Changing the Rules of the Happiness Game
Copyright© 2022 by NotReallyAshamed
Chapter 12
Romantic Sex Story: Chapter 12 - What's the secret to happiness? Rob thinks he's found it when his sister snuggles up to him, but as time passes the rules of the game keep changing out from under him. And his relationship with his best friend and his friend's mother is confusing, to say the least.
Caution: This Romantic Sex Story contains strong sexual content, including Mult Teenagers Consensual Romantic Gay BiSexual Heterosexual Fiction Incest Brother Sister Masturbation Oral Sex Petting Small Breasts
It was hot in the small bedroom, and when I awoke to gray, indeterminate day light, Timothy had pushed the comforter almost completely off himself; his half was bunched down by his calves. He lay on his back, his chest gently rising and falling. It was only a little past 5 in the morning, according to the LED clock radio on the desk.
I stared at his naked body. The expression on his face was peaceful; his dark hair was tousled and a little damp. He looked soft and inviting. I looked down at his penis, soft, resting in its sparsely-haired nest atop a small, tight scrotum. I could feel my own stir, remembering how he had felt hard and rubbing up against my groin. His breasts — that wasn’t really the right word, they were really just slight swellings commensurate with his overall chubbiness, especially when he lay flat on his back like this — reminded me again of Lily’s, the way they had been about a year earlier.
I remembered that that was the image that had sent me over the edge the night before, and hardened fully at the thought. I wondered if Timothy would like it if I kissed him there, if I took a nipple into my mouth and played my tongue over it. It had driven Lily wild. I had a crazy impulse to try but thought better of it. Not while he’s sleeping, no one would want to wake up to that. Instead I casually put my hand on his belly, as if it had landed there by accident in the night, and closed my eyes, lightly stroking his skin.
I was tremendously turned on, I realized; I wanted nothing more than for Timothy to wake up and play with me. After a while I scooted a little closer and lightly pressed my erection against the side of his thigh, again feigning moving in my sleep. Timothy mumbled something indistinct and I froze. Then he said: “Hey.” It was a friendly “hey,” not too different from when we greeted each other at school. He knew I was awake.
I opened my eyes and saw his face close, turned towards me, looking into my eyes. “Hey,” I responded. We fell silent. When I felt I couldn’t just lie there frozen and silent any more, I took my hand off his belly, accidentally-on-purpose brushing the tip of his penis, which was still soft. This evoked a slight giggle from Timothy. He surely could feel my hard-on, still touching his thigh; at least he hadn’t commented or moved away.
As if in a dream, I returned my hand to his crotch and cupped his genitals. I could feel him stiffening under my palm. Still looking into his eyes, attentive for any sign that he was unwilling, I encircled his now half-erect shaft and began to stroke. His eyes widened a little but he seemed content with the state of affairs, and hardened fully into my grip. Slowly, as gently and deliberately as I could, I masturbated him, never breaking our mutual gaze. The look I perceived in his eyes was almost one of longing, and it instantly made me feel tender and solicitous towards him. I stroked him almost lovingly, and when he began to tense up and moan softly, I finally broke my gaze and shifted it downward, watching intently as he spurted all over my hand and his belly.
When he had recovered, he reached for my hard-on, but I had a sudden impulse to try something else. I whispered “Wait. Turn on your side -” and nudged him a little to indicate that he was to face away from me. He did so without hesitation. I pulled him into my arms, positioning my erection between his butt cheeks, and my hands on his chest. I was shaking with unfamiliar excitement.
With my eyes closed, caressing Timothy’s almost-breasts, with his ample butt cradling my penis, I could almost imagine I was reprising the same position I’d been in with Lily, not so long ago. I envisioned her lying in my arms, and soon I was thrusting back and forth, teetering on the edge of orgasm. I heard Timothy whisper something under his breath, but I couldn’t make it out. I put my hand down to his crotch but he was soft. It felt even smaller than it had looked when he was sleeping. His scrotum was still tightly scrunched up, and I could still feel the wetness from his earlier ejaculation under my hand.
Half of me, feeling his pliant breast under my left hand, was imagining Lily; the other half, as I caressed his soft genitals, was reveling in getting so intimate so easily with a good friend. He was still saying something, so low that was almost as if he didn’t want me to hear. On impulse, not even sure I knew why I was doing it, I kissed the top of his head, tasting the sweat on his damp hair.
Now I could make out what he was repeating in such a low murmur: “Rooobbb ... Roobbbb...” I kissed his hair again and touched his thighs, his belly, his face, then finally his genitals again; when my hand found its way back down there I could feel that he was semi-hard again, and the knowledge that I was turning him on even so soon after he’d come, that I could make his little penis stiffen, that he was murmuring my name, that he was letting me touch him all over, all that finally did the job: I came, hard, ejaculating all over his backside.
We lay like that for a while, wordlessly, and I kept caressing his penis. After a few minutes, I was rewarded as it stiffened again, much to my surprise: I’d never been able to get hard again so soon after an orgasm. For me, coming always put me in a mental state where I longed for physical, skin-to-skin contact, but didn’t need or want sexual stimulation. Nevertheless, I was feeling an intoxicating rush now; not so much sexual arousal as excitement that Timothy was evidently putty in my hands: I sensed that he would let me do whatever I wanted to him, with him. That look in his eyes when I’d first reached out to masturbate him this morning...
I was getting hot and sweaty pressed against his backside. I backed away a little, continuing to stroke his erect penis. With my left hand, I pulled him over onto his back again. Slowly, never taking my hand off his penis, I lifted myself up on my knees and positioned myself at his feet. Then I put my face down near his crotch, looking up at his genitals from below. His scent was intoxicating: a mix of semen, sweat, and the characteristic, sour-but-not-unpleasant genital odor I knew from the time I had examined Lily’s vulva up close.
Tentatively, still stroking his penis with my hand, I took a lick at his scrotum, feeling the ridge at the bottom with the tip of my tongue. Timothy groaned loudly. I began to lick more deliberately, tasting the saltiness. Then I put my lips around the head of his penis. The salt taste was replaced with the odd, slightly soapy flavor of semen (I had tasted my own of course and knew what it was like), left over from his recent ejaculation, and perhaps a small amount of fresh precum. I teased it with my tongue, enjoying his irregular moans and the way he was now squirming around.
Finally, I took his entire hard-on into my mouth - it was that small - and simply tongued, tasted, and sucked, as Timothy groaned, shook, and finally, after a few minutes — with a loud sigh — ejaculated a small amount of semen into my mouth. It tasted nice, and I swallowed it, then sat up and smiled at him. He was looking at me with a slightly embarrassed expression, so I said, earnestly, to put him at ease: “That was nice, Timothy.”
He closed his eyes and didn’t reply. On impulse, I stroked his hair. He shivered, and said “Rob...” “What?” He didn’t answer. “Let’s get up,” I said. “Maybe we can get breakfast at the Ambrosia before first period.” The Ambrosia was the coffee shop near school where we often had lunch. I’d never had breakfast there but it seemed like a natural thing to do at a coffee shop.
As it turned out, we didn’t have to eat breakfast out. Timothy pulled on his underwear and went to the bathroom to take a shower. When he came back to the room, a towel wrapped around his waist, looking fresh, his hair still wet, he said: “Mom is making breakfast for us.” I left the room and was glad I had put on the previous day’s clothes to walk to the bathroom; it was down the hall and in full view of the kitchen area in the small apartment, and Timothy’s mom - Alice, I reminded myself - gave me a cheerful wave.
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