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Training Tim Ch. 01: Handjob Heaven

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.
The next morning Doris and Rebecca were having coffee with some of the blood stained underwear on the coffee table before them when Timmy came down the hall from his bedroom.

"Good morning. Hi Mrs. Johnson. Sorry, I mean Doris."

Timmy was about to start another sentence when he saw the underwear and fell silent.

Doris broke the ice. "Timmy, please sit down. Don't be embarrassed. There is nothing to be embarrassed about here. Rebecca told me she has found a number of these briefs in the hamper with blood on them. She was worried and didn't know what to do. Obviously, they are yours."

Timmy had taken a seat opposite the two women and nodded yes.

"Have you injured yourself?" Rebecca asked. "Doris, here, is a nurse and I was hoping that if you were injured she could give me some guidance on what to do."

"Have you hurt yourself somewhere Timmy?" The older woman added. "We need to know because something that is actively bleeding can become infected and then go septic."

Doris had said the magic word, 'septic', so far as Timmy was concerned given what had just happened with his dad. Nervously he asked. "Can it really? I usually don't bleed. Just some scabs that come off sometimes."

"Come stand by me Timmy." Doris said, patting the sofa space between herself and Rebecca.

Timmy got up and stood before the fifty six year old woman and she pulled his pajama bottoms and briefs down to just above where his pubic hair started. Both women were able to clearly see the reddened arc that Rebecca had previously noted and several raw and inflamed areas. One was very recently opened which was apparent by the blood on the inside of his briefs waistband.

"This is definitely not a rash." Doris said, and then to Timmy, "Rebecca thought you might have some allergy to her laundry soap."

Rebecca actually thought nothing of the kind as she had seen Timmy handling his cock and knew that his manipulation of it was what had caused the friction abrasions. This was their way of tactfully broaching the subject at hand. Teaching the boy how to jerk out a load safely.

"This is not that Rebecca. I raised two sons and one of them had something similar going on when he was about twelve."

"Have you been rubbing your penis against your tummy? There is nothing to be ashamed about if you did. It's called masturbation and almost all humans do it. Young men, especially those who don't have sex partners do it the most."

Timmy didn't answer but turned red instead.

Doris pulled his pants down to mid thigh and now his swelling penis was on display where a reddened scabbed area on the upper surface of the crown was easily seen.

"It's as I thought." Doris said, gingerly touching his cock head on the scab. "This must be very painful for you."

Timmy winced and Doris immediately stood up and said. "I'm going over to my place. I have some things over there that can help with this. Rebecca, can you get a towel for Timmy to sit on while I'm gone?"

Rebecca got a towel and Timmy sat down. She couldnt help but marvel at the size of the boys cock. It was nowhere near erect although it had swelled a bit when Doris touched it. He was circumsized because Suzanne had insisted upon that. Even semi flacid he had considerable girth and a very nice classic mushroom shaped head. Rebecca had to be circumspect in her assessment so as not to embarrass him further but his cock was very attractive. She felt a bit guilty ogling the boy but she was after all a very sexual person.

Doris returned with some topical antibiotic ointment and a couple of dressings for his abdomen. She treated and then covered the scabbed areas on his abdomen and then gently dabbled some ointment on his cock head. Timmy swelled further with her touch and Doris could not help but remark, "Oh my. You have got quite the whopper here young man. You need to give it a rest so that it can heal."

She handed Rebecca a few pair of boxer shorts saying, "These belonged to Frank and I had almost forgotten about them. He will need to wear these so as not to chafe the glans and the ointment will need to be applied at least three times a day. The abdominal dressing and ointment can be done daily. He will also need instruction on relieving himself in a less stressful way if you can bring yourself to talk about that with him. I have to go now. I promised another nurse that I would cover part of her shift."

She squeezed Timmy's shoulder and said to him "I'll check your progress tomorrow. This will get better."

Doris left the apartment but she actually had a little bit of time before her shift. Time enough to break out one of her special toys. The thick one. 'My goodness.' She thought to herself.

'It has been way too long.'

******

Rebecca, meanwhile, had a difficult conversation to start.

