We were lounging around in front of the computer and TV and I was trying not to fall asleep. David was on Grindr – as he is on and off for most of the day. He started chatting to a few boys and quickly fell into a detailed conversation with an eighteen year old named Kaden.
I didn’t think it was likely to go anywhere. The chances of finding, at short notice, a cute hot boy who was willing to play then and there, who was into twinky boys like Dave and a mid thirties bear like me, were always going to be slim.
But they talked and talked. When asked if he liked bears he responded that he loved them. He agreed to come over … but that there would be a short delay while he waited for his phone to charge. He said he was on holidays with a friend. We didn’t know it then but he was actually waiting for his phone to charge so he could find his way to us and back to the hotel AND so that his parents had a chance to go to sleep in the next room.
When Kaden said he was on his way I was surprised. I suggested we blindfold the kid when he arrived to make it more exciting for him. With his sudden arrival I couldn’t find the right blindfold and instead handed Dave a more advanced one. The blindfold has separate circular leather eye pieces lined with black fleece. It’s more difficult to use as it has a buckle rather than elastic and it can take some time to correctly position it on the boy’s head.
David went downstairs to collect him. Not believing until that moment that he would really show I rushed to the bathroom to piss and wash my cock. And gargle some mouthwash so my mouth was fresh for him. And then Dave knocked at the door.
Kaden was stunning. Standing there in my door way was a blindfolded eighteen year old boy with a mischievous grin.
He was wearing a black leather jacket and a white t-shirt, but one with a long v neck that made him look half undressed already. He was stunning – soft hair and cute as hell.
He had this quizzical mischievous look on his face that make it look like he was smiling the whole time.
David started caressing his body. Kaden found David’s lips and it was on for young and younger. It was a beautiful sight.
I slowly included myself in the proceedings. Caressing Kaden’s body while he made out with Dave. Running my hands over his body. Nuzzling his neck until he turned his head and locked lips with mine.
It took a lot longer for us to all get our cocks out than I would have thought. No one wanted to rush something so good.
Lots of fondling, lots of kissing. Exploring his mouth with my tongue while I wrapped my fingers through the hair on the back of his head and held him in place. I was conscious of the minty taste of my mouth from the mouth wash. It masked the sweetness of his saliva for a few minutes … until the taste of the mouth wash gradually wore off and I was left tasting just him. I don’t know why the mouths of teenage boys taste so sweet but they do.
I don’t think there was more than ten seconds where Kaden wasn’t kissing either David or I.
The blindfold kept on falling down until eventually I turned down the lights and let it fall off. I sent David into the bedroom to turn off the bedside lamp so that the room was lit only by the lights outside my window.
David led him to the bed and pulled Kaden on top of him. Chest to chest they made out as David wrapped his legs around him and made sure Kaden’s hard cock was as close to his ass as possible. I couldn’t resist, I ran to the laundry and grabbed a clean hand towel and soaked it quickly in hot water in the bathroom basin. Kaden’s ass was facing the door when I walked in. Running the hot wet cloth down his ass crack I made sure his teen butt was perfect. Throwing the cloth out of the way against the wall I started at the top of his crack and licked my way down to his hole. Still hot and wet from the washcloth I pushed my tounge against his butt. Tickling his hole with short rapid licks and then long strokes up and down his hole. Finally trying to push my tongue up his butt but being resisted by his tight hole. His very tight hole.
I love to hear stories about how guys lost their virginity. This has two benefits. First, the stories are often incredibly hot. Second, it’s a great way of judging a boy’s experience. There really is a pretty consistent correlation between how a boy lost his virginity and what he is into. If they suck cock for the first time later in their teen, say 18 or 19 then they’ll like sucking cock and maybe even love it, but they won’t need it and crave it. He said he’d first been with a guy when he was fifteen – and it showed.
David asked him he had ever been in a sling before and he hadn’t. He seemed reluctant to try it. Even as a top. But as the night progressed, his mind changed.
After being rock hard since he arrived the pressure of being prepared to fuck David took it’s toll and he went soft. Too nervous to stay hard.
So it was suggested that Dave get fucked in the sling as it is an easier experience for the top. He agreed, with a slight sense of reluctance but intrigue. While David and Kaden made out I pushed the queen bed that David was supposed to be sleeping on at that moment up against the bookcase and dragged the sling out of the bottom of the cupboard. The sling clips onto four rings bolted into the room.
David climbed into the sling and I pushed Kaden between his legs as they dangled from the stirrups. Kaden leaned forward and mashed his crotch into David’s ass as he leaned forward and kissed him.
I watched them make out. It was too dark to see every expression but I’m pretty sure that Kaden realised the advantages of being in the sling. And probably started to realize that he wanted it too.
I nestled my cock between Kaden’s cheeks and mock fucked him while he made out with David. He pushed back and clearly wanted more.
I grabbed the lube from the shelf poured some on my fingers and started rubbing it up and down his crack. Teasing his hole with my fingers. Not actually pushing into him but just teasing his hole.
He wasn’t resisting and was actually kissing David and moaning harder and harder.
I grabbed more lube and slowly pushed a finger into his ass. He moaned and kissed David even harder. Standing behind him the angle for my finger wasn’t quite right, so I pushed my thumb into his teenage butt. He moaned but not as much as when I found his prostate and started working it.
