Jon and I were sixteen year old friends staying at my house while our parents attended a conference in a neighboring state. Jon was gay-curious and I was anal erotic, as we learned about each other. That weekend home alone, we tested the limits of boy-on-boy experimentation!
(A fantasy based on my real experiences.)
I fell asleep late Saturday night, after laying there collecting my thoughts about what had happened the night before. Didn't see the time when I awoke, but the world was quiet and a soft morning breeze was teasing the curtain and sliding across my shoulders. A dreamy feeling filled me. The dreamy morning-after feeling that we got as teenagers after a sexy night.
I don't know how much earlier Jon had awakened, but I could sense that he was awake. Maybe he had laid there reliving as I had done before sleeping. He must have been feeling a charge, because as soon as I stirred, he got up and perched himself on the edge of my bed. Through the covers I felt his hand come to rest on the back of my thighs and then inch its way up to my ass and back down almost to my knees. Twenty-four hours earlier I would have cussed and shoved him onto the floor, but now I didn't mind him being there. Still on my stomach, I scooted an inch so he would not fall off the twin bed.
I felt the covers lift a little and his hand on my bare skin...same place. It lingered longer on my ass than on my thighs, as if thighs were just a ramp to what his hand really wanted to touch. When I felt a finger tracing the line of my crack, something inside me stirred. I opened my thighs a little wider and a warm hand invaded my crotch, feeling for my balls and squeezing them gently, then firmly. My penis was fully awake under me now. I could feel my own wetness on the sheet and my belly skin. I am sure my hips were moving. Dead give-away that I was liking it and wanting more. (Until now, I was getting away with pretending to be half asleep.)
Then the sheets were off me and a cool morning breeze touched my back, ass, and thighs. Sensual! That was replaced by the warmth of Jon's lean body covering the whole length of mine. A surge of energy shot through me as his bare, hard dick came to rest on my crack. Not wanting to spoil the moment by thinking, I pressed my butt up against him. We stayed like that for a few tantalizing seconds while he reached under me and felt my dick. (First time anyone but me had touched it, erect.)
Suddenly, Jon got up off me and walked to the bathroom. He came back with the Vaseline and offered me some. I declined, having already pulled my feather pillow under me as I usually did with my morning hard on. He climbed back on the bed, coming to sit straddling my legs. I could feel his ass, thighs, and even his hairy balls against my tender thigh skin. Heard him poke a finger into the jar and begin rubbing the petroleum jelly on his dick. I propped myself up on my elbows so my fingers could touch my nipples while I slid my penis in and out between the pillowcase and sheet, the Same way I did when I started beating off at 13, leaving many a cum stain on the sheets that my mom had to wash.
In my peripheral vision, I saw a finger go into the open jar on my nightstand and come out loaded with Vaseline. Heard myself wondering "How much does a guy need?" My question was answered when I felt his warm finger between my ass cheeks, the greasy tip lubricating all the way up and down my crack. Net yet satisfied, he stuck his finger one more time into the jar and smeared a lot of it right around my hole.
Now I was humping my sheet and pillow with a craving in my stomach for something--ANYTHING--involving his hard dick and my bare bottom. Jon was no doubt looking at my ass and feeling the same heightened excitement of where his penis might go next.
He brought himself more over my middle and his hard on came to rest on my butt again. It felt hotter than before against my ass skin, intensifying the craving in my stomach. He pushed down on it with his fingers and the whole shaft slid in between my buns like a hot dog, his warm balls pressing up against the tops of my thighs. I'll bet he loved the sight of it because he hung there for a bit before sliding it up and down the length of my crack. I am telling you, the sensations of my own dick moving between the pillow and sheet and his hot, stiff one sliding between my buns and grazing my asshole were unbelievable! After every few strokes, he would slide it all the way to the bottom of my crack and push it down between my thighs until I felt the head of it stretching my scrotum and the shaft laying against my crotch. I was craving one thing, and one thing only. Unfortunately, I didn't know if I could live with myself afterwards, and the combination of that and me pushing him away the night before may explain why I didn't ask and he didn't try.
I suppose neither of us wanted to end it by cumming. But finally Jon said, with an almost breathless voice, "I'm almost there. Should I cum on your ass...or not?" "Anywhere you want" slipped out of me as my lust reached its peak. Truth be known, there was a very specific place where I wanted him to cum. I wanted him to cum with it hard against my hole.
Jon read my mind or had the same idea, because I felt the flared head of his penis push between my buns, felt it press against my hole and almost immediately the hot, wet spurts.... one.... two.... three.... UUUUHhhhhhh!! That sent me over the edge. I felt my own cum shooting all over the pillowcase and sheet.
Jon's body collapsed onto mine and we laid there for a long time with his dick growing softer in the crack of my ass. I could feel it still dripping onto my skin. When he got off me, I got up and grabbed a couple of tissues to wipe the mess off my sheets. Jon stood close behind me and his finger found my hole, all covered with his own cum. He pushed the tip of his finger into me, while his other hand reached around to the front and cupped my wet, softening dick and balls. I reached back and put a little pressure on the back of his hand. He took the hint and pushed his finger up me as far as it would go. My breathing still hadn't settled from all the excitement. I remember some heaving breaths and exhales like huge shaky sighs. For the first time, I put my hand on Jon's bare dick. It was soft and limp like mine. Even after my orgasm, the back of me still craved to be filled up and if we could have gotten hard again, I would have carried on from this very place. (Countless times in masturbation I have fantasized about Jon bending me over the chair and fucking me in the ass, right there and then.)
We took separate showers and met in the kitchen for breakfast. Both of us were quiet this morning, all the bravado having gone out of us from the night before. We talked about going to the pool for awhile. That would be a good change. The sexual tension was discharged for now and we could be more-or-less like regular buddies. But being teenagers with the house all to ourselves, there was no doubt in my mind that the tension would build up again. We still had the whole day and a good part of the evening in our safe, private world.