P Tom Helps William Lose His Cherry

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*** This is a stand alone story of a series currently in the works. It just couldn’t wait, as it is set five years after the first story. There may be some who are concerned about this story being set with the pastor as the one of the main characters and I understand that can be upsetting. There are plenty of other stories to read, feel free to do that, otherwise you can read Tom’s beliefs about love and sex being a wonderful and beautiful between two consenting adults. ***




It had been five years since Tom moved to the island, and life was going fine. There were the usual ups and downs with his work. The weddings, church parties were always fun. There had been a few funerals which he had presided over, Stanley’s was one of them. Tom consoled Abby there those tough weeks. Deciding there wasn’t much on the island for her, Abby put the house up for sale. She was heading back to college, before she left for the mainland she had repaid him by letting fuck her in the ass.

Rose, Dorris, and the ladies guild still meet with one once every three months for a pegging session in Dorris’s basement. While he enjoyed these sessions and how the women could take out some frustration on him. Tom did miss the real thing. He did meet up with an old buddy from the seminary, who was a pastor too, once a year. They would suck and fuck each other three ways till Sunday. Still he did miss having a hard cock to suck and satisfy.

Over the years he had been tempted to try and seduce Mandy’s husband Bill. They had divorced a little over a year ago, they both accused each other of cheating. Bill had never found out that it was Tom or the women of the island Mandy was having sex with. It was the young lady only a few years older than their daughter who was in her second year of college that Bill was screwing that pissed Mandy off.

Their split had been the talk of the island. With the divorce finalized Bill had left for the mainland since his company was there, leaving Mandy the house and the small food store. Both of their kids were in college and spent their time at home between their parents’ houses.

Returning from his morning run, Tom showered off the sweat. While he was not buff or ripped as some, Tom did not want to get pudgy as some of the older men on the island. Toweling off his short brown hair he examined his reflection in the mirror. Reaching down he toyed with his soft cock, when fully erect it was eight inches long and three around. Letting it go, Tom got dressed, knowing there would be time for that later in the day.

Heading into the church to check on some things he found he was not alone as he expected to be. There in a church pew was William, Bill and Mandy’s youngest. He was a freshman in college who had returned for the summer. Leaving him alone for the time being Tom popped into the office to take care of the few items of the day. Exciting the office he saw William was still sitting there. Opening the doors to the chapel he entered and walked up to the pew William was in.

“William is everything alright.”

Startled William turned to him. It had been awhile since Tom had seen him. While William was never really the athletic type, he never seemed to be able to bulk up beyond the slender man he was. The last time Tom had seen William he was trying to grow a blonde scruffy bread, though at the moment he was clean shaven.

“Uh, everything is fine.” He said looking at his feet.

“Do you mind if I sit down.”

William shrugged, “If you want to.”

There was something troubling William he could tell. Tom decided to take a seat in the pew ahead of him. He found the younger ones did better talking with adults when they didn’t have to look them in the face or feel they were being watched from behind.

“I can tell something is bothering you, William, I usually don’t see you in church besides Sundays.” Said Tom.

They sat there in silence, each lost in their own thoughts before William spoke up.

“I know the churches stance, but can I ask you what you think about gay sex.”

Ah, thought Tom, so that’s what this is about.

“I think sex between to consenting adults is a wonderful thing and should be cherished and embraced by all. Who gives a damn what a few old men think.” Said Tom.

This gave William a smile. “That’s one way of looking at it.”

“William, may I ask why you want to know.”

“I…its…just….ahh…well.” William stuttered trying to find the words to say what he meant.

“I see,” said Tom. “William, I’ll let you in on a little secret. Not many people know this but I am bisexual myself.”

William was surprised by this. “What! Really?”

“Yes, I first found myself interested in other men sexually when I was in high school,’ Tom told him. “The first time I experimented sexually with another man was in college.”

“What was it like?” Inquired William.

“Well, to say it was wonderful and amazing would be an understatement. I was nervous as hell. Thankfully he was someone who had been around the block istanbul travesti and willing to teach me how to please a man.”

“That was nice of him,” said William. “All I’ve done is watch porn, and listen to a few people talk about having sex.”

