious that Shaw's cock was already straining to get out of his boxers. I stroked it and he jumped as the sensitivity of his member surprised him.
I tied his hands down by his sides, blindfolded him and then started to wrap his upper body in cling film. This is not a straightforward process if you want the sub to continue breathing! Great care has to be taken to allow enough 'give' in the wrapping for his chest to expand. I instructed him to breathe in and hold it at my command. I wrapped him round and round. All the time I could see his cock pointing out of his trackies.
Eventually the time came for me to pull those trousers down to reveal his cock, a wet patch of pre-cum marking the head, straining for release from his tight boxers. I wrapped a bit more film round him until I could no longer put off removing those boxers and releasing his throbbing cock. It sprang free, pre cum drooling from the foreskin. I pulled the skin back and caught the globules of fresh cock juice on my thumb. That thumb was then slid into his mouth where he eagerly sucked it clean.
Once his upper body was wrapped I decided to reinforce the binding with rope and I encased him a second time, his cock still hard and throbbing. The roping continued down round his legs until he was immobilised. Now the real fun could begin.
Completely at my mercy I now started to tease him. Shaw is very tactile and simple things like a finger across his cock sends shivers of excitement through his body. Imagine how he reacted when I donned an exfoliating glove and dragged my finger around his balls, up his cock, around his nipples. The final element of today's play was to be some nipple torture. A couple of pegs, one for each nipple, induced the endorphin rush that I expected. Taking them off created a rush of pain which was easily soothed by his Master's kiss.
Teasing his cock with the glove, my mouth and my hands brought Shaw almost to climax several times. But when he asked for permission to cum (like a good boy) he was refused. I needed him to show total obedience. And he did.
Then, of course, there was the matter of his ass. A complete anal virgin, this was one boy I needed to be gentle with. I reckoned my smallest butt plug might just manage to be a start. As I lubed up and started to work his hole in preparation for the plug I discovered just how erotic he found anal play. He sighed, squirmed and moaned as my finger probed the hole and found its way in. The plug followed easily. However, when I tried to upgrade to a larger plug he wasn't ready for it. I'll try again next time.
It was time for a break so I untied him and we cuddled up for some TLC, a treat always offered to compliant boys. Unfortunately we then realised that time had caught up with us and he had to head back to the station. But, as Arnie says, he'll be back!
Sometimes things happen very quickly. I am completely OK with a sub/slave boi needing to chat a while to trust me. Spike was very intuitive about his feelings for me and we hit it off immediately. We met the same day we first started to chat. Spike was a little different from some of my recent bois in that he was already gay; he was just a kink virgin.
I picked Spike up from his home some 20 minutes from me. This gave us a few minutes to chat in the car. We both agreed on what we wanted.
Spike was very keen to explore his initial taste of bondage in particular.
Once at mine, the heating was on and we went up to start the session.
Spike liked the idea of partial sensory deprivation so I blindfolded him, fitted the hood and tied up the laces at the back. A collar was added along with wrist straps. I slowly unbuttoned his trousers and could see he was very excited already. I lay him down and played with his nipples. His cock bounced a little harder in his pants. I stroked his inner thighs and was rewarded with his cock straining further to be released. Finally I removed his pants and his cock reaared up for attention. Already I could see a drop of pre-cum glistening at the eye. His balls hung low and full.
A cautious finger confirmed that his asshole was ready and willing for probing. I fitted straps to his ankles and clipped a spreader bar between them. Lifting the bar I was able to raise both legs at the same time and expose that rosebud hole of his. It flexed and I bent to run my tongue across the pucker. It relaxed and my tongue probed further. What I had in mind needed more than saliva to lubricate it so a good dollop of KY was slapped between his cheeks and my finger made sure this boi was ready for some anal play.
A butt plug was eased into his tight asshole and he moaned with pleasure. What he didn't realise was that this plug had a couple of surprises attached. Once it was in Spike thought that was the extent of his pleasure. Then I turned it on. The vibrations throbbed around his ass and I could see his cock keeping time with the pulses. More pre-cum oozed from his cock and I leant over and licked it clean. I could see that Spike was struggling to prevent his cumming so I eased back on the butt plug control.
At this point I decided to clamp his cock in a CBT harness. I pulled it as tight as I could, bearing in mind his cock was never less than rock hard during the session. His cock strained against the straps as his ass was shaken and stirred by the plug. Something had to give soon.
