I closed my eyes and began to imagine that he was a woman, touching me so erotically, but soon his voice floated into my thoughts, breaking the façade. “We’re both in here… for life…” he repeated. “I’m so lonely…” he whispered, and now I felt him push me over onto my back, his huge form climbing on top of me, his lips meeting mine. As his tongue probed into my mouth, I relented to his desire, so lost in my own thoughts now that I could barely notice what he was doing to my body. I could feel his crotch grinding against mine, and his rod was bulging, easily bigger than my own cock, and fully erect. His hand released my cock then and reached up to the top of my pants, slowly pulling the material down, freeing my genitals. He pulled his face away from mine so that he could continue to push them down, laying his lips now against my chest. After he had pulled my pants down to my knees, his hands glided back up the inside of my thighs, rubbing against my balls briefly before moving underneath me. I could feel one of his fingers pressing against my anus, and the feeling made me gasp.
“It… hurts a lot the first time.” He whispered, slowly pushing his finger into my virgin hole. “But you get used to it.” He finished, his voice full of sympathy, and yet his hands continued to move. I gave another gasp as my asshole began to give way to his finger, the digit slipping further into me gradually. He now took hold of each of my legs in turn with his free hand, placing them onto his shoulders as his finger began to plunge slowly in and out of my ass. As he slipped the second finger into my hole, his lips closed around my cock-head, and I gave another gasp of pleasure, despite the pain in my arse.
My cock was fully erect by this point, and he wasted no time in swallowing my entire length. He was perhaps the best cock-sucker I had ever had, his lips and tongue working in perfect synchrony as he worked my cock, and I knew straight away that I wasn’t his first, nor his second: here was a man who was experienced. He was so good, in fact, that I had forgotten about the pain in my rear, and soon enough he brought me to orgasm: my cock twitched and exploded, but he made no attempt to withdraw, simply sucking down all of my seed. Once I had finished, he licked my limp cock clean, and then pulled both his head and his fingers away from my erogenous zones.
“I’m going to put it in now.” He whispered, but I was past the point of recognition: lost in multiple emotions and feelings, my body simply sagged down as he positioned his cock at my entrance. He pressed the head against my puckered hole for a moment, before slowly plunging in. Both the pain and the pleasure I felt was indescribable, as his cock pushed further into me, slowly at first, but gathering intensity, until he was pounding into my ass with some force. I let out a moan of pleasure each time he pushed all the way in, and as my moans came closer and closer to one another, he, too, began to make excited noises as I felt his cock bulge in my ass.
And then, without warning, his cock exploded, several shots of semen filling my hole. It was the strangest sensation I had ever felt, but not entirely unpleasant, and as his cock withdrew from me, I felt almost incomplete.
I felt his lips against my chest again, and then on my lips, and I could taste my own cum on his lips and tongue, but the feeling drove me crazy. Reaching up, I placed a hand on the back of his head and forced him deeper into my mouth, sucking on his tongue with all my force, trying to taste my own juices. Once I had sucked him dry, I released his head and he pulled back, before kissing me one last time, gently on the lips.
“It won’t hurt as much… next time.” He whispered.
I couldn’t think of anything to say, lost in euphoria and an indescribable emptiness.
