I had an amazing session this weekend with a very shy, quiet boy who I’ve been talking to for about a year.

He’s made a time to come over on at least three previous occasions – but what made this time different is that he actually turned up! 🙂 He’s pretty adorable (when he shows up). He was incredibly nervous when he arrived – we broke the ice with cups of tea and a game of ‘cards against humanity’. Those of you who know me in real life will know that despite the fact that I can play pretty hardcore, I am actually a big adorkable bear. He worked this out and relaxed.

When I thought he was ready, I dragged him to his feet and popped a fur lined leather blindfold over his head. He had almost no previous experience – just some blow jobs in high school. This was essentially his first time at doing anything hardcore. An eighteen year old with a virgin ass. 🙂 It’s hot but a lot of pressure for me as you want to give him a fantastic first time. I started the way I start with a lot of beginners – with a lot of touch. I left him fully dressed while I ran my hands all over his body. He was shivering with a combination of fear and pleasure while I explored his body. I moved onto running my hands up under his shirt – before slowly pulling it over his head. His chest and stomach were smooth and he had a really lean body. After more teasing with my hands, I pulled my own shirt off and we ended up chest to chest. He could feel the heat of my body as I ran my hands over his body and pulled him close.

Over the next fifteen minutes I slowly undressed him – with lots of caressing and body contact. I nibbled on his ears and teased them with my mouth. When I dropped his pants I had quite a large surprise (pun intended). Standing up tall and proud in his black Bonds underwear, with an orange band, was a very impressive cock – that was exceptionally hard. I ran my hands over it – just teasing it really. I took off his pants from around his ankles so he was just there in his jocks and matching socks. Amazing sight. I removed my own pants and he experienced me rubbing my hard cock in my own jocks against him. I wrapped his arms around my neck and lifted him into air. He wrapped his legs around my waist as I teased his ass through his jocks. The fur lined collar was run over his body. It’s an amazing feeling for the boy feeling a strip of fur being run up their naked body – over this legs, balls, cock, stomach and chest before it gets fastened around his neck. I really wanted to kiss him, but I wasn’t sure that he was ready for that – so there was a lot of nuzzling and fondling.

When I finally removed his jocks, his cock was really impressive. He had a foreskin that’s a little too tight – but that’s quite common on young guys and I’m sure he’ll stretch it out in no time. I attached my red leather ankle and wrist cuffs and clipped his hands behind his back – and turned up the fondling a couple of notches. I ran my tongue over his body and teased his nipples. I then fitted him with a leather harness. It was time for him to suck cock. He had sucked off one of his mates before, but never anyone else. On his knees he removed my jocks as I sat back in my arm chair. He grasped my cock and stroked it for a few minutes. When I told him to suck it I thought it would be quite hesitant but it took about a second and half before the head of my cock was in his mouth. He wasn’t bad at all – for someone so inexperienced he really remembered to use his hands as well as his mouth – very impressive. Like so many other young, slightly nerdy guys, he had done the research and knew what was expected. I was impressed. After half an hour of cock sucking it was time to move him to the bedroom. I picked him up and carried him there – with his arms and legs wrapped around me. I lowered him onto the bed. I pinned him to the bed – holding his arms down while I nuzzled his neck. He seemed to really like it. He had seen photos of my new custom bondage device and had been eager to give it a try. I grabbed his chest harness and pulled him until he was sitting up. I slid the two back straps under him, lay him back down and commenced the process of buckling him in.

There are sixteen buckles on the device – so working as fast as possible it still takes around three minutes to get it on and adjusted. I took my time so he could appreciate each strap being fastened – with his movement being increasingly restricted with each and every step. It was a beautiful sight. His lithe teenage body visible between the thick black straps. His awesome cock was still absolutely rock hard. The orange silicone ball stretcher was still holding his balls down away from his body which made his sizable cock look even bigger. I started to lightly touch every square inch of his body that wasn’t covered by the wide leather straps. He seemed to really enjoy the light touches all over his cock and balls. I lay beside him as I touched his body.

He has almost no previously experience of kissing and made the amateur mistake of opening his mouth way too wide. I corrected him and got him to close his mouth so I felt less like a little fish about to be eaten. The kissing started slow and sweet. Little butterfly kisses until he relaxed. My tongue running over his lips. Our lips parting and our tongues dancing with each other, and then as his confidence grew they started fencing with each other. A mini sword fight conducted inside his teenage mouth. We did this for quite a while until I decided it was time to remind him again that I was in charge.