Looking to relieve the pressure Spike was feeling and trying to prevent himself from cumming, I untied him and removed his hood. He was still blindfolded so I sat him up on the bed, the butt plug probing deeper into him as the vibrations increased again. His mouth opened and my cock forced itself between his eager lips.
I knew I would cum fairly quickly so I strapped his wrists up behind his head and put him on his back. His mouth opened and I started to face fuck him. His cock was dripping and needed frequent cleaning licks and sucks. Very soon I was close and he, sensing my impending explosion, asked for permission to cum. I made him beg before granting his wish. Just as he was about to unload I filled his mouth with hot cum. He reciprocated within seconds.
Whilst I took loads of picturesof my session with Spike, he, for whatever reason, decided not to allow them to go on this site. Whilst I respect his wishes I do think it is a shame because he is a good looking lad with a nice body and an awesome cock and ass.
Seth and I had been chatting for some months before we managed to synch our schedules to allow a meeting. I suspect he also needed time to pluck up the courage to meet up for the first time.
I went and picked him up. He doesn't drive. On the way back to my house we chatted about what he was up for and what he didn't want to do - always a necessity, in my opinion..
By the time we got home we both had a very good idea where the boundaries were. As it turned out, we didn't get anywhere near his boundaries. There was no need to pull back at any time.
As a complete virgin I assumed that he would not be up for being fucked, no matter how much he hoped for it.
In the bedroom I explained about the collar. Up until the point it is put on the sub can change his mind about anything, even back out if he wants. Once he is collared then he is under my control, to be used as I see fit within the agreed boundaries. Seth understood this.
I collared him. I took his T shirt off to reveal a nice slim torso, pale with flat nipples. Next I shackled his wrists with leather straps and clipped his hands behind his head to the collar. Then there was a blindfold. We had talked about this beforehand because, although most guys find a blindfold heightens the sensations, some panic. I wouldn't want that.
Next I undid his trousers and slipped them off. Topless and in his boxers, I sat him on the bed and leaned him backwards til he was laid flat. A reassuring bulge in his shorts confirmed that he was enjoying himself so far. Next I tied his hands with straps to the bed head, stretching his arms above his head and reinforcing his feeling of helplessness. His cock was straining at his boxers so I freed it with a steady removal of the final piece of underwear.
His cock sprang free and I could see that he needed a shave. While his balls were beautifully smooth there was still a small piece of stubble above his cock. Five minutes with a razor and some shave gel and he was as smooth as a billiard ball. His cock and balls just asking for a tongue to slide along them.
Up to this point Seth had still not done anything with any guy. It was time to end that. I positioned myself by his head, turned his face to me and slide my cock into his mouth for the very first time. He took to it like a duck to water; he sucked my dick into his mouth like a seasoned cocksucker. His bouncing cock confirmed that this was something he had wanted to do for a while.
Seth continued to suck while I leant over and lubed up his virgin asshole. It was very tight and I made sure it was well lubed before I introduced my smallest buttplug to the puckered hole. Gently I slid it in as he continued to suck my cock. As can be seen from the pics, Seth is cut so I did have to guide him on how to suck an uncut cock. He quickly got the hang of it.
By this time it was obvious that Seth was very excited. His cock was rock hard and throbbing, his balls were bouncing around and eager to be emptied.
As it was his first time I took pity on the new boi and allowed him to cum. A nice full mouthful of his hot cum was a great way to finish the first part of our session.
With his cock finally flaccid I was able to put a cbt harness on him. I knew this would be uncomfortable as his cock got hard again and it would also enable him to get hard quicker.
While I waited for him to recover I decided to do a little pup training with him - something we had discussed beforehand. He already had a collar on so it just needed a lead and I was ready to lead him round and teach him not to climb on the furniture until told.
He learned quick and developed a very nice habit of sniffing my crotch and then licking and sucking. It soon transpired that Seth had a liking for being scuffed behind his ears, just like a real dog. Having put down a dog bowl of water for him, it was rewarding to see him on all fours, head in the bowl, ass in the air ready for either punishment or pleasure. This time I patted his rump and fingered his tight hole a little.
As it became obvious that he was recovering and starting to get hard again, it was back to the matter in hand, giving him a mouthful of cum for the first time. He was eager for this treat and did everything he had learned in the last hour or so to make me cum. Eventually his enthusiasm was rewarded and my cock exploded in his mouth. He gulped the hot spunk down with a grin on his face.
