Training Tim Ch. 01: Handjob Heaven

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A virgin young man undergoes sexual training.
10k words
4.63
40.1k
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Part 1 of the 3 part series

Updated 06/09/2023
Created 10/25/2019
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ualmech88
ualmech88
508 Followers

It was unexpected and shocking news.

Rebecca had not even thought this a remote possibility. One Monday, out of the blue, a letter arrived from a young man whom she had never met and whom Suzanne had only rarely mentioned. Now Suzanne was days from passing and this young man was asking to come and stay with her. He was asking if he could move in with Suzanne, his mom.

He obviously didn't know.

His mother's condition was terminal. Days to live. The cancer had advanced and the hospice nurses had told Rebecca to expect the end soon. Realizing the letter as having come from Suzanne's estranged son, she had opened it and read it, brought it to the hospice, and then read it to her dying friend.

Suzanne had not seen her son since he was three and his father had taken him away to that religious separatist sect in Idaho fifteen years before.

There had been no argument about custody or support. Mike had caught his wife one too many times in compromising positions with one too many partners and Suzanne realized that she was not cut out to be a good wife and mother.

Suzanne had always been a highly spirited and extremely sexual person. Her long time friend and lover Rebecca had been quite surprised when the two had first come together and then later married.

In truth, they had only married because she had become pregnant with Timmy.

Mike and Suzanne had been about as mismatched a couple as one could ever imagine. She had been from the San Francisco bay area and sexually active from an early age. The son of a neighbor had been her first sex partner and she had probably gone through almost thirty lovers before she had taken Mike's virginity when they were both twenty five.

He had been raised in a small Mormon community in Idaho and was visiting a friend in California when he encountered Suzanne. They had met at a party hosted by a family friend of his parents.

Mike was an extremely good looking man, a real hunk by most objective standards and Suzanne was immediately hot for him. Over a three day weekend she had him every way possible, despite having to overcome his extreme sexual naivete. He was a clumsy lover and a bit of a male chauvinist. Overconfident and underperforming.

If his sperm hadn't been so potent and she hadn't been impregnated up as a result of the three day sex marathon, she wouldn't have agreed to the union, even as short lived as it had been. Mike heard through the grapevine that she was pregnant and had insisted on marrying.

For her part, Suzanne had hoped she could bring him up to speed sexually, and projected that over time he would become less of an ass. Neither had happened.

Rebecca thought her friend's attempt at the married life a major mistake. The two friends fell out of touch from mid pregnancy to just after Mike left for Idaho with his son. When that happened Suzanne had reached out to her for support.

Rebecca had been there for her then and in the years since. Along with their other long time gal pal Tonya, the trio had been partners in the pursuit of wanton hedonism. There were no regrets about the lifestyle they had chosen, at least not on Rebecca's part. Now Suzanne was days away from dying and her estranged son was coming by bus from Idaho to the last address he had for his mother. Suzanne had sent him a few birthday cards over the years and some must have found him so he had been able to look for her from the return address. There was no way now for Rebecca to contact him and wave him off, or to explain what was going on with his mom.

*****

Suzanne was weak and couldn't talk at length. When they first discussed the letter and Timmy's imminent arrival she was hoping she could hang in long enough to see him and let him know that she never stopped loving him. It was agreed that when Rebecca wasn't home at the apartment she would leave a note on the door asking him to knock at the neighbors. Mrs. Johnson, the widow in the adjacent apartment, was usually home and would no doubt agree to be the back up contact.

Tuesday brought no answers. Mrs. Johnson had agreed, as expected, but there was no knock on the door from Suzanne's son Timmy. The letter he had sent his mother stated that his father had recently died of an infection related to a work injury turned septic. Some friends had tried to convince Mike to seek treatment but his odd ideas about faith healing and aversion to modernity had sealed his fate.

Mike had parted from the greater Mormon community they had initially relocated to and he and Timmy joined a break away sect. There was so little contact with the outside world in this smaller community that it was remarkable Timmy could write as good a letter as he did.

Mike's brief experience in the fast moving world of the bay area had scarred him and he wanted to insulate his son from the evils of technology, modernity, and most of all, promiscuous women. He had not exactly poisoned the memory of his son's mother for the boy but had described her as a wayward person in need of their prayers.

