Helping Mom Pay The Rent

Jack rolled onto his side facing Keith. Reaching out, he gently rolled one of Keith's nipples between his fingers, then leaned over kissed Keith again. Keith responded this time, letting Jack's tongue explore the inside of his mouth.

Jack broke the kiss. "That's better," he murmured, looking into Keith's eyes, then pressing his lips against Keith's again.

Against his expectations, Keith was really getting hard again. Jack hand wandered down from Keith's nipple, stroked across his belly, then slowly encircled Keith's dick. Keith let out a slight groan at the touch.

Jack's lips left Keith's, then wandered to Keith's neck. Nuzzling and kissing it brought even louder moans, and Keith's dick throbbed in Jack's stroking hand.

Jack whispered into Keith's ear, "Are you ready to try sucking me?"

Keith pulled back slightly, his faced turned towards Jack's. "I'm not sure," he said.

Jack smiled and replied, "No rush, we have hours. I would definitely love it if you tried it, though. I have a feeling that you'd be really good at it."

Keith blushed. "Will you do me again?" he asked, his voice quivering from his excitement.

Jack smiled and kissed his way down Keith's chest and stomach until his face was even with Keith's crotch. He kissed the tip of Keith's dick, then his tongue came out and licked lazy circles around Keith's cockhead. Keith drew a short explosive breath in.

Jack slowly started working his mouth on and down Keith's dick. Keith threw his head back, and his hands found Jack's head to urge him to take his dick deeper. Jack let Keith guide him, knowing that it would increase Keith's excitement.

Jack slowly and lovingly sucked Keith's dick for another ten minutes. He slowed down when he felt Keith get frantic, and sped up when it felt like Keith needed more. He drove Keith crazy with his mouth.

Just when Keith felt like he couldn't stand any more and desperately needed to cum, Jack pulled his mouth off of Keith's dick.

"I could use a little attention, too," he said, grinning up at Keith. "Want to try sucking me now?"

Keith was ready to burst, but the rough mouth-fucking Warren had given him was still on his mind. "I'm still not ready. Is there anything else I can do for you?" Keith said plaintively.

Jack grinned evilly, then reached around and grabbed Keith's asscheeks. "Well....I could always fuck that tasty little ass of yours," he said.

That actually sounded better to Keith than sucking Jack's cock. The session with Warren wasn't pleasant, and the idea of getting his mouth raped again like that was frightening.

Jack moved back up on the bed, and rolled on his back. "Do you have some kind of lubricant?" he asked.

Keith rolled over and pulled a bottle of lotion from his nightstand. It was what he used when he masturbated, and he thought it would work well. He handed the bottle to Jack.

Jack poured the lotion liberally over his cock. "Since it's you're first time, why don't you get on top?" he asked. "It'll give you more control of how fast we fuck, and it'll make getting my cock in you easier."

Keith nodded, still in the throes of excitement from Jack sucking his dick. His dick still throbbing, he straddled Jack while Jack put even more lotion on Keith's asshole. Jack wormed a lotion-coated finger inside Keith's ass, and felt Keith instinctively tighten up.

"You're going to have to control that," Jack warned. "The tighter you make it, the more it will hurt...and this particular activity is more about pleasure than pain."

Keith nodded again, and Jack lined up his cock. Nudging the head against Keith's asshole, he said "Now lower yourself gently onto me."

Slowly, Keith lowered his ass towards Jack. The bulge of Jack's cock spread Keith's asshole, then popped inside. Keith grimaced, and let out an "Ouch!"

"Just let it sit there for a minute," Jack suggested, "and relax." He reached out and stroked Keith's hard dick with a lotion covered hand.

Keith stayed motionless as his ass slowly became accustomed to Jack's cock. As soon as he relaxed enough, he slid his ass down another fraction of an inch until it was painful again.

It took many long minutes before Keith's ass was filled with Jack's cock. Keith's asscheeks rested on Jack's pubic hairs. He could feel Jack's cock throb inside him.

"How does it feel?" Jack asked, still stroking Keith's dick.

