My next encounter was with a virgin, something I told myself not to do on account of their lack of experience. I didn't want to waste my time breaking in a novice. Luca had other ideas. Luca was about 5'7", only around 85lb, skinny as a rake. Living at home, he was out to his parents, who told him he was not allowed to bring boys home. At 23, it had taken him five long years to pluck up enough courage to put his profile on a hook up site. Even then, it was a very modest profile, his picture showed his svelte like figure in a Jockey Y front and singlet. What did it for me was his ginger hair, china blue eyes and freckles, making him look like a teenager. I thought long and hard about inviting him over. Messages went back and forth, 'Are you sure this is what you want to do?' 'Do you see yourself as a top or bottom? 'What do you think of when you masturbate?' and so on. Each question came back with a positive answer, so I arranged to meet him in a bar, with no promises. It went like a dream. Luca turned on the charm offensive, I could have picked him up, kissed him and crushed him. I gave him my number and invited him to my place Saturday. I thought of inviting him to stay over, but that would have been too forward, besides, if things didn't work out, I would have been stuffed.
He arrived Saturday at 7.30pm, looking very apprehensive. I was smitten. A light coloured hoodie, the hood up framing his face, matching, soft cotton shorts, I could have picked him up and carried him to the lounge. As it was, I could see how nervous he was. I led him through to the lounge, and we sat together on the sofa, with him looking down at the carpet. "Are you sure you want to do this?" He nodded. "Tell me again what goes through your head when you wank?" Luca thought for a long moment, "I don't know really, Sometimes I'm being shafted from behind, I can almost feel the penis inside me. Another time, I'm with an old school friend I had a crush on. We make out and end up fucking, I have my dick in him." I turned his face towards me, a tear in his eye, slightly blushing, very endearing. I leant down and kissed him, no resistance. I kissed him again and our mouths opened, progress. I stroked his thigh, his legs parted. With each stroke I went a little higher, the kissing continued. When I reached his crotch, he was hard, a long erection bending away towards his groin. I took his hand and placed it on my hardness, "Can, can, um, can I see it?" I slipped out of my shorts, taking my boxers with them. "Bloody hell, it's so fat, it will never go inside me." His hand gripped it and instinctively stroked up and down. "Let's get you out of these." I lifted his hoodie off, his ribs were like a xylophone. He lifted his bum, and I removed his shorts, leaving his Y fronts on for the time being, I didn't want to alarm him. A damp spot had appeared at the end of where his dick lay under the cotton. He removed them of his own volition. At well over 6" and uncut, he had nothing to be ashamed of, the bend reaching well across his right groin. Apart from socks, we were both now naked. We kissed and held one another's knobs, a little mutual masturbation. It was too much for him, and he covered my hand with semen. "Sorry, I got over excited, no other person has ever touched my penis." I licked the cum from my hand and told him not to worry, as we had all evening. I carried him upstairs to my bed, where we kissed and cuddled, his erection wasn't returning, even when I gave him head, "Luca, why don't you watch me toss myself this evening, I think you've had enough for now. You can either stay the night, or come back in the morning, when I'll make love to you." He put his head on my chest and I jerked, the first two jets hit him in the face. Back downstairs, he dressed and said he'd be round at 10 in the morning, prepared to go the whole way.
It was a different, more confident Luca next day. Smiling he was up on tip toes, kissing me as soon as the door was shut. We went straight to the bedroom, abandoning our clothes on the way. "I gave myself a good talking to, told myself not to be so foolish. I want you to fuck me, I need this monkey off my shoulder." I kissed my way down his skinny body and swallowed his cock, giving him head, not long enough to make him cum. I guided him down to my pole. He held my balls and licked my shaft. With some encouragement, he sucked me. Onto his tummy, I rimmed his virginal rose bud, he moaned and leaked. Licking a finger, I inserted it and felt for his prostate. There was now a steady flow of precum onto the duvet. "Are you ready?" He nodded. I applied loads of lube to both of us, "This will hurt, I promise you that it'll be worth it." With Luca on all fours, I pushed gently against his ring, "Fuck me, please." I pressed harder and broke through his sphincter, "Jesus fucking Christ." I waited for a long moment, "Okay?" "Yes, yes, it needs to be done." More lube and I pushed on until I was buried inside him, "Wow, bloody awesome." I began to pump, long slow strokes, slowly increasing in pace as his hole accepted me. His moans became louder, as did my grunts. He was wanking with his right hand, shooting a massive load over the bedding. "I'm getting close, do you want me to breed you." "Yes, yes, do it." I unleashed a torrent of cum into his bowels.
We lay beside each other in silence, one of the best shags I'd ever had. Time drifted past. Eventually, Luca said, "Can I try to fuck you later?" They were the words I'd been waiting for, I kissed the answer to him. After a light lunch, we were back in bed, hard and raring to go. Luca was now in control, We kissed, he gave me head, turned me over and rimmed me. Back facing each other, Luca lubed us and mounted me, missionary, he fucked me with all the energy of youth, twerking his pretty ass. Having only cum a couple of hours ago, he fucked me for an age, ensuring that I came before he unloaded inside me. Luca, now a man instead of a boy.
We were to meet several times before he found himself a boyfriend. Sad to lose him, but happy that he was now happy. The last thing I heard of him, his parents were now allowing him to bring his boyfriend home. I liked to think that I had contributed in some way.
