Training Tim Ch. 01: Handjob Heaven

"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.