P Tom Helps William Lose His Cherry

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jastim
jastim
31 Followers

"Do you like it." Tom asked.

William nodded.

"Well fairs fair, would you please show me yours."

Grabbing his waistband William hesitated for a moment then bent over and shoved them to the floor. Stepping out of them he stood up. Tom could see William's cock was of average size. He guessed it to be six inches long. and about half as thick as his own. William kept his hair shaved smooth, as were his balls. The purple head seemed to catch the light just right, Tom wanted desperately to suck it.

Tom stepped closer to William. "Do you want to touch it."

"Yes," said William, reaching out.

He wrapped his fingers around Tom's hard shaft as he gently slid his hand up and down the' trimmed shaft. The skin felt soft, he could feel the heat radiating from it.

"I think before we get to the fucking, you should get to feel what it's like to have someone else bring you to orgasm." Said Tom.

William let go of the cock as Tom guided him to the bed. Sitting down William watched as Tom got on his knees between his legs. Running his hands on Williams thighs, he got a close up view of this virgin's lovely cock. Taking it into his hands he gently stroked the shaft as he fondled his balls. William moaned in pleasure, a feeling of electricity seemed to run through his body. Closing his eyes, he savored the moment he felt Tom's hot breath on his glands, just before the moisture of his warm mouth closed around the tip.

Tom ran his tongue over the tip of Williams cock, he licked at the slit, before releasing it from his mouth.

"You have a beautiful cock, William. It tastes lovely."

Before William could reply, he took him back into his mouth.

"Oh God!" Moaned William. "This feels amazing."

He watched Tom bob up and down on his hard cock. He could feel his tip hitting the back of Tom's mouth. William worried he was too big for Tom to get all the way down his cock like he had seen in porn. What William didn't know was Tom was a pro a deep throating cocks, as the Laddies Guild members with their hard strap-on could attest to. It wasn't long before Tom's lips rested at the base of Williams shaft, he loved the feel of this young hard cock in his throat. He held it there for a few seconds before backing off and taking a deep breath, he stroked the spit covered shaft as he grinned at William.

"I bet you never dreamed a blowjob would feel this good."

"Fuck no, its fucking amazing." Said William

Tom licked the underside of his shaft, then he told William before going back to sucking his cock. "If you think this if amazing just wait till we get to the actual fucking."

Leaning back on his elbows William closed his eyes, he moaned in pleasure as he savored the feeling of the blow job. Taking the cock out his mouth, Tom licked and sucked on Williams balls taking each one into his mouth.

"Fuck that feels great."

There was one thing more he wanted to do, to help this young man get over the edge and ready for the next thing. Reaching into the drawer of the night stand next to him, Tom pulled out a bottle of lube, closing it he went back to sucking William's cock so he could see what he had planned to do next. Covering his finger on his right hand with lube, Tom traced back from the balls towards this new unexplored hole. He tickled the hole as he sucked. Williams moans of pleasure to him all he needed to hear to encourage deeper exploration. With a little effort Tom pushed in.

"Holy fuck." Shouted William as the tip of Tom's finger sent jolts of electricity through him.

Tom pushed in a little more and wiggled his finger about.

"Oh fuck. Fuck that feels..." William didn't finish.

He exploded into Tom's mouth. Tom, who had felt William's cock beginning to twitch, had backed off till only the head was in his mouth. The first large wad of warm cum hit the back of his mouth. At least five more shots almost as large as the first followed. Letting his lips slide off the head like he was removing a lollipop, Tom looked up at William. The young man was flat on his back, eye's closed, he was lost for words at the feeling running through his body.

Swallowing the sticky salty load, Tom stood up. His own cock and balls begged for release, he knew it wouldn't take him long to burst. Tom wanted the first time William got fuck to be long and memorable, not short and forgettable.

"It looks like you really enjoyed that." Said Tom.

William opened his eyes and looked at him. "I've never felt something so amazing as that."