"Timmy, you never answered Mrs. Johnson's question about whether or not you have been rubbing your penis against your belly. I'll assume that you have."

"I don't do it all the time."

"How often you are doing it is not the problem. It's how you are doing it that is the problem. You probably started stimulating yourself that way years ago, when you first started getting erections, and haven't changed since."

Timmy sat silently next to Rebecca, naked from the waist down.

Rebecca continued, "I could describe the best way for you to stimulate yourself to orgasm or I could just demonstrate. I think it would be better for learning purposes if I were to show you. Would that be ok Timmy? Can I touch your penis?"

"I guess so. It still hurts a bit though."

Rebecca reached across with her right hand and grasped his shaft near the base and gently squeezed it a few times, feeling it stiffen as she did.

"Now, Timmy, I am going to jerk you off. Talking dirty can sometimes enhance the experience and help to get you going so I may say some otherwise inappropriate things."

She pumped up and down about three inches with her hand contacting his balls on the downstroke and coming up about halfway on his lengthening rod on the upstroke. She repeated the motion and then again slowly.

"Do you like the feel of my hand on your dick Timmy?"

"Yes. Yes I do. That feels good."

"Has anyone ever touched this beautiful thick cock besides yourself before today Timmy?"

"No ma'am."

"Oh please! Don't call me ma'am when I have your penis in my hand young man."

Rebecca saw that though she was continuing her expert soft stroking, Timmy was beginning to soften and shrink. It occurred to her that his naivete and embarrassment might make her intended instruction impossible. If she were to be able to demonstrate safe and effective masturbation to the boy she would need to help him relax and to engage his mind in the act.

"Have you ever kissed a girl Timmy?"

Rebecca released his cock and started gently running her hand up and down his thigh.

After a moment's hesitation he replied, "No."

"Do you like girls? Are you attracted to them?"

She undid the top several buttons to her blouse then took his hand and placed it on her stocking covered thigh.

"Yes. Well I don't like boys if that's what you mean."

"It would be ok if you did Timmy. I just want to understand what turns you on. What you think about when you touch yourself."

"Well, I think about girls. I can tell you that."

"Was there a girl back in Idaho you liked? One who you thought about?"

"Yes. There was one. Her name was Julie but I could only think about her. She was promised to one of the elders as his third wife. It wasn't fair."

"So you never kissed her? Touched her?"

"No." He answered disconsolently.

"Would you like to kiss me? To touch me? Just to know what it's like to touch a girl. To learn?"

"Sure! Yes, of course. Would you do that?"

Rebecca was still gently stroking the thigh of her late lovers son, while he sat on the sofa next to her, naked from the waist down. She saw his cock swell a little at her suggestion and said to him.

"Let's go back to my bedroom where we will be a little more comfortable, why don't we?"

She stood and then led him by the hand, back to the bedroom she had shared not long before with his mother, and sitting him on the bed, peeled off his shirt.

Rebecca unbuttoned her blouse and sat next to him on the bed. She gently took hold of his face and kissed his lips.

Timmy sat nervously and then startled a little when he felt the tip of her tongue part his lips and seek entry to his mouth. He kissed her back, somewhat inexpertly at first, but learning as he went. She took his hand and placed it inside her blouse so that he could feel her bra covered breasts. Their kissing grew more passionate. Timmy was a fast learner. Rebecca stopped feeling his hand on her boobs and looked down at his lap to witness his grip on his own cock and the beginnings of his customary masturbation technique. The dressing on his abdomen was in danger of being dislodged.

"No Timmy! Let me show you."

Now that it was fully erect Rebecca saw that the boys penis was enormous. She had difficulty wrapping her hand around the base as it's girth was proportional to it's length. Rebecca had experienced probably over a hundred cocks in her lifetime despite the fact that she was more drawn to women but this one was spectacular. She wanted to devour it but settled for gripping it firmly and feeling it pulse in her hand while she spoke to Timmy.

"Now I'm not sure how much sex education you have actually gotten out there in Idaho but I promised your mom that I would help you overcome your shyness."

Rebecca took a moment to remove her blouse and bra. Timmy reached up to grasp her full breasts and then he had to be coached into being more gentle with his explorations.