Now it was time for my second treat of hot puppy cum.
I tied him back on the bed and got out a tube of lube. Generously squirting on his cock, the cold gel made stimulating his cut cock easier. It also gave his cock a little kick of stimulation. I rubbed back and forth, milking and then edging his hard cock. Eventually I gave him permission to cum and I got another mouthful of hot sweetness.
It was very obvious from the first time I probed his asshole with my finger that today was not going to be the day he lost his final trace of virginity by being fucked. That will wait for another time.
Sacha and I chatted for a couple of days before we met. Sacha had a very clear idea of what he wanted from a session so we agreed a loose format and met up.
Sacha's fantasy was for public nudity followed by bondage. Before we left I fitted a cock ring to his cock and allowed him to get in the car fully dressed.
From previous outdoor adventures I knew a few places which would be suitable but we needed one where we could stay in the car if it got too cold. We drove for about 15 minutes, during which time I ordered him to undo his trousers and then to unbutton the fly on his boxers. His cock was still hard with the cock ring slipped on earlier. Already he was oozing pre-cum. This was going to be fun.
When we go to the place I had decided on I pulled into a gateway and up onto the edge of a ploughed field. It was pitch black, miles from the nearest lights. I made him strip off completely save for his trainers and jumped out to snatch the 'candid' shots through the windshield.
From there I ordered him to spreadeagle himself across the back of the car as though he was going to be fucked. Sacha doesn't get fucked so this was not a comfortable position for him to be in. But he obeyed, like a good boy.
Then I turned him round so he could see the lights of the cars driving along the nearby road. The proximity was obviously stimulating as his cock drooled more pre-cum.
Finally I took his arm and marched him into the centre of the road for more pics. He was getting very nervous as he could see lights getting closer.
Eventually it was obvious that a car was coming down our road and we legged it back to the car. Just in time. The car stopped and reversed back to us. I think he must have thought he had stumbled on a dogging site!
Sacha was throbbing with excitement and I quickly dropped my trousers so that he could show his appreciation by demonstrating his oral technique. I wanted to save myself for later so I started the car and, with Sacha still naked beside me, I drove down the road and back towards home.
As we got nearer the street lights Sacha asked to be allowed to dress. I made him wait until what I judged to be the last possible moment before I stopped to let him dress.
When we got back I quickly stripped him and tied him to the bed before I allowed him to show just how good he was as a cocksucker. His final treat was a face full of my hot cum, liberally wiped by my cock into his mouth.
Sheriden was straight
He answered an ad I had posted on Craigslist looking for straight lads to play with. Due to his having a partner it was difficult to arrange a meeting. But eventually we managed it and he turned up dead on time.
It was obvious from the bulge in his trousers that he was looking forward to the session.
First off I explained that he was free, at any time, to call a halt to the session if he wasn't enjoying himself. As he was up for being photographed I wanted him to feel comfortable. I also explained how the pictures would be posted privately for his OK before they went on the public pages of the site. Then it was down to business before he came in his pants.
I collared him and then removed his remaining T shirt. His lean body, lightly dusted with hair, was a nut brown from working outdoors during the summer. I blindfolded him and he laid down on the bed, his stomach pulsing expectantly as I secured his wrists behind his head. I looked down his body and saw the trail of stomach fur disappearing into his trousers. A treasure trail indeed. As I ran my hands over his chest I tweaked his nipples causing him to inhale with surprise. His trousers seemed to throb and I couldn't wait to finish stripping him.
Unbuckling his belt and unbuttoning his jeans I was aware I was going where no man had gone before. Would the novelty of it overcome his nerves or would I find a flaccid member in need of encouragement? As I pulled his jeans down, fashionably over-sized and thus hiding some of the splendor, his cock tented his baggy boxers and I could see a couple of obvious damp patches of pre-cum. This lad was not going to let trepidation cool his ardour!
His breathing was a little laboured as he anticipated his full disrobing; his cock pulsed and made his tented boxers wave around with a life of their own. I made him wait a little longer and ran my hands up the inside of his legs and inside his boxers. I could see the excitement building in him even further. I grabbed the boxers and pulled them down, releasing the throbbing cock inside; the unretracted foreskin doing nothing to contain the drool of pre-cum splashing across his stomach. As soon as the boxers were off I decided not to waste any of that delicious love juice and, slowly exposing the head, lapped up the pool. The first of several treats for me.