Has anyone ever worked over your prostate? I asked. Nah uh, he groaned in pleasure as I pounded it with my thumb. And you like it? I asked sweetly. Yep, he moaned – no words just a guttural cry. I like it when boys can’t express themselves while I pound their prostate.
Any reservations he had about getting in the sling were being slowly and permanently destroyed.
Kaden’s ass was different to most guys. He had a tight young ring but as I pushed my fingers into him there was a large, soft, open cavern inside. Most teen asses grip all the way inside. With Kaden you could tell that as soon as his ring relaxed there would be an awesome long fuck.
I rolled a condom down my cock and stroked my cock up and down his crack. Kaden was understandably nervous as our previous playing had shown him that my cock was definitely in the top 1% for thickness. It’s a real challenge – even for experience boys. For the eighteen year old boy bent over in front of me it was definitely going to be a tribulation.
He kept making out with David who was still in the sling. This meant he was bent forward at just the right angle for me to slide my cock slowly into his ass – so I did.
I slowly fucked him as Dave distracted him. His tight ring kept fighting me until quite suddenly it totally relaxed. That happens with a lot of teenagers – their asses try to keep you out until they give up completely and relax. Older guys do the same thing but it isn’t as obvious. When it happens, it is a sign you can really pick up the tempo.
I slowly fucked him, alternating with some quick rabbit fucks to ensure he didn’t take my cock for granted.
After five minutes I was pretty sure any resistance to being fucked in the sling would have been destroyed and I told Dave to get out and let Kaden have a turn. I didn’t phrase it as a question. More like a direct suggestion. Dave rolled out and I pulled my cock out of Kaden’s butt so he could take his place. Kaden was obviously excited as he lay back into the leather cargo net sling. Dave and I each put one of his ankles into the stirrups and I took my place between his legs. Any tiredness I may have been experiencing had definitely disappeared when I saw that beautiful sight of a teenage boy with an impish grin and an open hole waiting to be fucked.
David knew from experience that a sling fuck can be more intense and took up a position next to Kaden’s face so that he could make out and distract him when required.
When I started fucking him properly he did that thing that so many young guys do when they get fucked – he started jacking his cock for all it was worth to distract himself. Good idea but makes them cum way too fast for my tastes. I’ve always been a pound them for a long time rather than rabbit fuck them for a minute and blow kinda guy. Hold his hands I told David. He grabbed Kaden’s wrists and held them above his head and leaned in and kissed him. When boys are tied up or have their hands held tight they suddenly they realize it’s about the journey not the orgasm. The sensations change. The focus changes. It’s about the sensations – not how close or far from orgasm you are. Kaden didnt resist much as his hands were pinned down safely out of reach of his cock – a small moan that was clearly code for “oh god – really?” before being stifled with David’s tounge. To let him get used to it I fucked him slowly with long strokes. Powerful and rhythmic with lots of lube. Intense but predictable.
I slid into his ass and continued one of the best fucks of my life. I started slowly and building up the intensity. We tried every variation of style you can imagine. Fucking with his legs spread wide in the stirrups. Fucked with his legs over my shoulders. Fucked as I held his ankles.
At one point I put his hands on the D rings that attach the sling to the chains. “I normally attach the leather wrists cuff here so you are helpless”, I told him. He held onto the rings and didn’t let go as I pounded him. As intended he was clearly imagining what it would be like to fucked while leathered up.
My favorite position was when I gripped his forearms – one in each hand as he in turn grabbed my forearms. Our arms locked together I started pounding him. The connection of our arms just emphasized the power of the thrusts into his ass – and the grip of his fingers on my arm gave us another way to communicate without words as he moaned.
It was obvious his ass was wearing out. We finished with my favorite – pulling my cock all the way out with each stroke and slamming it back in. I did this for ten, twenty, thirty strokes – every thrust a complete withdrawal and entry thrust into his open teenage hole. Every withdrawal making his ass feel empty. Every thrust being felt individually. With the last stroke I pushed it in as far as it could go and held it – my cock buried as deep as possible before slowly, ever so slowly, pulling it out until his ass was empty. I pulled off the condom and shot it at his ass like a rubber band with a smile on my face. He grinned and pashed Dave some more.
Sex often feels longer than it does. I has been in his ass for more than half an hour – doesn’t sound like much but that was constant fucking. He rolled out of the sling and onto the bed. We realized how late it was getting and he said he had to get back to his hotel – easier said than done when Dave was lying on top of him. Protesting through Dave’s kisses he didn’t seem too disturbed.
The talk turned to musicals and sex – which it turned out were passions of all three of us. I taunted him with my upcoming trip to New York. “I want your life” he moaned – “it’s the same as your life, just a few decades ahead” I reassured him.
“you guys are cool” he said. Which for those who know me is probably the strangest thing I’ve ever been accused of. Adorkable, yes. Cool, never.
There was more making out and more snuggling.
Perhaps the most surprising thing was that no one came. Three horny guys, including an eighteen year old, and no one wanted to break the mood and end the session. In the end he had to go. He dressed, we kissed and he left. A couple of SMS on the way to the hotel thanking us for a great night and that was it.
I messaged him a few days later. No response. That made me sad.
I think one of the reasons it will stick in my mind as a great session is that it was spontaneous, passionate and incredibly hot with a boy who was pretty close to perfection. But he was also nice and clearly a decent guy. It made for a wonderful night but also makes the memory bitter sweet that I probably won’t see him again…..but you never know.