He had seen many cocks on a screen and sneaked many looks over the years but this was the first real life one he had seen being manipulated for his viewing.
“Do you want to touch me boy?” the man said trying to smile at Greg.
Greg nodded dumbly and reached out taking a cock other than his own in his hand for the first time in his life. It felt so hard, yet so smooth as he started to slowly work the shaft feeling it grow in his hand. As the man’s cock became hard Greg knew it was larger than his own and at least the size of his dildo if not bigger.
“Name’s Lenny by the way,” said the man.
Greg managed to croak his own name in reply.
“This your first time?” Lenny said as he watched the tentative way in which Greg handled his cock. When Greg nodded he removed Greg’s hand and tucked his cock away. “Think we should go to my room, don’t you?”
Greg tucked his own hard cock into his pants, before following Lenny to the elevators. They traveled upwards in silence ignoring both other occupants and each other. Greg’s heart was beating fast as his brain screamed that he was finally going to fulfil his dream.
Once inside the room Lenny turned to Greg and looked him in the eyes.
“What have you done before?”
Greg explained how he had looked but never touched. He talked about chatting and performing online and when he mentioned using a dildo Lenny’s eyes lit up.
“And what do you want to do?”
“Everything,” Greg breathed.
Lenny slowly removed his clothes, his eyes locked on Greg’s as he revealed his hairy chest that was still well muscled before removing his jeans, his cock springing free. Greg reached out to touch it again but Lenny held up his hand,
“Take off your clothes.”
Greg quickly responded removing his clothes with haste. He knew he wasn’t anything like in the same shape as Lenny but apart from a slight paunch he was in reasonable shape.
“Not bad,” Lenny said, “I do like a nice furry ass. Have you ever sucked a cock before?” Greg shook his head, “let me show you how it should be done.”
Lenny knelt before Greg and took his semi-hard cock into his warm mouth bringing it quickly to full hardness. At the same time he reached between Greg’s legs and began to probe with his large digit.
Greg breathed deeply as the finger slipped in and he felt Lenny slowly start to finger fuck him.
Breaking from his sucking Lenny said, “You are tight and guess you have never been rimmed.”
Pushing Greg onto the bed Lenny positioned him on all fours before pulling his ass cheeks apart and licking at Greg’s anal opening.
Greg had seen rimming on screen many times but nothing could had prepared him for the sensations that ran through him. It was like warm gel was being spread around his ass as Lenny’s tongue poked and probed deeper. At the same time Lenny’s large hand was caressing his rock hard cock and full balls.
“Fuck me please. I beg you,” Greg groaned.
“You are about ready,” Lenny said, “but your first time should be on your back. I want to look into your eyes as you take a cock for the first time.”
Lenny pulled Greg to the edge of the bed so he was still standing on the floor. Then he lifted Greg’s legs until they were on his shoulders before reaching under and placing his cock at Greg’s hole. He started to push feeling the tight resistance of an anal virgin, “push like you are trying to have a dump.” His words were rewarded a moment later when he felt the head pop in and clamped tightly.
Greg had white lights exploding in his brain as he felt Lenny’s cock penetrate him. He was grateful that Lenny had paused for a few moments to let him adjust which he was trying to do. The cock was definitely bigger than his dildo and he could feel the increasing pressure as it slipped deeper.
“Does that feel good boy?”
Greg groaned with pleasure as a real cock felt so much better that he had ever imagined.
“I asked you a question,” Lenny said stopping his cock from going deeper.
“Fuck… yes… it feels so fucking good…Oh MY GOD.”
Greg screamed out the last words as Lenny drove his cock fully home leaving it buried to the hilt. With his balls resting on Greg’s ass Lenny reached down and started to work Greg’s rock hard cock.
Greg could feel Lenny throbbing inside him as he whimpered and moaned in pleasure. As Lenny start to slowly fuck him Greg could feel the sensations rushing through him in waves.
“Oh yes fuck my man pussy,” he groaned as he clawed at Lenny’s back and ass urging him back in every time he pulled out.
“Gonna breed you boy… you want my cream in your man pussy?”
Lenny strokes were measured and not too deep or shallow as he drove in and out, three inches was the perfect length of a stroke. He had broken in more than one virgin and although he wanted to pound the fuck out of this married ass gripping his cock, he knew he had to take it steady the first time.
“Oh yes, breed me…fill me with your cream,” Greg moaned.
Lenny’s meaty paw on his cock and Lenny’s own cock buried deep in his ass sent him over the top and he spurted into the air, splattering on his chest. The sight of Greg cumming and the reflex spasming of his sphincter sent Lenny beyond the point of no return. He growled like an angry bear as he pumped his cum deep into Greg’s bowels.
Letting Greg’s legs fall free he collapsed onto Greg’s chest, the cum from earlier matting in his chest hair. He knew that most straights while happy to suck cock or get fucked didn’t go in for kissing. He placed his mouth close to Greg’s ear as he said, “Now that you are no longer a virgin, as soon as I recover I am going to fuck you hard.”
Greg murmured in pleasure as he felt his ass throb as Lenny slipped out. Greg lay on the bed luxuriating in the knowledge that the real thing was as every good as he had hoped it would be. Lenny had returned from the bathroom and Greg could see he had attached a cock ring to his semi hard cock.
“Are you ready to be fucked boy?” Lenny said as he flicked Greg over onto his belly before pulling him onto all fours. Lenny’s cock was throbbing as he ran the head of his cock over Greg’s asshole collecting his previous load. Positioning his cock ready, he grabbed both of Greg’s hips as he pulled him onto his cock as he thrust forward.
This time there was no gentleness, with his previous load serving as lube Lenny was able to drive his full length fully home in one swift stroke. Greg let out a deep groan of pleasure tinged with pain as he felt himself being opened. Lenny pulled back until just the head was inside then fully drove home making Greg groan again. Lenny increased the pace fucking Greg hard and fast, giving him the full length of his cock each time.
Greg was in heaven. If the previous fuck, his first, was good, this was mind blowing. All he could do was brace against the bed, his fingers gripping the sheets as Lenny pounded his ass relentlessly.
“Oh yes daddy,” Greg moaned, all the words he had said online tumbling though his brain and out of his mouth. “Fuck my married man cunt,” and, “use my hairy hole.” He even moaned, “I was born to be a bottom slut for your seed.”