"Hurts a little," Keith replied. A pause. "But it feels kinda good, too."

"It'll feel real good soon," Jack promised, pushing his cock harder against Keith's ass. "Rise up a little bit, then let it slide back in."

Keith put his hands on Jack's chest and raised his ass a half inch. Jack's cock slid out a little bit, and Keith groaned in pleasure as he lowered himself back onto it.

Jack grinned up at Keith. "Told you it'd feel better," he laughed.

Keith nodded yet again, unable to speak. "Damn," he thought, "this feels fucking fantastic!"

He started moving his ass more, letting more of Jack's cock slide out, then pushing himself back down on it. Jack's other hand, the one not stroking Keith's dick, found Keith's nipple and tweaked it.

Keith was really getting into being fucked. He was moving his ass harder and faster, and in a few minutes his ass was bouncing up and down on Jack's cock. He was making unintelligible groans and moans.

"Yeah," Jack hissed, "ride my cock. Take it deep."

He was pinching Keith's nipple almost painfully, and his hand was hand was flying up and down Keith's dick.

Keith could feel the orgasm building again, and the harder he rode Jack's cock the closer it came. He could barely feel Jack's fingers tearing at his nipple, and was aware of his dick being stroked, but the main pleasure came from Jack's cock slamming in and out of his ass.

Jack was pounding his cock up into Keith's ass as it came down, and yanking it back when it went back up. He could barely hold on to Keith's dick, the movement was just to fast and furious.

Keith finally slammed his ass down onto Jack's cock hard, hard enough to bruise. He threw his head back and groaned "AAHHHhhhhhhhhh" as his cock began shooting cum across Jack's stomach and chest. Jack tried to pump his cock into Keith to reach his orgasm, too, but Keith was pushing down onto him too hard, his dick and ass spasming wildly.

Keith finally came to a shuddering end, and Jack's hand slipped off his dick.

"Greedy little bitch, aren't you?" he grinned up to Keith. "That's two for you and none for me."

Keith looked down at him with a mixture of sheepishness and awe. "Sorry," he mumbled.

"That's not a problem," Jack replied. "Roll over onto your stomach."

Keith reluctantly pulled his ass off Jack's cock. He moved off of him, laying face down on the bed. Jack rolled over on top of him, lined his cock up with Keith's ass again, and steadily pushed his cock back inside him deep.

Even though he was a bit sore, it still felt good. Jack laid fully on top of Keith, his hips slowly pumping against Keith's asscheeks as his cock enjoyed the heat and tightness of the recently-virgin ass.

Keith laid under Jack, enjoying the feel of his weight on him. His ass was getting tender, but he pushed himself back onto Jack's cock with every thrust.

Jack could feel his orgasm build again, and this time he was able to continue, sliding his cock into Keith faster and more forcefully until it exploded, coating the inside of Keith's ass with gob after gob of hot, sticky cum. He shuddered against Keith, his orgasm hard and long.

Spent, Jack laid on top of Keith for a few minutes, kissing the back of his neck. When he recovered, he rolled off onto his back, and scooped arm around Keith, urging him to lay with his head on Jack's shoulder.

"Wasn't so bad, was it?" Jack said. His hand reached across him and stroked Keith's arm.

"No," Keith murmured, getting sleepy. "I liked it."

"Good. I was kinda hoping you'd like to do this again in the future," Jack replied. He heard Keith's breathing slow and turn into soft snores. Jack laid his head back on the pillow and dozed off himself.

The next morning, Keith woke up alone. At first, he thought the previous evening was some kind of kinky, erotic, incredible wet dream. Then, when he sat up, his ass twinged with a small pain and he realized it had really happened, and that he had really enjoyed it.

He got up and went to the bathroom, then headed to the kitchen. As he walked in the kitchen he saw Warren at the table, wearing loose boxers and a t-shirt.

"Morning, sport," Warren rumbled warily. He wasn't sure if Keith still wanted to not play nice or if he'd gotten over his previous anger.