"You have a very nice cock Timmy. It will be quite the pussy pleaser when it it properly trained and tamed." Rebecca pumped him slowly and firmly.

"My hand is gripping it tightly like a pussy will. This is designed to slide back and forth inside a woman's vagina, or pussy if you will. The preferred way to induce ejaculation is by pumping your big fat penis inside a womans tight wet pussy until it spurts its semen inside her. That is natures way of making new life."

Rebecca and Suzanne had initiated a number of virgin young men when they had gone through their cougars on the prowl phase and Rebecca was surprised that Timmy had held off coming to this point. Several of the virgins they had seduced had popped almost as soon as their cocks were touched. Timmy hadn't popped. Perhaps it was due to the fact that he was used to the more vigorous, bordering on painful, stimulation he had been providing himself. Rebecca was determined that he be taught newer and safer ways to orgasm. She switched hands when one got tired. She tickled and fondled his balls with the opposite hand.

There were many other tricks she knew but could not employ due to the necessity of avoiding contact with his cock head.

"Would you like to see a pussy Timmy? My pussy?"

"Oh yes! May I?"

In reply Rebecca stripped off her skirt and panties and stood with her shaved box right before the excited boys face. She slid a finger along its length and then dipped it inside, bringing it back out coated with her own excitement.

"See how wet and excited your kissing made me Timmy? You are quite the man. Would you like to touch It? To see how wet you've made me?"

"This can't be happening. I can't believe it."

"Believe it." Rebecca said and then took his hand and guided it between her legs. "Now very gently slide just one finger in."

She sat back down and resumed her jerking of his cock while his finger explored her searing inner walls.

"Ooh!" She exclaimed when he instinctually began to slide his finger in and out.

The fact that he knew he was now giving her pleasure increased his pleasure and brought him ever closer to coming. Rebecca noticed and approved. She wanted him to develop as a considerate lover. Suzanne had asked that she do so. That he so resembled his mom made this whole experience erotic and weird simultaneously. Nevertheless it was happening and Timmy's nut was getting ready to blow. Rebecca had jerked enough loads to know the signs.

"You're getting close Timmy. I want you to come for me."

"Oh my God! That feels so good."

"Come for me honey. Shoot out all that juicy goo."

With a groan of pleasure and a final thrust and hump up into her grasping hand he did just that. The first blast shot straight up in the air and landed in splatters all over his chest, abdomen, and thighs. Several splatters hit the towel and sofa. Rebecca's body was also splashed with some of that geyser and the subsequent lesser spurts coaxed by her continued pumping of his juicing cock. She continued jerking him slowly until the jizz finished seeping from the tip. Her hand was coated. She took a second nearby towel and mopped up the mess they had just made.

"My oh my! Do you always shoot that much?"

"That was the most. It's usually a lot but that was the most Rebecca."

"It was the most I've ever seen, I can tell you that. Now you better go and get dressed young man. I'm going to drive you over to the garden shop today. You'll get the bus afterwards but I thought I'd take you over the first time. There's a bus route that goes directly there and we will follow it so that you will be familiar when you go on your own."

"Ok ma'am."

"Ma'am? Oh please Timmy! I just jerked you off and you shot a huge load all over me. If you insist on respecting your elders how about we settle on auntie Becca as your name for me. I know I'm not your real aunt but as close as your mom and I were I'm as close to an aunt as you're likely to get."

Timmy seemed pleased by this and answered, "Ok auntie Becca. I'll be ready in a jiffy."

When Timmy had left to go back to his room Rebecca wasted no time in retrieving her vibrator from under the pillow and going to work on herself. It wouldn't take long for her to get off. What had just happened was so hot. She must have been masturbating the young man for over thirty minutes. Her arms had grown tired. She had been wet with desire from before the the time Doris had exposed his cock to her view.

She had wanted to suck it. She had also wanted to fuck it but she had some doubts over whether she could accommodate it in her tight hole. It will be fun to try but she knew she would have to wait for all of that. He had to be trained first. His finger felt good but he would have to learn so much more about how to please a woman with his hands, with his mouth, and then with that oh so marvelous piece of meat.