Knowing that Sheriden had no experience with men or of being sub I decided to throw him in the deep end somewhat. Once I had secured his ankles in straps and used a spreader bar to force his legs apart, thus exposing his tight, virgin asshole, I knelt over him and forced my cock in his less than eager mouth. However, it took mere seconds for him to start sucking, taking to it like a hungry lamb. A slight groan from him confirmed that this was going to be one of several new experiences that he was going to enjoy. As he sucked I started to explore his virgin hole with my finger. The initial tightness very soon gave way to a very receptive relaxation and my finger slid in in search of his prostate. It was obvious that this was going to be another new area that would prove popular. I decided to try out my smallest butt plug, just to see if he could take it. I tied his legs up nice and tight so his hole was at just the right height and leaned in to tongue enough lubrication to ease it in. As my tongue hit his puckered up hole an enormous groan came from him. Another new positive experience. The butt plug slid in very nicely. So much so that I went for the next two sizes in quick succession.
To reward him for such compliance I moved round to his head and slid my cock back in his mouth. This time he sucked it in greedily, my balls slapping against his forehead. After a few minutes I withdrew and, working my cock with one hand, slid over his face so my balls were against his mouth. He instantly understood what he was meant to do and slurped around my balls like a pro. I slid a little further down and he tentatively licked around my asshole. A quick slap to his exposed ass and he understood to push his tongue deep inbetween my cheeks and work the hole hard. Then I slid back and pushed my cock back in his mouth as a reward. As an unexpected treat I also turned on the vibrate function of the butt plug. That generated another pleasant groan.
The session continued and I unstrapped him and made him kneel on all fours. His ass was exposed and ripe for play. As I stroked his ass he writhed and undulated with pleasure. I fingered him and opened him up. His anticipation was palpable. Then he got spanked! He wasn't expecting that but stayed hard all the way through it and didn't complain once. My tongue rewarded his acceptance and probed even deeper now he had learned to relax it a little.
Finally I pushed his head down onto my cock and, inbetween sucking my balls and tongueing my asshole, he got his reward of a mouthful of my hot cum. He gulped it down and carried on sucking, sending me into spasms of ecstasy.
Then it was my turn to finish him off. I had him lie on his side and got my vibrator to work his ass while I wanked his throbbing cock. Very quickly he said he was cumming and I clamped round his throbbing dick just as he exploded into my mouth.
As we lay, spent, I asked about his previous experience. He said that he had never had anything up his ass, regrettably, but that he would be buying a vibrator ASAP!
Straight boys who want to experiment are my favorites to play with. I get huge enjoyment out of making them gasp with pleasure when I do something to them they have never tried before.
Sheldon and I chatted for a few days before he visited so we had a good idea for what he wanted to try. As he is straight it really was a case of new experiences. He is usually dominant with women and wanted to experience being a sub for a change.
Primarily the reason for the visit was to get some photos done. Trying out some sexual things was secondary but he was very keen on playing with my bondage gear. The sensible thing was to get him hooded as soon as possible so he could relax and not worry about his face showing up in photos.
I collared and cuffed him and then started the pleasurable task of undressing him. As can be seen in the pics his excitement was obvious and I cuffed his ankles ready to spread his legs and violate his virgin hole. Once his pants were off, his cock sprang free and I raised his legs high up above his head and already tied off wrists. His tight rosebud hole was waiting for me, pulsating slightly as he imagined what was to happen next.
I knelt between his legs and allowed my hard cock to brush against his hole; he gasped a little and I rubbed my head against him. He wondered whether he was about to be fucked. I pulled away and, hopefully, caused him to wonder anew what was next. I bent down and flicked my tongue across his pink hole. He breathed in sharply. I probed a little harder with my tongue and he relaxed. I probed even harder and his hole opened up. I slurped around the edge and left a healthy slime of saliva, just enough to lubricate my finger as it slid in. His cock bounced as I brushed his prostate.
I pulled my finger out slowly and slapped some real lube on before sliding a small butt plug in. It slid in easily and that encouraged me to try a larger one. What Sheldon didn't realise was that this one had added functions. Once it was in I started to suck his cock. Just as I got his groaning I switched on the vibrate on the butt plug. That made him squirm with pleasure!
