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Terry's First Time

A young guy has his first experience with another man he met online.
Terry walked up the sidewalk toward the two story house. He double-checked the number he had scrawled on the scrap of notebook paper he now clutched in his hand, verifying that it matched the house number. He stood just in front of the bottom step leading up onto the porch. His heart beat rapidly. The door of the house swung open and a man who appeared to be in his late twenties and clad in black basketball shorts and a white t-shirt stepped out onto the porch. “Hey there, Terry. Did you have trouble finding the place?” the man called to the twenty three year old, who still fidgeted on the sidewalk.

Terry smiled a bit, happy to at least see that Greg, the man he had been talking to for the last few weeks, really looked like the pictures in his profile. “No, not really. I just took my time. You know, verifying everything.”

“Yes, you strike me as the cautious type. That’s a good thing, really.” Greg gestured toward the wicker chair that sat on the porch to the far left of the front door, then leaned back against the railing on the right side of the porch while facing the offered seat.

Terry smiled and stepped up onto the porch and walked over to the chair. He paused and noted that his host made no attempt to close the distance between the two of them, then sat. He thought for a moment before speaking. “I’m a bit surprised you invited me to sit out here.”

“You mean instead of ushering you right into my bedroom?”

“Well, yeah. I mean, that’s what you invited me over for, right?”

Greg shrugged. The gesture struck Terry as surprisingly nonchalant. “I invited you over to see how things developed. That’s the same reason I’ve been chatting with you online since I first sent you a message. Besides, you seem extremely nervous. That’s not surprising, since you’re totally inexperienced. I’d rather put you at ease first if we’re going to actually have sex. It’ll be far more enjoyable for both of us that way.”

Terry grinned. “Thanks. Seems like a lot of work for you. I mean, why do you bother?”

“Well, in your case, because you’re extremely good looking. But then, I just enjoy giving guys their first experience. There’s something sweet and arousing about watching a guy slowly realize how wonderful sex with another guy can feel. I enjoy watching that last bit of nervousness turn into a mix of bliss and desire.”

Terry could feel his own curiosity and interest stirring as he listened to the older man. He tried to imagine the delights that Greg was describing, and his manhood also began to stir. Greg chuckled and nodded toward Terry’s crotch. “I see you’re certainly curious, despite the nervousness.”

Terry chuckled and shifted in the chair a bit, trying to make the sudden tightness in his khaki shorts more comfortable. “Yeah. I mean, I’ve watched videos online and stuff and it looks incredible. And you make it sound fantastic. So yeah, I guess I really want to find out for myself.” He stood and walked toward Greg. The older man waited for him to get close enough, then reached out a hand and gently guided him closer. The pair now stood together with Greg’s hand partway around Terry’s waist.

Greg took his other hand and traced along the younger man’s jawline with his thumb. “You sure?” Before Terry could answer, Greg pressed his lips to the younger man’s and initiated a soft, sensual kiss. Terry tensed for just a moment, then relaxed into the experience, pulling at the older man’s lips with his own. Greg ran his hand up under the virgin’s shirt and caressed his abdomen and chest and Terry could feel his body respond with increasing desire. He practically moaned when the hand around his waist began to knead his butt cheek.

Greg broke their kiss and smiled. “Yes, I think you’re ready. He turned the younger man around and led him into the house and small bedroom on the first floor. Terry stared at the bed, noting the lubricants and condoms carefully laid out on the table next to it. “I guess you have everything set, huh?”

“I like to be prepared, just in case. But like I said, you’re free to stop whenever you want. No pressure.”

“No, I’m liking this so far. I was just taken by surprise. Kinda like I can’t believe it’s gone so far.”

Greg stood behind him and placed his arms around his waist while kissing the younger man’s neck. “Yeah, I know what you mean,” he practically purred. Tyler could feel the other man’s stiffening rub against his tailbone. It filled him with a moment’s nervousness, but was quickly replaced by the pleasure of Greg’s assault on his neck. He soon felt the other man’s hands fumbling with his belt buckle and closed his eyes. Soon, his shorts fell to the floor and he felt nothing but air caressing his privates.

“No underwear?” Greg whispered in his ear.

“No, I decided not to wear any.”

“How naughty,” Greg said as he wrapped his hand around Terry’s member. Terry gasped as the first person besides himself began to slowly pump his shaft. He pushed back against Greg, practically trying to melt into his body. “Take off your shirt,” Greg whispered and Terry complied, grabbing the tee at the waist and pulling it over his head.