Thirty seconds with her vibrator and her imagination was all it took for Rebecca to orgasm with a very satisfied sigh. Now she would be able to bring the boy to Tonya.

******

Tonya had been briefed on the essence of the conversations between Suzanne and Rebecca in the hospice. She had agreed to be on board with the slow education and training of Timmy. It would be difficult for the thirty nine year old red headed hippie sexpot to go slow but she would play along as her deceased friend would have wanted.

Of the three Tonya had been without a doubt the wildest.

Rebecca and Suzanne had met her at a swingers club ten years before when she had been the focus of a five man gang bang in the party room.

There had been four well hung black men as well as one white who they later found out was her boyfriend of the time. Rebecca and Suzanne had sat on a sofa and played with each other's pussies as they watched the sexual gymnastics unfold. The limber redhead, surrounded by hard cock was able to deep throat with ease. She took thick black cock into her ass like it was second nature. She performed double penetration as well as double anal penetration. Her boyfriend was video recording the whole thing while taking his turn getting his cock sucked and fucking her ass and pussy. He was the only one who went bareback as condom use was strongly encouraged at this club.

Her multiple squirting orgasms were testimony to her enjoyment at being used in this way.

When each man came he rolled his condom off and held it until all were finished. Then they all squeezed out their come onto her heaving breasts to the applause of about twenty club patrons who had enjoyed the show while masturbating or being masturbated by a partner.

Suzanne had been the one to approach her with a towel to sop up the come.

"That was quite a performance! You really got off."

"I sure did. That was a fantasy of mine for a while and it sure lived up to the hype."

"Hi. I'm Sue." Suzanne said, extending her hand.

"Tonya." replied the redhead, taking and shaking the extended hand.

Thus was born a friendship of ten years. Rebecca had taken to the new friend immediately. They had shared many men and many intimacies over the intervening years and now the two remaining friends were to share one more responsibility on behalf of their departed compadre. The training and education of her son in a way that would make his mother smile.

******

When they entered the small garden shop after parking the car Rebecca and Timmy couldn't immediately see where Tonya was. There were a few customers about as well as one or two employees. A young blond with the name tag Madison was at the register.

Rebecca didn't recognize her but then she hadn't been here in over two years and employees do tend to turn over.

"Is the boss around?" Rebecca asked.

"I think she's out back. Some pallets of sod are being unloaded and she usually likes to inspect them."

They headed through the opening to the outdoor plant section and Rebecca caught Madison checking out Timmy's butt. She smiled inwardly as a proud auntie might.

Tonya was indeed busily inspecting the delivery pallets but stopped her work to greet Rebecca and Timmy.

"Great! Glad you guys are here. Ready to go to work Timmy?"

"I don't know what I'm supposed to be doing."

"No worries. A little of this and that. I'll have Ramon work with you today and the next few days to get you up to speed. I think you'll like working here but if you don't, Rebecca and I will help you find something else."

Tonya then sent Timmy off with Ramon to get some coveralls from the little break room she had for her employees and she took Rebecca into her office for a quick chat. It was a productive chat and Tonya was pleased to hear about the masturbation session. Rebecca had previously shared with her Suzanne's deathbed request concerning her son's sexual education and training and the fact that she had asked her to include Tonya. Rebecca of course had included her and now that the ice had been broken sexually she was glad that Tonya would be able to add her experienced hand to the task. Rebecca headed off to get to her job before Timmy returned, now wearing the requisite attire for hauling potted plants.

"Rebecca had to get going but she has left you in my capable hands. You'll do great here I'm sure, so tall and strong." Tonya said, squeezing his bicep as she did.

******

Timmy was kept busy for the next several hours and then in the late afternoon he heard Tonya calling to him.

"Have you had a break? It's well past lunch time and it looks like you're working to impress me in order to get the job. Relax, it's yours."

"No I haven't. I am getting hungry though."

"Come into my office young man. I have some chili I was going to microwave. We can share. I'm hungry too." Tonya said, glancing briefly at the boys crotch too quickly to have it be noticed by him.

When they had finished eating Tonya rose from behind her desk and went to the office door, locked it and also checked that the office window blinds were shut. She took the tube of topical antibiotic cream that Rebecca had left with her and asked Timmy to stand and drop his pants.