Tom sat there smiling to himself, he could feel William was becoming more comfortable with talking to him.

“William, does anyone else know about how you feel.”

“Just my sister Trisha, and a few friends from college.” William told him. “I’m still trying to figure it out myself.”

“Well, I’m sure your mom would be understanding, your dad on the other hand.” Said Tom.

Sighing, William replied. “Yeah, he wasn’t happy when I didn’t turn out to be a great athlete like he was in his youth.”

“Ah, parents. They want the best for their kids and to succeed where they failed. Except they can forget that their kids will grow and be adults with their own dreams and lives to pursue.”

“I wish it was that easy.” William said. “I just don’t know if they’ll accept me for who I am.”

“Your not the only one, my parents were atheists, I know they weren’t too happy when I joined the seminary.” Tom turned and looked at William. “We haven’t spoken in years.”

“Wow. Do they know that you’re bi?”

“Nope. I’ll admit it was difficult at first being cut off from them, yet I felt free to live my life as I wanted to.”

“I’m just not sure about talking about it with anyone else till I know for sure.” Said William.

Nodding, Tom gave him some advice. “Well, you’re in that time where you should take time to figure your life out. College is the perfect place to experiment and try new things. Once you get over your nerves you’ll feel more comfortable with who you wish to tell or have in your life.”

“Thanks. I’ll think about it.” Getting up, William asked. “Would it be okay if we meet and talk about this…?”

“Sure, we can do it here, the parsonage, or if you feel like a walk around the island just let me know.” Said Tom.

Tom watched him go, the large shirt and baggy pants hiding William’s body. He could feel his cock stir as his mind wandered over some possibilities. He sat there a little while longer before getting up and heading into town just to see what was going on today.




Walking into Rose’s Used Books Tom was surprised to find a familiar face coming out from behind one of the shelves. A young woman with brown hair in a pixie cut and tight fitting designer clothes stopped in her tracks.

“Abby?” Tom said recovering from the surprise.

“Tom!” She shouted in happiness as she rushed in for a hug.

Bracing himself, he returned it as she wrapped her arms around him.

“Abby, I didn’t know you were in town. How have you been?”

“I’m doing great, just visiting for a week or two, I have some summer courses starting up soon.” She told him.

“When did you get here?” He asked.

Letting go, Abby stepped back and said. “I got in yesterday afternoon. It was kind of spur of the moment thing. Since I don’t have a place, Rose is kindly letting me stay with her.”

From behind her came a woman with her long blonde hair in a ponytail, she wasn’t as tall as Tom. She wore a dark long sleeve t-shirt that showed her ample bosom and tight jeans showing off her sexy butt. Tom could see Rose was smiling as Abby told his she where she was staying, it was obvious to Tom there had been some hardcore pussy eating going on last night, and would probably continue till Abby left.

Since Abby had left the island, her house had been bought by a rich couple on the mainland who had renovated it and turned it into a couples retreat for those willing to pay. Thus leaving Abby with no place to stay beyond the help of friends. Had she asked he would have let her stay with him, though some on the island may have thought that to be a little inappropriate as their minds thought of the worst they could be doing. Though this was mostly the older men, who would have happily bedded Abby if they could.

They chatted for a while, catching up on Abby’s life, Rose had filled her in on some of the on goings of the island. Tom knew Rose was the one who knew everyone’s secrets as they seemed to tell her everything, knowing it would never get out. It was getting towards lunchtime when Tom finally left the store, promising to stop by again as the ladies had invited him to dinner on a night when he was free.

Stopping at Mandy’s small grocery store he picked up a few spur of the moment items. He chatted with Mandy who, like Rose, was in her forties but kept her brown in a bob hairstyle. Her tight red t-shirt showed off her lightly tanned arms along with her massive tits. Thanking her, Tom headed back to the parsonage. He thought about his talk with William and how he longed to meet with his pastor buddy again. They had met two months ago, and there was still a long year ahead of him till they met again.

