Well I had an very good evening with Charlie – that stretched into the next day. I don’t normally have boys stay the night, so that fact I did shows that it was a VERY good session. Not as hardcore as I normally do but that’s because the weather was insanely hot.  🙂  Here is Charlie’s recollection of the session – pics to follow.  😉 I’m really looking forward to playing with his teenage ass for a full weekend.

A few days ago, I was finally able to meet Andrew, who I’d been chatting to on and off for a month or so. I hadn’t had a meet for a couple of months, so I was pretty keen to play with him. As a visitor to Melbourne, I found it a little difficult to navigate the city, and after only getting lost a couple of times I was finally able to find his apartment. I know that this is something that gets said a lot, but as he opened the door I was immediately struck by his height. I’d like to imagine that I’m fairly well off height-wise, at about 6’2, but he absolutely towered over me.

We had a bit of a chat, and soon sat down to watch a couple of scenes that Kareem Abdul-Jabaar Andrew had filmed. After a couple of videos, Andrew came up behind me and placed a blindfold over my head. I could feel the excitement building within me, with the knowledge that I was finally about to get the opportunity to play with him. I was soon made to strip down to my red-black jockstrap (which merited a “Good choice” from him), as he inspected my body. I felt a bit helpless, standing in front of this giant of a man as he judged and looked over my body.

Eventually he moved on from this, placing leather cuffs around my wrists and binding them together behind my back, before placing similar cuffs on my ankles. At this point he pulled me up close to him, with his arm pulled tight around my throat. He whispered a whole range of things into my ear, including how my ass would belong to him, and how he would turn me into his slut to use, by himself and with others. Again, I felt incredibly helpless; being held tight by him unable to move, but at the same time I was incredibly turned on, knowing that just at this moment I was completely under his power. By this point he had also stripped down to a jockstrap, and with my bound hands I rubbed his cock through the fabric.

Soon he untied my wrists and pulled my jockstrap down, placing something tight around my balls. It felt quite strange and rubbery, and I recognised it from the shape as the orange silicone ball stretcher that he often placed on the guys he played with. He then pulled me over to a chair for some spanking and whipping. I’ve always been able to take a solid spanking, so I was keen to show him how well I could take it. He used a whole range of whips and paddles on my ass and back. There were four different whips; a leather one, a swede one, a rubber one, and a cat-o’-nine-tails. I counted out the strokes, though he didn’t go too hard, presumably because I had made it clear how inexperienced I was. I anticipate a much harder time in future meets. He used fewer paddles, ending up only spanking me with two. One was just a regular paddle, which again I counted out the hits from, while the other was a more interesting proposition. The different sides of the paddle had different materials on their surfaces – one leather, one fur. It was interesting in that it was a bit of a mind-fuck, as not knowing whether the next hit was going to be painful or soft was quite disconcerting.

After quite a long session of paddling and whipping, Andrew dragged me over to his chair for a long session of cock sucking. He initially made me lick and suck his cock through the fabric of his jock strap. This was pretty frustrating, being so close to it yet being unable to get to it. He taught me to run my fingers along the inside of his legs, as well as other things that would apparently increase the quality of the blowjob. I could feel his cock swelling beneath the fabric, and eventually he removed the jockstrap, allowing me to finally take his cock in my mouth. As I’ve said multiple times, his cock was huge, and it took some effort to take it all, and I gagged as it touched the back of my throat. He alternated between just letting me suck in and placing his hands behind my head so he could fuck my mouth. During this I continued to run my fingers along the inside of his legs, and rub the area between his balls and ass, which apparently felt good. I also was told to pay extra attention to his balls, which I did via licking and rubbing. Despite my relative inexperience in comparison to some of his other boys, Andrew seemed to think I was doing a good job. Throughout all of this he continued to tell me how I would be his boy, and my ass would be his to own, which only spurred me on in my cock-sucking effort.

About half an hour later Andrew stopped me, picked me up off my knees, and led me into the bedroom. My wrists and necks were forced into what I recognised as a set of stocks, and my ankles were tied to the bed, leaving me mostly immobile. He took a couple of pictures, and I heard what sounded like an electrical crackling. I then felt an incredibly weird sensation run over my nipple, and I guessed that Andrew had gotten out the violet wand. He ran the device up and down my body, and while for the most part it wasn’t an especially painful sensation, when he ran it over my cock and balls it really intensified, and I found it kind of difficult to take. Thankfully, he only used it briefly, and soon left me alone on the bed.

As I was lying on the bed I could hear Andrew setting something up. I was slightly confused initially, as I could hear what sounded like chains being moved around, but I quickly realised he was setting up his sling, and I realised I was about to have my ass played with, which was a crazy turn-on for me. I already knew that he had a ridiculously big cock, and now I was going to get the opportunity to get stretched out by it. I was, however, a bit nervous. I’d only ever been fucked a couple of times, and hadn’t had any meets in a fair while, so I was worried that I’d be too tight and embarrass myself, especially since I knew Andrew knew a bunch of teens that could take fists like they were nothing. He released me from the stock and ankle restraints, and slowly helped me off the bed and lifted me into the sling. He placed my ankles in the stirrups and strapped my wrists into some restraints, and I got myself ready for what I knew would be an intense session of ass play.