He hesitated, so Tonya said to him.
"Timmy, listen to me. Rebecca told me about your problem and that this ointment needs to be applied three times a day."

"I could put it on." Timmy replied. "You don't have to."

"I don't mind Timmy, in fact I'm eager to, given what Rebecca told me about her time with you this morning."

The teen stood but reddened with the realization that his having been jerked to orgasm this morning seemed to be common knowledge.

"Timmy, don't be embarrassed. Rebecca and I have no secrets. We have had sex with each other but not as often as your mom had sex with her. She and your mom were long time lovers. There is nothing wrong with that despite what you may have been brought up to believe."

"My mom?"

"Yes, your mom. Sex between women is not evil or sinful despite what you may have been taught. We all cared for one another and your mother certainly cared about and loved you. She asked your aunt Becca, and yes, she told me that you are going to call her aunt Becca, to help you learn about sex and women in a non judgemental and uninhibited way. Are you willing to learn Timmy? To be trained?"

Timmy considered the question and also remembered how good it had felt that morning when aunt Becca had played with his penis until he had squirted one of his biggest loads ever. Was Tonya offering to teach him about sex as well? He looked at the redhead and imagined how she would look with no clothes on. As if reading his mind Tonya said.

"Would it make you less embarrassed to have me put ointment on your cock if I was undressed too? I can do that."

Tonya turned up the volume on her desk top radio, which had been playing classic rock. She kicked off her shoes and slithered out of her tight jeans. Then to the delight of the youngster she peeled off her panties, revealing a neatly trimmed and fiery red bush. Tonya pulled her sweatshirt up over her head and undid the bra clasp between her breasts so that they sprang free revealing erect nipples upturned invitingly.

"Well, now that you can see mine, I'll need to see yours. At least to put this ointment on."

Timmy stood transfixed while she unzipped his coveralls and slid both them and his boxers to the floor. His penis, even flaccid, was magnificent and beautiful. She dropped to her knees, ointment in hand, to examine it and Timmy could feel her hot breath waft over its surface. Taking the shaft in her hand she applied the ointment over the scabbed area and saw that the dressings Doris had placed on his abdomen were still intact. She did have to resecure some of the tape to the edges but nurse Doris had done an expert job.

"Now there. That job is done. Now for the next job, the hand job."

Tonya rhythmically squeezed his shaft with one hand and grazed the hair on his balls with the the fingertips of the other until he began to swell considerably. She found that the hand grasping him was soon unable to cover the circumference of his growing girth. Her pussy moistened at the prospect of being stretched by this young turgid teen prick but that would have to wait for another day. Fingerfucking was the first skill to be mastered.

Tonya rose to her feet and kissed Timmy while continuing to tickle his nutsack. He kissed her back and even grew bold enough to grab her asscheeks in his hands and pull her close to him.

After a couple of minutes she broke the embrace and sat on the edge of her desk. She had Timmy pull up a chair and sit before her so that he had an up close view of her pussy, made even better when she put one leg on each of the arms of his chair and spread for him.

"Ok young man, this lesson is going to be introductory pussy petting."

Tonya took his hand and slid it up her thigh until it made contact with her pubic hair. She then took his index finger and slid the tip up and down her wet slit.

"Ooh, that feels nice. The opening you are exploring is to my vagina or pussy. It is warm, wet, and snug inside. It is designed to wrap itself around a penis and coax the sperm or juice from it. Feel near the top of the opening."

She directed, guiding him to her clit.

"Do you feel That?"

Timmy nodded.

"That is my clitoris or clit. That's where most of my pleasure nerve endings are concentrated. It's kind of like the tip of that massive cock you have plumping up there."

Tonya spent the next fifteen minutes guiding the boy through a thorough examination of her pussy both inside and out. She had him vigorously sliding two fingers in and out of her slippery box while she diddled her clit. She asked him to note how she liked to have it massaged. She had him concentrate pressure deep inside the front inner wall so as to massage her g spot. She did not orgasm but got close. To avoid suspicion over being in the office too long she knew she had to wind up the lesson, especially if she wanted to allow time to drain the young man's balls.