His thoughts were pushed aside as he found William along with his sister Trisha waiting on istanbul travestileri the bench in the small garden in front of the parsonage. They stood up as he approached. Trisha was like her mother in height which was almost as tall as Tom, she was an athlete and always in shape where her mother was more of a solid build. Where they differed was in their breast, Mandy’s were almost three times the size of her daughters, yet they still strained against the tight shirt of some new band Tom had never heard of. Trisha was wearing cargo shorts and had a few new piercings in her ears and lips that hadn’t been there the last time he saw her.

“Hello,” said Tom as they got up to meet him. “Is there something I can help you with.”

Trisha smiled while William shuffled his feet. “There’s something we would like to talk to you about that we feel we can’t trust with anything else.”

“We can do that. Have either of you had lunch?” They shook their heads no.

Unlocking the door Tom said to them. “Well, if you would like you can join me for lunch and we can talk.”

He entered, they followed behind him into the small house. Trisha closed the door. She and William had never been in the parsonage before. It seemed that only the adults ever visited here. It was a small place almost like a cabin, the living room and kitchen were divided by a small counter, beyond that was the bathroom and bedroom, off to the right of them was the laundry room and storage closets.

Setting the shopping bag on the small kitchen table Tom opened the fridge and pulled out some things to make sandwiches. Grabbing some plates and cups out of the cupboard, Tom told them to help themselves as he sat down. They sat down though William seemed to hesitate, Trisha started making a sandwich along with Tom. They built their lunches in silence, Tom waited for them to say what the problem was. He had an inkling that it had something to do with this morning’s conversation.

With lunch ready Tom said a quick grace. He knew most of the island folk happily attended church; they tended to be less caring at home, this didn’t bother him at all. It was each family’s choice and he wasn’t going to disparage them about it, just as he didn’t shame William that morning as he knew others would.

Sensing her brother wasn’t going to be the one who broached the silence, Trisha decided to do it herself.

“So, William told me that he told you his secret this morning and that you told him one of yours.”

“Yes, we did share some secrets.” Said Tom before taking another bite out of his sandwich.

Setting down her sandwich Trisha said. “I’ve known that William was gay for a few years now as I was the first person he told. I was surprised to hear that you were bi Pastor Tom.”

“Please just call me Tom.” He told them. “And yes I am bisexual, I feel all should be able to love and be loved for who they are.”

Trisha nodded in agreement. “I guess we should get to the meat of the problem. Would you be willing to take my brother’s virginity?”

Tom was drinking as she asked this, water went down the wrong pipe causing him to cough. It took a little bit for him to regain control.

“I beg your pardon.”

Trisha repeated herself with a big smile on her face. “I want you to take my brother’s virginity.”

Tom sat there trying to comprehend what was going on.

“You see my brother is a very shy person.” Said Trisha. “Its why he always chose cross country and track over team sports. Plus, I know he doesn’t have the stones to ask anyone out or just to have sex with.”

“May I ask why you chose me?” Said Tom.

“Sure,’ said Trisha. “You have experience, plus you won’t take advantage of my brother or make him have a bad experience his first time.”

“And if I say no.” Asked Tom.

“Then I’ll tell everyone how you’re screwing our mom.” Said Trisha without hesitation.

“Wait what!” said William, he was surprised at what she just said.


 “”Oh, sorry William I forgot you didn’t know, plus I know he’s fucked most of the women on the island.”

Tom said nothing as he sat there.


 “Really?” Asked William, he was curious as to how long this was going on.

“Yes, and I’m sure he would of had sex with me if the Ladies Guild didn’t have a standing agreement of the women that no daughters are allowed to join their sex club until they turn twenty one.”


 William stared at this sister trying to understand what she had just told him. “You mean you would join next year.”

“If I chose to, all women are told about it when they turn eighteen. They can join if they like or not. Besides, it’s not like I plan on living here, so I probably won’t. Not many of their daughters do. Plus it feels weird talking about mom having sex.”

“But you’re fine about trying to get me laid.” Said William.

“Because I know you’ll never get laid at home, and at college you’re even more hopeless from what you told me.” Trisha replied.

Shaking his head Tom interjected. “Okay, I get travesti istanbul your point. Though Trisha you would only be able to tell the men about the whole Laddies Guild thing and trust me they barely told you about anything that goes on there.”

“So I tell the men and everyone you are bi.”

