Gary procured some drinks and Tim sipped his as he continued to sit in stunned silence. Eventually, he figured he should do something other than...gawk at Gary's dick.
"Like....what the fuck...how did you know it was me?"
"Easy. I saw you milling around the building and knew you weren't enrolled. I wondered what exactly you were doing, but lucky for me, I noticed that cute little birthmark on the ass of our volunteer. Knew it couldn't be a coincidence. "
Tim took a long swig, his mind racing.
"So...you remembered my ass from senior year in the locker room?" He asked, incredulously.
"Hell yeah. I used to perv out looking at it. Would have to hang back and rub one out many times. Surprised you never noticed. "
Tim's jaw dropped as he struggled with feelings of flattery and disgust.
"So, you're gay?"
"Naaaah. Listen, I fucking love sex. Even back then, it was easy for me to get girls. But seeing your girly tight ass awakened a hunger in me. It seemed like a challenge. The thought of taking a straight dude and just getting in his head, get him questioning his straightness, and then convincing him to take me in their mouth and ass. Nothing beats it."
Tim gulped, keeping a cautious eye on Gary's cock and feeling his own beef up.
"So...you've done that?"
"Six dudes now. First guy...was the summer after we graduated. This 22 year old guy in the gym shower, could not keep his eyes off my junk. Over time, I started fucking with him. I made sure I was always there when he was. I'd make sure to get the shower head closest to him. Finally, people would leave and I'd make a big show of soaping up my dick, knowing he was staring. You know, if was like I could feel his...bitch factor...or whatever radiating from him. "
Gary took a swig of his drink and continued.
"So, I made sure no one was coming and I walked over, grabbed his hand, and wrapped it around my shaft. He looked at me with shock, his little dick rock hard in excitement. I let him stroke me for a few and then told him to meet me in the parking lot. First thing he tells me is that his girlfriend is out of town. Ten minutes later, he's gagging on my cock while I sit on his couch. Imagine! He has four years on me and he's treating me like a god. A week later, I fucked him hard on the bed he sleeps with her in. Fucking unreal. Even got him to dress in her clothes. There was literally nothing he wouldn't do after that."
Gary beamed with pride and sexual dominance as he told the story.
"Anyway, definitely getting the same vibes from you" Gary added as he pulled Tim's hand onto his cock.
"Gary, I...I dunno about this." Tim meekly protested despite being totality in awe.
Gary had removed his hand and Tim nevertheless continued to grip and squeeze the cock. Gary wasn't going to force it now. He wanted Tim to give himself over and knew he would.
He slid in closer to Tim and put his hand on Tim's ass, slightly squeezing it. With his other hand, he casted some video to the TV. First up was Tim being fingered with the vids Tim filmed himself following. Tim thoughtlessly picked up the pace on stroking Gary while the video played.
Gary slid his hand down the back of Tim's pants and quickly found Tim's still lubed hole. He slid a finger in easily and started fingering him slowly.
"Unnnngh...mmph" Tim couldn't help himself. He knew he could stop and leave at any time, but it felt so good.
"Let's get these pants off, baby. I'll make you feel good" Gary whispered into Tim's ear.
Tim didn't want to voice his approval, but nevertheless lifted his hips as Gary pulled his pants and boxers down.
"Nice, Tim. That's it." He whispered as he put Tim's head in his lap and put two fingers in his hole.
Tim was now face to face with Gary's monster cock in all its glory. He kept stroking slowly as he stifled his moans as Gary found his button and applied more pressure.
Gary kept it going for about five minutes before he sensed it was time for the next step. He pointed the tip of his cock at Tim's mouth, went ham on his prostate, and slid his cockhead into Tim's mouth when he moaned. He kept the finger fucking on full blast while Tim tentatively froze up.
Tim was in pleasure heaven. He wasn't an idiot. He knew Gary wanted a blowjob. Part of Tim wanted to give him one, but he wasn't going to make the first move. He sighed in horny desperation...paused...and started licking and sucking.
"That's it, baby. Flick your tongue around the head...mmm..yeah, just like that, baby."
Tim felt his cock become fully erect. He was out of his mind with horniness and liked the praise. He liked that he was doing a good job. Even more, he liked Gary's fingers inside of him.
Gary let Tim suck away. Tim wasn't good at it all yet, but Gary knew that would come later. Besides, Tim's mouth wasn't the real prize. He accelerated the fingering, going deep as possible and moving in and out quickly. He could feel Tim's breath rate increase as he moaned into Gary's cock.
He pulled Tim's head off his rod and got on the ground with him. He bent Tim over so his torso was on the couch and his ass was facing Gary's cock. Knowing this was a big moment in turning a dude, he lightly caressed Tim's body to calm him.
"You're so fucking sexy, Tim. I mean, your ass. I've wanted it for so long." He moaned as he spread and massaged Tim's cheeks.
"I...I dunno...Gary.....its too big...I don't know if it will work...it's.."
Gary grinned as be lubed up his cock, noting that Tim was concerned about the size and not rejecting having a dick in his ass entirely.
"Listen, Tim. The last thing I want to do is hurt you. I want to do this with you a lot. Every guy I've banged has had the same reservations. But you know what? They all love it. They keep coming back." Gary said as he nestled his cock at the entrance of Tim's hole.
"This is what we'll do. My dick is lined up. I'll stand still. You can back up on it, take as much as you can, get used to it. I'll only start jamming it in there when you're ready. When you are, hit me with two words...'fuck me' and I'll blast your ass like I know you want it."
Tim sighed. His cock was still rock hard. He was tipsy, but knew he'd willingly do this even if he wasn't. Was he gay? Bi? All he knew was that this was the most excited for sex he had EVER been.
Taking a deep breath, he slowly backed his ass back.
"Unngh oh shit" he wailed as it easily pierced through and stretched his ring.
"Just take it slow, baby. You're doing great" Gary said as he spread Tim's cheeks.
At around four inches in, Tim slowed and stopped, allowing himself to get used to it.
"Slide off until it's almost out and then go down again. Trust me, you'll fucking love it."
Tim obeyed, being careful to not let it fall out. He slid back and moaned hard as he was filled again, this time taking five meaty inches. He could hear Gary starting to breath harder and loved it. His tried the steps he took during the exam, pushing out and all, but it was so big.
"Better than my fingers, huh?" Gary said as be gave Tim's ass a slap and squeezed more lube onto his cock.