"Time to get you back to work Timmy. Let's trade places. You sit on the desk."

He did and Tonya gathered a washcloth, some lube, and a small vibrator from her desk drawer. She sat on the chair facing his straining erection and coated her hands with lube. In an expert manner she rapidly jerked his meat from root to just below the crown using a teasing and twisting motion she had perfected on more cocks than she could remember.

She turned the vibrator to a low setting and teased it over his balls and perenium. In less than five minutes she could see them tightening up in anticipation of exploding.

"Getting close baby? Why don't you let go? Come for your aunt Tonya."

She was inches from the tip as she coaxed him, flicking her tongue out and running it over her lipstick covered lips. She saw the head flare and just in time had the washcloth in position to catch the volleys of spunk.

"Oh my! Aunt Becca was right. You do shoot quite the quantity of come."

Timmy recovered from his daze and got himself dressed. Tonya did the same and opened the door for him to get back to work.

"Lunch is over. Glad I could answer your questions." She said loud enough to have anyone within earshot hear.

Madison glanced over from the register. She hadn't noticed when the new guy had gone into the office but did notice that his face was flushed when he came out. She also thought she could make out a dollop of something viscous decorating the red hair on Tonya's head just above her right ear. Tonya followed her gaze and reached up to touch the wet spot.

'Oh well,' She thought to herself. 'I guess the washcloth didn't catch it all.'

*******

"How did your first day at the shop go?" Rebecca asked Timmy when he arrived home off the bus sometime after six.

"It was good."

"Did you learn a lot?"

"I did. There is so much to learn though."

"I'll bet. Did you have a nice lunch with aunt Tonya?"

After a momentary hesitation Timmy sheepishly offered, "We had chili."

"I think you know that's not what I meant. She and I are going to communicate about everything regarding your sexual education and training. This is going to be a team effort."

"Ok then. Well, she put the ointment on and then stroked me like you did."

"Was she good? She's very good you know."

"It was good. It felt really good. Different than you but they were both good."

"Not to worry Timmy. We are not in competition with each other. Over the next few weeks both your aunt Tonya and I are going to milk that anaconda you have in your pants at least twice a day. You have to promise not to masturbate yourself without supervision. We are not risking any more injury. We are also going to teach you how to bring us to orgasm with your hands, how to fingerfuck your new aunts. Are you up for that?"

"Yes ma'am. Sorry, I mean yes auntie Becca."

"Good. I brought pizza home. Let's have some and then see what's on tv tonight. I think you should be good for today. After Mrs. Johnson checks your wounds in the morning we can resume our training."

Timmy smiled and took a slice from the box.

******

The next morning Doris peeled back the abdominal dressing and remarked on the healing evident in the abraded areas. She was pleased that the scab on the cock tip was undisturbed and commended the boy.

"Good boy. Young flesh heals so quickly if it is given a break. Did Rebecca talk with you about how to relieve yourself safely?"

"We talked." Rebecca answered for the teen. Rebecca then noted that the widow had not released her grip on Timmy's penis after having applied the ointment but was instead rhythmically squeezing it subconsciously.

'It must be quite a while since Doris has gotten any.' Rebecca thought to herself. 'Maybe we can invite her to the team. I have to leave town for a few days next week and I'm sure she has a number of things to offer to a young man's education.'

Doris caught Rebecca's stare and followed it to her own hand beginning to pump young Timmy's cock and his beginning to hump in response.

"Oh my! Forgive me!" She exclaimed, rapidly removing her hand and covering the emerging erection with a nearby towel.

"Not at all." Rebecca responded. Then she leaned in to whisper in the widows ear. "Its hard to resist, isn't It?"

"I had better get going. The dressing can probably come off tomorrow and if you like I can check back in a couple of days."

"I think that would be good. Wouldn't it Timmy?"

Timmy nodded and then watched as Doris made her way out. Rebecca removed the towel and said. "That was nice foreplay. Now let's relieve you of your overnight load so that you can get ready for work. You can take care of me tonight."