Tom smiled. "Just wait for later. Do you think you could return the favor."

Sitting up William said with some nervousness in his voice. "I can try."

"Don't worry about not being great. You have a lifetime to become a pro like me." Tom told him as William got on his knees.

He flashed Tom a quick smile, then he got all serious as he got his first real up close look at another man's cock. William took hold of its shaft as he lifted it and examined it from every angle. The heat pulsing from it, the smell of its musk, and the glistening bead of precum that seemed to grow as he gently stroked. With his tongue he tried to replicate what Tom did to him, he licked the underside of the shaft all the way to the tip. The warm clear sticky goo was wiped clean. It tasted sweet, salty and savory. Slowly he took the head into his mouth. He knew he wouldn't be able to deep throat Tom, so he told himself to try his best.

He ran his tongue around the head, then slowly began to suck up and down. What he lacked in skill he made up in enthusiasm. Tom ran his hand through William's blonde hair.

"Your doing good." Said Tom encouraging him.

Tom tried to last for a little while, he wanted William to get some experience before he blew his wad. He closed his eyes, trying not to picture that brand new ass below him just waiting to be fucked. Tom felt his cock hitting the back of William's throat, he looked down and saw William was about halfway down his thick shaft.

He smiled at him. "That feels good. Don't try to take it all in on your first time."

William backed off and took a deep breath. "I don't think I can fit it all in my mouth."

"It takes time and practice, which you'll have plenty of time for later." Tom told him. "For now do what you can, and use your hand to stroke the rest."

Nodding William did as he was told. With his right hand he worked the base of the shaft, his mouth covering the rest. It took a little bit before he found a rhythm which worked. Closing his eyes Tom waited he could feel his orgasm slowly starting to build.

After a few minutes of sucking which had gone from sloppy and unsure to some confidence and control, Tom felt his balls begin to tighten.

"William, I'm going to cum soon. You don't have to swallow if you don't want to."

Releasing his cock William said. "I want you to cum in my mouth, I want to taste it."

"Good lad." Said Tom.

William went back to sucking but Tom had other ideas. With both hands he held onto William's head as he thrust in and out of his mouth. William looked at him in surprise at this new way of giving a blowjob he had only seen in porn but hadn't thought about trying. Tom pulled out only to the tip as he felt his cock twitch. Rapid shots of hot gooey cream filled Williams mouth. He struggled to hold it all as he felt it start to slide down his throat.

Taking Tom's cock out his mouth William swallowed the thick load. II was sweet and salty, like the precum. Tom told William to stick out his tongue, Grabbing his cock Tom stroked out the last few drops onto William's waiting tongue, he then licked the head of Tom's cock clean.

"So, William, how are you liking it so far." Asked Tom as William stood up.

Giving him a quick kiss on the check, William replied. "I'm loving it."

"Thats good, now it's going to take me a few minutes to recover." Said Tom, indicating to his softening clock.

Going over to the dresser he opened the bottom drawer, reaching under some clothes he grabbed two butt plugs. One was long and slender, the other one was the same length, only wider. William looked at what Tom held in his hand.

"Don't worry. I wasn't going to just tear you wide open with my big cock." Said Tom, grabbing the bottle of lube. "Get on the bed and lie down on your back."

William did as he was told. Crawling on the bed next to him, Tom had William hold onto his legs exposing his hole.

"I want to see your face when you feel it." Said Tom lubing up the thin butt plug.

Applying lube to his finger he rubbed it over Williams hole, and inserted just the tip, the ring tightened around it.

"Just relax, the more you worry the harder this will be." Tom told him.

William nodded as Tom pushed the tip of the slender butt plug in. It felt strange at first, then feelings of pleasure started to take over. When it was fully in Tom waited a few seconds, before slowly pulling all the way out. A feeling of emptiness swept over him, William wanted it back in. Before he knew it Tom was shoving it back in and out. Soft moans escaped from William, as he enjoyed the waves of pleasure washing over him.

