Is That My Underwear?!

"I think I've died and gone to heaven," Jimmie smiled, then noticed Troy's still throbbing erection. "I think it's your turn."

"Wait...I wanna try something. Do you trust me?" Troy asked seriously.

Jimmie stared him straight in the eyes, "Of course."

Troy grasped Jimmie's arms and planted another kiss on his mouth before pulling back.

"Bend over."

Jimmie's eyes widened in surprise with a dash of fear. Sure he had fantasized about having sex with Troy countless times. And most of those times he was bent over or on his back as Troy pounded him like a jackhammer. But now that the opportunity was actually presenting himself, he was a little afraid. Nothing had ever entered his tight hole, least of all anything as big as Troy's manhood.

Troy could sense Jimmie's hesitance, "Don't worry buddy, I won't do anything you're not ready for. Just trust me."

And with those simple words, Jimmie's reservations slipped away. He did trust Troy. So slowly but surely, he turned his back to the older boy and leaned forward placing his palms on the shower wall.

Troy moved to press himself against Jimmie, his burgeoning hard on resting in the groove at the top of Jimmie's ass. Using his hands to gently massage Jimmie's back, Troy bent down and placed soft kisses along the boy's spine. He kissed each vertebrae, moving downward till he got right above Jimmie's crack. At that moment, Troy's tongue eased its way out of his mouth, and he swiped it in between the soft cheeks.

"What are you-" Jimmie began, but was cut off as soon as Troy's tongue grazed over his rosebud. "Oh God, don't stop."

Troy, never one to disappoint, used his hands to spread apart the plump cheeks, exposing Jimmie's hole before diving back in. His tongue worked magic on the tight opening. And just when Troy sensed that Jimmie was relaxed, he pressed one of his fingers against the hole, easing it in to the first knuckle.

Jimmie bucked and grasped the wall for support, his anus clinching around the new intruder.

"Just relax Jimmie, we'll take it slow," Troy cooed.

When he felt the boy's muscles relax slightly, he pushed his finger in further, only to pull it out, and then back in again.

"Is that okay?" Troy asked.

Jimmie groaned, "Yeah...it's different...but okay."

Troy then added a second finger, ever so gently. When Jimmie was okay with that, Troy moved his fingers in a scissoring motion to help stretch his friend out. Two fingers soon became three.

Finally, Jimmie said, "I think I'm ready now."

"Are you sure?" Troy asked, still pumping his fingers in and out.

"Yes. I want you inside me. Now."

Troy didn't need to be told twice. He removed himself from Jimmie's ass and quickly ran to his locker to get a condom and a tiny bottle of lube. When he returned, Jimmie was waiting anxiously, his erection back in full force.

"Let me," Jimmie offered, taking the condom from Troy's hand.

He opened the foil square and pulled out the condom. Grabbing Troy's achingly hard dick, Jimmie gave it a few strokes before easing the condom on. It was a tight fit over Troy's thick member. Jimmie gulped realizing that that thickness would soon be invading him.

Troy lubed up his covered cock and put the remainder on his fingers. He resumed his previous action of stretching out Jimmie's hole, preparing him for a much larger intruder.

"Alright, here it goes. Let me know if you want me to stop," Troy told him.

He lined his purple head up against Jimmie's anus and slowly began pushing it in. Despite all the stretching, it was still a very tight fit, and Jimmie's nervousness was making it harder.

"You've got to relax Rocket Man. I don't want to hurt you."

"Don't worry about it," Jimmie said through gritted teeth. "Just fuck me."

Troy's cock pulsed at Jimmie's command. He continued carefully to ease himself in through the tight channel getting about three inches in before pulling out all but the very tip. Back in again, this time adding another inch.

"Ahhhhhh," Jimmie half moaned, half cried.

"We're halfway there dude, you're doing great."

To try and get Jimmie's mind off the pain, Troy reached around and wrapped his hand around Jimmie's throbbing hard on. He idly stroked it, all the while easing himself further and further into Jimmie's ass. After a few more attempts, Troy's seven inches were fully buried in Jimmie's hole. He just stood there for a moment, allowing his friend to adjust before moving back and forth again.

"How you doing?" Troy asked.

"The pain is almost gone. I think it's---FUCK!"

Troy stopped suddenly for fear that he had hurt Jimmie. He almost pulled out until he felt Jimmie push himself back on his cock. Then he realized...he must have hit Jimmie's G-spot. So he began thrusting again, and sure enough, Jimmie's groaning was nothing but pleasure.

"Jesus Troy...go faster please!"

Troy could follow orders. He gripped onto Jimmie's hip bones and began pistoning away, trying to go deeper with each thrust. The feeling of Jimmie's body wrapped so tightly around his dick was quickly bringing Troy to the edge. Jimmie wasn't far behind, having resorted to jacking himself off as Troy hit his sweet spot over and over again.

"Oh God, I'm gonna cum again, don't stop!" Jimmie cried.

His hand was a blur moving over his cock, and within seconds a stream of cum was shooting out against the shower wall. Jimmie's orgasm made his whole body quake and his muscles contract, which was too much for Troy. The older boy let out a scream as he also unloaded himself, deep within Jimmie's ass. Troy practically collapsed forward onto Jimmie's back. He placed kisses on Jimmie's neck, still encased in his warmth.

"That was the most amazing thing I've ever experienced," Jimmie breathed. "Thank you."

Troy removed himself and turned Jimmie around to kiss him full on the lips.

"No, thank you. That was a first for me too. You were the amazing one."

The two boys shared another kiss before they actually cleaned up under the showers spray. As they headed back to the locker to get dressed, Troy thought he heard the door close, but no one was in sight. Looking around, he noticed something on the floor. He went to pick it up...a hat? It looked oddly familiar...

"...Ryan?"