"Morning," Keith said absently, opening the fridge and pulling a container of orange juice out. He still had a lot of reservations about Warren, and had to fight his anger down at seeing him still in the house.

"You and Jack have a good time last night?" Warren asked.

Indignation bubbled up inside of Keith. At first, he thought Warren was making fun of the fact that he'd been fucked by a man, but he calmed himself down and realized that it was simply a question, not an accusation.

"Uh....yeah," Keith said, pouring the juice in a glass. His anger and hard feelings towards Warren started to evaporate. "Maybe the guy isn't so bad after all," he thought. "At least, Mom likes him."

"Listen," Warren said, sensing an opportunity to reach a rapport with Keith, "I'm sorry about the other day. I have a temper, and you set it off. I shouldn't have been so rough with you. But, I wouldn't tolerate that attitude from my son, and I won't tolerate it from you."

One last bubble of anger burst inside of Keith. "Did you make him suck your dick, too?" he said, accusingly.

"Actually, no. That happened when he decided to prove to me he was gay," Warren chuckled.

Keith set his glass down with a thump. "Your son sucked your dick?" he asked, amazed.

"Just once," Warren said. "I refused to believe he was gay and kept telling him that it was a phase and he'd get over it. I think I kind of expected grand-kids from him. Anyway, he pulled my cock out and took the whole thing in one gulp."

Keith sat there with his jaw dropped. He didn't want to believe Warren, but the casual way Warren was relating the story made it more and more believable.

""I tried to stop him, told him that I believed him, but he didn't stop until I got off," Warren continued. "Turns out he's pretty damn good at sucking dick. He's almost as good as Shei...er, some women I know."

Keith almost chuckled at Warren almost comparing Jack and his mother's cocksucking ability. He realized that Warren was trying at least, and almost felt bad for directing so much anger at him. Plus, he was getting a little turned on by the story.

Keith sighed, and said, "Hey, I'm sorry too. I was acting like an asshole. And, you're right....I didn't really appreciate how good the situation that Mom and I are in. I appreciate it now, and I'll do more to help Mom out."

Warren waved his hand. "Don't worry about it. There's really not much you can do. I was just spouting off the other day."

Keith stood up and moved over to stand in front of Warren. "No, there is something I can do," he said, dropping to his knees.

"Keith, you don't have to..." Warren protested, but Keith already had Warren's cock out and was licking the cockhead. He reached down to pull Keith's head off of his cock, but Keith batted his hands away.

Remembering the night before, he tried to mimic the way Jack had sucked his dick. Keith was getting more and more turned on, and enjoyed sucking a dick in his mouth that WASN'T being shoved in.

Warren gave up trying to stop Keith, and lightly rested his hands on the back of Keith's head. "If you insist," he grunted as Keith's mouth worked magic on his cock.

It didn't take long. What Keith lacked in talent, he made up for with enthusiasm. Warren tensed up, his cum boiling out of his balls and shooting into Keith's mouth. Keith swallowed Warren's load, not missing a drop.

Warren relaxed in the chair, his dick softening in Keith's still-sucking mouth, when Sheila walked into the kitchen.

"Warren!" she cried out.

Warren looked at her and shrugged. "It wasn't MY idea," he said. "I may not swing that way, but it looks like your son does." He pulled his cock from Keith's mouth and tucked it back into his boxers.

Keith looked up at Sheila and grinned. "He's right, Mom," he said, "it was my idea." He stood up, walked over to Sheila and hugged her. "I'm going to do my part from now on," he told her, "and I'll be HAPPY to do it."

From that day on, Keith did his part in paying the rent. When word got around to Warren's friends, most of them came by to sample Keith's new-found sexuality. Everybody left the house with a smile. Jack was a frequent visitor.

After a few years, Warren was true to his word. He offered to sign the house over to Sheila, but also asked her to move in with him. She happily accepted the latter, and the house was signed over to Keith, instead. Jack moved in with him.

Keith still "entertained" some of Warren's friends, but it was because he and Jack wanted to.