Just to add to his adrenalin rush I clamped a peg on each nipple while I worked his cock.
I decided to let him have a bit of a rest with the butt plug turned off so, as his cock subsided somewhat, I clipped on a CBT harness. It didn't take long for his cock to start throbbing again and, finally, the end was in sight. While I worked a vibrator up his ass he wanked. He very quickly he came and his first taste of man on man bondage had come to an end.
Serge
Serge is a French student with a long term girlfriend. However, as it turned out, there were things that he felt he was missing out on. I regularly advertise on CraigsList for various things. One of which is a naked massage. This was what Serge responded to. For several weeks we attempted to synchronise our diaries and eventually we managed to marry up a spare evening. After getting rid of his girlfriend for the evening Serge arranged to come and visit. This was easy as he lived very local to me. Almost the next street!
He arrived promptly having jumped in a quick shower. The arrangement was that I would give him a naked massage. Nothing else. Any 'extras' were to be entirely at his behest. He was dubious about this but, as I explained, at the very least I got a wank fantasy out of it! It was obvious he was nervous so I led him upstairs and asked him to undress while I 'went and warmed my hands'. In reality it was an excuse to leave the room so he didn't feel so exposed.
When I returned he was laying face down on the bed but with his shorts still on. Aw he was shy.
With the lights off and the room lit only by the soft glow of a scented candle I poured baby oil into my hands and rubbed them together. Gently I worked the warm oil into his shoulders and down his back. I could feel him relaxing a bit. I asked if I could remove his shorts. I slid them down to reveal his furry ass, pert and legs slightly apart so I could glimpse his balls in the crack.
I slid my oiled hands down his back, passing swiftly over his cheeks and down his firm thighs. Back up again and I discreetly brushed his shaved balls. A few more passes up and down his body to relax him and it was time to see how he felt about ass play. My oily finger gently passed over the pucker of his virgin hole and I heard an intake of breath. Was this good or bad? Before I could ask he said it felt good. I applied a little more pressure and, with lots of oil, I eventually got a finger in and slowly moved it around. This brought more gasps from Serge. I probed further and then pulled out to apply pressure to that sensitive bit between the hole and the balls. This was proving an education for the straight boy!
It was time to turn over. I was expecting him to be flaccid but was pleasantly surprised to find a hard, French, uncut cock waving at me. I ignored it at first and maintained the pretence of a massage by working down from his shoulder to his crotch. Once there I could resist no longer and gently grasped his throbbing cock in slippery hands and, sliding down around his balls to his ass and back again, had him gasping for breath. At this point I removed my trackies to reveal my shorts. Much more comfortable for climbing around the bed.
I was now in a good position to continue working his cock, balls and asshole. I didn't expect any reciprocation and so it was for a while. Eventually he reached over and stroked my cock through my shorts. I asked if he wanted me to take them off. He nodded and I slipped out of them. He oiled up his hand and very soon we were mutually rubbing and probing each others holes.
This went on for some time and he got more and more into pleasing me until eventually he wanted to try sucking me. I was more than happy for that to happen.
I decided that as he had been brave enough to take the plunge and suck me I should give him another pleasant surprise. I had him turn over and gently kissed his ass cheeks. That was nice enough for him but then my tongue slid between them and found his hole. He almost leapt off the bed!
He was getting very near to cumming by now so he rolled over, threw his legs in the air and asked me to continue rimming him. It was the final straight for him and he started gasping and grunting. I just had time to clamp my mouth over his throbbing cock before a stream of hot cum hit the back of my throat. Another satisfied visitor who will be back, I am sure.Silas
Silas is, and still is, straight. We had been chatting for a week and so he had worked out what was available and what he wasn't up for. Basically he was up for anything except being fucked. That was fine with me as I don't fuck.
He arrived early and stowed his bike safely round the back. As soon as he had entered the front door I gave him a final chance to alter his boundaries before I collared him and explained his get-out procedure should he not be enjoying himself.
Once collared he was ordered to strip. His clothes were taken from him, to be returned once we had finished. He stood, naked, vulnerable but obedient.
I then strapped his wrists and buckled his hands behind his back so I could examine him. I started on his back and ran my hands down to his tight ass. I gently probed and found it was virginally tight. He had used a dildo before, but not regularly.
I turned him round and explored the front. His nice full balls hung below an uncut cock. As I pulled his foreskin back to reveal a pink moist head I could feel it move in my hand as it swelled slightly.