Tom sighed. “Trisha, as I said before. If you only knew what truly went on at those special meetings. Only the men would learn, though most would think your making up lies to get back at your mom or me for something petty.”

Trisha opened her mouth to speak but was too stunned to say anything.

“Can I ask what really goes on at those special meetings,” said William, intrigued by all this new information.

“No you may not.” Said Tom.

“Okay,’ said Trisha. “I won’t try to blackmail you into doing it. Would you be willing to do it as a friend.”

Tom looked at them both then said. “William is this something you want, no that you really want to do. I don’t want to pressure you into something that you are uncomfortable with.”

William was silent before nodding his head. Trisha smiled, happy for her brother.

“Okay,” Said Tom, trying to remain calm and level headed as his cock strained in excitement. “Before we do anything we need to clean up. Then Trisha, you can sit outside on the bench and make sure we are not disturbed. I’ll put the note on the door saying I’m out on a walk about the island. Everyone is used to that, so it will look like you’re waiting for me to get back.”

“You mean I have to listen to the two of you….” Said Trisha.

“Didn’t you bring your mp3 player,’ asked William. “You can listen to that.”

“Fine, I can do that.” Said Trisha.

They set about clearing the table. When it was finished, Trisha nodded as she put in her head phones and headed out the door grinning. Tom looked at William, who gave him a sheepish grin. Taking his hand, Tom led William to the bedroom and closed the door.




William was nervous as he sat on the bed. Tom had removed his shoes and his dress shirt, leaving him in his pants and white undershirt. William reached down and removed his shoes, he looked around the room as he wondered if he should go through with this. Tom sat down on the bed next to him.

“William, you don’t have to go through this if you don’t want to.” Tom told him.

Turning to him, William said. “If I don’t do this now, I don’t know when I’ll have the courage to do it with someone else.”

“Okay,” said Tom. “Since we’re alone, can I ask you some more personal questions.”

“Sure.”

“Do you know if you’re a top or a bottom.” Asked Tom.

William bit his lip. “I’m not sure. I’ve watched plenty of porn, I guess…”

“Here’s a thought: we could try it both ways, and see which one you like best.” Said Tom.

“Which one are you?” Asked William.

“I’m both, I love to be the giver and the receiver. Is there a type of guy you’re interested in, like a bear or twink.”

William thought about this. “I guess I’ve always been interested in guys who look like me. I’ll admit that if I’m sneaking looks at guys in the gym changing room or showers it’s more about their cocks than their bodies.”

“I see, well once you’ve been another man’s cock, I feel you’ll find yourself looking for more from them than just a hard tool.” Tom said. “Now William, before we start, if there’s anything that you don’t want to do just tell me and we won’t do it.”

William nodded as Tom leaned in closer, with his hand he reached up and touched William’s check. Their lips were close, William could feel Tom’s breath on his face as he closed the gap. The kiss was quick, Tom pulled back for a second before kissing William again. Their tongues meet, exploring each other’s mouths.

With his left hand Tom caressed Williams neck, his right hand wandered down Williams shirt and to his thigh. A shudder of excitement ran through William’s body, he reached out and returned the favor putting his hand on Tom’s thigh.

Breaking the kiss Tom looked at William. “I feel a little overdressed, how about you?’

“I’m feeling a little hot in these,” replied William.

Slipping off his shirt, Tom stood up and began to unbuckle his belt and pants. Taking off his shirt he watched Tom step out of his pants, he could see his cock tenting in his boxers. Getting up William undid his jeans, sliding them down he stepped out of them and stood there in his red boxer briefs.

Tom looked him up and down, he too could see Williams cock straining to break free. Steeping close to William, Tom kissed him. William returned the kiss as their hands roamed over each other’s bodies. William could feel their cocks rubbing against each other through the fabric which separated them. Tom gave William’s firm yet supple butt cheeks a squeeze.

They broke their kiss and looked at each other.

“I think it’s time you felt another cock beside your own.” Said Tom

He stepped back letting William get a good view of him, his fingers reached into his waistband and slid his boxers off his body. William stared at Tom’s hardening cock. It was large, not as large as some he had seen in porn or at the gym, but still pretty large. Tom turned sideways letting William get a good look at his cock as it neared full height.

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