Once Terry was completely naked, Greg gently pushed him toward the bed. Terry landed on it and immediately rolled over. He watched as his first lover began to undress himself, exposing a hairy, yet well defined chest. As he pulled down his boxers, a thick, nearly erect penis emerged along with two perfectly shaped, low-hanging balls. Terry’s gaze was transfixed.

Greg joined Terry on the bed and moved his lips to the younger man’s right nipple. Terry gasped as lips and teeth alike were used to bring his nipple to full attention. Terry was hard as a rock as the other man continued to stroke his shaft slowly, keeping him stimulated without pushing him over the edge. The younger man kept moaning, unconsciously thrusting his hips.

Greg pulled his mouth off the throbbing shaft and stroked it slowly with his hand. He gently lifted Terry’s balls with his other hand and began to lick underneath them. Bit by bit, his tongue edged back to the virgin’s crack. Terry moaned and instinctively pulled his knees toward his chest, exposing more of his ass. Greg removed his hand from Terry’s cock and used both hands to spread his cheeks. Greg’s tongue quickly found and began to swirl about the ring of muscle it was seeking, causing Terry to moan. The younger man began to stroke his own cock. “Not too fast,” Greg cautioned. “We’ve a lot more to do...unless you want to stop, of course.”

“God no,” Terry responded in a raspy voice. “Though I’m not sure how much longer I can hold back."

“Well, try your best,” Greg said, then skillfully began to push inside of Terry with his tongue. Terry gasped as Greg began to probe his innermost depths.

After a minute or two, Greg spoke again. “Hand me that bottle of Boy Butter that’s on the night stand.” Terry did and watched as Greg squirted some of its contents onto his index finger and coated it. He moaned as Greg then gently pressed the finger inside of him, the creamy texture of the lube easing the entry. With a bit of time, Greg had the finger deep inside the young man and was moving it all around. Terry felt like his insides were electrified. He was leaking precum and stopped stroking his shaft, for fear he’d explode.

“Oh God, please tell me you’re going to fuck me soon.”

Greg looked into his eyes and smiled. “If that’s what you want.”

Terry glanced at the night table and plucked a wrapped condom off of it. He tossed it to Greg, hoping that would be answer enough. The older man quickly unwrapped the condom and rolled it onto his own thick, hard member, then applied more of the creamy lube to it. He then rolled Terry onto his side and lay behind him. Terry could feel the man’s cockhead against his sphincter as the Greg lined himself up. He then felt an slowly increasing pressure. After a few seconds, the pressure was great enough that the virgin’s anal ring began to give way. Terry moaned as penetration began.

Greg was slow and tender about the process, massaging Terry’s chest and shoulders as he pushed deeper inside the young man. Every now and then, he’d pull back out a tiny bit, giving Terry’s anal walls a chance to relax before he began to push in. All through it, Terry breathed and moaned.

Once Greg was fully inside, he flexed the muscles around his shaft, causing his erection to shift inside his partner. Terry shivered each time. Once Greg was sure Terry was relaxed, he began a slow pistoning motion. Every few strokes, he’d change his angle just a bit. Terry moaned as his insides were massaged and more fully opened in the process.

After a bit, Greg hit the perfect angle and his head grazed the virgin’s prostate as he pushed in. Terry’s whole body spasmed as the most intense jolt of pleasure struck him. Greg once again wrapped his hand around his partner’s shaft and began to stroke it in time to own thrusts. Terry just moaned, unable to do or say anything else through the pleasure.

It took only few more seconds before Terry exploded. He grunted and moaned as his orgasm hit, his seed shooting all over the bed. He could feel his anal muscles spasming around Greg’s shaft, which continued to move in and out of him. About halfway through his orgasm, the older man pushed fully inside of him and ground his pubic bone into Terry’s ass. The pair lay there.

After a minute or two, Greg whispered in Terry’s ear, “So was it everything you had hoped for.”

“And then some. I don’t think I’ve ever cum like that before. How about you?”

“Your tight ass was all I needed. I’m just hoping the condom didn’t break.” Terry glanced back at Greg, a look of fright filling his eyes. “Just kidding. But I best pull out.” He did, and Terry sighed, almost regretting the sense of emptiness that he now felt. He saw Greg reach between his own legs, then hold up the used condom, the end full of his seed. “See? Everything’s fine.”

“Good. Thank you for that. I needed it.”

“I enjoyed it. I’m glad you did too.”

“So,” Terry said, somewhat hesitantly, “do you mind if I stick around for a bit.”

“Not at all.” With that, Greg wrapped his arms around the younger man and they lay there spooning. Terry sighed contentedly, glad he hadn’t chickened out.

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