I took him upstairs where I prepared him for photographs. It was agreed that he would wear a hood whenever pictures were taken. I was happy with that as it would make him less anxious about what was being photographed.
I knelt him down and attached the ankle straps to him so I could buckle his hands to his feet. On his knees he was at just the right height for his first blow job. I pulled his head back so his mouth automatically opened and forced my hard cock in. He gagged at first and did that odd thing for first timers, he had loads of saliva in his mouth. But he very quickly got the hang of it and within minutes was sucking like a veteran.
I then placed him on the bed and, spreadeagled, tied him to the bedhead, shackled him to my largest spreader bar and hoisted his legs up and tied them to his hands. His virgin asshole was exposed and available for my use. Before I went to work on his rosebud I wanted to make some use of his nipples. I knew they were sensitive so I clamped some pegs on them. This elicited a sharp intake of breath as he decided he liked the pain. Next I encased his cock and balls in a CBT harness. Again, a new experience which he seemed to enjoy, given the sudden amount of pre-cum that was expelled.
Then there was his beckoning hole. I warmed him up to the idea of some anal pleasure by sliding my tongue around it and gentle probing the hole. He knew how to do it but I don't think he had been on the receiving end before. As he relaxed I used a finger to gently widen the hole until I was sure it would take a butt plug. I lubed him up and slid one in. He gasped but got used to it. Then I turned on the vibrate feature. That was nice for him.
Now that he was used to anal stimulation I swapped the butt plug for a dildo that vibrated. That hit the spot and I climbed on top of him to allow him to work on my cock, balls and ass while I used the vibrator on his excited hole.
While his oral skills with regard to my cock came to him as a natural reflex it was his rimming aptitude which surprised me. Laid underneath me joyfully wrapping his mouth round my cock I slid further down and he found my balls to play with. It was a small progression for his tongue to play around my hole and he found himself rimming his first male ass. He was surprisingly good at it, as well, and displayed an enthusiasm that matched his expertise.
Unfortunately something went wrong with his mood and he asked to stop as he had lost his enjoyment for the session. In fact he had suddenly decided that gay sex was not for him. That is a shame but I respect his feelings and we stopped.Stan
Sometimes nerves get the better of us all. Such was the case with Stan. We hadn't been chatting for long and maybe we hurried too fast for him.
Stan was very inexperienced, he had only ever wanked a guy, so visiting me for a full on bondage and photo session was always going to be intimidating.
We had arranged for him to visit after work last week but, despite him having my email, address and phone number, he failed to show. I assumed he had lost his nerve but just not turning up was, I felt, very rude. I emailed him and told him so.
A few days later he sent me a very contrite email asking for a second chance. I was unsure but decided to set him a task to see if he was serious about turning up this time. I asked him for a picture of his cock, as it was at the time of asking. Within minutes he sent it. Flaccid, it was just as I had asked. We arranged for him to come over in an hour. True to his word he arrived on time.
He was very nervous but I could immediately see that he was very sub and compliant. As is usual, I explained the rules about his welfare and how pictures would be taken. I then ordered him to strip and his clothes were taken away until he was due to leave.
As can be seen from the pictures he was obedient and subservient so examining him was a joy. His nerves showed in his flaccid cock but a gentle pulling back of his foreskin awoke his member and he rapidly got a semi hard on. This tumesced even more when I probed his tight virgin hole.
Grabbing his collar I propelled him up to the bedroom where I hooded him (for ease of photographing him anonymously) and blindfolded him (for the fun of not allowing him to see what I was doing) before laying him on the bed and securing his spreadeagled arms and legs in a very vulnerable position. For a boi who had never had any sort of anal stimulation his virgin hole was very sensitive to my finger, my cock and my tongue. He squirmed very pleasantly at every touch and probe.
As my tongue worked its way around his nether regions he moaned even more. His cock arched and the swollen red head burst from the foreskin oozing pre-cum and demanding attention.
Carefully manoeuvreing myself over his head I lowered my cock into his mouth. Another first for the boi, he took to oral like a duck to water. His very willing mouth worked my hard cock with very little guidance from me and he soon progressed to my balls and then finally to the source of so much of my pleasure. My ass. There he showed that lack of experience can easily be overcome by enthusiasm. His determination to please me was obvious and he was letting nothing stand in his way.
