Since our initial encounter I've hooked up with the Bear Cub twice more. It's been hot, but our sessions have focused on me making him feel good and pushing all his buttons, while he's been the bottom. Trust me, I am not complaining. I have enjoyed every bit of our sessions.
He's a very passionate kisser, which I fully like, and he can continue with no urgency to proceed south. Actually it takes some steering to lead him from standing and making out to the bed (although he's typically on his knees during part of our "standing." ) The other day was I was struck by how once we get in his bedroom his geeky small talk ceases as he removes his glasses and strips, and then he's all business with little chatter.
When we really get into it, he's commenced with lengthy devotion to my cock, giving me oral. He definitely wants to please me, but it's clear he loves my cock and views being able to throat it as a sport. While definitely nice, its not getting me off (he doesn't recognize the need to simultaneously stroke while sucking) but besides enjoying the touch, and his effort to make me feel good, I realize I need to lay back and be patient as this is also part of getting him off.
As typical in such encounters, getting oral is usually followed by repeated passionate kissing with me then going down. I do work his cock (although it's pretty small) with both my mouth and hand simultaneously. Feeling him get even harder, his sighs and his change in breathing I can tell when he's about to cum and know to pull off (interesting as when we first connected he indicated he doesn't usually cum due to his allergy meds.) Then it's to his balls and his taint and down to his anus. But then it's time for more mouth to mouth tongue exploration (both for passion and to prove to each other that if someone eats your ass you need to be willing to kiss them afterwards.) Then it's time for him to roll over and for me to pull his cheeks apart and give him a serious rim job.
This past time that we connected we began with him on his knees sucking me with his ass over my face so I could work his hole with my tongue. I was definitely into it as I could hear him continually gasping and gradually loosening so that I could penetrate him with my tongue. Midway he abandoned giving me oral and allowed me to service him. And then it was time to get him to roll over and for me to pull his cheeks apart and to get him seriously wet.
I was struck by how good the musk from his ass was; he was clearly cleaned out (the minute I smell any fecal odor it's over...) The aroma makes you "dive in" and keep going back for more. His cooing and moaning was the primary incentive, however, and made me determined to keep at it until my tongue needed a rest.
Following rimming I usually like to lie back with the guy and make out some more; good sex (for me) is about being leisurely and savoring each part of the experience -- otherwise it gets mechanical.
This time he crouched over me to insert my cock into himself; he gave it a good effort with just spit, but being super tight he needed to grab some lube to slicken up me and to wet himself. And then after the initial entry he eased down onto it bit by bit. His face was a mixture of pleasure and grimace; he indicated it had been since our last encounter for him to get fucked. He rode up and down on my cock, but I always get nervous as I know two guys who have had their cocks severely injured (and been unable to use them) as a result of a bottom riding them. So, while I really wanted him to both loosen up and to enjoy it, I was carefully monitoring that he leaned toward and not away from me. Now I want to be clear that I too was mostly seriously enjoying how it felt.
He dismounted and then we alternated between him on his side (where I got past the curve in his intestines known as the "second hole") and him laying flat. Each guy is configured a bit differently (as you learn trying to enter him) and I find while the side position is my favorite, to stay in required him leaning away from me, and I really get into fucking when I can hug the guy to my chest to move back and forth in him.) I was definitely enjoying the feeling of my cock head against the walls of his ass, and loosening him up further as I pushed into him from different positions. The best part -- and the greatest incentive was listening him moan in pleasure saying "oh fuck, oh fuck, oh Fuck!" We were at it a long time, but unfortunately he doesn't seem to remember to fuck back against me and I wasn't getting the sensation in the head of my cock needed to cum, so I eased out and we proceeded to make out some more and intensely stroked each other's cocks. I was starting to feel really good and could tell I'd likely get eventually there, but I felt him start to get severely hard and his balls were tight so I knew he was ready. He then grabbed his own cock and started to furiously stroke and I crouched down and waited; his face was tight, his eyes steely, and his breathing heavy as he began to spurt. An initial stream hit his stomach but I immediately put my mouth over his cock head and took the rest of his load, licked up what was on his stomach, and pulled up to kiss him. He was initially hesitant but then let go and got into it. Years ago I had a bottom who shared he loved everyone else's cum but his own, so I got the initial reluctance.
We continued making out, but I could tell the moment for me to possibly cum had passed. I absolutely cannot cum on demand, and as I get older I realize just to cum isn't what good sex is about. It's the feeling, the touch, the tasting, the aroma, and the experiencing the joy of being with another man and getting him off. I didn't cum the last two times after having bred him during our initial hook up, but that was okay. I clearly had a fine time and got my fix of human touch.
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