Training Tim Ch. 01: Handjob Heaven

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.