He was so excited that I decided to see how his asshole would cope with a butt plug. The first, small one, slipped in very easily but the next size up proved too uncomfortable. That is fine. I don't expect him to cope with everything at one go. However, I did discover that anything that attacks his rosebud hole will send a shiver of expectation through him. It doesn't matter whether it is a finger, a tongue or especially my cock, anything pressed against his hole is eagerly accepted. One day he wants to be fucked and he will love it. I just need to train him to relax and allow anything that will give him pleasure to enter him.
Gradually I untied him, one piece at a time until he was completely free. While his mouth was permanently clamped to my cock I worked on his cock, balls and asshole until I had him at the point of orgasm. Time after time, as he writhed in exquisite ecstasy, I stopped, edging him to the brink repeatedly as he squirmed with hyper-sensitivity. Eventually he could hold back no more and asked for permission to cum. Given it, his hot load filled my mouth. I was overjoyed
He collapsed in a heap on the bed so I gathered him in my arms and allowed him to rest. Even then he was hard put to keep his hands off my cock.
Eventually it was time for him to leave but, as a farewell gesture, his goodnight kiss to my cock awoke the beast and a few minutes later he got his reward. His very first mouthful of hot cum, which he dutifully swallowed with relish.
I look forward to our next session.Shane
I regularly advertise on Craigslist under a variety of subjects. One of those is for exhibitionist who want to have naked pictures taken. Shane responded to that ad but, as we chatted over a few days it became obvious that he wanted much more.
We tried to arrange a meeting for earlier this week but I had previous commitments so we rescheduled for today. To be honest I did expect him to cancel at the last minute but I was very pleasantly surprised when he turned up on time.
The agreement was that the role play would start the minute he walked through the door and so it was. I closed the door behind him and, as is my wont, explained how, once he was collared, he was mine to use as I see fit within the boundaries we agreed (in this case most definitely no marks as he has a girlf). One last time I asked him if there was anything he did not want to do (sometimes boys say they don't like to rim or swallow). He confirmed he was up for anything and everything.
I took up my camera and ordered him to undress and put his clothes in the box provided. He would have them returned when he was finally uncollared.
The first things I usually do is to test a boy's obedience and compliance. I told him to turn round and ran my hands down his back and around his buttocks. Then I slid a finger inbetween his cheeks and found his moist hole. We had ascertained that he had had a single drunken sexual encounter with a guy. Now he told me it had resulted in him getting fucked. That explained his less than resistant asshole which had quickly relaxed for my probing finger. I turned him round and slid my hand down to his very hard cut cock and nice tight balls. He drew a breath in when I rolled a finger across the already dripping head. Pre cum was to turn out to be a major product of his excitement. Yum!
Having marched him upstairs I shackled his wrists and hooded his head. He was quivering with excitement and nerves. Later he told me he was anxious to be a good sub. By the time I had tied him to the bed head his pre cum had reached flood proportions and his belly was awash. Scooping a generous portion onto my fingers I slid them into his mouth where he started to suck them clean.
A quiet pep talk in his ear readied him for his first taste of being used. His cock throbbed in anticipation as I tweaked his nipples and then went further south to his cock and balls. Just to excite him even further I ran my tongue around his balls and then up the shaft of his cock and around the hard, juicy head. It throbbed with anticipation.
Next it was time for my favourite position. His ankles were shackled and a spreader bar clipped to it to ensure his legs were apart and his tempting hole was easily accessed. Without Shane knowing exactly what I was doing I slid my vibrating butt plug into him. It went in easily enough but when I turned it on the boy came close to hyperventilating. He had never experienced such pleasure and was relishing every buzz.
Now it was time to test his oral technique. I turned his head sideways and slid my cock into his mouth. At first he wasn't sure how to suck but he soon got the hang after some pointers from me.
I decided to change his anal stimulation and removed the butt plug and replaced it with a conventional vibrating dildo. Being able to manually position it inside him meant he got even more pleasure from it. Holding the dildo in place I maneuvered myself around so I was kneeling over his face and rammed my cock into his mouth. Then it was a case of moving around so he could work my balls with his mouth and finally my ass. He picked up rimming the best and had me gasping with pleasure. All the while I was taking pictures which are now on his page.
Eventually, time having run away with us, he needed to leave. I ordered him to cum and, like the good slaveboy he is becoming, he took a minute or so to comply and leave me with a nice mouthful of his hot cum.