They lived in a cabin with electricity and plumbing but Mike made few other concessions in so far as getting up to speed with the modern world. A woman from their sect had home schooled her own children and Mike prevailed upon her to educate Timmy.

She had done a remarkable job. There was no internet access within the sect by choice but there was a reasonable variety of books circulating among the sect members and Timmy had devoured most of them. Some of the members travelled to and from the nearest large town and made use of the library there. The librarian was liberal and understanding about return dates so many community members got a chance to read a book that had been borrowed before it was brought back to town.

Timmy was a very intelligent young man and had availed himself of as much education and contact with modernity as was possible given his circumstances. He was also so very naive and immature in many areas, especially in regard to the opposite sex.

Wednesday brought no news and no appearance by Timmy. Rebecca and Tonya both visited Suzanne that evening. The nurses told them that she had rallied some and they both thought that she was perking up in anticipation of seeing her son for the first time in so long.

Tonya and Rebecca talked a lot about old times. Many fun and wild times that the three had shared. Tonya owned a garden and plant store in Marin county and they chatted about how that was going. Business was booming apparently. Suzanne mostly listened and smiled. She always needed less pain medication when her friends were visiting.

Rebecca had gotten into the habit of sleeping late so it was not unusual for her to be unconscious when the buzzer to the apartment startled her on Thursday around noon. It took a moment to have the sound register in her brain. When she got it together to recognize it as her buzzer she called out towards the front door, "Just a minute. I'll be right there."

Rebecca threw a robe around her naked form and padded to the front door of the apartment she had shared for years with Suzanne. They had often paraded around in the nude when alone together and Rebecca's forty two year old body was holding up quite well. It was probably all the sexual gymnastics over the years that had kept them both in trim. "Better than hot Yoga." Suzanne had once said to her.

She looked through the peephole and couldn't quite make out who was outside. She was very glad she had put the robe on in case it was Timmy outside and she pulled the sash a little tighter before opening the door. The young man outside looked at her with an expression of fear and hopefulness blended together.

"Mom?" He asked tentatively.

"No. I'm not. I'm Rebecca, your mom's friend. You must be Timmy."

He looked at her and said nothing for a moment or two and then Rebecca said, "Come in. Come in. You must be exhausted. You took the bus? You must not have slept much."

Timmy came in and Rebecca had him sit on the sofa while she went back to the bedroom to get more fully dressed.

She put on an appropriate outfit and sat across from Timmy, considering how to deliver what she was sure would be difficult news to absorb. He looked exhausted. His clothing looked little better than rags and in dire need of washing and mending. He had what looked like a laundry bag at his side stuffed with what were probably all his worldly possessions. He looked dead on his feet.

He also looked a lot like his dad. Dark haired, handsome, and very well proportioned. Probably about six foot two or three and well muscled. 'He must have to beat them off with a stick.' Rebecca thought to herself.

"Your mom is not here right now but this is her home. You didn't come to the wrong place."

Timmy said nothing which forced Rebecca to continue.

"She is sick Timmy. She's in the hospital." Rebecca made a point not to say hospice. Revelation of the situation in stages was her plan, one which Suzanne had endorsed when they had talked about how to tell him what was going on.

"What's wrong?" Timmy asked plaintively.

"We can discuss that when we get there this evening. I was going to visit her then and she can tell you more than I can."

"Can't we go now?"

"No sweetie. We will go this evening. Forgive me for noticing but you look dead on your feet. Why don't we get you a quick wash up and then you can sleep for a few hours in the guest bedroom."

Timmy was too exhausted to argue with that and he staggered back down the hallway as Rebecca led the way.

"This is one of your mother's robes. I know it's a bit small but it will have to do for now. Take off your clothes and leave them on the floor. I'll wash them later. No offence but they really need a good wash."

"I know." Timmy said apologetically.

"No worries. You've been through a lot sweetie. I'm going to get the shower going. When you're in the robe come down to the bathroom and I'll give you privacy to shower."

Timmy did just that and while he was showering Rebecca examined his clothing and made the immediate decision that they would be tossed rather than washed. They were that threadbare. She had to stop by her office to take care of a few things but knew she would have time to buy some clothing for this unfortunate young man.