Soon I felt the first spurt of cold lube run down my balls, and Andrew left it as it ran down towards my ass. As the lube touched my hole he slipped a single gloved finger into me. I’ve always enjoyed assplay, because I enjoy the sensation of having something in my ass, and this was no different. The blindfold obviously completely stopped me from seeing anything, and it seemed as if all the sensations I felt as he played with my ass were amplified because of this. It was difficult for me to tell what he was using in my ass, but I was pretty sure he was just stretching me out using his fingers. At one point he asked me how many fingers I thought he had in my ass, to which I answered that I thought I only had one. I was surprised to learn that I had all five fingers in my ass, which might seem underwhelming for some of you, but was impressive to me, especially given the ease at which I was taking it. He quickly moved on to rubbing my prostate with a single finger, which was a first time experience for me. It actually felt really weird, though not necessarily bad. I don’t think I could have taken much more of it, but luckily it was at this point that he announced that it was time for him to fuck me.

He poured some more lube over my hole, unbound my hands and gave me some amyl to prepare myself for the fucking. He then put a condom on and lubed up his cock, and soon I could feel the head of his cock pressing against my hole and slowly entering me. After he’d shoved the entire length of his cock into me, he started to pound me, getting quicker and quicker. He pulled me onto his cock and moved my legs around, and I was almost in disbelief that I was finally being fucked by him, and that I was actually taking such a big cock. I even checked with my hand that he’d actually gotten the whole thing in. I’d never taken such a huge cock before, and eventually the pain started to overpower the pleasure of being fucked. I asked him if we could take a bit of a break, and he gave me a final ten extra hard thrusts, before letting me out of the sling.

Being Australia, it was ridiculously hot, so Andrew had booked the night in an air-conditioned room at the Gatehouse, which was a fetish-hotel type thing. We went out and had dinner at a restaurant, and eventually walked over to the Gatehouse. After arriving we decided to have a quick shower, and Andrew also decided he wanted to rim me. As soon as we got in the shower he span me around, pushed my legs apart, and began to rim me. He did this for maybe 20 minutes before we went back to the room. The room had two floors; one with a sling and some bondage equipment, the second with a bed. We went upstairs to the bed, where he got me on my back, and pushed my legs up to my chest so that he could really get an open angle to my hole. He spent about 20 minutes rimming me in this position, really working my hole over with his tongue, pushing in on and working it.

After this we went downstairs, where we spent about an hour doing some bondage. It was ridiculously hot that day, so the amount of bondage we could do was limited, but we did manage to get a bit in. First, he tied me to a padded section of the wall using large amounts of rope. He then used the whip again across my chest, and it was a turn-on for me knowing that I was unable to get away from this punishment. After 20 minutes or so he released me, and moved me over to what I was later told was a fuck-horse. After tying me down, he (unfortunately) didn’t fuck me, but gave my ass a working over with a paddle, leaving it red and sore.

After this the pace of the session really changed and slowed down, which I really enjoyed. Basically, we went back upstairs spent the next hour or so cuddling and spooning. I spent a bit more time blowing him, and I also gave him a bit of a massage, running my fingers lightly over his body. After some more rimming, and him rubbing his cock up and down my ass crack, he decided he wanted to give me another go in the sling.

After helping me into the sling, he again placed my feet in the stirrups and tied my hands to the chains connecting the sling to the roof. He once again lubed up my ass and slid a finger in, but this time it felt different, and much more painful, even though it was only one finger. Apparently, I may have had a negative reaction to the lube, which is supposedly quite common, so Andrew decided it was time to stop the ass play. Instead, he settled with thrusting so that his cock run up and down my ass crack, over my hole. While this may not have been as good as a rough fucking, it let me know what I was in for next time, when I’ll be more ready and prepared for it.

Eventually he untied me and took me back to the shower. After rimming me some more, he decided he wanted to cum, and forced me on to my knees, where I licked his balls as he jerked off. He soon blew his load, getting some of it into my open my mouth but blasting most of it across the rest of my face. He pulled me up and giggled at my cum covered face, kissed me, and helped me wash it off. We went back to the room, where we went back up onto the bed. He rimmed me while I jerked off, and I quickly sent a huge load out over my chest, and I collapsed back onto the bed, exhausted after what had ended up being basically 9 or 10 hours of playing, albeit with a nice Chinese dinner as a break. We soon fell asleep together, cuddling as we slept. He woke me up early in the morning for a bit more rimming and blowing, but it was soon time for me to leave and him to go to work, so we said our goodbyes and parted ways.

In summary, it was an incredibly experience for me. As someone who really hasn’t played very much, it was great to have such an experienced teacher helping me along the way. We’ve already made plans for me to fly back to Melbourne for a weekend, in which I can imagine we’ll get quite a bit done. I’m using a few plugs and dildos to try and stretch myself out, because I’m pretty keen to take a long, hard fucking this time, which I can imagine Andrew will be oh so happy to provide.