Working the butt plug Tom judged when he thought William was ready for the next step. Removing the slender plug he lubed up the wider plug and shoved it in.

"Oh fuck,' said William, "Its so fucking big."

"If you think that's big, I'm going to be huge." Chuckled Tom.

Moaning, William replied, "I can't wait."

Tom smiled. "Well if I had to say it, right now I think you're a bottom, but we will let you try topping me later."

He touched Williams' stiff cock. "Looks like someone is excited."

William didn't say anything as Tom slowly rubbed his hard shaft. Tom could feel his own cock coming back to life, he continued to work on readying Williams hole with the butt plug. It didn't take long before Tom felt he was ready. Reaching into the nightstand Tom grabbed a condom, it was one of the things he had implemented as the result of having sex with a lot of young fertile women. Wrapping his cock he covered the condom in the water based lube.

Removing the plug, Tom got into position. He waited till William opened his eyes.

"Are you ready?"

William nodded. "Yes, please fuck me."

He felt Tom pushing the tip of his cock against his hole. William didn't have to wait long for the moment he was waiting. The tip of Tom's cock slipped in, slowly he pushed.

"Oh fuck, your so tight." Tom told William as he waited for him to loosen up.

William was gasping in surprise, it felt different from the plugs. Yet, it felt so amazing he could hardly believe what was happening.

"You cock feels amazing in my ass." Said William.

Shivers of pure joy shot through him as Tom grabbed his cock. Pushing all the way in, Tom slowly began to pull out. Stopping about halfway out, Tom pushed back in. Slowly he repeated these strokes, he was patient as he waited for Williams tight hole to become ready for a hard pounding Tom wished to give him.

"Oh god. Oh fuck." Moaned William repeatedly as Tom slowly fucked him.

Tom loved the look of stratification on the young man's face. Feeling William loosen beneath him, Tom increased his pace.

William responded to this by saying, "Oh shit...oh fuck yes, fuck me Tom."

"You like getting fuck, you little bottom bitch."

"Yes I loved getting fucked." Said William.

Grinning Tom said. "Are you my bottom bitch."

"Fuuuck." William closed his eyes. "Yes I'm your bottom bitch."

"Good," said Tom.

Stopping, he pulled out of Williams' ass.

"Why did you stop?" Asked William.

"Cause it's time to give you the real fucking you deserve. Get on your knees." Order Tom.

William rolled over, getting on his knees he looked back at Tom. Paying him no head, Tom spread Williams legs and raised his ass in the air.

"Are you ready." He asked him.

William nodded.

"Say it."

"Please fuck me." William said, wiggling his ass.

He yelped as Tom gave his ass a playful slap. Lining up Tom shoved his cock all the way in. Giving it a few experimental strokes, Tom grabbed hold of Williams hips and began to fuck him. Their hips slapped together as Tom started to go faster with each thrust. William had only imagined what it was like to be fucked doggy style as he had watched porn. Now it was happening in real life.

"Fuuck, this feels so good." William moaned.

Tom said nothing he was in heaven, it had been to long since he had fucked an ass this great in a long time. Reaching forward he grabbed a handful of Williams blonde hair and pulled him upward.

"Is that what you like bitch."

"I fucking love it." Cried William.

"Good." Said Tom shoving his head into the pillow.

Leaning over William's back, Tom wrapped his arms around his torso and slammed his hips into William's ass. He rammed it over and over again. William was amazed at this new found savagery, he never thought that he would be fucked like this. As he pumped, Tom felt his balls beginning to tighten. It wouldn't be long, soon he would blow his load. Tom wasn't sure how close William was to cumming, though he wasn't too concerned.

"Fuck William, I'm about to cum."

"Cum in me," Said William.

William was close to cumming, but wanted to hold out. He wanted to cum in Tom's ass.

"Fuck I'm cumming," said Tom.