When he had finished showering he allowed Rebecca to lead him back to the bedroom where he fell into the bed and was unconscious almost before his head hit the pillow.

The robe had ridden up a bit and the lusty cougar part of Rebecca couldn't help but admire his well formed butt and legs. The maternal part of her, what little there was, pulled the sheets up over the sleeping boy and she got ready to head out.

She called Tonya and told her about Timmy's arrival. It was agreed that Tonya would get to the hospice a bit early so as to prepare Suzanne for his visit this evening.

Rebecca did indeed have to stop by the office as she had said. She was taking some family medical leave, but her department head had some projects assigned to Rebecca's team which needed some crucial input from her. After her stop at the office she visited a men's clothing store and picked up some underwear and sweats for Timmy. Without knowing his exact sizes this was about as adventurous as she was prepared to be. She also picked up a pair of size thirteen men's sandals because the shoes he had arrived in were as bad as the clothing.

Back at the apartment she left Timmy sleep away in the back bedroom while she worked from home on her computer. She had done Mrs. Johnson next door the courtesy of letting her know of Timmy's arrival when she had gotten back from shopping.

"Let me know if there is anything I can do. The poor boy." The neighbor had said.

"I will Doris."

"My sons were so devastated when their dad passed five years ago and they were in their late twenties by then. I can only imagine how hard this is going to be on this young man. Losing his dad and then having to get this news about his mother. How old is he anyway?"

"Eighteen or nineteen. I'm not exactly sure. Almost nineteen I think, but Suzanne will know."

"He knows she is in hospice?"

"Actually, I said hospital. We didn't have much time to talk before he collapsed from sleep deprivation. Not sure how I'll tell him exactly."

"Would you like me to help? I had to break the news to my sons when Frank got his terminal prognosis."

"Would you Doris? I would be so grateful."

******

At six pm Rebecca fetched Doris from next door and then went to the back bedroom to wake Timmy while the older woman waited for them in the living room. When Rebecca opened the bedroom door she noticed that Timmy was still fast asleep but now on his back and had thrown the sheets off in his thrashing. As a result he was splayed out naked and Rebecca could admire his trim young body. She crossed to pull the sheet up over him and took note of a red arc across his lower abdomen just below his bellybutton. There were a couple of scabbed areas and it seemed to her a curious inflamed area. A rash? There was no time to ponder further as he started to rouse and she quickly pulled the sheet up to cover him.

"What time is it?"

"Almost six fifteen honey. I was coming in to wake you. We are going soon to visit your mom."

"Uh, ok."

"Here honey. Put these on. Your other clothes aren't ready yet." Not ready for the trash bin, thought Rebecca, as she handed him the underwear and sweats and pointed out the sandals. She left him to dress and a few minutes later he emerged to see the two women seated on the sofa.

"Timmy, this is Mrs. Johnson from next door. She'll be coming with us to see your mom."

"Hello Mrs. Johnson."

"Hello Timmy. It's nice to meet you. Rebecca told me about the letter you sent. That's so terrible about your dad."

"Yeah it stinks. He should have gone to see a doctor but he wouldn't. Why wouldn't he go Mrs. Johnson? Why?"

"I have no way to answer that Timmy. I don't know if anyone can. You can call me Doris by the way. Being called Mrs. Johnson makes me feel so old."

On the twenty minute ride to the hospice with Rebecca driving, Doris explained about Suzanne's condition and prognosis. She further explained that his mom was in a facility called a hospice and what it's purpose was. Rebecca was amazed but probably shouldn't have been about how tactfully and empathetically Doris conveyed all of this information. Doris was, after all, a registered nurse and had much experience in dealing with such matters, her own family's prior circumstances being just one example.

By the time they were entering Suzanne's room Timmy was prepared to be consoling versus having to be consoled. Tonya was already in the room. Suzanne looked up at her son as the three entered and managed the best smile she could muster.

"Hi Timmy. I am so glad to see you."

With a slight sob Timmy leaned over and kissed Suzanne gently on the forehead.

"I'm so sorry Timmy. So sorry I'm sick."

"Please Susie, don't apologize for being sick. You will make us all cry." Tonya said, wiping a tear from her eye.