Next door Doris wasted no time in getting out her little clit stimulator and her biggest dildo. She called it Johnny in honor of her favorite porn star Johnny Holmes. She and her late husband had often watched porn together as an added stimulation to their lovemaking and she had continued the practice albeit infrequently. She got her laptop out and surfed for some appropriate porn to fondle herself to. A few choice keywords found the perfect scenario for her viewing pleasure and Big John was worked in and out of her sopping pussy. She came in minutes and soaked the towels she had placed under her ass so as to save the bedspread.

******

The next several days followed a familiar routine. Rebecca jerked Timmy off every morning. Tonya milked him every day at work, usually waiting until closing time so that they could have more time and privacy for extended training. Over the weekend Tonya joined them at the apartment and Timmy got better and better at finger fucking his two aunts. He asked if he might work his prick into their velvety smooth pussies but Rebecca told him that would have to wait.

"Patience." She told him. "There is so much to learn. You are going to learn about how to please a woman with your mouth and tongue and to have your cock sucked and blown by experts, namely us."

"I can't wait."

"Oh you can wait. It will be worth the wait." Tonya said.

"Timmy, I need to ask you something. Would it be ok with you if I told Doris next door about what we have been doing. She has been very helpful with your situation to this point and I thought that when I was out of town this Tuesday and Wednesday she could help with your morning milking and perhaps you could learn your way around another pussy. Each woman's needs and responses are different so the more experience you get the better lover you will be in the long run."

Tonya chimed in while stroking their young charge. "She's right you know. I've found in my life that variety is the spice."

"So what do you say? Would it be ok?"

"I suppose."

"Good." Rebecca said. "I'll go next door now and speak with her. Why don't you stand up and spray a nice big load over your auntie Tonya while I'm gone so that if I bring her back you'll have taken the edge off."

Timmy stood and stroked his cock while Tonya knelt before him and tickled his balls.

Doris answered the knock on her door and invited Rebecca in when her neighbor asked if she had some time to chat. They spent about twenty minutes going back and forth over Rebecca's proposal and the older woman was not shocked or surprised. She suspected much of what was being confessed after having observed how Timmy was interacting with his late mother's lover. Rebecca was not surprised that Doris had spent a great deal of time fantasizing and masturbating with visions of young Timmy's teenage meat dancing in her head.

While this conversation was going on, next door Timmy was busy self edging and building up control with aunt Tonya's encouragement. When he approached orgasm she would stop tickling his balls and squeeze them instead.

"Not yet young man. Not yet. Wait until auntie Tonya says."

She on the other hand, exhibiting less patience, had masturbated herself to several small orgasms while watching the lewd display of cock stroking taking place directly in front of her kneeling naked body.

The timing was perfect. Just as Rebecca led Doris into the apartment Timmy was coating Tonya's face and breasts with ribbons of thick come, being encouraged to do just that by the orgasming redhead.

"Ooh baby. That's it. Come for me. Come for aunt Tonya. Come on aunt Tonya. Come on my face. Come on my tits. Just come."

"Oh my!" Doris gasped. "That looks like fun."

"Hi Doris. It is fun, and oh so yummy." Tonya said, scooping some of the boy's come from her tits with a finger and feeding it to herself.

"Welcome to the team." Rebecca said to Doris.

"Glad to be a part of a young man's education." Doris replied with a grin.

"This looks like it has healed up nicely." She then added, taking the boys softening prick in her hand and examining it.

"It has Mrs. Johnson. Thanks to you in part." Timmy said.

"Oh Please! Let's call me auntie Doris if we want to be consistent." She said while unbuttoning her blouse and kicking off her shoes.

Tonya was wiping up the come from her breasts and had started to do the same from her face when Rebecca said. "Allow me." Rebecca then licked and gathered the come from her friends face and they shared it with a soulful kiss.

"Oh my. It seems we all have some education to undertake." Doris noted, now down to her bra and panties.

"Yes we do. Yes we do." Said Tonya. "I'm going to take a quick shower while Timmy gets his first lesson on how aunt Doris might prefer to have her pussy pleasured."

That lesson was well delivered and well received as were all of the ensuing lessons over the next several weeks. Timmy's training as an expert and considerate lover was well underway.

His mother would have been proud.
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