"Oh fuck! That feels amazing." William said, as he felt Tom's cock twitching inside him.

Tom collapsed onto William's back as he shot his wad. "Oh, fuck. That was heavenly."

Regaining his breath, Tom pulled out of William and flopped onto the bed. Turning around William moved towards Tom's dick, pulling off the condom he licked and sucked the last of the cum out of Tom. Seeing what was going on Tom tried to push him away.

"There'll be time for that later. Right now I want your cock inside of me." Tom told him. "Grab a condom from the drawer, it may be large on you but it should still work."

William did as he was told, slipping the condom on easily and lubing it up. Tom had gotten on his knees, he had drizzled some lube between his cheeks and spread it with his fingers. He inserted a finger into his hole as William climbed back on the bed behind him.

"I know you won't last long, but I want you to get a feel of what its like to fuck someone." Tom told him.

"Um, thank you." Said William.

"Don't thank me just yet. Now stick that young hard cock in me."

Lining up William held onto his shaft as he pushed in. While Tom was used to getting fuck, William was stunned at the feeling of persons asshole squeezing his cock.

"Holy shit, you feel so good. "Said William sliding all the way in.

Giving it a few experimental thrusts, William started to pick up the pace as he fucked Tom. Though he loved this feeling, he wished it was him getting fucked. It seems he was a bottom after all. Once again where William was unskilled he made up with enthusiasm, thought Tom. After all he too was once young and inexperienced and thought that all you need to do was pound the shit out of another's ass to fuck them. Pushing the thoughts from his mind, Tom focused on the feeling of William's slender young cock pushing against his prostate. He could feel his soft cock stirring to life again.

Tom had been right about William not being able to last long. From the fucking he had received and fucking he was giving pushed William over the edge.

"Fuck, I'm cumming." Said William as he felt the waves of pleasure wash over him.

William stayed in Tom till his cock stood still, then he pulled out. Pulling off the condom he tossed it in the waste basket as Tom sucked his softening cock.

"Man, I wish I could have lasted longer." Said William.

Letting go of William's cock Tom sat up and kissed him. "Next time, you can fuck me next time."

"When will that be?" William asked.

Tom looked at him while fondling William's soft cock. "I'll let you know, as you're not the only one who wants my cock inside them."

They kissed again.

"First thing we need to do is get you cleaned up and dressed. No doubt your sister is trying hard not to think how long we're going to be or what we're doing." Said Tom.

Taking his hand Tom led him to the bathroom. Damping a wish cloth he lathered it up with soap and handed it to William. Taking the cloth William ran it over his body, wiping away the sweat and smell of sex. Returning to the bedroom Tom grabbed William's clothes, he brought them back as William finished cleaning up.

Getting dressed, William gave Tom's cock one final kiss before taking his leave. Outside he found his sister waiting for him. She looked at him and smiled.

"So did you enjoy." She asked.

William smiled at her.

Getting up, Trisha stretched. "I'll take that as a yes. Come on, let's get out of here before anyone notices."

They head back towards their mom's house.

"So are you going to tell me all about his cock now?" Asked Trisha.

"If you want to know, go find out for yourself." William told her.

"I think I'll pass, you and mom have had sex with him, I really don't want to be the third." Said Trisha.

William laughed. "If you say so."

Back at the parsonage Tom looked at the corner of the room where he knew Rose's hidden camera was. Well Rose, I hope you enjoy that when you see it. Going to the bathroom Tom stepped into the shower. Turning on the water, he cleaned himself off as he thought about a possible night that would work for William to come back again.

jastim
jastim
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AnonymousAnonymousalmost 2 years ago

As a freshman at HC in the 80's I was slowly seduced by one of the Jesuits, eventually I ended up sucking his cock in his office once/twice a month. Finally in the spring, he popped my cheery, fucking me at a bungalow not far from campus until the term ended. He moved on, I went straight, as it wasn't the time to be getting ass fucked by men.

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