"Yeah mom. It's not your fault. Are you in any pain right now?"

"Not bad. The nurse gave me something about an hour ago. It makes me a bit tired but I'm good for now."

Timmy sat in a chair at her bedside and they began to talk, each of them taking turns sobbing occasionally.

Doris and Tonya decided to give them some space and left the room to go to the visitors lounge and Rebecca retreated to a chair on the far side of the small patient room, out of earshot.

Mother and son talked for thirty minutes and then Suzanne started to fade. Rebecca told Timmy that they needed to go and that they would return the next day.

Friday afternoon Suzanne had a lot more energy. She actually had an appetite for the first time in weeks and both Timmy and Rebecca were fooled into thinking that she might be getting better. When they got back to the apartment Doris stopped over to see how the visit went. Rebecca shared her impression of Suzanne's apparent rallying of health.

"That is not at all unusual Rebecca." Doris said. "It's similar to a final flare up of a candle before it eventually flickers out. The weight loss is real. The treatment has run its course and the end result is unchanged and imminent. I have seen this before but you should take advantage of her increased energy."

They did take advantage. Friday evening and again Saturday morning both Timmy and Rebecca had a lot of time with Suzanne. Rebecca gave Timmy plenty of alone time with his mom and he didn't object when she asked him to leave the room a couple of times so that she could be alone with her oldest and dearest friend and lover.

In the wee hours on Sunday morning the flame flickered out and Suzanne fell into a coma. Monday, she passed with Tonya in the room and holding her hand. Rebecca and Timmy were on the way when Tonya texted the news. Because it was expected and marked the end of a period of pain and struggling it was less devastating to all than it would have been otherwise and in some ways a bit of a relief.

Besides arranging for the funeral the group was left with the conundrum of what would become of Timmy. Tonya offered to take him on as a helper in her garden store and there was a bus route directly from the apartment to the store. Rebecca had promised Suzanne that he could stay for as long as he needed. The two had been joint owners of the condo and although Suzanne had left no will directing it, Rebecca would treat the boy as if he had inherited some interest in the place.

That week was very busy, given the funeral and it's aftermath. Rebecca bought Timmy a more complete wardrobe now that she could get exact sizes. He didn't seem to know his measurements so she had to get her tape measure out and gather them herself.

One thing she noted was that his underwear, which he placed in the hall bathroom hamper had blood stains. The sheets to his bed also had some blood spatter. She was concerned to the point of intervention and headed back to his room one evening after he had said he was turning in early. Rebecca had a fist raised to knock when she saw through the slightly ajar door, Timmy lying on his back on the bed and grasping a very sizable erection. She had seen erections before, and even a few as large as this one. She had also watched many men masturbate themselves for her viewing pleasure and those occasions had turned her on incredibly. She had seen men masturbate and without a doubt that was what Timmy was doing. It was however, the most unusual way to masturbate that she had ever seen. He was pressing his erection to his abdomen and rubbing it back and forth like a windshield wiper so that the cock head was stimulated by the friction.

That would explain the red arc she had noticed on the first day he had stayed with her.

It must be the only way he knew how to masturbate and if he was anything like the average eighteen year old male that was a lot of dry friction to subject sensitive flesh to. She decided to let it go for now but to ask Doris for advice on how to talk with him about this. Rebecca had been given permission and encouragement from Suzanne to educate her son regarding sex, so that he might develop a healthy knowledge about his body and how to become a proficient lover. She didn't want him to become like his dad.

Doris was home and Rebecca told her what she had seen and surmised. Once again the older woman came to the rescue with a sensible plan. They would both have a talk with him in the morning. They would present the blood stained underwear as evidence of their concern and then allay any fear he might have about his masturbation being anything but a normal development. Whatever crazy thoughts his dad and that community in Idaho had instilled in him regarding sex had to be tamped down. Suzanne had shared with Rebecca that her son thought impure thoughts were sinful and that women were to be avoided. He had been cautioned not to touch himself lest the lust demons sent out by women create a hold on him. All manner of backward and shame inducing teaching had been foisted upon the boy and Suzanne counted on her friends to undo it as she would not be around to do so.

ualmech88
ualmech88
508 Followers