I connected the violet wand and there was the normal crackle and buzz of electricity as the wand started to glow orange. I touched my arm a few times as I adjusted the intensity to ensure it wasn’t too painful. As intense as it was when I applied it to my arm I knew it would feel ten times more intense when applied to someone who was blindfolded and helpless. I ran the probe over his legs and arms and over his torso. I got a really strong reaction when I played the sparks over his nipples. I pulled him until he was in a sitting position and I kneeled behind him holding his head up. I removed the blindfold and it took a few moments for his eyes to adjust to the intensity of the bright overhead lights. He was in a perfect position to see the leather restraining his young body – and then I brought the violet wand into his field of vision. I let him see the crackling wand before applying it to his arms, legs, chest and nipples. He moaned again with the nipple play and looked anxiously towards his rigid cock as the wand moved closer. The wand caressed his cock gently – as the sparks flew and tormented the teenage skin. I replaced the blindfold and lay him back down as I continued to torment him with the violet wand.

I left him alone for a while before I unbuckled him – not a fast process – and pulled him to his feet. I made out with him as my hands wandered over his body. I put his hands around my neck and lifted him off the ground. He clung to me as I leaned forward and gently lay him into the sling. His ankles were slipped into the padded stirrups and his wrists were buckled into the restraints. I kneeled between his legs and gently spread his ass. Amazing ass. A teenage virgin hole, tight and pink with a light dusting of hairs. I grabbed the wash cloth I had soaked in hot water and started to rub it up and down his crack His ass looked clean even before I started and seeing it glisten with hot water made appear even better. I spread his cheeks and for the first time in his life he experienced the sensation of a tongue running up and down his crack. I flicked it over his hole repeatedly while reaching up with my hands to fondle his body. Eventually I drove my tongue in as far as I could. The pace and intensive increased – it got to the point where I was tongue fucking his ass while he swung backwards and forwards in the sling. It was pretty damn hot and his cock was now oozing precum. Eventually it was time to go further. He lay immobilized as he heard the snap of the rubber gloves going on.

I practically poured lube over his cock and balls and let it drip down to his teenage ass. I started my stroking a single finger up and down his ass – teasing his hole. With each stroke I increased the pressure and my finger caught on his boy pussy – not penetrating it but certainly making its presence felt. I made sure my finger was well coated with lube and slowly slid it into his ass. A few slow strokes followed before I felt for his prostate – which was very obvious. I asked him if he had ever stimulated his prostate before and he replied he hadn’t – a split second later his mouth was open in a soundless moan as my finger caressed, teased and probed the fun button in his ass. He had one of those reactions where you are pretty sure he’s enjoying it but not totally sure as he hasn’t actually said anything. I questioned him and he rather breathlessly confirmed he was having a very good time. I worked his ass for a while. Because he couldn’t see he didn’t realize just how wide I had gotten his ass. When I asked him how many fingers he thought I had in his ass and he guessed two, I probably shouldn’t have told him there were four up there – as he immediately clamped down on my fingers. I worked him up to five fingers and was certainly getting more vocal reactions.

His ass was getting a little tender and so I eased up on playing with it as I continued to play with his cock, balls, nipples and mouth. His hands were still restrained when I pushed my cock between his fingers – he got the idea quickly and I fucked his hand as he lightly gripped my hard-on with his slender fingers. It was time for him to blow his load. I started to play with his ass and he indicated it was a bit sore. I paused but decided to ignore his protestations as I knew he wouldn’t last too long before coming. My middle finger attacked his prostate as I slowly stroked his cock. I lubed his cock well to reduce friction and so therefore torment him a little longer. It was pretty clear when he was about to come even if he wasn’t making any sound.

His prostate swelled and his rigid cock felt ready to burst. He blew a massive load. Jets hit his face, stomach, chest, arm and one even flew over his head. Normally guys with average sized balls don’t blow a load this large, even when they are horny teenagers, so I guess he was having a good time. He lay there panting and I gave him a few minutes to recover in the sling.

When the blindfold came off he looked almost shocked. It was definitely a “back to reality” moment. In the shower afterwards he had a slight “kangaroo caught in the headlights” look. In many ways bdsm can be easier than physical intimacy. The juxtaposition between what we had done and having a smiling bear rub soap over your body was clearly a little confronting.

I really enjoyed our session. He’s a great guy – far more articulate online than he is in real life but I’m confident that’s going to change. He’s an intelligent thoughtful guy with a big dick and an adventurous attitude. His university years are going to be incredible. I’m looking forward to seeing him again. I’ve talked before on soxster.com about how bdsm and sex can be positive life affirming events. I think that this kind of play will really benefit Red. It should give him confidence. I want him to walk a little taller and let more of the wit and confidence I see online out for the world to see. I want to help him, in some way, to become a more outgoing boy who is sexually confident and knows he can please someone in ways they can only begin to imagine. I want him to take that sexual confidence and apply it to life.